45 comments/ 182733 views/ 384 favorites Stepmom Helps Out Pt. 01 By: TxAuthor Chapter 1 It was well past midnight when I got home from my last date with my now-ex Sarah. I had dropped her off at her house, having resisted the urge to tell her to go to hell and walk home. Getting dumped was bad, but having to drive her home was extra insult. As I pulled into the driveway I shook my head. This was the second time in a year I had been dumped, and for the same reason. I unlocked the door as quietly as I could, hoping to wake no one. I passed my stepsister Liz's door and then turned the corner. As I did I heard the telltale squeaking of the mattress in my dad and stepmom's room. As usual, they were going at it like crazy. I remembered the first time I realized what the sound was, how erotic it was to realize my dad and stepmom were fucking. Now, hearing them night after night for an hour straight only eroded my confidence more. I stepped into my room and shut the door. The squeaking bed was barely audible through my air vent, although I knew they were still fucking. I stripped off my clothes and looked at myself in the mirror. I was a fairly good looking guy, and had always had a steady stream of interest from girls. But now, with two girlfriends in a row, I was kicked to the curb, left to wonder if I'd ever get over my 'problem.' I lay down, trying to shake the feelings that washed over me, listening as my dad fucked my stepmom's brains out for another twenty minutes. The next morning I woke up late. It was Sunday, and my dad was out golfing. I headed downstairs to find Liz eating breakfast with my stepmom Annie. Annie smiled sweetly, her hair disheveled from what I knew was a long night of screwing. Liz smiled at me, a look of glee on her face that I suspected meant trouble. Liz and I weren't close, even though we were the same age and both went to the local college together. Annie fixed me a plate of food and set it on the table. As she did her loose t-shirt fell open and I saw quite a bit of her cleavage. Annie had nice breasts, and I took in as much of them as I dared before looking over at Liz. Her eyes narrowed, clearly having caught me checking out her mom's chest. I knew Liz was insanely jealous of her mom's figure, even though she was pretty in her own right. Both women had blonde hair and bright blue eyes, but while Annie was curvy, Liz was a tennis player with a toned body. I didn't have a 'type', but I thought both women were attractive, and I envied my dad for getting to enjoy Annie on a nightly basis. "How was your date?" Annie asked sweetly, sitting down to join us. I shrugged, not wanting to get into it, but Liz was ready to pounce. "Oh, he got dumped," she chimed in. "Liz!" her mother said. "It's true," Liz said, her eyes alight with glee, "Sarah told me this morning." That, I thought, was what I got for dating a friend of Liz's. I said nothing and ate quietly. It was awkward, and I avoided Annie's eyes. Still, she paused, then cleared her throat and tried to smooth over the situation. "Liz, leave him alone," she said. "Mike, honey, are you alright?" "Yeah," I said, meeting her eyes. She looked sincere and concerned, unlike her bitchy daughter who was grinning. "I guess it just wasn't going to work out."
"That's not what I heard," Liz said, ready to strike at last. I wondered how much she knew, but before I could tell her to shut up she blurted it out anyway. "Sarah said you can't last more than a minute in the sack!" "Shut up!" I said. Annie tried to intervene but I got up, dumped my food in the trash, and stormed out of the kitchen. I grabbed my keys and seconds later peeled out of the driveway to the sound of Liz's derisive laughter. I drove around for a while, blaring the radio and trying to convince myself that Liz was full of it. But she wasn't, and that was what had set me off. With both Sarah, and Kristin before her, each time we had gotten down to doing it I would barely get inside them before losing control and coming. I tried everything I could find to delay my climax, but I couldn't. At first each girl was patient, even understanding, but as time went on I could sense increasing frustration, until they each came up with some lame excuse to dump me. And now they were telling their friends, including my stepsister. If I didn't do something about it, I'd be labeled as the "one minute man." But I didn't know what to do about it. I returned home about an hour later. I was relieved to see Liz's car was gone; I didn't want to deal with her. I entered the house and found Annie sitting on a chair in the living room, waiting for me. "Hey," she said kindly. "Are you alright?" "I don't want to talk about it," I said a little too curtly, then stopped. "Sorry, I didn't mean to snap at you." "Don't be sorry," she said. "Liz was awful to you to suggest that." I felt my face redden. I sat down across from her. She was wearing running shorts and a t-shirt, and her hair was pulled up a pony tail. She was always working out, trying to keep "old age at bay" as she often said. Still, in her early forties, she looked great. I could see why my dad was so attracted to her. I looked up at Annie. She was always there for me, always ready to listen or give me good advice. I didn't think I could tell her exactly what happened, but I didn't have to—Liz did it for me already. "She's right," I said, defeated. "I got dumped because of it." "Surely that Sarah girl isn't that shallow?" Annie said. "Are you saying there's something worse about me?" I said, again a little rudely. I apologized, and she smiled. "It's alright, you're upset. I just meant, well, that's a pretty dumb reason to leave someone as great as you." "Thanks," I said, "but I guess it's been enough for two girls so far. I mean, I can't even believe I'm talking to you about this. But, what if I'm just terrible at it?" Annie smoothed her hands over her shorts and stood up. She walked around the coffee table and sat next to me. She patted me on the leg and smiled. "You can last longer and be terrible at it, trust me," she said with a laugh. "Besides, I'm sure you're exaggerating." "I'm not," I said plaintively. I had always felt close to Annie since she and my dad married ten years beforehand, and my problems just started tumbling out of me. "I'm serious, Liz wasn't kidding." "Well," Annie said, pausing to reflect on what she was about to say, "this is going to sound weird from your stepmom, but you can learn how to....um, last longer."
I looked up at her hopefully, and she nodded. "It's true. I once had a boyfriend who lasted a minute, maybe less each time. But after a while I taught him how to last longer and then everything was great. Better than great, even." "Really?" I asked. "But I mean is there a book I can get, or some kind of instructions. Maybe something online. Anything would be helpful." She shook her head. "Not that I know of. I bet you've already scoured the internet and found nothing useful. It just took some patience, and time." She stood up, bending down to kiss me on the top of the head. "Be patient, it will work out. You just need to find a good teacher." She walked off, her round ass swaying in the hypnotic way it always did, and I called after her "are you sure I can learn?" She turned, grinning. "If your dad could learn how, so can you," she said with a wink, and walked upstairs. I sat downstairs for some time, dumbfounded. If my dad was able to fuck Annie for as long as he did every night, then there was hope for me. I was filled with a sense of possibility, the possibility that the dread I had felt each time I was with a girl would eventually be gone. I was also filled with thoughts of my Annie getting fucked by my dad, the sounds of the bed squeaking and the occasional moan from Annie. If she could teach my dad to do that, then there was hope for me. Of course, there was one catch. I needed to find someone who could teach me how to last longer. It wasn't a skill I wanted to ask for on a first date. Both Sarah and Kristie had been nice enough about it at first, but neither of them had any bright ideas that could help me. If only I could get Annie to tell me how she taught my dad. The second I thought it, I realized that Annie could tell me how to last longer, if she wanted to. I mean, she said she taught my dad, but that doesn't mean she couldn't at least explain what she did. She and I had shared frank talks about everything under the sun, including sex, so what was the harm in asking her? Determined, I headed upstairs. My parents' bedroom had a sitting room off of it overlooking the backyard, and that's where I found her. She was reading a book, and when I knocked on the open door she looked up and set it down on the table next to her. "What's up?" she asked. I took a deep breath, and decided to use every ounce of confidence I had. "Annie," I said. "I want you to tell me how you got my dad to last longer. Please." She paused, a look of genuine surprise on her face, and said gently, "Mike, it's not something I can exactly explain in words. I kind of had to show him how. If I could tell you, I would. But I don't think I can help." My face fell and she noticed. She immediately added, "I mean, it's not like I could actually show you." She stood up and paced around, looking out the window for a minute before turning to face me. "I wish I could help." "Well," I said, trying to lighten the mood with a joke, "you could show me, if that would be more effective." "No," she said flatly, clearly missing my intention at humor. She strode out of the room without a word. Before I could chase after her I heard the front door close. She was gone, leaving me feeling worse than I did that morning. I tried to catch Annie later in the evening when she returned, but she resolutely avoided me. By the time Liz and my dad came home I was starting to worry that I had permanently damaged my relationship with my stepmom. Dinner and the rest of the evening was unbearably uncomfortable, and I wasted no time with a lame excuse to head up to bed early. I sat in my room, reading, trying to get my mind off of my problems with girls and now my strained day with my stepmom. I was so wrapped up in my thoughts that I hardly noticed the familiar creaking of my parents' bed across the hall from me. "Great," I sighed to myself, settling in for another round of my dad slamming into my stepmom. I checked my watch. It was ten-thirty, somewhat early for them. As I read and the steady sounds of fucking came muffled through my air vent, I thought about Annie. She was pissed, that much I could tell. I wondered how I would make it up to her, if I even could. I had clearly crossed a major line with her. Maybe some serious housework would put me back in her good graces. She had wanted my dad to paint the front picket fence. Maybe I could surprise her. My mind wandered and I stopped thinking about Annie and how I could make