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She dated, mostly to find a father for me I think. I don’t remember most of them, but one of the last ones I recall, she came home from a date and I was still awake in my room. I heard her tell the babysitter goodnight and then there were some voices, hers and a man’s. The talking died down and then it was silent. I laid there wondering why she hadn’t come in to check on me, so I got out of bed and walked into the living room where I saw her kneeling in front of a man who was sitting on the couch. I only witnessed it for a second before I spoke up, but her face was looking down into his lap and her head was moving back and forth.

“mom?” I said, standing at the edge of the room holding a stuffed animal. It startled them both way more than it should have, and she jumped to her feet and the man squirmed around covering himself.

“sweetie what are you doing up!?” she said as she immediately led me back to my room. She got me tucked back in bed and told me to go to sleep, then went back out to her date. I don’t think I ever saw him again, and from that point on she hardly even dated anymore, until she finally stopped and it was just the two of us.

She’s a wonderful mother. We went on trips and did fun thing, I was her whole world, and she often let me know it. Especially if the topic of her being single or me having a father ever came up.. She’d say things like, “we don’t need anyone else do we??” and “you’re the only man in my life right??” of course I always agreed and it made me feel special. But honestly I didn’t ever feel deprived or miss having a father, she filled both roles perfectly. She got me involved in all sorts of activities like sports and scouting, and she was always in attendance. This led to some issues over the years. When I was younger I had to defend her when kids would say she’s fat, and as I got older I got into fights when boys made comments about her big tits. Until now we would still routinely fall asleep in the same bed and go out to the movies together, things like that.. This all changed.

I was tall and athletic and got onto the basketball team quickly, by my 2nd year I was the star, not only of the team, but of the state. This made me popular and my schedule filled up fast! In addition to school and basketball I was in student government, multiple clubs and in advanced classes, all with the purpose of getting a free ride to college.. We lived one town over from an ELITE basketball school and my dream was to go there.. But on top of this came parties and girls.

My mom was proud of me and supported all my endeavors whole heartedly but the reality of having a teenaged son came crashing down on her one Friday when I went to a party rather than stay home and watch a movie with her. I had already been “growing up too fast” as she liked to put it, and virtually every weekday was filled with school and extracurriculars, but the weekends had remained the time for her to spend with her “special guy”… until those too were taken away. Social functions began to dominate my weekends and almost instantly I was getting dates.

These were innocent of course.. I was painfully awkward and had no game, but regardless, I had a bright future so girls put in the effort. Which led to me getting my first blow job, it was quick, but like nothing I’d ever experienced, I was still a virgin, and had never even masturbated (to be honest, I’ve still never masturbated once in my life). Now I didn’t have a car, my mother and I weren’t wealthy, so this particular girl had to pick me up and drive on our dates. Afterwards she would bring me home and, not always, but usually give me a bj in the front seat of her car, parked in the driveway. My only complaint (not that I really had any basis for comparison) was that when I came, she sat up and just let me jizz all over myself. It mostly got all over my boxers, but some would always get on my pants and I’d have to try and wipe it off with some napkin or something. It was just messier than I’d have liked, and made the actual orgasm troublesome and less rewarding than it should’ve been. I also had the embarrassment and discomfort of going into the house and trying to conceal any mess from my mother as I shot up to my room to clean myself off and change. But getting my dick sucked semi regularly was like hitting the lottery and she became my girlfriend.

All this went on for a few weeks, and unbeknownst to me, it was negatively affecting my mom. She would ask if I had plans for the weekend, and when I told her I did, she would make comments about eating dinner by herself or something similar. I always took it as a joke, but her feelings of loneliness and abandonment were brewing into resentment. Initially she didn’t mind the idea of me dating, seeing a future with large family dinners and grandchildren, but the reality was setting in that in order to get to that point, I was going to be out of the house rather than bringing my girlfriend over for dinner like mom always suggested. Of course this was because we wanted privacy, and it left my mother alone and annoyed.

Now usually she was either asleep, watching TV or reading when I got back at night, which was always in time for curfew. And this night was no different, except that she happened to notice the car’s headlights as we pulled into the driveway. She put down her book to await my arrival through the front door, but I never walked in. Curious, she went over and looked out the window, it took her several seconds to process what she was seeing… me sitting in the passenger seat with my eyes closed, seemingly alone in the car. Until she noticed the movement in my lap, the back of a head moving up and down, disappearing from sight behind the dashboard and reappearing slightly. ‘So this was it?!’ she thought angrily to herself, ‘this is why he wants to go out with her all the time! For a blow job!?’. Now the idea that I was sexually active was not a huge issue. Sure maybe she didn’t realize it would be so soon, but she knew it would happen. And she wasn’t exactly a prude, so there was no anger about her son getting a blow job per se, but what made her angry was that I was clearly abandoning her, my only family, for something as trivial as a bj from some insignificant high school bimbo!

