She awoke to the sickly smell of a woman’s perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence.
“Hello again ‘Emma’; that’s a very pretty name you’ve chosen for yourself, we shall soon have you worthy of being Emma, and you’ll soon know your place amongst men, and women.” The woman was sat with her legs crossed in a throne-like chair, no store clothes now, she wore a one-piece black leather bodice which accentuated her mature curves exquisitely, and black seamed pantie hose displaying the full glory of her long legs. Emma’s sissy cock stiffened against the chiffon, scared as she was. The domme smiled as she spoke again.
“That drug is a wonderful thing; you’ve told me everything whilst in a trance. I know you’re submissive, I know you want to be a girl; I know you are really Emma inside. We are going to help you realise all your dreams. You are ours now; you will become Emma completely over the coming months. You will then realise someone else’s dreams; you will be sold to a suitor.” She laughed at the look of distress on the sissy’s face as a large burly and naked male walked in. Emma’s cock stiffened as she felt truly submissive and vulnerable now. The domme strutted over to Emma, stood behind her and held her head up as she knelt trembling.
“This is Kurt, he is one of many men who will master you and train you. You will now suck his cock for the first time.” The big male did not smile; he slapped Emma’s face making her eyes water as he toyed with his large cock as it stiffened at the prospect of a new sissy. Emma sniffed at the manly scent of his bulbous and sticky bell end, as he put his hand behind her head. The domme watched intently sneering and excited.
“You lick it nicely first little sissy. I want you to savour the taste of a real man; you’ll swallow his seed too; every last drop.” Poor Emma licked at the hardening bell end, making Kurt shudder and gasp with pleasure. This was truly a sweet sissy and he would enjoy training and breaking her. Emma trembled with fear and was so ashamed when the domme pointed out her stiff and erect sissy cock.
“Oh what a dear little sissy you are going to be; I think you know your place already!” Kurt pushed his stiff cock between Emma’s sweet lips, into the hot softness of her mouth. She gagged a little as the large veined cock probed back and forth. Emma cried sweet tears and dribbled as Kurt applied his urgent member relentlessly. Emma’s bottom tingled and her sissy cock pulsed as she was used for the first time. Her tears pleased Kurt, and his cock soon buzzed with erotic pleasure. His balls tightened as he looked down in ecstasy at the sweet sissy that was now his. Emma now sucked on the large cock lovingly; she was truly beginning to know her place, her anus tingled tightened as Kurt moaned in ecstasy and shot his first globule of hot semen. He held Emma’s head firm as he delivered; there was no escape for her. Emma gagged a little more as she gulped and swallowed the hot salty cum. Kurt roared and spent again and again, his white cream dribbled down Emma’s chin as she struggled to swallow it all. Sated, Kurt pulled his glistening cock from the sissy’s mouth; cum dribbled from the end of his cock. The domme slapped Emma.
“Lick that cock clean, I’ll have no mess!” Kurt smiled as Emma’s tongue lapped delicately at the dribbling salty morsel from his still firm bell-end. She yelped as the domme whipped her sweet little arse with a cane, just for good measure. Kurt laughed and wiped the dribble of cum from Emma’s chin with a finger, then had her lick that clean too. Kurt was more than pleased.
“Well done Elaine! This one will make a very sweet sissy indeed. She’ll have the full treatment as soon as possible; I can’t wait to see her in a few months, her pussy will be very inviting when she’s ready.” Kurt left the room and Elaine took Emma to the wash rooms to prepare her for her first treatments. The wash rooms were immense, including a Turkish bath area. Emma was handed to two dominant looking young females who bathed her and powdered her dry. Under Elaine’s supervision she was taken to a room and laid on a soft bed. The giggling girls lifted Emma’s sissy cock and balls, creamed them and shaved off every last bit of hair; her legs were given the same treatment. One of the girls smiled wickedly as she picked up a pot of cream; Elaine and the other girl held poor Emma down as the cream was applied to her sissy cock and balls, chest, arms and legs. Emma writhed in pain as the cream stung like hell, especially around her sissy balls, making her cry like a baby, much to the delight of the females. The cream would ensure that no hair grew back for some considerable time.
The pain subsided and the girls dabbed away Emma’s tears. Elaine took five tablets from a huge apothecary jar and made Emma swallow them.
“You’ll have these twice a day for the next three months. You’ll see the benefit of them quite quickly. You are going to be such a pretty sissy.” Emma had no idea what the tablets were, she was in no state to refuse them. She was then taken to her bed chamber. Elaine looked very stern as she pulled three items from a drawer; one was a large blue tablet which Emma was made to swallow. The second was a tiny cock cage. Emma whimpered as the girls looked on delightedly as her hairless white sissy cock was caged.
“We’ll have no masturbating, except to order. You’ll cum when I say so and at no other time.” Elaine smiled wickedly as she showed the sissy the other object. It was a vicious looking butt plug.
“This will prepare your bottom for its future service; you will learn to enjoy the feeling. Poor Emma was held down and cried like a baby again as the plug and her anus were greased; the plug squeezed home by her dominant mistress. Emma sobbed as her tight little anus clenched at the spiteful plug. Her sissy cock stiffened as best it could in the cage. The invading plug teased her bottom sweetly; she was truly well on her way to sissyhood now.
Emma awoke in the softness of her silk sheets and wondered what the day would bring; her sissy cock bulged and dribbled sticky pre-cum through the outlet of her cage as she thought of sucking Kurt’s cock; her tight little anus clenched and released at the plug, which acted like a comforter. Elaine was right, Emma was beginning to enjoy the plug and as she tried to rub her confined cock, she imagined the plug to be Kurt’s cock; how she wanted to cum! The blue pill she had been given would keep her little cock hard in the cage and make her yearn to orgasm. This would make her extra obedient and willing to please in any way; her submissive side was taking control of her, as much as Elaine was. She quivered with fear and anticipation as Elaine and one of the dominant maids came in.
Emma’s anus tingled excitedly as she was made to kneel in a corner whilst the haughty Elaine inspected her bed-sheets. Elaine made sure the sissy had a good view of her buxom behind as she bent over, legs and seams rigidly straight, wicked cane under one arm. The dominant maid smiled wickedly and pointed to a small patch on the sheets.
“What’s this? You naughty girl, you’ve messed on the sheets. Come and lie face down on the bed this instance. You shall have a thrashing before breakfast.” Emma did as she was told and lay prostrate on the bed. The maid lifted the sissy’s middle and a pillow was pushed under her, lifting her sweet white cheeks invitingly, ready for the wicked bite of the cane. Before Emma could think, she heard the whoosh of the rattan and squealed with pain as her white cheeks blushed a pink and then red line across her sissy bottom. Again, Emma cried like a baby as the fiercely dominant woman delivered the stinging cane six times; oh how it hurt, and how she wanted to cum now, her sissy cock ready to explode. Elaine had Emma kneel and kiss her feet whilst she thanked her for the caning, and then the tearful sissy was taken to the wash-room by the smiling and contented maid.
Washed and fed, her pills taken, Emma was led into a large room where Elaine awaited her. The room was ringed with seats which were occupied by many males, some business suited, others casually dressed, all wore masks, some simple, some distinctly sinister. The centre of the room was furnished with large futons on which maids lay casually. Emma was naked except for the chiffon negligee and a hubbub of approval reverberated from the watching males as the increasingly dainty sissy was walked to her beckoning mistress.
Elaine showed the sissy a mean but pretty corset which was wrapped around Emma’s white hairless body as she knelt before her mistress and a maid. The laces were threaded through and Elaine took great pleasure in putting her foot in Emma’s back as she pulled the corset tighter and tighter. Emma fought for breath as the corset squeezed her waist to a tiny width. The effect of the corset also accentuated her sweet bottom, making her look even more girly. At the top end, any spare soft flesh was pushed up, giving the effect of small breasts. Emma was then collared and leashed and paraded round in a circle before the males, some of whom masturbated openly as they viewed the sissy.
One of the males waved a wad of notes at Elaine, who then invited him into the centre of the room as the others cheered and applauded. Emma was made to kneel before him; he dropped his trousers and pants, revealing an erect cock. Elaine stood close with her cane and Emma tingled all over as she sucked cock for the second day in succession. The male was not teasing like Kurt, and soon came as Emma’s soft lips and warm tongue massaged the aching bell-end. He grunted and shuddered as the pretty corseted sissy kneeled submissively and gently sucked the cream from him. He stroked her soft face and had a squeeze of her soft bottom before re-joining the circle.
The murmurs continued amongst the males as the maid painted Emma’s finger and toe-nails sissy pink, before applying make-up to her soft little face. A long flowing wig of a similar hair colour was produced and fitted. Elaine smiled triumphantly as she wheeled a full length mirror up to the sissy and had her look at her reflection. Emma gasped as she saw herself for the first time; the first part of her transformation had been achieved, she was truly effeminate now. She was still admiring her curves when a cheer went up from the males. Kurt had entered the room, naked. Elaine took a tiny key from a chain about her neck and undid the sissy’s cage. Emma was turned to face Kurt and their cocks rose in unison. Emma’s little bottom tingled as she thought of sucking that cock again. Kurt’s cock stiffened as he viewed the transformed sissy with disbelief; he would not have her suck him this time.
Emma’s little cock poked upright with excitement, her little pink bell-end glistening with lubrication. Kurt embraced her, put his hand down to the crack of her sweet cheeks, and eased the butt plug out from her anus. Every male in the audience now toyed with their stiff and excited cocks as they watched the spectacle unfold; a spectacle they had witnessed many times before. Emma gasped as she realised she was not to suck Kurt. Her anus, now free of the invading plug, clenched and opened with sweet anticipation. Kurt looked at the sissy as he first sniffed the plug, and then licked it clean. His large cock dribbled as he put his hand down the cleft of her buttocks, making her tremble as he eased a finger into her soft inviting arsehole. Emma clenched on the finger and her sissy cock buzzed and pulsed as Kurt smiled wickedly at her. He was going to fuck her.
Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Cornelius seemed to be the perfect person to help her in completely feminizing and sissifying her live in sissy, Sindy.
She already had Sindy living in 24/7 sissification, always wearing nothing but female clothes, finger and toenails painted; ears , tongue and nipples pierced; female tan lines; constantly in chastity; speaking in feminine voice and lisp; fully hairless from the eyebrows down from laser hair removal; eyebrows plucked into a thin arch; a tattooed tramp stamp that said “sissy cumslut”; plugged daily with monstrous butt plugs; permanently tattooed lipstick, eyeliner, and eye shadow; collagen lip injections; received weekly hypnosis to reinforce sissy slut status; fucked multiple times per day with enormous strapons that would make any hooker cry; and a litany of daily exercises that were so humiliating that Sindy thought she would die from embarrassment. However, Lucy wanted to take it up a notch. She wanted Sindy to start female hormones and anti androgens, and Dr. Cornelius was part of her plan to help achieve this goal.
Through the course of her investigation, she followed Dr. Cornelius for months. She found out that in addition to being a top rated endocrinologist that specialized in helping transgendered patients transition into womanhood, he was also a bit of a deviant. He frequented BDSM clubs and gay clubs. She found out that he was not only bisexual, but was also a top notch Dominant in the BDSM community. This of course was not listed on his practice’s website, but she found this out through months of painstaking investigation.
Tonight, she watched him across the bar of the Blue Martini. She had already decided that tonight was the night, and she wanted to get to him before he took home one of those bar sluts she had seen him talking to over the course of the evening. Lucy was dressed in business suit, much like the happy hour crowd that was assembled. However, she had replaced the top with one much more revealing than for which the suit was originally designed. Her ample cleavage was on display—which was completely her goal since she had witnessed over the months that Dr. Cornelius was definitely a boob man. She made her way around the bar and chose a stool about 4 down from the doctor. She had just caught the bartender’s attention and was ordering a Stoli on the rocks with a splash of cranberry when she felt his presence in the stool next to her.
