It was the middle of summer, and I was floating in the pool, feeling lazy. I had graduated from high school and had three months off before I went to college. I was intent on doing nothing, if possible, because I knew my days of freedom would end soon. In just a few short years I'd start my career, working for those two weeks of paid vacation that paled in comparison to this one, last summer.
I was in a foul mood. It was just the fleeting summer days. My mother's best friend, Laura, with whom I had lost my virginity and had fucked several times afterward, had a boyfriend. He was new in town, a computer programmer or something along those lines, and she has stopped seeing me as a result. She had me over for dinner, had broken the news, and had given me a parting handjob as a consolation prize. I had come all over her tits and neck, and then went home to sulk.
Worse than losing Laura was losing Jen, my step mom. She had set me up with Laura, without telling me, and when I had found out, I had lashed out at her. Yes, I had gotten laid, so I might sound like a whiner, but I believe that she should have asked me first. If the genders were reversed, and a stepfather lent out his stepdaughter to a friend, it would be worse, I had said. And That's when I discovered something amazing about Jen. She likes to give blowjobs. Either to settle a bet, or on a dare, or when she felt guilty for setting her stepson up for some attachment-free sex for a friend. She had sucked my dick three times. Twice on the first night she took me into her mouth, and a week later, when she was feeling particularly guilty about Laura propositioning me. That sweet, final time, I had exploded in her mouth, but she sucked every drop of cum and swallowed it all. Since then I had been hoping she would do it again, with no luck. Now, with Laura moving on to new things, I had no chance.
Or so I thought.
The thing about life is that one door closes, and another opens. Cliché, I know, but it's true. At least for me, it seemed. My friends were already starting to go their separate ways toward college, and I found myself with more free time than I had bargained, and that's when things got interesting again.
I was drifting in the deep end, and into a nap, when I heard the sliding door open. Jen, my stepmom, exited the house and walked along the pool edge. I tilted my head up for a better view. Jen preferred one-piece swimsuits, because she felt that she had "too much tits for a bikini," which was the most absurd thought I'd ever heard. She did have fantastic tits, and a firm body. Her short, sandy hair flopped in front of her eyes as she walked.
"Hey there, lazy," she said teasing me. She slipped into the warm water and I slid off the float and swam closer to her. Since the blowjobs I found myself wanting to be as close to her as possible, and I tried hard to fight that instinct, so I wouldn't crowd her or freak her out. "Have you been out here all day?"
"No," I replied, sliding past her in the water to get a good look at her ass when her back was turned. "I got up at noon."
She laughed and swam around for a bit while I sat on the pool steps in an attempt to hide the erection in my bathing suit. It was automatic these days when I even thought about Jen. Laura had been amazing, a hot woman desperate for attention. Jen was something more. It was erotic, and wrong, and that made it even better. Still, all attempts to bring the up the subject failed. It was as if she was oblivious to any hints. I kept at it, though, in hopes I'd succeed.
"Are you ready for our trip?" she asked after a while. We were heading to Georgia for a wedding on her side of the family. With my dad gone, it was just the two of us, and I was often Jen's "date" for weddings and other events. I had always enjoyed going with her, because Jen was fun. But now, the idea of a trip with her carried new possibilities, for fulfillment and disappointment.
"Yeah," I said. "I'm going to pack last minute, as always. But I'm ready."
"Good. Are you sure you don't mind sharing a hotel room with me?" she asked.
"Of course not," I said, trying desperately to sound detached from the idea. "Unless you plan on parading about naked when we're alone, because that would be the worst," I said sarcastically.
"I bet," she said with a laugh. Just then I heard my phone ring from the deck chair. She looked at me with raised eyebrows and I shrugged.
"No idea who it could be," I said. "I'll get it later."
"I just got in for a few minutes to cool off," she said. "I'm going out with some of the girls, so I'll see you later." She got out of the water and my eyes trailed after her. I waited until she was inside and then exited the pool, the tent in my bathing suit clearly visible. I had abstained from relieving my sexual tension by myself. No matter how I tried, it paled in comparison to the real thing. But, given my lack of prospects on that front, I was contemplating breaking my hands-free dry spell.
