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My Girlfriend’s Gay Brother

My girlfriend's twin brother's gay birthday celebration

I’d been dating Alice for about a year and a half. I felt like we were ‘the ones.’ It seemed likely that we would be getting married, have a family, and a long, happy life together. She’s a very caring individual, not to mention lovely, with her long black hair and curvy, southern Italian looks.

Alice has a twin brother, Kevin, who says he’s gay. I don’t think he’s ever been with a guy, or a girl, for that matter. The two of them are close friends, sometimes even finishing each other’s sentences. Alice tells me that when they were younger, they did play doctor a little bit, which may have something to do with her request.

As their birthday was coming up, I asked what she would like, hoping it wouldn’t be expensive. Oh, yeah, she and I are going to the same college, studying software engineering. We’re both quite good at it. A few months ago, we built a game together that has had 120,000 visitors, and many repeat visitors. The game doesn’t make any money, and our families aren’t rich, so we’re squeezing by on student loans that we’re hoping to keep small. But, I’m getting off track.

So, when I asked, I was relieved that she didn’t want something that cost money. But I was destroyed over what she did want. She told me about how her gay virgin brother has never been laid by a guy, and he wants it desperately. She wanted me to fuck him. As soon as I could talk again, I was like, “No fucking way!”

“Would you blow him?”


“Give him a massage?”

“Yuckky, but yes, I could do that.”

“With a happy ending?”


But I always cave for Alice, so I ended up agreeing that I’d give her brother a handjob. He, too was going to our university, but he was studying general science and chemistry. That made it easy for Alice and I to arrange a time and place to do the deed.

On their birthday, I had arranged for my roommate to be elsewhere for a few hours, then invited the twins over. Kevin, who is very tall, and shares his sister’s dark European looks, with somewhat longish curly hair for a guy, is not bad looking as guys go.

Alice and I were already there when he arrived, not knowing what we were planning, but that it was something special for him. We decided it would be fun to be as shocking as possible, so when he knocked, I stood behind the door and opened it carefully. You see, Alice and I were stark naked.

He came in, and gasped when he saw his sister starkers like that. When he took his eyes off her, his eyes went to my face, then immediately his gaze went right to my penis. I have no idea what he must have been thinking.

Alice explained the situation to Kevin. This was to be his birthday massage, administered not by her, being a woman, but by me, a guy, since Kevin was gay.

His eyes absolutely sparkled! “I’ve died and gone to heaven! You two are just absolutely too loving. Thank you, Thank you!”

Alice took control. She instructed him to take off his clothes and lay face down on my bed. Now I don’t know much about massage, never having had a professional one. Alice and I have played with the concept, but she knows as little as I.

I figured out that my hands should be warm, so I rubbed them together for a while as she dug out a bottle of massage oil. That probably cost her $10, a big sacrifice for her. I put some on my hands, then leaned in, and put my hands solidly on Kevin’s shoulders. It kind of sickened me. I figured I wasn’t very bisexual. Perhaps it wouldn’t do me any harm if I could be more accepting of the bisexual concept, but really! Geez! In fact, seeing that skinny, hair-covered ass of his added to the effect. I’d rather look at a car wreck. But, I’ll do anything for Alice…

I started massaging his shoulders, eventually working my way down his back, and his arms. I wasn’t sure if you’re supposed to massage someone’s hands or not, so I gingerly pressed my fingers into his palms. Already, he had been moaning about how nice it all felt, but when I pressed into his palms like that, he said it was “exquisite.”

The process wasn’t horrible. In fact, I was kind of warming up to it. I don’t know if it was because he was so appreciative, or what, but I was finding myself enjoying giving the massage. I went down to his feet, then worked up his ankles, calves, and thighs. ‘Should I touch his ugly ass?’ I was wondering.

I figured under the circumstances, it would be OK. I worked up his thighs, and then I did it. I let my hands rub the lower portion of his ass cheeks, being rewarded by another moan of ecstasy. I spent the next few minutes rubbing his butt. Occasionally, I’d kind of move my hands apart, and get a view of his asshole. It was hairy, but not terrible. I caught a glimpse of that sweet glandular smell that assholes can put out. It was the same as Alice.

Meanwhile, she had been sitting on my roommate’s bed. It wasn’t lost on me that she was totally naked. I could look over from time to time and see her marvelous tits, along with the rest of her. Perhaps I shouldn’t have been surprised, when after a while her hand went down to her crotch, and I could see she was rubbing her clit, as she intently watched me working on her brother.

