sex at work
Taking a new job was stressful. I felt very nervous, unsure of myself, sick feeling. I needed this job for financial reasons, so I wanted to do my best and make a good impression. As we walked around the plant to meet everyone, I noticed this guy standing at his machine. He was tall, muscular, and build like a brick shithouse. Mmmm, I thought, which made my face feel flushed, hoping no one noticed. He was sweet, respectful, but playful at the same time. True Souththern gentleman, I thought. As he spoke I noticed his features, his big brown eyes, dark hair, the outline of his body. My panties were wet, just looking at him. Mmmm, I thought..what a wild ride he would be. I had visions of sucking his cock, fucking this man I didn’t even know, but just the site of him made me think of things I had long forgotten. But as usual, the guys I’m attracted to are always taken. Such a waste, I thought.So thinking nothing more, I started my job.
Weeks passed and Steve and I became good friends. I really liked him a lot. I realized that he wasn’t only a good machinest, but fun to be around. We exchanged cell phone numbers for work, which I was grateful in knowing that I could call him with questions. Doing a good job was most important to me. I wanted to be a good worker, dependable. He always helped me find my way around, explaining my tasks, and made me familiar with “plant” politics. He was flirty, but cautious. But I kept having visions of him deep inside of me on the greasy floor in front of his machine.
I realized, as time went on, that we had a lot in common, we both loved the same music, classic trucks, to drink cold beer and good moonshine. That made me so dam hot. My little pussy was soaked every day with naughty forbidden thoughts of him. I’d then try and focus on my job, thinking I had to control myself, but found myself fanticizing about him fucking me at his machine, in a king size bed, or sucking his hard rock cock in men’s room at work. It didn’t matter where or what we did, I just wanted him. He seemed to like me too, which made it hard for me to concentrate, with his flirting, innocent teasing, and pushing the envelope. I did this too, testing him to see how far he’d go. I really wanted to get to know him better, but I didn’t want to come across as desperate or a pest not knowing if he really wanted to play. So, I treaded lightly. I grew up being a loner anyway, always keeping to myself, resigned to the fact that most guys didn’t have a clue anyway and my last relationship ended so badly I wasn’t willing to do that again anytime soon.
Then one day, Steve and I started texting, teasing each other, then things got steamy. I had wanted this for a long time. I realized that he was just as hot for me as I was for him, wanting to fulfill a lot of the same fantasies, sucking his cock, fuck for a entire weekend, drink moonshine and get wild. Our texts were something out of an erotic story, not for the faint of heart, taboo fantasy at is finest, almost unbelievable. I had never met a man that thought like me, with the same fantasies of nasty places to have sex, or forbidden sex that most just dream about. I knew that Steve was no ordinary boring guy. He was different!
For weeks, we text back and forth. I was so hot for him that I could barely stand it. He was all I could think about and possibilities of what I wanted to do to him were endless. At work it was all that I could do to not walk up to him, unzip his pants and take hold of his cock. He called me his nasty little whore, which sent waves of excitement through me. No one had ever called me that before and he told me I was his “baby girl”. Which took me from one extreme to the other. He quickly became my “daddy”, which having forbidden sex with my daddy excited me. He told me what he intended to do to me and how he was going to do it. Never I read such ambrosia. We discussed the idea of taboo sex and roll playing. I knew I had to have him and soon!
Then we got our chance. He had to be at work at 3am! Excited, but nervous, I drove to meet him. We didn’t waste any time. I wanted this night to be totally about him. He led me straight into the men’s room and closed the door. I reached out and stroked his cock, looking in his eyes. Pulling me to him, he kissed me hard and deep, letting me lightly suck on his tongue. Mmmm, he is delicious I thought. Then unbuckling his pants, he let out a little moan of anticipation. He softly pushed me to my knees onto the filthy greasy floor, slid down his pants revealing his stiff cock. Mmmm, we both moaned. He took his cock in his hands and pressed it against my lips. I slowly opened my mouth. Mmmm, I softly licked, tasting his sweetness. I wanted to savor every minute of his delicious cock. He held on to it as he guided it into my mouth. He started slowly fucking my mouth -just as I wanted, pulling my hair our of my face, watching me sucking and licking his rock hard cock. I had my hands on his ass, feeling his skin, letting him fuck me. I felt his cock harden as I relentlessly sucked wanting every inch. I could feel his breathing change and his soft moans of excitement. I could feel him watching me enjoying sucking his cock. I wondered what he thought as he watched. “Baby I’m about to cum!” Steve exclaimed as I felt his body tense and with his hands in my hair, he buried his cock deep in my mouth shooting his thick white load down my throat. I tasted his liquid, as he kept cumming, I caught every bit in my mouth, swallowing every drop.
We quickly got his pants back on and it was time for me to go. Living out our fantasies together was going to be fun. This was just the beginning. I could tell that he wanted more and I couldn’t wait.
Our first New Year’s celebration after leaving Germany was, as it turned out, surprisingly eventful. Mandi and I had stopped in a small bar close to the Interstate highway, owned and operated by a Korean woman. She was tough but nice, and was generous to people who frequented her bar, especially couples who could be considered regulars.
We went there about once a week to drink a few beers and shoot pool. One evening in late November, when we were sitting at a table close to the fireplace, right after I had stirred the fire and added some wood, she came over to our table. I figured she would just do her usual chat for a minute, and move on. This night was pleasantly different.
“You guys are new, but I like you. You come here and have a good time, and don’t cause trouble. You dance sometimes. That’s nice,” she told us.
I thanked her and said we enjoyed her place, especially sitting with a cold beer by a roaring fire. As I spoke, she was digging into a pocket of the tunic she wore. She pulled out something in her hand and offered it to Mandi. It was two small, homemade tickets of some sort.
“We have New Year party here!” our host explained. “Plenty food, free beer, big party. You invited.”
We were slightly surprised, but gratefully accepted her invitation.
“Thank you,” I said, “We will definitely be here.”
We enjoyed the fire and talked with a few people, and went home. We returned a few more times before New Years Eve. Then the big day occurred.
It just happened to be a Sunday, and here in God’s country polite people didn’t drink on Sunday, thus the locked door and free party. We arrived about 2100 and the party was just beginning to kick. We had to knock on the door, and after it was opened a crack, a face partially hidden by the door asked for our tickets.
I offered them and saw an eye carefully scrutinizing them. The door closed almost shut for a few seconds, and then another set of eyes appeared, only to have the door swing open and our hostess appeared.
“You come in!” she cried with outstretched arms.
We entered and exchanged hugs as the door was bolted shut behind us. There was a decent crowd, not too many people but enough to have a kicking good party. We grabbed a couple of beers and hit the bar, where there was a buffet line of food set up. Our hostess had made a bunch of Korean food, including some delightful egg rolls. There was plenty of kimchi, and we helped ourselves to as much of the food as a plate would hold.
