"Okay, let's talk about that."
In the darkness of our dorm room, lit only by such light as filtered through the blinds from the quad outside, I climbed out of my own bed and sat down on my roommate Bob's bed. We'd both turned in maybe half an hour before, but had kept talking instead of sleeping.
"Okay."
He sat up under the covers, throwing his legs over the side of the bed, and I scooted next to him, casually draping an arm over his shoulders. This was as forward as I had ever dared be with him, so I was kind of nervous, even though I was absolutely convinced he was gay too. He didn't seem to mind, anyway, and it felt good being up against each other there.
I'd had my eye on him ever since freshman orientation two weeks earlier. He was tall, thin, and blond - something I've always been partial too - but he also had a beautiful smile, and he smiled almost all the time. (I learned later that someone once told him that people like you better if you smile, and I think he overdid it a bit.)
"By the way, I think you should lose the pajamas."
He'd been surprised to learn that I slept only in my underwear, much as I'd be surprised to learn that at 17 he still slept in PJ's like a little kid
"You mean right now?" He giggled a little bit.
"Well, won't they get in the way?"
The thing that most convinced me that this boy was gay was a combination of the way he spoke and some of his mannerisms that struck me as effeminate. The fact that I, a champion high school swimmer, exhibited nothing like that behavior didn't affect my confidence that this was a good guide to homosexuality. In fact, only one of the boys I'd fooled around with in High School had really been anything like Bob, so I was really on thin ice here.
"Um." Pause. "You mean you want to do it together? Here?" Another nervous giggle.
For an answer, I started undoing his pajama top from the bottom with my free hand. He didn't stop me, but I felt him tremble a little bit. After a few buttons, I slipped my hand under and rubbed his smooth tummy. He rewarded me with a surprised little moan of pleasure.
After orientation, I had struck up a conversation with Bob, and, learning his temporary housing assignment, I'd arranged to spend quite a bit of time with him. We had a number of academic interests in common, and could talk endlessly. We explored the campus together over several afternoons, and talked a lot on those expeditions.
"We shouldn't do this," he said softly, but he made no effort to move away from me. I slid my other hand down from his shoulder to his waist, feeling his skin under my palm, holding him close to me. "But I have to admit it does feel really good."
You wouldn't have expected an athlete from a Tennessee prep school to hook up with a nerd from the Southern California public schools, but there was definitely something about him that really attracted me, and he seemed pleased by the attention. When we applied for permanent room assignments, we signed up as roommates.
"Yeah, it does, doesn't it?" I guided his hand to my own stomach. He rubbed it hesitantly. I continued unbuttoning his top.
We'd talked quite a bit about sex, but very little about girls, except to confirm that neither of us had been with one. Mostly, we'd discussed masturbation, and we'd mentioned homosexuality, but only in joking fashion. Our first night in the room together, we'd got onto the jerking off topic again, and he'd asked me if I ever did it in bed at night. That was when I got up the courage to walk over and join him in bed.
"This is giving me an erection," he whispered with some surprise.
"Me too." I pulled on his pajama top, and he lifted his arms and let me take it off him. "Have a look," I dropped my shorts and kicked them away, exposing my hard on.
"Wow! That's a lot bigger than mine." I guided his hand to it. He hesitated a bit, but then grasped it. (Bliss!) "This is like iron!"
I slid my own hand down into his PJ bottom and under his shorts, and gripped his own erection. I heard him inhale sharply as I touched it. He was right - not all that big - but I didn't mind. Not at all.
"Lift up so I can get these off you." He complied, and I pulled his PJ bottom and underwear down to his ankles. Then I put my hand between his legs and fondled his balls a bit before exploring his cock some more and finally gently stroking it. He had been just holding my cock, not doing anything with it, but now he got the hint and started stroking me too.
I had wanted this so long, and I was so tense and excited that he couldn't have stroked me more than 5 times before I knew I was going to cum, and although I held back as long as I could, by his 10th stroke or so, I was shooting on my stomach and chest as high as my nipples. He was a good trooper, and didn't stop stroking until I wordlessly removed his hand with mine.
From his breathing, I could tell he was getting close too - maybe watching me shoot had helped - and soon enough he squirted more modestly on himself and dribbled down onto my fist.
