r/GayFirstTimeStories

So this happened recently, and i keep thinking about it, so wanted to write it down:

I started chatting with an older hispanic guy (late 60s, i am 29) and we kinda hit it off. He told me he likes to meet with boys who haven’t had a lot of experience and help them find their gay side.  that kind of excited me, i am new to this, he likes it with newer guys.  After chatting for a few weeks, we met up with the plan of driving into the mountains, which are nearby, and jerking each other off.

We met in a parking lot near my house and I got in his car. At his request, I wore a skirt and thong which I had bought for the occasion. It was so weird, and so hot being in public wearing it, even if it was late at night. Once I got in, he had his dick out and suggested I touch it as an icebreaker. I was very shy, didn't at first. We began driving, his dick still out, and we kind of went back-and-forth as we were driving out to the mountain. it was so hot though.  big, uncut, i loved it.  After a couple lights, I decided it was dark and no one would see anyways, so I might as well. I reached over and began touching his dick. He told me how good it felt, and I kept spitting on my hand and stroking his cock until we got out closer to the mountain. At that point, we pulled into a dark area and he moved his seat back a little bit.

While I was stroking his cock, he had made comments about how i know i am meant to be gay, or how i was meant for men. He said how sub men like me, sissies like me are meant for dick. Once we stopped, he began telling me to taste his dick, i want to, why fight it. i said a few times i was just going to give him a hj. After a few times saying it though, I felt like he was probably right, and i was so turned on by the soft verbal abuse. I ended up opening my mouth and wrapping it around him. The comments about me being gay, sissy, began coming more and more, which really turned me on.  i would look up and suck his dick, and he would tell me how boys like me are such faggots.  he said he had grandkids my age, but they aren't cocksuckers like me.  i wanted him so bad.  I kept going up and down on his cock.

Eventually, his hand wandered to my ass, and he slipped his finger inside me. reminding me straight boys don't let men finger them.  it hurt, but i was so turned on. i had only done that once. he told my to jerk off. i did, and came so quick, with his dick in my mouth and fingers in my ass.  he caught some cum and had me lick it off his fingers. A little after, he held my head down and came in my mouth.  I swallowed him, After that, he drove me back to my car and told me he knew that I was a little faggot Inside and I did a good job. Once we got to the parking lot, it was really empty because it was in the middle of the night, so I gave him head one more time and then went home.

I was sneaking over there every chance I could sucking him off. Then one night as I was sucking him off. He asked me if I would lay on top of him naked. I said probably not but he kept asking so I gave in. I undressed and layed on him. He told me to grab his cock and rest it right between my ass cheeks. I told him I'm not having sex with him he said he just want to feel it on my bare ass. So I put it there. He started moving me back and forth. Thrusting his hips up. His precum lubed up my hole. I told him that's enough as I went to get off of him I pushed up and he latched onto my nipple started sucking on it. I've never felt that feeling of electricity jolt through my body. It was amazing I started moaning like a little slut. The kept sucking and thrusting his hips up into my ass cheeks. I don't know what came over me. He was sucking my nipple so good the when he thrusted up I pushed down and his cock slid right in to my asshole. I yelled out because I've never been fucked before. He held me tightly so I couldn't get off. I was crying but he was telling me to relax and breathe. I had no choice he wouldn't let go. We layed there for a few minutes. Then he started moving up and down slowly let my ass get stretched out my his big cock. It started to feel so good that I asked him to let go so I can ride it. He let go and I moved my hips back and forth to his rhythm. Feeling every inch of that cock going deep in me. He moved at a quicker pace telling me he's going to cum. I moved faster as his cock started throbbing harder all of sudden I hear him take a deep breath in and felt his big mushroom head shoot that warm load up in my ass. It felt amazing.

So it happened when I just turned 18. My friends would always talk about a old man who lived in a trailer park not far from where I lived. They said he would take his cock out after he invited you in his place. I never believed them. We were always making things up. But curiosities got the best of me one night. After I left my friends house playing video games. I was riding my bike back home when I thought to myself let's go see if the stories are true. So I rode my bike down a trail through the woods that lead to his house. I got there and knocked on the door. I heard him say come in so I walked in and he was sitting in his living room on the couch. He told me to close the door and come over to the living room. I say he was in his late 50's early 60's. I sat across from him in a chair. He asked what I was doing,it so late?I told him I was going home but heard stories about him. He said oh, really like what, right when I was about to hell him, he pulled his cock out. He said stories about this. It was such a big thick cock. Easily 8in and thick. I got wide eyed because I've seen cocks before but just my friends. Nothing like that big in person just in porn. He asked me to come over and sit by him so I did. I just kept staring at his cock I was in awe of it. He was stroking it keeping it so hard. Then he asked if I've ever seen or touched a cock that big. I told him no and he asked if I wanted to. I wanted to touch it so bad but was scared to and my heart was beating so fast. He asked again I said maybe then he grabbed my hand and made me grip it. I went to pull my hand away and he had ahold of my wrist and started to make me jerk him off. I finally gave in and started doing it on my own. He put his head back and started moaning telling me it felt so good. His cock was so thick that I couldn't grip all the way around it. He was leaking so much precum and so was I. I had a little hard on and he seen it poking through my shorts. He said to me oh you like jacking me off,I shook my head yes because I couldn't get the words out. Then he asked if I wanted to kiss it. I told him no, then he said you are already stroking it, just give it a little kiss that's all. Being a naive kid I said ok. So I leaned over and put my lips on it. The musky smell on his hard cock and big balls turned me on even more. When I went to bring my head back up he told me to stay there a little longer and keep kissing the tip. So I stayed and was kissing the top tasting his precum. I had ever tasted anything like that before but I liked it. He keep moaning telling me I'm such a good boy for kissing his cock, then he said to stick out my tongue and lick his shaft so I did. He was teaching me how to lick his cock because he knew I was just learning. He had me licking up and down his shaft and balls.Tasting the precum from the tip. I was doing that for a good 20 mins when he told me to open my mouth and told him no when all of a sudden he grabbed the back of my head pushing it down saying open your mouth now, so I did and he slowly started pushing the thick mushroom head of his cock in my mouth. He told me to open wider so I opened a wide as I could and he pushed more of his cock in. I heard him say damn you have a tight mouth feels like a virgin pussy. He guided me off the couch to my knees. He stood up and started pumping his cock in mouth telling me to suck it like I was sucking on a popsicle so I did. He was moaning more and more thrusting faster making gag as he hit the back of my throat. He started calling me a good little cock sucker as he was getting closer to blowing his load. I felt his cock start pulsating, I didn't know that meant he was going to cum. He held my head on his cock as I started to gag on the streams of cum that was shooting in my mouth. I had no choice but to swallow it. He fell back on his couch out of breath thanking me for being his little cock sucker. I had so much precum in my underwear I thought I had came in my shorts. It was an amazing experience that night.

