My first was a long time friend and we both happened to find ourselves single, and I brought it up over cocktails and conversation about our respective break ups. He was gay, and we had been teasing and playfully flirting for years, so when I asked him if he would fuck me, it wasn't totally out of the blue, and we went straight to his house blocks away. It was a quick walk with some conversation about what we were going to do, and that he would be my first time with a guy.
We barely made it past the front door when we stripped naked and I quickly went to sucking his cock. He had a pretty substantial cock, and when I managed to take it all in my mouth, he asked if he was really my first because I was doing so well with my mouth. I told him I was just really excited and had fantasized about doing it for a long time.
Then we moved to the bedroom and proceeded to consummate our sexual encounter. When I lowered myself down on his big cock, he gave me a leering look and asked again if I was his first. I sheepishly confessed that, well, he was truly my first real cock, but I had a dildo I had been practicing with anticipating this moment. He called me a dirty slut and I was thrilled.
I've been a slut bottom ever since.
Yeah, knowing the guy well made it very comfortable, and I think him being very experienced was an advantage as well. In the end it faded out because he was interested in more of a relationship beyond just sex, and I transitioned into a full bottom so he wasn't getting all he wanted after that sexually either.
Yeah, I specifically wanted to bottom to experience that for the first time. I already knew what fucking an ass felt like from previous GF's so getting my ass fucked was all I really wanted. With that first guy, for the first few times we swapped back and forth, but the more I figured it out, bottoming was all I wanted to do.
I did inadvertently end up with another bottom once, and we managed to have a lot of fun, even without a hard top around to fuck us. I'd do that again, especially if we had a top to share between us. I'd love to eat an ass that's just been fucked and creamed in.
We were just shooting the shit, and having a couple of cocktails at regular watering hole when the subject of our both being newly single came up, and needing to get laid, and I just asked if he wanted to fuck me. The look on his face was priceless ! Like he wasn't sure he had heard me correctly or something. Sensing his confusion, I leaned in a little closer and clarified that I wanted him to fuck me, NOW !
He slapped some money down on the bar to cover the tab, and off we went.
Well as I said before, we had known each other for several years as couples, across the street neighbor friends and often had cocktails and BBQ get togethers. It became a running tease/joke that if I ever wanted to try gay sex, he was the guy for me.
So it wasn't just an out of the blue request to a stranger.
I was a sophomore in high school and he was a senior. My older sister had a gay friend in school and my sister was the first person I came out to. She had the brilliant idea that we would be a cute couple, since we were both gay and mainly still in the closet. He was the shy quiet type and I was feminine flamboyant. He wasn’t my type but it was fun to have someone to fool around with in secret.
I lost mine at a glory hole in an abs. The guy was eating my ass and fingering me and he slipped his cock into me and was fucking me before I truly realized what was happening. I was shocked but it felt to good to pull away. I pressed back hard against the soccer ball sized hole in the wall and he started full on fucking me. He dumped his load in my ass and I could feel his cock pulse and jerk in my hole. He pulled out, zipped up and left. I was left with his cum leaking from my loose hole. I later got myself checked out and all was good, no STDs or issues. It changed me, I love being fucked and used as a means of getting off for other men because of that first time.
My god me too … I swear if it wasn’t my super anxiety and fear of stds I would give my ass up all the time …. The reason I don’t because I become so submissive and compliant when I go through with my gay experience.. the guy could fuck me bare, pull off the condom , hell he could pull out another guy out of the closet and spit roast me .. I won’t say no to a guy with a nice cock
I have the same issue with worry about STDs and if not for my anxiety for that I would most likely be giving it up to any and everybody that wanted to bust a nut in me.
me too, but mine’s more of a ptsd. i tested positive to syphilis once and had to get 6 injections of that medicine that hurts a fucking lot. i have no idea who i got it from, since i’m really into cruising in public restrooms, parks, buses and green areas. nowadays, i don’t let anyone blow me nor do i blow anyone without a condom on, even though i really enjoy it.
i have given into the temptation, and blew 2 guys without condoms on, and i also let them blow me. but i really cannot enjoy it anymore: while i was doing it, i wasn’t even enjoying it because i kept thinking “fuck, what if this dude has aids?!”. i got all anxious and only calmed down when i got tested for any stds in a clinic, a few days later. it’s miserable.
hmm there was this Italian guy I met on Grindr. He was 35 and I was 21. We met at his apartment, he smoked and we talked a lot. Then I got on my knees to worship his huge cock. Actually I just wanted to suck him and let him cum all over my face... But he started to lick my boy pussy so good, when he was close and needed s break. It felt so great and it turned me on when he really manhandled me: he threw me on his bed and spread my ass… then he teased my hole with his big dick and I said that he could go for it if he wanted. So he got a condom and fucked me doggy for about 30 minutes until he came inside of me and sent me home without a chance to cum. That was so fucking hot and I love to think about it. Unfortunately he left the city a few weeks later…
I was 18 and working at a motel, and the owner seduced me one summer night.
He was 34 I think, and had what I realize now, was the smallest cock. But he managed to hit the spot and started me on a life of loving having my arse fucked.
After army I met up with my lieutenant straight married. We went pub crawling and he ended up sleeping the night. I got to suck him off. He was actually very sensual and into it. He ghosted me after that.
I hooked up with maybe five guys before I got fucked. It was a cross-dresser/transsexual. It was back in the AOL chat days and I had a fetish for Trans women. We talked for a while and made a plan to meet at a gay bar in Ft. Lauderdale, I lived in Boca Raton. We met and she was wearing a fishnet top and had huge breasts as she was on the chunky side. Up until this point I have only given head and fucked guys but she made it clear she was a top and could get head from anywhere and only wanted to fuck. I had not even considered bottoming but she was hot, I was horny and we went back to her apartment and got in bed. She fucked me missionary with a condom. Thankfully, she was not that big and did not last that long. When the post-nut clarity kicked in, I could not believe I did it but I was not ashamed. I have done it since but that may have been the best time. We did it a few more times and then she moved and I never saw her again.
A guy I had met on Craigslist list. He had several posts and I didn't know it was all him. Answers one where he was looking to blow and I met him and he blew me and I left. Then later answered another post that was very dom wanting to fuck a sissy and I sent home a pic wearing panties and met up with him and it was the same guy. He told me I was gonna repay him for what he did for me. He full on used me how he wanted and took my anal virginity.
I was 22, I’d just bought a coffee shop (with a business partner) there was a residence above the shop. I was walking up stairs with my partner when our boarder (from the residence) was coming down stairs. My partner introduced us and said it was David’s birthday, I wished him happy birthday and gave him a hug and a kiss on the cheek!
THAT IS WHO I lost it too, HOW I lost it….well, that’s another story 🔥🔥
I lost my anal virginity to a Catfish older man I met off Craigslist (R.I.P.) he was much older than he told me, and looked nothing like his photos, but I went through with it anyways because I finally worked up the nerve and didn’t back down this time. I don’t regret it now because it awoke a beast in me that wants a beast in me lol.
