Stepmom Helps Out Pt. 01

"Yes," she said simply. "Right now. I want to see how long it takes right now."

"It's...um, it's a little weird, you know, to just, I guess start."

"Oh god," she said, rolling her eyes and laughing. "It's weird for me, too, okay? You're standing here with an erection, and I'm telling you to go ahead and come. But like I said it's nothing I haven't seen before. Good god, I walked in on my older brother about a hundred times growing up, I know what you boys do. So just go ahead and do it, right now. And then I'll know what I'm dealing with. Just think about whatever and do what you need to do."

"Okay," I said, still unsure of myself. I looked down at her, and she looked up at me expectantly, my dick bobbing inches from her tits. I looked down at her tits, which threatened to escape her sports bra, and how much I'd like to slide my dick between them, and I stepped back, closed my eyes and started stroking. Annie said nothing, but I tried to concentrate on prolonging my ecstasy.

I don't know how long I lasted but soon I felt that familiar feeling of pleasure and realized I was going to come. I opened my eyes in surprise but Annie was still looking right at me as I stroked. I erupted suddenly, gasping as thick ropes of cum shot out toward her. She was sitting far enough away, and strand after strand of semen fell between her knees onto the kitchen floor as my knees buckled and I panted hard. I kept stroking until I was empty, and sat down hard in the chair. I had just jerked off in front of my stepmom.

"Okay," she said, looking at my softening penis, and then at the mess on the floor. "I'd say it works just fine."

"How long?" I asked in a half-daze.

"Not long," she said apologetically. "Three, maybe four strokes. I'm sorry honey. I know that was embarrassing for you. I needed to see how sensitive you were so I could help you. You know that, right?"

I nodded, blushing. I moved to pick up my shorts but she stopped me.

"Wait," she said. "I've already seen it, you don't need to cover up yet. She got up, grabbing a kitchen towel and tossing it on the mess between us. She bent over and wiped it up in one swift motion. She left the room and tossed the towel into the washer, and then returned, sitting down in her chair. It was awkward, as I was wearing nothing but a t-shirt but she was very clinical about it, making it almost like a doctor visit. The weirdest doctor visit ever.

"What were you thinking about, when you were, um, doing it?" she asked cautiously. I averted her gaze but she pressed on. "The deal was I get the truth and you have to do what I say, right? So be honest."

"Tits," I admitted.

"Whose?" she asked. I paused again and she volunteered the answer. "Mine?" When I nodded she laughed and stood up. "Thanks for the compliment. So after you've done it once, can you last longer the second time?"

"I don't know," I said. "I've never tried."

"Try now," she said. "Do you think you can get hard again?"

"Um," I said, "I can try. I guess."

"Just relax and think of something that turns you on. Like tits. In a sports bra?"

I grinned, and decided that she had just given me an invitation to stare at her chest. I did, and she grinned again. I looked right at her tits and imagined fucking them, and I soon I was hard.

"Alright," she said, looking me over. "Can you try again?"

I nodded, and started to stroke. I lasted longer this time. Six strokes. I came again quickly, spurting what little semen I had left toward her. A small glob of it hit her thigh but she didn't react. When I finished coming I looked down, ashamed. I couldn't even last ten seconds longer the second time.

Annie said nothing, but took a towel and cleaned off her leg. She walked over to the counter, her back to me. She said nothing for a few seconds, then turned to face me.

"Sorry," I said. "About getting some on you."

She waved her hand dismissively. "It happens," she said. "I can't tell you how many times I've gotten some on me. Alright, I think you've got a lot of work to do to get over this problem, but I think you can do it."

I blushed, mortified at my dismal performance.

"Probably jerking off in front of your stepmom didn't help things," she said. "I know it's weird, what we're doing. But I'm trying to help."

"I know," I said. "It's just embarrassing. That's all."

"You don't need to be embarrassed. I shouldn't tell you this, but if if makes you feel better I'll tell you a secret. On my fourth or fifth date with your dad, we were making out at my old house, and I decided I wanted to go down on him."

She paused, blushing. "I can't believe I'm telling you this. But, I just asked you to jerk off twice, so I guess it's alright. Anyway, I got it out of his pants, and wrapped my hand around it, and before I even got it to my mouth he came. I wasn't prepared, and he covered my face with cum.

