Stepmom Helps Out Pt. 01

"Oh," she gasped. I stood there, in the living room, grabbing her ass with one hand and jerking off with the other. She was panting, her body plastered to mine. I felt myself closer to coming, this time willing to let myself go and enjoy the release when she finally spoke.

"Wait, don't come yet," she said. I let go of my dick and her ass at the same time, but she put my free hand back on her ass. "You've been going at it for over twenty minutes. I don't want you to wear yourself raw."

"Twenty minutes?" I asked, shocked.

"With your hand on my ass, no less," she giggle. "But let's see if you can resist coming with some added distraction."

She reached behind her back and untied her bikini. She let it fall to the floor so that her breasts were free. Her chest was heaving and her nipples were hard, and I stared at her with my mouth open.

She laughed, and pointed downward. A large strand of pre-cum hung from the tip of my penis and dripped onto the tile floor. I went to start stroking but she stopped me.

"Not yet," she said, leading me back upstairs. I kicked off my swimsuit and followed, my dick bobbing with each step. She eyed it and laughed.

"You're doing better than I thought," she said, dragging me into her bedroom. She pressed herself against me, her bare breasts brushing against my chest as we fell onto her bed.

"You're a good teacher," I said. I pulled her close with one hand and ran my other hand up her firm stomach. It was slick with my pre-cum, and as I got closer to her breasts she said nothing. My fingers inched closer and finally I cupped her breast with my hand, feeling it's softness and the small, firm nipple. She gasped as I felt her tits with one, then two hands. Finally, I pulled her closer and held her by the ass as I started to stroke myself. I could feel an intense orgasm building but I kept delaying it.

"That's it, keeping going," she said, "keep going, baby."

She whispered in my ear and writhed against me and suddenly I flipped her onto her back. Her tits jiggled as I straddled her waist. Her eyes lit up and she said "do it, come on me."

I grinned, letting myself go. The intense orgasm I had built up for so long took over and I felt myself starting to come. Enormous spasms overtook my penis as thick ropes of cum shot up her stomach, splattering her tits. She laughed as I covered her in semen, as the biggest orgasm of my life washed over me. My eyes lost focus and I kept coming. Finally, I could see straight again and I looked down at Annie.

Cum covered her tits, with thin strands of bridging her breasts and pooling between them. Some cum had hit her neck as well and thick trails of it ran down her stomach. I was panting and so was she.

"I'm sorry, I can't wait," she said, and suddenly slid a hand down her stomach. As she did her fingers slid along my cum and she darted her hand under her bikini bottom. I got off her her thighs as she rapidly rubbed herself off right in front of me. Her breasts swayed as her body writhed, and she came quickly, bucking her hips and crying out. Her legs were spread wide and I saw her hand dart rapidly up and down as she rubbed herself to one, and then two orgasms back to back. As she writhed around my cum ran down the side of her stomach and chest, dripping onto the sheets. Finally, she stopped, withdrawing her hand and resting it on her leg.

"Sorry," she said again. "I couldn't help it. All this has been pretty exciting for me, too."

"It's okay," I said, grinning. "You know, you can do that any time you're getting hot from our lessons, I don't mind."

"Deal," she said, her eyes closed. We lay there for a while, saying nothing. Cum dripped down her tits and formed rivers down her stomach, pooling near her naval, and finally dried against her soft skin.. We said nothing, until she reached over and took her phone from the nightstand.

"What's up?" I asked.

"Checking where Liz and your dad are," she said. "Still out, but they might come back soon." She sat up, examining the drying semen that covered her breasts and stomach. She got up and picked up a sundress from the dresser, slipping it on. She pulled me out of bed and told me to get dressed while she retrieved our bathing suits from the living room. When I joined her downstairs she had her purse and car keys in hand.

"Come on, let's get something to eat," she said.

We had lunch at a small cafe near the beach. My eyes were glued to her sundress, and the small amount of cleavage I could see.

"So can I ask you a question?" I asked.

"You can ask me anything," she replied.

"Well, since I've seen you topless, um..."

"You want to know if you can see me like that all the time?" she finished for me. I nodded, blushing a little. She blushed, too, and then said, "We need to talk, Mike."

