Bargain with Stepmom Pt. 01

"Jen, really, I didn't mean it," I said, not really processing what she was saying.

"No, listen to me," she said. "I did something pretty terrible. You're right, everything you said was right. Even if it wasn't your first time, it was callous of me just to assume you'd be ready to go, even if Laura said you didn't hesitate," she laughed, but grew serious. She paused, straightening her posture. "So, I'm going to give you a blowjob, as a way of saying I'm sorry."

"Jen," I said, "you're upset," but again she cut of me off.

"What I did was demeaning and unfair. So I'm going to do what you suggested. Maybe your dick in my mouth will make up for what I did."

I had never heard her talk like this. "You're serious, aren't you?" I said.

She nodded. "Yes, dead serious. I owe you a blowjob."

"Right now?" I said, as my voice cracked.

"No," she said, laughing. "In a few days. I need to mentally prepare for it."

"Then don't do it," I said.

"Oh, I'm going to do it. When I put my mind to something, I don't back down. But even though I owe you this blowjob, and I'm doing it willingly, you have to grant me a few days of processing what I'm about to do to my stepson, okay?"

"Okay," I said. She was tired and upset. I knew she didn't mean it, so I agreed to let her process things. Tomorrow, I was sure, she'd tell me she had not meant it, and I would tell it that it was all okay.

She stood up, smoothing out her wrinkles in her jeans. "And don't think I'm going to change my mind." She bent forward and kissed the top of my head, her cleavage in my face. My dick twitched to life, and then roared to attention as I thought about what she actually said. She walked out of the room, pausing to say goodnight before disappearing down the hall.

Chapter 2

I woke up late, having stayed up late thinking about the day's events. I abstained from jerking off, even though I desperately wanted to. I still expected Jen to come to her senses, or at the very least back out in a panic, but the idea of touching myself still paled in comparison to Laura fucking me or the thrill of Jen's suggestion. Even though I knew she hadn't meant it, the idea that she would even propose such a bargain was pretty erotic. I wondered, if she was serious, if I could go through with it. Less than ten seconds of contemplation told me that, yes, without a doubt, I could. I got dressed in the jeans Laura rubbed up against and headed downstairs. Jen was up, bustling about the house as she always did when she wasn't working.

"Good morning," I said, stretching.

"Good morning," she replied with a smile. "I'm glad you're not still raging mad at me. I'm really sorry about what I did."

"Let's not rehash it," I said kindly. "Thank you for apologizing."

She smiled back. "Thank you for accepting it," she replied. She came around the counter wearing a tank top and short khaki shorts. While Jen's tits were the main attraction, she did have a cute butt, which was rare on women as tall and slender as she. I appreciated her toned legs a lot and was glad to see her in shorts. My dick twitched, reminding me of her bargain. "I'm guessing you've come to your senses about the blowjob you offered me last night?"

"If you don't want one, then say so, because I've made up my mind and I'm going to do it. In a few days, if that fits your schedule." She laughed, tossing her bangs to the side with a flip of her head.

"Oh," I said. "I didn't think you were really going to ..."

"Suck your dick?" she said each word separately, letting the words hang in the air with a wave of her hand. "Of course, I am. I've never backed away from a promise, sexual or otherwise."

"Do you have a history of making sexual bargains?"

"No," she said simply with a shrug. "I mean, once or twice, sure. But never to gain anything. More often than not it's because I lost a bet or something. Like the time I made a bet with my friend in college. He'd been wanting and scheming to get me into bed for years. And we made a bet during the playoff game that his team would beat mine. The deal was that if my team won, he'd paint my apartment. And if his team won, we'd do it once. And we had a party to watch the game. As the score went toward his favor I admit I got pretty wet. With all of our friends there, it got me even wetter. I knew by halftime it was over, so I took him back to my bedroom and let him take me from behind, you know, doggy style."

To hear Jen talk about sex like this, so frankly and explicitly, had me hard. She continued, as if this was as normal as talking about her work day.

"It wasn't great, the sex, that is. I mean, I entered into it willingly, that's not what I was implying. But he was really bad at it. At least he was quick. The worst part was that the fourth quarter turned around and my team won. So he got some for no reason. That's what I get for jumping the gun."

"Wow, that's...um, kind of crazy. And hot."