"But I stroked him off anyway, and when he was done he was embarrassed and I had a face full of cum dripping off me. But he was a good sport and used his tongue to get me off so it worked out fine. It wasn't the first time someone had come on my face, but it was the first time I hadn't had a warning first."

I looked down and realized I was hard again. She looked at it, and then thought for a second. "You know those muscles, the ones you use to stop peeing? When you're close to coming, flex them hard. Think only about how hard you can squeeze those muscles. Squeeze them so hard that your whole body tenses up, and see if you can last longer."

"Should I do it again?" I asked.

"No," she said, walking over to me. "I think we can stop for the day. Besides, I'm meeting some friends for lunch. Just think about what I said and practice. Maybe in a few days I'll see if you've improved."

Annie then pulled me up and kissed me once on the cheek. As she did she bumped her stomach against my penis. A smear of cum marked the spot of our collision. She looked at it and then back at me, but said nothing and walked upstairs.

I put on my shorts and then sat back down, thinking. I had just jerked off—twice—in front of Annie. And she had given me homework for the "next time." The idea of a next time set a broad grin on my face.

"Mike..." Annie called from upstairs. I dashed upstairs to find her bedroom door open. I entered, and heard her call my name from the bathroom. I knocked and she answered, "Can you grab me some shampoo from my cabinet?"

"Sure," I called back, grabbing her shampoo. I opened the door to her bathroom slowly.

"It's alright," she said, "the glass is fogged up." Annie and my dad had a transparent glass shower. The room was steamy and the shower and mirrors were completely fogged up, but I could see her curvy silhouette against the shower glass. She reached a hand up to get the shampoo from me, and I could barely make the outline of her tits through the fog.

"Thank you," she said.

"No, thank you," I said. "For the show."

"Ha," she said, "Very funny. Now get going."

I turned to leave but looked down at the counter as I reluctantly turned from her. I saw her workout clothes in a pile by her hair drier. I paused, looking down at the black cotton underwear she had been wearing. They were completely soaked.

I grinned, turning around to get one last look at her before I left.


Chapter 3

A week passed and I practiced holding off my orgasms on my own. Annie made no mention of our "lesson" or if and when there would be another, but I applied myself and tried hard to concentrate on those muscles. At first it didn't' work, and I came right away while trying to thinking about holding myself off. After a few days, though, I was able to last longer. It was the following saturday that I woke up grinning. The night before I had lasted a minute and ten.

I was grinning as I walked past Liz, who rolled her eyes at me and said something rude as usual. I ignored her and headed downstairs. My dad was reading some emails on his laptop and Annie was in the back yard. I headed outside to find her pruning her rose bushes.

"Morning," she said. She had a tight tank top and very short khaki shorts on. She bent over to reach a low branch to cut and her tits practically spilled out of her top. My dick twitched slightly in my pants.

"Hi," I said, eyeing her as much as I could.

"Have you been practicing?" she asked. I nodded, and she smiled. "Good. How long can you last?"

"A little over a minute," I said, smiling. She set down her pruning shears and took off her work gloves. She glanced into the sliding glass doors and saw my dad at the table and Liz messing about in the kitchen. "Can you give me a hand in the shed? I've got a lot of potting soil to carry?"

I followed her around to the side of the yard to the small shed where she kept her gardening tools. She stopped when we were around the corner. She grinned mischievously.

"Alright," she said. "Show me."

"Right here?" I asked, surprised.

"Right now," she answered. She looked giddy. I looked around hesitantly and she said, "we'll hear them open the door, trust me. I want to see your hard work. Some come on."

"But what if they come outside?"

"Then stuff it back into your pants and we'll act like we're getting potting soil," she said.

My hands shaking, I unzipped my shorts and freed my erect penis. She looked at it, and then looked into my eyes as I started to stroke myself. I concentrated, but her tits were right in front of me and her tanned legs and before I knew it I was coming. I hadn't lasted ten seconds.

I looked down at the cum dripping into the grass. I couldn't look at her. Wordless I stuffed myself back into my pants and turned to walk away. She caught me by the arm and stopped me.

"Wait," she said. I turned but still couldn't look her in the eye. It was as if all of my practice had been for nothing. She smiled sweetly, and said, "you really lasted longer?"

"Yeah," I said, still not meeting her eyes.