As I continued to work his ass, my fingertips accidentally brushed the back of his scrotum a couple of times. The first time, that kind of bothered me. He seemed to like it, with an extra little ‘Hmmm.” The second time, it was kind of neutral. The third time, I seem to have brushed it on purpose. Go figure! I guess I did it for him, because he was enjoying it.

I hadn’t been paying the least attention to myself, so I was horrified when I suddenly realized I was erect. My penis had risen. I told myself it was because of Alice sitting there all naked and sexy. But was it entirely? The thought so scared me that I immediately focused my thoughts on something else. I tried to think of some recent PHP code I had been struggling with.

It was time for Kevin to turn over. He’d see my erection, but what could I do? Even though I was mostly facing away from Alice, she must have seen it also. When he did turn over, he looked right at it, and just wordlessly smiled. As he turned, I saw that he was fully erect also.

I massaged the front of him, ignoring that erection of his sticking straight up. It was quite a lot like mine, maybe a bit bigger, but surrounded with black hair instead of brown. Both of us are uncircumcised, but my head naturally pokes out a bit, and his was entirely covered.

The time came that I had been dreading. I was to give my girlfriend’s brother a handjob. We hadn’t told him it was to be anything more than a massage, and as Alice and I had arranged, if I simply couldn’t stand the idea of touching another guy’s dick, I could back out, leaving it as just a birthday massage.

I’m not like that. I couldn’t leave him there with an unrequited erection. I could imagine how I’d feel about that, if Alice did it to me. Imagine, getting a massage from your girlfriend, getting all hard, then not having sex, or getting sucked off, or something.

Again, I felt that slightly sick feeling in the pit of my stomach, as I finally wrapped my fingers around another guy’s dick. It had to be done, right? Now, it was interesting that it was erect like that. Kind of cool. I started stroking up and down, just like I do to myself. I felt him arching his back and tightening all his muscles. I realized if I let him cum immediately, it would be too soon. It would not be entirely satisfying for him. I stopped stroking him, and started playing with his balls. Remembering that I like it when Alice massages my balls fairly lightly, I did the same for him. I have to admit, feeling those balls of his squishing around in his scrotum, wasn’t half bad. I could understand while Alice likes massaging mine. He asked me to press harder, so I squished harder on his balls than I think I would have liked, and he was all moans of appreciation. My penis remained totally erect. I started to figure it must just be natural under the circumstances.

After a while, I turned my attention back to his penis, slowly stroking it up and down, determined not to let him cum too soon, so he could really get the most out of this. I had been determined that this would be a one-off, never to happen again, so I had to make it good for him.

I had entirely forgotten about Alice sitting on the other bed, until I heard her start to scream. I looked ever, and she was all contorted, with one hand rubbing her clit, and she was orgasming all over the place, barely able to keep her body on the bed.

That was too much for Kevin, who started to ejaculate all over my hand and my stomach. And, that, in turn, was too much for me. I started to ejaculate against Kevin’s side and butt, and my rock-hard penis hadn’t even been touched.

All in all, it was a satisfying afternoon, even for me, if I have to admit it.

Kevin was very appreciative, and offered to return the favor someday. I thanked him, knowing in my mind, that I would never, ever accept an invitation of that sort from a gay guy.

A week later, I was in Kevin’s dorm room, getting the blowjob of my life. I blew him too, something that I absolutely assured myself I would not do, yet I did it, and, I have to admit, I enjoyed it.

Of course I admitted to Alice what I had done, cringing at how she might react. She reacted with absolute joy. The only thing she regretted was not being there to see it.

Over the next months, she got her opportunity to watch. We did everything. Well, not everything. Kevin and I didn’t fuck, or even kiss, and he and Alice didn’t fuck, although she gave him a handjob, and he reluctantly felt up and sucked her tits. He claimed that he was still 100% gay, but enjoyed the feel of her breasts. When I saw him getting a handjob from his own sister, I had another spontaneous ejaculation. She and I are still very much together, and we are definitely going to get married after college. Kevin has found a boyfriend who takes up all his time. The guy is a way-tall guy on a basketball scholarship. Here’s the crazy part: I kind of miss my masturbatory activities with Kevin. I told Alice, and she’s totally understanding. She’s tried to make it up to me by giving me extra sexual attention at every opportunity. I’m so glad I jerked off her brother!

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