Stepmom Helps Out Pt. 02

Chapter 1

"I'm sorry, Mike," Annie whispered in the hallway as we passed in the morning. "Your dad's off today."

"It's okay," I said, trying to hide my disappointment. The day before Annie had been kneeling between my legs, her hand wrapped around my spent penis and her tits drenched in my semen. She had promised to help me with my problem—and so far she had. I had learned, with her help, to hold off my orgasm until I was ready, and more importantly to stay hard and come again. But the second something other than my hand touched my dick I lost control as if I had learned nothing. Still, she had promised to help me, and my mind reeled at the thought of learning to control my climax at her hand.

"Maybe tomorrow?" she said, pecking me on the cheek quickly before heading downstairs. I retreated to my room, passing my stepsister Liz as she emerged from her room. As we exchanged dirty looks I thought that I would be more attracted to Liz if she wasn't such a bitch.

"Morning," I said.

"Morning," she said back. She opened her mouth for a snotty retort but I walked past. She turned around and followed me into my room.

"I was talking to you, jerk," she said.

"I didn't feel like hearing your voice," I said, trying to sound bored. She huffed off and stormed down the hall. Seconds later Annie appeared in my room. She listened down the hall for second before she came inside.

"I know you were looking forward to today," she said plaintively. "I'll make it up to you."

"I know," I said. "Don't worry about me, have fun."

Annie smiled, pecking me on the cheek again before leaving my room. Liz suddenly appeared in the door frame, smirking.

"What?" I asked.

"Just watching you and mom," she said. "What's she making up to you?"

"Just being nice to me because her daughter's a total bitch."

"I'd say go fuck yourself, but that would only take a few seconds," she said, sneering. She turned and headed out the door, laughing.

My dad ended up taking two extra days off of work, and I spent the days out of the house hanging with friends. It was summer and Liz and I both went to the university in our town and had no classes, so I had plenty of free time and people to see. I was starting to wonder if I'd ever get a chance to even talk to Annie again when, on Friday, my dad went back to work. I was sitting in the living room with Liz, enjoying a moment when she was quiet for once, when Annie came downstairs. Her hair was tied up in braids and she wore a short skirt and knit shirt. I tried not to stare, and realized how much I missed seeing her naked. I looked over a Liz, who was very cute—albeit bitchy—who looked at me through narrowed eyes.

"What's up, mom?" Liz asked.

"Not much. I was coming to see if you two wanted to come with me to the hardware store. I want to get some new plants."

I grinned. Liz hated gardening and promptly said no, finding an excuse to leave the house.

"Alright," Annie said, dangling her keys in front of me. "Let's go plant shopping."

I drove and we were quiet at first, until Annie spoke.

"Sorry it's been so long," she said.

"It's okay," I said. "I've missed it, though."

"Me, too," she said. "It sounds weird to say that out loud. And when I told you not to use your hand, I didn't think I'd be depriving you for days and days. I bet you couldn't resist the temptation."

"I did," I said. "I haven't come for days."

"Really?" she said, her eyebrows raised.

We got some plants and other things she wanted to put in the garden over the weekend and drove home. We unloaded them into the garage and she shut the garage door. As soon as it closed she turned to me.

"I realized that you had figured out to control things so well partly because you could adjust the rhythm of things. But when you're with someone else, they won't change the rhythm the way you need so you have to concentrate harder. So I'm going to help you some more. That is, if you don't mind a bunch of handjobs from your stepmom."

"When you put it that way," I said, pulling her close, "I don't mind at all." I unbuttoned her shirt and she laughed.

"Right now?" she said.

"Right now, in the garage," I replied, pulling her shirt off. She unhooked her bra and slipped off her skirt, so that she stood naked before me. She grabbed a beach mat and knelt down on it, unzipping my shorts.

"Anyone could walk in on us," she said, biting her lip.

"I know," I said, grinning.

"Alright, just like before," she said. "Enjoy it, but concentrate on holding off as long as you can. Don't try to stay hard afterward, just try and delay it."

"Okay," I said. Annie grinned and started to stroke me. She stroked me for some time in silence, her eyes locked on my throbbing penis. After some time she looked up at me, grinning, and spoke.

"The first time I ever did this," she said, "was with my neighbor. He was forty-something, and I was eighteen. I babysat his kids because he was a single dad. And he was really sweet, always nice to me."

