Bargain with Stepmom Pt. 01

Chapter 1

The aftermath of my late-night game session with my friends was everywhere. There were snack bags all over my room, and the computer monitor glowed a pale grey in the distance. There was a pile of sleeping bags on the floor, and, inside them, my friends. There was a subtle knock on my door, it must have been what woke me up in the first place.

"Come in," I said hoarsely as I searched from my glasses with my fingertips. I sat up slowly, slipping the black plastic frames onto the bridge of my nose. On the floor the two sleeping bags stirred as my friends, Chris and Dustin, slowly woke up. The door opened slowly, flooding my room with light as my stepmom, Jen, stepped into the room.

"It's almost noon," she said matter-of-factly. She stepped over Dustin's sleeping bag and stood by my bed, her hands on her hips. She wore jeans and a tank top with wide, horizontal stripes. I tried not to stare, but the stripes outlined the curve of her ample breasts. She was thin, with an athletic build, but she had spectacular tits. I know I should not have noticed, but hormones dictated otherwise. "I know it's Saturday, but I'm not letting you sleep all day."

"All right," I said, throwing my hands up in mock surrender. She laughed. Behind her Chris and Dustin sat up, shaking their heads and slowly waking up.

"Can you boys clear out early?" she asked kindly. She then leaned in closer to whisper in my ear. Her short hair flopped in front of her eyes and she brushed it aside as she spoke. "Laura's coming over to use our shower. She has repairmen working on her water lines. I don't care if you stay, but thing one and thing two have to go." As she leaned in to whisper I stared at her cleavage, at the tan bra that pushed her tits together, for as long as I dared. She stood up and left swiftly, saying a kind goodbye to Chris and Dustin. When I looked over at them, they were grinning.

"What?" I asked.

"I was just checking out your stepmom's ass," Dustin said in a whisper. "So, so nice, my friend."

"Shut up," I groaned. This was a perennial topic. Chris and Dustin had been my friends forever, and they had been ogling Jen since we had discovered girls. When my dad passed away when I was twelve, Jen and I were the only family we had, and I found my friends' newfound lust for her disturbing. Over time, I got used to it. And one day, out of the blue, I looked at her and something primal stirred inside me. It was summer, when I was fourteen, and she was bending over, looking for something in the refrigerator. I remember getting hard, my face flush at my instinctual reaction.

At first I avoided it, then wallowed in guilt over it. She was my stepmother, and while my father had married a much younger woman, I felt guilty over my attraction to her. Finally I looked at it as biological instinct, that it was normal to appreciate a woman with a body like hers. And now, in my last semester of high school, it was second nature for me to appreciate the view.

Dustin and Chris left, but not after making a few more comments about Jen. It aggravated me, even though I secretly agreed with them. From her blue eyes, to her freckles and short, curly, sandy-brown hair, she was adorable. Part of me was aggravated with them for being so immature, and part of me was territorial and jealous that they were even looking at her.

Jen was downstairs in the kitchen when I headed down to get some food. She looked at me and smiled as I grabbed some breakfast.

"I'm going to be gone for a while, I've got things to do until around four today," she said casually. "Can you let Laura in, and stick around if she needs anything?"

"Sure," I said. I liked Laura. She was my mom's closest friend. They met in our church singles group. While Jen was tall, slender, with a knockout chest, Laura was shorter, curvy, with enormous tits and a big ass. She wasn't fat but was built like a renaissance statue. The idea of her stopping by did not seem like a bad idea to me.

Laura rang the doorbell shortly after Jen left. She was waiting, gym bag under her arm, as I opened the door.

"Hey, Steven," she said as I let her in. "Thanks for letting me use your shower. This no hot water thing is torture."

"I bet," I said, getting a decent look at her bubble butt. She wore sweatpants and a zippered jacket, her hair in a messy bun that cascaded into loose curls. Her jacket was loose, and she was clearly disheveled. Her jacket was unzipped partway, revealing considerable cleavage. I wasn't sure if she was aware how much she was showing.

It was clear she had nothing on under the jacket, and I felt my dick growing in my shorts, threatening to draw attention to itself.

"I look like a mess," she said apologetically. "Sorry."

"You look great," I said, feeling myself blush. She smiled, and I struggled to keep my eyes off her tits.