After grabbing an empty table, we dug into the food for a while, and enjoyed the music. We started dancing a little while later, and while dancing, accidentally and literally bumped into another couple. We stepped back and shared a laugh and went back to dancing. Then, for no apparent reason, we bumped into the same couple again. We backed away laughing and decided that the dance floor wasn’t big enough for the both of us.
Mandi and I bowed out and went back to our table. As we continued to eat, the couple we banged around with came over and asked if we wanted to join them. Since we weren’t really acquainted with anyone else at the bar, we decided that it would be fun to meet someone new. And with that, we moved over to their table.
The couple was Chuck and Wilma. It was the first time I knew anyone named Wilma, with the possible exception of Fred Flintstone’s wife, but that was her name. She was well built, nice plump tits, nice ass, and Chuck was tall, somewhat heavy but in reasonably good shape. He had a slightly brushy beard and longish hair. Wilma had auburn hair that was obviously enhanced from a bottle, but was really nice looking. She turned out to be in her early 40′s and Chuck was about 5-6 years older. She really liked dancing and kicking up her heels and he was pretty laid back.
When Mandi got tired of dancing, Wilma asked me to dance, so we jammed around the floor for a while, and then when they put on some slow music, I danced with Wilma while Chuck and Mandi took a slow tour themselves. Wilma had a pretty nice body, and I found myself getting horny from doing a slow jam and grinding my crotch into hers as we danced. I started getting hard, and she felt it and got even friendlier, grinding back with a passion.
This went on for a while, off and on until midnight when we all celebrated the New Year. Sometime before midnight, we decided that we should go back to our place since their kids were already taken care of, so not long after we saw in the New Year, we headed out. Mandi rode with Chuck and Wilma rode with me so if we got separated, we didn’t have to worry about finding our house.
We just got started when I reached over and grabbed Wilma around the shoulders and gave what was supposed to be a hug. She leaned toward me and kept going, right into my crotch. She had my cock out of my pants in seconds and swallowed it. This made driving a bit difficult, and I had to concentrate on driving just to keep from killing us. We managed to get to the house in one piece. Mandi and Chuck had already gotten there, and had gotten some drinks and beers out. We put on some music and danced a while, slowly slipping out of some of the clothes.
Mandi and I had partied and swung with some other couples before so this wasn’t our first time. It was for them. Wilma had a private conversation with Chuck and soon we had split off. Wilma and I danced to some hot music and stripped each other naked while the song played. Chuck and Mandi went into the kitchen and were playing grab ass. She was kinda mediocre about Chuck, but he seemed okay, and Mandi was in a party mood anyway.
While they started getting naked in the kitchen, Wilma and I hit the floor and I slipped into her so easily I thought we were a well oiled machine. We fucked on the living room floor for a while, and then Mandi and Chuck came back in, naked except for Chuck’s t-shirt, and he laid down on the floor and pulled Mandi on top. They did some slow moves for a while, and since the floor was getting a bit old for me I wanted something more comfortable to lie on.
Wilma and I moved to the den and got comfortable on the futon, fucking away like old lovers. We jumped into a 69 for a while, I fucked her from behind, and she had a couple of nice orgasms. Since I had quite a bit of alcohol, I had trouble getting an orgasm. But Wilma was a hot older babe, and she didn’t want to quit, so I was cool.
After a while, I asked her if she was into anal sex, and she said she hadn’t done it before. I got some lube, and got her to lay down on her stomach. After greasing her tight back hole with first one, then two fingers, she seemed to be okay with anal play.
I eased the head of my cock up against her ass. We didn’t have the lights on but I could feel it slipping right into the tight ring of her asshole. She stiffened up for a second, and when my cock popped in past the head, she squirmed in pain. I tried to get her to relax a bit, and she seemed to for a minute, but as I tried to push further into her ass, she balked and pulled away.
“It hurts too much,” she complained.
I tried to reassure her that it took some time, and she swallowed another drink and gamely offered her ass to me for one more shot. I used my fingers again, gently massaging her anus with well oiled digits. She told me to try again, but when I began to push in she still had problems, so I finally gave up. We relaxed for a few minutes, and went back into the living room. Chuck was still on his back and Mandi was doing a slow ride on him. I got another beer, and told them I was ready to crash, and Wilma and I left for the guest room.
The next morning I woke up with a bit of headache, and it took me a minute to realize what had transpired the previous evening. It didn’t take long, though, when I saw the auburn hair peeking from under the blanket. I had a raging hard on, and thinking back about Wilma’s ass made it worse. Just when I thought I would bust, and gentle hand wrapped around my cock and began to stroke it gently.
After a little of this, I saw a lump moving under the covers, and then a warm mouth sucked in the head of my cock. This time, Wilma took her time and slowly and carefully began to take a bit more of my cock at a time until she had pretty much gotten most of cock down her throat. Mandi was pretty good at giving head but this was really special.
Wilma slobbered and sucked on me for a few minutes, and then began playing with my asshole. As she stroked my back hole, I finally got the urge to come, and within seconds, blew a huge wad down Wilma’s throat. She gamely swallowed as much as she could, spilling a little on my legs. After this, I lay there panting and took a few minutes to recover. I returned the favor without a word, diving into Wilma’s pussy and eating her to a killer orgasm within minutes.
I got up and wandered off to the bathroom. When I went in the living room and looked out, Chuck’s pick-up was gone. I peeked into the bedroom and Mandi was alone under the covers, gently snoring away. I grabbed a beer, and some coffee for Wilma, and returned to the den.
As she sipped her coffee, I told her that Chuck had already left. She had planned a meal for some friends that evening and invited Mandi and me over for dinner. After just giving me a great blow job, though, she acted so shy when she headed for the bathroom, grabbing a blanket and wrapping up. While she was in the bathroom, I got dressed into some sweats, and when she returned, she asked me to take her home.
We drove to her house in almost uncomfortable silence. I finally broke the spell by telling her how sexy she was, and that she was the first woman that much older than me that I had sex with. She laughed and told me she had never had sex with anyone younger than she, and we laughed at the thought. About the time we got to her house, she leaned over and tweaked my crotch, told me she had a great time, and insisted that Mandi and I come for dinner that evening. I told her we would.
Mandi was ready to kill me! She was cool with Chuck and was getting into a strange fuck when he began mauling her nipples. When he actually pinched them, she got mad and slapped his hands away. He told her she shouldn’t be so bitchy since she was just a slut who fucked other guys while her old man fucked their wives. She had gotten off him, gone into the kitchen and grabbed my chef’s knife and came back in the living room and asked him if he wanted his hard-on sliced off.
He tried to raise up like some kind of redneck badass, but Mandi was ½ American Indian, and had a temper showed it. Chuck decided he would let discretion be the better part of valor and split. That’s when Mandi heard me and Wilma still going at it and went to bed.