it up to her, and just thinking about her. She was always funny, and sweet. But she was also curvy and fit and I could see why my dad was attracted to her. The idea of Annie getting fucked nightly was one that was constantly on my mind, and as the muffled sounds of their coupling continued I found myself getting hard just thinking about her. I was just about to slide my hand down my shorts when the sounds from the air vent stopped. I paused, my fingertips just below my waistband, and listened hard. I looked over at my watch and noted disconsolately that it was eleven twenty. My dad had just fucked Annie for fifty minutes, and I couldn't last fifty seconds. I was about to go ahead and jerk off anyway to relieve my stress a little when there was a knock on my door. I pulled my hand out of my pants and sat up. I made every effort to conceal my erection before whispering "come in." A second later the door opened and Annie peeked into the room. "Busy?" she whispered. Her hair was disheveled and she was wearing one of my dad's t-shirts as a nightgown. I shook my head and she entered. I had left the room lights on and as she shut the door I could make out the outline of her underwear and noticed she had no bra on as she turned around. My penis, which had started to soften, was now growing again. I shifted, covering myself a little with a sheet to hide my response. Annie sat down on the bed next to me. Her long, tanned legs were draped over the edge and she leaned back on her hands. I tried not to stare at her tits, but her nipples were hard and I took as many sneak peeks at them as often as I thought I could get away with. "This morning," she said after a moment. "When we talked about...your concern. And you asked if I could show you." I started to speak but she stopped me. I looked at her and I could tell she had something on her mind. Her hair was a mess from getting fucked and I realized that she had just gotten fucked hard and was now talking to me calmly. I wondered if my dad came inside her, and if so if it was it slowly dripping out of her. My thoughts were suddenly brought back into focus as she spoke again. "I don't appreciate your joke," she said calmly. She wasn't angry, I could tell. But Annie was not one to let things lie in silence to creep back up later. "I know you want some help but for god's sake, Mike, I'm your stepmom." "I know," I said, my voice creaking from the strain of whispering. "That's why I asked. I've always come to you with my problems. And when you said you knew how to help, well how could I not ask? You can't dangle that in front of me and then expect me to accept it quietly." She paused, thinking it over. "I'll give you that," she said, "I can't blame you for asking. But you know I can't help you like I helped your father. I mean..." she paused, blushing. "It was not merely a tutorial. It was hands on." She blushed again and looked away, and then started to laugh quietly. I laughed too, although I took her averted gaze as a chance to look at her tits without reproach. When she turned to face me I was a little too slow breaking away from her tits. She looked me over but said nothing about it, and continued talking to me. "So I'm sorry I avoided you all day." "It's okay," I said, "I'm sorry I upset you." "At first I was upset, and then I thought about it, and I realized that it was kind of funny. Not your problem, honey, but what you asked. And then, I'll admit, it got me thinking about it." "Is that why you and dad started going at it earlier than usual?" I asked. She blushed and laughed. We had joked many times about their sex life and she swatted me on the shoulder playfully. "Well," she said, "I guess I had that coming." She leaned back, stretching, and as she looked down she saw, to my terror, my erection fighting against the sheets. She quickly looked away but I could tell she had seen it. I was about to say something apologetic when she sat up and turned to face me. "Alright," she said, "maybe I'm in a good mood because I just got some, or maybe I'm making a huge mistake, but I'm going to help you. A little," she added quickly. "I can give you some pointers, ask some questions, alright? "Okay," I said, unable to say anything else. I wasn't sure if she was kidding, or if she even meant what I hoped she meant. She stood up, stretching slowly and yawned. Her t-shirt rose up and I could see more and more of her thighs until I finally saw the first glimpse of her pink underwear. Her legs were slightly parted and her underwear was soaked through—I guess dad came inside her. She leaned forward and put her arms on my shoulders, looking me straight in the eye. "We'll start tomorrow," she said. "And you're going to have to do what I say, how I say it. Okay?" I nodded, and she continued. "You can't tell anyone about this. And you have to answer any questions I ask truthfully." Again I nodded and she stood up. She put her hands on her hips, and then said "Your dad and Liz will be out most of tomorrow, we can start first thing." She surprised me and leaned in, kissed me on top of the head, and the started to walk out the door. She stopped halfway, and turned around. "See you in the morning." She stepped into the hall and closed my door. I slid my hand down my pants and started to stroke myself; I came before she even made it across the hallway. Chapter 2 I woke up early the next day wondering if Annie had been kidding with me as a way to get back at me. I paced my room for a while until I heard one, then two cars leave the driveway. I changed, pausing twice in the mirror for some reason, and headed downstairs. Annie was waiting for me in the kitchen. She wore tight, black yoga pants and a sports bra, fresh from her morning workout. Her skin glistened and her ample cleavage popped out at me. "In case you are wondering, I was not kidding with you last night. I'm going to give you some pointers." "Thanks," I said, causing her to giggle. "I can't believe I'm even talking about this out loud to you," she said. She hopped onto the kitchen counter, her breasts jiggling as she did do. "I'll ask you some questions while you have breakfast." I fixed myself some food, looking over at her every so often. She looked at me expectantly, but said nothing until I was halfway through my breakfast. "So, um," she paused, biting her lip. "Does it always happen early? And, is it only with a girl, or do you last longer when you're by yourself." "Well," I said, blushing. "This is so weird to say out loud to you. Yeah, it's all the time, doesn't matter if it's just me or with a girl." It was mortifying to say that out loud, but at the same time Annie always helped me with my problems so it seemed natural to tell her. "Okay," she said, relaxing a little. "Anything else about it that's concerning you? You know, like any trouble getting an erection?" "Oh god, no," I said, and she laughed hard. "Everything seems okay. I mean, as far as I can tell. Do you think it's medical?" "No," she said. "I think you're probably just too sensitive down there, plus you're probably overthinking things. Your dad was the same way, at first." "Anyway," she continued, "I'm sure you don't want to talk about your dad." She hopped off the counter, again giving me a show. Her stomach was still flat for a woman her age, and I was pleased by her outfit choice. She sat down on the kitchen table, her legs swaying slowly. "Alright," she said. "I didn't give this a whole lot of thought. I mean, how do you want to start?" "I hadn't thought about it either," I admitted. "I mean, aside from wondering if you were serious." "Super serious," she nodded, giggling. "I don't want you to worry about how long you are going to last with a girl. But, um, I guess to start...well I guess maybe you should go ahead and take off your shorts? You know, so I can look at it?" "Oh," I said. For some reason I hadn't thought she would actually see me naked. I paused, and she laughed, patting her knees gently. "I mean, I've seen plenty of them," she said. "It's not a big deal to me." "How many have you seen?" I asked, feigning outrage. She laughed. "Just shut up and take off your shorts for god's sake, Mike," she said, still laughing hard. I stood up, my hands trembling. I started to fumble with my shorts and started to take them off. She looked at me encouragingly. I was already hard, and as I took off my shorts my dick sprang out, throbbing and ready. Annie just looked at it for a few moments and said nothing, and then looked up at me. "Alright," she said matter-of-factly, "let's see what we're dealing with. Go ahead and try to last as long as you can." "Right now?" I asked, stunned by what she was telling me to do. "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." Stepmom Helps Out Pt. 01 "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. 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. Stepmom Helps Out Pt. 01 "Not this time," she said. "There's something I need to see." Then she wrapped her soft hand around my penis and started to stroke me. Her tits jiggled as she stroked and I felt the familiar orgasm feeling coming on. Confidently I grinned, ready to delay it, when suddenly, without warning, I came. I gasped in surprise as my dick erupted, spilling semen onto her tits and she continued to stroke me. The old wave of terror washed over me, and it was as if everything I learned was forgotten. My penis softened in her hand and she stood up, cum dripping off of her tits onto my bed. She looked down at me and I avoided eye contact. She sat down next to me, putting her cum-soaked hand on my thigh. "I knew you could last longer, and control it, with your hand. I didn't know if you could control it when someone else was in charge of the rhythm and intensity." I looked down but she took my hand in hers and squeezed gently. "You learned how to control it with your hand. Now all you need is to learn how to do it when a girl is actually doing it. And I'm going to teach you." "You are?" I said, finally meeting her eyes. "Yes," she said. She leaned forward, kissing me once on the lips, and stood up. A thick rope of cum hung off her left breast. She picked it up with her fingers and rubbed it onto her stomach. "You know how to prolong it, now you need to concentrate on that while I do the hard work." "Thank you," I said, trying to fend off a rush of emotion. "We'll start tomorrow," she said, winking at me and walking out of the room. As she shut the door my dick twitched back to life slowly. Stepmom Helps Out Pt. 02 Thank you to all the readers who sent encouraging messages. Enjoy part 2 and I'll try and get part 3 out soon! 