It all started when I accidentally came across a site called “Literotica.” I am not sure what I was looking for but was interested in sex and passion, since my wife decided over twelve years ago that she did not like sex or at least with me. So, seven months ago, I turned to Literotica online to discover what pornographic stories were like. After many hours of reading about lesbian sex, frigid wives made to have horny sex, forced lesbian, forced wife into slut sex, I was curious about how or why straight guys turned into cock-sucking, sperm loving, anal pussy poked sluts.
Now you got to know that I have always liked girls and women. I like their bodies, their hair, their hips, their lips, their eyes, their thighs, their neck, their breasts, their tummy, their pussy, their legs. I love their softness, tenderness, their attention, touch and passion.
I don’t think I ever consciously thought that I wanted to be a woman.
However, in the back of my mind, I wondered what it would feel like to wear their panties and slips, to be desired and touched.
I always liked seeing women naked. I am small boned, thin (most of my life), been told I have a nice ass, and I have very little body hair and never could grow a mustache that looked like a mustache. My older brothers use to tell me I should have been a girl. As I passed fifty and gained a little weight, my chest formed small breasts. I have always needed to be hugged, held, caressed and kissed. I craved intimacy. I need the attention of touch.
I never thought a naked man was attractive, in fact, I thought that their genitals and bodies were ugly. But after reading in Literotica about straight guys who were forced or blackmailed into giving blowjobs for the first time, or taking a cock in the rear for the first time then learned to like it, or forced to swallow loads of cum and become addicted to it or reading about the enjoyment received from being another man’s bottom and cock-sucking whore, I began to fancy being a bottom to a big guy’s top.
Having read those forced gay stories about how a turned straight wanted to please a man, feel a touch, passion, physical intimacy or wearing ladies things, after several months of reading, I would drift through the ladies shops in the department and discount stores. After some weeks, I started just looking at lingerie and then I progressed to touching and thinking about buying ladies undies.
Many weeks into my reading and self brainwashing, I worked up the courage to ask a sales clerk how to determine what sizes women wore for articles of lingerie such as slips, thigh high stockings, panties, baby doll pajamas, chemises, bras, etc. The silky, satin feeling of these female garments was fantastic and I wonder again what it might feel like to have them and wear them.
One afternoon, I was running a pair of white silky panties between my thumb and fingers, enjoying the touch, and fantasizing, when behind me a deep voice said, “I’ll buy those for you if you will let me see you in them.”
Embarrassed, I turned to see a very tall man in his forties, weighing perhaps 60-70 pounds more than me, standing about four feet directly behind me. He was dressed in business casual and appeared to be a professional businessman. This stranger with dark hair, brown eyes and a square jaw line on a nice but masculine face was looking at me. I am six feet tall and I had to raise my head to look at his face.
No one knew of my interest in ladies under garments or my self-induced fantasy. I just stood silently staring up at him for a few heart beats. Then I said, “Oh, no, I was just looking for a gift for my wife.”
“My offer still stands,” he said in his radio deep voice. “Are you sure they are for your wife or yourself?”
This was crazy; I was caught, fortunately by a stranger. I was embarrassed but part of me that had been practically brainwashed by all the stories of straight guys loving being a bottom, the taste of male love juice and the organism that comes from being repeatedly anally penetrated by a man was saying, “Do it. Do it!”
In a low voice I said, “If I agree, you mustn’t
tell anyone, I would be so ashamed.”
“I was looking at you from behind as you were trying to be so sneaky about touching those panties, I thought you would look good in them.” the tall stranger said. “Now that I see your face and front, why don’t I buy you a slip to go with the panties? What size should I buy for you?”
“Some weeks ago, a sales lady said that someone with my waist, hips and chest measurements would be a size 2x or 3x. I have never bought ladies lingerie before, so I’m not sure how they might fit. ” I quietly replied.
“Let’s get the 2x size, I would rather they fit you tight than loose, he said.” “You pick the panties and slip from the racks, hand them to me and follow me to the checkout stand. OK?”
“Yes,” I almost whispered as I quickly looked around to see if someone I knew was watching, pulling the white panties and slip from the rack. He took the slip and panties from me. We headed to checkout.
“Oh, wait a minute, he declared, “You will need a woman’s razor specially designed for shaving legs, under arms and other private areas. You will want some make up, like mascara, lipstick, perfume and an enema kit that you can reuse as needed.”
“What, are you crazy, I did not agree to anything but to let you see me in the panties and slip? I can’t pretend to be a woman.”
He just held up the panties and slip and said, “You know you want this, now is you opportunity. I find you attractive and if you pick up those items and use them, you will look sensational in the lingerie. “Meet me at checkout,” he said in a commanding tone, as he handed me back the slip and panties.
