Smiley Face

I had just gotten back from my Sunday morning run. My friend K., who happened to be my roommate for the summer while I was between leases before the start of the next year of grad school, was out with a couple of her girlfriends for Sunday brunch. 

She wouldn't be back for a couple of hours. So... 

I went into the living room and grabbed the rectangular decorative pillow off the couch, unzipping the slip cover as I went to my bedroom, closing the door behind me. I tossed the cover on the floor, the pillow on my bed, and quickly shed my shorts, socks, shoes and shirt, then pulled down the bedroom shades. In the now darkened room, I took my blue gel masturbation sleeve, bottle of liquid lube and Sharpie marker from the nightstand drawer, then flopped down on the duvet  Flipping the pillow over, I reached back to the nightstand for a few tissues, which I inserted into and then pressed to the bottom of the cylindrical hole which had been sewn into the pillow, with the assistance of the Sharpie marker. I then inserted the gel tube into the pillow, popped open the bottle of liquid lube, and squirted a good amount into the mouth of the tube. 

Not wanting to get lube (or anything else) all over M.'s fluffy, flowery duvet, I pulled the covers back and got between my own set of sheets which were underneath along with the pillow, rolled it and myself onto our sides, then reached down and placed my only slightly yet enlarging penis in the mouth of the tube, and gently pressed the head in. 

I closed my eyes as I took hold of the pillow, my penis hardening up before I even started to move and feeling wonderful as I then slid at first half-hard into the slick tube and after only a few gentle strokes felt myself almost at full erection. I adjusted my position as I began to thrust, and the tube slickened up nicely as my penis forced the lube along its length. Holding one end of the pillow against my chest with one hand, and using the other to press the pillow against me where I had entered it, I began to slowly and rhythmically f**k it. 

I didn't get excited nearly as quickly as I usually would. After my ten-mile run, I was pretty tired. Not too tired to "do it" of course, but that first time I did not yet know that if I kept my pace slow and gentle, having just come off my run, I'd be able to gently make it with my new contraption for far longer than I'd ever been able to last inside my little fun tube at any other time. So, hips gently pumping, eyes closed, my head resting on my own pillow, I lay there in M.'s bed and languidly f***8d K.'s throw pillow. 

It was probably ten or fifteen minutes before I felt a sudden jolt of pleasure in my penis and pelvis that told me I should slow down lest I cum too soon. But I didn't slow down. Instead, I pushed the bottom end of the pillow between my thighs, clamped my legs around it, and bear hugging it against me began to frantically screw it.  My excitement quickly mounted and as I felt myself nearing climax I rolled over on my stomach, the pillow under me now, me in missionary, my penis pumping in and out of it at the perfect angle.  I clutched it beneath me, holding myself up over it on my forearms, my chin just resting over the end of it as I looked in the direction of the headboard and the wall, watching it and it's contents start to shake, then hearing the bed start to squeak as it began moving with me as I continued to frantically screw the slick tube in the sturdy pillow beneath me. Before I really wanted to, not that I had any time to think about it, I quickly achieved an intense orgasm and came into the tube, feeling myself ejaculate in several long spurts, as the remarkable pleasure of my first orgasm achieved this way, and likely coupled with my depleted state after my run, made me swoon and my head swim as I came, first gasping, then sighing, then, finally, feeling myself still hard nd thrusting but no longer cumming,  I rolled over onto my back, still thrusting, upwards now, but quickly gave up, and rolling onto my side, again clutched the pillow with my thighs, bear hugged it against me, and just lay there, as my breathing slowly calmed and my penis, still fully hard, remained inside the tube and finally started to go soft. 

I awoke in my still darkened room, nude, the covers down at my knees, one leg and one arm draped over the pillow, my penis, now soft, still partly inside the tube. I could hear my roommate talking on the phone in the living room. It took me a couple of seconds to get my bearings. I quickly looked over to my bedroom door which, thankfully, remained closed.  I scooted back and slid out of the tube and sat up. Turning around to look at the clock, I saw it was a little after 2:00. 