"I thought I might use your mom's bathroom, if that's fine with you," she said. "But she mentioned there's a trick to it."

"Oh, yeah, there is," I said. "The glass door latch is weird. I was supposed to fix it, but I keep forgetting."

"Can you show me?" she said with a smile. "I don't want to dump water all over her bathroom floor."

"Sure," I said. I led the way up the stairs and down the hall to Jen's room. She had the master suite, with a spacious bathroom and a glass-walled shower. "You have the lift the latch as you pull it, or it won't catch," I said, demonstrating it.

She nodded, and pulled her bun down, letting her long hair fall down her shoulders. She stepped past me and turned on the hot water, feeling how cold it was.

"It takes a few minutes to get hot," I said.

"Okay," she said. I noticed her zipper had moved a few inches down on her jacket. She definitely had nothing on underneath it. The zipper was now halfway down, and I could see the entirety of her cleavage. If it went lower, I'd see her belly button. I wondered if she unzipped it on purpose or it had just slipped down. We made eye contact and I was self-conscious about the erection straining against my shorts. I hoped she hadn't noticed.

She crouched down to dig her shampoo and lotions out of her bag. Her sweatpants rode low on her hips, and I could see several inches of her bare ass. I guessed that she had nothing on underneath. The idea that she was in such a state of undress made my dick ache.

"If you need anything, just call me," I added. She smiled, and I shut the door. I headed down the hall, sitting on my bed. I could feel my heart racing and my dick throbbing. I wanted to relieve the tension, but I was worried she might finish her shower before I was done. I was already really aroused, I didn't want to get even more so if she finished before I had come.

Moments later I heard Laura call my name. I stood up, adjusting my erection and hurried down the hall. I knocked, hearing water running.

"Come in," she called out.

I hesitated, but she called my name again, so I slowly opened the door. The room was flooded with steam, the mirrors opaque with fog. The shower doors were frosted over, but I could see the shape of Laura's nude body behind the blurry glass. I felt myself harden looking at her curves. This was the closest I had been to a naked woman. Even behind heavily fogged glass, the view was breathtaking.

"That latch is stuck, and my towel is on the counter she called out. Can you throw it over the shower wall, and then open this door for me?"

"Um, yeah, sure," I said, trying to keep my nerves out of my voice. I tossed her towel over the edge, sending steam swirling about her, revealing more of her shape as she shut off the water. She wrapped the towel around her midsection as I approached the door. The handle was slick from condensation, and I lifted the door slightly and pulled the latch. The door pulled open smoothly, and I stepped back to let Laura out.

"You're a real hero," she teased, stepping past me. She grabbed a second towel and wrapped her hair up in it. The towel around her body clung to her curves, her tits practically spilled out of the top of it. I took in the sights as long as I dared before turning to leave. I headed down the hall, my dick throbbing in my shorts. I was planning on jerking off the moment she started her engine downstairs. I sat at my desk, my mind tracing every curve, the line of cleavage that almost popped out of her towel, every inch of her. I was lost in my reverie when she knocked on the door frame.

"Hey," she said. She was leaning against the open door, still in her towel. Her hair was damp, falling around her shoulders. "You didn't have to run off."

"Oh," I said. "Sorry, I guess. I thought you'd want some privacy."

"No," she said simply. She stepped into my room. I turned my chair to face her. She walked right up to me, a look of determination on her face, laced with a grin. She was inches from me when she suddenly straddled my thigh. Her body was damp against the leg of my jeans. I had never been this close to a woman with this little amount of clothing on her. I tried to form words but before I could burst through my general confusion she kissed me.

As her tongue entered my mouth I was still trying to register what was happening. She pressed against me, the chair back falling back into the desk. My hands, on autopilot, touched her legs. I realized she was grinding against my leg, rubbing against my jeans, her breath coming in bursts as we kissed. I let instinct take over from the shock, and my hands slid up her legs, under the towel, and grabbed her ass.

She ground harder against me as I felt her ass with both hands. She threw her head back, the towel coming loose and showing most of her tits. I felt her body shudder as she came, her pussy grinding against my jeans. She kept rubbing, the towel slipping down more, until I grabbed the fabric with one hand and let it fall off her. She pressed against me, naked, grinding against my thigh as she buried her face against my shoulder. I gripped her ass harder and she rode me, until she cried out, her whole body tensing up and then releasing. She leaned against me, breathing hard, her muscles loose and her body still.