I went to the cosmetics aisle and selected a red shade of lipstick, some dark mascara, skin lotion and perfume. In the drug department, I found the razor and shaving cream for women, but I had to ask a clerk, where the enema bags and items were. I thought she looked at me a little strange, so I mumbled, “This stuff is for my wife, and she couldn’t shop today.”
I walked toward the checkout counters and saw him towering above everyone else. He saw me coming, smiled and motioned for me to get in line next to him. He held a bag of something that he had just purchased.
As we stood in line to checkout, I was nearly red faced with embarrassment holding the white slip, panties, make-up, lotion and the enema supplies. This was wrong and crazy.
Why was I feeling excited?
He paid and as we walked toward the door he asked if I knew where the Willow Valley Apartments were and I replied that I did. He said that when we got there, I had to follow him close through the entrance so the security gate would stay open as we went through together bumper to bumper.
As I followed him, I realized I did not even know his name or if he was insane, or a stalker, killer of older married men who touched women’s panties? I thought about what if someone finds out that I dressed in a slip and panties for another man and told my wife or my friends?
I kept following and driving.
As I approached the apartment entrance and pulled close to his back bumper, he was punching in a security code to open the gate. We drove through. I followed him to one of the many complexes and his apartment was near one of the complex pools. He parked, took all the bags we had purchased from his car and waited for me to come to him.
As I climbed from my car, he said, “Take your packages and follow me to the elevator.”
I did as I was told and as we waited for the apartment elevator, he dropped the bag that he had purchased before I met him at the checkout stand. The contents came out and I saw two cucumbers about the same length 7 or 8 inches, but one was at least an 2 inches in diameter and the other was maybe an inch and a half wide. He politely asked, me to pick them up and put them back in the sack and carry them in with my two bags. I could only imagine how those vegetables might be used.
The elevator arrived. We entered and as it ascended to the sixth level, the tall man said, “When we enter the apartment, you will take off all your clothes, place them neatly on a chair in the living room and stand in front of the couch. Don’t say anything and don’t move unless I tell you, got it?”
By this time the doors of the elevator opened, he put his arm around my shoulders and walked me to his front door about four units from the elevator. He unlocked the door, opened it and placing his arm around me again, escorted me through the front door. He switched on the lights.
He took the sacks from me, placed them on a coffee table and pointed to an arm chair next to a large stuffed couch. He crossed his arms and looked at me and gave me a silent command as he pointed and wave his arm to tell me to proceed.
I have never underdressed in front of a man who was not either a doctor, or in a gym class at school. I was nervous, self-conscious and little excited, too.
I did not make a show, I sat in the chair untied my shoes, took off my socks, stood up, took off my Izod knit shirt, my blue jeans and folded them up and put on the arm chair. I was standing in my boxers, in a strange apartment of a stranger, who offered to buy me panties if he could see me in them.
I placed my thumbs and fingers in the waistband of my shorts and pulled them down to my ankles, having already bent over; I lifted one foot and then the other. It occurred to me that from his vantage point I was displaying my back and my naked ass, as I bent over to pick up my boxers.
I placed my underwear on the pile of clothes in the arm chair in his apartment.
Buck naked, nervous, embarrassed and becoming horny, I walked about eight feet toward the expensive stuffed couch and stood four feet from the couch.
From behind me he said, “You can call me John that is not my real name, but you will call me either John or Sir. Do you understand?” As he said this, he walked by me slowing, running his hands across my exposed hips and softly squeezing my right ass cheek, patted my butt and sat down on the coach.
“Yes, John, I understand.”
“When you are with me, you will respond to the name “Sweetie” because you have a sweet sexy ass and small girly breast. What is your name?”
“Sweetie, my name is Sweetie, John.”
“Walk over here and stand directly in front of me, Sweetie.”
I took one and a half steps toward the sofa. John’s eyes, nose, mouth and face were slightly higher and nearly aligned with my genitals. I was slightly aroused, but my nervousness and fear kept me from being hard.
As he reached out and began squeezing my breast and pinching my nipples, something no one had ever done, he leaned in and kissed then sucked both my breasts. It felt strange, erotic and good all at the same time. When he bit on my nipples I felt a tingle of pain and pleasure I had never had.
He proceeded to run his hands down my stomach and over my thighs, as he worked on my small breasts. I was hard. He stopped pleasing my breasts and said, “Sweetie, when I take my hands away from your dick and your balls, I want you to go into the third door on your left with your bags.
I was excited by his sucking and kissing my breast, by his slowly masturbating me. Someone was touching me and wanted me for their pleasure. I needed attention and to be touched all my life. I wanted more. He was gentle rubbing and massaging my balls and penis as he was speaking to me.