I was almost afraid to mention the invite to dinner, and when I did, she said she didn’t want to get around a crude redneck bastard like Chuck again. She told me that we shouldn’t piss them off after what went on, though, and told me to go and offer her apologies for drinking too much and having a killer hang over. She would stay home and get some rest and maybe take the dog for a long walk.
I went on over to Chuck and Wilma’s for dinner, met the kids, met the friends, enjoyed a good meal, and drank a few beers. When I got ready to leave, Wilma walked out with me.
As we started down the walk to my car, she said, “I don’t think Chuck treated Mandi very well. I know how he is, and he was being a shit. He wants to try to swing with people, but he is way too jealous and he just gets angry with whatever female he can take it out on.”
I pondered this for a moment as she continued. “But if you want, I would like to get together with you on our own.”
I looked at her for a second before realizing what she said.
“Just the two of us?” I asked.
“Sure. Besides, I want you to teach me how to do that in my bottom. It hurt, but it is so dirty I got turned on by the thought, and I want to learn how to do that. Do you think you could teach me and get me to where it didn’t hurt?”
Well, an old horny butt bandit like me couldn’t resist this invitation and I told her, “I think I could do that.”
She laughed a low laugh, and turned toward me, reaching down with a hand between us to grab my cock.
“I can’t wait,” she said succinctly.
I gave her my work phone number, and she told me that Chuck drove a truck and was often gone for 3-4 days in a row.
“We can have some fun,” she said with a smile.
I left with a hard on and went home.
We actually got together alone for the first time about three weeks later. We had a good fuck on her bed, and Wilma was a willing if physically unable participant in anal sex. She just couldn’t seem to relax and loosen up enough to do more than get a pain in her ass.
I told her that maybe she could use some toys to loosen her up slowly, and when Mandi and I were down in the closest decent town, I slipped out while she was shopping to ostensibly grab a beer but also stopped by a sex shop and got Wilma a selection of sex toys.
She had a vibrator, but I got a couple more, a butt plug kit with different sizes, and as I was browsing, found the kicker, a latex panty imported from Europe that had two molded dildo-like probes for pussy and ass, and a small ridge to rub the clit of the wearer. The panty had been cast from latex rubber, and the probes and panty made a single, continuous piece.
Once emplaced, one simply poured some light sex lubricant into the panty and either walked around, exercised, bicycled, rode a horse, or did something else physical to make the probes move in and out of the pussy and ass and the clit ridge would stimulate the clit.
Wilma was almost aghast at the dildo panty when I showed it to her, but she was also a bit curious. She also liked the rest of the toys, and promised to use them. We got together for a couple of more sessions and she showed me how much fun some of the toys were, and she had me fuck her doggie style while she had a small butt plug in her ass. She got a killer orgasm from that one.
We would meet about once a month for a 2-3 hour session when I was able to get away from my training site early. Mandi watched her soaps in the afternoon when she wasn’t working, and didn’t like to be disturbed, so I didn’t tell her what time I actually got away from work. Wilma worked hard to get her butt hole loosened up for me to actually fuck, but the process was slow and painful. She worked hard getting her tight little hole to loosen up for me, and got to the point where she absolutely loved having me play with a probe in her ass while we fucked doggy style.
I was at work early one afternoon after the site was cleared of people, finishing up my training reports when I noticed a car pull up in front of the facility. I didn’t recognize it at first until I noticed a female get out of the car. It was Wilma. I thought this was a bit odd, but I welcomed the interruption since I was in no hurry to head home and had left one of the simulators running so I could do some shooting after I finished my reports.
As she came down the walk to the front office, I notice that she was walking rather gingerly, like she was sore or something. She was wearing a short denim skirt and a bright red blouse, sleeveless and opened at the neck. She was also wearing some red pumps. As she got closer, she looked a bit flushed.
She apparently didn’t see me sitting at the desk, even though the window was open and I could see her easily. She knocked on the door, and I told her to come in.
She slipped in the door, looked at me and said, “Is anyone else here?”
“Nice to see you too,” I replied, “and no, no one else is here. Why?”
She smiled and moved over to my desk, set her hands on it and leaned over to kiss me. I gave her a quick kiss and noticed she wasn’t wearing a bra and her tits were exposed from 4 buttons open on her blouse.
“Nice view,” I said, “Is that for me?”
She laughed and said, “Sure. And I have a surprise for you if you have a little time.”
Mandi wasn’t due home from work for another two hours and no one would be showing up at the site for about 3 hours for remedial training, so I was up for a surprise.
“I have some time. What’s the surprise?”
She laughed and said, “You’ll see. Now why don’t you show me around this place?”
I told her there wasn’t much to see, but if she would give me a minute to finish my reports I would. She asked if I had a ladies room, and I pointed her out in the hallway to where she needed to go. She walked away in that funny, slow walk, and came back about 5 minutes later as I was finishing my reports.
“Done yet?” she asked.
“That I am, let’s go,” I replied.
I decided to shut the windows and lock the door so I wouldn’t be interrupted accidentally, and we headed over to the left side of the building. It was actually a couple of large Quonset huts joined by a concrete block building in the center. We walked out in the open bay, mostly dark, lit only by the light that seeped in through the floor level vents. She looked around and noted the low lecture stage across the front.
“What’s that for?” she asked.
“That is where we brief each class on their training, and also give some classes.”
“Oh,” she said and slowly looked around.
Then, after a short pause, she turned and wrapped her arms around my waist.
“Are you sure you want that surprise?” she asked.
“Sure,” I said.
“Well, I am so horny I am running juice down my legs. I need someone to lick me clean. Can you help me with that?” Wilma asked.
“Oh you bet,” I quickly answered, “that sounds like you have an emergency on hand.”
“I do,” she laughed, and began to rub my cock through my uniform pants.
“And I need some help with something else.”
“What’s that?” I asked.
She took my hand and pulled it down to her thighs. I rubbed her bare leg below the skirt and she pushed my hand up under her skirt. I thought that she was definitely in a hurry so I ran my hand on up her thigh to her crotch, half expecting her not have any panties on, only to be blocked by a the feeling of rubber. I stepped back in surprise and then it dawned on me. She was wearing the dildo panties!
This was an unexpected delight, and I asked, “So when did you decide you would wear my little present for you?”
She laughed lightly, grabbed my hand and pushed in harder into her crotch. I took the hint, and began rubbing along the center where the clitoral knob of the panties would be, and she responded with a moan.
“I thought maybe I would try them out today, and decided I liked them more than I thought. They were nice after I finally got them situated. And after I moved around a bit in them they made me really horny. So I decided to surprise you and see if you would like to take them off me. I had an orgasm while I was driving over her and almost ran off the road.”
I chuckled and said, “Better be careful where you wear those. It could be dangerous.”
She pushed against my hand and said, “Rub a little harder.”