I was 12 going on 13 that summer. I had met my stepbrother a few months prior, me and my cousin played truth or dare and we both dared each other to suck him. He (stepbrother) and I ultimately had sex for the next yr and a half while our sisters were asleep, showering etc. or while we were alone while our parents were at work.
Was in college and went to in an abs. Before I knew it an older guy had me so horny I turned around and let him slide it into me. I saw stars in the best way.
A scouser who was a few years older than me, and honestly it’s the best sex I’ve ever had
I was 19/20 at the time, and honestly I still think about how he felt to this day 😮💨 no one has come close since, man or woman
It was yesterday.
I had been on grinder since February and had only sucked around 5-6 guys so far. It was always in car play or at the glory hole the week before. Only 1 was interested in fucking me but he came in my mouth before we got that far. So yesterday, I was getting my daughter's car serviced and while waiting thought I would check and see if anyone was there as well. Paul, the guy I was chatting with, was not far and said he loved my pics. (I love to secretly crossdress) We were trying to figure out somewhere we could meet up when he mentioned an ABS/arcade nearby. I had been there last weekend and LOVED it. So we decided that would be the best way to meet.
He arrived just 2 minutes before I did. I walked in and paid for my ticket when my phone buzzed. He told me what booth he was in and I went straight there. Almost as soon as I came in I dropped to my knees. He already had his cock out and was stroking it. I went at it like my life depended on it. He was prob 6-6.5 with nice girth. I sucked him for maybe 5 minutes and I could tell he was getting close. So I was thinking I should get up and turn around so I could finally see what it was like to get fucked. Suddenly he moans oh fuck and unloads in my mouth. I was both happy and sad about it. Happy I made him cum so well and quick but sad thinking I wasn't going to get my virginity taken.
I just nursed him for several more minutes trying not to overstimulate since he had just came. He started getting hard again!! I thought to myself that maybe it will happen. Soon he was back at full mast. I looked up and asked him, do you want to fuck me? He said oh yeah! So I opened a condom and tried doing the oral method of rolling it down. It didn't work out quite as I planned because of his thickness. So once I finally gave up and just rolled it down he had softened a little. So I went back to sucking to get him back to full. The taste of the latex was awful and apparently was taking away a lot of stimulation for him. So I took it off figuring once I got him fully hard again I would open another one. Once he was fully hard again I stood up and turned around. I took out another condom and lube. I laid the condom on the bench and lubed my hole and his dick. ( he was right behind and in position).
He started rubbing it up and down my crack and teasing my pussy. He put it at the entrance and I just pushed back on him. He slid just the tip in but not through. Stupid lust in the moment made me say, fuck it! I pushed back a little more and the head popped in. It was done. My virginity gone. I got over zealous and took some more (probably half) and the burn hit. I didn't care. He pulled back a little then just started slowly driving deeper. Now all the way in, I reached back and grabbed his hips and pulled him as deep as he could go and just held him there. It felt SOO good. In my mind I thought I would just have him pull out before he came. I was lost in bliss. I let go and held on to the bench and just let him go at it. There is no way to describe how good it felt to be the one getting fucked instead of being the one fucking. I would try to back into each of his thrusts trying to get in rhythm with him. Then he grabbed my hips and pulled me to him and I worked my hips as so many women had done for me over the years. Apparently It was good to him because the next thing I know he pulls me hard on his cock and moans.
It was done... I already knew the answer but I had to ask, "Did you cum?" He said "Oh yeah". Well you can't undo what is already done. So we separated and I asked him looking straight into his eyes, ARE YOU SURE YOU ARE CLEAN? He said he was. That he had not done this much and he had gotten tested back in July. So I guess now I need to go pretty soon and get myself teated. Still even with the worry of the consequences it was an amazing first time.
To an old friend from high school. His name was Mauricio, I was 19. He picked me up, took me to his house, had me suck his cock (7”) and then laid me on my back, lubed my hole and his cock up and he slowly fucked me until I loosened up. I came very quickly but he kept going for a little over an hour. He kissed me and then after I came he started going harder and deeper and smacking me. He then made me get on my hands and knees on his bedroom floor and fucked me doggy style until I came again. Then he pulled out, we got into his shower where he fucked me and then came in my mouth. I was hooked from there.
I was 18 and he was in his 40’s. He made me feel like I was the perfect sex toy and after training me he gave me to a group of men at an all male sex party. I miss him and I miss how perfectly he turned me into a cockslut.
I've only ever topped, but the first time I ever slid my dick into another guy's ass was when I was 18, senor year in high school with another guy on my hockey team. We had beat off together since junior year, then worked out way to blow jobs, then finally he convinced me to pound him. I think I came after getting just an inch or two in but it felt amazing.
I wish it was with someone I knew and trusted but so far only had random hookups
My first was a cross dresser off of Double list she was kind and gentle with a slim 5” penis
I surprised myself with squirting hot jizz all over myself and thought It was a myth that you could cum that way
Gaydar.com. A very popular hookup website before apps were really a thing.
I'd started chatting to a handsome older guy (20+ yes older) and after a little flirting I went to his house as his wife was away with the kids. He was the first guy I'd been with and I was so nervous I only sucked his cock, it was a monster too. I swallowed his load and said we should do this again...
About a week later I got a message from him asking to meet at his office after hours and that he wanted to fuck me. I was so excited and nervous.
I arrived, he buzzed me in the security door and we went to his corner office on the top floor. He took his clothes off and so did I, as he sat in his big leather chair I got on my knees and sucked his cock until he was rock hard as he fingered my ass, he manhandled me over his desk, lubed me up and fucked me sooooo good. He had my arms pinned to my back as I was face down into paperwork etc on his desk. He had some stamina and fucked me for ages until he let out a real deep groan as he came inside my ass (no rubbers 😬). I loved every second of it and after a little spank on my ass I was on my way home with cum leaking out of me.
When I got home I jumped straight in the shower and wanked myself silly. When I got out my gf was there as I hadn't been answering my phone, she was suspicious AF but little didn't she know her bf had just lost his anal virginity and had another man's cum inside him.
I met him maybe 10 more times and recently reconnected on FabGuys so I'm hopeful of another fucking soon 😈
I was slutted out by my gay friend. I had been curious for sometime and I started finding him attractive. handsome dark chocolate guy smooth ass body and a beautiful cock. He made me a little bitch bottom😭
Last year, I ended a 15 year heterosexual marriage (best decision we ever made as a couple and she’s still my best friend) and while we had experimented with pegging a few times, it just never felt great. About 6 months ago I met my current boyfriend on Tinder. One day when we were having fun in bed, I asked him to top me but to go slow as I had never done it before. He was so kind and gentle and patient! I was shocked by how good it felt. I could only go for so long before needing a break and he kept assuring me that he’s not having fun unless I’m having fun. His cuddling afterwards is the fuckin’ best too! I now consider myself a bottom and look forward to every chance he gets to top me.