“I want you to take a quick shower and shave all hair from your neck down to your toes. From what I see, you won’t have much to shave anywhere. Sweetie, have you recently shaved your legs and crouch?”
It was obvious that I had, so I said, “Yes, sir, I did about two weeks ago, while having a fantasy about this very moment.’
Continuing to slowing play with my now enlarge dick of 5.5 inches and balls, he ran his hands around my thighs to my lower hips and began squeezing and rubbing them. He rubbed my dick with one hand and with the other John began to run his index finger into my butt crack.
He then moved his hand from my hips and crack moving his fingers to my anus. He pushed against my anus with his index finger, never penetrating just teasing. He teased my ass with his probing for several moments, and then John moved that finger to my lips and told me to lick it and suck it.
As he massaged my engorged dick, I licked and sucked his index finger. I kissed it up and down, licking nail to hand, sucking in all into my wet mouth. I thought I heard myself moan a little.
He told me that he was going to push that finger into my ass and I had better get it good and wet. John said that I should suck his finger the way that I was going to suck his dick, after I showered, shaved, used the enema bag, put on the make-up, perfume and modeled the slip and panties.
After a few minutes of sucking his finger, while he played with my dick and balls, he pulled his index finger from my mouth and pushed it slowly into my ass. It did not hurt. He pushed in up to where his finger met his hand.
He had big hands and larger than normal fingers. His index finger was more than four inches long and slightly more than an inch wide. John pushed his finger in and out of my rectum slowly. In and out, in and out, in and out, slow then fast, fast then slow, in and out.
It felt invasive but it felt good. It did not hurt. I could feel my cock reacting. I had not had physical sex for over a decade. No one had touched me in an intimate way for years. I loved the attention, the feeling, the stroking. I was so close to Cumming.
Then unexpectedly, as I was beginning to hump his finger, he pulled his finger out and stopped touching me.
“Sweetie, he said softly, go get your shower, do your maintenance and come back dressed in your lingerie and make-up. Come back in here. I will be waiting. Make sure you shave all your hair especially around your dick, balls and ass. Look sexy for me, Sweetie, now go.”
I did as he instructed. Since I had shaved myself before, it did not take me long. As I soaped myself in the shower, I almost paid too much attention to my erection. I have had only hands on sex for too long and wanted another person to assist me to share my passion’s product with me.
Enemas were an experience I had as a small child with constipation problems. My mother would use a large rubber water bag with a four foot tube like hose with an end attachment. She placed Vaseline on the attachment, which was as narrow as my little finger, and pushed it three or four inches in my butt hole. She then released a clap and the water rush into my butt from the rubber bag that she held high.
The item before me was a model forty years advanced, but worked on the same principle, except it had a plugging device that forced the soapy solution into my ass. The instruction said to hold it in for five or ten minutes. I waited until I felt crapping and was no longer able to retain the quart of liquid.
I cleaned up and thought to put skin lotion on and place a generous gob up my rear, just in case.
The only time I wore makeup was when I was in high school or college plays and I put it on or someone else put it on me. I remember some of the techniques, but I had never applied lipstick before now. I watched my mom and my wife put lipstick on, so I had a good idea how to do it.
The red lipstick made my lips look fuller. I looked in the mirror and looked away. I wasn’t even close to being pretty. I looked like a naked guy with make-up on. I needed a wig or plastic surgery.
Finishing my self criticism, I took the tags off of the white satin panties and pulled them up my smooth legs, hips and genitals. It felt great. Size 2x was too small.
The panties were very tight around my waist. My hips were visible as were my balls and cock. My hips looked like a girls butt in the white panties. The garment felt soft, silky… sexy.
I reached for the white slip, somehow white seem coincidentally appropriate. I it pulled over my head? Tugging the slip over my shoulders was a little difficult, but it came down over my breasts, stomach, panties and thighs.
The slip was so tight my small breasts actual tented the material across my chest. My “breasts” were about three inches long and two inches high and stood out about an inch. My small, quarter sized nipples were elongated like a football and pushed against the silky satin.
Looking in the bathroom mirror, I could see curves in the right places, except for the bulge of my frontal package.
Somehow, the silky panties and slip made me feel feminine and sexy.
I wanted to be possessed and desired, touched and bonded intimately with another person all of which was lost to me in marriage by my mate’s unilateral decision not to be sexually intimate. Her fault, my fault, she decided, “No more.”
I took another quick look in the mirror and walked to the living room with as sexy a walk that I could with one bare foot in front of the other take short steps.
As I came into the living room and headed to stand in front of the couch, the satin fabric of my panties and slip sent chills through me. I began to become erect. Have you ever run silk or satin across your naked crouch? Well, you know the feeling.
John was sitting on the sofa in a bath robe. He was sipping some sort of drink and turned to watch me waltz in and station myself in front for him.