"Good," she said, and smiled broadly. I looked at her in surprise. She explained, "you're getting over your sensitivity, and that will keep getting better the more you practice. But there's another half of it."

"What's that?" I asked.

"Well, I'm guessing that there's a difference between doing that on your own and doing that in front of someone. Especially your stepmom."

I expected her to say our "lessons" were over, but she surprised me.

"That just means you need more practice in front of me. Maybe you need some incentive, something to work for."

"Like what?" I asked.

"I don't know, let me think about it," she said. "But don't let this get you down. Probably just nerves. Or you were checking me out again."

"Maybe both," I said, and she laughed. I looked over and saw two thick strands of cum splattered on her leg. She looked down, too, and took a towel she had resting on our picnic table and wiped herself off.

"You know," she said, "once I was home from college with a boyfriend, and we did it in the side yard of my house. My parents almost caught us. He didn't get to finish, and had to walk around with a throbbing erection while they made small talk with us. The second my parents' back was turned I stuck my hand down his shorts and relieved his agony. I remember the mess on my hands. So don't worry about the cum, it's not a big deal."

Her cheeks were flush and she suddenly realized what she was telling me. "So about that incentive..." she then reached down and pulled up her tank top. She wore a string bikini that barely covered her tits. She then wiggled out of her shorts and reveal a matching bikini bottom with black and white stripes.

"If you can last longer with me present, maybe you can see me like this more often. Would that be a good incentive."

"Yes," I gasped. "You're beautiful."

Annie blushed. "You're just being sweet."

"No, I'm not," I said.

"Well thank you. See you later, kiddo."

I walked inside to find my dad still perched at his email. We nodded a "hello" and I headed up to my room. On the way I passed Liz, who sneered at me in the hall.

"If it isn't the ten-second wonder," she said.

I just grinned at her and walked by. I heard her fuming all the way down the stairs.

Annie's bikini-clad body must had had an effect on my dad as well because that night, as I lay in bed, I could hear them going at it harder than usual. I sighed as I checked my watch. It was one in the morning when the slapping sounds of fucking stopped coming through my air vent. I was hard, thinking about Annie and how she looked in that small bikini, and I was about to start stroking myself when I heard a tap on my door.

It was Annie. She stepped into the room. I could see in the dim light she was wearing the same bikini, although she and it looked disheveled. I realized with a jolt she probably kept it on while my dad had fucked her.

She sat on my bed, and pulled at my covers. My dick sprang out, and she eyed is musingly.

"All ready to go?" she asked. I sat up next to her. She looked wild, as she had the last time she had come to my room after having sex. I realized that my dad's cum was somewhere inside her, and the idea of it sent my mind reeling.

"Alright," she said, sitting closer to me. "Tell me the truth, did you like seeing me in a bikini all day?"

"Yes," I whispered, and she grinned. "Your father did, too. It's nice to know I can still turn some heads at my age." Then she got up, and twirled once slowly, giving me the full show.

"You look amazing," I whispered.

"And you look hard," she said, sitting back down. "Now, listen, I want you concentrate on not coming as long as you can. But also have fun."

"Okay. Relax, concentrate, and have fun," I said, causing her to laugh. "Anything else."

"Yeah," she said, standing up. "From now on I want to see how long you can last with me close by. No more doing it by yourself. You need to build up some resistance." She grinned as I sat on the edge of my bed. I spread my legs and grasped my penis, and she surprised me by pushing my back onto the bed. She lay down next to me, pressing herself close. Her tits pressed against my arm as I started to stroke.

"That's it, honey," she whispered. "Stroke it, keep going, don't stop."

I gasped, trying to focus. I felt myself close to coming and I concentrated on keeping it at bay. Her body pressed against me was a distraction, and I thought of her soft skin pressed against me and kept stroking. I felt the immediate urge to come subside and started to enjoy the feeling of building up and delaying my orgasm.

"Keep stroking," she panted, pressing harder against me. She pulled me closer and put her leg on mine. I could feel her damp pussy pressed against my leg as I stroked. I kept going as she begged me to keep stroking, and finally I could hold it no longer.

"I'm gonna come," I gasped.

"Then come," she whispered in my ear. We were pressed together and as I came my semen came splattering up my chest. I came in torrents, covering my bare skin with cum as she gasped and giggled in my ear. When I finished coming, I wiped my hand on my sheet and lay there, panting. She sighed happily.

