[GAY] My (M32) first gay experience (m25)

I am no stranger to kinky sex – sex with strangers, in public, or crossing new boundaries; this story is all three.

A few years back I was dating this girl (name not important) and while she was alright, she was a massive cheater who regularly went out to find some new dick instead of keeping it at home. After the 2nd time, I got tired of her shit and dumped her. Her roommate, Eli, was a twinky fun-loving gay man that had lived with her for the majority of the time we were together.

During parties at her place he would always quiz me why I’d never tried to swing the other way, and I admitted on a couple of occasions that I’d kissed a guy here and there but never dove in head-first. He would flirt playfully, but kept our boundaries intact since he was respectful like that. He was shorter than me, maybe 5′ 7″ and very thin. He always wore light makeup and more feminine clothing. He kept his short crop of black hair very clean and always had a great smile. I, on the other hand was a little more of a man’s man. I am 6′ 1″ and fairly fit, but not buff. I typically wore the same blue jeans and style of flannel shirt everyday, but he said he liked the idea of “being able to turn a straight gay” so it didn’t bother me that we were too different.

[f]ucking my g[f] during a snowstorm [ff]

Writing this directly after it happened to preserve the memory :) I’ve never written anything like this before so…You can see my profile for what I look like, and my girlfriend is roughly 5’3 and mixed Latinx with brown curls, a lean petite body, and big tits. She’s beautiful with big lips, big brown-green eyes, and a bright smile. EDIT: I’m 21 and she’s 20.

We were sitting on the couch watching a movie after smoking and drinking on a Friday night snowed in. We had watched some TV, played video games, and smoked plenty as snow fell and we knew we had no responsibilities the next day.

It wasn’t long before we were both feeling buzzed from the weed and feeling not only each other but ourselves. My girlfriend, we’ll call her Anne, had stripped down to her underwear by this point as her body temperature raised with alcohol consumption. Her big, brown tits swung when she moved, and I couldn’t resist sucking on her always hard nipples whenever they were within reach. Anne reached over and began to finger my clit over my leggings as I felt her pussy through her panties. I moaned softly as I sucked on her tit and her fingers pressed against my opening over my leggings.

From the Straight POV. How it all started part 1

Danny and I have been friends from grade school. I think I
was the first to know he was into guys. He would still date girls but he told
me he was into guys also. I didn’t use to call him bi as I had never seen him
with a guy only girls. But he would tell me from time to time he was going out
on a date with a guy.

We were in a small town so I get hiding it close to home.
But I moved to the next state over and was going to college.  A couple of years later Danny wanted to go
back to school. He got in my same school and I asked him if he wanted to leave
with me.

My last roommate was a slob. And I knew Danny was a neat
freak. To tell the truth I was hoping her would help keep me clean. Lol
So, he moved in. and what a great roommate.

[MM] 30 First Time playing with another man

I’ve been bi curious for a long time and frequently get off to pictures of cock. Up until now I’ve gotten myself horny enough to even post on Craigslist when it was a thing and double list. I’ve talked with a few guys but when it came down to meeting up I always chickened out.

One day I got so horny that I posted on doublelist and began talking and trading pictures. For this we will say his name was James. James is a little older then me and gay. Throughout our conversation and picture exchanging I told him that I was curious about sucking cock and the idea of it turned me on so much. He offered help me out with my curiosity and for some reason I said yes. I told him how I wanted to fee a cock in my mouth and 69 with him.

We agreed to meet up an hour or so later and he promised to be chill and easy going. I give him my address and he says he’s going to shower and get ready then come over. My heart is racing at this point. Am I really going through with this? At the same point I’m rock hard and determined to go through with it.

Drive-In Blues: Chapter Five [Gay/Hypnosis/Feminization]

Chapter Five: Question

[Warning: Heavy Themes of Mind Break and Non-Consent]

As Ian woke up again, it occurred to him that he had spent the last two days doing nothing except fucking and sleeping. That was probably by design. Better to keep them asleep when their master didn’t have them busy, no time for plans. Ian then realized he had changed clothes since passing out.

Ian groaned and put his face in his hands. Both him and Alex were wearing dark red silk night gowns with black lace, that went just passed their asses. Light from the window showed that it was a little passed sunrise now. It meant that there could be a whole host of new triggers that he and Alex had no way to prepare for.