“You look so sexy,” he said. “The slip clings tightly to you and makes your breasts and ass stick out great.” “Here, put this on and pose for me” he said as he handed me a long, red hair wig.
I took the wig and placed it on my head and shaking my head back and forth causing the hair to move a few inches below my shoulders.
“Go over to the entry closet and look at yourself in the mirror. You look beautiful and so feminine.”
I walked over to the entry closet, walking sexy and purposefully trying to sway my hips. I open the closet door and a light automatically came on as I turned to look in the full length mirror on back of the door. Wow! What a change? I knew who I was, but didn’t.
I was attractive and could pass for female. The red hair wig flowed over my shoulders and bangs covered half of my forehead. I unconsciously began to run my hands over my chest, stomach, hips, thighs and back again.
“Come over here and pose for me,” John commanded. “I want to see you in your panties.”
I did my best sexy walk, swinging my hips as I walked the twenty feet or so back to the couch where John sat with a tent formed waist high on his robe.
I couldn’t believe that I was turning him on that I was sexually appealing to him or anyone. After twelve years of sexual rejections, I lost all confidence in ever appealing to any person again. Was I hot and hard!
As I reached the sofa, he put out his arms and I went straight to sit on his lap and his hardness. I felt his hard dick pressing against my butt. He wrapped his large arms around me and began moving his hands all over me, especially my breasts and thighs.
He leaned into me and kissed me on the lips. I never had a man kiss me on the lips. I hesitated until he began rubbing my cock that had caused the tent in my slip. I kissed back. It wasn’t that horrible. As he began to french me, I began to like it and returned tongue for tongue.
I wasn’t in control, John was. During all this, I felt his concrete cock pushing into my panty coverage ass crack.
He began to run his hands down my stomach and over my dick and on to my thighs, squeezing them. He slid his hand under my slip and proceeded to caress my balls and cock through my panties.
John pulled up my slip and brought it up carefully over my head. He leaned down and began to kiss my nipples and gently bite my nipples. I actually heard myself groan in pleasure as he administered to my breast with his tongue, lips and teeth as well as massaging my cock and balls.
“Stand up,” he said. “Turn around” “Those panties really look sensational on you, Sweetie.” “Back-up.”
I backed up feeling my calves against the sofa. John placed his hands on my panty covered ass and rubbed and smoothed imaginary winkles out of the material covering my ass.
“I am going to place one of the cucumbers you saw up your love channel, your new pussy. Before I take you, I don’t want to hurt you, so I am going to stretch your channel to eventually accommodate my dick. You will hold your cheeks together so the cucumber doesn’t slip out, while you are sucking my cock. Do you understand?”
“Yes, John, I will hold it in my ass while I am sucking your cock.”
“Good, now bend over.”
I bent over and felt him pull my panties down. A moment later, I felt pressure as he pushed a lubricated finger into my love canal. He began stroking in and out as he did before I took my shower.
After a minute or two, John removed his finger and inserted the narrower cucumber into my ass. It was wider than his finger, but not by much.
I could feel my rectum stretching, but felt no pain. He pushed the eight inch long, 1.5 inch wide vegetable into my willing rectum. He went slow pushing in a few inches then pulling back a little, pushing in more, then pulling back, pushing more and pulling back.
Within a minute, John had all but two inches of that cucumber in my ass and was fucking me with it. It felt great!
After three of four minutes, John stopped, pulled up my panties and said, “Hold that with your ass, turn around, get on your knees and give me a blow job.”
I turned got on my knees, held my cheeks tight around the cucumber and put myself between his legs. “I have never given any man a blowjob. I am not sure I can do a good job,” I confessed.
“Just do what you did when you sucked my finger and think about what you would want someone to do for you if they were sucking your cock. Place you hands on my cock through the robe. Now hold it and stroke it.”
I place my hand around a man’s dick for the first time in my life. He was huge. John was at least 2.5 inches wide and maybe eight inches long. I could barely wrap my fingers around his cock. I stroke him through his robe. I liked holding his dick and stroking it. For five minutes or so I stoked him slowly, squeezed his cock ever other stroke.
“Open my robe. Place your nose against my balls and breathe deeply. Take in my scent. Smell what a man smells like. Lick me as you smell my balls and taste me,” he said.
John had a decisive masculine odor, like a locker room after a long hard game filled with sweaty men. The wrinkle skin around his balls was stretched almost smooth and had hair all over. His balls tasted tangy and hairy.
I did not like looking at naked men, thinking they were ugly with the dangle between their hairy legs. Now, I can’t say I like the look, but the texture, taste, smell and touch were exciting.
After five minutes, I don’t know precisely, John said, “Lick my shaft and kiss it tip to balls.”
