At 21, I had not quite come out yet even though I had an inkling that I was gay. There were the usual suspicions: I had had a girlfriend for 2 months at college, and the relationship imploded very quickly; I thought one of my male classmates at university was super cute; when I watched straight porn, I enjoyed looking at the men.
This was heightened by the fact that I stopped dating altogether at university. While I wasn’t tall – 5 ft 8, maybe – I was confident, articulate and, when I needed to be, charming. I had also been told, by others, that they found me quite handsome. So, people speculated when I told them I preferred to remain single.
I was at university then in Singapore. My best friend at the time was R. We liked the same things: small talk, stupid jokes, trying to cook but failing miserably, etc. We generally got on very well.
R was what I think most people would describe as a cute nerd. He was taller than I was, about 175 cm or so. He was bespectacled and wore nice clothes, courtesy of a wealthy family. He was very fair and had a slightly toned chest and a flat stomach (he had taken up going to the gym over summer, and apparently his mum had hired him a personal trainer). His face wouldn’t be what anyone described as typically handsome, but with his height and shape, I could see how some people may have found him cute.
I had my own suspicions R was gay. Not because he was effeminate or flamboyant (although there is nothing wrong with that), but because he had a peculiarly fast friendship with this guy, Y. But whenever I asked R about him and Y, R would get a little mad at my probing and change the subject.
My 21st birthday was a simple affair. It was a small potluck in my room (thankfully, it was a rather large room with a separate living area) attended by about 10 of us. The evening ended with a few bottles of cheap wine from a nearby grocery store. As the clock ticked past midnight, each person eventually bade the remaining person’s farewell. By 1:30 am only R, Y and I remained – each of us tipsy from the wine.
I don’t quite remember how it started, but I believe R started asking me about my sexuality. He handled me quite smoothly when I became a little anxious.
“Don’t worry,” he said. “No one is saying you are gay.”
The point he was trying to make was that discovering one’s sexuality was a long and drawn-out process sometimes, and to figure that out, one sometimes needed to figure out what they liked or didn’t like.
He then asked me about my previous sexual experiences, of which I had very little. I had messed around with another guy when I was 17 – he was very handsome (or so I thought at the time), but that was it. And with my previous girlfriend, I had kissed her, but on the cheek.
“And how was it?” R asked.
“It was fine,” I replied.
“And did you kiss the boy you messed around with?”
“No.” This was true. We had jerked off in front of each other (and at times, each other), but it never went further than that. When I was 17, I wasn’t sure how to take things further.
“Then how do you know if you prefer kissing boys or girls?”
In a state of slight drunkenness, I thought R had a point. Before long, R asked me if I wanted to try to kiss a boy – in particular, R suggested that I could either kiss him or Y. “Just to see how you feel about it,” in his words.
I am not sure if it was the alcohol, or because R was actually being quite convincing, or a combination of the two, but I picked Y. I didn’t want to kiss R because, well, he was my best friend and it’s weird to kiss your best friend.
Also, Y wasn’t bad looking. Again, like the typical Singapore nerd sent to an American university, he was bespectacled and lean. He was a little more tanned, but he had a handsome face – long sharp nose, large dark eyes, high cheekbones, that sort of thing. And on this evening, his cheeks were flushed pink, which I found quite attractive. When he came close to me, his lips near mine, I could hear his breathing, short and sharp.
We ended up facing each other, standing closely, each too afraid to make the first move. The moment between us seemed to stretch for minutes, although I am sure it was far less.
Then Y kissed me.
It was my first kiss with another man. It was intoxicating, our saliva’s and alcohol mixing; and it was also sloppy, our tongues trying to figure out where to go and what to do.
We stopped to catch a breath. I realised I was as flushed as Y was.
And then we kissed again. The kiss was better the second time round. Y slowly pulled me into him, kissing me with the tenacity and confidence of a 21-year-old who was experienced and enthusiastic. This kiss went on for longer, and Y’s hands started to grab the back of my head. My hands slowly, and somewhat naturally, found their way around his waist. It wasn’t so much that I was attracted to Y (even though I am sure he was objectively attractive), or vice-versa. I think it was the fact that kissing another person could feel this good.
And then, during the kiss, I felt something brushing against my penis – I thought it was Y’s hands at first. It was at this time that I noticed that I was incredibly hard. I realised it wasn’t Y’s hands that had brushed against my penis, but Y’s penis, which was erect through his underpants and trousers. I stopped to look at him. By this point, we had both crossed the threshold from tipsy to horny, and the rosiness in our faces less to do with the alcohol now than the exhilaration of rushing hormones.
A hand curled in front of me from behind and slipped under my t-shirt. It was R, who slowly moved his hands from my stomach to chest, rubbing my torso gently as he embraced me from the back. I was a little stunned by this, and quite nearly snapped out of this drunken revelry. Just as I was about to ask him to stop, R found my nipples and started rubbing them gently.
It was the first time I had had that done to me and it felt electric. In the moment, it felt so good that I didn’t want him to stop. As Y kissed me again, my knees felt a little weak and I started breathing more heavily. Y’s hands proceeded to unbutton my trousers as R’s fingers continued to rub my nipples in a circular motion. I moaned softly, but viscerally.
“You’re wet.” Y said after unbuttoning my trousers.
I looked down and saw my briefs wet with precum, my trousers bunched around my ankles.