"Okay, stop." I let him go, then grabbed his PJ top from the bed.
"I know just the thing to use this for." I wiped my cum off my torso with it, then cleaned my hand and handed it to him. He seemed rather subdued as he cleaned himself up and then threw the garment in the floor. I put an arm around him, but he pulled away and tried pull up his bottoms and shorts from his ankles. "Hold on a minute," I said. He froze.
I straddled him on the bed, my knees on either side of where he sat bare chested, feet on the floor, bottoms and shorts still around his ankles. "Are you okay?" Again, he tried to push me away, but only weakly, and I pulled him to me, pressing his head into my shoulder, wrapping my arms around him. After a moment, he quit resisting and let me hold him.
I held him for a little while, stroked his hair softly with one hand, kissed him on the head and felt him stiffen in my arms for an instant.
"Lie back on your bed." I pressed him back onto his pillow, and he lifted he feet off the floor and straightened out in the bed. I pulled his clothes from around his ankles and tossed them into the floor, then lowered myself onto him, my crotch onto his, my face right above his. I looked into his eyes, but he was trying to look away.
"Kiss me, Bob." He looked back at me, his eyes opening in surprise, and then I saw just a hint of his trademark grin, and he lifted up and kissed me, quickly, on the lips. I leaned closer to him, and kissed him myself, chastely the first time, lifting back up and smiling down at him again, and more vigorously the second time, slipping my tongue between his lips. He made a small surprised noise as my tongue entered his mouth, but he didn't try to stop me, and after I'd explored his mouth for a bit, I felt him hesitantly try to slip his tongue to me. As we lay there swapping tongues, I grew hard again, and felt him doing the same.
"Ready for round two?" I pulled up and beamed down at him.
"Yeah, I guess so." He whispered softly. "What do you want me to do?"
"Will you suck me for a little bit?" I climbed up on my knees and slid forward until my dick was just above his mouth. He stared at it the way I imagine a mouse looks at a snake.
"I dunno." A pause. "Will you cum in my mouth?"
"Not this time. I just want to feel your mouth on it."
"Will you suck me too?"
"Absolutely." I leaned forward, touching the tip of my cock to his lips, which parted and let me slide it in. "Try to purse your lips over your teeth, okay?" He complied. "Yeah, that's good."
From this angle, there really wasn't much we could do. He had no leverage at that angle, so I took a few strokes, me fucking his mouth rather than him really sucking me, but it was obvious I hadn't thought this through, although I really loved watching my shaft going in and out of his mouth. After a bit, I pulled my dick out of his mouth and I heard him sigh deeply, as though with relief at being done with a difficult task.
"Thanks, man. That was nice." I worked my way back down and kissed him again. He was a bit more enthusiastic this time, and we kissed for a bit before I slid further down to where I was kneeling between his legs, with his cock in my hand.
"Okay, your turn now," I smiled at him and started licking his little dick, then sucking on it. No problem swallowing him all the way to the balls; even fully hard he just tickled the back of my throat. Then I let one finger slide down his balls to his crack and just touch his hole.
"Oh wow!"
"Do you like this?" I stopped sucking but kept lightly stroking his hole.
"Yeah, that feels very nice."
"Mind if I play with it a little more?"
"Okay."
I got out of bed, padded over to the sink, took a small jar of Vaseline from the cabinet, and climbed back in bed. I put some lube on a finger and start to gently rub his anus. He signed again, folded his hands behind his head and smiled at me. (God, I loved that smile!)
I fingered him for a while, slow and easy. I sucked him some too, but he warned me he was close, so I stopped. By then I'd opened him up for one finger and started on two.
"Is this going to hurt?" He seemed almost casual when he asked this, as though we'd somehow already both agreed completely on what we were going to do and there was no need for further discussion.
"I'll be very slow and gentle. How does it feel so far?"
"Feels real nice."
"Good."
Once I could slip two fingers into him, I lubed up my cock, which was now very, very hard. I was pleased to see that he was also very hard. I pressed the head of it against his hole and asked him how it felt.
"Nice. Real nice." I pressed a bit harder. "Mmmm. Even better." From my high school experiences (which included being a bottom) I knew that there could be too much of a good thing, so I very cautiously increased the pressure until I felt myself starting to enter him, then I let off just a bit so I was right at the limit, pushing as hard as possible without entering him.