So after that first time it had been a few weeks since I'd gone back. You know how it is. I was in shock that it actually happened. My mind was racing about what I did and what did this mean. Well I could stop thinking about it. So one night I snuck out of the house. I still lived with my parents. Rode my bike back through woods to his trailer. I wasn't sure if he'd be awake it was pretty late at night. I walked up through the trees I seen his lights on. I knocked quietly on the door and heard him say come in. I walked in the house and looked over to the living room. He wasn't sitting on the couch, he said over here. I look to my right he was in his bedroom. Lying naked with a massive hard on. I got so super nervous again. I said "oh you're going to bed" I'll just go then. He said come sit down. I was frozen with a deer in the headlights look. He said "don't be scared, I was wondering if you were ever coming back". It's been a long time since the last time you were here. I lied and told him I'd been busy. I finally worked up the courage to step into his bedroom. I was still standing there staring at his hard cock. He said again sit down, so I finally did. He asked me what I was doing there so late. I answered I don't know I'll should go. He asked if I wanted to touch his cock again. I shook my head yes. He put lube on my hand and I began to jack him off. He told me too slow down and enjoy feeling his throbbing cock. I was staring at his big cock in my hand. I don't know what came over me but I opened my mouth and engulfed his fat cock. He moaned and said there's my good cock sucker. Again I got a hard on leaking in my shorts. I was on all fours in his bed sucking it. Tasting the precum leaking out his tip. I felt his cock pulsating faster and I remembered what that meant. His breathing getting faster and pumping harder. He put his hands on the back of my head pushing it all the way in as he started to cum. I couldn't breathe I was choking on it. He finally stopped shouting cum and let me back up. Cum leaking out of my mouth I took a deep breath. He was happy he told me that he's been waiting for me to go back so he blow his load down my throat. As I was cleaning off my face from cum and tears getting ready to walk out. He told me that he had been telling some of his friends about my first visit. I got so wide eyed he told me not to worry they won't say anything to anybody. But they want to meet me sometime. So I have more first time stores to tell.

I was looking for my first stranger hookup and gay hookup sites. Some guy texted me. He was about 52 and I was 18 at the time. We talked for a while and then decided to meet and he told me to wear a pair of my mom’s underwear.
I met up with him in a dark empty parking lot. I got in his back seat and he pulled my pants down and i was wearing panties. A g-string to be specific.
He slid them over and ate my ass for a while. then he pulled his dick out of his jeans zipper and i started sucking it. It had a musty smell to it like he hadn’t showered for a few days but i loved it. He almost came from me sucking his cock until he told me to bend over.
Then he shoved his thick cock inside me. it was so big. he ended up cumming inside me and then he jerked me off till i came all over myself and it even got on my face.
Then i got out of the car with just my g-string on because he said he was keeping my pants and i was just standing there seeing him drive away with his cum still inside my ass and just a g-string and shirt. i absolutely loved that feeling. i got back in my car and drove home. thankfully my family wasn’t home because i walked back into my house in a g-string.

Really just wanna make this a short and sexy story for hump day.

So my best friend and I just graduated high school and our first year out of high school we were living with each other and working at the same place. By this time we’ve been working for the same company and we were commuting to work, which was a little far. So we convinced his mom to get us a hotel room for a week closer to work so we could walk to work.

Sunday night comes and we check in to the hotel room; we get up there unpack get situated go down for dinner and talk about our week. Fast forward to Tuesday night, we got off of work, It’s hot out here in Palm Springs and we both wanted to take a shower after work. We both were so fed up with the day and how hot it was outside. We just said fuck it and hoped in the shower together. Keep in mind this is a big 6 to 8 person shower at Agua Caliente Casino in rancho mirage. So we’re both on opposite sides of the shower and we tell each other don’t look 😂.

