Bargain with Stepmom Pt. 02

He took in my words carefully, and nodded slowly. "Understand her. Does she, um, has she had to...repay you for something?"

"You can put it that way," I said, grinning. I mouthed the word 'blowjob' slowly.

Jason exhaled. "I thought you were going to confront or judge me. Or worse, tell my wife. That was a long time ago," he mused. "So she's still at it, I see." His expression softened, and he grinned. "I can tell you, I was not expecting it. I was pissed, right, because she had wrecked my car. And she came to my room, and was all sweet and innocent about it. She apologized, and while I was ranting at her she just casually said she'd suck me off to make up for it. I thought she was kidding. And then she opened her shirt, and god, those tits."

He seemed lost for a moment, then continued. "So, yeah, I let my stepsister suck my dick. I came all over her, it was in her hair and everything. Our parents were downstairs, and she had left the door open. I was so afraid we'd get caught, it just heightened everything. There she was, on her knees with her tits out and my dick in her mouth. It was—and maybe still is—one of the craziest moments of my life. Anyway, I came and she got up and cleaned up and buttoned up her shirt and that was it. So, has she already, or did she say she was going to?"

"Since we're speaking confidentially," I said, "she already has."

"I wonder if she's as good as she was back then," he mused. "She's certainly had a lot of practice. So just a BJ?"

"Yeah," I said, omitting some of the details. "It was amazing."

"I bet," he said. "I didn't think it could get any better with her." He stopped short. I looked at him and he said, "never mind."

"Come on, you can't say that and stop there. What did you mean?"

He sighed, taking a drink. "Well, since you're not judging, I'll tell you this. We did it, once. And it was wild. It was at our family reunion, a year after the BJ. If you want to get her to talk about it..."

As he whispered his final comments the women returned. I looked Jen over, and I saw Jason do the same. His wife did not notice. Jen extended her hand and said to me, "are you too cool to dance with your stepmom?"

"I'm the least coolest person I know," I said, and took her hand. We walked out to the dance floor and slow danced with everyone else. Jen wore a silver dress that clung to her curves. It was modest, but I also knew she had a bra on and nothing else. When we had gotten to the hotel room we had ended up kissing, naked, her hand wrapped around my throbbing dick, when someone knocked on our hotel room door. We quickly got dressed and she opened the door to well-meaning relatives wanting to say hello. In the scramble, her underwear had ended up tangled in our sheets, and we had headed out to the rehearsal dinner.

We danced as one might expect from a stepson and stepmom. As we danced, she asked what Jason and I had talked about.

"Oh, not much," I said. "Just about you, when you were young and stuff."

"Embarrassing stories about me?" she asked.

"Sure," I said. "Not more embarrassing than anything you've told me. I mean, how many people here have you done something with?" I said this with a smile, and, in the dim dance floor lights, reached down and gave her ass a gentle squeeze before returning my hand.

"Oh, you know," she said casually, "I'd have to think about it." She looked around as we danced. "Just two, here, actually. God, that sounds awful."

"Who else?" I said, looking around.

"You are going to think I'm horrible," she said.

I leaned in close, "given how I've spent my last few weeks, I'm not going to judge. Seriously, who was it?"

"See that guy in the light grey suit?"

"The guy in his sixties?" I asked.

"Well, he wasn't in his sixties back then, but he was older than me by over twenty years. That's my stepdad's friend Mitch. He and I did it a lot one summer, when I was home from college. He hired me to help in his dental office, and I stayed late a lot, and, well, we fucked right on the dental chairs. He was married, which I feel bad about, really. But his wife wasn't interested, and he was interested in me, and we did it once because I felt bad for him. And after that we did it at least once a day, because he was so good at it. Once he fucked me from behind and my mom had an appointment the next day in the same chair. It was crazy. We must have done it like a hundred times."

"Jeez, how many times have you done it?" I asked.

"I couldn't count, to be honest. Let's just say I enjoy myself."

"And who's the other family member—or friend of the family—that isn't here that you've done it with."

The dance ended and the lights came up. She looked around and someone she knew asked her to dance. She smiled and left me to dance. I looked the retired dentist over. I decided against talking to him, and before I could do anything else Jason's wife, Danielle, asked me to dance. We made small talk, all the while I wondered if she knew that her husband had had sex with his stepsister when they were younger. When the dance ended Jen found me and took me by the arm.

"Let's get some fresh air," she said, and led me out of the room. The music faded as we walked through the hotel halls. We wandered, her draped on my arm, before she started talking. "Do you think I'm terrible?"

"No, of course not," I said. Then I asked a question I had wanted to ask, but was afraid to. "Did dad know about all of this?"