So naturally, as angry parents usually do, she came bursting out of the house without thinking it through. She yelled, my girlfriend was mortified, covering her face, I struggled to stuff my erection into my pants as my mother threw open the car door and practically pulled me out. The car squealed as it shot down the road while my mother scolded and shoved me into the house where I fled up to my room. I was grounded, but there was no discussion about what had happened.

That week my girlfriend and I effectively broke up. I fulfilled any after school obligations each day, but afterwards I went straight home and to my room. It wasn’t until the following Friday that my mother finally spoke to me.

“how is she?” my mom asked flatly, while looking at her dinner plate, referring to my ex.

“we broke up.” I responded. I saw her eyes move a bit, this was a bit of a surprise to her.

“well, I know you’re still grounded, but how about this weekend you and I do something? Like a movie?” she just brushed past the breakup news, secretly happy to hear it.

“no thanks.” I said. I stood up, put my plate away and went up to my room.

I was still grounded until the next weekend, and we still barely spoke, or rather, I barely spoke to her. She had gotten what she wanted, for me to stay home, only I wanted nothing to do with her. I’d made plans with some friends for the following Friday night, I was going to be free and just wanted away from the house. I got out of the shower and had a towel around my waist while I picked out clothes in my room when she walked in.

“what are you doing?” she asked casually.

“getting dressed to go out.” I answered, still very cold towards her.

“why, to go get a blow job?!” she snapped, instantly regretting it.

“what?!?!” I said, turning to her, insulted and in shock. I expected her to apologize, or at least walk out, but instead she doubled down on her rash statement.

“you haven’t spent any time with me in months, why?! Just so you could go get a bj from some little high school bitch who I guarantee doesn’t even do it that well!” she was just unloading on me now, probably not even hearing what she was saying to her own son. “I get it, guys love getting their dicks sucked, I know, I used to do it a lot, and I was good, but for Christ sake did you have to spend ALL your time with her!? You couldn’t have stayed home every other weekend or something?! God, if Id known that all you wanted was a blow job I’d have started giving them to you years ago! At the very least I’d have given you head if it meant you’d spend some time with me! Jesus!” she just stood there breathing hard. She’d practically yelled at me about how she would suck my dick, her own son, and now she was realizing it. I stared back, my eyes wide. Her face softened with fear and disbelief in what she’d said. She debated just walking out of the room, but knew that at some point she’d have to address this.. So instead she threw a Hail-Mary.. “I’ll give you a blow job right now if you stay home tonight!” she yelled it at me, but straightened herself up trying to look calm and collected, but really she was terrified. But to her own surprise she wasn’t scared of the thought of having to go through with it, but what might happen if I declined.. Really she’d already embarrassed herself and possibly damaged our relationship, offering to blow me now really wouldn’t do any more damage than had already been done, and on the off chance that I said yes, it would potentially negate all the possible negatives and we’d be all better… she looked at me for what she thought was an eternity, never in a million years did she ever think that she’d be standing here hoping to give her son head! But what’s even crazier is that my reply was actually nearly instantaneous.

“OK.. Fine.” I said. I didn’t yell it out or anything, but I didn’t have to think about it at all. My answer surprised her, but she felt relief and nearly smiled. I just stood there, unsure of what to do, and she realized that.

“um, go ahead and sit down.” She said as she started playing with her hands nervously.

I sat down on the edge of my bed, conveniently still in just a towel. There was a noticeable tent as my cock swelled with anticipation of an incoming mouth. But there was more to it, I was excited that it was a new mouth, and I was strangely excited that it was my mother’s. She seemed hesitant at first like she was trying to remember the steps to giving a guy a blow job. Her hair was already in a pony tail but she fixed it to get all the hair out of her face. She dropped to her knees in front of me, never looking me in the face, I figured she was embarrassed or ashamed of what she was going to do, but all she was thinking to herself was ‘alright, you need to make this the best one you’ve ever done!’ but in reality, my youth and inexperience meant that to me, anything would be viewed as a great bj! She opened the towel with a sort of professionalism, using two hands and parting it neatly. I thought she might stall, maybe to see if I backed out, but she didn’t, she just started stroking it softly. Her other hand began fondling my balls, a sensation I hadn’t yet experienced. She looked straight down my cock took a small breath and went down. She swallowed my whole prick and held it there, still kneading my balls. I’d say I’m average in length, but pretty thick and veiney when hard, and this was the hardest I’ve ever been. She raised her head and removed me from her mouth, my cock dripping wet, and she began stroking my slickened tool again. She lowered her head, and I leaned back further resting on my elbows. She started kissing and licking my nuts, I gasped. Her hand was moving them around, allowing her to slide her tongue across every inch of my smooth sac, all the while her other hand was rapidly working my spit covered shaft. It had barely been a minute but I felt my orgasm begin to rise.