I am in the middle of rinsing the soap off of my hair and body, and I open my eyes and catch him looking at me with his cock super hard. I instantly got nervous and was like what in the hell! He’s like sorry man. I’m just gonna be honest this looks super sexy. I shrug it off and I’m about to get out, when he walks over to me and asked me to sit down on the bench in the shower. I’m like why do I need to sit down on the bench? He’s like just trust me. So I sit down on the bench, still completely naked, and as a lean back, he just starts deep throating my hard, veiny,
pierced cock (I got it pierced my first year out of high school). I am so nervous I don’t even know what to do.

I grab his head and my cock comes out of his mouth and he makes that sexy slurping sound; and he asked me is everything OK? Does it not feel good? I’m like dude it feels super good, but I don’t think we should be doing this. He’s like just relax. Let me take care of you. So he proceeded to deep throat my cock all the way to my balls!!

He pulls my cock out of his mouth, a second time and stands up. As he does that, I follow and stand up too. He said let’s dry off really quick. we proceed to dry off and both of our dicks are as hard as concrete. He pushes me on the bed and then we get into 69 and start sucking each other off. After a few minutes of that, he gets on all fours and tells me to put my hard cock inside of him. I’m so nervous, I’m shaking at this point and my mouth is dry!

He’s like dude it’s all good, take a breath haha. Just fuck me as hard as you want and come inside of my tight little hole. Let me tell you that was the fastest I’ve ever cum!

I’m legit getting hard typing this!

*edit( I guess it needs an ending) 😂

— so now that I’ve finished and my body is all tingly. He asked me to put my legs on his shoulders while he slowly shoves his hard cock inside of me. Let me tell you anal hurts lol! But how passionate and sexy that was to feel his hard cock inside of me and throbbing as he finished! The next morning before work, we wake up act like nothing happened, and from my moment forward once we got done with work, we would shower and mess around in the shower! I haven’t talked to my best friend in a while unfortunately, I’m sure he’s doing well but I know a few years ago when I talked about the story, we swapped pictures and videos thinking about this day. He said it still gets him off.

If you guys are in the Palm Springs area message me. Also if you want more stories or to share DM me.

I was a 18 (now 30) and went to an adult store in another town to buy a pocket pussy. I got one and the cashier asked if I wanted to use the booths to try it. I said “I’m allowed to do that??”. He explained the “private” booths and gave me free credits so I went in. Thinking it was private I stripped fully nude, sat down and began going at on the toy. After a couple minutes I see a shadow in the doorway. I tried to ignore it but I slowly saw it creep around until I see what I think is a dick. I paused and leaned, stared at it to make out if I was seeing something. An older guy turned in, stroking his dick. I froze and he grabbed my toy and continued stroking me. I let him cause tbh it felt good. He continued for a bit and slipped a finger in my ass. After a while he stood up with his dick at my face, grabbed my head, and I froze. Within a second his tip in my mouth and he slowly pushed it back till it hit my throat. He moved my head back and forth for what seemed like 15 mins. Another guy wandered in during this and began using my toy on me again. The guy came in my throat. I coughed and it covered me and before I could catch my breath, the other guys tip was at my face now. He pushed it in and assured he came quick.I figured I would actually try sucking to get him done quicker. Hesaid he was about to finish and offered $20 to let him do it on my back bent over. I said sure and bent over. He pressed his tip to my butthole while stroking (I didn’t know that’s what he meant), after a few seconds he pushed his tip in, I grunted in pain, and he said “oh shit I didn’t meant to actually go in, how about $50 to finish in you? It’ll be a couple pumps” I didn’t wanna agree but did. He slowly slid in and out and came within one video. He pulled out, I just got dressed still covered in cum and left in a hurry. I could taste the cum and feel it leaking out the whole way home. Haven’t done anything like it since but i do want a pocket pussy again

o as me and my best friend had a night out having a party night we decided meet an old friend who gave us some Molly. After we took them we decided to go for a walk and enjoy the trip. After walking randomly around for like 20 min we decided to chill on a nice hill with a viewpoint with a bench to chill. After sitting there for a while in silence I saw him looking at some Reddit pages of some hot Girls and thought it to be a good idea and did the same. Then i saw him pull his Dick out and starting to wank, which was pretty Hot. After looking at him for some time i did the same. We looked at me at gave me a smile, a couple if minutes later he reached to my dick and started waking mine and I did the same with his Dick. Then suddenly without a word he just went to his knees and started sucking me off. It was my first time doing anything sexual with a guy. I then thought to myself „fuck it I want to try aswell“ and then started sucking him off aswell. It was amazing and i really enjoyed it. We both ended up cumming on the floor and ended up chilling there and went home soon after. We never talked about it but i can t stop thinking about it as i quite enjoyed it.

Hope you like my story

So this happened about 3 weeks ago, and I still haven't said anything to anyone and I cannot hold it in anymore...

Me Jake (29), My bestfriend Adam (29), and out two friends Chelsea (30) and Amanda (28) we're all hanging out at my camp (parents own it, and its more like a a small house on the lake) ... we had a small bonfire, and then decided to get into the sauna... we were all drinking and Chelsea said "Let's do this naked" and took her top off, then Amanda did the same... then the took their bottoms off. Chelsea then said "Come on boys" and Adam took his shorts off and he was so damn hard.