“Hey there, I don’t think I recall ever seeing you in here before.” He said.
“I come in here occasionally. I don’t live far from here.” She replied.
They exchanged the typical bar pleasantries, talking about jobs, other people at the bar, etc. for the next 25 minutes or so. Both were very good with the light sexual innuendo. Every time she vaguely referenced sex, he gave it back to her as good as she gave. After they had finished their third drink, their inhibitions were down and the light sexual innuendo turned to that much less thinly veiled.
“Can I ask you a question?” Lucy asked.
“9 ½ inches.” Was his response.
“Well, that isn’t what I was going to ask, but that is certainly useful information.” She replied with a gleam in her eye. She had heard this response before in her life, so it didn’t catch her totally off guard.
“Do you think you can handle it?”
“Oh, I can handle it. I just don’t think you can handle me.” She said.
“Why do you say that?” he asked.
“I enjoy some of the more non-traditional things in life.” She said.
“Well, now you have me intrigued. Do tell.”
“I wouldn’t want to scare you off.” She said as she laughed.
He laughed back.
“There isn’t anything you could tell me that would scare me off. I have probably done far worse than you could ever dream of.” He said.
“I doubt that. But let’s hear something that you think would scare me.” She said. She was enjoying this game of cat and mouse, one that she never lost.
“Well, I do enjoy an occasional foray into BDSM. ” he said.
“I take it from your forward personality that you are a dominant?”
“How did you ever guess?” he asked.
“It takes one to know one.” She laughed.
“You are a dominant as well? You look so innocent. Are you into the Orlando BDSM scene?”
“I haven’t ventured into the scene much..yet. I have a live in submissive that I want to expose to it.” She said.
“Oh really? Male or female sub?” he asked.
“Somewhere in between.” She replied.
“You have a transgendered sub?” He asked.
“Well, that isn’t 100 percent accurate. He started out as my boyfriend. When we started experimenting with BDSM, he was just my male sub. Over time, I developed a taste for forced feminization. Now he lives as my sissy full time. I am feminizing him a little more each day, and there is hardly any male left. He, or should I say she, is in chastity all of the time now.”
“Have you started her on hormones yet?” he asked.
“Not the real ones. But she knows it is coming. She has taken about 5 months of my birth control pills in addition to herbal estrogen for about a year. The pharmaceutical hormones are the next step in her feminization.”
“You can get some results with herbals, but they are nothing compared to the results you can get with pharmaceutical grade hormones.” He said.
“And you know this from experience?” she asked, feigning ignorance.
“Well, for one thing it is my job. I am an endocrinologist. For another thing, I have taken a special interest in sissies and males transitioning to females. The ones that are forcibly feminized are of particular interest to me. I have trained a few sissies in my time and could assist you with her training.” He said.
“Oh, well, you definitely should meet Sindy then. She is definitely being forced further than she ever thought she would go. I have just done it a little at a time, where now this is just normal for her. I doubt she would even recognize herself or how far she has come in the last three years. And I would take any assistance that you could offer in helping her to be a better sissy.”
“That sounds fantastic. I would love to meet her and help you with her training. The hormones are a necessity though. I have found that they truly help a sissy realize their true nature and they realize there is no chance of ever going back to their male life. There is nothing quite like the thrill of injecting the first dose of hormones into a reluctant sissy.”
“That could certainly be arranged. How about tonight? I love to make her blow random men. She has really gotten to be quite the accomplished cumslut.” she said with a smile.
“She sounds perfect. Let’s get out of here. I’ll follow you.” He replied peeling off a wad of twenties and throwing them on the bar.
Lucy was excited. She had known Dr. Cornelius was into the wilder side of life, but she had no idea that he had trained sissies before. This was turning out far better than she could have ever imagined!
She drove slowly to her house so that Dr. Cornelius could easily follow her. She pulled into her parking spot at the house and Dr. Cornelius parked next to her. She could see him pull out a bag from his car and they walked to the door of the house. She unlocked the door and went inside as Dr. Cornelius followed her up the stairs.
Once they reached the top of the stairs, they could see Sindy sitting at the desk behind the computer. She was wearing a very sheer, pink ruffled nightgown, pink thigh highs, sheer pink panties, and pink stiletto heels. The shelf bra in the nightgown was struggling to contain the massive EEE false breasts inside. Her bleached blonde hair was styled in pig tails and her permanent eye liner was accentuated with coral pink eyeshadow. Her permanent lip liner was touched up with coral pink lipstick and lipgloss, which looked very nice on her plump, collagen induced lips. Her cheeks were also colored in pink blush. She had a deep tan, which contrasted nicely with the pink nightgown. The pale white skin from her bikini top tanlines was a stark contrast to the dark tan she had.
On the computer screen was a video playing of a large, muscular, hairy man with both of his ample fists buried inside of a sissy’s ass. The sissy’s screams coming from the computer were permeating the room. Sindy looked up from the computer screen to see Dr. Cornelius and Lucy—and although she didn’t look surprised to see a man standing there, it was obvious that she was highly embarrassed. Her pink cheeks immediately filled with more color. One of the aspects of her sissy hypnosis training was that she would always be extremely aroused when in the presence of real men and when forced to perform deviant sexual acts on them, but would also be extremely humiliated and embarrassed by being forced to do so.
“Sindy, I would like you to meet Dr. Cornelius. He has offered to assist me in your sissification training. Come over here and meet him.” Lucy announced.
Sindy stood up from the computer desk and walked very daintily over to Dr. Cornelius. Her CB3000 was very visible through her sheer pink panties as she minced over in very small steps, careful not to topple over from the very ample and very heavy breast forms in her nightgown and the ultra high stiletto heels.
“I am very pleathed to meet you.” She said in a very breathy, very sissyish voice as she extended her right hand to Dr. Cornelius with the wrist bent.
He took her hand and gently kissed the back of it, noticing the perfectly manicured one inch nail extensions, in coral pink with a French manicure.
“The pleasure is all mine.” He said.
“Sindy, why don’t you fix us some drinks? The usual for me. Dr. Cornelius, what will you have?” Lucy said.
“Scotch on the rocks, please.”
“Sindy, you can make yourself an appletini. Dr. Cornelius, why don’t we get more comfortable on the couch?” Lucy said.
Lucy and Dr. Cornelius sat on the couch as Sindy minced over to the bar to make the drinks. Dr. Cornelius noticed the massive butt plug inserted in Sindy’s ass through the sheer panties.
“Do you always let your sissy watch porn when you are away?” Dr. Cornelius asked.
“Well, I don’t let her. I require it. She is required to watch at least two hours per day during the weekdays, and three hours per day on the weekends. I pick the genre and she has to find a certain number of videos per day of something she thinks I will find hot in that genre. If I don’t think what she has sourced hot enough, she gets punished. I have found that it makes her chastity much more unbearable. Additionally, I bring her to the edge of orgasm over and over again for a minimum of 45 minutes per day, never letting her cum. She hasn’t cum in over three months now. She gets punished if she fails and accidentally cums.”
Sindy returned with a tray of drinks and was clearly embarrassed by the subject matter being discussed. She gave Lucy and Dr. Cornelius their drinks.
“Sindy, please show Dr. Cornelius what your punishment was the last time you failed during an edging session.”
Sindy placed her appletini on the coffee table and turned around. She lifted her sheer pink nightgown and slipped her manicured fingernails into the strings on the side of her sheer pink panties. She slowly lowered them as she bent over. Her tramp stamp, which read “Sissy Cumslut” in ¾ inch hot pink cursive letters became visible to Dr. Cornelius.
“Excellent work, Lucy! That is so hot. May I?” Dr. Cornelius said as he reached towards Sindy’s ass.
“Absolutely. Be my guest.” Said Lucy.
Dr. Cornelius rubbed his hand across Sindy’s tramp stamp, and lowered her panties even more. He was caressing each of her ass cheeks and his hand made its way to the monstrous plug in her ass. He felt the vibrations coming from the plug as he pushed it deeper in Sindy’s ass. He could hear Sindy moan loudly as he did so.
“This little slut loves to be filled, doesn’t she?” he asked.
“Oh yes. You should see some of the dildoes I fuck her with. She also loves to be fisted. She loves having her hole filled because that and her sensitive nipples are currently her only form of pleasure she is allowed. The last time we got to the three month point, I think she would have fucked a horse if I had let her, just to try and get off. Between the three months in chastity, the daily edging, and the constant porn watching, she was a sobbing wreck begging to cum daily.”
“Well, you wait until you start her on the real hormones. Her nipples will become even more electric and she will go through the roof when you touch them, much less when you put nipple clamps on them.” Dr. Cornelius said, all the while pushing the plug deeper into Sindy and letting it slide out a little each time. Sindy was pushing back onto the plug, just short of bucking wildly at this point. Her groans were becoming more insistent.
“Sindy, stop being such a slut and go get Dr. Cornelius and I another drink.” Lucy said.
“Please call me Bob. The slut can call me Master.” Dr. Cornelius said.
Sindy pulled her panties back up and minced her way over to the bar with their empty glasses. She was getting worried because she could tell they had already had an ample amount to drink before they got here. Lucy was always more strict and dominant when she had been drinking. The tramp stamp on Sindy’s back had been as a result of one of those evenings. And this guy she brought home seemed to be even encouraging her more—he kept mentioning hormones! Sindy was worried, but also aroused. She felt a big glob of precum slide out of her CB3000. She took a napkin from the bar and tried to clean it up before they saw that this was arousing her.
“Stop playing with yourself and bring us our damn drinks! And they better not be as weak as they were last time. Put some damn liquor in them this time!” Lucy yelled.
“Once you start them on hormones, they stop trying to play with themselves so much.” Dr. Cornelius said.
Sindy heard this and trembled, but she knew she better get the drinks to them soon or risk Lucy’s ire.
“Well, Bob, that is precisely my intention. I just need to obtain a supply and I will get them started as soon as possible.” Lucy said.
“What if I told you it was possible right now?” he asked.
“I would say bring it on. And you would certainly have free use of her any time you desired for your troubles.” Lucy replied.
“Well, I have developed something in my practice that is not quite FDA approved just yet. It is a device similar to the Norplant birth control device. It slides in right under the skin. I can have it done in just a few minutes. It time releases estradiol, finasteride, and spironolactone daily. 10 days of the month it adds progestin into the mix. What do you think?” he asked.
“Let’s do it.” She said.
“I need you to be 100 percent sure. This particular device lasts 3 years. Once it is in for about a month, the effects are really irreversible. These are not your typical hormones, they are much more potent than what you can get from other doctors.” He stated.
“Oh, I am very sure. I have been wanting this for a very long time, and it is just lucky that I met you. Sindy has known for some time that I was going to put her on real hormones. She just maybe didn’t know that it would be this soon. When would be the earliest that you could do it?”
“I can do it right now. But I would like to test out her mouth first, if that is ok with you.” He said this as Sindy walked over with the drinks. It seemed like her cheeks had constantly been red since this man walked into the house.
“Sindy, please help Bob take his clothes off.” Lucy said.
Bob stood up, threw back the drink of scotch and waited for Sindy to put the other drinks down. He stood there as she helped him take his shirt off. He was actually in very good shape, and had an extremely hairy chest.
“What are your thoughts on kissing sissies, Bob?” Lucy asked.
“I love it. It is really good foreplay.” Said Bob.
“Well, Sindy does not like it at all. But I make her do it to show her who is in charge. Why don’t you give her a kiss or two?” Lucy asked.
Bob pulled Sindy’s head towards him and shoved his tongue in Sindy’s mouth. He could tell from her body language that she did not like it. He could feel her tongue piercing with his tongue and thought that it was going to feel very good on his cock in a short amount of time.