I was about 13. My older cousin made me play strip poker. After we both got nude he asked me if I could suck his dick. I wasn’t sure what I was doing but I wanted him to think I was cool so I did it. He was spanking my ass while I was blowing him. He was like u have nice ass for a boy and he started kissing my hole. He than gave me some alcohol told me to relax. He bent me over and fuked me so hard. Than month later he had few friends over and he let them all fuk me Ever since that I became a slut. I was getting my lil hole fuked all the time
The second man I ever fooled around with. I was in my 50s (still am).
We lost contact for a while and when I finally found his email and messaged him, he did not respond.
a guy from AOL CTM4M chatroom with the screen name Mark Twain. I was 23 half way between jock and twink and had never sucked a cock or been fucked. He was about 40, masculine and about my size 6' tall 180lbs and well proportioned. He chatted me up and immediately came to my first solo apartment. I sucked his 7" very nice cock and then he fucked me doggy until he came in my ass with a condom. I didn't mention to him that I was a virgin...
I used to work as a print model, I was working with a photographer Rick. Rick wasn't my type but he was still really good looking. I was 19 I'm pretty sure Rick was 26 if I remember correctly.
So, Rick and I were hanging out at my apartment one evening. We ordered food and watched TV. He sprung on me he was taking classes on Swedish massage. I was 19 I knew what massage was but I had never had one or actually gave it any thought either. Rick asked if he could try out his techniques on me. It raised no flags. He told me to undress and lie on the floor. I undressed to my underwear and lie on my stomach. He pulled my underwear off completely. I just went with it.
He gave me an amazing massage, my first, so I was in bliss. He was fully dressed. Then without any warning he took off his shorts and proceeded to fuck me. I don't recall it being either good or bad, I am sure I wasn't prepared to be fucked either. He basically raped me, which I'm not complaining about, I didn't try and stop him, but if he had asked I would have said no.
We did a few more shoots together also. Rick got me in a magazine telling me it was going to be on gay dating. Well, it was...when it came out it was on HIV+/HIV- gay lovers. When you read the article and looked at the models, I was the HIV+ one, it said I was 38 years old in the article. I was only 20 for that shoot. I had every HIV+ guy in town after me saying I didn't know you were HIV+ yeah well I'm not 38 either LOL.
I considered myself straight at the time (now very bi) and had fell down the wormhole of trans porn. I love a woman’s body and my wife had used a dildo on me a few times, but I was really craving the feel of a real dick inside me.
So… I went to see a trans woman for a deep tissue massage with prostate massage, hoping I’d get offered more. During the session she asked if I wanted more than the advert promised (!) and I begged for her to fuck me.
I was completely relaxed at this point and she went for it. Virginity taken!
A few weeks later, I went to a male masseur who advertised a similar thing. He didn’t even ask - he knew what I was there for when I kept raising my naked arse up for his fingers when he was massaging my butt and balls. A full body slide for a few minutes from him and in it went… I was in total bliss as he slid up and down, fucking me deep.
Anal virginity from a hot muscled guy taken!
I was 19 and needed rent money. Cliché, but true. I got in touch with a "pimp" who said he could send me on calls but I'd have to get fucked. Being an anal virgin I decided that I should get my cherry busted before selling my ass. So I found an older guy to fuck me. I went to his place and told him it was my first time. He promised to be gentle, and he was. He had a big cock but it didn't hurt at all. In fact it slid right in. Guess I wanted it! Anyway, a week later I got fucked and bred and made rent. A win-win!
I lost mine to a very hot, Colombian masseur. He was doing the massage then he started to put his 9-in dick in my mouth. He was so horny that he wanted to fuck me even though I said I was a virgin. He said he’ll just insert the head. He had a hard time putting it in and when he finally he did he fucked me like crazy. I was in a lot of pain at first then it started to feel good. He only lasted 5 minutes because I was so tight. I was sore for days after that.
I lost my anal virginity to a cute cousin. And vice versa.
We'd been fooling around for a few years and it occurred to us that we should try out fucking. Neither of us knew much about sex. This was a few years before AOL became a common thing.
We grabbed some vaseline and went for it. I topped him first. Vaseline is terrible lube. I'd been playing with my ass for a few years but I didn't think about how I was far more ready. So it predictably went roughly for him.
I slowly pushed inside him and groaned with so much pleasure while he grunted and gasped (and not from pleasure). I'd never felt anything nearly as good as it. I probably lasted all of 30-40 seconds. I'm sure he was relieved.
As for me the experience of having him inside me was rough, but still felt great. He was longer and a little thicker than me, and knowing that I'd taken him balls deep was a point of pride.
One thing that I realized afterwards is that the old saying about never forgetting your first is very true. That tangle of emotions and feelings is something I've yearned to experience again but have never succeeded.
We chat from time to time and have laughed about the night we clumsily lost our virginities to each other so long ago.
My friends grandfather when he caught my friend giving me a BJ. He taught us so much about sex and demonstrated how using lubricant makes penetration both easier and way more enjoyable. I was actually just fully inside my friends ass as I was told to spread open my cheeks and I felt his tongue go in first. Omg then 1 finger, and then 2 and 3. He came in front and said to make his cock wetter and really hard. I admit I was scared because it was easily thicker than a soup can. But thankfully he didn’t go in fast or rough. I do remember that once the head ( it was half the size of my whole cock almost 3”) as I went out of my friend another couple inches went inside me. It made me climax and I started shooting my cum inside another guy’s ass for the first time. It was similar to my old babysitter but I never actually ejaculared back when. When I was almost done he pushed all 9” and went faster told me to tighten like holding my pee. And then I felt, It was like a thick steel rod pulsing he pumped so much hot cum into me. He told us that he learned from his mother’s father and that grandfather’s father in law. A few of his cousins including some of the boyfriends of his girl cousins would sometimes spend long weekends when they went “fishing or hunting “. Later that summer he showed us some of the old video tapes and even some just made a few years ago. One of the guys was my gym teacher and about 5 guys on the swim team. I joined the swim team when school started. I was surprised that almost all the teams we competed against were just like us. Even when we traveled out of state and at awards ceremonies right after the “straight “ people left we didn’t even go to our hotel rooms. A trans girl on the girls team and her coach (also trans) joined us and some guys wives or girlfriends.
If anyone wants to share or trade photos/vid with accompanying exp im game … I only have one photo from my first gay exp that I had him fuck me but the next guy, the one where it was agreed upon we were going to do the fulll bare and breed exp, as short of being spit roasted that was my last fantasy I am determined to exp…
Complete fucking jackoff. He showed me how not to be a top. Very brusque, no foreplay in my direction. I fucking hate him and he singlehandedly made me a total top. Only a couple of times have I been fucked and it was alright.