“I’m gonna cum.” I barely muttered, embarrassed by the speed at which I was going to finish. My mouth was hanging open and my eyes were droopy, giving me a drugged look.. And feeling.

I felt my incoming load surging through me, I knew it was going to spray across my lap, but to my surprise my mother’s mouth dove down onto my dick, engulfing me just in time to catch the first shot of jizz. It was the biggest orgasm I’d ever had, my body trembled and jerked involuntarily as I felt my balls pump what felt like gallons of cum up and out of me. But the most amazing thing was watching my mother take it all. One hand still held my sac as it rose and fell, while the other stroked the base of my erection, urging the semen onward. Her head moved up and down slowly, barely even noticeable, just enough to move her lips back and forth across the ridge of my swollen cock-head. I sprayed almost endlessly into her mouth, powerful shots that would make a lesser girl gag, but she gave no indication that it was even happening, swallowing it all with ease. And when I was finished, spent from the most draining 2 minutes of my life, she simply lifted her head and wiped the corners of her mouth and licked her lips as if she’d just had a taste of brownie mix straight from the bowl. She looked my crotch over for any messes, but there was nothing, just saliva. She used the sides of the towel to gently wipe the whole of my package, including my thighs. And then she stood up and fixed her clothes.

“alright, now I’m going to go make dinner!” she said happily, looking just like a mother talking to her son. She turned to walk out, “oh! And we have plenty of shows to catch up on tonight!”, and she left.

I did the best acting job of my life that night, trying not to be weird and pretending I wasn’t still in the afterglow of my mother’s blow job. She on the other hand was the happiest and most lively I’d ever seen her. She gave no indication of regret or anything, and laughed and talked the entire time. I kept catching myself looking at her body now, something I’d never done before.

It finally got late and was bed time, and I don’t know if she sensed my awkwardness or had noticed my glances, but as I got up off the sofa she looked up at me and spoke.

“listen, that first one went kinda quick didn’t it?” she said with a little smile. I immediately knew what she meant and got embarrassed. “why don’t I do it again?” she said while already reaching out and grabbing the waist of my sweat pants and pulling me towards her, “you’ll last longer this time.” She was sitting on the couch looking straight ahead at my crotch as if she was talking to my penis rather than me.

Of course I went with it, and stepped in front of her. She pulled down my sweats and boxers in one tug and let them sit at my knees. By the time she took me in her hand I was already fully erect and she simply leaned forward with her mouth open. She didn’t use her hands this time, they held my hips, and she pulled herself back and forth. She went very slowly. The room was mostly dark (with the TV off), the only noise was the rhythmic sound of wetness from her mouth, it was soothing more than erotic, like when you were a little kid and your mom played with your hair while you were falling asleep. My eyes were closed and I my hands were placed atop my head to keep them out of the way. She removed her hands and placed them on her legs, probably for better support, but this somehow increased my pleasure! Now the only thing touching my body was the inside of her mouth sliding against my shaft. I don’t know if there’s a scientific explanation for it, but this sensation was inexplicably better!



Already I had lasted longer than before and I was thrilled because I really didn’t want it to end. But of course it was completely out of my control.. And I began cumming. I was so enthralled in the experience that I didn’t even think to tell my mother that I was close, but really I didn’t even know myself, I simply started cumming.. Unlike the last time where it came out like shotgun blasts, this one was more like a hose that had been turned on slowly. At first there was a spurting and then it just seemed to pour out in an almost constant stream of semen, but calmly.. There would be little surges but really I was just faucet of cum running down my mother’s throat. And boy was she a champ! Her head bobs lessened, and turned into just sucking tenderly on the tip. Deep swallowing sounds resonated like someone gulping down water. When I was done she stopped, pulled my bottoms back up and tucked my cock back in as it just started to wilt. She stood up and said goodnight and walked out. Leaving me to stand there for several moments longer and savor the tingling feeling.

