[M/M] Craigslist encounter with a transman

So this just happened yesterday and I’m getting hard just thinking about it. So I was on the casual encounters section of reddit and I decide to go into t4m. I’m 23, with a few extra pounds, black, with a pretty average sized penis(6”). Oh, and I’m bi. So I see an ad for a fwb situation so I wrote to him and after a few messages, we decided to meet for sushi over the weekend. The weekend comes and I’m super nervous. I actually lost my virginity to a transman but since then I’ve only been with one girl and two guys so I felt I was lacking in the experience department.

So I get to the sushi shop a few minutes late and I see him standing in front. I awkwardly stick my hand out and shake his and introduce myself. I hope I didn’t stutter. He’s about three inches shorter than me, about 5’9, has light brown hair and blue eyes, a real catch! I’m a bit nervous and I order only one roll and he does the same. The conversation has a few lulls in it, but it’s still good conversation. I’m getting to know him better and soon the waitress brings the bill. We pay and he suggests we go to the part to smoke a joint.

The day I learned to love sucking cock [F/M]

Until recently, I viewed blowjobs as more of a chore than a turn on. If a guy went down on me, or asked me to suck his dick, I would do it, but it wasn't something I enjoyed. This didn't really phase me; I figured blowjobs are meant to pleasure the guy, not the girl. I honestly didn't even think it was possible to get sexual pleasure from having a cock in your mouth.

I've been dating this guy, Andrew, for a few weeks now. It's pretty casual, but is going pretty well due to our frequent/quality sex. I've never met anyone that's loved eating pussy as much as he does. He'll come over to my apartment, ask me how my day is going, and throw me onto my bed. He'll unbutton my pants, and I'll slide my ass off the bed so he can pull my pants all the way. He starts kissing me down there, through my underwear. He used to pull pants and underwear off in one go, but changed after I jokingly complained that he doesn't get to see the panties I put on just for him. He took that seriously, and now makes a point of teasing me through my lace panties.

Not the morning she wanted to wake up to [non-con] [mf] [bondage] [blowjob]