Annie talked while she stroked me, her breasts jiggling as her hand moved up and down my shaft. I fought off the first wave of climax and soon concentrated on the building pleasure that came with each denied orgasm. She kept stroking, talking to me.

"One night, when his kids were asleep and he came home, we started talking, and he mentioned he hadn't been on a date in years, and then I asked him if we wanted me to get him off. He was shocked but I saw him looking at my tits and so I begged him to let me. He got up and backed away but I pulled down my top and showed him my tits. I looked at him and saw how his eyes were glued to me, and told him I wanted his cum. He finally relented and I stroked him off in his living room. I didn't know cum was so messy until then."

"He hired me a lot more often after that," she said, "and when he'd come back home I'd get him off," she said. She was stroking me faster and it was getting harder to fight off the urge to come. I looked down at her and she nodded, and I relaxed and let the intense pleasure building inside me take over.

"Are you going go come, baby?" she asked, stroking me harder. I nodded, and she grinned. I erupted, my cum spurting all over her body as she held my firmly in her hand, stroking the cum out of me. She laughed softly as thick ropes of semen landed on her breasts and neck, covering her with days of pent up lust. When I finished it was all over her, dripping slowly toward to the garage floor.

"Do you want to know low long you lasted?" she asked, grinning. I nodded, and she kissed me on the cheek. "Ten minutes. Not bad, kiddo."

I grinned, and pulled her close to me. Her wet pussy brushed against my leg and I felt inspired. I lifted her up and set her on the trunk of my car. She looked at me in surprised by I knelt between her spread legs and she leaned back, sighing.

I had gone down on girls before, plenty of times. I felt like I had to in order to make up for my short performances. I had gotten pretty good at it, but judging from Annie's past I would have some considerable competition. I didn't hesitate, and ran my tongue up and down her wet labia as she spread her legs more. I slid two fingers inside her and starting swirling my tongue around her clit while pumping my fingers into her. She was close already and it didn't take her long to start coming. I kept thrusting my fingers into her, working a third finger inside her as she started to rock back and forth on my car.

It occurred to me at that exact moment that if my father came in at that moment there would be no way to explain to him why I was licking his wife's pussy with three fingers shoved inside her. The entire time with Annie my dad had been an afterthought, but then it occurred to me that there was a serious danger element to what was happening. Furthermore, Annie liked it.

"Oh god!" she gasped, clamping her legs around me as she came. She shuddered and suppressed a loud squeal as her vagina clamped down hard on my pumping fingers. She begged me to stop, letting her orgasm fade slowly. I stood up and looked as her as she lay on the trunk, a stream of wetness dribbling onto the car trunk as what was left of my semen dried on her skin. I stood up, stretching, and tossed her clothes onto the trunk next to her.

"You'd better clean up before dad finds you," I said, knowing even that slight thrill would get her going. "Oh, and Annie?"

"Yes," she said, still laying back on the car, exhausted.

"Once I'm used to your hand, won't I have to get used to other things as well?" I asked, grinning.

"Don't push your luck," she said, sitting up slowly. But as I left the garage, I looked back and saw a grin spread across her face.

Annie was giddy all day, and exchanged glances with me whenever she could. I knew that she was covered in my dried cum, and that kept me hard all day. I also reflected on what she had told me already. Clearly, Annie had a lot of experience, and she had done some crazy things, like jerking off her neighbor and spying on her parents. I wondered just exactly what had gone on with her over the years. At the same time that Annie was sneaking glances at me, Liz was, too. Unlike Annie, Liz seemed puzzled by something, or maybe just trying to snoop. It wasn't until around midnight that I heard a knock on my door. I was naked under my sheets, and expected Annie to peek in, but instead Liz entered the room.

I sat upright, surprised, and pulled my sheets over me to hide my erection. She nodded at me, and said quietly "can I come in?"

"Um, I guess," I replied. "I was about to go to sleep."

"It's just," she said, pausing to find the right words, "you seem...I don't know, different lately. Like something's up." Her usual bitchy demeanor was gone. In it's place she seemed almost pouty to me. I looked at her as she leaned on my door frame, her head cocked to one side as she studied me.

"I'm the same old me," I sighed, leaning back a little. She stepped in a little and shut the door behind her.