*I've never thought of a cock as something as attractive up until this point*

It was so hot, he was probably 8 inches, nice curve, well groomed, and Ahhh, he probably got hard from the girls, I got hard looking at his cock... to be honest.

We got naked, goofed around, had some drinks and jumped in the lake to cool off. We went to the house afterwards and all sat around in our towels and started playing truth or dare like we were younger. Basic bull shit back and forth for a bit till Adam got Chelsea and Amanda to kiss, and then Chelsea dared me to kiss Adam, so we did and made it quick... one dare lead to another and we were all bare naked in the living room with a fire going in the fire place...

Adam dared Chelsea to touch Amanda... she did... then Amanda dared to be jerk off Adam.... I was hesitant but so ready... I put my hand around his cock and started stroking... and obviously someone saw me get super hard. Chelsea said completely out of game "Truth Jake, why did you just get so hard touching Adam" and then Amanda said "You're blushing you clearly like that" ... I said nothing, and said lets continued the game... but I stroked Adam for another minute or so... I did really like it...

Then next thing you know, Chelsea dared me to get a cock smack from Adam, and then Amanda joined it, no just put it in your mouth, I want to see.... I was so nervous and was like "naa" and he's like "Cant back out on a dare" .... which just turned me on...

So I said fuck it, got down on my knees and they yelled, do it like you'd want it... so I put his balls in my mouth, and sucked on them, while stroking him, then licked up and down the shaft, and then used my tongue to play with the head... then put it in my mouth and never felt so horny... I stroked him and sucked him and I attempted a deep throat... till he was like "Im gonna cum" and I pressed farther down and got his load all down my throat and I absolutely loved it.

Game wrapped up shortly after that, we went to bed, there was two bed rooms with two twin beds. Girls had one, guys had one. We were about to sleep and Adam asked me to come to his bed, so I did, we started cuddling and he got hard, so I couldn't help myself but to touch him again... and then I just wanted to suck him again, so I did. Got him to cum in my mouth again.

Then we went to bed cuddling !

So I made a post yesterday asking for advice about having sex for the first time and id like to thank everyone who gave advice.

This is the followup

So we had arranged to meet up at a coffee shop first to make sure he wasn't a serial killer haha then we headed to his place. He offered to drive so that's what we did. During the 5ish min drive I was just super nervous but had a hard on basically the whole time haha (might have been a semi but I was definitely leaking). We got to his place and just chatted a little first to see what I was comfortable with, we then headed into a room where the 'magic happened' so to speak. We started getting undressed (I was hard the whole time btw) and he started touching my cock, and guided me to the bed where he asked to 69. He rimmed me while I sucked him. I sat on his face and my crotch just rested on his chest which felt so warm. After a little bit he asked it i wanted to ride to which I requested to do doggy instead. We used coconut oil as lube for those wandering.

He was definitely thicker than I had expected so it took a bit of convincing to get it in, but once it was it boy did it feel great. My ass was up and my face deep inside a pillow. And well he kept at it, I must say that I didn't expect to be moaning but It came out naturally haha. He was just slowly ramming into me and I loved the feeling of his balls just slapping me each time haha. The whole time I was just hoping that I wouldn't cum first, I did come close a few times and it definitely showed as I was leaking pre everywhere. In the end he came deep inside and I felt everything haha (not as intense as what I was thinking but still), but the best part I would say was when we pulled out and out came his cum it was so warm and it was great, I unfortunately didn't finish but I don't mind haha.

I also forgot to mention that he is in an open relationship so his partner was home the whole time so we had to stay a little quiet haha. Also he was in his late 40s and I'm 20 for those who r curious, he is also a bear 😉.

But yeah that is my update thanks for reading and if u have any more questions feel free to ask 😋

So to start off I’m straight and I like women, it started when I was on the buss I’ve been really horny for awhile so I easily get hard fast so I get on this buss and sit down next to this guy and we talk because we both came from the same area I won’t say but when the talking keeps going all of a sudden he sees me being semi hard and decides to just go and touch it without any warning or saying anything and when he touches me I just froze and he began to feel it up and it got harder to where I thought that was going to be it then then he stops touching it and here I thought it’s over but instead he lifts my sweatpants up and looks at it I was shocked and said no don’t and then he put his other hand in there and grabbed me instead of me stopping him I just froze again and when he started to feel it I got so hard and her started to jerk me off I tried to say no don’t but it felt so good I couldn’t resist it
I take dms

Found a guy on Grindr that was pretty cool, talked for a few and decided fck it let’s do it.

He was similar ish to his profile, not really my type tbh but he had a big dick. Anyways, he came over I’m already super awkward, especially this being my first time, he was pretty awkward himself but he was rearing to go. Initially I told him I wanted to top and he was cool with it, but I was too nervous to get it up and let him top instead he seemed happy with the idea. He gave me a blowjob leading up to it I still didn’t get hard but it felt good. After a bit of that I turned over and let him top me in doggy. Initial penetration was amazing, no dildo can match body warmth and especially when someone is excited to go, I really enjoyed it I was moaning and stuff and I could tell he was enjoying it.

After about 10-15min of pen he came inside me (with a condom ofc), I could feel him cumming which was a weird sensation but I enjoyed it. Things ended pretty quick after that, PNC and all that, I never got off but I didn’t really expect to tbh. I still had fun and glad the initial hookup stage is over :p He was super sweet all the way through and really appreciated that.