I picked up my phone and looked at it, puzzled. The voicemail was from Christine, my mother's friend. Christine was younger than Jen and Laura, the "baby" of their friend group at twenty-five. Jen was young, having married my dad when she was in her mid-twenties, about Christine's age. I didn't keep track of my stepmom's friends that closely, but Christine was a regular. I thought she had called me by mistake, but then how did she even get my number? I played the voicemail as I dried off.
"Hey, Steven," she said, "It's Christine. I was wondering if you'd be willing to help me at the church this afternoon. I know it's late notice, but I've got a bunch of music to file away and Jen said you'd be able to help out some time. Anyway, call me back whether you can make it or not. Thanks!"
Christine had a singing voice, which was of little surprise to me. She was our church's music director, and was always singing or playing piano. She was a typical music nerd, always in a rush and always forgetting something. I smiled, glad for a diversion from my stepmom, and called her back.
"Christine, it's Steven. Do you still need a hand? Okay, great. Give me thirty minutes and I'll meet you there."
I got dressed and headed to the church. It was empty, being a weekday, with a solitary car in the parking lot. The office door was locked, so I entered through the side door and headed to the sanctuary. There, in front of the massive pipe organ was Christine, a pile of sheet music in her arms.
"Hey," she said brightly, "thanks for coming."
"It's no big deal," I said. "Jen's always volunteering me for free labor."
Christine blushed, "I'm sorry, if you don't want to help..."
"No, it's fine," I said. "I was just kidding around." She seemed jittery, more nervous than usual, but Christine was a nervous person anyway. "At least there's food at the end."
She laughed, putting her free hand on my arm and then quickly retracting it. She handed me a large stack of sheet music and led me behind the organ. There was a door into the mechanical workings of the organ, the real part that was hidden by gleaming pipes. There was a second room behind it, a storage room full of shelves, each labeled carefully by composer.
"Wow," I said. "They used to just shove everything in here."
"That's why we keep losing music," she said smartly. "I've been working for two months on this. Each piece has a number, that corresponds to a shelf. We need to sort these last few boxes, and then throw out all these worn out binders. After eighty years, you'd be surprised how much junk can accumulate."
We worked swiftly, making small talk about her favorite musical pieces, occasionally pausing for a drink of water. Christine seemed most at ease when she talked about music. She played piano, and flute, which I could have guessed. She was slender, with small breasts but curvy hips. Her blond hair was in a bun that leaked tendrils of hair down her neck. She was very pretty, in a completely opposite way from Jen. Christine's black-framed glasses gave her a nerdy charm, whereas Jen was all bombshell. After a while she discarded the light sweater she was wearing. The church offices were always cold, but the storage room and organ were warmer. I could see she didn't wear a bra, which was unnecessary with her smaller breasts. Her nipples were hard despite the warmth. I tried not to stare, but failed.
After about an hour Christine stood up, stretching. Her t-shirt was small and tight, and rose up quite a bit on her midriff. Even this small display captivated me. She leaned against the shelf, looking at me as I knelt on the ground, sorting scores.
"I really appreciate the help," she said. "Since I took this job, I've been doing this myself."
"You've done a lot," I said, surveying the room. She crouched down, putting spiral-bound music on a shelf. I looked over, and saw her pants were riding low, and I could see part of her ass. I had a thing for seeing a little of a woman's butt like that, I and I found myself responding in kind. All of this unwilling abstention had made my hyper-aroused at all times. I carefully adjusted my dick while her back was to me. As she kept working her pants slipped a little lower. She turned around and caught me looking. I blushed, and she turned around, kneeling opposite me. She hiked her pants up.
"I'm sorry," I said.
"It's my fault," she said. "These pants never stay on right."
"I shouldn't have looked," I said, feeling my face burn red. I had had sex with Laura several times, and gotten three blowjobs from my own stepmom, but getting caught checking out Christine made me feel like a middle school kid again.
"I don't usually get guys looking at me," she said and bit her lip. "I'm a bit of a wall flower." I realized that Christine was closer to my age than Jen's. She was shy by nature, a bit of a book worm.
"Are you kidding?" I said a little too quickly.
"Thanks," she said, brushing her hair back. "You're sweet."
She turned her back and started working again. After a few moments, she said over her shoulder, "how much did you see?"
"Not a lot," I admitted.