“Sindy, run your fingers through the hair on his chest as you kiss him. If you don’t start showing some enthusiasm, things are going to get very bad for you.” Lucy said.
Sindy could hear in Lucy’s voice that she was getting drunker and drunker and knew that she better obey. It was hard to concentrate, because Bob was pushing the plug in and out of her as his tongue explored her mouth. Her manicured hands roamed Bob’s hairy chest.
“See, Sindy. That is what a real man’s chest looks like. Not your hairless body. You never really were much of a man anyway though. I always knew you were a sissy. Now, work your way down his chest with your mouth. I want you to pay particular attention to his nipples.” Lucy said.
Sindy moved her way down, at least happy that she didn’t have to kiss Bob anymore. But the thought of kissing and licking his hairy nipples was not that much more appetizing to her. She licked and sucked each one, not enjoying the massive amount of hair he had and the feeling of it on her tongue and in her mouth.
“This sissy is making me hot, Lucy.” Bob said.
“Well, let’s do something about that. Sindy, take Bob’s pants down and start working on his cock.” Lucy said.
Sindy unbuttoned Bob’s pants and then unzipped them. She pulled them down along with his boxers and was greeted with a truly massive cock. It was only partially hard, and it was at least 8 ½ inches long. But the truly impressive thing was its girth. It was probably about 6 inches around and had a huge mushroom shaped head. Sindy had never seen one this big, and this thing wasn’t even completely hard yet.
“Generally, I like my sissies to lick my ass a bit before they blow me. Do you mind, Lucy?” Said Bob.
“Not at all. Sindy, let’s see how far you can get your tongue up Bob’s ass!” Lucy barked.
Sindy’s stomach turned over. This was by far the thing that she was dreading the most. She made her way under Bob’s balls, licking them and gently sucking until her tongue was at his ass. It was as hairy as his chest, if not hairier. She tried to think of something else as she started licking.
“Very nice, sissy. Now do as your mistress says and work your tongue in deeper.” Bob said.
Sindy did so as Lucy watched. The further Sindy stuck her tongue up Bob’s ass, the harder his cock got. Lucy was watching as his impressive cock grew to full mast. It was at least 9 ½ inches long.
“Well, he wasn’t lying about that part.” Lucy thought.
“Now, sissy, work your way back to my balls.” Bob ordered.
Sindy was tonguing his balls and his enormous cock was laying on her forehead. Meanwhile, Lucy had pulled up the skirt to her business suit and removed her panties. She began fingering herself uncontrollably.
“Now sissy, you get the reward. Beg me to suck my cock.” Bob said.
“Pleathe thir, can I thuck your matthive cock?” Sindy said seductively, the giant ball in her tongue causing her to lisp dramatically.
“Of course. I am glad you asked. But we are going to need to work on your begging skills.”
Sindy dove right into her work. She definitely wanted to show enthusiasm to this task so that she didn’t have to go back to tonguing his hairy ass. She licked all the way up the enormous shaft, coming to the giant mushroom head. She greedily licked the large drop of precum that had formed at the tip. She played with this in her mouth a bit for show, and then licked all around the top of the head. She slowly took the top of the head in her mouth and applied gentle suction.
“Stop teasing it and get to sucking, you fucking whore. Wrap those giant dicksucking lips around my cock.” He said to Sindy.
Sindy took this as her cue to get to work. She took his entire shaft down her throat. Lucy had been teaching her to deep throat for the last year or so with bigger and bigger dildoes. She could successfully deep throat a 10 inch dildo, but it wasn’t as thick as Master’s cock. She felt a little pride as her nose hit his stomach that she had taken all of him. She let her tongue go out of the bottom of her mouth and lick his balls. She heard Lucy orgasm violently as she did this and could see out of her peripheral vision that Lucy continued to finger herself, going for another one. Sindy pulled her head almost all the way off of Master’s cock, just leaving the head in her mouth. Then she went all the way back down to the hilt again. She heard Master moan, and she knew that he must like it. She continued her assault on his cock, varying up her suction, speed, and even twisting her mouth some as she went up and down. Her manicured fingers were gently caressing his balls, occasionally one of her fingers roamed to tickle his ass. He was really getting into it and his cock was amazingly hard. Master grabbed her pigtails and started fucking her face. He would push his cock all the way down her throat and then pull it almost all the way out. Then he would ram it forward, back down her throat. He was picking up the pace and really fucking her face hard now. She knew he was close, and could taste more and more precum with every thrust.
“Are you ready to take your Master’s cum, you slut?” he asked.
Sindy couldn’t say much with a giant cock being rammed down her throat violently. And besides, she had always been taught not to talk with her mouth full. She heard Lucy orgasm again, this time even louder.
Master was really fucking her face hard now. He had a death grip on her pigtails, and she couldn’t move off his cock, even if she wanted to. He pulled her all the way down on his cock as she felt the first blast of his cum shoot down her throat. He pulled back a little, so that his cock was not buried in her throat and she felt the second, third, and fourth blast of his cum on her tongue. Then he pulled out of her mouth entirely and shot the remaining two blasts onto her face.
“You better swallow all of that, you fucking cunt.” Master said.
Sindy showed him the cum in her mouth by sticking out her pierced tongue. There was definitely a mouthful there. Then she closed her mouth and swallowed it all, opening it back up to show Master that she had indeed followed his orders. Lucy had gotten off the couch and was standing next to her. Lucy scooped the copious amounts of cum off of Sindy’s face with her fingers and told her to lick them clean. Sindy greedily did so, sucking Lucy’s cum covered fingers with abandon. Soon, all the cum was off of her face.
“Now, lick his cock clean, you slut.” Lucy said.
Sindy leaned forward and gently licked and sucked every inch of Master’s sensitive cock clean.
“Look at her little sissy clit, Bob. It is trying its best to get hard in the cage. She must really love sucking your cock.” Lucy said.
Sindy didn’t think it was her place to say that her little sissy clit attempted to get hard when the wind blows these days. After being in chastity for three months, constant porn viewing, daily edging, and being plugged almost 24/7, what did she expect? But she kept quiet, as she knew it would be futile to argue.
“Well, she is going to be getting a lot of it. That is one hot sissy you have there. We will fix the sissy clit in a few moments so that it won’t be trying to get hard again. Once I am done tonight, that thing will be a useless piece of flesh in less than three months. Then she will be 100 percent sissy. I take it that you have a bondage bench somewhere in here?” Bob said.
“Yes, of course. I have to strap her down every day when I edge her. I don’t want her getting any ideas when I take the chastity device off of her.” Lucy said.
“Well, go get her strapped in, and I will make us more drinks.” Bob said.
Lucy led Sindy into their bondage room. She saw Sindy about to say something and cut her off.
“Not a word. I have been telling you this was coming for a long time, and you thought I was bluffing. As you can clearly see now, I am not.” Lucy said sternly.
Sindy was clearly scared now, but also very aroused. She had always been very much turned on when Lucy talked about hormones, but this just seemed so sudden. She laid back on the bench and put her legs up in the stirrups. Lucy proceeded to strap her legs and feet into them, and then moved up to her arms. Once her arms were secured, Lucy pulled the strap across her chest and buckled it, and then ran a strap across her stomach and buckled it. She was now completely helpless, and in the position she always was when Lucy edged her.
“I don’t want to hear one word out of you, or else I will use the biggest ball gag we have. You know the one, you always complain about how badly it hurts your jaw when I use it.” Lucy said.
Dr. Cornelius walked into the room carrying the drinks and his bag.
“Here’s your drink Lucy. Here’s to a long lasting friendship.” He said as he raised his glass in toast.
As they clinked their glasses together, Sindy felt as if her fate was sealed. She was petrified, but her sissy clit was betraying her. It was as hard as it could get in the CB3000. Lucy came over with the key and took the CB3000 off of her. Sindy’s sissy clit stood at full attention now.
“Well, I can see why you sissified her. There really isn’t much there anyway. I can’t imagine that this little thing ever satisfied you in the first place.” Bob said as he fondled Sindy’s sissy clit.
Sindy almost came off the table when he touched her extremely sensitive clit. She wanted to cum so badly. Maybe if I behave, they will let me cum, Sindy thought.
“Do you have somewhere I can wash up before we get started? Let me just lay out what I will need here.” Bob said as he laid out a surgical pad on the table near Sindy’s feet. This was followed by several instruments placed on top.
“Sure thing. Let me show you the bathroom.” Lucy said as they both left the room.
A few minutes later, they both entered the room. Bob had on surgical gloves and Lucy was finishing her drink.
“Ok, Sindy. This will only take a few moments and then we will be all done. You will be on your way to being a true sissy.” Bob said.
Bob pulled out some alcohol wipes and began swabbing down Sindy’s ass at the incision point. Sindy’s legs were high in the air, and she couldn’t move a muscle. She had never felt more vulnerable. Meanwhile, Lucy was busy fondling her sissy clit—which was as hard as a rock. She began to slowly stroke Sindy’s clit up and down. It didn’t take long before Sindy was about to explode. Lucy stopped all stimulation.
“Now, I am just going to give you a light local anesthesia so that you won’t feel a thing.” Bob said as Sindy felt the needle go into her right buttocks.
Lucy had resumed stroking Sindy’s sissy clit and was talking dirty to her.
“Don’t tell me you don’t love this, you fucking whore. Your little clit has never been harder.”
Sindy was almost to the point of exploding again, and again Lucy stopped stroking her. Sindy could feel her right buttocks going numb.
“While we wait for the anesthesia to fully take effect, I think Sindy should provide a little oral service to me just to pass the time. Lucy, could you help me take my cock out of my boxers? I don’t want to ruin our sterile environment.” Bob said as he laughed.
Lucy pulled Bob’s cock out of his boxers and placed it in Sindy’s mouth. Bob began fucking her mouth in earnest as Lucy resumed the torment on Sindy’s cock. Lucy edged Sindy to the point of orgasm another 15 times before she heard Bob announce that he was cumming down this slut’s throat. Lucy couldn’t remember the last time she had been this aroused. She could literally feel her juices running down her thighs. She helped Bob put his cock back into his boxers as he walked back towards Sindy’s feet. Lucy could feel Sindy trembling from being so aroused and went back to work on stroking Sindy’s sissy clit. Meanwhile, Bob had picked up his scalpel and the small plastic hormone device and was sterilizing them both.
“This will only take a few more seconds, Sindy. Then you will be on the way to permanent sissyhood.” Bob said.
Bob made a very small incision in Sindy’s right buttocks and slowly inserted the plastic device into the incision. Once the device was all the way in, he cleaned the incision point again with alcohol and closed the small cut with Dermabond. He then placed a bandage over the cut. Lastly, he pulled out another syringe filled with liquid, wiped down Sindy’s bottom with alcohol again, and injected the liquid into her buttocks. He then declared that he was done. Lucy had been edging Sindy through the entire procedure and she had managed to drive Sindy crazy for another 4 edges. Sindy was shaking in frustration.
“All done now, Sindy. The plastic device inside her will release the maintenance dosages daily. I just gave her a massive dose of the cocktail to get her started on the right foot. She may feel some nausea and cramping tonight and tomorrow morning, similar to a pregnant woman’s morning sickness from all of the hormones that will be raging around inside her, but that will pass with time. You can discontinue the use of the herbals, because she certainly won’t be needing them anymore. ” Bob proclaimed.
“That is excellent news, Bob!” Lucy said.
“When can I use this sissy’s cunt?” Bob asked Lucy.
“No time like the present. But for now I need to cum, so her mouth is going to be occupied for a bit.” Lucy said as she laughed.