I was yearning to do just that. I was turned on and wanted to share passion and sex with someone. I licked John’s cock wet and kissed sucking kisses on the sides of his long, thick shaft. I frenched it with my tongue and lips.
I wanted to suck it and French his penis hole. I wanted to do everything I had read in Literotica as to how to suck cock.
It was as if John could read my thoughts through my desperate efforts of licking and kissing. “Now,” he said. Suck my cock, Sweetie.”
I almost forgot about my teeth scratching his dick’s slick skin when I eagerly place my lips over his cock’s head. I licked and sucked. I wrapped my tongue around his head. I pushed the tip of my tongue into his hole, as I sucked. I took perhaps five inches into my mouth, licking and sucking all the way, while holding and tickling his nuts.
After only a minute or two, John said, “You are doing so great! That feels incredible. Try for more.”
I love the feel of his cock in my mouth. It was hard, but soft. His cock was smooth and stout. His dick tasted slightly different than his balls.
I was moving my mouth over his staff up and down, fast then slow, slow then fast, up and down, as I was sucking and licking. I pressed myself to go down on John even more, but after another inch, I began to choke.
I had never deep-throated anything or anyone. I tried and had maybe six and a half inches in my mouth when I gagged as I sucked him into my throat.
“You are doing great for your first time. Are you sure this is your first time. Keep doing what you are doing.”
I wanted to please John, but I had no experience or practice deep-throating, so I licked and sucked and move my head up and down on his cock, while massaging his balls. This up and down, tonguing and sucking went on for 20 minutes or more.
I wanted to make him cum. I wanted to cause a person to have and share an organism with me. His balls seemed to swell as I sucked his massive cock.
“I going to cum, Sweetie, take in all. Shallow it for me. Oh, oh oh, aaahhhhhh.
John shot his cum into my mouth. I swallowed cum for the first time after he filled my mouth. He came so much more than I have been able to do in many years.
For the first time I tasted another man’s love juice. I have tasted my precum and weak, diluted sperm drippings during self gratification sessions after fantasizing about this very act.
But John’s cum was full of sperm. It had substance, even small chucks like a few bits of soft small cottage cheese in a sea of cum fluid. His cum tasted a little like salt water, yet slightly sweet and thick, not bad. I liked it.
I had made a man have organism in my mouth and cum. I liked it.
He came five or six times, as I continued to tongue, suck and swallow.
Before I swallowed the last shot of cum, he said, “Open your mouth and let me see my cum in your mouth.”
I opened my mouth and pushed out my tongue on which puddled a teaspoon full of his juice. He grabbed me and pulled me close to his face.
“Let me see you swallow.” I slowly pulled in my tongue, shut my lips and gulped down his cum.
He wrapped his arms around me and pulled me close, hugging me tightly and said, “That was tremendous, Sweetie, that was one of the best blow jobs I ever had. You will need plenty of practice, if you want to deep throat me and tickle my cock with your throat by humming or swallowing while my dick is in your throat. Would you want to do that?”
I was thrilled that he praised me, that he had sexual fulfillment from my oral administrations. I replied, “Yes, John, I would love to learn and deep-throat you whenever you wanted. I love sucking your big cock, feeling it stretch my lips and mouth. I like the taste of your cum and giving you pleasure. Thank you.”
“Well, Sweetie, your sucking my cock was worth more than the price of a pair of panties. Of course, you can do it again. But there is something else that I want to do, as soon as I gain my erection.
I want to fuck your boy pussy and cause you to come without touching your dick. Would you like that?”
I did not know what to say. Suck a giant cock was one thing but having it shoved up my ass is another.
“Yes, I think I would love it. But after seeing and feeding your cock into my mouth, I see the wisdom of your wanting to stretch my rectum. I am afraid your hard dick might tear me.”
“Oh, no, I don’t want to hurt you. Is that cucumber still in your ass? Take off your panties and bend over and let me use the cucumber in you. Get on your hands and knees, spread your knees apart and place you head on this pillow that I am placing on the floor.”
I got off his lap, took off my panties and assumed the position of bowing down, head down on a pillow.
John got on the floor behind me and slowly pulled the inch and a half, 8 inch vegetable back. He squirted some skin lotion on the green shining shaft of the cucumber and pushed it back in up to seven inches. He pulled it back and pushed it in, back and in, in and out.
He created a rhythm that felt strange but pleasant. He switch hands every once and a while and kept up the pace, alternating between fast and slow, deep or shallow.
Minute, after minute, I lost track, but I notice at some point I was humping that cucumber in an alternate cycle. As he pulled out I pushed in and as he pushed in I pulled back. I was moaning with lust, too.
Something was happening to my prostate and balls, I was beginning to develop love fluids and just before I came, John stopped and pulled the first implement of stretching from my butt. “Oh, please don’t stop, please,” I pleaded.