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. Stepmom Helps Out Pt. 02 "I've never come so much in a day," she said, patting her stomach softly. "Between you and your dad, I'm a happy girl." "Yeah," I said, my hand gently touching her breast. "How many times are you doing it with dad?" "Usually at night, which I know you can hear. But I've been giving him a blowjob job in the shower every morning before I come and see you." We had started openly discussing her sex life with my dad, which would have seemed strange had she also not been stroking my dick constantly. I could last as long as I wanted now, and she had stopped checking her watch afterward days before. I suspected that Annie was enjoying our "lessons" more and more, and my dad was unwittingly benefitting as well. I sat up, looking down at her. She was stunning, and had been more and more open about her sex life. In our time spent along together, she had told me about the first time she swallowed someone's cum, the first time she got fucked, and the first time she took someone's cum on her face. It was erotic to hear her talk about it, and it always got her excited. "Annie," I said, gently stroking her side, "does my dad know all these stories?" "Oh, yes," she said, grinning. "He gets turned on by them. Just like his son." "I think you enjoy telling them as much as we enjoy hearing them," I said. "I'll admit that," she said, blushing. I leaned forward, kissing her breasts gently. She sighed, running her hands through my hair. I pressed my growing erection against her and she wrapped her hand around it, stroking it slowly. "Actually, I had another idea," I said. I kept licking her breasts, paying attention to the space between them. Finally I straddled her chest, my dick in between her tits. She got the idea and grinned. She cupped her tits and held them together while I started to fuck them. "I've been wondering when you'd try this," she said, smiling. I started to fuck her tits harder, watching as the head of my dick popped out between them. Her body rocked up and down as I thrust between her tits, enjoying this new sensation. "That's it, baby," she said in a whisper. "Fuck my tits, come all over me." I was in heaven. She kept talking dirty, begging me for it, and I slid my dick between her tits faster. I kept going, slapping against her tits with each thrust, until I finally started to come. Having already come by her hand that morning, I had little left for her, but what semen remained spurted out between her tits, hitting her neck and flooding her chest. She squealed with delight as I came on her. I kept thrusting between her breasts until she was a sticky mess, and then laid back down next to her as she casually smeared the cum onto her tits with her fingers. "The first time I ever got fucked like that," she said, "I was eighteen, and three boys in my school took turns fucking my tits. By the time there were done I was coated in cum. We were hanging out at the park, and they were all starting at my chest, and were always making comments about them. And, I guess maybe I was a little drunk, and I pulled my tank top down and showed them. And one of them asked if he could touch them, and soon all three were fondling them. Then one of them asked me to suck his dick, and I told him no, but I told him to fuck my tits. So he did. He came pretty quick, and I told them next one do to it, and then the third. After that I had an endless line of guys trying to do that with me." "How many of them succeeded?" I asked. "I lost count," she said. "A lot." She giggled, sitting up. "Once, I was on a science quiz bowl team in college, and I was the only girl. I told the guys if we won regionals I'd let them all fuck my tits, and we won. There were six guys on the team, and let them fuck my tits one by one. I remember they stood around watching, and I was in heaven, waiting for the next one after each one came. When we were done I made them take turns licking my pussy until I almost passed out. Then I fucked one of them after the others left my room. That might be the most cum I've ever had on me at once. Maybe, anyway, it's hard to keep track." She got up, put her sundress back on and stretched. The thin fabric clung to her sticky chest. "I'm going out shopping," she said. "With your cum all over me," she added. She blew me a kiss and left, and I sat in bed, exhausted. Annie called me hours later and told me that my dad was taking her on an overnight trip, and that Liz and I were on our own for dinner. I knew my dad was going to fuck her like crazy the entire night, and probably all of the next day as well. Any remote guilt I might have felt was offset by the shear sexiness Annie was exuding. She would often pull my dad upstairs for an hour or so and then come back down, her hair disheveled and her face blushing. I called Liz and told her, but she was already home. I asked her to order a pizza and she refused, saying I could call if I wanted any. I rolled my eyes, typical Liz. I went ahead and stopped off at a local pizzeria and ordered toppings that I liked and knew she hated. When I got home, I found her sitting on the couch, watching TV. I dropped the pizza box unceremoniously on the table next to her. "That had better not have sausage," she said. "Oh, it's got that, and green peppers," I fired back. "Should have called it yourself." She huffed, opening the box and snatching a piece. She picked off the toppings, tossing them one by one back into the box as she sulked. "So where'd they go this time?" she asked after some time. "Some bed and breakfast across town," I said. "It will be a break from the constant sound of your dad fucking my mom," she said. "I didn't know you could hear them," I said, letting down my guard. "I guess you can, too," she said. We both laughed, despite our best efforts to be enemies. "It's pretty bad," I said. "I can hear them through my air vent." "I can hear them, through the wall," she said. This is gross to even say out loud, but they've even done it in my bathroom. There was evidence." "Evidence?" I asked. "Dried cum on my towels," she said. "And on the clothes in my laundry." "Oh, I see," I said, sitting back. I tried to hide my reaction. It was in fact my cum on those towels, because Annie and I had snuck into the nearest bathroom—Liz's—for a quick hand job. And I was dying to know more about the clothes in her laundry. "On your clothes?" I asked. She shrugged. "It's probably everywhere," she said. "I can't imagine where else they've done it. Don't tell me you're embarrassed," she said, her expression turning hard again. "You know my mom and your dad do it all the time." "I'm not embarrassed," I said defensively. She instinctively went in for the kill, like a shark that detects blood in the water miles away. She tossed her slice of pizza onto the top of the box and stood up. "Maybe you're just jealous," she said. "Since your dad can go longer than you can. Well, anyone can go longer than you can." "Fuck off," I said, returning her glare. "You don't know what you're talking about." "Oh, yes I do," she said, triumphant. "I have it on good authority..."
"That was a long time ago," I said. "Trust me, I can last as long as I want." "Bullshit," she said, laughing at me. "I bet you couldn't last ten seconds." Liz then surprised me by pouncing on me. I dropped my pizza on the floor as she landed on top of me, pushing me back onto the couch. "What are you doing?" I asked. Her eyes were alight. "I'll bet you you couldn't last ten seconds," she said. "Not with a real, live girl." She then reach down and started rubbing me through my shorts. I was instantly hard, and too stunned to do anything. She was grinning, a wild look in her eye. Seconds passed and she was actually stroking me through my shorts, expecting me to come any second. She looked hot on top of me, and her body was pressed against me as she tried to rub me off. I just smiled, put my arms behind my head, and looked at her. She stroked me through my shorts for several more seconds, looking more and more bewildered. "Next time you can just ask," I said, "if you really wanted to get your hands on me that badly." "Shut up," she said, sitting up and straddling my legs. She scowled at me, angry at having been thwarted. "You just lasted longer because it was through your shorts." "Well, I think you've proven your point," I said, trying to knock her off of my legs. She leaned forward to stop me, and reach down with one hand and fumbled with my shorts. Before I could say anything she had freed my swollen member and was now directly stroking it. "Now you'll come for sure, probably before I stroke it ten times," she said, pumping my dick with her hand, her eyes locked on my defiantly. "I've got all night," I said in a relaxed tone. "And you give a nice hand job." She gritted her teeth in anger. I realized that, with my dick in her hand, should could actually inflict some serious pain or injury. However she seemed intent on proving I would come quickly, but I wasn't even close. She stopped suddenly, my dick throbbing as she sat up on my legs. Pre-cum was coating her hand, and her face was flushed. She looked at me, clearly working something out in her head. "Maybe you need visual stimulation," she said to herself. She stood up, and I played it cool and didn't react as she peeled off her clothes. She looked remarkably like Annie, a younger version. Bitchy or not, Liz was hot, and I was enjoying her attempt at humiliating me as much as I was enjoying seeing her flustered. She straddled me naked again, this time she wore a look of triumph on her face. "Let's see if this does the trick," she said, and started stroking me again. She looked so much like her mom, although her tits weren't as big, that I was enjoying myself. As she kept stroking me her look of superiority faded. She now looked puzzled, and defeated, yet still she kept stroking me. We said nothing. What had started off as a hate-fueled tease was now, slowly, turning into a nice way to spend the evening together. "I don't get it," she said, actually laughing despite herself. "I must be doing it wrong." "No, you're doing it right," I said. "I'm not complaining in the least." "Um, thanks," she said, blushing. "I can't believe I stripped down and did this." "I notice you haven't stopped," I said calmly. "At this point," she sighed, "I might as well get you off. This is taking forever, though." "Why don't you suck it instead?" I said. "What?" she asked, her mouth open. "Suck it," I said, my voice low and calm. She paused, sitting up and pushing her hair back behind her ears. "I'm your stepsister," she said, as if that made a difference at that point. "Liz, if you want me to come, you're going to have to suck my dick. Right now." She bit her lip, her cheeks flushing more. Then she obediently lowered her eyes from mine, and then scooted back and leaned forward. Without hesitation she took me into her mouth and started to suck on me as her head bobbed up and down. I sighed slowly, and she laughed but kept sucking. "You're really good at this," I said. "And you take a lot longer that I thought," she said, pausing to stroke me for a little bit. She got up and