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 and deftly undid my bra clasp with a snap. I shrugged my shoulders out of the loops and threw the bra off.

I had great tits, round, smooth, and each as big as my head. I often remind myself how much I love having Indian genes. Now they hung free in front of him. Brian pulled the blankets down enough to gaze at them in the moonlight. I rolled slightly on to my back so they spread against my chest. Brian slowly, tenderly, palmed them in his hands awestruck, weighing them carefully before putting my left tit up to his mouth and slowly running his tongue around in ever smaller circles until he reached my nipple, which he placed entirely in his mouth and sucked sharply. I arched my back and let out a sigh. He only sucked harder, as if trying to suck milk out of me. As I moaned in pleasure he reached his hand down past my waist, where he slipped under my flannel pants and caressed my round hips. Eventually his fingers found their way under by panties and between my thighs to my pussy. I shifted my legs to give him access, and he prodded my lips gently, slipping his fingertip between them briefly and running it along the inside rim, my juices flowing with the sensation.
Although it felt great, I didn’t come to Brian’s room to get fingered, I came for his cock. I pulled my nipple from his mouth and kissed him deeply. When we broke apart, I broke the silence.

“Are you ready to fuck me?” I bit my lip a little, imagining that thick cock thrusting inside me.

“Yeah, I’m ready, baby. How do you want it?”

“Well there’s one more thing. This is my first time. I broke my cherry a while ago but you’ll be the first guy inside me.” Brian’s face had a mixture of wonder and fear, I guess that was a lot of pressure to put on him.
“Is that okay?” I asked. He regained his composer when I spoke.

“Yeah, that’ll be great. I hope I live up to your expectations.”

“Oh you will.” I laughed a little, nervously.

“In that case, roll onto your stomach.” I complied quickly. I was okay with him taking me from behind. It’s not exceptionally romantic, but it is hot. Brian shimmied out of his pants and boxers, then swung his leg over mine. The blankets were completely tossed aside, but we were making our own heat now. He grabbed my hips, and lifted them so my ass was sticking into the air. Brian slipped his fingers into the waistband of my panties and pulled them down with my pants.

“Ready?” He asked me. I gave a noise of agreement. I felt his tip slide between the folds of my pussy and stop after an inch. It felt good having him inside me, pulsing with heat. He slid another inch and stopped.

“God, you’re so tight!” He went another inch deeper. I bit my lower lip at the sensation. With every inch I felt waves of pleasure as my virgin depths opened to him. Another inch. Another inch. Another inch. His dick bottomed out; I could feel his head against my cervix.

“That’s as deep as I can go. Does it feel good?”

“Oh yes!” I almost screamed back.

“I’m going to start thrusting, I’ll take it slow at first but get faster. Your pussy’s so tight though, I probably won’t last very long. I’ll pull out when I cum.” I was disappointed at that, but understood. Brian’s cock pulled out, then eased it’s way back in. I groaned. Out and in again, gaining speed like he said he would. Soon Brian was pounding my pussy so hard I had to grab onto the rails of the headboard to steady myself. My ecstasy climbed and climbed as Brian went faster and faster. Soon I couldn’t stop myself from screaming.

“Yes oh yes Brian, pound me.” I cried out. “Harder baby harder. Oh God. I’m almost there, Oh yes Oh I’m gonna CUUUUUM!” I yelled just my orgasm broke. My cunt went into spasms around Brian’s cock as it plunged into me over and over. I buried my face in a pillow and moaned at the top of my lungs. My hands squeezed around the rails until my knuckles were white. Brian moaned as my Kegel contractions drove him overboard.

“I gotta blow now babe. Gonna cum all over you.” Brian gasped. He pulled out. I heard him grunt and his wet and sticky sperm landed all over me from the fringe of my black hair to the small of my back. Even coming down from a massive orgasm, Brian’s hot jizz on my skin just turned me on again. Brian was breathing heavily somewhere behind. A few more drops of semen dripped off his penis head onto my still-raised ass; this guy could really cum.

Brian dismounted from behind me and flopped down on the bed, still panting. I relaxed my hips and turned my body to stare at his toned form, awestruck. He matched my stare, and I sank into his emerald eyes. This wasn’t right. I know I just did something wrong on my first time. He’ll never want anything to do with me again. I got in here by being a woman, but now I felt like a lovesick girl. I was struck by one last mad plea.

“I want you to fuck me again. I want you to cum inside me and I want to look right into your eyes as when you do it. I’ve been waiting months for this to happen and even if you never want to screw me again I just want you to do that.” I probably looked pathetic, begging for a guy to cum in me, but I needed this. All this longing and I couldn’t just walk away with cum on my back. I needed something meaningful.
Brian stretched out his and ran his strong hands through my hair, just watching it flow through his fingers. He looked into my eyes and said the greatest thing anyone had ever said to me.