"Thanks," she smirked. "There's a lot you don't know about me."

"Clearly," I said.

She looked down at my pants, and saw the erection straining underneath. "Enjoy the story?"

I blushed, but she continued, "Oh, come off it, Steven. I understand how those things work. Besides, that thing is going to be in my face soon, so why be embarrassed."

I paused, then said, "I guess I didn't think about that. You're going to actually see it."

"That's how it usually works," she said with a laugh. "Unless you want it totally in the dark."

"No," I blurted out.

She laughed. "I didn't think so. Any other ground rules we need to set before the deed?"

"Well, okay," I said. "Naked or clothed?"

"Clothed," she said firmly.

"Eye contact?"

"Sure," she said with a wink.

"Do I have to warn you before I come."

"Nah, most of the time I don't get a warning. I mean, I can usually tell when it's about to happen anyway."

"Swallow?" I asked hesitantly. She paused, biting her lip, contemplating her response.

"I owe you," she said. "So I'll swallow, or try to, anyway. Deal?" She extended her hand.

"Deal," I said, shaking it. "I can't believe this is really happening."

"Oh, believe it," she said with a grin. "Since I ruined your first time, and all."

"Well, I mean, doing it with Laura wasn't horrible," I said. "Actually, it was pretty nice." I worried that telling her that would ruin my chance at a blowjob.

"I still should have just asked you if you'd be willing. So, I still owe you. By the way, Laura was very, very complimentary."

"Really?" I said, blushing.

"She didn't go into too much detail, but let's just say she had a great time. Several times."

"Yeah," I said, not meeting her eyes. "It was pretty intense."

"But I really am sorry," she said. "The BJ is just part of making amends."

"Part?" I said.

"Sure," She said, standing up. "I know you like it when I wear shorts around the house, so I wore them." She turned once, giving me a good view of her ass. Her shorts were so small that the bottom of her firm butt almost peeked out from them. She sat back down with a flourish, her long legs propped up on the coffee table.

"And before you ask how I know," she continued, "I'll just tell you right away that it's pretty obvious that you walk around with an erection all day. I know it isn't always because of me, but I figure, at least some of time, it must be right? That's why I guessed that Laura might get lucky with you, I knew you weren't afraid of older women."

"You're not that old," I said quickly.

She laughed. "True, but old enough. And to continue my reparations, let's watch a movie tonight, your pick. We can even watch that French one you're so fond of, the one you kept sneaking up to your room when you were younger."

I stammered a reply, but she just laughed and continued. "Don't be embarrassed, I've seen it before, it's pretty steamy. And since you and I share laundry duty I know what you do all night. Don't worry about it. We all get ourselves off, right?"

"You do?" I asked.

"I do," she said simply. "Everyone does, unless they are lying about it. It's just easier for us girls to conceal the evidence, and whether or not we're aroused. You poor guys have to walk about with tent poles in your pants." She eyed my erection again and stretched.

"Well, now that we've set the ground rules, I'm heading out for a while. I'm cooking your favorite dinner tonight." She leaned forward to kiss me on top of the head. She left the room, and moments later I heard her pull out of the driveway.

I didn't wait to go upstairs. I had unzipped my jeans and freed my dick immediately. It was rock hard, pulsing, and dripping pre-cum. I ran my hand up and down the shaft slowly, using my own arousal as lubrication. My mind was buzzing, unable to focus, and I was halfway to an orgasm when I let go violently. I did not want to come, not yet. I want to build up, to really explode for her. I let my orgasm fade away and began again, stroking in earnest but stopping short of coming. I did this three more times, until I was in agony, and then got out of bed. I walked around the house naked and did some chores, my dick throbbing and dripping pre-cum everywhere. I was thankful for tile floors. When my dick finally shrank down I started to stroke it again, building myself up and stopping. Finally, after hours of getting close, I stopped altogether, and let everything subside and got dressed.

When Jen came home I was on edge. I felt a dull ache in my pants, half pleasurable, half uncomfortable. She still had her tiny shorts and tank top on, and she cooked me my favorite dinner, drinking white wine in the kitchen as she cooked. I sat with her, enjoying talking to her and enjoying the view. After dinner she pulled out the French movie I had snuck up to my room so many times. She grinned as put it on, draping her legs across me as she always did. I was a little jumpy, and my erection had me leaking more pre-cum than usual. The movie was about a young man discovering sex with his neighbor, and then her mother. It was very erotic, with enough full frontal to be enticing to a teenager. I still found it thrilling to watch.

