While You Were Sleeping

I wrote 50-some stories for Literotica over the past couple of years, as Gary X. November. That account suddenly fell out of the system, so I re-registered as Gary Alexander and I'm in the processing of switching over all my old stories to my new account (doing a good bit of rewriting along the way, hopefully for the better). All my old ratings are gone -- so if you read these stories "the first time around," please click onto them again and rate them again.

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Jimmy, Bob's college roommate, is visiting us for the weekend. We haven't seen him in almost five years, since graduation, and we had a lot of catching up to do. Dinner was fantastic -- Bob's the family chef -- and our preschooler, Davey, took to "Uncle Jimmy" instantly.

Still, it was nice when the little rugrat finally went off to bed and allowed the grown-ups to talk in peace.

It about one o'clock, we were all done for the night. I warned Jimmy that Davey was an early riser and might be bouncing noisily around the house at the crack of dawn. "Don't worry about me," Jimmy said. "Once I'm asleep, nothing wakes me. What? What are you smiling about?"

"Nothing," I said. "Just remembering when Bob told me that about you..."

...

It was during our final year at college. Bob and Jimmy had been roommates since freshman year, but this year Bob was spending more nights with me than he was with Jimmy. This one particular night, Bob realized he'd left a book in his room that he'd need early the next morning, and I went with him to pick it up.

It was a hot late-April night, and I was wearing a light sundress with no bra. Actually no panties either, but Bob didn't know that. Yet. Bob took advantage of my lack of bra by slipping his hand down my dress a few times while we were walking cross campus, and stroking my nipples. Honestly, I wanted nothing more than to get Bob's damn book, make it back to my room, and screw.

The door creaked loudly as we entered Bob and Jimmy's room. "Shhh!" I said automatically, and he said "Don't worry, once Jimmy's asleep, nothing wakes him." I could see Jimmy's silhouette in the near-dark, lying in his bed on the far end of the room. "Watch this," Bob said, and clapped his hands together so loudly that it made me jump. Jimmy never moved. "See?"

He flipped on the light. "I'm pretty sure it's on my desk somewhere," he said.

While he looked for the book, I glanced over at Jimmy again. Obviously expecting to be alone tonight, he was sleeping on top of his sheets, on his back, naked.I realized he must be having a nice dream. "Bob, take a look over there. Jimmy's dick is sticking straight up in the air."

"Jesus," Bob said, "I can really do without looking at Jimmy's dick. And you shouldn't be looking at it either."

I ignored him and walked over to Jimmy's bed at very gingerly sat down at the edge of it. He didn't stir.

"Will you get away from him?" Bob said.

"Come on," I said. "It's just so cute, standing up like that." I brushed against it with back of my hand. When Jimmy didn't stir and Bob didn't move to physically stop me, I circled Jimmy's dick with my hand. Now Bob was getting upset, so I told him to come over to me. When he was close enough, I unzipped his pants, pulled his dick out of his boxers, and began stroking it with one hand while I began to stroke Jimmy's dick with my other hand. "Please, Bob, when else will I ever get to stroke two dicks at the same time? And he'll never know."

Honestly, I don't think he registered a single word I said after I began stroking his dick.

This was all insanely hot, but I needed some attention myself. "These tits aren't going rub themselves you know," I said, and Bob dutifully unbuttoned the front of my dress and reached inside to give them a good massage.

I already knew what had to come next. When I thought Bob was moments away from cumming in my hand, I let go of both dicks, knelt at the side of the bed, and wrapped my mouth around Jimmy's. "Hey, wait a minute," Bob began, but then I shrugged the unbuttoned dress off my body, leaving it bunched on the floor, and spread my legs enough so that Bob could take me frombehind. I took Jimmy's dick out of my mouth just long enough to say "Fuck me. Hard."

"We don't have any condoms," Bob said.

"I don't care. Tonight I don't care. If you want my pussy, just fuck me."

His dick slid into me, the first naked dick I'd ever had inside me, and I came almost immediately. I loved the feel of it, and I'd been horny as hell for the past half hour at least. I continued sucking Jimmy as deep and as hard as I could. I wondered whether he'd be able to cum in his sleep.

I could tell Bob was about to, though. I let Jimmy's cock out of my mouth and said "In my pussy."

Bob didn't miss a beat fucking me as he said "But you're not safe."

He obviously wanted me to convince him to fill me with his cum, no matter what the consequences, and I wanted the same thing. "In my pussy," I repeated.

A moment later he came in my pussy. Hard. I couldn't be sure, since nobody had ever fucked me without a condom before, but I don't think I'd ever felt a load this big before.

I came a moment after Bob did, and then Bob pulled out of me and lay on the floor, drained (of both strength and, presumably, cum).

Jimmy, despite some of my best sucking, still hadn't cum.

I climbed onto the bed. "I hope you really will sleep through anything," I said softly as I crouched over him and slowly lowered my cum-filled pussy onto his still-erect dick.

I'm not going to lie: having a new dick in me after three years with Bob was exciting.

And I'm not going to lie about this either: at that point all I cared about was cumming one final time. If Jimmy didn't, well, he was asleep anyway. He wouldn't remember one way or the other.

I tightened my pussy muscles and Jimmy shot his load into my pussy which made me come hard. I eased myself off of him, watching his cum and Bob's drip out of my pussy onto his belly. Try to figure that one out tomorrow morning, I thought.

Bob and I dressed and walked back to my room (forgetting the book, by the way). We both felt a bit sheepish at first over what had happened, but we got over it quickly enough and we even used it as the basis for some fantasies over the years. We never told anybody about that night, and I'm certainly not going to tell Jimmy now.

In the five years since, I've been completely faithful to Bob, never touching another man sexually -- whether he was conscious or not. But I couldn't help thinking... Jimmy in the next room, and still nothing wakes him up once he's asleep...