I massaged into the neoprene surface, and watched her breath quicken until she finally burst into an orgasm.
“Damn, these things are so much better than I first thought. When you gave me these things, I thought you were crazy. But the more I thought about it the more I figured I would give them a try. And you were right about the best way to put them on.”
I would like to have seen her wiggling around and getting the two molded probes into her pussy and ass, but there was time for that later. I had another idea in mind.
“So you got the back one in without a lot of problems?” I asked.
She chuckled again, and said, “It hurt a little at first, but I used some nice flavored lube and slowly worked both in at the same time. After I got them part of the way in, I peeled the upper part over my legs and then pulled them the rest of the way up. After I sat on my stool, both dildos went all the way in and have been there ever since. The one in my ass is still a little uncomfortable but I think I’m getting used to it.”
I liked the sound of that, since I was trying to be patient but really wanted to slam fuck that nice ass of hers.
“Well what say we get you out of them now and see if I can’t take care of your little problem!”
She laughed and said, “Sounds fine to me.”
I led her over to the platform and pushed her gently back onto it, laying her backward until her ass was hanging over the edge. I made a note that it was perfect crotch height. I pushed her skirt up and reached to the top of the panty, and began to slowly peel them down, turning them inside out as I went.
I got them past the level of her pussy when she squirmed a bit and said, “Be careful. Take them off real slow.”
I obliged and very gently eased them slightly down on her thighs until I could see the base of the probe in her pussy. I reached down with two fingers, and began to slide them out of her pussy and ass. I pushed the panty down a little further and finally freed both probes from their former hiding spaces. I finished slipping them off her legs and held them up. With them inside out, both probes stood straight up in my hands.
“Wow,” she said, “I feel suddenly empty.”
I laughed and said, “Come on. I have a surprise for you.”
I took her hands and helped her back to her feet, and we headed into the other side of the facility where the simulators were. It was dark in there as well, except for the machine I had left running.
The shooting simulator could be used in both the standing and prone shooting positions, but we generally left it standing. I carefully moved the weapon off the machine and placed it on some chairs beside the machine so I didn’t stress the joint on the recoil rod. She watched me curiously but quietly, and I retrieved a couple of more sandbags from another machine, and placed the sandbags on either side of the shooting area.
After I had things ready, I took her hand, backed her up to the machine, and lifted her by the waist until she was sitting on the platform. I told her to lay back on the platform, and pulled her toward me slightly and placed her legs on the sandbags on either side of the shooting position. I was face to face with her juicy pussy.
“Pull your tits out and play with them, “I told her.
She complied and I dived into her pussy, wasting no time in getting to her clit. I worked her clit into my lips and pushed it back out with my tongue, and got into a rhythm while she mauled her tits and moaned. I felt her building toward an orgasm, so I kept the rhythm steady and pressed my lips in a bit harder.
Just before she could launch into an orgasm, I slid two fingers into her pussy. This gave her a new stimulation and she moaned louder. After a few seconds I added a finger to her asshole, and finally added the last of my fingers to her ass, and began pounding my fingers into her like she was getting double fucked.
She jerked once, then twice, and let loose with a loud moan, writhing around on my hand and after a couple of more spasms, relaxed on the platform. I kept gently kissing her pussy and slowly probed with my fingers, until she finally raised her head and looked down at me with a grin.
She blurted out, “Damn, you have the knack for doing the right thing when I need it!”
I laughed and replied, “Glad I could help.”
She pushed herself up on her elbows and said, “If you’ll pull your hand out of my stomach and get me down, I think I want something bigger than fingers in my pussy.”
“Whatever you say,” I said, and after pulling my fingers out, I helped her down.
She held on to the side of the platform, still a little unsteady from the orgasm, and watched as I moved the sandbags back to their normal position and put the weapon back. I took her hand and we walked back to the other bay, and I slid her back on to the lecture stage again so she hung out over the edge as before.
I had a raging hard on in my pants, and I didn’t bother to take them off, especially with the combat boots I was wearing. I unbuttoned my pants and whipped my cock out into the cool air, and with no hesitation, suddenly plunged into her sopping pussy. She reacted with a quick groan, and then started moaning.
As I slid my cock in and out, I told her, “That pussy lube you used tasted good.”
I smiled at her and licked the fingers I had been probing her pussy with. I tugged her blouse open, unbuttoning the last couple of buttons and mauled her tits as I slammed into her pussy. She bounced her ass and moaned some more, squeezing her eyes tightly shut. This went on for a while until she finally opened her eyes, and I could feel her building toward another orgasm.
I slid a thumb down to her clit and gently massaged it until she rocked through several spasms, softly saying, “Damn, fuck me……fuck….shit this feels great….fuck me…..harder…..harder.”
She finally finished and relaxed, and looked at me.
“Aren’t you going to cum?”
I chuckled and said, “Remember, my job is to get you to where you can handle a cock in your ass. Are you ready to try again?”
She looked at me and said, “Well, the panty hurt a little and it isn’t as big as you, but I guess we can try. Do you want me to turn around?”
I thought about it for a minute but told her, “No, just stay like this. It might be easier for you.”
“Ok,” she replied, “be slow and gentle.”
I kept up the motion with my cock in her pussy for another minute until she settled back and relaxed. Staying in her pussy, I reached down under my cock and found that she had dribbled lube in her asshole and on the front of my pants! No time to worry now though, so I slid my cock out and slowly rubbed it around her crinkled little asshole. I pressed in slowly, and she began to moan again, this time without much pleasure.
“Easy,” she said.
I kept an easy steady pressure until I finally slipped into the tight ring of her asshole.
“Ow,” she cried, and I stopped moving.
“Don’t move and try to relax,” I told her.
“I’m trying,” she said, “but it hurts.”
I remained still, feeling her alternately grip and loosen her asshole around my cock. Finally, I eased a bit more into her ass. She had her eyes shut again, and I reached out and held both hands. She gripped my hands tightly and moaned again as I slowly pushed more cock into her ass.
As I began to withdraw the 3″ I had eased in, she moaned again and said, “It still hurts too much.”
“Try one more time,” I asked,” and try to relax some more.”
“I’m trying,” she complained,” but you’re too big for my ass.”
I chuckled and said, “Thanks, but I can’t make it any smaller without it getting soft.”
She writhed in pain as I tried to add a bit more of my cock to her ass, and finally said, “It still isn’t working. After I had the pantie on for a while I thought I could really do it because it started feeling really good having something in my ass, but I can’t do this.”
I looked down, and since my eyes were adjusted to the light in the bay, enjoyed the view of my cock partially buried in her ass while her pussy was gaped open, still dripping juice, her legs pushed back on either side of her tits and still wearing those red pumps. It was a stirring sight and my cock got even bigger.
She finally said, “Please take it out. I’m sorry but it still isn’t working.”