Julia jolted awake as she felt the sensation of falling. Oh, thank god it was just a dream she thought as she tried to open her eyes and roll over. Very quickly she realised she could do neither of these things. At this point her head started to throb and the fragments of yesterdays events started to piece themselves together. She had been at a party and had gone outside onto the street to get some fresh air. It was then that she had felt something hit the back of her head and the cool embrace of a concrete floor. Julia couldn't helped but start to struggle against whatever was holding her in place, but all she was doing was wasting her energy. She was held firmly against the wall by steel cuffs that had been firmly bolted into place, she was essential spread eagle, upside down on the wall. Julia had no idea if she had been there for minutes or hours before she finally heard footsteps. "Help! Please! Someone help!" She cried out, desperately wanting to get out of her predicament. Unfortunately for Julia, this man was not going to help her. She heard his footsteps draw closer and closer to her before he finally removed the blindfold from her face with one firm pull. Now it was the light that blinded her, she was forced to shut her eyes so they could adjust the the bright lights that had been hooked up in the surprisingly modern basement. When her eyes finally adjusted she could just about see the man standing in front her, albeit the right way up. "So pure finally awake, sleepyhead," the imposing man joked. Even from this angle Julia could tell her was clearly much bigger than her, which wasn't difficult standing at only 5'2. "Wh…what have you done to me?" Julia asked, still trying to get a clear look at him which wasn't aided by her dizziness caused by blood rushing to her head. "Well I've chained you to the wall, I thought that would be obvious, you silly bitch," the man laughed to himself as he stepped away from her and started to strip down. Julia switched tactics, "please just let me go, I won't tell anyone what happened if you just let me leave," she begged, her voice breaking a little half way through as she started to fully realise her situation. The man laughed again. "Well you're right that you won't tell anyone, but thats because you'll be an obedient slave by the time I'm done with you. I advise you not to resist me, but hey if you do you're just gonna make things more fun for me." Julia could only whimper as her vision cleared up and she saw him standing directly in front of her, now completely naked. In a different situation she would've found him hot, he was tall and just a little bit more muscular than her ideal, although she couldn't quite see his face. What she could see quite clearly was his already hard cock, which made her quickly realise she was also naked. His cock looked bigger than anything she had had before and it was inches away from her upside down mouth. "Open wide, slut," the man ordered simply. Fearful of what he might do, Julia held her mouth open. "There's a good little whore," he smiled. Julia closed her eyes, expecting him to shove his throbbing cock into her mouth, but instead she felt him push something round into her mouth and wrap something around the back of her head. She looked up at him with a puzzled, but still fearful, look on her face. "Ring gag," he said, without her asking. "Learned my lesson never to take risks. The gag meant Julia had no way to resist as he pressed up against her and forced his cock into her open mouth. At this angle he couldn't fit all the way in, but he quickly hit the back of her throat, causing her to gag just a little. Once again the man laughed, embarassing her even more. "I had you pegged for a cocksucker and I was right, shame, I love hearing girls gag." Everything he said seemed to make her feel more and more degraded and the worst part was that part of her liked it. She had always been submissive, part of the reason she had such a slight gag reflex. Needless to say she was popular at college. His height meant his head was far above her pussy, but he brought one firm hand onto it as his other hand ran along her smooth skin, making her feel like a piece of meat. His thrusting continued, constantly making his cock hit the back of her throat. She didn't even notice, but she was licking and trying to suck at his cock as he fucked her mouth. "Damn, your cunt is already wet. This is gonna be easier than I thought slut," he started to work 2 fingers into her wet hole, forcing her to moan involuntarily around his cock as his fingers curled up to rub against her sensitive g spot. He continued fucking her face as his other hand moved to rub on her clit, only making her moan and struggle more as pleasure started to build up inside her. She struggled against her restraints to no avail, she was totally helpless to his cock and fingers. She felt herself about to cum, his fingers deep inside her and his cock at the back of her throat. The wave of pleasure was just about to crash over her then it stopped. His hands moved away from her now drenched pussy and he stepped back briefly allowing him to strike her across the chest, leaving a hand mark on her breast. She could do nothing but moan in total disappointment as he stopped playing with her, then in pain as his hand stung against her unimpressive chest. "No bitch cums before a man, do you understand?" He asked, his voice sterner than before. "Mmmhmm," she managed to moan out, his cock still deep in her mouth. Her mind cleared a little after getting so caught up in the anticipation of having an orgasm. Without going back to touching her pussy he continued to thrust into her mouth, the pleasure building inside his cock as he used her mouth. She couldn't help but feel so degraded and still, part of her loved every second. The cock in her mouth started to spasm and Julia tried to prepare herself to take his cum, but instead he pulled out and sprayed thick jets of cum up across her milky flesh. His moans filled her ears as she felt his cum coating her. His cum was plastered across her tits before it started to slowly roll back down onto her face. Once again she felt his cock pushed into her mouth. He didn't even need to give the instruction for her to lick it clean as she had done it for many different men. "I bet you want to cum after that, don't you, slut?" He asked, stepping back and grabbing his phone from a nearby table to take a picture of his latest art piece. Julia had felt her will slipping away the whole time. Her pussy was on fire and she was so desperate to cum. "Yes please," she practically begged. The normal part of her brain was screaming at her to resist what he wanted, but she didn't care anymore, she just needed to cum. "That's a good slut, but from now on call me sir. Go on then, cum." Julia looked confused for a moment, "I can't," she thought for a moment. "I need you to make me cum sir." "Don't you ever forget that, I control your pain and pleasure from now on," he reached up above her pussy and pulled down something she couldn't quite see from so low down. She quickly realised what it was after he pushed it against her clit and turned it on. He had hung a vibrator from the ceiling, so it dangled right between her legs. Immediately she let out an excited moan as the vibrations sent shocks of pleasure through her already wet pussy. Given everything that had happened and how completely humiliated she felt by him watching her moan breathlessly and struggle against her restraints it really didn't take long for the pleasure inside her to build up. She came harder than she had in a long time, her moans filled the small basement. "Thank you sir," Julia managed to say weakly, catching her breath. She could still feel the vibrator doing it's thing and the pleasure was already starting to build inside her. "You're welcome, my little slut." In the meantime he had gotten dressed and now he was heading to the basement stairs,"see ya later," he laughed once more. "Wait what?!" Julia half shouted,"take this thing off of me, I came." "First, mind your tone with me, whore and second, you asked me to make you cum, so thats what I'm doing. You'll learn pretty quickly that you belong to me, so I can do what I want with you," and with that he was gone, leaving her locked in a now pitch black, soundproofed basement, chained upside down, with a vibrator punishing her clit not stopped as she cried out helplessly.