The remainder of my high-school career was void of any non school related relationships or socializing. Everyone eventually heard the story of me being caught getting head and being grounded, so I just used the story further as a combination of being grounded and needing to focus on getting into college. Eventually I stopped getting invited to parties, and girls stopped showing interest. I did everything I needed to do each day and rushed home. My mother’s mouth was servicing me multiple times a day, and that’s all I wanted.. Some bjs were on a sort of routine schedule, like after school or before bed… other times she just noticed that I wanted one. I never had the nerve to actually ask, so I’d just bring her attention to it, by rubbing my crotch while we watched TV or something.. She’d look down, see the bulge and take it from there.

After MONTHS of me getting my dick sucked daily, we were back to being like we were when I was a kid. Going to the movies together or out to eat on Mother-son dates (often getting head in the car). Mom was thrilled and I couldn’t really complain myself. One night we walked upstairs and into my room, where I immediately began to remove my pants for my bedtime bj.

“why don’t you sleep in my bed tonight like you used to?” she asked with a smile. Now I didn’t really have any objections, I figured I’d still get head, and if she liked the idea then it was fine with me, but before I could say yes she increased her offer to seal the deal.. “we can have sex..” she said coyly. My mind briefly went blank.

“ya ok.” I tried to sound calm.

“well I need to tidy up the bed, so you get undressed and Ill call for you when I’m ready.” I nodded and she left. Quickly I stripped, my dick springing up in front of me, and then I just waited. Now really this shouldn’t be that big of a deal, I mean with the skill and frequency that my mother has been blowing me it’s not like I needed to have sex too! I wasn’t really missing out on much, or desperate for sexual release.. but I was still a virgin, and the idea of putting my prick in a pussy was very thrilling. Plus.. I hadn’t seen a naked woman yet, so this too was going to be a first for me. “OK come in!” I heard her call from her room. I took a deep breath a walked in.

When I opened the door to her room the lights were dimmed, I don’t know if that was for her or me, but there on the bed was my mother, completely naked, on her hands and knees with her ass pointed at me. She was looking over her shoulder at me, smiled and then laid her head down on the bed, keeping her butt in the air. It wasn’t a small one, but it was HOT, like those big oiled up asses you see in a porn that has ‘phat’ in the title. I walked forward, her cheeks spread wide, exposing her snatch to me like an offering. She was at the edge of the bed with her feet hanging off. Standing directly behind her my dick lined up perfectly with its goal, precum oozed out. I placed a hand on each cheek and pressing forward I slid in effortlessly. I told myself that I was going to go slowly, and savor it, but that went right out the window and I was full-force-fucking my mother after the second stroke. It felt incredibly natural, the movement, the placement of my hands, the bouncing of her ass off of my thighs creating an intrinsic rhythm.

Almost immediately I felt the stirring in my loins, the cum rising up. I probably could’ve stopped and waited to make myself last longer, but my body had no intention of doing that… I sped up.. I grasped her tightly, pulling myself deeper into her, and blew my load, shuddering with each ejaculating spasm. I continued giving her tiny thrusts with each shot, little slaps of flesh accompanying my grunts, getting softer until I was done. Several minutes after I had stopped I still stood there, almost unable to move. My mother waited patiently, letting out long satisfied sighs. I doubt she climaxed, so she was more proud than satisfied. Proud of herself.. That her body, her ass, her cunt could still gratify a man. Proud that a young man (and young cock) could find her so desirable. Proud of herself for getting what she wanted and pleasing her son in the process… confident he was so pleased that she had no concerns about losing him again.

When finally I released her, I stepped back and slid out, still erect. She fell into the bed and laid on her back, gesturing for me to join her. I climbed in the bed, I was drained, tired and beginning to soften but even so, I leaned over and clasped one of her heavy breasts and brought it to my mouth. I devoured it like an animal.

“see..” she started, “we don’t need anyone else do we?” I mumbled in agreement, “that’s my boy.” She said quietly. She closed her eyes and began running her fingers through my hair as I suckled at her teats once more.

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My man Roger and I have had sexual adventures that many people would be envious of: some incredulous of even. Around once a month I love having a second man to pleasure me and before I pleasure him while my man watches, and often he will pleasure my man: oral sex only – no intercourse is the rule. In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock. “Some of your...