"Do you always sleep naked?" she asked.

"Who says I'm naked?" I said back.

"I'm just guessing the way you're covering up," she said with a shrug. "Anyway, I do the same thing; sleep naked, that is."

There were a few moments of silence between us, and then she darted forward and tried to snatch the sheet off of me. I struggled to keep it covering me, and though I kept it in my possession there was no way that she didn't get a glimpse at me at various points.

"Hey!" I hissed, finally wrenching the sheet from her as she giggled quietly. "What the fuck!"

"Sorry," she said, laughing, "I couldn't help it. I was curious."

I pulled the bunched up sheet over my midsection and said, "you could have learned that in health class. What the hell did you do that for?"

"Just to mess with you," she said with a grin. "Don't go off and get all pissed at me. I'm just playing around."

"I bet you'd be pissed if I came and ripped your sheets off of you at night," I said, still panting.

"Maybe," she said, and turned and walked out of the room. She paused as she crossed the threshold, grinned, and left.

I was still riled up from Liz's visit when Annie came into my room some time later. Her hair was disheveled and she wore a tight t-shirt and nothing else. She grinned and locked the door, then peeled off her shirt, which I noticed was streaked with cum.

"Hi," she said, crawling onto my bed. "I thought we'd try something kind of fun. Can you straddled my hips, gently?" She then laid down as I got up. I straddled her hips lightly, looking down at her beaming face. Her breasts rose and fell with each breath. She took my erect penis in her hand, gently running her hand up and down.

"You did great this afternoon," she said. "So I thought I'd give you some incentive. If you can last twenty minutes, like this, then I'll let you come on me. But this time, you can pick where."

"Anywhere?" I asked as she gently stroked me.

"Anywhere on me," she said, adding emphasis on the word "on" and smiling. "But I'm going to make it harder for you?"

"How is that possible?" I said, trying to slow my breath and delay the buildup from her gentle stroking. She grinned, and started stroking faster, her breasts swaying with her rhythmic pumping. I gasped and marshaled my thoughts, enjoying the feeling of her hands working me harder, but keeping my orgasm at bay. She giggled, and slowed down, finally stopping but still squeezing my penis gently.

"Like that," she said, grinning mischieveously. "And I'm going to distract you, to see if I can throw off your concentration. When you're with a girl, she might be moaning, or doing something else that turns you on, and you might lose focus. It's got to be automatic for you. So I'm going to tell you a little story while I do this."

"Oh yeah," I asked, running my hand along her stomach. She grinned wider as my hand traveled upward until I was running my hand up the underside of her breast. She resumed her slow, gently stroking as I ran my fingers up underneath and over her breasts. I dragged my fingers across her pert nipples, causing her to sigh as she stroked me. "Tell me," I said, fondling her breasts while she stroked me.

"Remember what I told you about my mom and dad? About me accidentally spying on them in my room, while my mom pretended to be me? After that, well, I was obsessed. I wanted to know more, and how they started. So I tried to spy on them when I could. I didn't catch them for a while, but I kept my eyes peeled. And then, one day, I saw them leave the house, and I knew they'd been in their room for a while. So I went and took a look. Some of my clothes were on the floor, probably peeled off before they did it. And then, on the bed, was a ton of cum."

She was stroking me faster now as I massaged her breasts. She bucked her hips underneath me and I knew she was getting wetter and wetter. Her eyes were alight with that same mischievous look and it took all my mental focus to keep from coming. I let go of her breasts and straightened up, letting her work my dick with both hands and bit the inside of my lip gently as I pushed my orgasm further back into my brain. Annie kept stroking, slowing down a little, and kept telling me her story.

"The bed was covered in streaks of it. I knew they had just finished, and that my dad's cum was all over the bed, and that my mom had dressed up like me for him to fuck her. And then, and I still don't know what came over me, but I stripped off my clothes. I was so wet, and I knew what they had been doing, and that mom was pretending to be me. So I crawled onto the bed, and I rolled around, rubbing all over the sheets, smearing my dad's cum all over me."

Annie started stroking me faster. She bucked her hips and I started slowly brushing my fingers across her nipples, gently squeezing her breasts. A streaky stream of clear, slick pre-cum leaked out of me but I was nowhere close to coming. She stroked me in silence for a few seconds and then locked her eyes on mine. "Are you ready to come?"