Lucy straddled Sindy’s face and started grinding her soaked pussy onto Sindy’s tongue. Meanwhile, Bob had retrieved the can of Crisco and was lubing his hands thoroughly. Lucy immediately reached her first orgasm, and it was so strong that she squirted a huge stream of cum into Sindy’s mouth. Bob had removed the enormous plug from Sindy’s ass and was probing it with three fingers, then four. Then he had his fist inside Sindy. Lucy was coming down from an extremely intense orgasm, but seeing Bob’s fist in Sindy’s sissy pussy got her going again almost immediately. She ground her pussy back into Sindy’s face.
She saw Bob begin to work the fingers from his other hand into Sindy’s ass alongside his fist. She had gotten two fists into Sindy before, but it took a long time and it almost sent Sindy through the roof. Bob’s hands were almost twice the size of Lucy’s and she could feel Sindy start to shake again. At this point, Bob had one fist and four fingers from his other hand inside Sindy. Lucy was so turned on that she came again. Her orgasms were coming in waves from all the excitement. Bob was trying his best to get both hands inside Sindy, and Sindy was moaning uncontrollably onto Lucy’s clit. When Lucy saw Bob’s other wrist buried in Sindy’s ass, she couldn’t believe it. Sindy’s sissy clit was leaking fluid like crazy and a medium sized puddle had formed on her stomach. Bob was working both fists in and out, and it was milking the sissy cream out of Sindy. This sight (and Sindy’s talented tongue) caused Lucy to orgasm yet again. After about 10 more minutes of this, and 5 or 6 more orgasms for Lucy, Bob announced that he thought that was all the milk he thought he could get out of the sissy. There was a large puddle of cum on Sindy’s stomach. Sindy had been milked before, and while it felt good, she still had a desperate need to cum.
“Why don’t you feed that to her while I go wash up?” Bob said to Lucy.
“Excellent idea.” Lucy said as she got off of Sindy’s face. Lucy picked up a spoon from her bondage kit and began spoon feeding Sindy’s sissy cum into Sindy’s mouth. Sindy gobbled it up greedily and swallowed every drop. Sindy was so aroused from the whole scenario that her sissy clit never went soft the entire time.
Bob came back in the room and asked where the condoms were. Lucy threw him one from her kit and he put it on his cock, which had remained rock hard the entire time.
“Do you have another one? This hot little slut has me really worked up, and I want to put two on so that I can fuck her longer. I don’t want to cum too fast and ruin the moment.” Bob said.
Lucy threw him another condom and said, “You can certainly fuck her as long as you want, but remember that you will always be welcome to fuck her anytime you like. And your friends too.” Lucy said.
Bob put on the second condom and positioned himself at Sindy’s sissy pussy. He rammed his cock all the way in, none too gently. Sindy squealed, as she was very sensitive from the double fisting already. Bob did not hold back and fucked her with abandon. This, of course, got Lucy aroused again and she climbed back onto Sindy’s face and started grinding again. She reached down and began teasing Sindy’s sissy clit again as Bob fucked her harder and harder. Lucy had lost count of how many times she had cum already, but she managed to cum again another 5 times and edge Sindy another 10 times. Lucy got off of the table and just watched Bob plow Sindy like a wild animal. He had been fucking her for a good 20 minutes or so at this point, when he pulled out. He walked to the head of the table and pulled off both condoms.
“I think all sluts should always taste their Master’s seed. It is just wasted if it is shot into a condom.”Bob said.
“I agree.” Said Lucy.
Bob was ramming his huge cock down Sindy’s throat again and groaned loudly as he shot his load into her mouth.
“Don’t swallow it yet, you whore. Show it to me.” He said.
Sindy opened her mouth and showed Bob the massive load that was in her mouth.
“Swish it around like you would mouthwash. That is a taste you are going to become all too familiar with.” He said.
Sindy swished the cum in her mouth for 15 seconds before Bob told her to swallow it down.
“I think we are done here, for tonight.” Bob said.
“Yes, I think you are right.” Lucy replied.
Lucy went to the small freezer in the bondage room and took out the item that she knew Sindy dreaded most. The ice pack. Sindy knew that if this came out, that she was not going to be allowed to cum, and was going back into the chastity device. Lucy smiled an evil smile at Sindy as she placed the ice pack on her swollen sissy clit. Bob watched and laughed as Lucy held the bag and Sindy squirmed on the table as much as the bonds would allow. After 2 minutes of this treatment, Sindy’s sissy clit had run back into her body like a frightened turtle.
“Bob, would you mind handing me that CB3000 on the table over there?”
“No problem.” He said as he handed it to her.
She slid the chastity device onto Sindy’s shriveled clit easily.
Bob leaned over Sindy and said, “Just think slut, in about a month, you will have trouble getting that little sissy clit hard. And in three months, it won’t ever work again. It will just be a useless piece of flesh.”
Once the lock was in place on the chastity device, Lucy undid the straps holding Sindy in place and helped her up.
“Let’s get those breast forms off of her and take some before pictures of her breasts. That way, when my hormone device starts really working, we will have a basis for comparison.” Bob said.
“We can take them off so you can look at them, but there is no need for pictures. I have taken pictures of her every day in her transition and will continue to do so. It is for our website.” She said.
“You have a website?” Bob asked.
“Yes, it is www.sissificationofsindy.com I will give you a user name and password for free so that you can view her progress from male to what you see now. I think you will be amazed at the transition. We have lots of paying members, and sponsors—which is why Sindy doesn’t need to work anymore. There are lots of videos on there of me fucking her with a strapon, and her being gangbanged, her performing humiliating tasks in public, etc. Hopefully you and your friends can add some videos too, but the hormones are a home run.” she said.
“Excellent. I don’t know why I am just meeting you now. We could have had this slut way further along by now if I had met you earlier. But today is the first day of her new life!” he said as he was examining Sindy’s tender buds. From the herbal estrogen, she had a large A cup or a small B cup, and the doctor was impressed. He was rolling her pierced nipples around between his fingers and Sindy was moaning loudly. “These herbals you had her on were working far better than I would have imagined. Wait until you see the results from the pharmaceutical grade hormones we just put in her! I have some nipple stretchers we can put in these piercings too. We will have these nipples stretched to at least an inch so they will show through even the most padded bra.”
They exchanged phone numbers and email addresses. Lucy promised to email a user name and password to Bob and told him to begin preparing Sindy’s next adventure with his friends. Bob wholeheartedly agreed and said he would have a better idea of adventures for her after he had already seen how far along she was on the website. Then Bob said that he better be going because it was late and he had to work tomorrow.
He looked into Sindy’s eyes and said, “Bye for tonight slut. But I promise you will be seeing a lot more of me and my cock in the future.” With that, he grabbed her head and shoved his tongue down her throat. He made her kiss him goodbye for at least a minute before he let her head go.
“Thanks again Lucy. I will be in touch.” He said and turned and walked out the door.
“Well, that was certainly a successful meeting, wouldn’t you agree, Sindy?” Lucy asked.
Sindy nodded her head in agreement.
“Let’s go into the bedroom. All of this excitement has me wanting to cum again.” Lucy said.
Sindy followed Lucy into the bedroom.
“Get the strapon extension to your CB3000, cumbreath. I need something inside of me.”
Sindy retrieved the attachment to her CB3000 and was blushing from the name. It was a reminder of the three huge loads of real man semen and the large puddle of sissy cream she had swallowed that night. The device was 9 inches long, and thick. It attached to the end of her CB3000, which certainly gave her Mistress pleasure, while giving her none whatsoever.
When she had the extension attached, Lucy commanded her to her knees and told her to start licking. Sindy could not believe how wet she was. Lucy came almost immediately.
“Now put that cock inside me, slut. I want you to fuck me like your Master fucked you.” Lucy demanded.
Sindy put the tip of the large dildo at the entrance to Lucy’s pussy. She had planned to gently ease it in, to let Lucy get used to it, but it was not necessary. Lucy was so wet that it slid right in. Sindy began to rock back and forth, fucking Lucy with the strapon. She could feel nothing, but she could tell it was driving Lucy wild with lust.
“Fuck me harder, slut.” Lucy growled.
Sindy was really fucking Lucy hard now, pushing the cock all the way in to the hilt, then pulling almost all the way out and ramming it home again. She could tell that Lucy was cumming yet again, but she knew better than to stop until Lucy told her to. Lucy had meanwhile pulled Sindy’s bra down and was tugging sharply on Sindy’s nipple piercings and rolling her nipples with her fingers. Sindy was moaning loudly, as was Lucy. Lucy was cumming in waves now.
“Everything I have done to feminize you so far..Oh God, yes, right there…has turned me on so much…Oh damn, that’s it…But tonight has been the best so far…Don’t stop, you fucking whore…You are now a full fledged sissy bitch…oh yesssss…my sissy bitch…ahhhhhhh…to be used like I see fit…oh damn, there’s another one…with a now useless cock…oh my God, that’s the spot….and your tits growing bigger and bigger…yessssss…and when they stop growing from the hormones…oh, fuck that feels so good…I am going to give you implants so big that you can’t even see your feet…ohhhhh…more tattoos…more piercings…oh, shit…with Bob’s help, we are going to make you into the biggest sissy slut cum dumpster there ever has been…Oh, my God!
The phone rang. I rinsed the wine glass one last time and hung it on the rack. By the time I’d found a towel and dried my hands it had rung two more times. “Hello.”
“Is that you, Gene?”
“Yes. Who’s calling?”
A husky female voice responded, “Oh, Gene! Don’t you recognize my voice anymore?”
A jolt shot through me and I instinctively held my breath. I felt my face go pale and began to feel light-headed, so I sat back against the kitchen counter.
“Gene? Are you still there?”
“Yeah . . . yes, I’m here.” I said hesitantly, distracted by the dizziness, which was gradually easing.
“Ha, ha! Of course you are, honey!” Her smooth, deep voice resonated so many intense emotions in me – excitement, fear, confusion, desire – all at once. Her calling me ‘honey’ made it worse.
“So you still remember your Aunt Regina, hnnnnh? It’s been awhile, hasn’t it Gene?”
“Yes, quite a while.” I offered cautiously. My dizziness had abated, but the self assurance that had carried me through the day was all gone now – displaced by imbalance and insecurity.
“How long has it been, honey? I bet you know. Can you tell me how long?”
I knew exactly how long. “Three years . . . and a month.” The memories were still vivid.
“That sounds about right. So you do remember, don’t you?”
“Yes, what?” She sounded calm, but insistent.
“Yes, Ma’am?” I offered.
“No, no, no – not Ma’am. Try again. Yes, what?” It was her schoolmarm tone.
“Yes, I remember.” Damn, she already had me reciting in response. The memories of doing that flooded my thoughts. “I remember everything.”
“Good. That’s so sweet. Of course you do. You think of me often? Hnnnnnh?” Now in that lilting voice — encouraging, teasing.
“Every day.” It was true. A day hadn’t passed in which I didn’t think about her and remember what we did.
“What was that you said?” The schoolmarm again, “I didn’t hear you.” Her voice changes were herding me where she wanted. Even though I recognized what was happening, I felt compelled to follow.
“I think of you every day.”
“I think of you every day, Aunty Regina.”
“That’s better, sweetie. You do remember, don’t you? How Aunty Regina likes to hear you say it. All of it. Hnnnnh?”
“Yes, I remember.” The desire to please her was overwhelming.
“Have you missed me, honey?”
I didn’t know what to say. I’d agonized over her for months after she left. But that was a long time ago and I’d thought I was over her. Now, just hearing her voice had me in a tailspin.
“Yes . . . yes, I missed you . . . very much, Aunty Regina.”
“Well, I’m here, Gene. Here in town. I’m staying at the old place. I’ve leased it for the summer.”
I was speechless. Here? What did that mean? My life had become so normal compared to five years ago – with none of that perverse weirdness that had taken it over back then.
“You’ll have to come see me,” she stated flatly. I didn’t hear it as an invitation, or an order for that matter. Just a statement of fact: Yes, compelled by my own desire, I would have to see her. I started to feel pangs of the old urges.