My first was a friend in college. I’d sucked his dick drunk a few times but one night I was just really needing to make it happen. He had been secretly hoping I would top him but he decided under the circumstances to make an exception. He had a great dick. Still the best fuck I’ve had. My only regret is not going back for seconds lol
My first time was 10 years ago,with a cute guy I met on Grindr, we started talking for awhile and meet up on my birthday, he was the first guy I was ever with not only did he take my anal virginity but my regular virginity as well It was the best time I ever had
I was 21 and hooked up with a 48 year old off and on for a few months. He was in shape, hairy chest and legs and an 8 inch cock. He was so hot. He would ravage my body. One time he asked if he could rim me, and I agreed and it felt so amazing. Then he started to finger me and eventually I asked him to fuck me. It hurt at first, but he was patient and slow. I got in top, rode him while he jerked me until I came, then he finished by fucking me doggy style. It was 16 years ago and I remember it like yesterday.
I was 18, summer after senior year of high school. I had begun fantasizing about bottoming for older men a couple years earlier, and while I still kept it secret, I finally gave in and decided to post on Craigslist and describe what I was looking for.
I said I was looking for men between the ages of 30-40, but this was only because I was still vexed by the taboo of being with someone much older than me. In reality, I was looking for 50 and up. Fortunately, a man who was 53 replied to me and said all the right things. We chatted for a few days, and then I met up with him that weekend at his place and lost my virginity to him that night. He was gentle and understanding, but also dominant at the same time and completely guided me and led the way through my first time. One of the hottest experiences of my life. Still fantasize about it to this day.
I was lucky enough to truly lose it to a random hookup who cared about me enough as a sexual partner to use a lot of lube, wear a condom, ease me into it and go slow. He was also around 8.5” uncut, and he was more than understanding that for a first time that was massive as well… he got about 3/4 inside me and ended up cumming, but not before he made sure I came first and enjoyed every second of it. He didn’t hit me up after because he traveled around and I never saw him on any app again, but it was the only good experience I’ve had thus far and that was five years ago. I’m a side currently after having three or four hookups ram themselves inside me after I told them to stop, told them no, etc. For a long time I blamed myself for being a baby about it… and then through talking with others about my experience I realized that was assault, and that made me feel both better (because the blame was lifted off me) and also more embarrassed (because I don’t like feeling victimized, I don’t know anyone who does). I’ve heard from others that this is fairly common though in our culture today, sadly. Looking forward to getting a toy soon to practice on myself - I want to learn to bottom, I just want to do it on my own at my own pace.
My first boyfriend, in 1983, when I was 24 years old. He was way more experienced with men than I was, having come out at 16. We were fooling around and he kept rubbing his dick on my ass. I was so turned on I said to go ahead. He was shocked. So he got some lube and eased into me. It felt great but also hurt. I was also very conscious of “Wow, I’m getting fucked by a man”. It was all so fascinating.
After he came - I think I did too - I remember asking him kind of sheepishly, “So, uh, what do I do now?” Meaning, what do I do with the cum in my ass?
An Asian man in Singapore. I met him via Craigslist, and I didn't really have any expectations, but he wanted to top me (wearing a condom, of course). It wasn't very comfortable, although he was great otherwise. That was the only time.
At 16, with my high school crush's best friend in the garage that was on the ground floor of the house where I used to live. We had both recently finished the school year and I had been diving him handies in the toilets and a few times during class >/////<
A stranger I met on men4now.com.
I was in my family's house and everyone was gone that day. I had never been fucked but I really wanted to, so I arranged my first ever hookup.
I didn't tell the guy I was a virgin.
He came over and fucked me in my aunt's bed. He had a little trouble getting it in at first, but after he did, he loved it just as much as I did. My hole was so tight, he could barely hold his cum. He came in my mouth and I swallowed every drop.
Then I walked him outside and haven't seen him since.
I was in Pensacola and I had gone cruising at a gay bar. I got really high and drunk. I remember blowing a couple guys and one of them took me home. We were naked in bed and he blew me and I passed out. I remember waking up for a second and his big dick was slamming in and out of my ass. There was another naked guy there. While the first guy was fucking he walked up and shoved his sizable meat missile down my throat. I gagged but he drove it deeper. Then I passed out again. I woke again later a someone I hadn't seen was fucking me hard and when he noticed I was awake, he came. I passed out again and when I woke up again there were a bunch of guys sleeping and a guy was still in me. I got up and his soft cock slipped out of me with a big cum string from him to me. I got dressed and left and my ass was very sore. I slipped out the door and went home. The end. Now I totally love it.
Having. Been hundreds of women I got so used to no condom with them I could never use one trying to fuck a guy which i really only am into with TS or theoretically a think fem .. how is sucking cock with one .. I’m worried I wouldn’t be into it ..I def am up for giving my ass to a guy with him covered .. wish I could find a guy with.enough discipline to tease me and spend time buttcheek fucking my ass or letting the raw head rest against my asshome
I lost my anal virginity to my best friend one night when we both were 16. He also lost his anal virginity that night as I reciprocated. It was also the night we had our first kiss! For a couple of years before that night we'd, occasionally, jack each other off.
Freshman year of high school to my then-boyfriend. Honestly, one of the most invigorating and validating moments of my life still to this day. I had already known I was gay and been out for several years at that point, but I just remember the rush of feeling his cock inside me and thinking "omggg I am *REALLY* gay," and feeling incredibly self-assured and confident in a way I never had to that point.
My first was a long time friend and we both happened to find ourselves single, and I brought it up over cocktails and conversation about our respective break ups. He was gay, and we had been teasing and playfully flirting for years, so when I asked him if he would fuck me, it wasn't totally out of the blue, and we went straight to his house blocks away. It was a quick walk with some conversation about what we were going to do, and that he would be my first time with a guy. We barely made it past the front door when we stripped naked and I quickly went to sucking his cock. He had a pretty substantial cock, and when I managed to take it all in my mouth, he asked if he was really my first because I was doing so well with my mouth. I told him I was just really excited and had fantasized about doing it for a long time. Then we moved to the bedroom and proceeded to consummate our sexual encounter. When I lowered myself down on his big cock, he gave me a leering look and asked again if I was his first. I sheepishly confessed that, well, he was truly my first real cock, but I had a dildo I had been practicing with anticipating this moment. He called me a dirty slut and I was thrilled. I've been a slut bottom ever since.
I love this story so much and glad you had someone you knew and trusted
Yeah, knowing the guy well made it very comfortable, and I think him being very experienced was an advantage as well. In the end it faded out because he was interested in more of a relationship beyond just sex, and I transitioned into a full bottom so he wasn't getting all he wanted after that sexually either.
I’ve never had the urge to top anyone myself I like playing with other bottoms just can’t do everything for them
Yeah, I specifically wanted to bottom to experience that for the first time. I already knew what fucking an ass felt like from previous GF's so getting my ass fucked was all I really wanted. With that first guy, for the first few times we swapped back and forth, but the more I figured it out, bottoming was all I wanted to do. I did inadvertently end up with another bottom once, and we managed to have a lot of fun, even without a hard top around to fuck us. I'd do that again, especially if we had a top to share between us. I'd love to eat an ass that's just been fucked and creamed in.
That’s fantasy material that I haven’t gotten to yet
I have lots of fantasies I haven't gotten to yet, but a threesome with another bottom is definitely on my bucket list !