R, still behind me, lifted my t-shirt off my head, and started to rub his cock against my buttocks through his trousers. It felt good. I stood near-naked in the centre of the room, and my moans were getting louder as the pleasure intensified.
Y got on his knees and started to pull my briefs off, my hard 5.5-inch cock bouncing as it was caught under and then released by my waistband. I didn’t quite know what to do next, but this was the horniest I had ever been – I looked at Y, mouth slightly agape as he started licking my shaft from bottom to top.
A long trail of precum stretched from the tip of my cock to Y’s tongue. After repeating this a few times, Y placed his entire mouth over my penis and started sucking it enthusiastically. R stripped down to his briefs, revealing an average body with a flat stomach, and a large bulge – he looked intoxicated with lust. He started kissing my chest and moved to suck gently on my right nipple. One of his hands started tweaking my other nipple. It felt amazing, receiving a blowjob, and having my nipples played with by two men simultaneously.
After a while, R told Y to stand and remove his clothes. R then got on his knees and began sucking me off. In the meanwhile, Y obediently removed his shirt, trousers and boxers to reveal a 6-inch penis, hard and throbbing. He looked amazing, his body taut and hard, his nipples erect from arousal, and his cock a deep purple. He walked over and kissed me, my hands finding his uncut cock and rubbing the foreskin back and forth gently to find it wet. He moaned into my mouth as I toyed with his cock.
R removed my hands from Y’s cock. Kneeling between the both of us, he started alternating his lips between my cock and Y’s. Y and I, standing next to each other, continued kissing. Our hands explored the other’s body – Y groaned loudly as I pinched his tits gently, and I realised his nipples were as sensitive, if not more so, than mine.
R did a fantastic job servicing us both. He played with our cocks with his hands, used his tongue to caress the head of our cocks in small swirls, and paid our balls attention – he licked mine gently from time to time, and it felt pretty fucking good.
We kept this position for about 5 minutes. Then, Y asked R to stand, and pulled off his briefs. It was the first time I had seen R’s cock. It was the same length as mine, but maybe with slightly less girth. It was fair and pink, and his pubes had been trimmed and neatly groomed. His cock was turgid and twitching. Y and I then both got on our knees to repay the favour – as we started working on R’s cock and balls, our tongues meeting from time to time, R placed his hands around both our heads.
I placed my tongue on R’s cock, sucking someone off for the very first time. I looked at R to see how much he was enjoying himself. R was more than a little gone by this time: he was playing with his own nipples, smiling, and gasping in pleasure through his groans. My cock stiffened as I saw how much he enjoyed himself.
R then lay down on my bed, propping himself up with pillows under his back. His legs were open wide, his cock slicked wet in a mixture of precum and saliva. He asked me to lie on him, my back against his chest, so I did.
My legs dangled off the edge of the bed. Y straddled me and started to rub his cock against mine. We didn’t even need any lube – we were so turned on that our precum spilled freely. My head rested on R’s shoulders, and R again reached his hands around to find my nipples. (I think my moaning whenever my nipples were touched must have clued him in.) Whenever it felt particularly good, I turned my head to kiss R, my body shuddering with pleasure.
With Y rubbing his cock against mine, R gently teasing and pinching my nipples, and my tongue in R’s mouth, I was pretty close to the edge. It wasn’t long before I came. I could feel my balls tighten and my body tense, and I could barely make out the words “I am going to cum” over my constant moaning before my cum spurted out with so much velocity that some of it flew over my shoulder.
After I came, I moved a little so R could extricate himself from behind me.
R went on to kiss Y, who was still straddling me. R’s lips slowly moved south – he started kissing Y’s neck and chest before settling on sucking his nipples as his right-hand jacked Y off. Y, who was by this point pink not just in the face but also in the neck and chest, was aroused as fuck. It must have felt amazing because Y started vocalising (perhaps even involuntarily) – he kept telling R not to stop and saying how good it felt. His eyes were unfocussed, and at times they rolled into his head. It didn’t take long before he whispered softly but repeatedly “I’m cumming”. He exploded over me, bathing my chest in his cum.
That left R, who then took Y’s place by straddling me – apparently everyone’s favourite position that evening. It was Y’s turn to play with R’s nipples as R masturbated himself – I gently held R’s balls in my hand and played with them. R’s strokes started gentle and became more and more furious. It didn’t take R very long, given how horny he must have been by this point before he started yelling “FUCK” and unloaded over my chest.
The evening ended with me wiping the cum of three persons off me. We each took turns to shower – thank God for ensuite student rooms.
We tidied up after that, and then they left for the night. I was definitely in a state of surprise, not quite expecting the evening to turn out this way. I am not sure if R and Y had planned this, or if R was trying his luck to see how far we would go, given that parts of the night had seemed quite spontaneous.
We never had a threesome again, and I never saw R naked again – I never had anything for R, and what happened that evening was probably driven by alcohol and hormones. R and I remained close friends to this day, although I didn’t see Y again after university (R and Y had a falling out shortly after graduation, and I never asked R why). I hear Y got married and now has a 3-year-old – so maybe he was bisexual after all, and kept to a conservative decision in the end.
To this day, I think of my 21st birthday fondly. Not everyone’s first time at sex involves a threesome, and not everyone’s first time at sex works out this well, and for that, I’m thankful.