"Not even close," I said. She grinned, and kept stroking.

"It was sticky, and wet, and cold," she continued, her eyes closed as she remembered that day. "And I was so wet I started to rub myself off right there in their bed, my entire body smeared in my dad's cum. Cum that I knew, deep down, was for me."

I put my hand on her forearm, stopping her from stroking me. She looked puzzled, but I said nothing and got off of her. I sat next to her, my legs crossed and my dick sticking up and throbbing, and put one hand on her breast and slid my other hand down her stomach. She got the idea and reached over and started stroking me again as I slid two fingers into her pussy until my thumb rested against her clit. She stroked me and I rubbed her clit and fingered her, marveling at how wet she was.

"I came in their bed over and over, until the cum had dried against me and the wet spots on the bed were now from me. And then I got up, put on my clothes, and walked out of the room, only to dash to my own room to come some more."

She was writhing on the bed now, barely stroking me as she was lost in her memories and her building orgasm. I could feel her tighten around my fingers and I grinned as I kept rubbing her and she started to come. She trashed about, biting her lip and trying not to cry out as she came. I kept rubbing her clit until she took my hand and gently pulled it out of her. Then she turned on her side and started to stroke me harder.

"Tell me where you want to come," she said, her voice barely audible as she looked at me with a burning intensity."

"On..." I said, panting, "on your pussy."

She grinned, and spread her legs wide. I knelt between her legs and she reached down and started to stroke me again. Her face was flush and her eyes half-closed, and she ran her other hand up and down her stomach, pausing to feel her tits, before she started talking again.

"Another time, I spied on them while they fucked in the bathroom. Mom was wearing one of my skirts and dad was pounding into her from behind. And she kept crying out 'oh, daddy!' and he was grunting and yelling my name, and then he came. And when he pulled out, he took the underwear my mom had been wearing—my underwear—and wiped himself off. The second they left the house I snuck in and picked them up out of their laundry. And without hesitation, I put them on. I remember gasping as my dad's cum clung to my pussy."

I gasped, and finally erupted. I came hard, my cum splattering all over her pussy as she aimed my dick and stroked. Thick ropes of semen issued forth, landing on her labia and coating everything. The remaining spurts hit her ass and thighs, and when she finished stroking she propped herself up and looked at the mess.

"Wow," she said, "that's a lot." I thought you might be spent after this afternoon, but I guess I underestimated the power of youth."

"Well, it's easy when you've got a hot stepmom," I said, laughing. She laughed, too, and then got up on her knees. She pushed me back gently on the bed, so that she was kneeling between my legs, and she slid her hand down her stomach, slipping over the slick cum dripping off her pussy onto my bed, and started to rub herself.

"Don't worry," she said, seeing my eyes widen with surprise, "I can't get pregnant." Then she started rubbing herself furiously. I propped myself up with my hands and watched her. She rubbed furiously, her right hand a blur between her legs as she cupped her breast with her left hand. "Oh, fuck," she said, coming. Her whole body shuddered, causing her tits to jiggle, and she fell forward, catching herself with her left arm so that her shoulders were down and her ass in the air, her face inches from my spent penis.

Annie kept rubbing as her body shook with the force of her climax. She started to come a second time and this time her arm gave out. Annie landed, softly, against me, her tits between my legs and her head turned to its side. Her face was pressed up against me, her spent and cum-soaked penis resting against her cheek. She started coming harder, grinding her face so that she rubbed against my dick. I felt her soft lips unknowingly brush against it and wanted more than anything to get hard and stick it into her mouth. Finally, with her third orgasm over, she sat up. She had cum on her face and her pussy was a mess of my cum and her wetness. She said nothing, but stood up, leaned forward to kiss me once on the lips, and left the room, stopping to pick up her shirt before heading to her bedroom. I lay in bed, spent, my mind reeling, and a grin on my face.

Chapter 2

I spent the next week getting a handjob from Annie each day. I always reciprocated, either fingering or going down on her in kind. The effect on Annie was apparent. It was one morning, about a week after my first handjob from her, that she was laying on my bed, her pussy dripping wet from several orgasms and my semen drying on her tits. She stretched next to me on the bed, turning to face me with delight in her eyes.