‘It’s Ok. I saw that you were really getting into the fucking and humping. I am glad you liked it, but we got to stretch you some more.
I am going to insert the larger cucumber. It is slightly smaller around than my cock by perhaps 3/8′s to half inch. (If you ever had something pushed into your rectum, 3/8′s to a ½ inch is huge.) This larger cucumber will stretch you and you may feel the stretch this time. I will go slowly. Tell me when or if it hurts.”
“John, before you start, may I have a glass of water or something to drink? The only drink I’ve had is swallowing your cum.”
“Sweetie, I am so sorry, you are right. I am so excited about making love to you that I forgot my manners. I will get you something and have a drink myself.”
After a few minutes, John returned with a large drink for me in one of those plastic, 32 ounce cups. He had a glass of some liquor or liquid.
When I took a drink it tasted kind of like Gator aide with something else in it. I gulped down about a third of the drink and asked what he put in the Gator aide?
John said, “Oh, did you like that special drink that I made for you?
“Yes, it kind of tangy when I swallowed, but it tasted OK. What is it, gator aide? I asked”
“No, according to some studies it is a better energy drink and it’s natural. I pissed in that cup to almost half full and then put ice cubes in it to make it cold. Take several more big swallows, Sweetie, and then we’ll resume stretching your boy pussy for me.”
Well, I was somewhat shocked, but I swallowed his cum, I swallowed a third of the cup of piss, already and I said it tasted Ok. So, I drank down another eight to ten ounces, got back on my knees and assumed the position.
“That’s a sweetie, Sweetie. Here we go.”
I felt the lubricated rounded smooth end of the large two inch plus cucumber being pushed against my ass bud. John pushed it slowly but firmly and steadily as the green monster began to enter and pass into my rectum.
It was stretching me, I could feel it taunt against resistant tissue, but it was not really painful, but it hurt a little.
“That’s it Sweetie, take it. Let it stretch you. Think about my cock entering you. Think about how much you want me to fuck your boy pussy. Think about how good it will feel. Think about having an organism from my fucking you.”
John’s words distracted me. They fed my many months of fantasies. I felt the massive vegetable go deeper and deeper into me. It felt tight. I felt my love channel stretching. I felt my sphincter taking the girth of the two plus inches as it slowing pushed into me.
“It’s almost all the way in, Sweetie. You took at least seven inches. You look kind of sexy with an inch of a large green cucumber sticking out of your love shoot. You took it well.
“You have been so marvelous since you agreed to let me see you in panties. You look so sexy, so feminine, and so desirable. You give great head and with practice you will be a great deep throater. How does it feel, Sweetie?”
“Oh, John thank you for telling me how well I am doing and how much you like and want me. Those are words and feelings that I have craved and needed for many years. I love your taking sexual pleasure and satisfaction from me. I think giving is receiving. My ass is sore, but not painfully. I can feel my rectum being stretched and my sphincter fighting to squeezing the pressure away. Thank you again for wanting me. I hope I am pleasing you.”
“Of course you are. You just needed someone to want you and take pleasure from your body as you receive pleasure. I am glad I caught you touching those panties and happy for your inner desire to be touch, kissed, and give pleasure. You will see what incredible passion, pleasure and sexual release you will experience soon.”
With those encouraging, flattering words, John began slowing fucking me with the large cucumber. As he slowly pulled it partially out of my canal, he squirted more lubricant on the cucumber and pushed in back in. In and out, in and out, in and out, he pumped me and pllowed me. He picked up speed and for some length of time he sawed at me with the cucumber.
As I got use to the size and the motion, once again I began to hump back and forth. I hummed and moaned. I panted and gasp for breath. Oh, it felt incredible. I have never felt anything with which to compare this feeling. I knew if John kept this pace I was going to cum on his carpet.
The thought jinxed my need and John stopped and slowly withdrew the large implement of transition.
“Well, do you think you are ready for me? How was that and how do you feel?
“Please hold me, take me, and make love to me. Let me feel your stiff, stout, shaft in my boy pussy. I want you in me. I need this love sex. I need to share my satisfaction with you and you with me.”
John moved in beside me and put his arms around me and held me. “I will make you mine. White panties and a white slip is a symbol of your being taken for the first time. I will have your cherry and come deep, deep into your love channel. Do you want me to take you?’
“Now, I pleaded. Please I thought about this, fantasized about this moment for months and subconsciously probably for years. I need to be taken. I need to give and receive sexual release. I need to be desired and taken. You chose me, thank you. I need this. Yes, please!”
This man picked me up off the floor and carried me like a bride over the threshold into his bedroom.
He placed me on the bed, took off his robe and for the first time I saw John completely naked. He looked strong, masculine, attractive, and sexy.
