Keep Me Warm in the Winter- Part 1: Fantasies

Keep Me Warm in the Winter- Part One: Fantasies

“Be home by 6, Jess. Mom is making dinner,” Brian said over the phone.

It was weird to hear Brian refer to Mrs. Michaels as just “Mom”. Not “my Mom” which he usually used. That was new. Didn’t help me get any closer to having sex with him though.

When my dad got transferred to the middle of nowhere, my parents thought it would be fine if I stayed in Boston and finished my last year of high school with all my friends. That was in October, and I had loved every minute of being away from the mass of children, and, of course, sharing a house with Brian. His family had a pretty large house and he had one sister, younger by a few years. I, and my family, had known Brian ever since we’d met in 3rd grade. Even as he became a bit of a jock, popular with everybody, and I became a nerd, we still managed to stay close friends. That’s why my parents trusted us two horny teenagers to live in the same house together.

For the first month I thought they’d figured it out. Brian was like my brother, and I could never do anything with him. But the next month I’d rethought my position. He was the same guy I’d known since I was a kid but that didn’t make him any shorter, or get rid of his sandy blonde hair, or strip away the muscles he’d gained through years of lacrosse… Compound that with seeing him walk around shirtless, in boxers, or steamy coming out of the shower and I was over the moon guy. Under the cover of darkness I would reach down and stroke my clit until I writhed in ecstasy on my bed thinking about all the things he could do to me with what lay between his chiseled thighs.

I had to hope he noticed me too. There was some evidence in my favor: boys, longtime friends or not, had been pretty hot for me since I’d first sprouted breasts back in 8th grade. I got wide hips and a narrow waist to go with them. I was only 5’2”, so I’d managed to avoid attention through most of high school by wearing baggy sweatshirts and not drawing too much attention. After a while the stares become more of a nuisance than a compliment.

He’d had more experience than me, though. I’d had a few boyfriends in high school, but they could never merit more than a half-hearted hand job in the backseat of my Thunderbird. Brian had a host of girlfriends he would smuggle into the house to fuck and then shuttle home just as secretly. Once in a while I’d hear them through the wall separating our bedrooms, and feel pangs of jealousy. Why? I’d ask myself. Why would he want a desperate virgin like me when he could have any woman he wanted?

So that’s why I felt so down as I sat across from Brian eating spaghetti with his family. I wanted him, but I knew I could never have him. Classic, really. His sister couldn’t stop blathering on about whatever boring things happen in the lives of 15 year olds, and his parents appeared disinterested. The desire to rip off the rest of my shirt at dive at him over the table was stronger than usual. Hm. Outside, snow fell slowly, illuminated in the street lights.

Afterwards the family retreated to each member’s usual corner of the house. I studied derivatives at my desk, even though I didn’t have school tomorrow. I waved the white flag of mathematical surrender and went to bed around midnight. I lay in bed for what seemed like three hours, unable to rid my mind of a shirtless, erect, Brian, standing in the shower giving me a “get in here and grab your ankles” look. I gave it 15 minutes in real time before I couldn’t take it anymore.

I could either lay in here or suffer in silence or I could move on. There was a third option… I didn’t need to run away from Brian like I was afraid. His room was two feet away. I was a modern woman and I could take the first step. And I could take what I wanted. A smile crawled across my face and a plan hatched in my head. Step one: get into Brian’s room under seemingly innocent circumstances. Step two: Fuck him. It was really more of a loose outline.

I crawled out of bed. It was freezing in the house outside my small mountain of Blankets and comforters. I figured I’d work this in. I took off my flannel shirt and shivered in my bra for a few seconds while I found my bathrobe and slippers. I put them on quickly and crept out the door and a few feet to the left. I softly rapped on his door a few times, then a few more until I heard him roll out of bed and come to the door.

“What?” he whispered.

“It’s Jesse. I’m cold, do you have an extra blanket?” A short pause followed.

“Yeah, come in.” He opened the door just enough for me to slip through then shut it. His room was a mess, but in that orderly way. Everything is in its proper place, but sometimes the proper place just happened to be on the floor under the desk. As Brian turned to go look for a spare blanket I followed him closely until he reached the bed, then sat down on his trunk as he looked. I adjusted the neckline of my robe enough to show more cleavage than I’d worn in years. I coughed lightly, enough to get Brian to turn and glance my direction, but he resumed searching his pile of linens in short order. No dice
An alternate course of action took shape in my head. These were extraordinary circumstances, and they merited extraordinary measures. I threw my robe behind me and climbed under his sheets. The bed was still warm where he had been lying, and the covers smelled like musk. Brian turned around when he heard the rustling.