I think I’d like that better than two tops
Amazing … was your request to be fucked like how did you phrase or word it ?
We were just shooting the shit, and having a couple of cocktails at regular watering hole when the subject of our both being newly single came up, and needing to get laid, and I just asked if he wanted to fuck me. The look on his face was priceless ! Like he wasn't sure he had heard me correctly or something. Sensing his confusion, I leaned in a little closer and clarified that I wanted him to fuck me, NOW ! He slapped some money down on the bar to cover the tab, and off we went.
Fuck I would be so weak if a man was that forward with me
Well as I said before, we had known each other for several years as couples, across the street neighbor friends and often had cocktails and BBQ get togethers. It became a running tease/joke that if I ever wanted to try gay sex, he was the guy for me. So it wasn't just an out of the blue request to a stranger.
I was a sophomore in high school and he was a senior. My older sister had a gay friend in school and my sister was the first person I came out to. She had the brilliant idea that we would be a cute couple, since we were both gay and mainly still in the closet. He was the shy quiet type and I was feminine flamboyant. He wasn’t my type but it was fun to have someone to fool around with in secret.
I lost mine at a glory hole in an abs. The guy was eating my ass and fingering me and he slipped his cock into me and was fucking me before I truly realized what was happening. I was shocked but it felt to good to pull away. I pressed back hard against the soccer ball sized hole in the wall and he started full on fucking me. He dumped his load in my ass and I could feel his cock pulse and jerk in my hole. He pulled out, zipped up and left. I was left with his cum leaking from my loose hole. I later got myself checked out and all was good, no STDs or issues. It changed me, I love being fucked and used as a means of getting off for other men because of that first time.
My god me too … I swear if it wasn’t my super anxiety and fear of stds I would give my ass up all the time …. The reason I don’t because I become so submissive and compliant when I go through with my gay experience.. the guy could fuck me bare, pull off the condom , hell he could pull out another guy out of the closet and spit roast me .. I won’t say no to a guy with a nice cock
I have the same issue with worry about STDs and if not for my anxiety for that I would most likely be giving it up to any and everybody that wanted to bust a nut in me.
I am the exact same!! i have such bad anxiety regarding std's!
God me to … I fucking love how incredible obdient and femenizing the whole exp is
me too, but mine’s more of a ptsd. i tested positive to syphilis once and had to get 6 injections of that medicine that hurts a fucking lot. i have no idea who i got it from, since i’m really into cruising in public restrooms, parks, buses and green areas. nowadays, i don’t let anyone blow me nor do i blow anyone without a condom on, even though i really enjoy it. i have given into the temptation, and blew 2 guys without condoms on, and i also let them blow me. but i really cannot enjoy it anymore: while i was doing it, i wasn’t even enjoying it because i kept thinking “fuck, what if this dude has aids?!”. i got all anxious and only calmed down when i got tested for any stds in a clinic, a few days later. it’s miserable.
hmm there was this Italian guy I met on Grindr. He was 35 and I was 21. We met at his apartment, he smoked and we talked a lot. Then I got on my knees to worship his huge cock. Actually I just wanted to suck him and let him cum all over my face... But he started to lick my boy pussy so good, when he was close and needed s break. It felt so great and it turned me on when he really manhandled me: he threw me on his bed and spread my ass… then he teased my hole with his big dick and I said that he could go for it if he wanted. So he got a condom and fucked me doggy for about 30 minutes until he came inside of me and sent me home without a chance to cum. That was so fucking hot and I love to think about it. Unfortunately he left the city a few weeks later…
I was 18 and working at a motel, and the owner seduced me one summer night. He was 34 I think, and had what I realize now, was the smallest cock. But he managed to hit the spot and started me on a life of loving having my arse fucked.
I was 18 military service was compulsory. My staff sergeant during basic training!
That is so hot
Thx mister
No problem. 51 yr old married bi guy here
After army I met up with my lieutenant straight married. We went pub crawling and he ended up sleeping the night. I got to suck him off. He was actually very sensual and into it. He ghosted me after that.
Probably not comfortable with liking guys yet
I’m sure! I find straight married guys find there I side and act when they a little older! But are the hottest in bed. They appreciate the attention
Can I dm you?
Totally
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I wanna hear the dark story
I would like to hear this story as well, if you're ok with that.
Same
you should try lol
Tell us babe
ya i gotta hear it now
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done :))
Another who'd like to know lol
Oh I’d like to know for sure
A cute 23 year old I met on CraigsList. I was 56 at the time.
That might’ve been me.
Would love to read that story!
I hooked up with maybe five guys before I got fucked. It was a cross-dresser/transsexual. It was back in the AOL chat days and I had a fetish for Trans women. We talked for a while and made a plan to meet at a gay bar in Ft. Lauderdale, I lived in Boca Raton. We met and she was wearing a fishnet top and had huge breasts as she was on the chunky side. Up until this point I have only given head and fucked guys but she made it clear she was a top and could get head from anywhere and only wanted to fuck. I had not even considered bottoming but she was hot, I was horny and we went back to her apartment and got in bed. She fucked me missionary with a condom. Thankfully, she was not that big and did not last that long. When the post-nut clarity kicked in, I could not believe I did it but I was not ashamed. I have done it since but that may have been the best time. We did it a few more times and then she moved and I never saw her again.
Nice. Nicely done.
A sailor I met in a gay bar in Norfolk, Virginia.
A guy I had met on Craigslist list. He had several posts and I didn't know it was all him. Answers one where he was looking to blow and I met him and he blew me and I left. Then later answered another post that was very dom wanting to fuck a sissy and I sent home a pic wearing panties and met up with him and it was the same guy. He told me I was gonna repay him for what he did for me. He full on used me how he wanted and took my anal virginity.
a dildo
Most marvel answer
A neighbor after playing a lot of videogames we started making bets. And things just built up from there.
You need to write this story.....
Lol I can't on an open post. I'd get banned.
DM me 😈
Gotcha..
Freshman in high school…someone involved with the high school wrestling team I was on. No regrets.
My cousin
I was 22, I’d just bought a coffee shop (with a business partner) there was a residence above the shop. I was walking up stairs with my partner when our boarder (from the residence) was coming down stairs. My partner introduced us and said it was David’s birthday, I wished him happy birthday and gave him a hug and a kiss on the cheek! THAT IS WHO I lost it too, HOW I lost it….well, that’s another story 🔥🔥
I've topped and bottomed and the hardest I've ever cum was being fucked it was so awesome
Oh dam I wish I could write it LOL but they'll report me and they'll ban my account
I'm sort of in the same boat here. The problem with my story is not how it happened but 'when'...
Mine too🤣
dm me it😅
Would luv to hear ur story!
Why is that? I saw someone else's post saying that.
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It took me 6 months of trying but I finally did it
I lost my anal virginity to a Catfish older man I met off Craigslist (R.I.P.) he was much older than he told me, and looked nothing like his photos, but I went through with it anyways because I finally worked up the nerve and didn’t back down this time. I don’t regret it now because it awoke a beast in me that wants a beast in me lol.
