What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
What country and/or city do you live in? Somewhere in Asia
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Student
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Hindu
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Fifty Shades of Gay

How long ago did this hookup happen? Less than a week ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day.

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He finally shows up at my door at 11pm. Slim, average height and skinny jeans. We shook hands. Oh and I was already in my bath robe. He kept his things away and mentioned that we move to the bedroom.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I will not attempt to do an E.L James but trust me, my attention to detail could put her to shame. It was an awakening or a moment of truth of sorts. I’m engaged to a lovely woman who’s perfect for me and we love each other deeply. Due to my education, I get to see my fiancée only for a few days every few months and normally the sex is great even though there have been times when I think I had porn induced ‘stability issues’. So the last time around this happened, I decided that the best thing for me would be to wean myself off porn and become more ‘human’ so to speak.
So what used to turn me on? My fiancée and porn: mature women (you’re 58? May I stick my tongue up your ass?) and – wait for it! – gay porn. The kind where the old hairy bulging bellied middle aged men pound the smooth, round, girly bottoms of teens and young boys. The kind where the younger bottom (as they are called) moan, wince and gasp when they are dominated. The kind where the bears would thrust their big thick penises into the waiting mouths of the young only to be slurped to glory and then later, have them spread their legs and gently enter their pink, tight anuses with their bulging bellies or their sloppy balls slapping against the young butts.
The kind of stuff I’d never really do but always enjoyed watching and jerking off to, though in all frankness and fairness I’ll admit that I’ve long wondered what it felt like to be dominated and have your anus filled with another man’s thick penis. In particular, a fantasy I jerked off to was the thought of a threesome with my friend’s parents where a younger me is fucked in the ass by the 60 year old dad of his while I would be eating his mother out. I therefore considered myself bi-curious but straight leaning (I would think she tasted yummy).
When I did decide to begin my no porn, masturbation & orgasm challenge (as it’s called PMO), I had no doubts I would succeed in detoxing myself. A week passed by and then one more, things were going solid. I did have erections but largely I thought the situation was well in control. But after that things began to change. The suppression had started to play tricks with my mind. I would find falling asleep harder, being restless and often on the edge. Slowly my straight erotic thoughts took a turn for worse and the gay thoughts began taking hold and take hold, they did very swiftly.
In one very wanton google searching session, I stumbled across some adult personals where men solicited the company of other men. A lot of them were routine commercial in nature where they offer any man of any religion, cut or uncut cocks, top or bottom, body to body massages and more. And then there were some where a bisexual man had posted the picture of his back seeking another bisexual. And then there were many other ads where a subservient young partner would offer his mouth and his anus to service a worthy cock. And one where a middle-aged bottom invited dates from well behaved, clean and hygienic men to date and bed. Tried responding to a couple of such ads to see what it is like but that didn’t go very far. The damage was already done and a seed was firmly planted in my mind.
A night passed by and I was still fighting hard to do away with wet gay dreams but I wasn’t making much progress. In a moment of particular weakness, I ended up posting an ad which invited well behaved, healthy men of all ages to take me out on a dinner date, treat me like a lady and get lucky with my virgin bottom. One male responded quite quickly asking me for pictures and other details of my body which I was only more than glad to share. I must admit that I felt like a woman trying to get laid. Soon after sharing my pics, I could no longer hold my excitement and I had to masturbate and release my load. And then my head cleared. I immediately went online, deleted the ad and the profile and went to bed being thankful that I didn’t actually do anything stupid.
A day or two passed without incident and I was feeling good about myself, albeit a little foolish for the wrong turns I took. A couple of days later, it came back in full force again. This time around, I ended up downloading Grindr- a gay chatting and meeting app. I used the app to chat and seek mature (40+) men and found 1-2 of them in the nearby cities but nothing much happened beyond a chat. I didn’t sleep that night out of pure excitement. Thoughts of how an older mature man would gently enter my tight girly anus excited me to no end and shocked me simultaneously. Oh and in my defence, I also installed Tinder to see if I could get some older women to bed.

The very next day after this episode, I was traveling to a city quite far away. As soon as I landed and checked myself into the hotel, it was all but certain as to what I might do. I started using Grindr and Tinder. Grindr would buzz all the time from men seeking to park their penises to bottoms asking if I could satiate them while Tinder would just buzz once in a few hours with a match who would quite quickly unmatch me when they find out that all I wanted to do was to get in between their legs. By evening, I had zeroed in on a 58 year old mature top who described himself as fit, married and clean and was staying a mere 2 miles from my place. I sent him a few messages to see if he could be the lucky one. But alas, he couldn’t!