I reluctantly eased my cock out of her asshole, and she sighed.
“Can you finish in my pussy?” she asked plaintively.
I told her, “Let me clean my cock real quick and then finish me in your mouth.”
She smiled and said, “OK. I can do that.”
I dashed off to the men’s room and cleaned my cock and returned. She had spun around, taken off her blouse and rolled it up and placed it under her neck. When I walked up, she laid her head over the edge of the stage and opened her mouth. I slid my cock into her mouth and after a couple of strokes, pushed all the way down into her throat.
She pushed me back for a second and then pulled me in again. I face fucked her and reached down and fingered her clit. She started a muffled moan and I finally felt my orgasm building. I picked up the rhythm of my stroke until I was about ready to cum. I mauled her clit a bit harder and finally got her into another orgasm. This finally set me off and I splashed a load deep into her throat.
She gagged for a second, only to bury me balls deep in her throat again. I hadn’t noticed but she had a bit of a masochistic streak, but also seemed to have a dominant side as well. She sucked and slobbered until I finally withdrew from her mouth.
She slid back up on the stage and as she sat up, grabbed her head and said, “Whoa. I’m a little dizzy.”
I told her it was from hanging her head down like she did, and it would pass in a second. I helped her stand up on the floor, and leaned her against the stage. I picked up her blouse and put it on her, and buttoned it over her tits. I pulled her skirt back into place, and kissed her.
“You’re sweet,” she murmured as I led her back toward the office.
“What are you going to do with the dildo panty?” I asked.
She looked at me for a minute, and said, “Will you help me put it back on?”
Never one to run down a lady in need, I told her, “Let’s do it.”
I led her into the ladies room where I had stashed it and asked her if she still had the lube.
“It’s in my purse.” I watched as she dashed out the door, almost running into it before unlocking the latch. She returned from her car with a small bottle of flavored sex lube, and I greased up the probes for her.
She slipped both feet into the leg holes, and I pulled the center section up toward her crotch until the probes just reached her pussy and ass. She positioned them where they would go in, and then I pushed upward from under the center between the probes as she pulled the panty up and into position. She winced slightly as the anal probe slipped in, but quickly relaxed.
Once the panty was in place, she smoothed her skirt and said, “I better go.”
She headed for the door and I told her to come back again some time.
She smiled as she went out the door, and turned and said, “When is the next time you’re scheduled to close?”
I looked that the schedule but noticed that it was a day when Mandi wasn’t working, and told her it wouldn’t be until the next schedule came out.
“Maybe I can trade with someone,” I told her.
“Let me know,” she said, and started out the door.
She turned around for a second, though, pulled open her blouse, leaned over and shook her tits at me.
“A little something to remember me by,” she laughed and went to her car. I cleaned up, locked up and headed home.
Wilma and I got together a couple of more times in the next month, each time getting closer to actually getting into a good ass fuck with her, and she was really trying hard. She would wear the dildo panty when she could, and finally started getting to the point where she could handle the second size butt plug. She tried the largest one, which was the same diameter as my cock, but she still had trouble getting it all the way in.
During this time frame, Mandi had a death in her family, not a close member but someone that she really wanted to pay last respects to. She decided to go back home for a couple of days to attend the funeral and do some visiting, and made arrangements to fly out of the closest major city, a Midwestern hub. I took her to the airport, and saw her off.
The next day at work, I was closing up when I saw Wilma’s car pull in. She stayed in the car since there were still some people on the simulators, and I walked out to her car.
She smiled at me and said, “It’s a shame there’s people here. I need your help getting undressed.”
The leer on her face told me everything, as she reached down and pulled her skirt up. I got a glimpse of the dildo panty and she smoothed the skirt back down.
“I’m getting used to this thing, “she said. “Can you come over to my house one day this week? Chuck is leaving for a 5-day run in the morning.”
This was a pleasant surprise, since Mandi was away as well.
“Mandi is back home for a few days. Why don’t you come over to my place?” I asked.
“I’d love to but I need to stay close to home in case I need to go get my kids at school. Besides, I’ll pick up some beer for you.”
I laughed and thanked her, but told her, “Stick around for a minute and let me look at the schedule.”
I left her and went back in the office. I looked at the schedule and noticed that we had a down day in a couple of days, so I wouldn’t have to work at all.
I went back out and told her about the down day, and she said “Great. Why don’t you come over about 1:00. We’ll have plenty of time to play. And my kids have a late event at school that day anyway.”
I replied, “Sounds good. See you at 1:00. And wear those red pumps.”
She laughed as she started the engine, and smiled at me.
“Maybe,” she laughed, and pulled away.
As I pulled up the street to Wilma’s house, I noticed Ann’s car was gone. Ann was her best friend down the street, and never walked to Wilma’s house, even though it was only three houses away. She always drove her car. She was strange, too. A local, she had been married about 12 years, and had a couple of kids, one the same age as Wilma’s daughter.
Ann looked like a local too, kinda slim, not much for tits, plain looking, and appeared to have clawed her way out of a hard-scrabble family to a lower middle class existence. She had given me a sort of disgusted but amused look when we met, and I had little to say to her. Anyway, I drove on up to Wilma’s house, parked and went to the door. Before I could knock, the door opened.
When I stepped in, Wilma was behind the door, wearing a sheer gown and her red pumps. She had fixed her hair and make-up, and her reddish hair looked really good, better than I had ever seen it. Her make-up was flawless too. She had a drink in her hand, and asked me if I wanted a beer. I accepted and watched her walk into the kitchen.
Her ass was visible through the gown, and I started getting hard in my shorts as I watched that ass bouncing away.
When she returned, she noticed the obvious bulge and said, “Aren’t you just ready to go!”
I took a draw from the beer and laughed, telling her, “Just watching your ass going away started this.”
It was her turn to laugh.
“I’m glad I still have that effect on someone,” she quipped.
I moved over to her and grabbed her around the waist with one hand. I moved in and kissed her. I got a long kiss and some tongue in return, and she pressed up against me, wrapping one leg around my leg and moving it up and down in a slow stroke. I broke off the kiss and she looked at me.
“Wow. Nice way to start.”
She gently pulled away from me and said, “Come on in.”
I followed her through the house and straight into the bedroom.
As I entered I said, “Would you be in a bit of a hurry yourself?”
She laughed out loud, then looking back at me said, “You think I could actually get horny with you?”
I just smiled and said, “I hope so.”
She came up to me and said, “I can.”
She set her drink down and pulled me close, rubbing her tits into my chest. I could feel the hard nipples through my t-shirt. She ground her crotch into me and pulled me down for another kiss. As we kissed, she took my beer, and set it down and continued kissing me. She sucked my tongue into her mouth and pushed it back out with hers.