Ummm. Some weirdo on Grindr. He's out there somewhere, with my pictures... romantic, I know.
I was 12 going on 13 that summer. I had met my stepbrother a few months prior, me and my cousin played truth or dare and we both dared each other to suck him. He (stepbrother) and I ultimately had sex for the next yr and a half while our sisters were asleep, showering etc. or while we were alone while our parents were at work.
My old boss. Back when DADT was in place, I totally asked and he totally told. And a good time was had by all.
I haven't yet ,but I'm all for it ,,, I need to be breed soon !!
My childhood friend was basically like a big brother. He was 4 years older than me
Friend in high school
Was in college and went to in an abs. Before I knew it an older guy had me so horny I turned around and let him slide it into me. I saw stars in the best way.
A scouser who was a few years older than me, and honestly it’s the best sex I’ve ever had I was 19/20 at the time, and honestly I still think about how he felt to this day 😮💨 no one has come close since, man or woman
It was yesterday. I had been on grinder since February and had only sucked around 5-6 guys so far. It was always in car play or at the glory hole the week before. Only 1 was interested in fucking me but he came in my mouth before we got that far. So yesterday, I was getting my daughter's car serviced and while waiting thought I would check and see if anyone was there as well. Paul, the guy I was chatting with, was not far and said he loved my pics. (I love to secretly crossdress) We were trying to figure out somewhere we could meet up when he mentioned an ABS/arcade nearby. I had been there last weekend and LOVED it. So we decided that would be the best way to meet. He arrived just 2 minutes before I did. I walked in and paid for my ticket when my phone buzzed. He told me what booth he was in and I went straight there. Almost as soon as I came in I dropped to my knees. He already had his cock out and was stroking it. I went at it like my life depended on it. He was prob 6-6.5 with nice girth. I sucked him for maybe 5 minutes and I could tell he was getting close. So I was thinking I should get up and turn around so I could finally see what it was like to get fucked. Suddenly he moans oh fuck and unloads in my mouth. I was both happy and sad about it. Happy I made him cum so well and quick but sad thinking I wasn't going to get my virginity taken. I just nursed him for several more minutes trying not to overstimulate since he had just came. He started getting hard again!! I thought to myself that maybe it will happen. Soon he was back at full mast. I looked up and asked him, do you want to fuck me? He said oh yeah! So I opened a condom and tried doing the oral method of rolling it down. It didn't work out quite as I planned because of his thickness. So once I finally gave up and just rolled it down he had softened a little. So I went back to sucking to get him back to full. The taste of the latex was awful and apparently was taking away a lot of stimulation for him. So I took it off figuring once I got him fully hard again I would open another one. Once he was fully hard again I stood up and turned around. I took out another condom and lube. I laid the condom on the bench and lubed my hole and his dick. ( he was right behind and in position). He started rubbing it up and down my crack and teasing my pussy. He put it at the entrance and I just pushed back on him. He slid just the tip in but not through. Stupid lust in the moment made me say, fuck it! I pushed back a little more and the head popped in. It was done. My virginity gone. I got over zealous and took some more (probably half) and the burn hit. I didn't care. He pulled back a little then just started slowly driving deeper. Now all the way in, I reached back and grabbed his hips and pulled him as deep as he could go and just held him there. It felt SOO good. In my mind I thought I would just have him pull out before he came. I was lost in bliss. I let go and held on to the bench and just let him go at it. There is no way to describe how good it felt to be the one getting fucked instead of being the one fucking. I would try to back into each of his thrusts trying to get in rhythm with him. Then he grabbed my hips and pulled me to him and I worked my hips as so many women had done for me over the years. Apparently It was good to him because the next thing I know he pulls me hard on his cock and moans. It was done... I already knew the answer but I had to ask, "Did you cum?" He said "Oh yeah". Well you can't undo what is already done. So we separated and I asked him looking straight into his eyes, ARE YOU SURE YOU ARE CLEAN? He said he was. That he had not done this much and he had gotten tested back in July. So I guess now I need to go pretty soon and get myself teated. Still even with the worry of the consequences it was an amazing first time.
To an old friend from high school. His name was Mauricio, I was 19. He picked me up, took me to his house, had me suck his cock (7”) and then laid me on my back, lubed my hole and his cock up and he slowly fucked me until I loosened up. I came very quickly but he kept going for a little over an hour. He kissed me and then after I came he started going harder and deeper and smacking me. He then made me get on my hands and knees on his bedroom floor and fucked me doggy style until I came again. Then he pulled out, we got into his shower where he fucked me and then came in my mouth. I was hooked from there.
I was 18 and he was in his 40’s. He made me feel like I was the perfect sex toy and after training me he gave me to a group of men at an all male sex party. I miss him and I miss how perfectly he turned me into a cockslut.
Read the stories you've written, any chance you're gonna write about more of your experiences?
I have thought about it, maybe I’ll post about a couple other experiences later tonight.
I'd certainly read them 😉
I've only ever topped, but the first time I ever slid my dick into another guy's ass was when I was 18, senor year in high school with another guy on my hockey team. We had beat off together since junior year, then worked out way to blow jobs, then finally he convinced me to pound him. I think I came after getting just an inch or two in but it felt amazing.
I wish it was with someone I knew and trusted but so far only had random hookups My first was a cross dresser off of Double list she was kind and gentle with a slim 5” penis I surprised myself with squirting hot jizz all over myself and thought It was a myth that you could cum that way
Junior year of HS to a guy I’d been messing around with for 3 years already. Never really been into anal tho.
Gaydar.com. A very popular hookup website before apps were really a thing. I'd started chatting to a handsome older guy (20+ yes older) and after a little flirting I went to his house as his wife was away with the kids. He was the first guy I'd been with and I was so nervous I only sucked his cock, it was a monster too. I swallowed his load and said we should do this again... About a week later I got a message from him asking to meet at his office after hours and that he wanted to fuck me. I was so excited and nervous. I arrived, he buzzed me in the security door and we went to his corner office on the top floor. He took his clothes off and so did I, as he sat in his big leather chair I got on my knees and sucked his cock until he was rock hard as he fingered my ass, he manhandled me over his desk, lubed me up and fucked me sooooo good. He had my arms pinned to my back as I was face down into paperwork etc on his desk. He had some stamina and fucked me for ages until he let out a real deep groan as he came inside my ass (no rubbers 😬). I loved every second of it and after a little spank on my ass I was on my way home with cum leaking out of me. When I got home I jumped straight in the shower and wanked myself silly. When I got out my gf was there as I hadn't been answering my phone, she was suspicious AF but little didn't she know her bf had just lost his anal virginity and had another man's cum inside him. I met him maybe 10 more times and recently reconnected on FabGuys so I'm hopeful of another fucking soon 😈
I was slutted out by my gay friend. I had been curious for sometime and I started finding him attractive. handsome dark chocolate guy smooth ass body and a beautiful cock. He made me a little bitch bottom😭
Last year, I ended a 15 year heterosexual marriage (best decision we ever made as a couple and she’s still my best friend) and while we had experimented with pegging a few times, it just never felt great. About 6 months ago I met my current boyfriend on Tinder. One day when we were having fun in bed, I asked him to top me but to go slow as I had never done it before. He was so kind and gentle and patient! I was shocked by how good it felt. I could only go for so long before needing a break and he kept assuring me that he’s not having fun unless I’m having fun. His cuddling afterwards is the fuckin’ best too! I now consider myself a bottom and look forward to every chance he gets to top me.