Also tried to give him a blowjob only lasted about 5 min and was too self conscious to keep going that was also my first time doing that to another guy.

Soooo I only came out to myself I guess over the last few years, always had a feeling I liked guys too (honestly more any gender or not at all really so maybe more pan) but kind of more certain on it over the last few years.
Anyway, I’m yet to get my first time with a guy (I’m Dublin based and it’s super hard to get a decent or “normal guy” I’ve noticed) but I want to so badly
Completely vers but definitely wanna bottom first to finally see what everyone’s been talking about 😏
Not really a first time story I guess, just really want to do you know if anyone’s in Dublin…..

Wanted to share you that short story. I can't really share that with my friends because I think that they would be to surprised or maybe that's just to much information for them but I have to tell someone. I'm 30 yo.

I was always into girls and had several realtionships but discovered over I time I like the pleasure of analsex, but not only with strap on (we tried that) but with men.

After broken up with my last girlfriend I knew that I need to get fucked by a men and that I'm really a bottom. It was so hard for me to make that step to meet someone because I'm very shy and I was scared by Grindr or Romeo hook ups things, it seemed to me that only for perverts or so and dubious people :D but today I was a little bit more brave and I really made a date. He opened the door for me and already layed naked on the bed, and the light was very low to make thinks easyer for me. I layed to him but sad that I'm very nervous but he was so understandable and accomodating , he sayd slow down, don't make things you don't want to to but tell me what you want to do :) just feel good. I gave him a few minutes a blowjob and he very liked it and said I'm doing very great for someone that never did it and then, finally I said I want to get fucked know. By the way I was wearing a chastity cage on my own idea, he liked the idea. He fucked me in doggystlye now. Maybe alitte to harsh at the beginning :D I'm used to big dildos etc but that was just to fast and not enough lube, I asked to slow down to him but he kept going because he was already almost finished and then he shot his load in my ass (with condom). After that I left quite fast because it was already so late It was a very short experience in general but I'm so glad that I finally had my first time with a guy and we decided to meet again, tomorrow, and he said tomorrow we will have a longer session. What a great experience :)

The sex was not mind-blowing honestly because it was so short honestly and I needed to adjust my blowing skills a little bit but I feel relieved somewhat, just because I was brave enough today to do it :D I think that's maybe the beginning of a new sexual life for me. I think in the future I will not be so scared anymore.

Me and my cousin used to take baths together. It was very normal for us to take baths. This one time we were in a bubble bath at my aunts house me and my cousin were sat facing each other naked in the bath.
I move around and accidentally kick him in the penis/balls. I say “omg I’m so sorry”. He gets up to check if they are okay. They seemed fine but then he says “kiss them”. I’ve always wanted to touch someone else’s cock. So I moved over towards his cock and balls and kiss the tip of his dick. He said “that felt good but you forgot my balls.” So I went in for another kiss. But this time I kissed his but and licked them.
I end up standing up too. So there we are both standing facing each other with our cocks getting harder and harder. Even though he was younger than me his dick was bigger than mine. We grab eachothers cocks and start jerking each other off. We get scared and don’t want to get caught so we sit back down in the tub and jerk each other under the bubbles.
Then he asks if I want to suck it. I didn’t even say anything, he knew to just stand up and I started sucking right away. He ended up not lasting too long and not telling me that he was cumming. So his first shot of cum surprised me and I pulled away and the rest of his load went all over my face.
Then he sat back down and he kept jerking me off till I came all in the tub. After I finished cumming i see that his cock is poking out of the bubble and he’s hard again so I say “you want to go one more time?” He says “yes but this time let’s try your butthole”.
So I bent over in doggy style in the bath and he was on his knees. My aunt has this bottle of baby oil on the counter so we used that as lube because his spit wasn’t working. He starts fingering my ass to get me loose. He finally is able to fit 3 fingers in comfortably so he runs baby oil on his cock and puts his tip in my hole and slowly goes in. It took a minute but after he finally got all the way in I told him to start thrusting slowly. So after a while of him thrusting slowing he starts to go faster and faster. And after about a minute of him pounding my ass fast he cums inside me.
After that we ended up getting out of the tub and dry off. We go to his room to change and when I drop my towel and start to grab my clothes I feel something wet go down my leg and I look at it and it’s cum dripping down my leg. I told him to look and he said “my cum is seeping out of your butthole”. And he also said “your hole is still open and loose”.
That was one of my first gay experiences with my cousin and first of many. One of my favorites too.

Hey I am 23 M bi. This is a true story and it happened when I was 18. I was still considering myself str8 and had only been with women. I always have been fit and jacked. I workout 5-6 times a week and do boxing as well. I always had curious thoughts in the back of my mind about masc men and dominating them. One day I went downtown for shopping and while shopping I came across a book store called "Indigo". I like reading so i went to look for some books. I kept walking around and reading random books and suddenly I had to pee really bad . I went to the washroom to relieve myself. There were three urinals and they were not covered at all. The ones on the both sides were occupied so I went in the middle one. Deep down i was hoping to see some nice cock. I started peeing and mid pee i felt the guy next to me look at me and move his arm. I look at his side and i saw he wasnt peeing yet he was playing with himself. It made me erect and i stopped peeing. Then they both started stroking their dicks. Im uncut and they both were cut. I have a decent length but they definitely had more girth . It made me very horny and idk why that kinda made me panic and i quickly just put my hard cock away and tried to go out. I went close to the enterance door it was hidden from the urinals. I calmed down and walked out. However the thought of jerking off with other guys kept playing in my mind. I couldn't resist and gave in. I went back and all the urinals were now taken. I saw they all were stroking. They saw me watching and put a nice show for me. I went close and just pulled my cock out. We all started jerk eo off. The door was far away and was loud when it opens. The entrance had no vision of the urinals either. It was enough time to put our cocks away and not get in trouble. We kept jerking eo off for a while. One of the guys looked at me and gave me a look asking if he can blow me. He was a bit older and was definitely married. I saw a ring in his finger. Being a horny teen i caved in and he gave me the best blowjob ever. I came in few seconds and he swallowed it all. It was a starting of my curious journey. I went there a lot of times and had a lot more experiences.