"Oh, god," she whispered in my ear. She sat up, finally giving me a full view of her tits and the triangle of bushy pubic hair pressed against my jeans. She got off me, a trail of her wetness dripping onto the wet spot she made on my jeans. She pulled me up, kissing me as I stood up. My hands found her tits as her hands slid down and worked my belt buckle. She deftly opened my jeans and reached down with her left hand, grasping my member and stroking it gently. She backed toward the bed, gently guiding me with the hand wrapped around my throbbing erection.

We were silent as she pushed me back onto the bed. She pulled down my jeans, stripping them off of me before climbing over me. She kissed me, her tits pressed against my chest, as the damp hair between her legs ticked the head of my dick. I ran my hands down her back, over her ass, gripping her gently as she kissed me. Suddenly, with a flourish, she sat up, straddling me. Her pussy dripped onto my dick in anticipation.

She took my erection in her hand, gently guiding my dick upward as she sank onto it. I could feel her pussy lips part as the softest, wettest, warmest sensation I've ever experienced took over me. She impaled herself on me, pausing as I slid into her completely. Slowly, almost painfully slow, she raised up and lowered herself, savoring the sensation as I filled her repeatedly. I was beside myself and gripped her ass as she started to ride me fast, grinding against me. Her tits swayed with the rocking motion of her hips, beads of sweat glistening on her stomach.

She came a third time, her pussy gripping me as her orgasm reached its peak. I gasped, thrusting upward like an animal, lifting her upward as I exploded inside her. She gasped as she felt my orgasm merge with hers, my dick pumping into her. She fell on top of me, laughing as our bodies gave in and a wave of pleasure overtook us both. I kept pulsing, filling her with cum as we lay there in silence. Finally spend, she crawled off of me, leaving a trail of cum dripping out of her and onto my thigh. She stood up, picking up the towel and giving me a view of her from behind. I was still on the bed, breathing hard, my first sexual encounter with a woman leaving my mind blank. She leaned over, tits heaving, and gave me kiss.

"I really needed that," she said. She looked me over as I lay there, panting. She bent over and kissed me, her tits dragging across my shirt as she moved lower and kissed the shaft of my dick. I was covered in her wetness and my semen, which spread over her lips as she kissed my flaccid member over and over. She ran her tongue up and down it, and slowly it came back to life. She then sat up, stroking me as she wiped her mouth.

"I guess I need a little more," she said with a giggle. She stroked me until I was completely hard, and then crawled onto the bed. She put her shoulders down, head to the side, and raised her ass in the air. She parted her legs slightly, and her pussy dripped a mixture of wetness and cum as she waited.

I got up behind her on my knees, my hands shaking a little from the excitement. The view was marvelous as I approached her. I slid the head of my dick against her labia until it popped in an inch. She gasped loudly, and I penetrated her fully.

"That's it," she said. "Go deep."

I obliged, thrusting into her. She was beside herself, her pussy tightening as I kept thrusting, my hips slapping her ass and making it jiggle. She came, crying out as I kept going, her voice deep and throaty as she moaned. I was self-conscious about all the noise, but no one was home, so I kept going. She came a fifth time, her pussy contracting even harder, and I finally lost it. While less intense, my second orgasm was still powerful, and I emptied what cum I had left into her as I pushed as deep as I could. I pulled out of her, my cum rushing out in a torrent. She sat down on the bed next to me, her chest heaving.

"The benefits of youth," she said sweetly to me as she kissed me on the cheek. I stood up, a river of cum running down her thigh. She wiped it off with the towel she had worn.

"See you later," she said sweetly, and left the room. Minutes later I heard her car engine, the need for me to relieve my sexual tension long gone. I lay on the bed for some time. I felt like my nerves were rewiring themselves; everything felt different. The bed sheets on my skin, the dried cum all over my dick, the air from my fan blowing over me; it was all new. Finally, after an hour, I sat up. My muscles felt like they had never been used before. I was figuring out a whole new sensory experience after having fucked—or, really, having gotten fucked by—Laura. I looked in the mirror, my dick slowly regaining some vigor as I played the morning over in my head. Soon my dick was throbbing, but the idea of jerking off so soon seemed like a waste. Instead, I got a new pair of jeans out of the dresser and headed downstairs.