3 years ago
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Crude experiences of a femboy

Aelvir was born into a normal family with a young brother and one older brother. Growing up, he began to notice his body wasn't growing quite like the other males. He steadily began to recognize that his arms, legs, hips, and even overall body curvature wasn't at all similar to much of the males he sees, especially even at school. He even noticed that the others even gave him odd looks whenever he was present and/or nearby. It wasn't till highschool that he noticed it even more. First, the...

Bisexual
2 years ago
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THE PAPERBOY

"Nick, Donny's here again. Pay the boy, now," ShirleyCummings said. Nick Cummings, 27, was a tall, strongly ruggedbusinessman. His wife was going away for the weekend to visither mother.The newspaper boy, Donny, came up the walkway with a bundleof papers in his hand."Hi, Mr. Cummings!" The boy said cheerily. Nick leaned outof the door and stared dreamily at the young man. Donny woretight 501 Levi's and no shirt. Nick watched as the boy bent overto pick up a coin he'd dropped.Nick's...

3 years ago
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the paperboy

"PAUL, BRYAN'S HERE AGAIN. PAY THE BOY, NOW," SHIRLEY NASH SAID. PAULNASH, 27, WAS A TALL, STRONGLY RUGGED BUSINESSMAN. HIS WIFE WAS GOING AWAYFOR THE WEEKEND TO VISIT HER MOTHER. THE NEWSPAPER BOY, BRYAN, CAME UP THE WALKWAY WITH A BUNDLE OF PAPERS INHIS HAND. "HI, MR. NASH!" THE BOY SAID CHEERILY. PAUL LEANED OUT OF THE DOOR AND STARED DREAMILY AT THE YOUNG MAN. BRYANWORE TIGHT 501 LEVI'S AND NO SHIRT. PAUL WATCHED AS THE BOY BENT OVER TOPICK UP A COIN HE'D DROPPED. PAUL'S HEART...

3 years ago
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Tipping The Paperboy

Have you ever wanted to just do something really naughty? Well, I have. My name is Tammy, and I was divorced about 4 months ago. My ex was a scum bag that had no idea of how to treat or please a woman, if you know what I mean. Oh sure, we all want the bad boy when we are dating, but ultimately, they make terrible husbands and lovers. We lasted a whopping 9 months before I caught the bastard cheating on me with a filthy little skank from the grocery store. Well, I say good riddance; she can have...

3 years ago
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Mistress Jessica and her Asian boytoy

Disclaimer: This story is purely fictional. I always welcome comments and suggestions so please feel free to email me – kace.lee at gmail dot com. Thanks!Lee was bored. He was a 14 year-old student at Osborne High, a large high school that catered for thousands of students, and in his freshman year. Like most Asians, he was a top student in most of his subjects, but also like most Asians, he sometimes found it hard to score with western girls. Not that there were many good-looking ones in this...

3 years ago
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Ladyboys Moving to Thailand and my first Ladyboy

After living in the Netherlands for 33 years I was ready for a big change. I had been toying withthe idea of moving to another country to get away from the stress of it all for a while.I had girlfriends in the Netherlands. Wives.I had one nighters and 2 nighters. I wasn't doing bad for myself.But, there was something missing on the girl side. I love variety. I think I've been withevery kind of girl I COULD be with in the Netherlands. I started thinking about other countries.Other girls. Other...

2 years ago
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The Newlyweds Chapter 1 Boyshorts

The Newlyweds Chapter 1: Boy's Shorts Ji-min, my new wife, wanted to be called Jasmin now that she arrived in America. We have known each other for for about three years. She served on several mission trips in Africa. And I served in the Peace Corps. Thinking myself too small and not aggressive enough for regular military service I thought it was a good choice. And it was. When we met she was fifteen and I was eighteeen. Over the years she and I exchanged love letters, text...

2 years ago
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Anne Marie kitten Slutwife for cowboys

My latest bit of “whoring” was so hot, that he asked me to write a story about it. Bear with me, as this is my first attempt at literature. Trust me; I suck cock much better than I write. This past weekend my two girlfriends and I decided that a “girl’s weekend” was in order. We planned a road-trip to go see a professional bull rider’s rodeo in the next state over from ours. I wish I could say that I wasn’t thinking about finding myself some hot stud of a cowboy to fuck and suck, but...

2 years ago
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Anne Marie kitten Slutwife for cowboys

Introduction: A more recent detailed account of Anne Marie being the slutwife that she is. This time, she wrote the story. My husband and I have been together for 17 years now and believe me, I consider myself to be the luckiest wife in the world. You see, we have what you might call an arrangement. He allows me to fuck pretty much whoever I want, whenever I want. I, in turn have to promise to tell him all the sordid details of my slutty encounters. My latest bit of whoring was so hot, that...