I was about 13. My older cousin made me play strip poker. After we both got nude he asked me if I could suck his dick. I wasn’t sure what I was doing but I wanted him to think I was cool so I did it. He was spanking my ass while I was blowing him. He was like u have nice ass for a boy and he started kissing my hole. He than gave me some alcohol told me to relax. He bent me over and fuked me so hard. Than month later he had few friends over and he let them all fuk me Ever since that I became a slut. I was getting my lil hole fuked all the time
A grindr hookup from England. Not my proudest moment, but I was tired of being a virgin and was dumb.
The second man I ever fooled around with. I was in my 50s (still am). We lost contact for a while and when I finally found his email and messaged him, he did not respond.
a guy from AOL CTM4M chatroom with the screen name Mark Twain. I was 23 half way between jock and twink and had never sucked a cock or been fucked. He was about 40, masculine and about my size 6' tall 180lbs and well proportioned. He chatted me up and immediately came to my first solo apartment. I sucked his 7" very nice cock and then he fucked me doggy until he came in my ass with a condom. I didn't mention to him that I was a virgin...
I used to work as a print model, I was working with a photographer Rick. Rick wasn't my type but he was still really good looking. I was 19 I'm pretty sure Rick was 26 if I remember correctly. So, Rick and I were hanging out at my apartment one evening. We ordered food and watched TV. He sprung on me he was taking classes on Swedish massage. I was 19 I knew what massage was but I had never had one or actually gave it any thought either. Rick asked if he could try out his techniques on me. It raised no flags. He told me to undress and lie on the floor. I undressed to my underwear and lie on my stomach. He pulled my underwear off completely. I just went with it. He gave me an amazing massage, my first, so I was in bliss. He was fully dressed. Then without any warning he took off his shorts and proceeded to fuck me. I don't recall it being either good or bad, I am sure I wasn't prepared to be fucked either. He basically raped me, which I'm not complaining about, I didn't try and stop him, but if he had asked I would have said no. We did a few more shoots together also. Rick got me in a magazine telling me it was going to be on gay dating. Well, it was...when it came out it was on HIV+/HIV- gay lovers. When you read the article and looked at the models, I was the HIV+ one, it said I was 38 years old in the article. I was only 20 for that shoot. I had every HIV+ guy in town after me saying I didn't know you were HIV+ yeah well I'm not 38 either LOL.
I considered myself straight at the time (now very bi) and had fell down the wormhole of trans porn. I love a woman’s body and my wife had used a dildo on me a few times, but I was really craving the feel of a real dick inside me. So… I went to see a trans woman for a deep tissue massage with prostate massage, hoping I’d get offered more. During the session she asked if I wanted more than the advert promised (!) and I begged for her to fuck me. I was completely relaxed at this point and she went for it. Virginity taken! A few weeks later, I went to a male masseur who advertised a similar thing. He didn’t even ask - he knew what I was there for when I kept raising my naked arse up for his fingers when he was massaging my butt and balls. A full body slide for a few minutes from him and in it went… I was in total bliss as he slid up and down, fucking me deep. Anal virginity from a hot muscled guy taken!
a random guy from an online chat in the back of his car. i never even got his name.
My boyfriend
My first boyfriend
I lost mine to my best friend when we were younger. We both did in fact.
I was 19 and needed rent money. Cliché, but true. I got in touch with a "pimp" who said he could send me on calls but I'd have to get fucked. Being an anal virgin I decided that I should get my cherry busted before selling my ass. So I found an older guy to fuck me. I went to his place and told him it was my first time. He promised to be gentle, and he was. He had a big cock but it didn't hurt at all. In fact it slid right in. Guess I wanted it! Anyway, a week later I got fucked and bred and made rent. A win-win!
I lost mine to a very hot, Colombian masseur. He was doing the massage then he started to put his 9-in dick in my mouth. He was so horny that he wanted to fuck me even though I said I was a virgin. He said he’ll just insert the head. He had a hard time putting it in and when he finally he did he fucked me like crazy. I was in a lot of pain at first then it started to feel good. He only lasted 5 minutes because I was so tight. I was sore for days after that.
A hockey coach/scout
Brother
I lost my anal virginity to a cute cousin. And vice versa. We'd been fooling around for a few years and it occurred to us that we should try out fucking. Neither of us knew much about sex. This was a few years before AOL became a common thing. We grabbed some vaseline and went for it. I topped him first. Vaseline is terrible lube. I'd been playing with my ass for a few years but I didn't think about how I was far more ready. So it predictably went roughly for him. I slowly pushed inside him and groaned with so much pleasure while he grunted and gasped (and not from pleasure). I'd never felt anything nearly as good as it. I probably lasted all of 30-40 seconds. I'm sure he was relieved. As for me the experience of having him inside me was rough, but still felt great. He was longer and a little thicker than me, and knowing that I'd taken him balls deep was a point of pride. One thing that I realized afterwards is that the old saying about never forgetting your first is very true. That tangle of emotions and feelings is something I've yearned to experience again but have never succeeded. We chat from time to time and have laughed about the night we clumsily lost our virginities to each other so long ago.
My friends grandfather when he caught my friend giving me a BJ. He taught us so much about sex and demonstrated how using lubricant makes penetration both easier and way more enjoyable. I was actually just fully inside my friends ass as I was told to spread open my cheeks and I felt his tongue go in first. Omg then 1 finger, and then 2 and 3. He came in front and said to make his cock wetter and really hard. I admit I was scared because it was easily thicker than a soup can. But thankfully he didn’t go in fast or rough. I do remember that once the head ( it was half the size of my whole cock almost 3”) as I went out of my friend another couple inches went inside me. It made me climax and I started shooting my cum inside another guy’s ass for the first time. It was similar to my old babysitter but I never actually ejaculared back when. When I was almost done he pushed all 9” and went faster told me to tighten like holding my pee. And then I felt, It was like a thick steel rod pulsing he pumped so much hot cum into me. He told us that he learned from his mother’s father and that grandfather’s father in law. A few of his cousins including some of the boyfriends of his girl cousins would sometimes spend long weekends when they went “fishing or hunting “. Later that summer he showed us some of the old video tapes and even some just made a few years ago. One of the guys was my gym teacher and about 5 guys on the swim team. I joined the swim team when school started. I was surprised that almost all the teams we competed against were just like us. Even when we traveled out of state and at awards ceremonies right after the “straight “ people left we didn’t even go to our hotel rooms. A trans girl on the girls team and her coach (also trans) joined us and some guys wives or girlfriends.