25M, Title is pretty obvious, I got a small 4.6 inch silicone dildo and some water based lube. I was hesitant at first but once I used my finger I knew I wanted it bad, so I lubed it up and put it in and it was weird at first but once I started going it felt so good I couldn’t stop and came all over myself. I’ve only felt myself to be bi but after using this toy a couple times I just want to be taken by a man more and more.

Ok so basically if you go on my profile I post a lot haha but I've never had sex. However for as long as I have been posting I've been always looking around on grindr and sniffies trying to build up my confidence.

Finally after being locked for a bit I finally bit the bullet and asked a guy I had been on and off with to do it, and well it's happening tomorrow.

The plan is to grab lunch then head to his place, he is a much older gentleman than me but that's what I wanted (experienced). So yeah I'm super nervous but also so excited.

But now that I'm actually committed I'm not too sure how to prepare. Should I be cleaning myself before I get there or at his place, what should I bring?

Basically I would love to hear any advice. And happy to chat if you have any questions too 🫣

I'm also wanting to ask to take pics and vids too so look forward to that maybe haha.

This is a long story so I may have to tell it in multiple parts.

By the time I was about 19, in my second year of university, I knew I was, at least, bisexual. I had a girlfriend and was straight acting, but ever since I had stumbled on some gay erotica in my teens I had been secretly fantasising about men. I can still remember the rush I got the first time I read a gay story, about a cross-dresser who gets caught by his neighbour. He ends up getting fucked by the neighbour up against the clothesline while he's hanging out the washing wearing a lacy camisole. While I may have been straight during the day, at night under the covers I was jerking off to fantasies about men almost every night. It was like being two different people. At the time I used to drive past an antique shop on my way to and from campus. I was into vintage clothes and that sort've thing, and was desperate to seem cultured and cool, so one afternoon after classes I pulled in on my way home. I can't remember a lot about the store, but I remember it was a large, typically rambling antique store with lots of nooks and crannies. I also remember it was empty when I went in. As I was browsing, the guy who owned the shop started chatting to me from his desk. He was an older guy, probably in his mid 50s, taller than me, with a thick moustache and a bit of a paunch but in pretty good shape. Today we'd call it a dad-bod. Eventually he walked over to where I was looking at some old paintings and started talking to me about them. He started asking me questions about myself; just about what I was studying, things like that. We talked like this for a few minutes. He was obviously gay. His voice and mannerisms screamed camp, and the way he talked about the art we were looking at made it obvious he was cultured. I liked him. As we chatted, he mentioned what I was wearing - a pair of shortish denim shorts which hugged my thighs - and said something like "I have to tell you, I love your legs". I just sort've laughed it off and said thanks, but was too taken aback to say anything else. He kept going though, and said: "you must get a lot of attention with those legs, from girls... and guys." That last part was added almost as a question. I was totally flustered. I could obviously feel that he was hitting on me, and although I had fantasised about it a lot, I had never been flirted with by a man before. Picking up on my nervousness, he asked me, in a fairly light way: "I suppose you're straight?". I remember hesitating. Part of me wanted to say "NO, I'm actually desperate for cock, I jerk myself stupid every night thinking about it", but my nerves got the better of me. I think I muttered yes, said something about having a girlfriend, and made a hasty retreat. I was in a daze after it happened. For days, I couldn't stop thinking about the feeling of being openly pursued by this older man who clearly wanted me. In my late-night fantasies, I was always the bottom, the one on my knees or bending over, and having this man, old enough to be my father, objectify me like that sent me into a spiral of horniness that I couldn't shake. After about a week, I made up my mind that I would go back. I wasn't even sure what I thought would happen, but I made sure to wear the same pair of shorts. I was a pretty slim guy, something I was usually self-conscious about, but I also decided to wear a fairly tight, short white t-shirt which only barely covered my midriff. I was disappointed when I got there, though. This time the store was busy, and the owner was busy helping customers. I waited around for a bit, trying to act like I was looking at the stuff in the shop but really just hoping he'd notice me. After a few minutes, he did. I felt him notice my presence, and looked at him. He gave me the briefest smile, which I shyly returned. He looked over at me a couple more times before finally excusing himself and walking over. In a voice loud enough that the customers he was helping he could hear, he told me in a polite voice that he was tied up but if I came back a bit closer to closing time, he could help me with the purchases I was hoping to make. I can't remember exactly what it was - some furniture, maybe - but it was definitely a totally made up pretense. He was inviting me into a secret rendezvous. If I said I didn't know what he was talking about, he could say he had mistaken me for someone else. If I agreed, I was accepting his invite. I can still remember my heart beating in my chest as I said, my voice a little raised, that that sounded perfect. My cock was as hard as a rock as I left the store and got back into my car. I can't remember exactly how I killed the time. I think I drove somewhere and just sat in my car waiting. I kept telling myself I should forget the whole thing and just go home, but my horniness kept me there. Finally, about 15 minutes before closing time, I pulled up back at the store, took a few deep breaths and walked in. He was still serving a final customer when I arrived, and again I loitered around trying to pretend I was browsing. I remember watching as he walked out with the customer, locking the door behind him as he turned to me after they were gone. "You came back!" he said cheerily. Even though it was clear