stripped off my shorts before sitting back down on me. She resumed the blow job and I slowly thrust my hips upward to meet her. "And you look pretty hot," I said. "I mean, you look hot anyway, but I'm enjoying the view." She started to suck me harder and faster. I relaxed, enjoying myself. She straddled one of my legs as she sucked and I could feel her wet pussy against me. I decided to show Liz exactly what I could do, and started to let my orgasm build. When I got closer I decided that etiquette required that I tell her. "I'm gonna come," I said. "It's about time," she said, wiping her mouth. She sat up, stroking me hard, and finally I came. Semen erupted from me, spraying up in the air and hitting us both. She laughed as I spurted cum all over her hand. I concentrated on staying hard, and as she kept pumping my dick I stayed rigid in her hand. She looked down at it but stopped her stroking. I sat up, gently tipping her back into the couch in the process. "Thanks," I said. "That was nice." "You're welcome, I guess," she said, a little flustered. " I can't believe I just did that." "I can," I said" "I'm sorry I tried to make you come to make fun of you," she said, suddenly serious. I looked down and saw a clear drop of wetness slowly dripping out of her onto the couch. "You made up for it," I said, leaning forward. I kissed her, hovering gently over her. She kissed me back, and I pressed my hard, throbbing dick against the entrance of her vagina. "Go slow," she panted, accepting me without hesitation. I slid into her, feeling how tight she was. I continued to enter her until I was completely inside her and could feel her pussy contract slightly with anticipation. "Fuck me," she said. "Fuck me and come inside me." I didn't wait for her to ask again. I started to thrust into her, marveling at how amazing she felt inside. This was better than any blow job or Annie's tits. I fucked Liz and soon she started coming, already close from blowing me. "I'm coming!" she squealed. I felt her pussy clamp down on me and I had to work harder to thrust into her. She was much tighter than the other girls I had been with, and I had lasted only seconds with each one of them. She panted, her body writhing on the couch, and I kept thrusting into her, my balls slapping her ass as I buried myself deep inside her. She came a second, then third time, her cries getting louder as I penetrated her as deep as I could. We fucked like wild animals, the years of animosity working through us. I wanted to make her cum over and over, and I wanted to shove my dick so deep inside her that she exploded. Liz thrashed about, calling herself my "slut" and begging me to come inside her. Her fourth orgasm hit her and her pussy got so tight I couldn't fight off my own climax anymore. I thrust all the way into her as she came, emptying what cum I had left into her. She gasped and laughed at the same time, her breath coming in short, ragged bursts. I pulled out of her, finally spent, and sat next to her as she lay spread out on the couch. "If I had know you were that good, I would have fucked you sooner," she panted. She sat up propped on her elbows, and said "I've never seen someone stay hard. How'd you learn that." "Oh, here and there," I said cryptically. She grinned, and fell back on the couch. "It's too bad I can't spread the word that you're good at it," she said. "You'd have a line around the block. "Yeah, it wouldn't be that great of an endorsement coming from you," I said. "But on the bright side, that means I don't have to share you." "Share me?" I said. "I didn't think you even liked me." She waved her hand dismissively. "Mike, if you can fuck me like that, I'll do whatever you want." She then reached over, picked up her cold pizza, and took a bite out of the toppings she hated. She looked over at me, smiling in a new way. "Do you think you can fuck me like that later tonight?" she asked. "Stay naked and I can guarantee it," I said, running my hand up her leg. She grinned, and sat up next to me. She finished her slice and bent down to pick mine up from the floor. She tossed it onto a plate and sat back down, putting her head on my shoulder. "I'm sorry, for everything," she said quietly. "I'm sorry, too. We've been assholes to each other." "I know," she said, patting my leg. She bit her lip, pausing before she added, "We can't let my mom and your dad know." "That will be part of the fun," I said. She turned, grinning, and kissed me. "I wonder if I can get you hard sooner rather than later?" It was going to be a fun night. Chapter 3 I woke up the next morning grinning and hard. My dreams were full of Liz and Annie and all of the things I had done to them...and planned to do to them. I had overcome my problem completely, and any bittersweet feelings of graduating from messing around with my stepmom were replaced by the endless opportunities ahead of me. I sat up and looked down at Liz as she slept on her stomach. Her ass was slightly in the air, the same way it had been while I fucked her last night for over an hour. She finally begged me to stop because it was too much for her to keep coming, so I pulled out and flooded her ass crack with cum. Now she looked much softer, much sweeter than she had the day before. It was amazing what fucking someone's brains out could do for one's disposition. I smiled to myself as I remembered her saying "Mike, if you can fuck me like that, I'll do whatever you want," followed by the fresh memories of her begging to get fucked harder and harder. She was, like Annie, instinctive and sensual. Like her mother she also had a small bubble butt that made me hard just looking at it. I gently ran my hand along her ass, causing her to stir awake. I wondered if she would be bitchy again but she opened her eyes and curled around my arm. "Good morning," she purred quietly, snuggling close. I ran my hand up her back, up her neck, and gently through her hair. She turned onto her back, opening her eyes and smiling. "God, to think I could have been enjoying you all this time," she said. "Well, you certainly didn't make the idea appealing," I said. "Are you going to make me apologize over and over?" she snapped. Her expression changed, and her eyes narrowed slightly as she looked at me. "No, just pointing out that you've been pretty bitchy over the years. No need to apologize." "Good, jerk," she said, sitting up. "Because I'm not going to. I can't believe I let you fuck me. What the fuck was a I thinking?" She got up and started to leave, but I stood up and caught her by the arm. I held her, firmly but making sure not to actually hurt her. "Let me go," she said. "Liz," I said, "You've got no right to be mad and you know it." She fought against me, but even though I wasn't holding her that tight she did not break my grip on her arm. Her eyes were locked defiantly on mine, narrowed to almost slits of rage. With her free hand she pulled back to slap me, but I caught her wrist. I held both of her arms now and she said nothing, locked in some internal struggle. Then, to my surprise, she leaned into me and our lips met. Liz plastered her body against me as her tongue slipped into my mouth. She leaned back as I kissed her neck, and muttered, "God, I hate you Mike." "No you don't," I said, kissing her fiercely. "You're just mad because you want me to fuck you right now." We kissed and she stopped fighting my arms. Instead, she pressed against me as we stumbled backward until I ran into the wall. "Ouch," I said, rubbing my head. "Sorry," she said, then, turning her expression serious, she said in a bitchy tone, "serves you right, dick." I grinned, and so did she as we understood each other. Then, I turned around, pressing her against the wall. She gasped quietly, sticking her ass out and standing on her tip toes. "You're such a bitch," I said, kissing her shoulder. "Then fuck me like one," she panted. "I'm wet." "Wet for what?" I said, pressing her gently against the wall. I pressed up against her, my throbbing penis pressed against her round ass. "Wet for your cock," she hissed. "I'm ready, baby, fuck me hard. Slam it into me." "No," I said, running my hand down her back as I pressed against her gently. "Please, please fuck me," she begged. "Louder," I whispered. "Fuck me!" she cried out. "Stick that big cock in my pussy and fuck me, make me your slut." I grinned, and guided my dick between her legs. She parted them slightly and stood on tiptoe, waiting for me to penetrate her. She was soaking wet as I slid along her labia. I pulled back until I was at the entrance of her vagina and then bent my knees slightly. Then, with the head of my penis pressed against her vagina, I grabbed her hair gently. She moaned, arching her head and stick her ass out a little more, and then I thrust upward and entered her fully in one stroke. Stepmom Helps Out Pt. 02 "That's it, baby," she said as I buried myself in her all the way. "Fuck my pussy and come inside me." I started to thrust into her wildly. She was pressed against the wall and her ass was sticking out toward me. She grunted with each thrust, plastering herself against the wall as I penetrated her over and over. Liz was beside herself with lust, begging me to fuck her harder, all the while making slight whimpering sounds as I fucked her. "Don't stop," she said, her voice barely a whisper over the sound of my body slapping against hers. "Make me come." "Only if you beg for it," I whispered in her ear. "Make me come, baby, please. Please..." I pushed downward on her ass so that her feet were flat on the ground and I was a little higher than her. I began to thrust in shallow motions, hitting the inner front wall of her vagina. She gasped and cried out suddenly as I kept thrusting, hitting her in the right spot and triggering a massive orgasm. She ground against the wall, as if she was trying to scale it, as her body shuddered and she writhed in pleasure. I kept thrusting, now deeper into her as her orgasm took over and her pussy clamped down in spasms of joy. "Don't stop!" she cried as I kept fucking her. I resumed my original angle and within seconds she was coming again. Her pussy felt different, tighter than ever, and I wondered how much longer I'd last with the added pressure. She was getting tighter and tighter and she cried out again and stood on her tiptoes. I popped out of her as she pressed against the wall and a small gush of wetness came out of her as she flattened against the wall, her breath coming in shallow waves. "Oh my god," she panted, her face pressed against the wall. "I've never come so hard." She kept panting, her eyes closed as she leaned against the wall for support. "Go back inside me and come. Fill me with it." I turned her around, picking her up. She wrapped her legs around me and slowly impaled herself on me. She was tight, and she squealed as I slid all the way into her. I fucked her slowly, enjoying the feeling of