As I was almost about to give up and retire for the night, there came a buzz. A 27 year old messaged me asking me if I were a top or a bottom. Bottom, I replied. Asked me for some pictures, to which I sent him one of my back. He quipped “love to enter that ass”. I guess I decided to go ‘cougar’ (I was the old one) and told him I’d like that. I blushed. He agreed and asked me if I like to be dominated, to which I promptly agreed. He, said “I can’t wait to enter that tempting hole and make you scream” to which I said, “This pussy aches for your cock.” I spent the next hour distracted and mildly nervous – I wanted to be at my best for him.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? In the bedroom, he quickly opened the robe and marvelled at my body as though it was God’s gift to mankind. It felt very nice actually. He threw me on the bed and started kissing my face and licked my ear, neck and throat. I’ve NEVER had foreplay this good. My fiancée has a lot to learn from this guy, I thought. Quickly enough, he had me powerless and started sucking on my nipples while occasionally running his hand through my balls and penis. He would cusp my chest in a way that would resemble a woman’s tits and would quip, “I could suck milk from this all day”. He was still clothed and would let me nowhere near his crotch. Not just as yet he would tell me. He was about to kiss my lips to which I quickly said a no. I began to ache for a change of routine. The foreplay got so painfully long and boring to a point where I was just itching to either suck on his penis or have me turned around and arouse my anus.
And get there we did! He spooned me and started running his hands around my butt and the ass crack. It was a real turn on. He started spanking me hard. Some of that was a lil too harsh but then I guess I enjoyed it just as much. He gently ran his fingers over my puckered hole which really excited me to no end. He then started kissing my butt and gently teased me with his tongue starting from my lower back all the way to just above my anus. Seeing how much I was enjoying this, he decided to change course. He ordered that I get down on my knees. He held my hand firmly around his waist and asked me to smell his cock from the underwear. Finally I was getting some action, I thought. In the most subservient way possible, arched my back, I bent over his crotch with my face firmly dug deep into his shorts taking long and deep whiffs of his penis. He then asked me to excite the tip of his penis with my mouth over his shorts.
By now, I was firmly his bitch. We both knew that. HE would fuck my ass at his will and I will bend over and give him a blowjob or present my ass as he desires. He then decided to take this to the next level and he uncovered just a part of his shorts- just enough to let his long penis out. It was a clean uncut long one but not too thick. I knew what had to be done. I slowly started licking the entire length of his shaft and slowly going all the way to the top. While at the top, I would open my mouth and give him head slowly. I would use my tongue to gently draw circles on the forehead and tease him. I slowly but steadily began taking it in deeper. Then he firmly held my head and slowly thrust it in deeper and had me deep throat him many times. He took his shorts off and told me to lick his balls. Slowly I began drawing my tongue around his balls. Often I would gently lift his balls up and start running my tongue from between the balls all the way to his shaft.
A few more minutes of teasing his balls, he promptly asked me to get back to sucking his cock. I must admit that I quite enjoyed this. I worked him sufficiently to erection and excitation when he said “Ok now, get on your fours”. I knew what would follow. I did exactly as ordered, put my head down and thought to myself “here it is! Here’s the moment I lose my anal virginity” as he proceeded to pull his shorts down, roll the rubber on to his dick. He took out the tube of KY jelly and I stuck my hand out so that I could lubricate myself well over and above what he’s applying to his own dick. He gave me some and I gently started smearing that on my anus and gently inserting first one finger and then another and pushing it in as deep as I could. Some more of the lube and I was all set to have him pound my mangina.
He positioned himself behind me between my legs and adjusted his height and angle and slowly started inserting the head first and pushing it deeper. Initially it was what you would expect- the feeling of something big invading your anus but then once I relaxed and felt ok with that, he slowly began going in slightly more deep and then it hurt like hell. He wanted to keep going but I knew that this was a problem with the angle. So he made me flip around, lay on my back and have my legs up in the air, chicken style, with my ass pointed out. He then was able to enter with relative ease and slid it right in. And BOY! What I felt cannot possibly be justified with words alone but here’s about how it feels- you feel a shaft going in and then your rectum is quite clearly confused and you start getting the feel of a bowel movement. But the trick lies in relaxing and letting him deeper inside you till the penis disappears and all you can feel is his balls slapping your butt.
Once he was deep inside me, I lifted my legs up and rest them on his shoulders and hugged him tight and close as he thrust himself deeper and deeper to my moans of pleasure and occasional displeasure. And this went on and on and on to a point where I was just tired of this. I just wanted him to cum and get out of me and my place. It got so boring and monotonous that it felt like we were not having sex, but more like he was “doing” sex to me. My ass felt just fine though, he was just doing something with his dick up my alley. This whole time though, I noticed that I did not have a hard on. In both the previous cases, beyond a certain point (usually after 5 minutes of novelty), his foreplay and my sucking just felt like doing it for the heck of it. Beyond those first few minutes, I didn’t do it because I wanted to or loved to, it was more like I had to.