why I was there, he was keeping it light, which I appreciated. He told me his name, Rick, and I told him mine. We chatted again, this time about music because I had been inspecting some old LPs. I started to relax. "I'm sorry if I offended you the other day," he said eventually. I told him no, I just hadn't known what to say. He said something about remembering how difficult it was being my age. Eventually, he told me he had some more records from his private collection upstairs in his office if I wanted to look? I said yes, and he told me to follow him. He let me start climbing the narrow staircase first, and I still remember him making an audible grunt of approval as he walked up behind me, his face level with my ass. When we got into his cramped office I was somewhat disappointed to see he hadn't been lying. There was a big collection of LPs, some stacked, some displayed on a shelf. For a while we stood there looking at them. I felt frozen. My nerves, which had dissipated, were returning, but this time because I didn't know how or whether to make the first move. I need not have worried. All of a sudden, I felt his hand rubbing my ass. "You look so good in those shorts," he said, his eyes on me. Still looking straight ahead, I let out a little moan as I felt his fingers caressing my crack. "I got that impression, that's why I wore them again," I offered. And that was it, suddenly he was on me, pulling me to him, pushing his tongue into my mouth, and I was making out with a man. I remember thinking how surreal it was, but also how normal it was. Gay kissing was a lot like straight kissing! His hands were on my body and underneath my shirt, playing with my nipples, and I was doing the same, feeling his bigness and heft and swooning at the feeling of being taken by this big man. I felt like a girl and loved it. I could feel his hard cock against me as we pressed our bodies together and I started to grab at it, squeezing and pulling on it, he started guiding me down and I happily fell to my knees, undoing his pants and pulling them down to reveal his cock. It was fairly average sized, but bigger than mine and much thicker. I started to suck him off, not really knowing what I was doing but just basically copying what I'd seen in all the gay and straight porn I'd been watching. He was groaning, holding onto my head and pushing it down on him, subetly at first, before eventually he was fucking my mouth. I remember feeling turned on beyond belief that my mouth was being used by this old man. After maybe 10 minutes of this, he pulled his cock out of my mouth and pulled me to my feet. He'd stripped off his shirt and started kissing me as he pulled off mine, then undid the shorts that started all of this and let them fall to the ground. In just my briefs, he told me to turn around and lean against the desk. I did what he said, sticking my ass out, but in truth I was suddenly terrified. I had experimented a bit by myself, using fingers and a toy I'd bought in secret, but I wasn't sure if I was ready to get fucked in this cramped, cluttered office. Instead, he did something I had not been expecting at all, yanking down my briefs, falling to his knees behind me, and burying his tongue in my ass. Having my ass eaten for the first time was a feeling I can't really describe. I'm honestly not sure anything as hot has ever happened to me since. I remember letting out a big, high pitched moan as waves of pleasure washed over me. The sensations, where no one had ever touched me, were intense. It felt so hot and naughty. Until that point my own cock had been going hard and then soft, my erection tempered by the nerves I was still feeling. But as I pushed my ass back onto his moustachioed face, moaning and whimpering, i was suddenly hard as a rock again, and couldn't stop from jerking myself. All too soon though he stopped and stood, leaning forward and kissing my neck and asking breathily if I wanted to fuck. I was weak limbed and glowing from the rimming I'd recieved and just said "yes please". He walked into a small bathroom, leaving me leaning against the desk catching my breath, and after a minute came back out, this time with a condom and a tube of lubricant. "Always be prepared," he said laughing as he showed me the lube. I exhaled nervously and he said "I assume this is your first time?" I just nodded. He told me not to worry, that he'd guide me through it. I won't go over the whole thing, but it took some time. At one point, when it felt too painful, I told him maybe I wasn't ready, but he kept telling me to relax, that I needed to breathe. To be honest, looking back, he was quite insistent. Now that I'm older, and know more about consent, I would not condone the same behaviour. But to be honest, I loved it, and still love the memory of it. This pervy older man had unlocked something submissive in me. Finally, after what felt like an eternity, the head of his thick cock was inside me, stretching me out. It hurt, but in a good way. After leaving it like that for a moment to get used to it he slowly pushed further and further inside me, until he was about half way in. Slowly at first he started to fuck me, pushing further and further in each time until I could feel him bottoming out inside me. I was crying out in pain and ecstasy, letting him have his way with me. My own cock had shrunk, a little nub sticking out as he took my cherry. As he sped up he started talking dirty to me, telling me he knew a guy with a face as pretty as mine couldn't be straight, telling me he could tell I wanted it when he first cracked onto me. All I could do was moan as he had his way with me, shouting "yes, yes, yes". After maybe 15 minutes, just when the pain was starting to overwhelm the pleasure, he started to get wilder, pushing into me hard as he spanked my ass. All of a sudden he let out a guttural yell and I felt him pulsing as he emptied his balls into the condom. He collapsed on top of me, both of us sweaty messes lying on his desk. Me face down, him with his body pressed against me. After a while he got up and kissed me again. I sat on his desk and wrapped my legs around his body while we made out. He offered to go down on me, but I was too frazzled by everything, I knew there was no way I could get it up. We both got dressed and walked downstairs together. Outside the sun had set, and as he opened the door for me we exchanged one last furtive kiss and I was out the door and back into my car, my head spinning and my ass stinging. That was the first time, but it wasn't the last.