"No," she said. "I wasn't keeping it from him, you know. But it just never came up. He knew some things, here and there. Like the football game bet. God, that turned him on. He used to bet me all kinds of things to get me in bed. Even though he'd get me in bed whenever he wanted, it was fun to make it due to a lost bet. Or some kind of favor. I know it's been a long time, but I still miss him."

We walked the hotel grounds, a beautifully manicured garden, in silence for a while. I finally spoke, "about, well, about Dad. I guess he wouldn't be happy with either of us right now."

"When he passed away, he told me to be happy. And he asked me to take care of you. And right now, I'm happy taking care of you. He knew what I was like, I don't think he's mad. Are you feeling guilty?"

"A little," I said. "Just thinking about family a lot tonight."

"I know," she agreed. "Seeing everybody is bringing back a lot of memories. I'm glad I have you here. And don't worry about your dad. You know, he really wanted me to give someone a blowjob in front of him. He never asked explicitly, but I knew he wanted to. He knew that I once did two guys at once, and when I told him he was so turned on he fucked me three times in a row, a record."

"Two at once, huh?" I said.

She stopped, and sighed, "yes, once. It was Jason, believe it or not. And his cousin, Brian. We were visiting for a family reunion, about a year after I blew him. I'd never done anything with him again, although I knew he wanted to. The extended family had rented a campground and we had tents everywhere. Jason, and Brian, and I were hanging out in a tent, mid-day, it was so hot. And I don't know how we got on the subject, but we started talking about whether or not size mattered. Brian, as he liked to tell everyone, had a very big dick. He brought it up constantly to anyone who would listen.

"I remember Brian was bragging about how, by virtue of his size, he was bound to be better at sex. He was specifically trying to get at Jason, and I was defensive of my step brother. I told Brian that size didn't matter, and he said he didn't believe me. So, I told them that I'd judge right then and there. You should have seen their faces. I slipped off my shorts, buried my face in the sleeping bags, and told them each to go inside me and stroke a few times, without telling me who it was. And I'd tell them who felt better, who was better at it.

"So I did. And I remember waiting, with my ass in the air, for one of them to stick it in. I was getting pretty wet as one of them got behind me, his dick probing me. He slid in slowly, and I knew just by the size it was Brian. He was pretty awful, just thrusting away like he was sawing through a log. I let him enter me and thrust for about a minute before I told them to switch. He pulled out and after a little bit Jason slid into me. He was smaller, but immediately he angled differently, and each time he thrust into me I felt an electric tingle building inside me. I let him keep thrusting for a while, and finally said 'whoever this is, you're so much better. Don't stop.' And he started fucking me. I could feel an orgasm building inside me, and I came hard, biting my lip to keep quiet.

"I lifted my head up, and Brian was sitting next to me, looking dejected. His dick—and it was the biggest I'd ever seen—was still pretty hard, and I felt sorry for him. All those years of bragging, and I crushed his spirit. So I told him to let me suck his dick. He jumped at the chance, and Jason was thrusting into me while I sucked Brian. Jason came first, and I let him come all over my ass and back. Brian got close, and I stroked him to the final point, and he came on my face and neck. And I rolled over onto their sleeping bags, exhausted."

We were near the elevator when she stopped talking. I looked at her, and wordlessly I hit the up button. We said nothing as we entered the elevator and took it to our room, as a woman was already in the car. As we walked into the room I pulled her close and kissed her. She pressed her body against me as I unzipped her dress. She let it fall to the ground and took off her bra. She stood, naked, her pussy dripping in anticipation.

"You owe me," I said, "for what happened."

"I know," she nodded.

"But you're not paying me back right now," I said, taking off my clothes quickly. "This is about us, right now. And right now, I want you."

"I want you to," she said, pressing her body against me. I cupped her ass and ground against her as we kissed. I ran my hand through her short, wavy hair and she dipped her head back. I took it as an invitation to kiss her neck, running down and over her collarbone. I then reached down, grabbing her by the ass and lifting. She jumped up, wrapping her legs around me as she fell gently against the wall.

"Now," she said.

I didn't hesitate. I lifted her a little more, so that the head of my swollen, throbbing dick was rubbing against her slick labia. With barely any effort the head of my dick popped inside her, and I thrust deep into her. I was inside my stepmom.

We fucked hard, against the wall, our bodies plastered together. It was all I could do to stay upright, as I held her up and she wrapped around me. Jen came quickly, her pussy tightening around me as she panted hard. I kept thrusting, lost in the feeling of her body against mine, and she came again. This time I could not hold off, and I exploded with her. She cried out as I came inside her, filling her with all of the arousal of the moment, and the hours that led up to it. We stayed against the wall, her pussy and my dick pulsing in unison as I filled her with my semen. Then, as we came off our mutual climax, I set her down gently as I pulled out of her. Cum ran out of her and down her thigh, and she laughed.