her tight pussy. Her wetness was dripping down both of us. I was close to coming and I pressed her back against the wall and fucked her hard, thrusting deep inside her as she ran her hands along my back. "Come baby, that's it," she said as I fucked her harder. Finally I let go and an intense orgasm overtook me. My dick pulsed hard, filling her with semen as I kept thrusting into her. I thrust into her one last time, grinding against her, and felt her pussy contracting as she started to come for a third time. She gasped, and laughed, as we came together, my penis still pulsing semen into her. Finally, spent, I pulled out of her. As I did a torrent of my cum and her wetness spilled onto the floor, which was already a mess. She laughed as I set her gently on the ground. "It's more fun to fuck you if we fight first," she said with a kiss. "But when we're not fucking I think you're pretty sweet." "So if I called you a bitch right now you'd be up for more?" I said with a laugh. She nodded. "Call me one again and I'll suck you until you're hard and then ride you all morning. "As if I'd let a bitch like you anywhere near me..." I said. She grinned, and sank to her knees. By lunch time, I was weak kneed and exhausted. She was insatiable, and, as she said, even pretending to fight with her turned her on. But she was also suddenly sweet, and spent an hour cuddled next to me, just talking. At first we talked about idle things, but as we spent more time together she suddenly opened up to me about many things, including her mother. "I guess I'm a lot more like my mom than I thought," she said, tracing her hand along her thigh as we lay in bed together. "What do you mean?" I asked. "Oh, well, you know how my mom does your dad every night, the way she's insatiable? I guess I'm the same way. I mean, she's crazy for sex." "Are you?" I asked, grinning. "I think you know the answer. But I'm not like her in some ways, at least. Like, you're the second guy I've been with. Mom, well, she's more experienced." "Oh yeah?" I asked, wondering if Liz knew even a fraction of what I knew about her mother. "Yeah," she said. "Once, when I was younger, I accidentally spied on her having sex with my dad and my uncle Jack, his brother. It was pretty gross. Basically a lot of thrusting and moaning. I remember one was inside her and the other in her mouth, and they would switch every so often until they finished on her. My dad and his brother went out and mom fell asleep and I snuck in and saw her, caked in cum. I don't think I'm that crazy. But, somewhere inside of me, I constantly want it. She snuggled closer to me in my bed, her body pressed against me. I could feel her wetness against my leg as she remembered her mom's experiences. "And then, well, I know she and your dad get into some weird stuff."
"Like what?" I asked, intrigued by what Liz might know. "Well, I haven't seen anything, thank god, but I do know she's been walking around here with dried cum on her chest all the time, like we wouldn't notice." I looked at Liz and she looked at me and said nothing, and then we both laughed. We were interrupted by the sound of a car pulling into the driveway. "Ah, that would be our parents," she said, sitting up and stretching. She started to collect her clothes as I stood up to do the same. "When you say it that way," I said, "it sounds gross. You and me, that is." "Oh, come on," she said. "We're step-siblings, and we've only been steps for a few years. Some of my friends have even asked me if we've ever...you know..." "Oh," I said. "Yeah, my friends have asked me, too. They think you're pretty hot." "I am," she said with a grin. "Yes, you are. But you're bitchy, too." "Ohhh, stop," she said, biting her lip and pulling on her clothes. "Or we'll get caught. Come on, they're probably downstairs already." Chapter 4 After Annie and my dad got back it was difficult to keep both women from running into each other. Between hand jobs from Annie and Liz fucking me like a rabbit I was sore all over. I wasn't even close to complaining, but I wondered if I was starting to get too much of a good thing. I also wondered how much longer I'd keep getting "lessons" from Annie. It was several days later, and we were going to grill by the pool for dinner. Liz was out running some errands for Annie, who was in the kitchen, chopping vegetables while my dad got the grill ready. I should have been helping him, but instead I found myself in the kitchen, sitting on the counter while Annie worked. She wore a short sundress and her ass jiggled as she chopped. "Shouldn't you be doing manly things out back near the fire?" she joked. "I'm doing other manly things, like watching you," I replied coolly. "Well, if you're going to stand there and check me out, you can at least dry off the vegetables I just washed. I jumped off the counter and stood behind her. She looked over her shoulder and smirked as I stared at her ass. "I'm flattered to have a young man's attention," she said. "That's not all you have," I said, and stepped closer. I pressed myself against her, my throbbing penis buried against her ass. She sighed, feeling my desire for her through my jeans and her flimsy sundress. "Your dad might walk in here any minute," she said. I looked over her head and saw my dad fiddling with the grill. "Maybe," I said. "Or he could be out there for a while. I reached around and put my hands on her waist. She sighed as I slid them upward, until I was holding her breasts, gently massaging them as I pressed my erection against her. "Stop," she whispered. "He's right outside." I took my hands off her breasts and backed away. She looked over her shoulder at me, clearly disappointed. I stepped closer again and slid my hand under her sundress and over her bare ass. She said nothing as I slid my hand lower, between her thighs, until I touched her wet, slick labia. "Are you sure you want me to stop?" I said, casually, running my fingers along her labia. She was dripping wet, and the heat radiating from her was intense. "Oh, I don't know," she said in a daze. She leaned forward slightly and stuck her ass out more, giving me freedom to rub her the way I wanted to. "You know, you're a good student." "You're a great teacher," I said. "I wish there was more to learn." She laughed, "I would teach you more if I could, because I could use another man around here to..." I gently probed her labia more, tenderly rubbing her clit as I slid my hand forward between her thighs. She threw her hair back, losing her resolve as I gently penetrated her with the tips of my fingers. "Oh, god..." she whispered, sticking her ass out a little more as I gently penetrated her. "I wish I had something inside me right now." I wasn't sure if that was an invitation or not, but suddenly inspiration struck me. I reached over and picked up a cucumber waiting to be sliced. She looked over at it and grinned. "Good idea," she panted as I kept fingering her. "It's kind of big, isn't it?" I asked. It was much larger than any member I could imagine, at least eleven inches long and as wide as my wrist. "I've had bigger," she panted, sticking her ass out a little more. I grinned, and withdrew my hand from her pussy. I took the cucumber, which felt cool in my hand, and gently ran it along her labia underneath her dress. "Bigger dicks or bigger cucumbers?" I asked. "Both," she said. She signed, and leaned forward a little more, and I angled it upward and gently pressed against the entrance of her vagina. She was open a little from having been probed by my fingers, but I was surprised as her pussy slowly accepted an inch of the vegetable in my hand. "Go slow," she whispered, and as she asked I gingerly penetrated her with the cucumber. Inch by inch it entered her, but at last my fingers that were holding the end of it brushed against her labia. She had taken the whole thing in. "Fuck me with it," she begged. "But Dad might come in any moment," I whispered, enjoying teasing her. She bucked her hips and I started to slowly withdraw it from her pussy. Just before I slipped out completely I thrust it gently but determinedly into her again. She stood up straight, trying to clamp her thighs together, but she whimpered and begged me to go faster. I started to fuck her with the cucumber in long, slow strokes, enjoying the sounds of her ecstasy and the flood of wetness covering my hand. "That's it, deeper," she said, begging me to fuck her harder. I obliged, and was so lost in the moment that I almost didn't hear the back door open. "Oh, shit," I whispered. Annie stood up straight and spun around, forcing me to let go of the cucumber. She stood partially in front of me, and as my dad rounded the corner into the kitchen I realized that she couldn't possibly keep that thing inside her. It would fall out and it would be obvious what was going on. As slowly as possible I reached my hand out and, through the fabric of her dress, grabbed the end of the cucumber that was slowly slipping out of her. Annie gasped as she realized I had stopped the vegetable's slow exit from her pussy. My dad was rooting through the refrigerator, making small talk with Annie. Slowly, carefully, I pushed upward, sliding the monstrous cucumber back into her. "Salad almost ready?" my dad asked, still not looking in our direction. Annie bit her, lip, and was unable to speak as I slowly let the cucumber slip out partway before I pushed it back inside her. "Yeah, got a few things left and then we'll bring it out," I said. "Great, steaks are done in ten," he said, and grabbed a beer and headed out back. I slid the cucumber into her all the way and she shuddered. Annie was coming. Her whole body shook and she whimpered softly as her pussy contractions tried to expel the object deep inside her. I pressed it into her, keeping it inside her as she came. With my free hand I reached around her and slipped my hand under her dress and started rubbing her clit. Oh god," she panted. I lifted the back of her dress and started fucking her with the cucumber as she stood there getting her clit rubbed in the middle of the kitchen. She came quickly, harder than I had ever seen her come before. She fell back, and I caught her before her knees gave out. I slid the cucumber out of her and she moaned softly as she felt its absence. I gush of wetness spilled down her leg, and the cucumber was coated in a frothy mess. As soon as she regained her balance she took the cucumber from me and put it on the cutting board. She grinned and started to slice it, finally tossing the slippery vegetable into the salad. She winked, and poured some salad dressing into the bowl and handed it to me. "Mike," she whispered turning to face me. "Please take this outside, and then tell your dad I need a hand in our bathroom." "How much of a hand?" I grinned. She grinned back, and I headed outside, sending my father in for what I knew was going to be a major treat for