My face fell, but she continued. "Society wouldn't approve of me teaching you how to last longer, you know that, right?"

I nodded, and she continued. "And I'm married, to your father. And I've always been faithful to him," she said. "So maybe..."

"Maybe we should stop," I said for me. "I get it. It's okay."

"Well, if you had let me finish," she said, grinning, "I was just going to say we have to be careful. I love your father, very much. And I would never do a thing behind his back in any other circumstance. But I care about you and I want you to be good at it, so I am going to help you. But we need to be really discrete."

"Oh," I said, relaxing, "I thought you were going to tell me you didn't want to help me out anymore."

She grinned, playing with her salad while she looked at me. "I've got nothing on under this sundress except for a bikini bottom and your cum. You would have thought that I'd have showered first if I felt that guilty."

I sat back and smiled as she ate. She grinned at me, her eyes sparkling. She set down her fork and said, "did you enjoy that last bit, when I came."

"I did," I said. "I was feeling a little guilty that I was getting off and I wondered if you were turned on or not."

"Oh, very turned on," she said with a grin. "But I usually waited until later, for your father. I have to say he's been a beneficiary of all of this. I can hardly get through dinner without taking him upstairs these days."

"Glad I can help," I said, causing her to laugh hard. We finished lunch and Annie announced that she wanted to go to the movies. I agreed, and she texted my dad, who was still golfing, and excused herself to the restroom. I paid the bill and waited by the door for her. When we got to the car she got into the passenger seat and handed me something. I looked down at the balled up fabric of her bikini bottom in my hand and then looked at her twinkling eyes.

"The only thing I've got on under this sundress is your cum," she said quietly, taking back the bikini bottom and putting it into her purse.

We drove to the movies, where we picked a comedy and took our seats. The Sunday afternoon crowd was small, and as we waited for the previews she leaned over and said, "I like to go out with nothing on like this," she said. "It's fun. And it's fun telling the person with you that you've got nothing else on."

I grinned, and she patted my leg gently. She leaned over again, this time turning her body to face me, and said, "you know, I think that was the biggest load of cum I've ever had on me."

"Really?" I asked, grinning. She nodded.

"Well, at least from one guy. I was so turned on I had to rub myself off. Sometimes I get so wet I just have to right then and there."

"Where's the weirdest place you've rubbed yourself off?" I asked.

"One of the weirdest places was in church," she said. It was after mass, and I was probably nineteen. And I was so wet thinking about something or other that I went to the bathroom and took care of it right there. I got back in time for the sermon."

"Whoa," I said.

"But the weirdest place was in my bedroom," she said with a grin as the previews started.

"Really?" I asked, a little disappointed.

"Well, when you hear what was going on, you'll know why. I was home from my freshman year in college, and my parents still weren't used to me being around. And I was in my closet, putting some things away, when I heard some laughing down the hall and footsteps coming my way. I was about to call out and say hello when suddenly my dad walked into my room, followed by my mom. My mom was wearing some of my clothes, and had her hair up the way I used to wear it when I was younger. Something seemed strange so I hung back and hid in the closet.

They were both tipsy, and my mom kept calling my dad "daddy," and then I realized she was supposed to be me. And she was telling him how I was getting bad grades—which by the way I never did—and how I was going to get in trouble at school. And my dad told her she'd been very bad and needed to be spanked. And I had to stifle a laugh as they played out this cheesy role playing, but then I was surprised again because she got on her knees and said "maybe I can suck your dick instead, daddy?"

As she told me her story I could see in the dim theater light that Annie was running a hand up her leg. It disappeared up her dress and I decided to take advantage of her lust and put my hand on her other knee. She didn't stop me as I slid up her thigh while she kept talking.

"And so I hid in the closet while my mom unzipped his pants and took out his dick. She started to suck him and he ran his hands through her hair and called her my name. I was only a few feet away, hiding in the darkness, while she sucked him."

I continued up her thigh, feeling the heat from her skin as she rubbed herself off. No one was around us, and I kept sliding my hand along her thigh until I reached her damp labia. They were slick with her arousal and her fingers were rubbing her clit furiously.

"And then she stopped sucking him and he helped her up and took off her clothes. Then she took off his shirt and lay on the bed. My mom spread wide, her pussy dripping wet, and said "fuck me, daddy, make me your bad girl."