4 years ago
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BSC03 Naked Surprises at BSCChapter 3 Philippa Boyd

A very solidly busted student called Philippa Boyd was assigned to show Katrina and Angela around the College. Philippa’s breasts were big and bounced along very happily with every step and movement of her body. They looked just great as they swung along and bumped into each other. Philippa always got admiring looks and smiles from the male students and staff as she passed. Angela and Katrina were delighted and entranced at her bubbly and buoyant attitude to everything. “You know,” she said,...

1 year ago
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My bestfriend makes a damn good Tomboy

As a child, Tyler was always a quiet, sheltered person and rarely went outside unless he was hanging out with friends. It was mostly because he would have had to deal with the bullies. One day the bullies started to pick on him, which he stood up for himself, only to be beaten up by them. They were beating him so bad to the point he was almost dead, but then a rough girl came in and fought them off. That was the day he met Emily, his new friend, and they got along pretty well, not many...

2 years ago
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The Wilmington Womans ClubChapter 7 Bernie Meets Eddie Boyle

It was a rainy Sunday; Bernie was just sitting around the off-campus apartment, watching The A-Team on NBC with George Peppard, and Chicago-born actor Mr. T. with two other girls, Frannie and Meg. Val was out on a date with Joe, and Bernie was more than a little jealous with the knowledge they were getting very serious about each other. Eventually, she got hungry, and got up to make herself and the others some spaghetti. As she stirred the sauce, she idly wondered if Eddie Boyle was going to...

3 years ago
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Lookingglass Ladyboy

I was taking a walk to stay--all right; I'll admit it--to get in shape, when I saw the "Going Out of Business" sign in the second-hand furniture store a block north of my condo. I wasn't in the market for anything, new or used, but I can't resist a bargain, and what was better for finding a bargain, I asked myself, than a store that was having a going- out-of-business sale? The store offered everything you could imagine, in every condition you could imagine--sofas, tables, chairs,...

2 years ago
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SoCalled Friend The Sissyboy

This story is a spin-off from my earlier story So-Called Friend. Using the first part of it I going to use a totally different story line. If you haven't read the first part of So-called Friend please do so. So-Called Friend: The Sissyboy By Jennifer Allison As my step-mom drove I tried to explain what had happened. All I got in return was. "I knew there was something about you Dean. Now I have the proof. Now shut up and stop whining. I don't want to hear another word...

3 years ago
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Space Cowboys

Author’s Note: From an idea by a friend on another site comes this story of role playing, X-men, funny stuff, and hamsters. It’s probably much funnier if you’ve ever played a role-playing game. I combined it with another story a role-player told me about a game where he had giant space hamsters, and his players got out of hand with them. This is the result. Disclaimer: I made up the game of Space Cowboys and the Fantastic Gaming House company. To my knowledge, there is no space game with Old...

3 years ago
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Frannies Femboy

Gay - cross dressing – femboy - feminization – blow jobs – anal sex – hand job – lingerieWhen I was finishing high school, I did a lot of different jobs to raise money. I mowed grass, worked part-time on a construction crew, and pumped gas, all to raise funds for college. I had been accepted to the college of my dreams on a partial wrestling scholarship, but my parents weren't going to be able to help with the other expenses. While I hoped to eventually turn the partial scholarship into a full...

3 years ago
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Femboy

I was about 16 when I started to take an interest in how I looked, until then I had been a school uniform or jeans and sweatshirt sort of boy. But as I approached my end of school exams, I noticed girls, not as sex objects like my friends did, but as clothes horses. They wore some amazing things away from school. And unlike my friends, I wanted to share in this joy of taking an interest in how I look. The first thing I did was to take better care of my hair, using my mother's shampoo,...

2 years ago
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The Paperboy

It was the Friday after Thanksgiving and my husband had to work and my son had gone for the weekend to stay with some friends, so I took the time to start putting up the Christmas decorations in our home. It was quite warm that day since we live in the South so all I had on was a white, button blouse and a pair of loose white gym shorts (the nylon silky kind) with no bra or panties. I was hanging garland around the fireplace when the front doorbell rang.I went to the window and peeked out to...

First Time
2 years ago
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Paperboy

I got out of bed at 6 AM to make my husband breakfast as usual. Quarter to seven he left for work and I had half an hour before I had to wake the children up for school. It was part of my daily routine. As usual I couldn't make any ruckus because that would wake the children up early and they wouldn't like that. Instead I just poured myself a cup of coffee as I do every morning. Still wearing the robe I went to get the morning paper exactly as usual. But this morning the paper wasn't...