“Um . . . OK.”
“No, I meant you’ll have to come see me.” OK, now it sounded more like an order, but one with which I was only too willing to comply. I wondered if she could sense that. I was afraid that she could but also wanted that.
“I could use your help getting the place in shape. Why don’t you come by tomorrow night, say around seven?”
“Um, . . . OK”
“And come prepared to do some chores. I imagine you still have appropriate attire — am I right?”
“Ha, ha, of course you do. I expected you would, honey. Just what I like — lovely. See you tomorrow.” Click.
It was a Friday and I didn’t want to think about it further that night. I opened a new bottle of Pinot Noir, poured myself a glass, and settled in to watch a movie. But anticipation rattled around in my unconscious.
The next day I got up early and went out for breakfast. I came home and took care of a few chores, paid some bills, and basically distracted myself as much as I could. Around 3 pm I couldn’t delay any longer and had to start to get ready.
First to the attic, where I keep several suitcases securely stowed away. I found the one I wanted, dragged it over to the attic ladder, and carefully hoisted it down. In the bedroom I removed the combination locks, then laid out the clothes I’d need for inspection. The uniform was unacceptably wrinkled so I did some ironing and packed it back up. Everything had to be perfect.
Then to the shower. I shaved my face three times. It had to be totally smooth, so there would be no possibility of snagging delicates or chaffing sensitive skin. It had been quite a while since I had shaved anywhere else. After she’d left, I did it every few months out of nostalgic pining. But not for a long time now – maybe nine months. I lathered up and spent the next half-hour meticulously shaving my legs, pubes, and balls. I always found the heightened sensitivity of the skin on my shaved legs to be exquisitely erotic.
I got dressed in my regular street clothes, packed up my case and headed out.
On the way there I reflected on how I had first met Regina, close to five years prior. It was while I was picking up an elective course in the summer between my Junior and Senior year at the university. I worked during the day and attended classes two nights a week. The other three nights I spent at a small research library in a quiet corner of the campus. It was seldom used – only two or three students were there on a given night – and staffed accordingly, by a single library studies grad student.
One evening, several weeks into the quarter, I saw a middle-aged woman sitting at the station where the grad student usually sat. Not thinking that much about it I sat down and got to studying. An hour later I was getting tired and starting to look around when I heard the clicking of footsteps.
The woman had come out from behind the counter and was rolling a cart full of books in my direction. As she approached I took real notice of her for the first time. She was older than the typical graduate student, probably in her early to mid-forties. Her bookish eyeglasses, and chin-length, dark brunette hair were stereotypical librarian. She wore a rather snug conservative grey skirt and white shirt that showed off a curvy pear-shaped figure – petite bust, narrow waist and broad hips. The sound I’d heard had come from three inch high heels, in a deep maroon color that nicely complemented her dark grey hose.
She was old enough to be my mother, but everything about her fascinated me. She seemed over-dressed, and both conservative and sexy at the same time. The snugness of her skirt was provocative. As she passed by I fixed my gaze on the roll of her ripe womanly bottom, then down her shapely calves, which tapered to elegantly thin ankles. The grey hose were too fine for everyday wear, but subtly so, and her heels were a statement – the maroon wasn’t garishly aggressive as a brighter red would have been but was assertive in a classy way.
For a while she was out of my sight shelving books and I returned to studying. When next I looked up she was ten feet in front of me directly across the aisle. She was facing away from me shelving the last of the books on the cart, which gave me a perfect view of her. God, she had a fine figure – such a small waist in contrast with her full, ample derriere. Voluptuous. Feminine, but womanly too. Soft on the outside, but solid on the inside. I couldn’t take my eyes off her.
As she reached up to put a book on the top shelf her skirt rode up a little and I got a glimpse of stocking tops. Holy shit, she was actually wearing stockings! Who does that anymore? None of the women I’d known even wore pantyhose. Gazing at her was like looking into some exotic cheesecake world – intriguing, sexy, dangerous, and intoxicating. I was so mesmerized that I didn’t notice that she had turned around. I flushed with embarrassment when I finally realized that she had caught me staring. She gracefully acted as though nothing had happened but I thought a saw a wry smile on her face as she walked away.
A week passed before I saw her again. When I did, I immediately remembered being caught before and felt embarrassed. She made her rounds again shelving books just like the first time I encounter her. I resolved not to embarrass myself by being caught again ogling her. But when she came around try as I might I couldn’t help myself.
This time she was wearing a red sweater, a smart white skirt, and 4″ black pumps. The thin fabric of the skirt snuggled tightly to her body, and accentuated her womanly figure. When she bent over to reach the lower shelves the smooth fabric was pulled so tight to her bottom that I could clearly see the outline of darker colored panties beneath and bumps from garter clasps. That’s when I noticed the dark seam that ran up the back of her beige stockings. An electric jolt of excitement shot through me. Once again, I was so mesmerized that despite my better intentions I’d fallen into a trancelike stupor.
She turned around and there I was, caught ogling away. This time she looked directly at me, all the while smiling a knowing, bemused, confident smile. Again, I was very embarrassed, only this time I felt much more exposed. She had an intense effect on me and seemed to enjoy knowing it. She also seemed to be amused by my embarrassment. As she walked away she had a distinct wiggle in her walk.
The following Wednesday, I was back at the library to study again. When I saw that the grad student that was usually at the front desk was back I felt a mixture of relief and disappointment. I settled into my routine and lost track of time.
I heard a noise and looked up to see her shelving books right to the side of me. I hadn’t noticed her arrival at the library or heard her approach. She was suddenly just there, which startled me. She wore a white cotton blouse, dark grey wool skirt, seamed black stockings and four inch heels. She was bending over to reach the lowest shelf. Not squatting, but bending over, way over, at the waist. The display of her legs and ass was intensely provocative. My blood pressure shot up and I immediately got hard. I had to stare. I could have looked at her like that forever and never tired of it. I wanted it to never end. My attention was so riveted that my peripheral vision had blurred and it seemed like I was looking through a tunnel at her ass. Out of nowhere, within three seconds, it had become the center of my universe. As if I was hypnotized.
She was still bent over when she turned her head to look at me. I was so far gone I couldn’t stop looking. She observed me like that for a while. It might have been thirty seconds, I can’t really say as my sense of time was so warped. I do know it was long enough to establish without a doubt that I was helplessly fixated. She slowly stood up and turned to look down at me. With a bemused smile she said, “I can see that you are one of those students that studies much harder than average. Keep that up and you just might make your dreams come true, sonny.” Then she winked at me, turned on her heel and was gone.
I was absolutely mortified. She was wildly tantalizing, it scared the hell out of me that I so easily lost control around her. It was especially embarrassing that she knew it. After that incident, I resolved to change where I sat in the library. I didn’t see her again for a while, and gradually became more at ease being in the library.
Two weeks later on a Friday I had been studying hard at the library since late afternoon and took a break to grab a quick bite at a coffee shop just off campus. Upon returning to my alcove I dove back into reading. A short time later I heard the sound of heels striking the terrazzo floor echoing off all the hard surfaces in the room. I looked up to see her walking towards me. As she got closer I realized she was coming to talk to me and I felt a little spasm of panic.
She sauntered up to my table, and stood there smiling with her weight on one leg and her hand on her hip.
“So there is someone here. I saw the books and was wondering — because no one had signed in.”
“Oh, I’m so sorry! I came in the afternoon and took a break to go eat. I forgot about signing the log.”
“That’s the rule, after six pm. Come with me, now.” She suddenly turned on her heel and walked away without waiting for a response. I scrambled to my feet and hurried to catch up. On the way I noticed that I was the only student studying in the library that evening.
I followed her to the front desk trailing the wiggling roll of her hips. She was wearing an accordion-pleated navy blue skirt that swished as she walked, complemented with nude seamed hose and black heels. At the front desk she stopped, paused for a moment, and then spun around, spinning her hem out. It sensed that she knew I’d been ogling her on the way to the desk and was giving me plenty of notice so I wouldn’t make an ass out of myself again. She tapped the log with a finger, said “Sign.”
As I was signing the log she sat in the desk chair, which was well away from the desk such that the view of her was unobscured. I could peripherally see her cross her legs and felt her looking at me. I put the pen down and slowly looked up. Her shapely legs caressed by the shiny stockings were magnificent. The light directly above her reflected off the gloss of the sheer nylon highlighting the length of her legs I didn’t want to stare but they were just so exquisite that I had to take them in for a little bit before I looked her in the eye.
When I did she was leaning back in the chair gently bouncing her foot and playing with the hem of her dress. She was looking right into me with a calm expression of determined intent. She so had my number. I was stuck in some kind of limbo – I couldn’t look her in the eye but I couldn’t look away either. It seemed natural to look at the floor and occasionally glance at her legs.
“What’s your name, honey?”
She toyed with her skirt, occasionally stopping to stroke and smooth her stockings, gradually letting the hem ride up until her stocking tops just showed. “You like that, Gene?”
I swallowed hard and squeaked out an “Uh, what?”
“You very well know what I mean, young man. I’d appreciate an honest answer, now.”
With a squeaky nervous voice, “Oh, um, OK. Well, yes, I like it. Very much. But I guess you already knew that.”
“Unh hunh.” She let the moment hang on that remark and pinned me with her stare. She didn’t have to say anything to make her point. Saying nothing said everything — the longer the silence went on, the more apparent the power dynamic became – it was obvious that I was smitten with her and she could do whatever she wanted with that. Two minutes is a long time to sink into the realization that this woman could own me. And I didn’t even know her name.
“I know you’ve been staring at me, Gene.”
“Um, I’m sorry, I didn’t mean to offend you or anything.”
“Oh, honey, that’s not a problem for me. Quite the contrary, I enjoy being admired. It just feels so good and so right – just lovely.”
“Well, uh, I think you’re. . . very attractive and I . . .”
She cut me off short, “How you feel is quite clear to me, honey. The real question is what we are going to do with it . . .” She toyed with her hem some more, gradually pulling it up to reveal a garter clip that had loosened. Standing, she grasped the stocking top with her fingers she pulled up on it while stretching out her leg and pointing her toe. After resetting the clip she swung her gaze up to see that I was completely mesmerized watching her, “. . . or perhaps I should say what you would be willing to do — for the privilege of admiring me, hmmmh?”
She stared hard at me. It was all I could do to return the eye contact. She had reached right into my core and touched something of great importance to me. I desperately wanted to be intimate with this woman.
“You are interested in admiring me, aren’t you Gene?”
I didn’t hesitate for a moment, “Yes.” I found everything about her to be wildly exciting – her figure, how she dressed, and especially how she spoke to me. She was exciting, and dangerously unpredictable.
“I like to look good, Gene. And I like that to be appreciated — truly appreciated. But you should understand, Gene, that I do not accept indiscriminant admiration from just anyone. Admiration means so much more when it has a price – when it’s a privilege that has to be earned — wouldn’t you agree?”
“Sure.” Each time she said any variation of the word ‘admire’ I thought of another specific way that it might be expressed – touching her stockings, kissing her feet, inhaling her scent . . .
She made a show of uncrossing and re-crossing her legs the other way around. The distinct sound of the nylon stockings rubbing against each other sent a jolt through me. She bounced her leg some more. “What do you think, Gene? Would you consider it a privilege — to admire me?”
“Oh, yes . . . no question . . . absolutely.” . . . rubbing my hands across the taught fabric covering her ass . . . going down on her . . .
“Do you think you’re ready to discuss what you’d be willing to do for that privilege, Gene?”
I nodded emphatically, “Oh, yes.”
“Good.” She stood up abruptly and said, “Stay put.” She walked over to the entry doors, threw the deadbolt, and switched off the front light. She returned and bluntly directed, “Follow me.”