I pressed my fingers against the entrance of her pussy and she slid her ass down and spread her legs, giving me access. I slid into her easily, burying to fingers deep inside her as she fingered herself faster.

"I watched my dad get on top of her and bury his dick deep inside her as she screamed in pleasure, and I rubbed myself off in the closet while my dad fucked my mom and pretended she was me."

I felt Annie's pussy tighten around my thrusting fingers and she came. I felt a flood of wetness gush over my hand, and felt her heart beat in her vagina. She sighed, leaning back and taking both of our hands out from under her dress.

"I hid in that closet for an hour, and I must have come twenty times," she said quietly.

"Wow," I said, wiping my slick hands on my jacket. She reached over and squeezed my hand.

"I think that's enough for now," she said dreamily, and leaned back to watch the rest of the movie.

We got home and no one was there. I said nothing, but took her hand and let her to my room. She bit her lip as I lifted off her sundress, revealing her nude body.

"Turn around, slowly," I said in a low, deep voice. She turned, showing off to me. Then I unzipped my shorts and took my out swollen penis. I pulled her close and we fell onto my bed. I cupped her bare ass as I stroked.

"Come on me again," she said. "I want to wear it all day."

"Won't dad notice?" I said.

"Not for what I have in store for him tonight?" she said, grinning. I stroked and she rubbed her body against me. We writhed against each other and Annie gave up all pretense and started rubbing herself as I jerked off. I kept going delaying my orgasm once, then twice.

"Come on me," she panted, her body tensing up as her orgasm overtook her. I got on my knees and let myself go. I came, splattering her tits again. As I came I aimed, spraying her stomach, then her pussy and thighs, with my cum. I thought I may have crossed a line as semen splattered her wet pussy but she didn't say anything to stop me. Finally, spent, I looked down at her as she looked up at me with dreamy eyes.

"I've never told a soul about watching my parents like that, not even your father."

"It was pretty hot," I said.

"That's why I told you," she replied. She sat up, cum dripping off her tits and onto her thighs, and patted me on the leg. "I better go and get dressed, tomorrow I've got a new lesson for you."

Chapter 5

Tomorrow, it turned out, my father had planned on taking Annie out of town for a few days as a surprise. With my stepmom out of town and my lessons on hold, I was bored. I practiced, though, and found that I could last as long as I wanted if I tried. The new feeling of accomplishment also meant that soon Annie wouldn't need to show me anything, and we'd return to our old way of life. Would I still be able to jerk off with her in bed with me, our bodies touching, my cum splattering her body? Would I even get to see her naked, or topless? The idea that I could lose my time with Annie overshadowed my new confidence about delaying my own orgasms.

By the time Annie returned three days later I was so dejected at the thought that I might no longer need her help that she could see it in my eyes.

"Everything alright?" she asked as I helped her and my dad bring their suitcases in.

"Yeah," I said, trying to look upbeat but failing. I covered quickly, "you know, three days with Liz at home."

"Well, you two should work harder to get along. I know she seems abrasive, but once you get past that exterior she's very sweet. Besides, I thought you'd be happy to see me."

"I am," I said, grinning slightly.

"How happy?" she asked, leaning forward a little so her cleavage showed a little.

"Very," I said. I could hear my dad in the garage and since Liz wasn't home I decided to be a little adventurous and put my hand around her waist and then grabbed her ass gently.

"Your father is in the garage," she said in a sing-song voice.

"I know," I said, still grabbing her ass. She pressed herself close and then said, "give me twenty minutes and be ready to go."

Twenty minutes later I had my car keys and was waiting by the kitchen when Annie came downstairs. She wore another sundress, and I knew from the grin on her face nothing else.

"Your dad is exhausted," she said, grinning. "I think he's going to sleep for a while."

"Oh, really?" I asked.

"Really," she said. "Come on, let's go."

We drove to the edge of town, where houses and stores gave way to wooded lots. We kept driving until the road turned into a canopy of trees.

"Turn left," she said, pointing to an unmarked road.

"Where are we going?" I asked.

"Somewhere private," she said with a grin. We drove down the unpaved road for about a mile, then took another left. That road ended abruptly in a field surrounded by trees.