"This is pretty steamy," she said lazily. She shifted a little, her leg moving up my thigh. I twitched, and rested my arm on her calf to keep her from accidentally bumping my erection. On screen, the young man was talking to his neighbor's mother, her flirtation obvious. In a few minutes she'd invite him inside, and then unbutton her blouse a few buttons when he isn't looking. The would end in a sex scene that usually got me off.

"I can't believe we even bought this movie," she said. "It's so raunchy."

"I don't mind it," I said. I knew there was a scene later in the movie where he gets a blowjob from the neighbor's mom, and I wondered if she remembered that scene. "Do you think it's weird?"

"The movie," she asked. "No, just a little silly."

"I meant the BJ," I said. "I mean, you're my stepmom."

"Ah," she said, adjusting her head to look at me. "I see what you mean. No, not really. If you can keep a secret, I've done worse. My sister and I borrowed our stepbrother's car when he came home from college one year. And we wrecked his car. It wasn't totaled, but he'd have to go back to college without it for a while. He was pretty mad but didn't let us know. I felt really bad. And so, after a night of drinking a little too much, I offered him a BJ to repay what we did to his car. I thought he'd say no, but he went for it, so I went down on him.

"What I didn't know is that my sister Charlotte had the same idea, but when she brought it up to him the next day, I guess I had given him so much confidence that he talked her into going all the way. So, while all I did was a BJ, she got taken from behind over the kitchen table. I guess I got off easier, so to speak." She laughed at her little joke, and then turned back to the movie as if what she had just told me was as mundane as a shopping list.

I had missed the first sex scene, but I didn't care. Hearing Jen tell me that story had my dick and heart throbbing. To know she had sucked her stepbrother, had broken some kind of societal norm, and had at least twice used sex as a tool, made me view her in a different light. Part of me—most of me actual—expected her to change her mind. I was, until that point—convinced that the blowjob was probably not happening. But now that uncertainty was gone, and I was nervous.

The movie continued, but Jen fell asleep, her legs draped on me still. The movie ended with the young man in bed with the neighbor, the mother spying through the door, her face inscrutable. I shifted her legs to move, and she partially woke, her eyes still closed.

"Movie over?" she muttered. "I'm sorry I fell asleep." She was half out of it.

"It's ok," I whispered. "Do you need help up to bed?"

She nodded, her eyes still closed. "She reached out lazily, and I tried to help her up. She got up and started to slip back down. "I'll just sleep here," she muttered, flopping onto the couch. "Good night."

She flopped heavily onto the couch, her tits jiggling under her shirt. Her legs were spread out, one hanging off the couch while the other was propped up by cushions. As I looked her over I could see up her shorts. The light blue cotton fabric of her underwear was soaking wet. I stared as long as I dared, and then headed to my room, my dick dripping precum down my leg.

Chapter 3

I slept in the next morning. I woke up with a raging erection but fought the temptation to deal with it. I lay there, my pants on the floor, feeling the cool fabric against my engorged member. I was in a state of constant arousal, leaking precum everywhere. I wondered if it would be better to jerk off, just to relieve the pressure. I also wondered if my long wait would make me last only a second or two in Jen's mouth. I picked up my phone to look up the effects of abstention on stamina, when I noticed I had several text messages from the night before. My alerts turn off in the evening, so I had missed them.

I unlocked my phone and opened the message app. I had several unread messages from an unknown number. The first read "Hi, it's Laura." The second read "I had a good time, and I was hoping you were up for some for fun." My dick twitched, and I felt even more pre-cum run down the shaft. The third message said "If you need a little incentive..." and was followed by a picture. It was of Laura, her shirt pulled down and her tits out. They were massive, inviting. The final message was also a picture. She was nude, turned to the side, showing me the side of her breasts as well as her curvy hips and round ass.

I texted back "Definitely." Then, thinking a bit, I added, "You look amazing."

She must have been on her phone, because seconds later she replied. "Thank you! I thought you'd like them...Are you free soon?" There was a pause as she sent her next message, which was a picture of her lying in bed, topless, and a text that read, "I feel like skipping work."