As I got harder, she rubbed against me even more. She broke away long enough to snatch my t-shirt over my head, and quickly leaned down and tongued one of my nipples. This was a surprise, albeit pleasant. She rubbed my cock though my shorts, and in a minute or so I was fully hard. She left my nipples, kissed down my stomach, dropping to the floor on her knees and pulled my shorts down.
As my cock sprang free, she engulfed it in her mouth. She took most of it down her throat and after about 4-5 slow strokes, stopped, stood up and pushed me toward her bed.
“Lay down on your back,” she commanded.
I lay back on the bed, and she looked at me with a serious but horny look, and slipped out of her gown. She climbed on the bed, straddling my head with her crotch and quickly dropped her pussy onto my face. She leaned down in a 69 position and swallowed my cock whole, gagging a bit at first, then started working a long steady stroke. I mauled her clit with my tongue, and my efforts were rewarded with a moan.
I began working her clit in earnest, stroking it with my tongue, and concentrated on not coming in her mouth from the nice suck she was putting on me. I noticed a sheen around her asshole and realized that she had already been doing something with her asshole because it was still lubricated. I pushed a finger into her pussy and one into her asshole, and was rewarded with another deep stroke down her throat.
I worked her clit until I thought she was about to orgasm, when she suddenly spit out my cock, and jumped off me. Before I could say anything, she straddled me, and slid her pussy down on top my cock. She slowly slid her pussy up and down the length of it without penetrating. She leaned over, placing her hands on my shoulders, and began to slowly stroke her pussy up to the head of my cock and then slide all the way down to where she would take just a bit of the head into her pussy.
This went on for a while, with her taking a little more cock into her pussy at a time, until finally, to my relief, she slid the entire length into her. Her pussy was hot and juicy, and she dribbled pussy juice over my stomach. She stayed fully impaled for a moment, eyes closed tightly, and then slid my cock out and stroked her pussy and clit on it again.
She did this for several minutes, and I kept still and watched with fascination. Her nipples were rock hard, and I reached up to play with them only to have her push my hands back to my sides. She kept riding for a while until after a few more minutes, when she had slid all the way out, I felt my cock began to penetrate again, only this time I was different than her pussy. There was more resistance. She pushed back, and with a slow intake of breath, pushed back until I felt the head of my cock entered her asshole.
She stayed still for a moment, then slipped out and rode up on top my cock again, grinding her clit into the head. She had yet to open her eyes. She slid back down and again backed onto my cock, this time slowly taking a couple of inches into her tight butt hole. She leaned up a bit and slid back down, this time keeping my cock in her ass. She pushed back some more, taking over half into her ass.
She pulled back out to the ring of my cock head and again pushed back, her face drawn in pain, stopping for a second, and then with another sharp intake of breath, pushed back until I was completely inside her ass. She leaned back, took another deep breath, and opened her eyes.
“Give me my drink,” she said.
I reached over, grabbed her drink and handed it up. She drank it down slowly, sighing contentedly, and handed the glass back to me.
She seemed to have gotten over the pain, because after I sat her glass down, she smiled at me and said, “I have your cock all the way up my ass.”
“I can feel it,” I replied, “and it feels great.”
She smiled again and said, “I want to do this now. I want to feel your cum in my ass. I want to know what it feels like to have a hard cock slam in and out of my little butt hole. I need this.”
I didn’t know what to say, but it didn’t take but a second before she leaned over and began to slowly slid my cock out of her ass, only to stop and slowly slide it back in, She rode my cock with her ass slowly, carefully, letting her clit press into my stomach occasionally. Then she stopped, and without saying anything, threw one leg over to my side, and carefully pivoted around so she had her back to me, never removing my cock from her ass.
She leaned down and set her hands on my knees and began to stroke slowly up and down. I had a great view of my cock almost pulling out of her pucker only to be completely engulfed again.
She finally began to talk. “Damn, I never thought this would happen but it doesn’t hurt anymore. Damn, this feels good. Fuck my ass you bastard. I want your cum in my ass. Put it deep in me.”
I got even harder as this went on, and found myself getting close to an orgasm.
That’s when she stopped, looked over her shoulder and said, “Please don’t cum yet. I want you to do it now.”
She slid my cock out of her ass, leaned over on the bed and stuck her ass high in the air. I sat up and got on my knees behind her. Her asshole had closed back up but as I probed into her again, she opened up and I slid back in with no trouble. Her ass was hot and tight, and she moaned when I had finally pushed the entire length into her.
“Damn it goes a lot deeper like this, “she complained.
“Do you want me to stop?” I asked.
“No, please don’t. I want to do this.”
I eased back into to the hilt, eliciting another moan, and realized I was pushing past her inner sphincter, deep into her gut.
“God I can feel it in my throat,” she moaned.
She had her head pressed down on the bed and I began to slowly stroke in her ass, pulling a couple of inches out and slowly pushing back in.
“Why don’t you reach under and rub your clit,” I suggested.
She complied immediately, and began to rub her clit in earnest. I kept a slow stroke going in her ass until after a few more strokes, she hit her orgasm, and the spasms gripped my cock like a little hand. She rocked through her orgasm, and pulled her hand out. She reached back with one hand and pulled on an ass cheek.
“Come on, fucker, cum in my ass.”
I figured it was time, and I began to long stroke in and out of her ass, picking up the speed until I was finally getting to slam fuck that fine ass.
She started wailing in a high pitch, and I slowed down, only to have her scream, “Fuck my ass, goddamit.”
I retuned to the merciless pounding and she started wailing and moaning, and started saying, “Fuck my ass,” over and over.
I told her to reach back with both hands and hold her ass open for me, and she complied quickly. I grabbed her waist and slam fucked that asshole like there was no tomorrow, finally feeling a good cum building inside me. I told her to hold on to her ass so I could fill it full of cum. As she grabbed those luscious butt cheeks and pulled them wide open for me, she wailed even louder as she suddenly burst into an orgasm I didn’t expect.
This put me over the top, and I blasted shot after shot of cum, loading what felt like a pint into her ass. I had three or four small spasms, then finally I stopped stroking and pressed deep into her, not moving. She was breathing heavily and shuddered a couple of times. I let my cock continue to soften, and finally slipped from her ass.
She stayed on her knees for another minute, asshole gaped wide open, her pussy dripping juice onto the bed. She had a hand tucked under her chin, and finally eased onto her side. That’s when the first bit of brown stained cum began to leak from her ass. I rolled her onto her stomach, let her rest for a minute, finished my beer and got up to get another one. I asked her if she wanted another drink, and she mumbled something in the affirmative.
I fixed her drink, and returned with it and my beer, enjoying the sight of her naked body wearing nothing but her red pumps. Her ass cheeks were still red from where she had gripped them so tightly. When I sat down, I noticed that her asshole was still slightly open. I told her she might want to head for the bathroom first, and she rolled over on her side, looked at me, took her drink and sipped it. Then silently, she eased off the bed, and started to step away.