My first time [m/m]

This is the true story of my first guy sex experience, an anonymous encounter at an adult bookstore. I'm NOT gay, btw…. :)

I attended a large midwestern university in the 80s. In town there was an adult bookstore which I and the guys in my fraternity would go to occasionally. We'd pile into a couple of cars and a dozen or so of us would go there for a laugh. They had probably 12 or 15 booths there, kind of arranged in a circle around a central area. They weren't that big but 4 or 5 of us would stuff ourselves into a booth and have a good laugh watching the videos.

I would also go by myself sometimes. I'd usually go during the day since the place was always deserted and it was less likely I'd see somebody I knew. These trips were not for a laugh, but so I could jerk off in the booths. I went as often as I could because I really got off on it. The booths sometimes smelled like come and I liked thinking about other guys jerking off in the booths before I got there. In fact, I'd seek out the booths in which I could either see or smell fresh come on the floor or wall. The booths all had paper towel dispensers and small waste cans in them, but usually the customers wouldn't clean up their come. If it was on the wall or the screen, I'd run my finger through the goo and touch it to my lips. A couple of times it was still warm and I knew it was fresh, and I'd lick some off.

Risky sex with the Japanese student teacher

Skip ahead to SEXY TIMES if so inclined.

Midori

When I was in my 20s, I moved to Japan to work as an English teacher in the north. I worked in many different settings but spent most of my time in a sort of community college. Every year at our school, we would hire 6 college education majors in their senior year for some hands-on experience. They worked with us for a year at a time, learning English and American-style education while assisting us with our duties.

The Japanese academic year starts in April and essentially goes year-round. In July and August of every year, a new set of Japanese recruits would rotate through our school for one week at a time as part of the interviewing process to start working at our school the next spring. Some of the applicants were older, more experienced teachers, but most of them were juniors and seniors in college.

Nailing the Temp

I travel a lot. I own my own appraisal company specializing in large manufacturing plants. Sometimes I'll be away from home for weeks at a time as I examine plants in preparation for an appraisal. Since I travel so much, I really don't have time for a relationship in my home city. It's sad, but I will often spend an evening at a strip club just to feel the fake personal connection. My business is my life and hopefully someday I'll be successful enough to slow down, but for now it's go, go,go.

On a particularly large job in Oklahoma City, I decided I needed some help. The plant was exceptionally dirty so I called a day-labor type temp agency and asked for someone who could do some minor cleaning around critical parts of the machinery that I needed to see clearly in order to assign a value in my report. They sent me Katrina. Kat, as she liked to be called, was not at all the type of person who normally does the day labor gig. She was short and maybe 110lb soaking wet. Her long brown hair was tied back in a no nonsense pony tail, her plain blue T-shirt fit loosely over her B-cup boobs. The jeans she wore had some small tears and hugged her round ass tightly. She wore simple plastic-framed glasses that really set off her eyes. I was very happy to be spending the day with her and hopefully the week. My professionalism kicked in and I explained what I needed her to do. She learned quickly.