This hunk wanted me. He had a large chest which was very muscular. John had hair on his chest, arms and legs. He was much hairy than I ever was. He had powerful legs and a small flat ass.
He was a naked guy that I was staring at. After his prior touches, kisses, massages and my tasting, smelling his balls and cock and swallowing his scrumptious cum, I like what I saw. I needed him to want me and to take me.
“I am going to sit on the edge of the bed and I want you to straddle me, placing your knees on each side of my thighs. Once in position, I want you to lower yourself on to my cock, so you can gauge how much and how fast you want to push my cock into your boy cunt. Can you do that?”
As John repositioned himself on the edge of the bed, I thrilled, “Yes, oh yes, that would be so nice. Thank you for this gesture of not wanting to hurt me. I promised to please you. Are you ready for me to squat over your beautiful cock?”
I came around to the edge where John sat with the back part of his knee and hips on the bed and his lower legs against the side of the bed. I climb on to the bed with my knees touching next to his lower waist or upper hips.
As I hovered there, He leaned in and kissed me as he wrapped his strong muscular arms around me for support.
I lowered myself on to his eight inch, 2 and a half inch thick, strongly erect and hard as steel cock. His dick head past my crack and tickled my anus. I push down with some determination and John’s well lubed cock pressed through my sphincter muscle.
John was very wide, but the stretching did its job. There was a little smarting, but not really pain. I pushed on and three inches of John’s giant dick slid in.
He kissed me and said, “O, o Sweetie that feels sooo good. You are so tight.”
I continued pushing my boy cunt onto his cock slowly but steadily. I was pushing myself to a new way and sexual fulfillment for John and me.
In two of three minutes, maybe more, or less, I was sitting on John’s thighs. His dick was pressing inside me and I felt filled. I was stretched more than ever, but I loved it.
“Sweetie, Oooo, Sweetie, Oh, this is indescribable. Let’s hold here until you are ready for motion and a good fucking. What are you thinking, Sweetie? How do I feel inside you?”
“John, John, I never experienced this before. I have never sucked cock; swallowed cum. I have never been fucked. You have taken my innocence. I feel so sexy. I feel so wanted. I feel like I am giving you pleasure and receiving in return. I am smarting, but have no pain. Your strong arms around me feel wonderful. Your concern for how I feel moves me deeply.”
With those words, I begun to push up and off his cock and then let myself down. I slowly began to fuck myself and John as I moved up and down on his large swollen cock.
After five or ten repetitions, I increased the length of pulling in and out and the speed of doing it.
John began to move on his own, bouncing in and out, in and out. He rotated a little as he bounced up and down inside my pussy.
While we stroked and bounced together, John began to kiss and suck my breasts and nipples.
I did not know until that afternoon that my nipples were an erogenous zone on my body. John bit my nipples again and again.
Oh, the combination of his manificent cock plunging in my ass and sucking and biting my nipples was ecstatic and electrifying.
While bouncing and fucking, kissing and biting my nipples, he moved one hand on to my swollen dick, at this point maybe six inches long.
Being fucked by John increased the size of my erection. He began to masturbate me. Wow!
What an experience and flood of feelings and passion! We moved together for a very long time or short time. I was lost in passion.
John said, “I am going to come in you, but I want to do that in the missionary positions. Ok?”
“You can have me anytime, anyway, anywhere, I declared. John you are so wonderful, I never thought someone would be intimate with me in any way and especially sexually intimate with me again.”
“I want you to lift yourself off of me and lay on your back with pillows under your hips with your knees drawn up close to you chest and leg spread wide, he instructed.”
I did as he asked and lay there waiting, wanting, needing him to enter me again and cum inside me.
He crawl between my knees and placed his large hands on each side of my chest between my breasts and arms. He entered me. There was no resistance. There was no pain. It was marvelous to be taken.
Then he began to move. He thrust forward and back. His dick was like the steel rod on a locomotive’s wheel, plunging back and forth, back and forth inside my, his love cunt.
I moved with him. We were a pumping machine and then…
He came. He came hard and often. I would feel the impact of his cum hitting the walls of my canal.
He panted and groaned. He kissed me deep and long and I came too.
I don’t know how but as he spurted within me, I came. I shot sperm and juice, not much, but more than I ever had while servicing myself. I came on my stomach and his. Our movement smeared it around on our bellies, legs and chests.
Filled and fully spent, we just lay there, both exhausted. His once rock hard dick slip from my ass, but John held onto me, kissing and petting me and me him.
There was a price I paid to be here and to have this. I could not find the intimacy I craved at home. I could not have a woman. I just did not want to be rejected by a woman, any woman, again.
My mind and focus changed. If I could be sexy and desirable, if I wore panties and lingerie would someone want me? The Literotica stories poured gasoline on my fire, printed fantasies and thoughts imprinted my brain and changed my drive.