She said nothing but turned to face me. She had a new look in her eye I hadn't seen before. She took a deep breath and stood up. She reached forward and took my hand, pulling me up. I towered over her, and as we stood a foot apart I was struck by how pretty she was. And then in an instant she put her arms around my neck and pulled me close, kissing me. I was surprised, only less so than she.
We kept kissing, and she pulled me closer. My hands instinctively traveled down her back, and she melted into me as I cupped her ass gently. I picked her up, and we fell gently against the book shelves, her legs wrapped around me. She pushed me back a little and I set her down. I thought she had a change of heart, but then she took me by the hand and led me out of the stifling storage room and into the organ itself. There was a large space near the storage room and she pulled me close, kissing me once more. Then, without warning, she lifted off her shirt and pressed herself against me. My hands found her breasts, appreciating their size in my hand. She sighed as I gently pinched her nipples, kissing her while touching her. Then she unzipped her pants and let them fall to the ground. She wore nothing underneath, and I could see a strand of clear wetness spanning the space between her thighs.
Christine took two moving blankets and dropped them onto the floor. She laid down and spread her legs as I knelt between her thighs. She was so wet that she was already dripping onto the table. I buried myself in the short triangle of blonde hair between her legs. My tongue darted around her clit, tasting her. I wondered how long she had been thinking about this moment, given how wet she was.
I concentrated my efforts on her clit, and she started panting hard. My finger gently probed her pussy, eventually working its way into her. With difficulty I slid a second finger in, and she gasped as I gently fingered her while I licked her clit vigorously. She was tight, tighter than I had expected, and when she came her pussy clamped down hard on my fingers. She cried out gently as she came, her whole body shaking. She pushed me up gently, spreading her legs wider.
I slid off my jeans. Like Christine, I wore nothing under them. My swollen member sprang out, eager for release. She looked at it, her eyes wide, but she spread her legs even more and then arched her back. I rubbed the head of my dick up and down her wet labia, and then gently pushed into her. It took effort, and her breathing was ragged and I slowly entered her. She was tight, and gripped me as I worked into her inch by inch. When I was fully inside her she pulled me close and kissed me as I slowly thrust into her. It was slow going by necessity, she was so tight. I ground against her and she came quickly, her fingers digging into my back.
As her orgasm overtook her she gripped my dick so hard I had to wait for her to stop before I could continue. Just as I was about to start thrusting again we both heard the main church doors open and the voice of the staff event coordinator floating into the sanctuary.
"As you can see, we can accommodate a large wedding," she said to the trailing footsteps. The event coordinator was an older woman who had planned weddings for decades. We could hear the would-be bridal party talking amongst themselves, admiring the view. We were frozen, my dick buried deep in Christine's tight pussy.
"Don't stop," she begged. "Just do it quietly."
It was nerve-wracking, to say the least, to thrust into her quietly. I was conscious of every sound we made, and as the wedding group on the other side of the organ discussed logistics I found myself far from coming. I kept thrusting into her and she came over and over again, her body glistening as I ground against her. Finally she whispered "stop" and I froze. I was still inside her, and I could feel her heart beat as her pussy gripped my dick. The group was right by the organ, and the event coordinator was talking about recent renovations and restorations to the instrument. I knew from experience that she loved showing off the internal workings to guests.
Someone—perhaps the bride—asked about the reception hall, and the group slowly receded from the organ. I looked down at Christine, who bit her lip and nodded. I resumed thrusting into her, now with increase vigor. The very hidden—but public—act we were sharing, and the near-miss at getting caught, had been exhilarating. Her tightness only made my building orgasm stronger. I had not come in over two weeks, and when I did I exploded inside her. She gasped as I filled her, my dick pulsing against her pussy. She came with me, her body convulsing under mine. Finally, both spent, I pulled out of her and collapsed next to her.
We lay there for some time, until a thought dawned on me. Christine was shy, nerdy, and in love with music more than anything. There was something about the way she moved under me, the way she bit her lip as I entered her each time, that made me ask, "was that...your first?"
She nodded, grinning and kissing me. "I hope you aren't upset. Was it really bad?"
"No, it was wonderful," I said.
"How could you tell?" she asked.
I pulled her close. "You were really nervous."