There was a knock at the door, and Ian went over to look through the peep hole. Before he could, his hand automatically unlocked the door. It opened and Izzy walked in with a big smile. This time she was wearing yoga pants and a long sleeve sweatshirt. “Morning sleepy heads! It’s a bit chilly out there today so I suggest wearing coats when we go out. Luckily I brought some really cute ones for you” ian looked down at the suitcase she dragged in, and gasped in surprise.

My first time with a guy…(M)

I knew from my teens I was attracted to guys. It was confusing to me because I had been with plenty of girls and loved every second of it. I never acted on that attraction until my early 20’s. I didn’t have the nerve to ask or talk about it with friends that were bi or gay. I had a friend, Mike, who was bi, but mostly was with guys. One night, with a group of friends we were talking about music and concerts we’ve been to and I mentioned I was going to see a local band that was pretty good the next night. He asked if I minded if he went along. I said yeah, let’s go. So the next night we met up at the venue, had a great night, good music, a few cocktails. Neither one of us felt
like it would be a good idea to drive so we called a cab. His place was only a couple miles away and he suggested I just crash at his apartment and we’ll get our cars in the morning. It didn’t really cross my mind at the time about the two of us getting together, well not totally. He was an attractive guy, easy going and fun to hang out with. So at his place, we were just hanging out, talking with a movie going in the background. We started talking about past relationships, good ones, bad ones, fun ones. He had stories about guys, mine were of just past girlfriends or short flings. I was interested in his guy relationships of course. And kind of steered it that way. Now, a few more drinks in at this point and feeling a bit brave to start discussing my hidden side. So, I just came out and said it. “I’m attracted to men”. His eyebrows raised…”really?” I said yeah, for years but never acted on it or told anyone. He says with that “did you just come out to me?” His voice cracked a bit. No going back at this point I thought. I asked about his first time and listened intently. We were on his couch, now kinda facing each other. I figured screw it and moved a little closer and put my hand on the cushion near his knee. He noticed, but looked a little reluctant. He told me later, he didn’t want me to feel rushed or taken advantage of. But at this point I was all in. With one finger I touched his leg, I felt it instantly, I wanted him to be my first. Now, I was never an aggressively forward person, but like I said, all in. I told him that right then. He asked what I wanted to try, I just asked “can I rub you through your jeans?” He moves his hips forward a bit and dropped his right knee, his bulge was quite noticeable. I reached forward and with the tips of my fingers caressed his tight jeans. He gave a smile and said “what do you think?” I then moved closer and cupped his crotch, he pushed back a bit. I felt his bulge get bigger. “Want it out?” I returned with an enthusiastic yes. He undid his button and unzipped. His blue boxer briefs clearly bulging out. He adjusted, pulling the briefs down revealing his growing cock. I was impressed with size. A bit bigger than me and very nice looking. I lightly touched his head and shaft. His cock throbbed at the gentle touch. I started to lightly stroke from head to base as he watched and smiled. After a minute he lifted his hips and dropped is jeans and underwear to the floor. He spread his legs open, his cock and balls out in full view. My cock was swelling and I had to unzip to relieve the pressure. I moved in close and gripped his cock. He gave a slight moan. I stroked him harder as my cock started to throb. He said “get those jeans off”. I stood up and complied as we both stripped our shirts off as well. I moved in and dropped to my knees, my face to his chest and hand on his sides. I kissed his chest feeling his hard cock against me. His hands at the back of my head I slowly moved down. The head of his cock at my lips I took my first ever taste of another guy. He took a deep breathe as I kissed and tongued the head. I went further down taking him deeper and gripping the base. I was finally feeling what I imagined all those years. I got lost in the moment as I sucked fast and harder, he moaned and caressed the back of my head. I could tell he was getting close as his hips thrusted with my rhythm. He gripped me hard as I felt the pulsating of his cum in my mouth. He moaned loudly as he gushed. I had to swallow as it shot to my throat. I stopped and backed up to the floor, leaning on my hands. Watching him relax and smile. He said “was that really your first time?” I just smiled still enjoying the taste of his sweet cum. He patted the couch cushion and said “your turn”…

The time I [M26] and my lesbian best friend [F25] hooked up and it was the best sex of my life [MF]

Hey guys. This is a repost of my first story I ever posted. I took it down for a number of reasons, mostly the weird DMs I was getting. You guys are welcome to ask anything just be respectful.