him. When Liz came home twenty minutes later I was finishing up the grill while my dad "helped out" Annie upstairs. Annie came down first, her legs wobbly as she walked out to the pool. She wore a string bikini that covered little and a huge grin on her face. Liz looked over at me and rolled her eyes. "Don't you think she's a little too old to wear a bikini that small?" she asked in a whisper. "What do you mean?" I whispered back. Annie was walking toward us, carrying a tray of drinks and plates. "Well, let's see," Liz said slowly. "First, her tits are hanging out. I mean, I get it, she's got big ones, but they stand out on their own, she doesn't need to bust them out like that. Second, I mean, come on, her stepson's twenty feet away." "Are you jealous?" I asked. "No," she said quickly, but avoided looking me in the eye. "And third, I think it's gross how she and your dad are always on top of each other." "Like they just were?" I said. "It was obvious to you, too?" she asked. "Oh, here she comes," she added, and straightened up and smiled at her mother. "Hey, you two," Annie said, setting the tray on the table. "Ready for dinner?" "Just about," Liz said, "I'll be right back." She stepped into the house as my dad came out. Liz returned a minute later wearing an equally revealing bikini. It was white and it fit her perfectly. While she was less top-heavy as her mother, she had an exquisite figure. I had been enjoying both women so much lately that I had come to appreciate every feature, every line of their bodies. But with the two of them flaunting everything in front of me, it was difficult to pay attention to dinner. "What's with the swimsuit?" I whispered during a lull in conversation." "Just making sure you have eyes for me only," she said. "You don't think your mom is...?" I began, but she patted my erect penis under the table, squeezing it gently. "I think she's capable of anything. Besides, think about how hard you are right now, and maybe, if you say the right things, you might get to use that on me later." "Like, maybe if I tell you you're the biggest bitch I've ever met?" I asked. "Ooooh, something like that," she said, grinning. We stopped our whispered conversation and looked at our parents, who were busy with their own conversation. I looked at Annie's tits and sighed, just as Liz helped herself to more of the salad. Liz and I barely made it upstairs after dinner before we started "fighting." We reached the top of the stairs before she turned to me and said sharply, "quit following me, asshole." "Quit blocking my way, bitch," I replied. "I live here, too." "I'll stand here all day if I want," she said, suddenly barring me from going any further. Down the hall my dad and her mom already in their room, no doubt fucking again, and a quick glance downward confirmed what I already suspected: Liz was so wet she had soaked through her bikini bottoms. "You'll do whatever I say," I whispered, and put my hands around her waist and lifted her up. She moved with me, jumping up and wrapping her legs around me as we stumbled up the last step and into the hallway. "You're such a jerk," she whispered, kissing me and grinning. "Only because you're such a bitch," I said. "And a slut." "God, I'm so wet," she panted. "Take me right now. I knew if my dad or her mom walked upstairs we'd be caught, but I didn't care. I was like an animal, intent on penetrating her right there against the wall. She wrapped herself tighter around me as I slid my shorts down until my penis was free. "Take me this way," she said, and hopped down. She turned her back to me and pressed herself against the wall, sticking her ass out a little and pulling her bikini bottom to the side. I pressed my body against hers and whispered in her ear, "I bet you've been waiting for this for hours." "All day," she sighed as I gently penetrated her. I slid all the way inside her, so that our bodies were plastered together. "Fuck me right now, fuck your little slut." I slid almost entirely out of her, so that only the head of my throbbing member was inside her. I gently tugged at her bikini top, untying it. I did the same to her bikini bottom, letting them both fall to the ground as I entered her fully again. "What are you doing?" she said in a slight panic. "If they come out, they're already going to see me buried deep inside you. I thought I'd make it even harder to hide if we get caught." She clenched her vaginal muscles around my dick, her excitement building as I started to thrust into her. "Fuck me hard, then," she said, darting one of her hands between her thighs so she could rub her clit while I fucked her. We made little noise but the idea that, three doors down, our parents were fucking each other added to the fun. The terror of being caught, thrusting into my now-naked stepsister, added to the danger, and soon Liz was coming. "That's it," she panted, "fuck my pussy harder, fuck me..." she was incoherent, her whole body shuddering as she came. I was so ready from the entire day's teasing that her pulsating vagina was too much for me and I exploded inside her. I thrust deeper into her, flattening her against the wall as I emptied my semen into her. I focused on staying hard and kept thrusting into her, any sense of danger gone now, just animal instinct to shove my dick into her as deep and as hard as I could. Liz was coming again, her hand a blur as she rubbed herself faster and faster, until a third orgasm overtook her and she started bucking backward against me. "Oh, oh," she said a little louder than she should have. She put her hand on my stomach to stop me from thrusting and we tenderly disengaged. She bent down, and picked up her bikini before she kissed me tenderly. "I think I love you," she whispered in my ear. "But I like it better when you call me a bitch." With that she winked, and stepped into her bedroom, her legs shaky as she walked. I stood there a minute, my shorts down by my knees and my penis erect. I kicked off my shorts, tossing them into my bedroom and walked down the hall. I put my ear to my dad and Annie's door, listening. The door was left slightly open and when I looked in I saw my father passed out on the bed, spent from fucking Annie. Annie was standing in front of the mirror, brushing her hair. "Annie," I whispered. She looked up, startled. She turned around quickly, heading to the door. She opened it and stuck her head out, whispering to me. "What are you doing here?" she said. She looked surprised, but not upset. She was naked, and I looked down and saw a trail of cum running down her thigh. "I need you, right now," I said, grinning. My dick was still hard, although the mess from fucking Liz was drying quickly. Stepmom Helps Out Pt. 02 "Not here," she whispered, but I took her hand gently and entered the room. She stepped backward, looking at my sleeping father. "Your dad might wake up." "I bet he won't," I said, and took her hand and wrapped it around my throbbing penis. Instantly she was mine, and she pressed her body close and stroked me. "Tell me what you want," she said, stroking me with both hands as we kissed. "I want you to come." "Then suck it," I said as forcefully as I could without sounding mean. She looked up at me for a second, her hands still wrapped around my swollen penis. "No," she said, lowering her gaze. She continued stroking me. "Think about everything I've learned," I whispered, gently holding her close. "Think about how much fun we had in the kitchen." "No," she said, still not looking at me. I took my free and and gently lifted her chin so that we were looking right at each other. "Suck it," I whispered, "Do it right now, on your knees, while your husband sleeps six feet away. Do it before he wakes up and catches you with his son's dick in your mouth. Suck it like your mom sucked your dad, while she called him daddy. Teach me." She broke into a grin and slowly sank to her knees. She looked over at my dad, sprawled out on the bed and sleeping heavily, and then up at me. The view, with her eyes looking up at me and my dick in her hands, was something I had dreamt of for years. "Come for me, baby," she said, slowly stroking me. She licked the head of my penis, swirling her tongue around it several times as she gently stroked me. I ran my hands through her hair and sighed as she swirled her tongue one last time and then took the head of my penis into her mouth. "Mmmm," she moaned softly as she sucked me. She took me slowly into her mouth as I threw my head back tried not to buck my hips. I grinned as I looked down and saw my dick sliding into her mouth as she bobbed up and down on it. I thought of my dried cum and Liz's dried wetness that had covered it and grinned even more. "Enjoying yourself?" she whispered, seeing the look of glee on my face. I nodded, and she grinned and continued sucking. She started rubbing herself with one hand as she picked up the pace and sucked me faster. She stroked me with one hand and herself with the other, all the while sucking me faster and faster. "Oh, god, that's it," I said, watching her tits sway as she sucked me. I wanted to cover her with cum and mark her for the slut I knew she was. I was getting close and so was she, and finally I was unable to contain myself anymore. I gasped and she understood and starting to stroking and suck me faster. I thrust gently into her mouth and came. I had just fucked Liz half an hour beforehand but I came hard in Annie's mouth. My knees buckled and she kept stroking herself as I filled her mouth with cum. She leaned back, letting me slip out of her mouth as she fell back on one hand and stroked herself. She looked up at me, cum dribbling out of her mouth, and swallowed. What little cum that had escaped dripped onto her tits as she started to come. She spread her thighs wider and started to rock her hips back and forth. "I'm coming, baby," she whispered, her hand rubbing furiously. I was worried suddenly that the sloshing sound of her hand might wake up my dad, but he was still asleep as she came. I watched her breasts jiggle as she rubbed herself harder, and then, her orgasm ended, she sat down hard. She panted, looking up at me with wide eyes and cum dripping off her chin. "That was amazing," she said, wiping her chin. I helped her up, and she hugged me. She was unsteady on her feet, and I held for a moment as she regained her balance. "You'd better get going," she whispered, gently squeezing my spent member. She walked me to the door and down the hall. I stepped into my room and she gave my dick one last, gently squeeze. "Oh, by the way, I have so much more to teach you. Stepmom Helps Out Pt. 03 I sat in my room, upright in bed, as the sun came up. I was naked, motionless as my mind raced through the prior evening over and over. I had finally gotten a blowjob from Annie, my stepmom. Of course I was fucking my stepsister Liz like crazy, but I had finally gotten Annie to suck