I then saw the big yellow Sticky Note that had been stuck on the headboard, the smiley face written in Sharpie.

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The backstory, if interested:  A friend of mine M. had a summer internship out of the city, and my lease had come up in May, so we'd  arranged for me to sublet her apartment until the start of the next school year in September. I'd be living in her room while her roommate K., who was also a friend of mine that I'd known for about 3 or 4 years, had her bedroom on the other side of a common wall. We all knew each other pretty well at this point, so there wasn't really any awkwardness about K. and I sharing the small apartment.  

K. had an out-of-town boyfriend with whom she was on the outs at that time, while I was chronically single. And I had a pretty bad crush on K., of which she was aware. The interest was not reciprocal, and she had a boyfriend, anyway, so I wasn't expecting anything.

K. was also one of only a couple of my friends who knew I was still a virgin. 

It was a couple of weeks, on a Friday or Saturday night, before I woke up around 1:00 a.m., wondering why, and soon after heard a slight moan, or groan, from K's room. She moaned again, and I heard the bed squeaking as though she were rolling over or moving around. I knew she suffered from endometriosis, I'd actually gone to the ER with her one night a year or so ago, so my first thought was that she was in distress. As I wondered if I should go check on her and I sat up, her bed started creaking more rhythmically and the next few moans which came shortly afterwards were definitely NOT moans of pain. I was at once really embarrassed that I was overhearing her masturbating, not least because I was suddenly getting very excited and then I was reaching for my penis when she apparently climaxed with a louder moan and the end of the creaking and there I was in my bed holding my erection.

I lay back down feeling uncomfortable for starting to perv on her, but I was, of course, excited. After brief contemplation, my excitement won out and I quietly stroked myself, confident that she couldn't hear me, which I was sure she would not appreciate. I'd fantasized about her before, and imagining her naked, and touching herself, this night I reached my own climax all to quickly, trying to keep quiet as I shuddered and shivered, shooting all over my thighs and stomach. 

The following weekend we were both going to bed Friday night after not doing much that evening other than having a few beers with friends, and I brought her a cup of tea to drink while she read before she went to sleep. She was getting under the covers in her sleep shorts and top, and I saw that one of the big decorative pillows that usually rested against her headboard and the other regular pillow that were usually at the head of bed were now under the covers with her, sort of stacked atop each other, and laying lengthwise instead of across the bed. I stared at them for several seconds, honestly not understanding why she'd have her pillows in there with her like that. 

"What?" she said, apparently sensing my confusion, though I'm sure not realizing about what I was confused. 

"What's with the pillows?" I blurted out, before thinking about what I was saying. 

She looked at me like I was an idiot.

I looked at her. apparently, like an idiot. 

"Maaaasss-tur-baaaay-shun?" She said, drawing the word out.

I looked at her, probably blankly for second or two, then at the pillows and suddenly realized what I'd done.

I looked back at her, again, feeling...like an idiot, wondering how to apologize. I guess she still didn't think I understood. 

"I f**k the pillows."

"Oh, geeze I'm sorry, I wasn't thinking." I knew women, well, girls I'd thought then, humped pillows. I hadn't thought of grown women doing it. Really, I'd just never thought about it. I also realized then what she'd probably been doing the other night. 

"It's OK." 

"No, I mean, I shouldn't have said anything; I'm an idiot." 

"Well..."

"Yeah, I...do the same thing." 

"I'd imagine you do." 

"No, well yeah, of course But, I mean, with..." I realized that this was probably more than she wanted to know and stopped my mouth before I sounded even more foolish. 

"You f**k your pillow, too?"

"Uh, no. I...have a gel tube."

"A what?"

"It's like a soft tube you put your erection into ...""You do?"

"Yeah."

"Really?"

"Yeah."

"Cool. Can I see it?" 

"You want to see it?"

"Sure."

I came back with my little blue tube, and handed it to her. 