3 years ago
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The Cuckoldress and the Boytoy

The following is a true story to the best of my and my wife's recollection. This is about my mature hotwife who went back to college and seduced her teenage lab partner. In most cuckold stories, the wives are gorgeous blondes with huge breasts and very cute or pretty faces. That is not the case here. Susan is the Consummate Plain Jane. She carries a few extra pounds from having c***dren. However, Susan is extremely sensual, passionate, and has the most sexually creative mind of anyone I've...

2 years ago
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Toyboy Boytoy

Toyboy Boytoy By Beverley Ann Miles I must have been heavily asleep. I finally awoke, as my mouth was forced open - and something plastic was being crammed in - and by that time, it was already too late to do anything about it! The little plastic circle had been inserted, covering my teeth and locking my mouth open. I couldn't figure out what it was. I lay on my side on the bed, already bound at knees and ankles, my wrists were secured behind my back. I was rolled face down...

3 years ago
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Green Beret Loves Asian Ladyboys

Demonde Scott woke up early most days.. He leaned over and kissed his girlfriend’s forehead. He threw on some basketball shorts, a tank top, and a pair of multicolored Nike Joyride Dual Run sneakers. The 5’11”; 200-pound man headed out of his small house on the compound where Westerners lived while working in the Kingdom. He stretched then launched into morning 2-mile run. The air felt thick on his skin. It was around 65% humidity at present, but the temp was good at a little over 80 °F.He...

1 year ago
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Playboy

Reddit Playboy, aka r/Playboy! I’m pretty sure you’ve all heard of the magazine Playboy. It’s one of the biggest names in the adult industry, and it has existed even before porn was a thing. This magazine was the best thing a teenager in the 90s could hope to get. Blockbuster and other video renting stores never let minors rent out XXX movies, so the only thing they could hope to get is a playboy magazine at the corner store from the shop owner who doesn’t give a shit about what these guys are...

Reddit NSFW List
1 year ago
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Prom night with Miss Boyd

I closed in on her woman parts. I could smell her. I had never smelt a woman before and the scent drove me wild. I started to kiss and lick at her entry point, fast and furiously. “Slowly at first Trent. Like a lovely flower that needs to open in the morning light. Slowly.” It was prom night. I was all excited because after tonight school would be over and I would never have to go back and see the bloody jock that always made my life a nightmare I had built up the courage to ask Silvia Jackson,...

First Time
1 year ago
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Bikers and Cowboys

I was having a quiet drink on a Saturday night in a favorite bar of mine. My table was at the rear of the main part of the bar. I say the main part because there is another part where you go through a special door to get to and not too many people know of it outside the regular patrons of the bar. In that special part is a low bar where a lot of business transactions are carried out. A guy I sort of knew came in with his wife and her sister. I knew that both women lived and slept with the guy,...

Bisexual
3 years ago
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Bellboy

When Mrs Estelle B. came into the lobby a month ago I wanted to pitch her myself. Stacked, classy, blonde with the pouty full lips I love. Course I didn't have a chance. No luggage except a purse, I caught the look from the manager, she paid with a credit card to a phoney gardening shop the Royale owned, so this wasn't her first time. Meant she had a buck lined up already, which she did. An hour after I showed her the room, a huge black buck picked up the key in the lobby. Couple hours after I...

2 years ago
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Bellboy

When Mrs Estelle B. came into the lobby a month ago I wanted to pitch her myself. Stacked, classy, blonde with the pouty full lips I love. Course I didn't have a chance. No luggage except a purse, I caught the look from the manager, she paid with a credit card to a phoney gardening shop the Royale owned, so this wasn't her first time. Meant she had a buck lined up already, which she did. An hour after I showed her the room, a huge black buck picked up the key in the lobby. Couple hours after I...

2 years ago
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  • 24
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Tomboy

"You're the new girl, huh?" The boy was bigger than me, and probably a year or two older. "What's your name?" "Ashley," I replied, sitting on my motorcycle and drinking a Mountain Dew. We were in the old suburbs. There wasn't much else around except the school, a couple churches maybe, and a Seven-Eleven, so that's where I'd gone. It sucks moving to a new city when you're sixteen, but it could be kind of fun too, depending on what you're looking for. "You look like a guy,"...