me off. And I knew it was only a matter of time before I would get her to do it again. With some convincing I could probably even get inside her. I grinned, watching my penis slowly swell up and harden at the thought of my cum spurting into her mouth and pussy. Or Liz's, it seemed like it didn't matter anymore. Even though I had strong feelings for Liz, my lust for her mom was clouding my vision. I was brought out of my reverie by a knock on my door. I hurriedly pulled the blankets past my waist and sat up, hiding my arousal. I was glad I did, for seconds later my dad entered the room. It seemed foreign to see him there, after his wife had strode in so many times only to get covered in my semen. But there he was, the husband of the woman who was stroking and sucking me off daily. I felt guilty for the first time since the whole thing began. "Hey, Mike," he said, leaning against the door frame. "Did I wake you?" "Nah," I said, stretching. Dad was wearing a bathing suit and t-shirt. He has a healthy tan and sandy hair, and he always carried himself with a confidence I envied. "Well, we haven't spent much time together lately. I've been immersed in my work." And I've been immersed in your wife's tits, I thought guiltily. "Yeah," I croaked. "We should spend some time together." "Good," he said, grinning his easy smile. "Get dressed and meet me downstairs. I've got food packed already." "Where are we going?" I asked, bewildered. "I thought it would be fun to take the boat out on the river. I'll even let you drive it this time." I grinned. My dad's "little boat" was a pretty nice fishing boat. He had never let me drive it before, or anyone else for that matter. "Are you sure?" I asked. "I think you know what you're doing," he said with a smile, and strolled down the hall. I got dressed, feeling terrible for betraying my dad's trust just as he was trusting me with something. I was halfway dressed when Liz popped in to see me. "Good morning," she grinned, kissing me and putting her arms around my neck. "Watch out," I whispered, "the door's open." "I don't like sneaking around like this," she pouted. "Well I don't know if we can just tell our parents about it," I said. She nodded. "Maybe I'll talk to dad today, if it seems like I can bring it up. We're going out on the boat." "Cool," she said. "I'm going to Sarah's to hang out. You can have some time alone with him, maybe drop hints about me, you know, see how he reacts." "He's letting me drive the boat," I said, grinning suddenly. "Wow, a whole new world," she joked. "Don't crash it into the bank or he'll never let us date. Well, have fun," she said, pecking me on the lips. "You too," I said, watching as she headed down the hall to her room. I crammed some breakfast in record time and met my dad outside. He was leaning against his car, baseball cap pulled low and his arms folded across his chest. "Ready?" he asked. "Yeah," I said. "Okay," he nodded slowly. "One last thing, I hope you don't mind if Annie tags along? I've been promising her to take her out of the river for a week or two. But I'll still let you drive the boat." At that moment the front door opened and Annie appeared. She wore a black bikini that accentuated her curves perfectly. I tried not to stare, conscious of my dad standing behind me. When I turned to face him he was grinning, although I couldn't tell if it was at me or her. We drove for fifteen minutes until we reached the dock. My dad and Annie's boat was ready to go once we put lunch on board. Annie sat on the deck, her head thrown back as she sunned her face, while my dad showed me the ropes of driving the boat out of the dock and navigating the marina. I felt guiltier by the second, as my dad was entrusting me with his pride and joy, and as I kept sneaking glances at his wife. Of course the fact that I was secretly with her daughter didn't help things. When I had the chance, I'd have to ask Annie for advice on how to juggle all of this mess. I steered for a while down the river, past other boaters who were also out enjoying the sunny day. The sky was cloudless and Annie kept turning, tanning herself from different angles. I was sneaking glances and getting hard each time. Meanwhile dad was showing me the ropes, pointing out where to steer and helping me get a feel for the boat. "Not bad," he said, nodding to me as I avoided a smaller fishing boat. "I should have let you try her out sooner." Annie turned and lay on her stomach again, her round ass sticking up slightly in the air as she tanned some more. She reached behind her back and pulled at the string tying her top together, letting it fall to the sides so she could tan her back. I snuck glances at her breasts, which spilled out from her sides as she tanned herself. Soon afterward I could see she had fallen asleep, her head to one side an her mouth slightly open as the wind blew her hair about. We were approaching a major fork in the river and my dad leaned over and said over the engine noise "turn left." We headed down a fairly deserted stretch of river. It was narrow, and my dad navigated me through a second turn until we were alone on a quiet stretch of riverbank. The river was slow here and we could see alligators just on the edge of the water. It seemed like another world, primeval and old. "You're doing a good job, Mike," he said. "Pull closer to the shore, but watch the channel marker though, and we can drop anchor for a while and enjoy the peace and quiet." He looked over at Annie and smiled, "the engine usually puts her to sleep," he added as he sat back in the chair next to me. "I had planned on making this a father-son trip," he said in a low voice once I cut the engine. We were anchored near the shore around a sharp bend, but no one else was on this stretch of river so it was completely quiet, save the bird calls. "But I didn't want to tell Annie that she couldn't come along. Besides, she adds a lot to the scenery." I wasn't sure if I should laugh or not but he nudged me with his elbow, "it's alright, you can loosen up. I know you think she's attractive. Hell, I'd be worried about you if you didn't." I laughed nervously, not sure how to react at all. My dad sat back and looked at Annie longingly. "She is beautiful, don't you think, Mike?" "Um, yeah," I said, trying to sound casual. "Yeah she is." "I mean, look at that ass," he said through gritted teeth. "It's enough to give me a heart attack." "Dad?" I said, but he kept talking. "Annie's ass, wouldn't you agree? I mean, look at it, it's pretty amazing. Not too huge, but nice and round. Go ahead, take a good look and tell me what you think." He nodded and looked over at Annie, and I did so as well. She was still asleep, her face buried in the crook of her arm. I looked her over, this time overtly, and nodded. "Yeah, it's pretty nice." "I'd better wake her up, though, she'll fry if she stays like that all day," he said, and he stepped over and gently tapped Annie on the shoulder. She stirred, then propped herself up slightly. I could see most of her tits spilling out onto the deck, although her nipples were still obscured from view. I looked at my dad, who looked at me and grinned. "She has nice tits, too," he said with a grin. "Jason, not in front of Mike," she admonished in an unconvincing voice. "Just admiring the show," he said with a chuckle/ "Were you two staring at me while I slept?" "Maybe," I said, causing my dad to laugh hard. Annie lay back down on the deck and wiggled her ass a little bit. "Can one of you boys put some lotion on my back? I don't want to burn." "Mike can do it," my dad volunteered immediately. He tossed me a tube of sunblock and cracked open a beer for himself. "You sure?" I asked. "Yes," they said in unison. I paused, but my dad nudged me forward with a nod and a smile. I knelt next to Annie, and squeezed a liberal amount of sunblock on my hands and proceeded to massage her back with it. She sighed, swaying her ass a little as I touched her. I was conscious that my dad was watching, and I wondered what on earth was going through Annie's mind a that moment. I could feel myself getting harder, my erection threatening to spring up and reveal itself through my shorts. I looked over at my dad, who just nodded and sat back in his chair. I worked the lotion down her back slowly, enjoying myself as I innocently—at least in my mind—put sunblock on my half-naked stepmom. I got closer and closer to the top of her ass, each time fall just a fraction away from touching it. I ran my hands down her side and up toward her arms, casually brushing the sides of her breasts as I did so. "Don't forget my legs," she said, spreading her legs wide. I put my lotion covered hands on her and was surprised that they were trembling. She sighed at my touch and I looked over at my dad, who seemed at ease as if he was reading the paper or watching a golf tournament. My hands moved up her legs, rubbed her inner thighs slowly. Annie seemed to enjoy the attention, and spread her legs further. I got closer to her ass and as I slid down to her inner thigh I was inches from her pussy. She suddenly lifted her head up, turning to face my dad, and said, "do you mind if he gets all of me?" "Of course not," Dad said, nodding calmly. Annie then reached behind her back and tugged at the two ties of her bikini bottom. In seconds they were undone and she lifted her hips slightly as she whisked her bikini off completely, tossing it aside. "Back to work," she said, putting her head down. I stared as her bare ass, then looked over at my dad, who nodded. "It's not like you haven't seen it before," he said. "A woman's ass, that is," he added. "Oh," I said, trying to act cool. Annie wiggled her ass slightly, waiting for me. I put lotion on my hands and started at the small of her back, then slowly, enjoying the moment, I slid my hands up the slope of the top of her ass and all the way down. I began massaging her ass, losing myself in the thrill of touching her like this. She sighed, spreading her legs a little more. I took a quick peek and saw, to my delight, that she was dripping wet. I kept massaging Annie's ass, feeling the pre-cum drip inside my bathing suit as I touched her. I ran my hand down her ass and between her thighs, just an inch or so from her wet pussy, and I was about to see how close I could get when my dad finally spoke. "Don't forget to get her front," Dad said as it if was nothing. Annie suddenly flipped over, her tits on display and her legs spread slightly. I could see her arousal on every inch of her body. "Come closer," she said, beckoning me to her. I moved closer, closer still, until my ear was right to her lips and she whispered, "have some fun...he knows." I sat bolt upright and my dad laughed. "The cat's out of the bag, huh?" "Dad, I can't explain!" I said, suddenly short of breath. He held up a hand to stop me and waited a few moments before he spoke. "Relax," he