She took and looked at it, felt it, squeezed it, put her fingers inside it. 

"So what, you just jack-off with it?"

I hadn't actually thought of that. Well, I had, but...never tried it. Would that be less embarrassing than what I actually do with it?  Probably.

"I roll it up in a towel so I've got something to hold on to, and then uh..."

I was suddenly quite embarrassed. 

"You f**k it?"

"Yeah."

She looked at me, now clearly surprised. I thought I'd just really screwed up, and grossed her out. Instead she smiled, almost giggled. 

"Wow," she said. "I guess you have to lube it up, first?" She slid a couple of fingers back inside it.

"Yeah, definitely." 

"Because it doesn't feel very slippery."

"It is with the lube," I said.

She handed it back to me. 

"Kind of pathetic?"

"Why do you say that?"

'I don't know, having sex with a little piece of silicone?"

"I don't think so," she said. "I have a massager, so..."

"You do?"

"What's the difference? They're just toys," she said. "I think it must fell really good sliding inside that."

"Yeah, it does." 

I just stood there. 

"Soooo...any other questions?"

"Oh, uh, no."

"OK, go 'way now."

"Goodnight," I said as I started to walk out and she got under the covers with her pillows. 

"Goodnight," she said. 

I went to the bathroom and brushed my teeth then went back to my bedroom, got undressed, turned off the light and got into bed. I lay in the dark on my back for several minutes, wondering if I was going to hear her start to masturbate. 

I didn't. 

I don't know how long it was, not long. But I sat up and got the lube from the nightstand and propped myself up on a couple of  pillows and pulled my boxers down. I was already hard when I lubed myself up and then slid the tube down over my erection. It made a squishy squelching sound as I moved it up and down and I wondered if K. could hear it and what she'd think if she knew I was jerking-off with it right now and I didn't have much else to think about because I looked down and watched as the head of my penis "popped" out of the end of the tube as I shoved it down on myself and then it felt so good as the tube slid back up and slurped over my head again and I did that again and again and again and then I was cumming and I closed my eyes, tilting my head back and falling back into the pillows as I ejaculated, feeling it shooting up inside my erection, probably I thought, due to the tube clenched in my fist squeezing me so snugly. 

A couple days later she'd come into the living room.

"Have you had sex with my pillow?" K. asked.

I was sitting on the couch in the living room, holding one of the decorative pillows (K. had a lot of pillows, you had to move one or more of them to sit down...I guessed now I knew why).  I was actually wondering if K. had fucked it. But I didn't say anything. I hadn't.

"No." 

"Just wondering,.."

"I'd rather be in something.  I mean, if I'm not just using my hand."

"I guess that makes sense for a guy," she said. 

We didn't say anything else about it. 

We came back from a party Saturday night. 

"Tea, please."

"Yeah, OK," I went into the kitchen. 

When I brought it into her bedroom she was already dressed for bed. She took the mug of tea from me and then knelt down and lled something out from under her bed. It was the decorative pillow from the couch. 

"I think this will work," she said, as she took the slip cover off. She tossed the cover on the bed and flipped the pillow over. About 2/3 of the way from one end, or a third of the way from the other, there was a hole in the pillow. Not a rip, but a hole, all sewn up neatly like it belonged there. In the hole was my gel tube, it's lips just emerging a half inch or so above the surface of the pillow. I took the pillow from her. The hole wasn't straight in, but made on an angle, so when the pillow laid flat, my penis would slide forward, not just straight down. 

Good for thrusting.

"Better than wrapping it in a towel," she said. "Just remember to put some tissues in the end of the slot to catch your load when you cum in it, OK?"

"OK."

"Or maybe a baggie around the end of the tube, I don't know; but something to catch all the cum." She leaned over and got the slip cover. "When you're done."

"Well, uh, wow, thanks." 

"Well, you're welcome.'

I just looked at her, not knowing what to say. 

"OK, go 'way," she said, and shooed me out of her room.