4 years ago
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Sexy Femina Ladyboy

OMG! I wore the most ADORABLE outfit to the arcade on Friday! Picture this: After bathing and powdering, I put on my little black silk shorty robe and a pair of poofy 2 inch heeled black slippers, and did my nails in a platinum shade. Then I did my hair and makeup. Doing the hair was easy as I simply chose a platinum blond bob. Then came my eyes and lips - a frosted pink lipstick. Then I put on my black string bikini. After some sexy posing in the full-length mirror, I put on my new outfit -...

3 years ago
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Used by a gorgeous ladyboy

(Yeah it's been a while but i'v been busy … doing the thing in real life with a new guy i met and there is not much need for xhamster at the moment :) . The story below is based on a true experience and i just changed a few details to spice it up a bit)This story is based on a true experience and happened a few years ago, on a great night out in Amsterdam. It was before i had sex with guys on a regular base and i entered a complete new and exciting world...During that period of my life i was...

4 years ago
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MY MAN AND I SHARE A LADYBOY

My man Roger and I have had sexual adventures that many people would be envious of: some incredulous of even. Around once a month I love having a second man to pleasure me and before I pleasure him while my man watches, and often he will pleasure my man: oral sex only – no intercourse is the rule. In the afterglow of a recent wonderful sex session (just the two of us) I remarked that of all the sexual combinations we had enjoyed I had never seen Roger suck another man’s cock. “Some of your...

4 years ago
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The Tomboy

This story is dedicated to my great friend BobbyLynn.I met Bobby when I was 18 and she was 9. I had just moved to Ohio from North Carolina. I was living with my older brother in his little two bedroom house. I had just graduated high school and was planning on going to the local Tech school to take auto mechanics. I already knew quite a bit about cars and spent most of my free time working on them. My brother, Todd owned his own auto shop and was letting me work for him doing what I did best. I...

First Time
1 year ago
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Schoolgirl and schoolboy

This story is a two part. We did it my way, then her way. Enjoy The first part is about how a schoolgirl fantasy, that I wanted to do with my girlfriend. The second part is how my girlfriend did the same kind of fantasy, but she had a twist of her own to do it. It all started, when we looking up costume on what to be for her Halloween company party. She wanted to be something sexy because everyone in her office think it's kind of boring, and she wants to change that. We were looking online and...

Straight
4 years ago
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Teaching the Tomboy

Based on the short story: SARA'S PUNISHMENT By Mr. Stefens The three buxom matrons marched Sara into the punishment room, one on either arm, the third trailing behind with a scowl on her face. "Get offa me!" Sara protested stridently as the two large women marched her toward the discipline horse. How delightful it was to encounter Sara again--and so soon. "Strap her down," I ordered with a sigh. While Sara twisted and struggled and mouthed indecipherable words at her tormentors, I sat...

1 year ago
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Tommie the Tomboy

After about ten minutes or so, I really lose track of time, Tommie is gasping. "Oh, Dave... Please... Whatever you're doing... Please... Don't stop... Make me... Oh, God... I'm close... Oh... Oh... I'm gonna..." As her vagina clamps down on my finger, I sucked her clitoris into my mouth and rolled it between my lips. She's gone completely silent, her back arched up off of the grass and all of her muscles are taut. Finally, she drops her back down in the grass and screams, "GOD!" so loud that it...

Mature
3 years ago
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Mama Papa und das Sissy Baby

Ich lebe noch immer mit meiner Stiefmutter in einem Haus. F?r mich war sie immer die Mama. Mama weckte mich und mein Bett war klatsch nass. Ich kann nicht sagen ob es daran lag das wir erst vor ein paar Monaten umgezogen sind oder an was auch immer aber es war mir mehr wie peinlich, denn ich war schon 22 Jahre alt. Mama zog das Bett ab. Am Abend setzten wir uns dann zusammen aufs Sofa. Sie sagte: Also ich finde wir m?ssen was ?ndern. Dann zeigte sie mir eine Windel und legte sie auf den T...

3 years ago
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Mama Bhanji Ki Bachapan Ki Masti

Hi mera nam suman hai mai mumbai me rahati hnu hum sirf 3 bahan hi hi hai mera koi bhai nahi hai mere pita jee mumbai me hi job karte hai meri hight 5.7 hai rang thoda sawala lekin sundarta me kami nahi haijaise lambe bal sina bahut bhara nahi hai to kam bhi nahi hai 32 ki size hai kamar 28 kali aankhe patale oth aadi mai baut dino se is site pe bahut sari kahaniya padhati aayi hnu maine socha kynu na apani bhi asali kahani post karu meri ma ko 3 bhai hai ek bada aur do chote mama log gaon me...

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