I pulled her to the bed, and she lay down and spread her legs wide. She was a dripping mess, and I was still hard. I knelt between her legs and leaned forward to kiss her breasts, crushing her nipples gently between my lips. As I paid attention to her, she stroked my slick shaft, begging me to enter her again.

"How will you repay me if I fuck you again?" I asked between kissing her breasts.

"I'll fuck you every day, how about that?" she panted.

I grinned, and slid into her. She gasped, her eyes closing in delight as I started to fuck her again. It was more enjoyable now that I wasn't holding her up against the wall. My hands were free to roam and I felt her magnificent tits as I thrust into her. I was not even close to coming, and as I thrust into her, she came repeatedly. She moaned softly with each orgasm, her pussy gripping me tighter and tighter. Eventually I felt myself getting closer, and I came inside her again. She laughed in delight as I came inside her a second time, my orgasm just as intense as the first. She sat up and pushed me to lie flat on the bed. She crawled between my legs and started to lick my dick clean.

She took me into her mouth gently, mindful of how sensitive I was. She sucked me slowly, my flaccid dick trying to give up despite her efforts. She swung herself around so her pussy, dripping with my cum and her wetness, hovered over my face. I dove in, licking her labia and clit as she sucked me. I could feel myself getting hard again, but was enjoying the feeling of her pussy in my face. I licked recklessly, listening to her squeals when I hit the right spots. I teased her, avoiding her clit until she'd shift herself so my tongue would hit it. I was hard again, and now she was sucking me in earnest.

Jen came suddenly, her body shuddering. A flood of wetness and my cum leaked out of her and onto my face and chin. Was a mess, covered from her pussy's contractions. I kept licking until she leapt off of me.

"I need a break down there," she panted, laughing. I pulled her close, kissing her. I felt her tits as she stroked my dick, and I was inspired. I straddled her, and put my dick between her tits. She understood, and pressed her tits together around my dick as I started to thrust. I was lubricated from all the cum and wetness, and I slid between her tits effortlessly. She maintained eye contact while talking dirty to me.

"That's it, baby," she panted. "Fuck my tits. Come all over me."

I had come twice already, but eventually my orgasm started to materialize. I was getting closer, and she could tell by the angry, deep red color of my dick. She picked up the pace, rubbing her tits to match my thrusts. I came, a relatively weak spurt of cum shooting from between her tits and hitting her face. Smaller pulses of cum shot out, covering her tits. I kept thrusting, willing myself to stay hard.

When I stopped coming I got off of her and took her hand. She accepted, and let me pull her gently out of bed. She looked puzzled. We both looked worse for wear. Her hair was damp and hung in loose waves over her forehead. We were both wobbly on our feet, and she laughed and fell against me when she stood up.

"What now?" she asked. "I'm a little worn out, it's been a while since I've been with someone with so much energy."

"I had an idea," I said, and gestured to the balcony.

"You've got to be kidding," she said, looking over my shoulder. She was pressed against me, and I gripped her ass gently.

"No one will see who it is at this time of night," I said.

"But anyone who looks up from the grounds will see two people doing it on the balcony," she replied.

I took her hand and led her to the balcony. "I bet no one will see us," I said. I pushed her gently and she bent over the balcony, her ass sticking out to me and her tits hanging over the stucco. It was late, and the neighbor's balconies were empty and dark. We were six floors up, and anyone looking up would see us, but not recognize us.

As I thrust into her, beating my father's record, I looked down on the grounds. She thrust backward to meet my motion, our bodies slapping together. We fucked hard, our bodies exhausted. I never wanted it to end, that perfect night with Jen. I could no longer tell when she was coming, as her body shuddered over and over. She cried out, and a couple down below looked up. Jen's tits were swinging as she leaned over the balcony. It was obvious what we were up to as they pointed up to us.

I came, my body giving out as my dick pulsed inside her. I didn't even know if I had cum left to give her, but it didn't matter. I pulled out of her and we stumbled back to the bed and collapsed together. We were too exhausted to move. As we drifted off to sleep, she whispered in my ear.

"I won that bet."

"You cheated," I said.

"We never said we couldn't make any sound, so I won. And since I won, my prize is that you are going to move into my bedroom when we get back."

"What if I had one the bet?" I asked.

"You'll have to make a new bet to find out," she said, kissing me. And, finally, we fell asleep in each other's arms.

END

Note: My next series is going to be based on Jen when she was younger, coming soon!