She led me to an office in the back. It had a few desks against walls and 10′ square area rug in the middle. She found a hard back chair, set it on one side of the rug, and said, “Sit,” which I did.
She rolled an executive desk chair to the other side of the rug. She sat back comfortably in it, crossed her legs, and studied me. I was excited and nervous but I knew she had the lead and my place was to wait.
“Ok, Gene, let’s talk. Do you know who I am?”
“My name is Regina Wakefield. You can call me Regina, at least for now. I was the head of Library Sciences here up until about six years ago, when I went overseas to study Psychology. This room was my office when I ran this little library very early in my career. I’m back for a while filling in for an old friend as a favor. So, Gene, what are you studying?”
“Mmm. The study of tongues. That could prove useful. You’ll be a Senior next year?”
“Mmm hmh. I’ve seen you here at the library on several occasions. You study hard, don’t you Gene?” A slight smirk on her face made me realize she wasn’t just referring to my books and I blushed. “I think I already know your favorite subject.”
She was bobbing her leg, which made that swishing sound of nylon on nylon, and was playing with the hem of her pleated skirt again. She allowed the hem to ride up until the tops of her stockings were in full view. She occasionally reached down to smooth a stocking up her leg. “You like my stockings, don’t you Gene?”
“Tell me more. It’s OK, go ahead.”
“Wha . . . what?”
“Tell me what you like. I want to hear you say it.”
“Say what? What do you mean?”
“Oh, Gene. So much to learn. If you want to admire me, you’ve got to do what it takes to earn that privilege, remember? I’m a librarian, Gene. If you want to admire me, you’ll have to use complete sentences. I like to here it — all of it. Do you think you can do that?”
“Well . . .?”
“Oh! I like your stockings. You have beautiful legs!”
She shifted to a sing-song voice, “That wasn’t so hard, now, was it? And just like I told you to – so very obedient. I think you like to hear me tell you what to do, isn’t that right Gene? You like doing as you’re told!”
What could I say? It was true. “I . . . think so, yes. Oh! Um, yes, I do like you telling me what to do – it’s very exciting. I have this strange desire to please you.”
“Oh, it’s not strange at all, honey. It’s the most natural thing in the world, to want to please a lady. Do you know what would really please me right now?”
“What? Whatever it is, I’ll do it. Just tell me. I want to!”
“I like my admirers to be very obedient, and compliant with my wishes. I will grant you certain special privileges provided that all our interactions are on my terms. Do you understand?”
“OK . . . yes, I understand. All on your terms,” and when she raised an eyebrow, “All our interactions must be on your terms, and I have to do as you tell me.”
“That’s right! You’re getting it. And you should also know that I will have many demands. Do you think you could handle that?”
“I’ll try to. I mean, I want to. I think I’d like that.”
“There’s more. I expect you to be totally honest with me, especially with what you are feeling. Looking at me stirs up some strong feelings inside you, doesn’t it, Geney?”
“Yes, it’s a little overwhelming.”
“I can help you with that Gene. Help you understand and explore those feelings. Would you like that?”
“Very much. I’d like that very much.”
She stood up, stepped forward to me and held out her hand. As I took her hand she pulled me forward, but put her other hand on my shoulder and gently pushed me down as I slid off the chair onto my knees. She pushed me back to sit on my heels and said, “Stay right there.” She walked around me and moved my chair off to the side of the rug, then circled me completely until she stood right in front of me. Her belly was level with and a foot in front of my face. It surprised me how intensely exciting such a simple act could be. Thoughts of overt sexual acts flashed through my mind. I desperately wanted to be intimately sexual with her. She had slightly different plans.
She placed two fingers under my chin and tipped it up so that I was looking up at her towering over me. Seeing her looking down at me like that made me feel very meek, even though she was smiling at me.
“Look at me, Gene. I want to see the look on your face as we do this.”
I wasn’t sure what ‘this’ was, but I did want to please her so I kept eye contact, even though it felt so intimate, but in an uncomfortably intimidating way.
She pet my hair and brushed it away from my eyes, leaned down and softly said to me, “I want to hear you ask for the privilege of admiring me, and I want to hear sincere yearning in your voice. Can you do that for me, Gene?”
I whispered a barely audible, “Yes,” like it was confessing a dark secret that I was ashamed of.
“Then do it, Gene. Say it now. All of it. And mean it.”
“I . . . um . . . Ms. Regina, you are so beautiful, and, um, I can’t take my eyes off of you,” I started out a little shakily, “and I want so much to admire everything about you. I know it is a privilege, and ask that you please give me a chance to earn it.” I was starting to get some momentum. “Please allow me to admire you. God, I want so badly to kiss your legs!” I blurted out.
“That was pretty good, Gene. I bet it felt good to let that all out. But you must understand that whatever I decide to do with you will be entirely on my terms. Do you think you’d be able to accept that?”
“Um, I understand — all on your terms. Yes, I can accept that. It’s worth it – I mean, you are worth it.”
“Of course I am, dear boy. And if you’re a good boy, the rewards can be great. Lovely things come to obedient boys and girls. You promise to always comply with my wishes and obey my directions, hnnnh?”
“Yes . . . oh! I mean, yes, I promise to always do what you tell me to. I don’t know why, but I . . . I feel . . . like I really want to.”
She grasped my head and hugged my face snug to the soft swell of her belly, and said very softly “Do you trust me, Geney?”
I was feeling overwhelmed, surprised with the intensity of my emotions. It was all I could do to burble out, “Unh hunh, I want to.”
“That’s a good boy. You need to trust me, because I understand these feelings you are having. And I can help you realize them — beyond your wildest dreams.” She began to pet my hair and subtly rock back and forth, causing the cheek I had pressed to her belly to slide back and forth a bit. I could feel the slick slipping of nylon on nylon, and I guessed it was her slip sliding across the front of her panties.
“You like that, baby?” I was in a state of complete surrender, totally mushy. She was holding me tighter to her belly, “You want to be Regina’s special pupil? Hnnnh?” A subtle verbena perfume had enveloped me and intermingled with it I could smell the scent of her excitement. It made me hard as a rock.
“Glggglggggllrg” I couldn’t speak anymore.
And then, in a baby-talk voice, “Oh! It looks like Geney-weenie is all excited to be so close to Ms. Regina. It’s too bad our time together this evening is almost up. Geney-weenie’s going to have to go soon.”
“Hunh? was all I could muster.
“Would Geney-weenie like a memento to remember our special evening together? A reminder of your agreement to our special arrangement?” With that she reached up under her skirt, pulled her panties down, and tucked them in my pocket. “A little something for you to study at home. I expect you to become very familiar with them – and next time there just might be a test.”
I just stared dumbly at my pocket.
“That’s it for tonight — it’s time for you to go.” She abruptly pulled me to my feet, took me to gather my books, led me to the door, and saw me out with a “Until next time, good night, Gene.”
I stood on the entry porch in a daze. What just happened? It felt as if I’d just had a bizarre hallucination. As I walked to my apartment, the reality of the cool evening air made the memory seem like a dream. By the time I got home I had almost convinced myself that it couldn’t possibly have happened.
I shut my front door behind me, dumped my books and went straight for a shot of rye whiskey to calm my nerves. The burn ran down my throat, the warmth flushed my cheeks, and I noticed I was still wearing my coat. As I went to hang it in the hall closet I saw the white lace peeking from the pocket and it hit me – it was real, it had happened, and the physical proof was right before my eyes — the panties she had taken off and stuffed in my pocket.
I pulled them out and looked at them, stunned. My god, she had actually taken her panties off and given them to me.
Had she called me Geney-weenie? She had, and I hadn’t even cared. Her words came back to me: would I like “a memento to remember our special evening together?” Well, they certainly did that. And she had said “A reminder of your agreement to our special arrangement?” What had I agreed to? Her terms, everything on her terms – that was it. To do as she said, obey her directions. That didn’t seem so much. That was the price – to “admire” her. What admiring might entail made me lustfully crazy. That would be our “special arrangement” — do as she says, get to “admire” her.
My thoughts turned to admiring her – looking at her legs in those stockings, staring at her sumptuous ass, feeling with my cheek her slip sliding across her panties, smelling the mixed scents of her perfume and her feminine arousal . . . oh my god, I had her panties in my hand! The panties she had just been wearing! What had she said? “A little something for you to study at home.”
I had been lost in my thoughts and now looked at her panties closely for the first time. They were snowy white full-back panties with stretch lace in front and slippery microfiber satin in back. I alternately fingered the slick back and the stretchy lace and was overcome with unexpected emotions – gratitude that she had rewarded me with something so intimate, excitement that they had been in touch with her most private places and carried her very personal scent.
I remembered what else she had said: “I expect you to become very familiar with them – and next time there just might be a test.” She wanted me to smell them! She wanted me to know her special scent! I held her panties to my nose and inhaled. The citrusy smell of verbena was the first thing I noticed then it gave way to the subtle undertone of her feminine bouquet. It was utterly intoxicating and I wanted more. I pulled them from my nose and looked at them again. The cotton crotch was damp and on closer inspection I could see a thick white streak of her sweet cream. I knew that that’s where her scent would be strongest. I wanted to smell the soiled crotch but didn’t want to put my nose in the goo, so I turned the panties inside out and held the satin side of the crotch to my nose. I liked the slick feel of the nylon against my nose. The odor of verbena was much fainter here, but her scent was strong.
I was so aroused I had to jerk off, immediately. I dropped my pants and underwear and knelt right there in my entryway. I pulled the inside-out panties over my head and positioned the fragrant crotch over my nose. My cock was so hard it almost hurt. I frantically jerked my cock with one hand while holding the panty crotch tight to my nostrils so that the air I breathed in was sucked through the dampened panty crotch. The smell was intense. All I could think of was “cunty.” I desperately inhaled the pungently cunty air through the satiny panty crotch which was thickly smeared with Regina’s pussy cream until I ejaculated. I came hard, spurt after spurt on the floor, for half a minute.
That weekend, I did study hard as instructed. Two or three times a day I jerked off while smelling her panties. By the second day I had to moisten the crusting smear with my breath to get its full pungency.
On Monday night I anxiously looked for her at the library and was disappointed that she wasn’t there. I really wanted to see her again. That night I let go of an inhibition and licked her gooey pussy cream on the cotton gusset. A desperate need to see her was building up in me. When she didn’t show again on Wednesday I lost all inhibition that night and desperately began sucking every vestige of her essence from the soiled crotch of her panties. I felt like I knew her intimately.
Friday evening came and I was desperate to see her. As I entered the library I spotted her talking with Becky, who was one of the grad students that normally covered the front desk. She briefly looked over and saw me but continued talking. I sat in my regular spot and got set up to study but all my thoughts were on her. A half hour passed and I was surprised and disappointed that she hadn’t dropped by to see me.
I finally got the gumption to wander up to the front desk. She was standing there flipping through the log. She was wearing an accordion-pleated skirt again, this time longer and in red, with a white satin blouse and a wide black belt. Black hose and heels finished off the outfit.
She noticed my approach and turned to face me with her fists on her hips, “Yes, what is it,” she said abruptly, seeming impatient and irritated.
I was taken aback a bit, “Oh, I just wanted to say hello. I thought you might want to talk.”
“I’m afraid I’m a little busy right now. When it’s time, I’ll let you know. Terms, sweetie, remember whose terms.”
Unexpectedly chagrined, I slunk back to my alcove. I wanted to hate how she’d treated me, but I had agreed to those conditions – everything entirely her terms. She had clearly put me in my place, a place that I had already freely accepted. I hated being treated that way but there was no question in my mind that it was worth it to be close to her. I had been desperate to see her in person again and her rebuff just made it worse.