"Oh yeah, oh that's SO nice" he whispered.
"Try to relax now. Pretend you're having a bowel movement in reverse." Okay, not the sexiest line - and not original either - but I felt myself slowly sliding into him without increasing pressure, and it felt really, really good on my dick.
Then suddenly I heard him hiss with pain, and I stopped pushing and slid back a fraction.
"You okay?"
"That hurt!"
"Sorry. It's hard to do it perfectly - especially the first time. Do you want to stop?"
"No. Maybe it's okay." He sighed deeply once, then smiled weakly at me.
"You sure?" He just nodded.
I resumed pushing, slowly and gently - it was so hard to take it slow though! I was exultant as I finally felt the flange on the head of my dick slide into him.
"Okay, the head is in, so it should be easier from here."
"Uh huh." He sounded dubious.
"You still okay?"
"Yeah."
I kept going very slowly as I felt the flange on my cock slide up his anal canal, loving the wonderful way it gripped me so tightly. When I felt it slide out into his rectum, I slide the rest of dick up there more confidently. I heard him yelp just a little as the last bit slid in and I felt myself hit bottom inside him.
"Pull your knees up onto my shoulders." He did. "That better?" He nodded. I leaned forward and kissed him on the mouth. He lay very passively and didn't try to tongue me back this time, but he did suck on my tongue.
"How you doing? Comfortable?"
"Yeah." A bit breathlessly.
"Good" I found his cock with my hand, and stroked him until he was erect again. Then I put my mouth back on his and began pumping his ass. Slowly at first, I picked up speed as I felt him loosen up more. With my tongue in his mouth, he couldn't tell me how he was feeling, but his arms around me holding me close to him told me all I really needed to know.
Since I'd already cum once, I pumped him for a while before I felt myself getting close, using a nice, long easy stroke - not too deep, and not risking popping out of him on the upstroke. Once I reached the point of no return, however, I started fucking him really hard and deep, and suddenly he pulled his mouth away from mine, pushed up on my shoulders, and panted "I'm cumming!"
By this point I was already shooting my load into him, and I lifted up enough to watch in amazement as he shot on his stomach without my having touched him.
I pulled myself out of him, still not quite believing this, and kissed him softly on the lips.
"That was really great, Bob. That was your first time, wasn't it?"
Then I saw the tears in his eyes.
"Hey, hey. It's okay. Did I hurt you?"
He just shook his head then let out one choked sob.
I lay down beside him and rolled him over onto my shoulder, holding him close to me.
"Go ahead and cry. I've got you."
And with that, the dam burst, and he sobbed openly on my shoulder, clutching me tightly. I lay there hoping no one walked by in the hall and heard him - especially when I remembered we hadn't locked the door. We also hadn't cleaned up, and I felt his cum running down my side and dripping onto the bed. I just held him tight.
After a bit, he quieted down, sniffled a bit, then took a long, ragged breath and let it out. I gave him a reassuring squeeze, and he settled down against me.
"Better?"
"Some." I heard him sniffle a little.
"I love you Bob." I felt him stiffen in my arms. "Really. I mean it."
"I'm a fag. You fucked me like a girl." He choked on the words again, "and I WANTED it." He started to cry again, quietly this time, but I noticed that he pulled himself into me for comfort, rather than trying to pull away. I stroked his hair absently.
"I know." He started a bit at that. "I'm a fag too. I don't like girls at all. I've even been fucked too - how do you think I knew what to do for you? It would have hurt a lot if I'd tried to just stick this thing in you, you know."
That provoked a short laugh - a laugh through his tears - and he sat up and looked in my eyes at though to see if I was lying to him, but I just smiled up at him. He grinned again, lay back down on my shoulder, and sighed contentedly.
"Will I get to fuck you too?"
"Sure, if you want to. Not tonight, though." We both giggled at that.
"What if I don't want to? What if I always want to be your . . . to do like we did tonight?"
"Then I'll love you just as much," and we hugged each other close.
We talked some more and drifted off to sleep in each others arms.
In all the months to come, we became very practiced at lovemaking - various kind of lovemaking, although he did always take the bottom role with me - but I never again managed to make him cum just from fucking him. As though the magic of that first time was something very special, never to be repeated.
--Swimmer