"Well," she said, checking her watch, "you lasted five minutes with a half-naked women pressed against you. How did it feel?"

"Amazing, even better because I could prolong it," I said, still gasping for breath. "Five minutes?"

"Five," she confirmed. She then rolled on top of me so our eyes met. "With me plastered against you."

She then sat up. She was straddling me and her stomach was covered in my cum. She looked down at herself and then at me.

"See you tomorrow," she said, and got up and left me there, exhausted but happy.

Chapter 4

The next morning was Sunday and that meant golfing for my dad. I detested golf and was happy to have my mornings to myself most days. As I headed downstairs I saw Liz on the couch, flipping through the hundreds to mindless channels. We barely acknowledged each other but when I heard footsteps behind me I perked up. Annie came downstairs, her tits bouncing in a bikini as she grinned at me. She reached the bottom of the stairs and eyed her daughter before heading to her purse on the counter. She retrieved a card and approached Liz.

"You've been lobbying to go clothes shopping for weeks," she said. "Don't spend more than 200 dollars."

Liz's eyes lit up as she eyed the card. "Really?"

"Yes, really," Annie said.

"Alright, but the mall doesn't open for two hours."

Annie looked at me and grinned. "Well I'm going swimming," she announced. "Anyone want to join me?."

I waited a few seconds before saying "sure." In minutes I was down by the pool. Annie was already there, spraying sunblock all over her body.

"I was hoping to get her out of the house," she said. "I forgot it's Sunday."

"You could send her to church," I joked. Annie laughed.

"She could use it," Annie said. "But then again, so could I. After all I've been giving my stepson sex ed lessons." She jumped into the pool, surfacing near the edge.

"Well, you're helping me out with a major problem," I said seriously as I joined her in the water. "And I really appreciate it. I also appreciate you plastering yourself against me." I said.

"Oh, that," she said, blushing. "Just getting you used to having a woman around while you're trying to hold yourself off. It's different that just on your own, right?"

"Yeah," I said. "A lot harder to prolong it. But, man, it was intense when I finally came."

"When you get really good at it, you can come and stay hard, and keep going."

"Keep going?" I asked. She nodded, grinning.

"In fact, if you learn how to do that, then there's nothing else I can teach you."

"How do you know all of this stuff?" I asked.

"Well, if you haven't guess it already, I've had a lot of experience. A lot. But most men aren't that great at it. But," she said, pausing. She bit her lip and swam close to me. "When I was nineteen I went to Mexico and stayed with a family there for a semester. It was an older couple, with a daughter my age. The wife, she was pretty nice, but also very religious and I observed her repeatedly denying her husband's advances. One night we had all had a little too much wine and he and I were sitting on the rooftop patio after everyone had gone to bed, and one thing led to another and we did it right there under the stars.

"He was amazing, very talented and patient. He taught me things I had never known before. That first night, he had me spread out as he rubbed me to so many orgasms that I lost count. I begged him to fuck me, writhing in agony as he made me come with his fingers over and over. He knew how to last, and when he finally came inside me for the last time the sun was starting to rise. After that I was at his feet, practically worshiping him, and he fucked me for hours on end. When I came home, I couldn't meet anyone who could last as long as him, until I started teaching them how."

Annie's eyes were lost in the past, but I could see the physical effect her memories had had on her. Her cheeks were flush and she kept absentmindedly touching her stomach and thighs as she treaded water next to me. Suddenly Liz opened the door and announced her departure, startling us both. Annie's attention snapped back to the present and she looked at me with a serious expression on her face.

"Come with me," Annie said, leading me out of the pool. She tossed me a towel and dried off quickly. We entered the house and I grabbed her by the wrist and pulled her close. She pressed herself against me and whispered in my ear as I freed my erection with my other hand "now?"

I nodded, and slipped down my shorts. I held her around the waist, pressing her against me as I stroked myself. I held off my orgasm, and felt the thrill of building up and delaying my own pleasure. Annie was panting next to me, pressing herself against me. I decided to have a little fun and slid my hand down the small over her back. She pressed herself harder, her breath coming in slow, shallow gasps. I slid my hand further down her back until it was resting on the waistband of her bikini. She said nothing to stop my so I slid my hand down further and cupped her ass.