I tried to study but was in too much turmoil to get much done. I kept dwelling on thoughts that she had just been screwing with my head as a way to get back at me for ogling and actually had no other intent. I kept thinking that I had no reason to believe otherwise, but hoped that wasn’t the case. I’d gladly take the grief for a genuine connection with her. I consoled myself that she had really seemed to enjoy the interaction, way beyond a simple satisfaction from revenge. She’d had a gleam in her eye that told me she enjoyed tormenting me for its own sake. I was surprised to realize that on some level I had enjoyed it too, and I definitely knew I wanted more.
All these musings kept my mind occupied for the evening as I accomplished very little studying. Finally, close to closing time, she came by. Almost reflexively I went into a more submissive mode.
She placed her hands on the desk and leaned down to me. “So you’re still here.”
I glanced briefly at her pendulous, satin-covered bust, quickly turned my eyes down, and meekly answered, “Yes.”
“You’ve been at it all evening. Do you study this hard at home?” Her expression was as neutral as the words seemed innocent. The double entendre made my mouth go dry, as I knew exactly to which study she was referring.
“Yes. I’ve been studying very hard at home in the last week.” I wanted her to know that I had diligently done my homework.
“Mmmm, that’s good. Perhaps you’d like to tell me all about that — after I close the library, of course?”
I was elated, “Yes, I’d like that very much.”
“Good! Go ahead and gather up your things and wait for me in the office.” and she turned and walked back towards the front desk.
I dumbly watched her swaying hips recede from view, then scrambled to pack my books and hightail it back to the office. When I got there it seemed natural to place the chairs in the position they had been in at our first encounter and sit in the hardback chair to wait. I had about five minutes to reflect on what I was doing. My mind raised objection after objection, but my passion overruled them all.
She whisked in the door and quietly closed it behind her. She turned and looking intently at me made a point of throwing the deadbolt. I felt a chill run down my spine. She walked around in front of me and stood about six feet away.
“It was thoughtful of you to try to set the room up, Geney. I like that. It shows you can anticipate what may be required of you. That’s a quality I value.”
“Un hunh. Oh, say, how do you like my outfit?” She held the sides of her red taffeta, accordion-pleated skirt, fanning it widely to the sides.
I thought I could barely see the outline of her body through the delicate material, “It’s lovely.”
“More. . .”
“Oh, right! I love your skirt. It’s the same style as the one you wore last week, but longer of course and red and . . .”
“Did that bring back good memories for you, honey?” she said, smiling.
“Oh, yes, very much so. I like the color, it’s very . . . assertive.”
“Interesting word choice, Gene. Red does make me feel more confident, as I’m sure you’ll find out. Do you like my blouse?”
“Yes, it’s very pretty. I love that it’s so shiny.”
“Mmmm, satin is lovely, isn’t it? It feels so sensual against the skin, and it’s so nice to touch. Very soft and smooth –wonderfully feminine. But the tailoring is quite professional, don’t you think? It makes for an interesting contrast. Do you see that, Gene? Can you tell me what that contrast might be?”
“Um, like between pretty and businesslike?”
“Very good! But I prefer different terms – feminine and authoritative. To the uninformed that may seem paradoxical, but I assure you it is not. She pondered silently for a while and then said, “You’re attracted to me, aren’t you Gene?
“Yes,” I squeaked out, “very much.”
“And you like how I dress – in very feminine, sensual textures — isn’t that true?”
“Oh yes, absolutely!”
It’s perfectly natural for you to be attracted to the feminine, sweetie. I can tell how much you desire to be near it. So much so that, for the opportunity, you are willing to do my bidding. You are willing to submit to my feminine authority, isn’t that right Gene?”
I choked out an embarrassed, “Yes.”
“I love dressing as I do, partly because it enables me to control men — which I thoroughly enjoy. Would you say I already have some control over you, Geney-weenie?
I winced at the name, then thought about all that I had said and agreed to, and what I’d done with her panties all week, and confessed “Yes, more than I could have imagined.”
“And I bet you enjoyed that, am I right?”
“Yes . . . yes, I enjoyed it . . . quite a lot.”
She pulled my hand and pushed down on my shoulder like the last time, saying “Get on your knees, Geney, where you belong” and I slid into the same position I had taken the week before.
She leaned her bottom against the edge of the desk, placed her palms behind her on the desktop, and casually crossed her extended legs. The contrast of our positions was not lost on me; she was relaxed in a casual position above me while I knelt uncomfortably in a subservient position below her. What particularly struck me was how comfortably at home she seemed with the situation, like it was the most natural thing in the world and totally expected. That in turn made it easier for me to accept.
“Now, Geney, it’s time to talk about your studies at home. Tell me everything — and I expect you to be honest and frank.”
“OK . . .” The magnitude of telling her what I had done with her panties suddenly hit me. What if it wasn’t what she wanted? What if it grossed her out? I hadn’t even considered that. I struggled with that thought in silence.
“Awww, what’s the matter, honey, cat got your tongue?” she taunted.
I just couldn’t bring myself to talk about it. I was facing telling this seemingly proper, middle-aged woman of the pathetically perverse acts I had performed with her panties, and the embarrassment was suddenly overwhelming.
She stood up and stepped forward to stand right in front of me. The rustle of her taffeta skirt and swishing of her stockings were intimately close. She looked down at me and bemused, “Oh sweetie, you look terrified! Ha, ha! Poor baby. Let me help you out.” She tipped my head up to look at her face and softly intoned, “Just pretend that I’m your favorite aunt, the one you’ve always been able to confide in. You need to tell your Aunty Regina what you’ve gotten into, poor boy. Get it off your chest to Aunty Regina and it will help you feel better, hmmmmh?”
“OK,” I was melting inside.
“OK, who? Who am I now?”
“OK, Aunty Regina.” It was humiliating, but it did make it easier to talk.
“Now, Geney, to make this easier for you, Aunty Regina is going to ask you some questions. And Geney needs to be a good boy and tell his Aunty all about the things he’s done, understand?”
She stepped back and scooted up to sit fully on the desk. Her legs were splayed open, revealing a peek at the red panties she wore. She knew exactly what she was doing. My eyes were fixated on her red panties. Her knees opened and closed rhythmically.
“Good. Aunty Regina gave Geney something special last time. Tell me what that was.”
“Um, her panties. The panties she had been wearing.”
“Yes! What a special present for Geney! Did Geney-weenie like them, hmmmh?”
“Yes,” my voice was cracking.
“And did Geney-weenie study Aunty’s panties like he was told? “
“Yes, very thoroughly.”
“Did you smell them?”
“Yes, I smelled them.”
“My goodness, what a naughty thing to do! And after I’d worn them all day! Did you like how they smelled? “
“You liked sniffing my panties – my fragrant soiled panties?”
“Say it. I want to hear you say it,”
“I . . . I liked sniffing your fragrant soiled panties.” Saying it brought surprising relief.
“There, that wasn’t so hard, now was it?”
Now tell me everything. Everything you did and everything you felt. Regina wants to hear you tell all.”
Once the initial taboo was aired, it all started to come out, like a siphon had been started. The more I said the more embarrassed I felt but also the more relieved to let it out. It gained its own momentum to where I couldn’t stop and didn’t want to.
“Yes, I liked sniffing your panties, especially the soiled crotch. I love how they smelled. I put them over my head and jerked off while smelling them. I’ve done that at least twice a day all week since you gave them to me. I didn’t want to at first but after a few days I . . . I . . . started licking them.”
“Oh my! My panties compelled you to do that? Ha, ha! Oh, sweetie, were my panties controlling your behavior? I knew you would be easy to panty-whip but I didn’t expect you to surrender so easily to them on your own without any encouragement! What a natural panty boy you are! Now tell me where. Where exactly did you lick, babydoll?”
“Um, . . . I licked the inside of the gusset. I lapped it up, all your sticky pussy cream. And later I sucked them clean.”
“Naughty, boy! How’d it make you feel? Did Geney-weenie like sniffing and licking Aunty Regina’s dirty stinky panties?”
“I loved it! It felt so good, like I was safe at home. I’ve never been that excited before! I couldn’t control myself and didn’t want to. I just had to jerk off. “
By this time I was drunk with lust. She was blatantly exposing her red panties to me and I wanted so badly to lick them while she wore them. She seemed to know this already. Her eyes glowed like coals. She spread her legs a little wider.
“That’s very good, Geney, very good! I really like hearing you tell me how my panties affected you; how you lost control to them. You’re looking at my panties right now, aren’t you Geney?
“Unh hunh”, I had fallen into a trance looking at her red panties through her slowly oscillating legs.
“Crawl over to me, Geney, so you can get a better look.”
My dick was so hard it was awkward to crawl, but I did so until I was a foot away from her pantied mound. I could see the outline of her labia through the thin material and the aroma of her arousal was making my head spin.
“Look, Geney, look at my panties. They control you, don’t they? You’d do anything to worship them, wouldn’t you?”
“Unh hunh.” was all I could muster.
“Would you like to be Regina’s panty boy? You wanna to be my widdle panty-sniffing, crotch-licking, jerk-off?”
Her words got to me. “Ohhhhh, unh hunh, please, may I?”
“Mmmmm, very well. Today’s your lucky day” as she slid off the desk.
She deftly unbuckled her belt, unzipped her skirt, and stepped out of it. She then pulled her red panties half way down, so they were taught between her mid-thighs. Her swollen labia protruded from just beneath her black garter belt.
“Come and get it, panty boy. Come smell Regina’s panties. Only sniff.”
I put my face right down close to the panty crotch. I could feel her labia brushing the hair on the top of my head. I deeply inhaled of her scent. Laced through her thick womanly bouquet were very faint overtones of urine and ass musk. The lushness of her scents with their accompanying pheromones hit me like a jolt of narcotics and my balls immediately tightened, “Oh, God! Ohhhhhhhhhhh.” was all I could say. I was completely intoxicated.
“Uh, uh, that’s enough for now!” she said as she pushed me away. She pulled her panties back up and proceeded to remove her shoes and unclip and remove her stockings. She pulled the desk chair over, pulled her panties half way down and sat in the chair.
She grasped the panty crotch with her fingers and turned it inside out.
“Come closer, Geney. Do you see those slimy white streaks on my dirty panties? That’s Regina’s pussy cream. Is that what you like to lick up?”
“Oh, God … oh, God . . . yes! Yes! Ohhhhhh!”
“Show me how you like to lick Regina’s dirty panties. I want to see you lick up my creamy pussy juices. Do it!”
The humiliation I felt when telling her that I’d licked her panties had been tempered with the relief of confession. Being told to lick her vaginal secretions off of the crotch of her panties while she watched was more intensely humiliating than I ever would have imagined. And yet I strongly felt compelled to do it. I had agreed to do as she told me – to obey her. And regardless of that I desperately wanted to. I started to lick the pungent salty goo off the cotton gusset while she held them out for me. As I licked I could feel her fingers on the other side of the crotch, pushing them against my tongue.
After a little while she said, “Wait” and stopped to slide them off her legs. She made me stick out my tongue as far as I could and hold it out and she used her fingers to vigorously rub and wipe the slimy inside of the crotch on my tongue, “That’s it, lick it all up, panty boy. Every little bit! Mmmm, yummy!” I almost gagged but my dick was the hardest it had ever been and I didn’t want her to stop.
“Okay, Geney, that’s enough. You clearly like that, even though it’s second hand. I think it’s time for you to get some of that yumminess fresh, right from the source. Would Geney like that, hnnnh?”
“Ohhhhhhhhhhhhh,” All I could do was let out a low moan of assent.
She scooted forward on the chair and firmly pulled my face to her crotch. “Lick my pussy. Get your tongue in there really deep, as far as you can. Ahhhhhhhh, that’s it. That’s what you’ve been wanting all along isn’t it? Suck up all my juices. Show me what a good cunt lapper you’re going to be for Aunty Regina!”