"Good morning," I head from the door. I dropped my phone, adjusting the sheet over my dick. Jen stood in the door frame, looking at me. "Did I interrupt anything?"

"No," I said, "Just waking up."

"I see," she said. She was dressed for work. I fidgeted, trying to hide my erection. She walked into the room and sat on the bed. "Any plans today?"

"No," I said, shaking my head. I realized my sheets had wet spots from all of the pre-cum, but I tried not to draw attention to them.

"Good. Tonight, let's watch a different movie. My pick, okay?" She leaned forward to kiss me on top of the head. Her shirt opened, showing me her cleavage. She noticed my eyes, and I turned red. "Sneaking a peak, huh? She was still leaning forward and raised her head and lowered her torso, showing even more of her cleavage. As she did, she right arm bumped against my rigid member.

I stammered an apology but she just laughed sweetly. "I know how they work, Steven. You can't hide that thing under a thin sheet." She paused, bumping it again with her arm. Then she sat up, biting her lip. She had a mischievous look on her face. She got up and then sat down softly on my lap. Her ass pressed against my dick, pinning it against my stomach.

"The first time I sat on someone's hard on," she said sweetly, "I was surprised, but I pretended not to notice." She ground against me subtly, grinning. She wore leggings, so there was minimal fabric between us. Her flowery top cascaded over her hips. I was trapped as she sat right on my dick, her ass gently rubbing against me. "It's amazing that something so soft can get so hard," she mused. She kept barely moving, her ass pressed against me.

I couldn't take it anymore. Days of not touching myself, days of sexual frustration and anticipation erupted from deep inside me. I came, my dick pulsing violently against her ass. My dick kept pulsing, flooding the sheet around me, soaking through it. Jen took it all in stride, as if this were completely normal. She remained still as the aftershocks of my orgasm rippled through me, and then stood up. There was a massive wet spot on her black leggings. She looked them over, and then at the mess on the sheets.

"I'm going to change, then I'm going to work," she said. She kissed me on the cheek, lingering as I looked down her shirt. "See ya, Steven," she said sweetly.

She gave me a grin and left the room. I lay there for a bit, and then picked up my phone and sent Laura a text message. "Are you free in an hour?"

After Jen left I showered and headed over to Laura's house. She greeted me in a white t-shirt and faded jeans. The jeans were low-rise, and her shirt was cropped so a bit of her midriff was showing. Her wide hips swayed as she led me into the house.

"I'm glad you wrote me back," she said, looking over her shoulder. Despite having come a massive amount an hour beforehand, I was hard just looking at her. I knew that she talked to Jen, but I didn't know if she knew that I knew about it. That convoluted logic had me thinking as I got ready to see her. I wondered just how badly Laura wanted to get laid. I figured pretty badly, so I pressed my luck. I stepped close to her, putting my hands around her waist. She stopped walking, and I pulled her close to me. I pressed against her from behind, sliding my hands under her shirt. I lifted her shirt off in one motion, tossing it over my shoulder as I turned her around. She had nothing underneath, and her impressive tits were heaving with each breath.

I hooked two fingers into the waistband of her jeans and pulled her close. This action was so familiar, so forward, and she responded in kind. She pressed against me as I unzipped her jeans. She had nothing on underneath them as well, and my hand slid over her bushy pubic hair—already damp—and over her wet labia.

"What do you want to do?" she whispered in my ear. "I'm yours."

"I have some ideas," I said, unzipping my jeans. Without hesitation she dropped to her knees and pulled my dick out. She immediately took it into her mouth, moaning as it slid into her mouth. I held her hair gently, guiding her as she sucked my dick. Her tits swayed as she moved back and forth, her hands on my ass as she took me deep into her mouth. I stepped back, enjoying the view as she sucked me on her knees. I pulled my phone out of my back pocket and held it up. She nodded, leaning back on her hands as I snapped a few pictures of her like that. Then I kicked off my jeans and pulled off my shirt. I helped her up, and then surprised her again by scooping her up into my arms. She laughed as I held her, her tits pressed against me.

"Bedroom's upstairs," she said, her voice almost inaudible. I carried her upstairs to the bedroom, setting her gently on the bed. She spread her legs, her chest heaving in anticipation. She was dripping wet, and I wanted to taste her. I knelt between her legs and then went down, my tongue gliding over her labia.