"We come here all the time, your dad and I," she said, getting out. She pulled a picnic blanket out of the trunk and set it near the car, beckoning me closer.

"Did you miss me?" she asked as I approached.

"Yes," I said.

She grinned, unbuttoning a few buttons on her sundress until her breasts were exposed. "Show me," she said.

I unzipped my shorts and freed my swollen member. She lay back as I took off my shorts and joined her on the blanket. She immediately began rubbing her wet pussy as I lay next to her. I slid two fingers into her, thrusting them deep inside her as she rubbed herself off. The only sounds in the field were the birds, the wind, and our breathing. Annie came, crying out loudly as she thrashed about on the blanket. Her pussy clamped hard around me and she bucked her hips as she came, and then gently took my hand and withdrew it from her pussy.

"Now you," she panted. "But this time hold off as long as you want, and when you come, I want you to concentrate on staying hard while you're coming. See if you can stay hard, okay?"

"Okay," I said.

"The first time you come, you can come like you usually do, but if you can stay hard, you can come on my face."

I nodded, and knelt next to her. She rubbed herself off and I felt her tits with my free hand as I stroked myself.

"That's it, baby, stroke that dick, come on, do it," she said in a hushed voice. I stroked myself and felt her tits, all the while holding off my own orgasm as she came over and over. Finally, satisfied I had gone long enough, I relaxed, stroking myself close to orgasm. I looked at her writhing body and concentrated, tensing up my muscles as I came. I covered her tits, aiming at them as spurt after spurt deposited more sticky semen onto her body. She gasped, coming again, and I kept stroking and thought about staying hard. To my surprise I remained rock hard, my hand slick with cum as I kept stroking.

"You did it!" she squealed, taking her hands off of her pussy and rubbing her cum-splattered tits. "Keep stroking, baby, and come on my face."

I stroked, marveling at how far away an orgasm felt. I rubbed her tits with my other hand, feeling the slick cum all over her skin. I ran my hand downward, and gently slid it over her labia. My fingers were covered in my cum and I thought she might stop me as I gently pressed into her pussy but she opened her legs wider to accept me. Soon she was rubbing herself off as I penetrated her with my sperm-covered fingers. I knew she was on the pill but the the idea that my own semen had entered her was exhilarating. The feeling brought me closer to orgasm, but I was able to delay it as she came once, then twice. Finally, her hips bucking in ecstasy, she begged me to finish. I withdrew my hand from her pussy and straddled her chest. Her tits were pressed between my legs and I let go and came. While my orgasm was smaller, it was more intense, and I dribbled what little cum I had left onto her face. She laughed, catching most of it in her open mouth, until my penis finally softened and feel limp between her breasts.

We stayed there for a while, silent. Finally she sat up, her cum-splattered face and tits still dripping cum.

"I think you've learned how to do it," she said. She grinned and I smiled back, trying to hide my disappointment. She wiped her face with a corner of the blanket and retrieved her sundress. I got dressed and folded the blanket, and stepped into the car, where she was already waiting.

"There's one thing, though," she said, her eyes locked on mine. "Tonight, wait for me, okay. There's something I need to see. But for now we'd better get back home, your dad will get up eventually."

Annie drove me crazy all day in the sundress, and while I knew she was naked underneath I wondered if I'd ever see her naked again. I tried to hide my disappointment, and tried to console myself that if we were really finished that I didn't have to worry about not lasting long enough with a girl. I sat through the usual nightly romp coming through my air vent, wondering if she was coming to say goodbye. The sounds from the vent died out and some time passed and I was starting to think she wasn't coming. Then a small knock on my door snapped me out of my downward spiral.

"Hey," she whispered, stepping into the room. She wore a black bra and matching underwear, and she locked the door behind her as she stepped in. She pulled me out of bed, grinning, and helped me out of my pajama bottoms.

"I bet you thought I was going to say goodbye," she said quietly with a grin. "You've learned how to hold off, and even come more than once. I'm so proud of you."

She had me sit down on the edge of the bed. She unhooked her bra and slipped out of her underwear. Naked, she stood in front of me and ran her hands through my hair. Then she knelt down in front of me. I started to stroke myself but she took her hand and put it on my wrist and stopped me.