Eventually it happened! No, he didn’t cum but it fell out and he was not hard enough to go back in soon again. He tried with more lube, he tried some foreplay on me but nothing worked. Finally he just buried his face on my neck and said “I’m gonna wait till I get hard again”. While for most, this would have been an insult, it was just a welcome relief for me. That’s where we end this. I replied “It’s fine, I’m good. Don’t worry about it” gently signalling that time’s up. He asked me “Do you wanna cum?” I said “Nah, I’m good. You might wanna wash up.”

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? He got up, removed the rubber and went to the bathroom to wash up while I lay there in the bed with a greasy bottom contemplating whether I should offer to get him off with a blowjob but then I decided against it. There was no way I was going to let him cum in my mouth. I put my bath robe on and as he was dressing up to leave, simply walked around just waiting for him to leave. I reassured him that he felt amazing inside me and he said my ass felt great too. With the mutual admiration out of the way, he left and closed the door hoping to never see him again. I flew out two days later and at the airport, even though I was hungover from previous night, I thought I saw him. Or someone like him. And that sent a very uncomfortable reflex down my spine.
So what did I learn from all this? My first one night stand with a stranger whose name I still do not know, I hope to never meet, took my anal virginity! Exciting right? Well, not quite. The thing is, it just firmly moved me from being bicurious to being firmly straight. I no longer have erotic thoughts of older men tearing up my anus with their penises. I guess while I’m glad I lost my anal virginity to a young, clean, and quite gentle guy, I’m certain I will want nothing to do with him. I would never want to ever see him again or even smell the same smells I had that night. I have nothing against him but I suppose it says a lot when I never looked into his eyes when he did anything to me or I did anything to him. I would either keep them firmly shut or look away. The fact that it felt so mechanical and above all, I never had an erection while having sex or more appropriately doing sex stands testimony to the fact that I didn’t enjoy it one bit. I guess the whole point for me was, been there, done that, now let’s move on with life. As far as my greasy bottom was concerned, I was pleasantly surprised to find only the lube all over my ass. Really none of the other gross stuff that might leak out. The best part? It didn’t even go out of shape. So here’s advice for the bi-curious amongst us- take the leap and get it out of your way. It doesn’t hurt. Your bowels will work just fine the next day morning and the doubt would have long left you by then.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, Submission / Relinquishing power

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Nobody

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? This was my first one-night stand and gay sex. Being the bottom certainly gave me more insight into how to be better to women. I would say that I’m a better lover because of this experience. Yes, I also liked going down on him for a bit. But above all, it was the thrill of both – gay sex and one-night stand.

What was the WORST thing about this hookup? Hardly much satisfaction in terms of an orgasm. Realized that I’m very firmly straight.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes, I’m open to sexual experiences and I can also very confidently tell you that anal sex isn’t as bad as people make it sound. What turns you on is deeply individual and may define your sexuality. I’ve learnt to appreciate people of different orientations.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup? I hope to keep this a secret forever.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I was firmly against one night stands and casual sex till now. To be taken by a storm by both- a one night stand and gay anal sex at the same time was quite an experience. I used to be old fashioned and probably still am. But I would now understand the extent of people’s actions driven by sexual frustration and repression.

What do you think about the Casual Sex Project? I think this is a fantastic platform for people like me who’ve had their multiple firsts on a single night to share and know what others think.

You have a hookup story to share? Submit it here!