She suddenly put one hand behind her, and dashed for the bathroom. I chuckled and followed her, looking in to see her sitting on the toilet with my cum slowly dripping from her butt. She looked at me vehemently, and motioned me out. I took my beer and went back to the bedroom.
I had just sat down on the end of the bed when I noticed the closet door was partially open. She normally left this door shut. It was a large walk-in closet that doubled as her dressing area, and she normally didn’t let anyone see her closet. But before I could wonder about this I heard a strange noise, a kind of gasp, and realized it had come from the closet.
My first thought was she had let Chuck watch us fuck for some reason, and worried that he would be trouble. I figured I would confront him, though, and slipped off the bed and over to the wall away from the door handle. I quietly reached over and pulled the door open with a quick tug, to be met with a muffled shriek. When I looked into the closet, Ann, the neighbor, was sitting on Wilma’s vanity stool with a video camera. She was wearing a large t-shirt, and her eyes were wide open with fright.
Before I could say anything, Wilma came out of the bathroom said, “What are you doing?”
I looked at her, getting angrier all the time, and shot back, “What the hell are you doing?”
I looked back at Ann, who had fixed her gaze on my cock. When she realized that I was looking at her, she looked away, quickly turning red from embarrassment.
Wilma started by saying, “You said you like to watch. I wanted to watch too, especially since I was confident this was the first time I could take a cock all the way in my ass. In case I didn’t get to do this again for a while, I could watch it when I wanted to, and maybe let Ann watch it too. She needs help.”
I looked back at Ann, and she squirmed nervously, avoiding looking at me.
“OK, but you could have warned me first,” I spit out.
Wilma smiled at me, and walked over to the closet.
“Come on out, Ann,” she told her.
Wilma took the video camera from her and she stepped out of the closet. The two of us were still naked, and Ann seemed really uncomfortable. I went to put on my shorts but Wilma stopped me.
“Ann needs a lesson or two, and I want you to teach her.”
This was possibly an interesting development except for the fact that I found Ann anything but attractive. I’m not sure what she would do to get me hard but I doubted she would be able to accomplish it.
“Let me tell you some things about her,” Wilma said.
Ann looked at her with pleading eyes and said, “No. Please don’t tell him anything.”
I was curious though, and gulped down the rest of my beer.
Wilma said, “Let’s get a refill, fix Ann a drink and we can tell you the whole story. Ann, you stay right her on this bed until we return.”
Ann looked like a little puppy dog but sat down and stayed right there. We went into the kitchen, filled the drinks and returned to the bedroom. I sipped my beer and watched as Wilma walked over to Ann and reached down, took the t-shirt by the bottom and quickly pulled it up and over Ann’s head, throwing the shirt into the closet and shutting the door. Ann’s hand went instinctively over her beasts.
Wilma walked back to her, and handed her a drink, and pushed the other hand down on the bed. She looked at Ann with a mean look but she left her hand on the bed. That was when I noticed that Ann was wearing the dildo panty! That must have been why she made that noise. After watching and taping Wilma and I she had an orgasm in those panties.
Wilma began the story of Ann, telling me how Ann was a virgin when a drunk uncle had raped her when she was fourteen, and then she was told that no one would ever marry her since she was no longer “cherry.” This created a severe problem for Ann’s psyche.
Fortunately, she met a guy from a town several miles away who was there working a construction contract on the military post. They hit it off, and after a casual courtship of several dates, they got engaged. She was 16 at the time and wanted away from her home and redneck family. They got married, and she had sex with a man she loved for the first time. He was about as knowledgeable and naive as she was, and they struggled to figure it out for the first few times. Someone had told him that the woman was supposed to lay on her back and he would get on top and put his cock inside her, and that was all you did. She didn’t know any better, having only the most rudimentary sex education from a Sunday School teacher who had helped her after she first began to menstruate.
Ann and her husband had three kids, and that was the result of half the times they had sex. She would lay on her back, her husband would poke around until she was moist enough for penetration, slide it in and stoke away until he had an orgasm. Until Wilma had introduced her to a vibrator, she didn’t know what an orgasm was. And even worse, when Wilma, as many women do, asked Ann about how big her husband’s cock was, she really didn’t know as they never saw each other naked, but she said it felt about 4″ long or so.
When she used Wilma’s 7″ vibrator, she barely got half in before she was so full she stopped, saying that it was more than her husband. All this time, Ann sipped her drink and squirmed around on the bed. She kept an embarrassed look until finally Wilma told her to stop it. Wilma also told me that she had talked Ann into wearing the dildo panty while she taped us having sex so she could get loosened up in case she decided she wanted to join the fun. Ann got embarrassed again, and when Wilma gave her a dirty look she meekly looked away. Ann looked at least Wilma’s age but it turned out she was only 24, a few years younger than I was.
All this was interesting, especially when Wilma told me that to make getting the dildo panty on easier, she made Ann shave her pussy bald and gave her some of the flavored lubrication. She then told Ann to lie back on the bed.
Ann complied, and Wilma told me, “Take it off her.”
I grabbed another quick sip of beer and pushed Ann’s legs back. I started peeling the waistband down and slowly pulled until the probes were in sight, and stopped. Wilma was right, she was shaved completely bare, and it was a fresh shave at that. I pushed down on the probes and they began to slip from Ann’s pussy and ass.
Before I realized it, I noticed that Wilma had the video camera out and was taping me removing the panties. Ann put her hand over her face and turned away, but Wilma kept taping. I slowly pulled the probes free, making Ann groan under her breath. After clearing them from her legs and feet, I showed them to the camera, inside out so the probes stuck out.
That’s when Wilma told Ann, “Get on your knees with your legs spread.”
Ann was already looking like she might throw up any second, but now looked absolutely horrified. She opened her mouth to protest.
Wilma lowered the camera and asked her, “Do you want me to send this tape to your Mom?”
She almost cried, but turned around and raised her ass in the air. Her pussy and ass were slightly open from just having the probes removed, and the view of her shaved crotch from, quite obviously now, front to back was actually enticing. Wilma zoomed in for a close view, and pulled her shot back out.
She told Ann to sit back up and returned her drink to her. Ann finished the drink, and Wilma handed it to me and asked me to get her a refill. Ann tried to pass it off, but Wilma insisted again and I got a refill. Ann sipped a bit of it as Wilma told me what she needed from me.
“Do you think you can make Ann have an orgasm or two, like you do to me?”
I told her that it was up to Ann, but Ann was trying to sink into the bed. I doubted she would be cooperative anyway, and force was not my thing unless it was a mutual S&M game. But Wilma leaned over and said something into Ann’s ear, then something else, and Ann partially smiled and blushed again.
Finally Wilma smiled at me and said, “Ann would really like you to make her have an orgasm.”
Ann looked at me shyly and smiled, and then looked at my cock.
I figured, “What the hell.”