“What are you doing?” he asked, obviously beyond puzzled. Not every day does a scantily clad woman climb into your bed apropos of nothing. Well it had at least gotten me somewhere.

“It’s freezing in my room! Why I don’t I just sleep here for the night?” I cooed. Brian shrugged and looked exasperated.

“Fine, I’ll just go sleep on the couch.” I bolted upright, haphazardly clutching sheets to my breasts.

“Oh no, you don’t have to! You can just stay on that side of the bed.”

“Don’t you usually wear a shirt to bed?”

“I usually sleep naked.”

was really getting the hang of it now. Brian stared, his mind vaguely grasping at a plot he couldn’t quite grasp. He responded warily.

“Sure, that’s all right, we just can’t let on to the parents.” He walked over to the other side of the bed in his thick fleece pajamas and crawled in. His loose pants let me get a good look at the mound in his pants. Apparently that old Jesse Patel magic was still working. “Good night, Jess,” he said and turned off the lights. Though the lights were off, the reflection from the snow outside lit the room in a dim, white glow. I rolled over, but stayed awake. Now it was all about waiting. I’d turned him on, now to stay awake until he thought it was safe to finish the job. I knew a thing or two about teenage boys.

I stretched and settled into the soft, warm bed. It was much warmer than sleeping alone, so at least my pretense wasn’t a complete deception. I hummed contentedly, this was all going perfectly.

It was after half an hour of feigning sleep, breathing deeply, lying still, that I heard Brian stir on his side of the bed. He had climbed in with his back to me, and I had my back to him. After a few seconds of adjusting, a soft, velvety rustling came from Brian’s half as he stroked himself. I smiled that my plan had worked so well. It was cute, really, hearing his fitful exhalations. I just hoped he was thinking about me.
Now was the zero hour, I was just a few steps away. Alright Patel, bring it home . I let him carry on for a couple minutes before I interrupted; I couldn’t have him waste his cum, could I?

“Need any help with that?” I purred into the pillow. Loud enough to be heard.

“I wasn’t-“

“Hey you don’t need to explain yourself, but why don’t you just let me help you out with that?” There was a long pause, I could practically hear the gears turning in his head.

“You want to…”

“Well why not, you’re thinking about me anyways right? So point that cock of yours over in my direction and let me take over for you.” Brian rolled over as he began to speak.

“Really? You want to jack me off?” Excitement was leaking into his voice now.

“That’s exactly what I want to do,” I purred, and rolled over myself to face him. I shifted my body about a foot closer on his queen sized bed and reached under the covers to his cock. It felt thick and long. Hard as a rock. Brian gasped when I touched it. I was so much shorter than he was, I had to slide down almost under the blankets entirely to get a good angle. When I found a good position to stroke in, I set to work. My hands are small, soft and nimble. I had done this before, so I knew how to work it: dancing across him, gently squeezing his tip, and caressing his balls seemingly all at the same time. Soon I felt a glob of semen drip out and onto my fingers. I was experienced enough to know what pre-cum meant.

“Oh God, I’m going to cum,” Brian groaned.

“That’s the idea,” I giggled from under the sheets. I shifted my focus to long pulls up and down his shaft with one hand while fondling his sack gently with the other. About ten seconds I felt his hips draw away from me and his cock prepare to fire.

“Here it is, here it comes!” I said in gleeful anticipation. Brian writhed on the bed in ecstasy. His seed flew across the bed to my bare stomach where I felt it land, hot and wet, in long streams: white against my chestnut skin. Brian’s cock continued to twitch. Some cum landed on me, all the way up to my bra strap, while some just oozed out to collect around my curled fingers as they milked him for every last drop. Brian caught his breath slowly.

“Christ Jesse, that was…”

“Amazing?” I suggested.

“Something like that.” He wrapped one of his strong arms around my narrow waist and pulled up close to him. His lips locked around mine and he sucked me into a deep, passionate kiss. His tongue probed at mine and his muscled body radiated heat like an engine. I came up fro air, smiling.
“Now let’s get this back in action so we can play some more.” I reached down to touch his heavy, uncircumcised dick, still sticking out of his waistband.

“Yeah?” he replied with an audible grin. “I think we can do that.” As we separated slightly I felt the a few gobs of cum on my stomach peel away and stick to him. He wiped it off himself and stared at it in the moonlight.

“Wow, I really came,” he said. I nodded playfully. “Let’s get this off of you,” Brian whispered into my ear as he made a move for my bra clasp. I swatted his hand away, then ran my own up his shirt to feel his hard pectorals.

“Yours first,” I said. Brian didn’t hesitate in sitting up to rip off his fleece shirt and throw it off to the side of the room. As he lowered himself back down, my fingers played over the ins and outs of his athletic body. He moved his hands to my back ...

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