I write a decent amount of fictional gay sex stories on this app, but I've never written about my first time. Well, I guess, both first times. I have my first gay hook up as a top and I have my first gay up as a bottom. It happened in that order, so I'll talk about my complete first time with another guy as a "straight" guy who got seduced into not being so straight.

At the time, in the early 2000s, I was a 21 year old college student living in New York City. I played hockey, had an athletic build, clean shaven, and spiked dark hair. I was also on a cold streak with women. So I put on a nice button up shirt, blue jeans, and expensive looking knock off dress shoes to go to one of the nearby popular clubs.

I was terrible at everything in the club. I wasn't comfortable dancing and talking to women was just not working out in such a loud setting. As I made my way through the dance floor over to the bar, a petite feminine person with long wavy dirty blonde hair, who I thought at the time was a woman, playfully grabbed my crotch and continued on their way. I thought to myself that maybe my luck was changing, but I couldn't find the "girl" that did that and just continued to the bar to get my drink.

I had a couple of drinks in the bar area, struck up conversations with some of the women my age that were there, but I was definitely striking out. I figured I was either really out of practice or maybe this just wasn't my scene anymore, if it ever was. Then the petite "girl" with the wavy long hair randomly reappeared and started grinding against me before turning around, playfully grabbing my crotch, and asking me if we should get a cab and take this elsewhere.

Horny and not noticing the clear signs that this sexually aggressive woman was actually a femme male, I agreed and grabbed a cab to go back to her place.

On the cab ride to "her" apartment I kept trying to slide my hand up between "her" legs while we were making out, but was stopped by their hands. They then reached into my pants, stroking my cock, and then pulling it out to suck it, not caring if the cabbie saw us or not. Stopping me from even attempting anything else as I enjoyed the cab ride blowjob.

We got to "her" apartment, I paid and tipped the cabbie, and with my hard cock stuffed back into my pants I entered the apartment. We drunkenly made out and grabbed each other and as I tried to reach between their legs again, they pushed me back onto the couch, pulled down my pants, and started sucking my cock again. I ran my hands through their hair as they sucked and moaned softly telling them what a good cock sucker they were. They must have noticed O was almost at the brink of blowing my load when they pulled off my cock and said we should take this to the bedroom.

We got to the bedroom and started making out again as they quickly stripped me naked. I started returning the favor and as I started taking off their tight jeans, I felt his bulge for the first time. I paused as I slowly moved my hand back, but he quickly grabbed my hard cock and started stroking it, asking me in a flirtatious manner that I'm not going to back out now, am I? Maybe it was the drinks or maybe it was the horniness, but I went with it, told him I wasn't backing out, and we made out deeply as I pulled the rest of his clothes off.

We rolled around on the bed making out as he grabbed my cock and I squeezed his smooth ass. He then rolled over, pulled a condom out of his bedside drawer, ripped it open, and slipped it onto my cock. He got on his hands and knees, reached back to help guide my cock to his hole, and pushed back as I pushed my cock into his tightness. He kept the pace at first, but then I started taking control and started fucking his ass hard and deep. I gripped his hips as I hit his hot ass from behind as he moaned loudly, telling me to fuck his ass like a pussy. He then said he wanted to ride my dick, so I pulled out and got on my back.

He leaned onto me to give me a deep kiss before grabbing my cock and positioning it so he could slide down it with his ass. With my knees up he bounced up and down on my cock, moaning loudly with each bounce. Suddenly he let out an even louder moan as he shot his load onto me as he continued to bounce on my cock. He could tell that caused me to almost shoot my load myself, got off my cock, pulled off the condom and started stroking and sucking my cock. He told me that he wanted to swallow me as he went back to sucking and stroking and almost on command I shot my load down his throat. With both of us satisfied, he crawled up next to me to make out some more. He excused himself to wash up in the bathroom and I passed out drunk on his bed.

The next morning, I woke up to him walking around naked and cleaning up some of the mess we made the previous night. He told me good morning and sat down next to me and told me how good the fuck was and asked if that was my first time with a guy. I told him it was and he jokingly told me not to worry. That it was our little secret. I agreed and admitted I enjoyed it quite a bit. I then got up, used the bathroom, washed up a bit, and started getting dressed. Still naked, he sat on my lap and asked me if I wanted to exchange phone numbers. We did and as I gave him mine, he playfully rubbed his bare ass against my now clothed crotch. Then he got up, turned around, and told me not to be a stranger. He walked me to the door where we made out again, him grabbing my crotch and me grabbing his ass, and I made my way to the subway station. When I got to my stop, my phone went off and it was a text message from him thanking me for being such a giving guest. When I got to my apartment, my roommate asked where I was coming from and I told him about the hot girl I hooked up with from the club as young and stupid straight guys do.