There had already been the civil ceremony with family and friends present and it was a great occasion, but what Jo and Roger had both really been looking forward to was the other ceremony, the secret ceremony. Here is the order of events for that special occasion:
11am Trinity, as priestess, in head-dress and black silk robes, asks the guests to rise. The slave is called in. He stands in front of the priestess.
Trinity: “Are you slave roger?”
Slave: “I am, Madam.”
Trinity:”Are you here to become the property of Mistress Josephine?”
Slave: “I am, Madam.”
She orders the bridegroom to strip naked. Sarah in girlie pink mini-dress and white stilettos, steps forward to take his clothes from him, as he disrobes. Trinity’s sissy maid then steps forward and attaches chains to the slave’s ankles, wrists and thighs. The priestess orders the slave to lie face-down on the floor.
Beautiful music starts to play. From his position on the floor, the slave can see nothing, but he knows that it is at this point in the ceremony that his Mistress will enter the room. He knows also that – as part of the ritual – his Mistress is going to step on his back.
Josephine, looking quite stunning in flowing purple satin, enters the room. In her hand is a bouquet of lily-of-the-valley interspersed with young, fresh nettles. All eyes are upon her radiance.
She walks up to the prostrate form of her slave, brushes her bouquet down his back and leaves it resting on his buttocks. It would not do for her accidentally to sting one of her guests. She takes her time greeting the congregation: she hugs Tim, who has come all the way from Malaysia to be there. For that reason she decides he deserves a friendly squeeze of the goolies as well. She looks at the hired stud, whom she has never seen before, but who, she knows, will be part of the ceremony. He looks rather dishy in an obvious sort of way, she decides. It is a strange thought, she muses, that the man, with whom she is going to be linked in this ceremony, the man lying naked, face-down on the floor, has paid this gigolo to be present.
But the man on the floor is of no importance at thos moment. She loves him. He loves her, but for this relationship to have the magic she wants, she must ignore him for the time being. She gives Andrea, her beautiful transvestite friend, a kiss, commenting on the outrageous bridesmaid’s outfit she is wearing. Surreptitiously she gives Andrea a little squeeze between the legs as well.
“Are your panties a little tight, darling?”
Jo cannot help thinking, “Vanilla people have no idea what they are missing.”
She walks towards Trinity, the priestess. Her journey takes her across the back of something lying on the floor. Oh, yes. It is the naked back of her fiancé. She does not even look at him, but moves straight to Trinity, giving her a full, warm kiss on the mouth.
Trinity lets the kiss linger briefly, then – resuming her officiating role – addresses the guests:
“We are here to solemnize the union of this slave (she nudges Roger’s prostrate body with the toe of her stiletto) to his Mistress, Josephine. Are you, Josephine, willing to accept this person (another nudge with the toe of her shoe) as your devoted slave, to serve you, worship you and obey you?”
The priestess continues: “The slave will rise to his knees.”
There is a slight rattling of his chains, as the slave kneels up and beholds his dazzling Mistress for the first time today. She looks at him with a loving smile and her deep, dark eyes see into his soul and she knows therefore that for him today is the most important day of his life.
“Do you, slave give yourself totally to your Mistress?”
“Will you serve her, obey her and worship her?”
“Will you do all in your power to make her life happy and comfortable?”
“Do you renounce all other sexual liaisons, unless they are specifically commanded by your Mistress?”
“Do you understand that your Mistress may take other lovers, if and when it pleases her to do so.”
“You will now solemnize your vows with the servile libation.”
The priestess hands the slave a silver goblet. Standing either side of his Mistress, her two handmaidens slowly raise the hem of her wedding dress, revealing her nakedness beneath. She parts her legs. The slave knows what he has to do. He holds the goblet between her thighs.
With great self-control his Mistress releases just enough of her sacred nectar to fill the chalice. The slave drains the goblet. There is applause from the congregation.
The Mistress whispers the word, “dab”. The slave proffers his tongue. The Mistress uses it.
The priestess speaks: “The slave will stand.”
From a silver tray the priestess takes a stainless steel male chastity device. Skilfully she locks it around the slave’s cock and balls. She removes the key. Jo opens the locket on her necklace. The priestess places the key in the locket, which she snaps shut.
“The slave will kneel again.”
The stud steps forward to stand in front of the kneeling slave. He unzips his fly and presents his cock to the slave’s face. The slave respectfully puts his lips round the stud’s erect penis. This action is purely ceremonial and the stud withdraws again, moves over to the bride and , taking her proffered hand, leads her to the four-poster bed. The stud and the Mistress climb on to the bed and close its curtains.
Music is played and champagne is served to everyone except the slave. He has already had a drink.