“Are you sure you won’t get pregnant?”

Okay maybe it wasn’t the rom-com line some women imagine, but coming from my sweet, kind of dense Brian, it meant he wasn’t going to desert me. I was tangled up in my own mind; worried over some pointless insecurities. All he wanted was to not get me pregnant, which was reasonable, all things considered. His response was such a relief I broke out laughing. Brian was beyond confused. I managed to suppress my laughter long enough to respond.

“You’ve already came twice tonight already. You don’t have enough sperm left to get me pregnant. Besides, I’m off in my cycle,” I managed say before pulling Brian into a long kiss. I pressed my whole body against him and wrapped my arms around his neck. I felt so small compared to his height and muscles, but so protected. I didn’t let up until I felt his cock press erect against my thigh. “Up for another round, tiger?” I asked with a devilish grin.

“With you, Jess, I’m up for anything.” There was my rom-com line. Rolling onto my back I shot him my best sultry glare, that I swear made his dick grow another two inches. He crawled over and towered over me on his knees, smiling as he spread apart my thighs. He mounted me between my legs and tested my flexibility. My ankles wouldn’t quite go behind his shoulders but I was able to comfortably wrap my legs around his waist, tilting my hips up for him to penetrate me on his knees.

And penetrate me he did, hitting my bottom in a deep stroke that made me gasp. He kept the pace steady and quick. All I had to do was relax and enjoy the waves of pleasure with each thrust of his thick shaft. Relax and gaze at the Adonis pounding me with all his strength, propped up on his arms on either side of me. I grabbed my tits and massaged them slowly but firmly, giving Brian something to look at. My nipples were hard so I pinched and tweaked them, sending pangs of pleasure to my brain. Brian seemed to be altenating his stare between my face and my jiggling mounds.

“Do you like my titties, Brian?” I teased. Brian nodded but couldn’t respond with the effort necessary to maintain his tempo. I pushed them together and up, staring down at the deep cleft that created, then let them fall back to me, bouncing on my chest with a pleasing slap before resuming my massage. “Do you want to suck ‘em, babe? Drink all my milk? Maybe someday I’ll let you fuck them. You can slide your cock in between my sweet tits until you cum all over my face.” I could tell this was driving Brian crazy from the look on his face. “Or maybe you just want to cum all over my chest. Just imagine how my boobs would look covered in. your. cum.” I drew out those last three words and felt a drop of pre-cum leak into my pussy as a reward. I was really enjoying myself now, and stopped to moan exaggeratedly.

“But you can’t cum there. I won’t let you pull out of me.” I squeezed my legs around him gently to emphasize the control I had. “You have to shoot you wad inside me, and you won’t do that until I tell you to, will you tiger?” Brian shook his head. Sex is mental. I had him in the palm of my hand until I told him he could blow his load. I layed it on thick, now.

“It’s going to feel so good when you finally cum isn’t it?” Brian didn’t even respond now, his eyes focused on my lips making the words and my tits bouncing softly. “I’m going to cum right when you fill me up. Your jizz in every one of my nooks and crannies, I won’t be able to take it! You want to cum so bad, don’t you? Maybe you do want to get me pregnant? Plant your seed and put a baby inside me, huh? Is that what you want?” Brian was biting his lower lip, and his breathing was labored and unsteady. “Well you can’t cum until I tell you to, remember? And I’m not going to let you until you’re looking me right in the eyes.” I reached a hand up to caress his face, locks of hair falling in front of his eyes, damp with sweat. He focused right on my face, right into my own soft brown eyes, and I could see how much he wanted me, his animal lust that was threatening to overtake him. What does he see in mine?

I took a deep breath and gave him the command.

“Now cum.”

Fireworks went off inside me. Jets of Brian’s seed exploded from his tip, filling every last crevice of my womb with sperm. Brian, gaze still fixed on my eyes, let out an animal roar as his cock plunged deep and held as he erupted. I had never felt anything like this. I came immediately, just like I said I would. Brian’s hot cum pushed me over the edge with every wave that came out of him. My brow furrowed and I gave a high wailing moan of sheer pleasure. My eyes swam with stars so much I could barely make out Brian’s face of pure ecstasy. My back arched like it was going to snap. My legs constricted around Brian’s waist like I was trying to kill him. I may have actually cried. To try and describe the beautiful feeling any more is futile.

Brian’s arms collapsed at last and he fell onto me, still gushing cum into my cunt. It spread out from my opening and covered my thighs, making them slick with jizz. I let my legs fall away from Brian, and he rolled off and panted on his back. I had barely regained control of my muscles, but had enough strength to grab whatever blanket I could and pull it up to me. I curled up alongside Brian, one leg stretched over him, one arm reaching across his neck, one heaving breast resting on his, and fell into a deep, beautiful, sleep.

More to follow

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