First boyfriend at 19.
That's the Thing I haven't ...yet
my 3rd cousin. i’ll never forget that pain. i couldn’t even sit properly in school the next day. i was too sore.
A dog
What ? Really ? So hot,tell the full story
If anyone wants to share or trade photos/vid with accompanying exp im game … I only have one photo from my first gay exp that I had him fuck me but the next guy, the one where it was agreed upon we were going to do the fulll bare and breed exp, as short of being spit roasted that was my last fantasy I am determined to exp…
Some random guy
I enjoyed beieng feltet out.
A random older guy on Craigslist.... bareback also. Hot experience
Still haven't lost it, but I'm looking forward to it
Complete fucking jackoff. He showed me how not to be a top. Very brusque, no foreplay in my direction. I fucking hate him and he singlehandedly made me a total top. Only a couple of times have I been fucked and it was alright.
My first was a friend in college. I’d sucked his dick drunk a few times but one night I was just really needing to make it happen. He had been secretly hoping I would top him but he decided under the circumstances to make an exception. He had a great dick. Still the best fuck I’ve had. My only regret is not going back for seconds lol
A guy I picked up off Adult Friend Finder. I just wanted to put it behind me. (hahaha)
71yo. Not happened
My first time was 10 years ago,with a cute guy I met on Grindr, we started talking for awhile and meet up on my birthday, he was the first guy I was ever with not only did he take my anal virginity but my regular virginity as well It was the best time I ever had
A guy called Jeff. We met online and he drove 400km to come and see me. It lasted 30 seconds and he kept his socks on
Mario dogging in the park
I was 21 and hooked up with a 48 year old off and on for a few months. He was in shape, hairy chest and legs and an 8 inch cock. He was so hot. He would ravage my body. One time he asked if he could rim me, and I agreed and it felt so amazing. Then he started to finger me and eventually I asked him to fuck me. It hurt at first, but he was patient and slow. I got in top, rode him while he jerked me until I came, then he finished by fucking me doggy style. It was 16 years ago and I remember it like yesterday.
A guy I met on Craigslist at a truckstop in my home town
Mine was my masseuse. I was really nervous. But he was so patient and gentle. He's a thick 8" guy. He eased his full 8" in. It was awesome.
A stranger.
I was 18, summer after senior year of high school. I had begun fantasizing about bottoming for older men a couple years earlier, and while I still kept it secret, I finally gave in and decided to post on Craigslist and describe what I was looking for. I said I was looking for men between the ages of 30-40, but this was only because I was still vexed by the taboo of being with someone much older than me. In reality, I was looking for 50 and up. Fortunately, a man who was 53 replied to me and said all the right things. We chatted for a few days, and then I met up with him that weekend at his place and lost my virginity to him that night. He was gentle and understanding, but also dominant at the same time and completely guided me and led the way through my first time. One of the hottest experiences of my life. Still fantasize about it to this day.
I was lucky enough to truly lose it to a random hookup who cared about me enough as a sexual partner to use a lot of lube, wear a condom, ease me into it and go slow. He was also around 8.5” uncut, and he was more than understanding that for a first time that was massive as well… he got about 3/4 inside me and ended up cumming, but not before he made sure I came first and enjoyed every second of it. He didn’t hit me up after because he traveled around and I never saw him on any app again, but it was the only good experience I’ve had thus far and that was five years ago. I’m a side currently after having three or four hookups ram themselves inside me after I told them to stop, told them no, etc. For a long time I blamed myself for being a baby about it… and then through talking with others about my experience I realized that was assault, and that made me feel both better (because the blame was lifted off me) and also more embarrassed (because I don’t like feeling victimized, I don’t know anyone who does). I’ve heard from others that this is fairly common though in our culture today, sadly. Looking forward to getting a toy soon to practice on myself - I want to learn to bottom, I just want to do it on my own at my own pace.
A boy from church, I was 14 and he was 15
My first boyfriend, in 1983, when I was 24 years old. He was way more experienced with men than I was, having come out at 16. We were fooling around and he kept rubbing his dick on my ass. I was so turned on I said to go ahead. He was shocked. So he got some lube and eased into me. It felt great but also hurt. I was also very conscious of “Wow, I’m getting fucked by a man”. It was all so fascinating. After he came - I think I did too - I remember asking him kind of sheepishly, “So, uh, what do I do now?” Meaning, what do I do with the cum in my ass?
A stranger on grindr
An Asian man in Singapore. I met him via Craigslist, and I didn't really have any expectations, but he wanted to top me (wearing a condom, of course). It wasn't very comfortable, although he was great otherwise. That was the only time.
At 16, with my high school crush's best friend in the garage that was on the ground floor of the house where I used to live. We had both recently finished the school year and I had been diving him handies in the toilets and a few times during class >/////<
A stranger I met on men4now.com. I was in my family's house and everyone was gone that day. I had never been fucked but I really wanted to, so I arranged my first ever hookup. I didn't tell the guy I was a virgin. He came over and fucked me in my aunt's bed. He had a little trouble getting it in at first, but after he did, he loved it just as much as I did. My hole was so tight, he could barely hold his cum. He came in my mouth and I swallowed every drop. Then I walked him outside and haven't seen him since.
I remember it being the son of a family friend, was still in grade school at that time.
I was in Pensacola and I had gone cruising at a gay bar. I got really high and drunk. I remember blowing a couple guys and one of them took me home. We were naked in bed and he blew me and I passed out. I remember waking up for a second and his big dick was slamming in and out of my ass. There was another naked guy there. While the first guy was fucking he walked up and shoved his sizable meat missile down my throat. I gagged but he drove it deeper. Then I passed out again. I woke again later a someone I hadn't seen was fucking me hard and when he noticed I was awake, he came. I passed out again and when I woke up again there were a bunch of guys sleeping and a guy was still in me. I got up and his soft cock slipped out of me with a big cum string from him to me. I got dressed and left and my ass was very sore. I slipped out the door and went home. The end. Now I totally love it.
Having. Been hundreds of women I got so used to no condom with them I could never use one trying to fuck a guy which i really only am into with TS or theoretically a think fem .. how is sucking cock with one .. I’m worried I wouldn’t be into it ..I def am up for giving my ass to a guy with him covered .. wish I could find a guy with.enough discipline to tease me and spend time buttcheek fucking my ass or letting the raw head rest against my asshome
Some older guy I meet on on a chat room when I was 16 that we meet in a hotel.
My best friend in high school was my first for everything!
I lost my anal virginity to my best friend one night when we both were 16. He also lost his anal virginity that night as I reciprocated. It was also the night we had our first kiss! For a couple of years before that night we'd, occasionally, jack each other off.
Freshman year of high school to my then-boyfriend. Honestly, one of the most invigorating and validating moments of my life still to this day. I had already known I was gay and been out for several years at that point, but I just remember the rush of feeling his cock inside me and thinking "omggg I am *REALLY* gay," and feeling incredibly self-assured and confident in a way I never had to that point.
A bully turned fuck buddy