She had me eat her out for a long time. She kept a tight hold of my head, pushing it around and directing me how she wanted to be licked, tongued and sucked. She told me over and over that I was her cunt lapper now, how she was going to have to train me to do it just the way she liked, and that many hours of practice would be required. I was in heaven and lost all track of time.
The first time she came, a little fluid squirted out and coated my face. She just kept going, using it as lubricant for humping my face. As her second orgasm approached she warned me and said “I’m going to come again, Geney. I’m going to squirt my cum in your mouth. Catch all of it this time, don’t miss a drop! Here it comes! Ohhhhhh! Ohhhhhh! Ohhhhhhh!” and she let loose with a series of short squirts. I caught it all and swallowed it.
After she had come down a bit from her orgasms, she produced a towel from somewhere and wiped my face off in an almost methodically maternal way. “That was good, Geney, very good. Did you enjoy that too?”
I was on another planet. Her toying with me, dominating me, and using me for her sexual satisfaction was the most exciting, gratifying experience that I had ever had. I felt like I could and would do anything for this woman.
My dick was so hard that it hurt. I was whimpering a little whenever I changed position.
She saw my suffering and reached out and grabbed my dick through my pants. I almost went through the roof. “Oh, it looks like someone here did enjoy that. Good lord, it’s hard! Let’s take a look at your little weenie. Stand up and take your pants off, Geney.”
I stood up in a daze and she started unbuckling my belt for me. As she began to pull my trousers down I came to my senses, realized what was happening and, in a panic, held onto my pants to keep them up.
“What are you doing, Geney? Let go, I want to see your little dickie,” and she yanked the pants out of my hand and down to the floor. “What’s this then? Oh my God! Those are my panties! Ha, ha, ha, ha, ha! You’re wearing the panties I gave you last week! No wonder you didn’t want your pants down.”
With my pants around my ankles I stood before her utterly mortified. I had washed and dried her panties intending to return them to her. I had forgotten that I had impulsively put them on that morning in a desperate attempt to feel closer to her. At the time it had seemed reasonable but now it just seemed pathetic.
“Oh, Geney! you are a panty boy, aren’t you? Ha, ha! You know, I’ve been calling you Geney as in G-E-N-E-Y, but now I think Jeanie as in J-E-A-N-I-E might suit you better. Yes, I think from now on when you hear me say “Jeanie” you should know that I mean J-E-A-N-I-E. Others might not notice the difference but you will know. Oh, we are going to have so much fun with this, Jeanie with a J.”
I was dying of humiliation. What had I been thinking? I noticed that my dick had noticeably softened.
“So, Jeanie-jay, I knew you liked me wearing very feminine clothing but now I see you like wearing pretty things too. Apparently, you like wearing my pretty panties, hnnnh? Do they make you feel special? Like a pretty girl?”
She had pulled the front band of the panties out so that she could inspect my dick.
“Oooh, what happened to Jeanie-jay’s little dickie-poo? It was so hard before.” With that she began aggressively kneading my penis. “I want to see Jeanie-jay getting really hard in her pretty panties!”
I was moaning and whimpering. I hated the direction this was leading but the combination of the physical stimulation and the humiliation was getting me really hard again.
“Does Jeanie-jay like dressing up in girly things? Hnnnh? Maybe Jeanie-jay is curious to see what it would be like to be a girl, hnnnh?” She was grasping my dick through the panties and jacking me off. I wasn’t going to last very long.
“Would Jeanie-jay like to be Auntie Regina’s niece and dress up in pretty panties and party dresses?” With that last remark I shot my load, hard. “Oh, my! I think we just learned that Jeanie-jay gets excited thinking about being girly! Ha, ha!”
I was mortified – that I had come when she said such things and that she was pointing that out. I just wanted to hide. Thankfully she seemed to let it go by. She patted my waning erection and said, “I think that’s enough for tonight, Jeanie. Pull up your pants.” She had me gather my things and within two minutes I was once more out on the doorstep.
I didn’t see her again for over two weeks.
She had really gotten in my head. After that last encounter I couldn’t go ten minutes without thinking about her. I ached to submit to her feminine authority. I wanted to be kneeling in front of her, smelling her scent, tonguing her deeply, and drinking her squirts of cum.
First thing in the morning when I woke up, I jacked off thinking about her; last thing at night before going asleep, I jacked off thinking about her; sometimes even during the day I would start thinking about her and have to find a lockable unisex restroom to jack off in.
I didn’t have a pair of her worn panties anymore, just the ones I had come in and washed a second time. So as masturbated I would replay in my mind the things she had done and said. Eventually, I would come to the part where she said, “Does Jeanie-jay like dressing up in girly things? Hnnnh? Maybe Jeanie-jay is curious to see what it would be like to be a girl, hnnnh? Would Jeanie-jay like to be Auntie Regina’s niece and dress up in pretty panties and party dresses?” and that’s when I’d come.
I started to obsess on those remarks. Damn it, why had I put on her panties? What did that mean? And why had her remarks about me wanting to be girly and wear panties and dresses made me come? The more I thought about it (and came to that thought) the less I was repelled by it. But still, it was simultaneously compelling and frightening.
Three times a day over two and a half weeks is just over 50 ejaculations, each time hearing her words ring in my head. The longer I went without seeing her, the more desperate I felt. I was gradually convincing myself that seeing her again might be conditional on my acceptance of the truth of her remarks. After all, seeing her was completely on her terms, which meant submitting to her feminine authority. And submitting wasn’t exactly masculine. And it did excite me terribly to be dominated by her and to serve her sexually, satisfying her orally. And I was inordinately drawn to the soft satiny textures she wore. And I had put her panties on, for Christ’s sake. The more I thought like this, the more the prospect was turning me on. If I even thought about wearing panties or a dress I’d get a hard on.
I came to realize that she was dominating me and transforming me without even being present or involved. She’d had me doing her bidding, and now I was acting for her to mind-fuck myself all the way to Pansy City. All she’d had to do was lay the groundwork and I’d taken it from there. The first time by giving me her soiled panties and the second time by making me come in my panties while taunting me about wanting to be girly. That too was part of the submission. And yet the deeper I got the more I wanted it that way.
The next time I contacted Regina was on a Wednesday night at the library. I hadn’t seen her for two and a half weeks and was quite desperate. I didn’t actually see her. Midway through studying I’d gone to the bathroom and when I returned I found a note propped up against my books. It was an envelope, the fancy kind they use for special occasions. On the front in lavish floral script “Jeanie” was written. I looked around and didn’t see her anywhere.
I opened the envelope and pulled out a very formal looking invitation, printed in lavender colored ink. It read:
Ms. Regina Wakefield requests your presence on this Friday evening at seven P.M. sharp at 110 Coventry Lane for an evening of service and transformative transcendence. Dress appropriately for the occasion. R.S.V.P unnecessary as attendance is expected.
I felt like I’d just received a special honor, like an invitation to the white house. My god, was that where she lived? Had I actually been invited to her home? I struggled to keep my imagination in check.
The next day, Thursday, my mind churned obsessively about what might transpire. On my way to work the next day, I walked by the street – not by the address, which was midblock – just to the corner of the nearest cross-street. I peeked down the block and guessed it was the classy building that looked like it had a courtyard. I don’t know why, but I felt terribly guilty that I had gone by like that.
I also kept returning to the language in the invitation. It was addressed to Jeanie, not Gene or even Geney. It promised “an evening of service and transformative transcendence.” Service was obvious enough; but it sounded like her expectations might go much farther than I dared imagine. From her choice of words, all I could surmise was that, in some big way, change was in the cards. Then there was “Dress appropriately for the occasion” but what occasion might that be? Was it going to be a party or formal dinner? I doubted that. No, I thought I knew where all the signs were pointing. Damn it if my cock didn’t get hard again at the thought.
I guess I knew what she expected me to do. I was terrified but I felt I had to do it. So, during my lunch hour I took a trip to the local mall and made my way to one of the higher end department stores. I found the women’s lingerie department and loitered outside for about ten minutes trying to work up the courage to go inside. I waited until there seemed to be a lull in the number of women browsers and then headed for the area that looked like it carried panties.
The variety on display was overwhelming. I tried to narrow down the choices quickly so I could minimize my exposure time amongst the frillies. I was strongly drawn to those that had a satiny feel, and found myself fondling pair after pair to gauge the tactile sensation. I knew that I wanted that satiny feel. The style had to be the full-backs — more room for my stuff and more fabric to feel. The color was harder. I just couldn’t do pink, but really liked a lavender colored pair. Then I got to size and looked for the dimensions of the waist in inches. What the hell size is a 6 or 10 or 14? I was stymied.
“Can I help you?” She was young, maybe 18 at most. A little on the short side, but pleasantly proportioned. Dark hair pulled back into a ponytail, and dark framed glasses. An utterly charming crooked smile, and air about her that was a combination of sincerely earnest professional and intellectually irreverent goofball. I just blinked at her dumbly, not knowing what to say.
“Hello? Mars to Mr. Customer – do you read me?”
“Oh, sorry, uh no, I was just looking and . . . “
“You need help with the sizes, right?”
“Well, yes, as a matter of fact, I do.”
“Do you know her size, or her waist or hip measurements?”
“Uh, no, not exactly. That’s the problem.”
“Has she ever worn your pants?”
“Wha . . . what?” This was getting really weird.
“You know, so you would have a comparison.”
“Oh! Yes, well, then I suppose so. I guess she’s pretty close to my waist size.”
“Ok, in that case, I’d say she’s probably close to a size 8. If they are way off, she could return them anyway.”
“Oh, good. Thank you. That was very helpful.”
“No problem. Nice choice by the way. Any girl would love to wear those. Very pretty color.”
I could feel a blush welling up, “Thank you.”
“Don’t mention it. You know, we sell a matching bra, as well. Would you be interested in that?”
My ears started to burn with embarrassment and my mouth went dry. “But I wouldn’t know the size.”
She stepped back and looked me up and down and smilingly said, “I’d say a 38A might work.”
Now I was deeply embarrassed. There wasn’t any doubt in my mind that she had eyeballed the size by looking at me.
Still, I said, “Uh, I’ll take it.”
“Very good sir. Will that be all for you today?” Everything she said now seemed like a double entendre.
“Yes, that’s it.”
She wrapped it all nicely in tissue paper and I paid her.
As I was about to leave she whispered to me “Do you want to know how I knew?”
I wanted to play stupid but was genuinely curious so I said, “OK, how?
“All boys sooner or later cross paths with one of their girlfriend’s bras. They are always compelled to check out the size, and they tend not to forget it, either.”
“Mmm, good point. And thanks so much for your help.”
“Anytime. My name is Ginny.”
“Thanks, again Ginny.” I didn’t offer my name and was so relieved to be out of there.
When I returned to work I took great pains to keep my new purchase safely hidden from view. Still, until I could take it home, I was very nervous. I could hardly wait until I could look at the lingerie in privacy of my own home.
That evening after dinner I set my new treasure on the bed and reverently unwrapped the tissue paper. I picked up the lavender-colored panties with shaking hands and eagerly fondled the satiny texture. My heart was beating fast and I could feel my pulse in my fingertips. I stared at them and thought about the significance of the line I was about to cross.
When I had donned Regina’s panties a few weeks before, I had convinced myself that it was a misguided effort to feel close to her. This was clearly something else. These panties weren’t hers at all — I had purchased them myself, of my own accord, in my size, with intention of wearing them. I had repeatedly masturbated and come so many times over the last few weeks while thinking about wearing pretty panties. The budding desire to feel girly was intensely erotic — maybe because it was so forbidden – and I felt myself drawn towards it. That Regina seemed to encourage me in that direction and then belittle me for it made it irresistible. I didn’t just want to wear panties. I wanted to do it in front of her and have her tease me mercilessly for it. I intensely desired her to humiliate me and then selfishly use me for her own sexual satisfaction.