When Jen came home I was reading a book on the couch. I had resisted the urge to jerk off but thinking about Laura all day had kept me hard and leaking pre-cum all over the inside of my jeans. She dropped her bag on the table and set next to me on the couch.

"Big day?" she asked casually.

"No," I said quickly, then added, "I mean, not really."

"Cool," she said, nodding. "Hey, Laura sent me a text; she says you were very sweet and helped her out."

"Oh," I said, "yeah. It was no big deal."

Jen shifted in her seat, turning to face me. She threw her legs across mine, something she had done a hundred times. I jumped from the contact, and she laughed.

"Why so twitchy?" she teased.

"No reason," I said a little too defensively.

"Alright," she said, waving her hand. She looked at me. "I just thought you'd be more relaxed."

"What's that mean?" I asked, my eyebrows furrowed as I tried to work out what she meant.

"Oh, nothing," she said dismissively. "What do you want to do for dinner?"

"Wait," I said, sitting up. She withdrew her legs and stood up. "What did you mean, you thought I'd be relaxed?"

Jen blushed, turning to the window to avoid making eye contact. I stood up, a feeling of dread rising up inside me. "Oh, you know," she said. "Just because, I guess, maybe helping out Laura wasn't such a bad thing...you know." She raised her eyebrows, leading me to the logical conclusion that she knew.

"I mean," she said, now talking from nerves more than anything else, "I'm not mad or anything. You're an adult, so what do I care if my friend comes over and you two...you know."

"You knew?" I said, my voice raising. "Did you know beforehand?"

"Um...yeah," she said, not meeting my eyes. In a low voice she added, "it was sort of my idea."

"What?" I said, my hands gesturing as I spoke. "You set me up with your friend?"

"I thought you wouldn't mind," Jen said. "I mean, I've seen you look at her."

"Yes, but didn't you think you should maybe ask me?" I said, my temper flaring.

"I don't know why you are getting so mad," she said defensively. "I mean, you just got some."

She hit a nerve. "Yeah, I did. But if I was a girl, and you were my stepdad, and sent one of your guy friends over to fuck me, would that be okay?"

I had hit a nerve in return, it seemed, because she threw her hands up. "Oh my god, I get you some action, while helping out a friend, and you flip out! I mean, she's been climbing the walls, needing it, and I thought you'd be more than happy to help. It's not like it was your first time, I'm sure."

I said nothing, and the realization crept across her face. "Shit," she said. "I thought...I always assumed by now you had..." She sat down. "I should have asked you first."

"Yeah, you should have," I said bitterly. "And now I can always remember that my first time was with my stepmom's best friend, because she needed to get laid and my stepmom lent me out."

My words hit her like a slap in the face. "I didn't mean it to be like this. I thought you'd enjoy yourself, get some from a hot woman. I didn't know it was your first time. And I should have talked to you first, asked you if you would have wanted to. I'll...I'll do anything to make it up to you. Name it, and it's yours."

"How about a blowjob?" I said, my voice full of acid.

I said the words to sting, and they did. The tears already welling in her eyes started to spill down her cheeks. She said nothing, but stormed passed me, rage etched in her features, as she grabbed her purse and left the house. I heard the door slam and I sat down hard on the couch, my heart hammering in my chest.

I had meant to hurt her with those word, to turn the situation around on her, but I still felt guilty for having said them. On one hand, I had enjoyed Laura, but I was still humiliated that my stepmom set the whole thing up. I bet Laura's shower worked just fine. I sat around fuming for a while, then went and showered for a long time. I thought about Laura but then I kept getting mad about Jen, and finally left the house to get something to eat. When I returned Jen still wasn't home. Finally, still mad, I went up to my room and played video games, trying to get my mind off of everything.

Around eleven at night Jen knocked on my door. I said nothing as she slipped into the room. She looked like she had been crying a long time. Despite what she did, she was my stepmom, the only family I had. My anger at having been set up ebbed, and I felt like I needed to offer an olive branch.

"Listen, about what I said," I began, but she interrupted me.

"I'll do it," she said, walking across the room and sitting on the floor across from me. When it was clear to her I didn't understand, she continued. "A blowjob. I'll do it. I humiliated you and...and it's fair."