So to start off let me say that me and my friend, let’s call .her Jessica have been friends for a while and there is no awkwardness between us. We have seen eachother naked dozens of times and have while we both have admitted we think the other attractive it has never gone past complimenting one another cause well compliment your friends, I’m sure they’d appreciate it once in a while. We also go out regularly (pre covid) and wingman for eachother. Anyway on to the story.

One day she comes over and we are just hanging out in my room watching a movie and she mentions that she saw a hilarious porno parody and asked me if I wanted to see it and I was like “son of a bitch…I’m in”. You the the ones. They are all horribly bad but you still laugh your ass off. So we start playing it and about halfway through we get to this one actress we both find fucking HOT! So needless to say we both wind up getting really turned on.

My only (sort of) gay experience [FM]

I was dating this girl who was incredibly dominant and she was really into ass play and she would make me cum with ass play without ever touching my dick. So she bought a vibrating butt plug that she could control from her phone. It started out with her just making me wear it like out to dinner and stuff but one night we went out to dinner and I was wearing it she was teasing me the whole time and we got pretty drunk on wine and she says Let’s go out I know a really fun place near by.

We walk in and it’s a gay club like all dudes drunk just grinding hard on each other. At this point in our relationship I was full submissive so she is in control. After we walk in and get a drink a he gets me hard with the butt plug and say go grind on a guy now slut. Not bragging but I do have a nice dick so when I went and started grinding on this little twink guy he could definitely feel it. We are grinding for a minute and not gonna lie it felt really good. After a few minutes I feel the vibe turn back on and try to pull away from this guy but look back at her and she shakes her head no. At this point I know I’m gonna cum soon so I figure there is no point in fighting it so I grabbed his hips and whispered in his ear please don’t stop. At this point he knew I was going to cum and he really started to work my cock with his ass. I came so hard I almost fell to the ground.

A Gay Bar [MM] 20’s

This is obviously not my story but a gay couple I know asked me to write a story about how they met and I was happy to oblige!

I went to this gay club in town called crews and tangos in downtown Toronto, I had not been out in months and I thought why not?  Went in and sat at the bar ordered a drink while watching the local drag queens put on their performances. 
I forgot how fun it was to come here.  The queens also put on an amazing show.  An hour went by and I was going to call it a night when a guy approached me. He was tall, blonde and brown eyed.  Light stubble on his face very attractive.

“Were you leaving? I just got the courage to come talk to you…”

I smirked and said  “ I might be persuaded to stay”

He smiled showing perfect white teeth and full lips.  He replied  
“ I think I could do that, I’m Adam”

“ I’m Dean, good show huh?”

“Oh yea definitely. They work really hard”

Miss Hart

This happens after The First but before The Twin.

Andrew: Photographer at Large: Miss Hart
[See the other parts here.](https://www.reddit.com/user/JerryDunlop2/comments/rti8t3/the_order_of_things_for_andrew_photographer_at/)

It was Saturday morning and Andrew had been looking forward to this all week, last Saturday he had fucked Miss Hart’s friend Fleur who was also a life drawing model and today he was fucking Miss Hart, well he was about 99% sure he was, let’s say sure enough. He had tidied the house the night before and it was immaculate. He had also groomed himself, nearly exfoliated himself raw and trimmed his pubes which had somehow made his dick look even bigger. He bought some condoms just in case and made sure he had plenty of lube and paper towels beside the bed. He was nervous because last time he didn’t have time to be nervous, the adrenaline and pure fucking lust took over, plus he also liked Miss Hart as a person as well as finding her very physically attractive. The hair, the tits, the legs and of course the face. They hadn’t actually arranged a time, just that she would be there in the morning after she got up. Andrew had been up since 8am but it’s not like he didn’t have anything to do, there was always developing or printing to do as well as scanning and adding to his website. Serena was still loitering around the house even though Andrew told her what was most likely going to happen, she was going to go out with friends and spend her day at the mall anyway. She finally left and Andrew felt a little less anxious. He had been walking around with a semi in his pants all morning and wondered if he had time to rub one out before she arrived. He was just about to get down to business in his bedroom when he heard a *dring-dring* from outside.