said. "I'll do the explaining. But first put some lotion on your stepmom, I don't want her to get a sunburn." "Start with my tits," she said in a sing-song voice. I did as she instructed, essentially feeling up her tits in front of my dad. My mind reeled as I spread lotion all over her front. I cupped her breasts, feeling her hard nipples against my fingers. "You see," my dad said in an almost philosophical tone, "when you and Annie first talked about your, um, your problem, she told me. And I knew exactly where you were coming from." As he spoke Annie took my hand and let it down to her pussy. She used my fingers as a toy as she brushed them against her pussy. I was too dazed to register what was going on at first. "When I was your age, I had the same problem. I could last a minute, tops, but usually much less than that. And it was humiliating...to the point that I almost gave up on sex entirely. Your mom and I, well it was always a sore point and probably the main reason she left me. But then I met Annie, and she taught me how to keep from coming to soon." "And to stay hard all night," she said, sighing as I continued to rub her breasts gently. "And I know you asked her for pointers," he said. "You know?" I said, stunned. "I know you've been up to a whole lot more, too," he said. "But, Dad, listen," I began, trying to explain everything. "Stop," he said, his voice still a whisper. "I know because it was my idea. Well, mine and Annie's, she gets half the credit." "Your idea?" I asked. "The lessons," he concluded. "She told me about your problem, and, well Annie's a good teacher, I can vouch for that. She was into it and so was I. In fact, I've been enjoying hearing her tell me about it." Annie was rubbing my fingers against her pussy faster now. They were covered in her wetness and I looked down to see her getting closer to an orgasm. Her tits jiggled and her eyes were closed, but I knew that face. "I didn't want my son to suffer as I did. Besides, we had talked about her taking on another man, but I couldn't bear the idea of some random asshole getting in bed with my wife. She told me about how she used to take on two, sometimes three men at once, and I always wanted to enjoy that with her. When she approached me with your problem, it seemed like the perfect solution. "I can't believe it," I said, looking from my dad to Annie. She was stroking faster now, and let out a low, guttural moan as she started to cum. She rubbed my fingers across her pussy harder, doing all the work and using my hand like some kind of dildo. I didn't resist, I was too paralyzed to do anything. "In fact I watched her suck you off last night," he said with a grin. "When you thought I was asleep. Of course she knew I was awake. She's always enjoyed performing in front of an audience, but I guess you knew that already." Annie started coming again, this time she moaned loudly. No one else was in sight and she cried out as she bucked her hips hard, her whole body thrashing as she came. She let go of my hand and sat up slowly, her legs spread and her pussy wide open with arousal. "Enough talking," she panted, her eyes narrowed to slits. "I need to get fucked, right now." "What do you say, Mike?" Dad asked me. "Do you want one last lesson?" "But," I said, then stopped. In truth I had no idea what I was going to say. "Let me show you," he said, standing up. He untied his bathing suit and slipped it off. He was, like me, hard and dripping with excitement. He knelt next to Annie and gently flipped her on her back. She stuck her ass up instinctively and he slowly slid into her as he lay on top of her. Then he positioned himself so he was thrusting essentially straight down, hitting the front wall of her vagina with each powerful thrust. "Oh fuck," she cried out. "Harder!" My dad obliged, thrusting into her so hard that her ass jiggled with each thrust. Soon she started coming, and I could tell from her face she was coming hard. She cried out, almost a desperate howl as my dad kept pummeling her pussy. He kept at it for two more of her orgasms before he pulled out of her. He was still hard, still hadn't come. "Annie," he said, panting. "How about letting Mike try that move." "Oh god, please," she said, barely able to form the words from her delirium. "Go ahead," my dad said, gesturing to her ass, still sticking up in the air. I paused, and my dad asked Annie, "can I tell him who taught you that move?" She nodded, barely able to speak. Dad turned to me and said, "her dad." "You mean when she spied on him and her mom?" I asked. "No," he said, grinning. Suddenly I understood more about my stepmom than ever before, and I grinned and slipped off my bathing suit. I gently got on top of Annie and guided myself inside. She was wetter than I could imagine, and she slowly guided me until I was at the right angle. "Okay," she said, regaining her senses, "now fuck me hard, slam it into me, baby." "Do it," my dad said, "fuck her." "And come inside me," she said, her voice almost hoarse. My dad nodded and I started to fuck her. I had already learned to do it this way with Liz, it was the same thing as fucking her up against the wall, and I could see both women liked it the same way. I fucked her hard, listening to her moans to get the exact angle right. In the meantime my dad moved and sat in front of her, his legs spread and his dick right in her face. She engulfed it without hesitation, sucking him as I fucked her. "Oh, Mike!" she exclaimed, her mouth full of my dad's dick, and I felt her pussy contract with another orgasm. She kept bobbing up and down on my dad's dick as I fucked her to orgasm after orgasm. My dad ran his hands through her hair, calling her his little slut. She called him daddy and begged for his cum. The whole thing was surreal and helped keep my own orgasm at bay for some time. Finally I was close, and as Annie stopped sucking my dad to cry out through what must have been at least her tenth orgasm from me, I started coming. I flooded her pussy, emptying all my lust into her as she writhed against me. I pulled out, completely spent, and she started sucking my dad again. "Not bad, you lasted a long time," he said. "You taught him well, Annie." She didn't respond, but kept sucking him off. She bobbed up and down like a wild animal, actually grunting slightly as she took him deep into her mouth. "Keep going, baby," he panted, his face flush. Annie kept sucking and he moaned and emptied his cum into her mouth. She caught it all, still bobbing up and down until she sat up and swallowed. She wiped her lips and surveyed her sweaty body and the river of cum dripping out of her pussy. "I haven't fucked two guys at once in a long time," she said, grinning. "I think you just graduated, son," my dad said. He sat back, his spent penis now being licked all over by Annie. "Would you mind driving back, I'm beat." By the time I got back home my dad and Annie had hurried upstairs to fuck their brains out some more. I was oddly relieved, knowing that my dad was behind the whole thing. It made the guilt—most of it anyway—vanish. It was several hours later when Annie emerged from the bedroom, her hair a wreck and her clothes put on hastily. Liz was still gone with her friends, and I was in my room reading. Annie came in, knocking and stepping quickly to sit next to me on the bed. "You okay?" she asked. "Yeah," I said. "Well, still stunned." "We wanted it to be a surprise," she said. "Did you have fun?" "Of course I did," I said. I sat up, searching for the right words. "Annie, can I ask you a question? Did you really fuck your dad?" "That's what I came to talk to you about," she said. "Yes. I won't sugar coat it. I fucked him. Many times. My mom knew, she was always in bed with us. I think it was inevitable, really, they way they fantasized about me. One day I just surprised them, and while they tried to stammer an explanation, I joined them. They were too stunned at first but I just started sucking my dad's dick until he came. He had been fucking my mom from behind, the way you two were doing me today. That was the first time I tasted a dick that had just been in someone's pussy." She paused, then said, "and that's how I know about you and Liz. When I sucked you off last night, it was unmistakable. You two had just been together, right?" "I...I'm sorry," I said. "We wanted to tell you," I said. "But, I didn't know how." Stepmom Helps Out Pt. 03 Annie said nothing, but she stood up and suddenly looked very parental for once. "Is it just fun or are you serious about her?" "I'm serious about her," I said. "I really care about her," I said. "Then today was the last day with you and me, okay?" I can't let you hurt her. She can't find out about what happened. I don't want to mess her up." "Mess what up?" Liz was in my doorway. She was twirling her hair and looked very curious. "What did I miss?" "Oh, I was just telling Mike..." Annie said vaguely, searching for an excuse, but Liz cut her off. "I know, mom." "Know what, Liz?" Annie asked innocently. "I know you've been teaching Mike how to, um, how to last longer. I mean, it didn't take a genius to figure it out. After all, you two have terrible poker faces...and body language." "You knew," I asked, stunned. "Sure, I didn't mention it because I figured it was embarrassing. Besides, I'm the beneficiary of all of this, in a way. So now that we have that in the open, I can tell you that Mike and I are dating." "I just told her," I said, laughing. Liz laughed, too, and so did Annie after a few seconds. "I can't believe you fucked your stepson," Liz said, teasing her mother. "Liz!" Annie said. "Hey, I read your diary, mom. It's cool. This is like old hat for you, right?"
"I'm not sure how to respond to that, to be honest," Annie said. "Well, isn't this better?" Liz asked with a smile. "Mike and I don't have to sneak around anymore. I guess, unless your dad will freak out." "I doubt it," Annie said. "Oh god, you two both fucked her on the boat, didn't you?" Liz asked. "I'm not sure if I'm grossed out or turned on. Or maybe I'm grossed out that I'm turned on." "Liz," I said. "It's just you and me, from now on." "Yes," Annie said. "Definitely. And he's ready to show you a thing or two, I figure." "Oh," she said thoughtfully. "Thanks, mom." "Um, you're welcome," Annie said awkwardly, causing Liz to laugh. "Now, if you'll excuse us, we have a date," Liz said. She led me out of the house, and we got halfway down the driveway before she turned and started kissing me. "Tell me everything," she said between kisses. "And then stick that hard dick in me until I beg you to stop." "Right here, in the driveway?" I asked. "No, you're right," she said. "Let's just go out back to the pool. I figure mom's going to be busy for a while with your dad." And with that Liz reached down and unzipped my pants, freeing my erect penis as she led me to the backyard and a waiting deck chair. END