Testing [MM, exh, oral, reluc]

"Ready?" she asked.

I took a deep breath and swallowed. "Ready."

I felt a slight tug of pressure on my pants as my zipper was pulled down. A hand reached through my open fly, and quickly found its prize, gripping my flaccid cock, pulling it out of my boxers. Corina lightly gasped at the sight of it, thick and heavy. The hand stroked my shaft delicately, coaxing me to an erection, its fingertips gently grazing my shaft. Slowly, I grew harder, larger, my cock eager. I stared up at the ceiling as my manhood was engulfed by a warm, tight mouth.

Corina smiled as she watched me squirming on the bed. I gritted my teeth and gripped the sheets. "Are you okay, John?" she asked innocently.

"Y-yeah," I stammered.

She looked down at the young man sucking my cock, whose name I had no desire to learn. Her grin broadened, her eyes wide, as she watched. He held my cock with one hand as he bobbed his head up and down, his tongue swirling around my head with practiced talent. She smirked. "I thought you said a guy could never make you cum," she reminded me. "You're not worried, are you?"

An Innocent’s Gradual Descent: Sum[m]er [f]un

Heads up, this is going to be a long story with lots of detail. May continue with other memories of Summer later.


The summer before I turned 17 I was a counselor at a summer camp. The weeks leading up to the camp, I got together with all of the other counselors over the weekends to plan some of the events and activities we would be running in a few weeks time. Thats where I first met Summer.

She was a short and gorgeous brunette. She was my good friends cousin and I had been told of her joining out team of counselors. She was a dancer, with legs pale and lean. Her face was round, large brown doe-eyes framed by shoulder length brown hair. She was fit no doubt about it and she had the largest breasts I had ever seen, DDs fit snugly into a rather conservative top. She was the epitome of innocent beauty.

Summer's cousin, Ashley (a good friend of mine), had given me some background in that she had never actually gone to a sleep away camp before but was excited to be staffing one. Summer had moved a couple years prior from South Africa and lived with her family in Colorado.

Sophomore Year (F)un part 4 [fm] long

Tim and I left for the two hour ride ahead of us to his parents lake house. Tim offered to drive so we got in his suv and got on the road. We talked about anything and everything and the conversation of his fantasy came up again and he asked me mine.

I described to him my new found fantasy that Jake had sort of brought out in me. I described to him how I enjoyed giving blowjobs and how being outside or in public turned me on.

The whole time I'm describing this to him I can see him adjusting himself out of the corner of my eye. I decided to tell him how I gave Jake a blowjob in the car and described to him how I snuck my foot into his lap under the table. I looked down at Tims crotch and could see his dick pushing against the fabric of his jeans.

I placed my hand on his thigh and didn't hesitate to run it over his hard cock. I could see him look down with approval so I decided to release his pain and undo his zipper. I reached down his fly and fished out his member until it was exposed and pulsing in my hand.

[F]irst time with [m]y best friend

So, this is my first post on reddit (this is my naughty account obviously). Thought I might as well start here. And yes, all of this is a completely true story. I honestly still think about this first time today since it was just that awesome. (names obviously changed for privacy)

Clara and I were best friends and had liked each other for years but never told each other. I would give her friendly tickles, she would casually stroke my leg while we were studying in university. But we were both shy so we never told each other we liked each other and we ended up both dating other people. We kind of were the ones we would go to when we each had sex issues that we wanted to talk about. She would come to me with her guy issues when she wanted to know how to better please a man and I would go to her about how to please women. Years later, we ended up going our separate ways and she moved away from Toronto. We still kept in touch and flirted over Skype but neither of us made the first move. Years later, she came back to Toronto to visit me and stayed with me. We knew she'd be leaving again in a few weeks. And for the first time, we were both single at the same time. Things got really hot.