Wilma grabbed the camera again, and said, “OK, I am the director, and you two are my actors, and I want some action. So let’s get to it.”
As soon as the tape was rolling again she had me move over to the bed and told Ann to suck my cock until it was good and hard. Ann complied, slowly taking the head into her mouth. I thought she would throw up for a second, but she glued her eyes shut and valiantly gave it a try. As she sucked, she scraped her teeth on my cock, and I jumped in pain.
Ann looked scared and asked in a meek voice, “Did I do something bad?”
What hard I had gotten had been immediately lost, so Wilma stopped the tape and gave Ann a short tutorial on sucking cock. Ann nodded in understanding, and gave me a second try. She was timid at first, not wanting to hurt me again, but finally began to show a little enthusiasm. I looked down at that clean shaved pussy, and imaged what flavor it was from the dildo panty, and began to get really hard again.
I looked at Wilma, nice tits, still in those red pumps, great tits for her age, taping the scene. This got me really hard again, and finally Wilma broke off the shot and told me to get on the bed. I laid back and Wilma had Ann climb on top me like she had.
Wilma knelt at the bottom of the bed behind Ann and began taping again. She told Ann to reach down and grab my cock and slowly put it in her pussy. Ann responded, slowly easing my cock in.
When she had about half of it, she said quietly, “It’s so big.”
Wilma chuckled and told Ann, “That’s the point, sweetie. Push a real cock up in you this time.”
Ann began to slide back down my cock, wincing slightly from the pain of having a cock pushing deep inside her. By the time she got half of my cock into her pussy I was in virgin territory. I reached up and began to play with what little tits she had, slowly manipulating her nipples. They responded by getting hard, and Ann looked down at her chest and blushed again.
I pulled her to me and sucked one of those little tits into my mouth, swirling my tongue around the nipple. After a second, Ann let out an audible sigh. Wilma jumped up and ran around the bed to get some of this action. I pulled away and sucked the other tit into my mouth, applying the same action to the nipple. It responded by getting rock hard and Ann let out another sigh, this time easing down until she had my cock buried in her pussy.
Wilma told Ann to start riding up and down on my cock, and she responded, awkwardly at first, but finally finding a good position to work from. While obviously a rookie, she was starting to get some real enthusiasm into the deal, and from the feel of her pussy, I didn’t think it would be long before Ann had an orgasm.
Wilma kept the tape rolling and sure enough, Ann had a quiet, shuddering orgasm, and almost collapsed on my chest, panting with labored breath. Wilma stopped the tape, and had Ann get into a 69 position and told her to suck my cock while she taped. I licked Ann’s pussy, noticing the clean, slightly strawberry flavor.
I concentrated on her clit, and Ann lost all effort at trying to suck my cock, content to get eaten while she held about half my cock in her mouth. Wilma apparently roused her by pushing on the back of Ann’s head, and she almost gagged, but returned to stroking about half my cock in her mouth. Within minutes, she had another orgasm, this one more vocal and it rattled my cock with the vibration. That’s when Wilma stopped the camera again, and whispered in Ann’s ear.
Ann got off me and Wilma motioned me to get behind her. Wilma pushed Ann’s head down onto the bed and I got on my knees and aimed my cock for her pussy. Wilma motioned me to slowly push into her pussy, and I worked it in an inch at a time until I was in to the hilt. Then I slowly withdrew.
Wilma motioned me to get rolling, and I began to pound into Ann’s tight pussy with a passion. Ann began to moan and groan. Before I knew what was up, Ann was rolling through another orgasm, this one more violent than the last. My guess was she had been building up for this for a lifetime, and it was starting to come out now.
I had a death grip on her slender hips and pounded her pussy like a jack hammer. I looked down and she had her head turned to the side, eyes shut and was drooling on the bed. Wilma got down on the bed and shot a close-up of her face in the middle of her orgasm. After grinning at me, she motioned me to slow back down.
I let up on the pounding and Ann gradually began to wiggle her ass around. Wilma handed me the bottle of flavored lube, and had me lubricate Ann’s ass. Ann was startled at first when I poured the liquid onto her asshole, but after I began to work a finger in she relaxed and wiggled into it. I added a second finger and could feel my cock through the wall of her ass.
Wilma once again bent over and whispered something in Ann’s ear. Ann looked at Wilma and tried to shake her head no, but Wilma leaned over and said something else to her. She looked a bit scared at first, but pushed her face back into the comforter.
After watching me fingering Ann’s asshole for a while, Wilma returned to taping and came over to where she could get a good view, and quietly told me to put my cock in Ann’s ass. As I pulled out, Ann seemed to tense up, and I rubbed and stroked her ass gently, telling her to relax and just let it flow, like she did with the dildo panty.
She moaned when I put my fingers back in her asshole, and then after stroking for a minute, eased the head of my cock even with her little pucker. Actually, she had a smooth little hole, partially open from my fingering, and I pressed my cock head against it. Wilma was concentrating on taping and had a close-up of the action. I slowly pushed in until I popped free of her sphincter, and Ann let out a long, low moan.
I held still for a minute only to have Ann begin to wiggle her ass back toward me. I pressed in some more, and her asshole felt like a tight hand gripping my cock. As I went deeper, Ann began to moan louder and rocked her ass back and forth. I wasn’t sure if she wanted more or less. But I pressed on until I squeezed past her inner sphincter and pressed my stomach against her skinny butt.
Wilma stopped taping for a second and asked me if I could lift one leg up and on my foot like they did in porno movies so she could tape from underneath. I obliged, and although I had seen this done in movies before I didn’t realize until then how hard it was to really do any deep stroking with any power like that. But Wilma got the camera down on the bed, and moved the view finder around so she could get all the action from down under, and told me to start stroking into Ann’s ass.
Ann groaned again when I withdrew about half my cock and pushed back in, but she hadn’t pulled away, so I slid about half my cock out again and back in. Ann was suddenly quiet and not moving. I looked down, and noticed that she had her eyes shut and didn’t appear to be conscious at first. But she moaned again, and began pushing her ass back toward me.
I figured she was alright and began to pull more cock out before sliding back in. I slowly increased the rhythm and got some rhythmic groans in return.
As I finally started pulling my cock almost from her asshole before sliding back to maximum depth, Ann started a strange “Uhnn, uhnn, uhnn…” with each stroke.
It gradually got louder as I pounded harder. I got a grip on her waist so she couldn’t move and went at her asshole in a frenzy. Since I had already cum once this one was going to take some stimulation. I enjoyed the view of my cock pounding into her hairless ass, and from this view she looked very young indeed.
Wilma slid the camera out from under us, and I dropped back onto both knees, and hammered Ann’s ass. I wasn’t sure I could cum, though, until I felt Wilma fondling my balls from behind me. I could feel her nipples rubbing my back as I slammed in and out of Ann’s asshole, and Ann was getting louder all the time.