She laughed quietly and sat up. An enormous amount of cum was leaking out of her. The moving blanket was a mess. She got up slowly, her legs shaking, and I followed. We picked up our clothes and stepped back into the music storage room. I looked at her slender frame, her b-cup breasts and firm butt, and felt some life stir back into my dick. She looked at it, too, and pushed me down to the ground gently. She took it in her hands, stroking it, occasionally bending down to lick the shaft, and then climbed onto me. With difficulty she sank down on me, impaling herself.
She inhaled sharply, and then started grinding against me. I gripped her hips and let her ride at her own pace. I was miles away from another orgasm, but Christine was soon coming. She rode me to one orgasm, and then another. I reached up and felt her small breasts, and she leaned forward and rode me deeper and harder. We kissed and I could feel the intense heat radiating from her body.
We stayed like for some time, until she collapsed against me and I thrust upward as she pressed her body to mine. She was so tight it seemed like an endless orgasm for her, until I got close and came a second time, pulsing inside her. Now completely spent, she got up off of me and helped me up. We got dressed, both giddy, and exited the organ room. As we left we ran into the event coordinator.
"Hello, Helen," Christine said. "We were just filing more music."
"I wish I had known," Helen beamed. "I would have brought that lovely bride-to-be back there to meet you. She has some ideas for music I wanted to share with you."
Christine waved a "sorry!" goodbye as she headed toward her office with her coworker. I waved back and headed to my car, light-headed. It wasn't until I started the engine that a thought hit me hard. How much of coincidence was it that another woman threw herself at me for some casual sex? My face burned as I headed home and the full realization of what had just happened hit me. As wonderful as it had been, I was mad.
Jen was upstairs in her bedroom when I got home. She was sitting on her bed, looking at a magazine. She could tell by the look on my face something was wrong.
"What's up?" she said, concerned.
"Next time you try and lend me out to one of your friends..." I said, starting a speech I had practiced in the car.
"What are you talking about?" she interrupted. "I told you, that happened one time."
"Today," I said, still hoping to use my speech, "just now. I went to the church to help Christine file music. And ended up getting it on behind the organ. And afterward I found out it was her first time!" I emphasized that last five words for effect.
Jen said nothing for a moment, and then said very carefully, "I did not tell her anything. Either she just went after you on your own or..."
"Laura," I finished for her.
"I'm sorry," Jen said. "I had no idea. They must have talked. I made Laura promise to keep her mouth shut, which was my mistake. I'm really sorry, Steven."
I sat on the bed, and she scooted next to me. "Was it at least good?" She tried to make light of it, to get me into good spirits. Despite behind mad, and looking for the right person to place that anger, I laughed. "Yeah, it was. But I thought she was really into me, and then on the way home I figured it out."
"It was really her first time?" Jen asked, looking concerned. "I had no idea, I just thought she was shy and nerdy."
"She's those things, too, but until an hour ago she was also a virgin."
"Behind the organ?" she said.
"Almost got caught, too," I said.
"Well, you certainly have done it in a weirder place than I ever have," she said, pausing. "Listen, I feel awful about what Laura did. I need to talk to her."
"Thank you," I said. "Even though it was nice, I still feel used."
"I know," she said sadly. Then, brightening, she said, "last time, I know what cheered you up. How about it?"
"How about what?" I said, not giving in.
"I have to say it, don't I," she said. "Fine. How about a blowjob to make it up to you?"
"I don't know," I said, getting up and pacing, enjoying the little game we were playing. I looked her over. She wore a spaghetti-strap tank top that showed a lot of cleavage; inspiration struck. "Your friends are trading my phone number, which isn't cool. If you're going to make it up to me, I want a topless blowjob."
She was surprised, and took a moment to respond. "Topless? Like while I'm doing it?"Yes," I said. "I think it's fair."
After a pause she said, "Okay. It's fair. When? Right now?"
I couldn't believe my luck. I knew Jen liked to bargain and bet using sex, but her quick agreement was unexpected. "How about on our trip?" I said. "A change of scenery, a BJ from my stepmom while she's topless. It sounds pretty great to me."
She laughed. "Okay, you pervert. Fine."
"But I'd like to see them right now, if that's okay with you."
"My tits? Right now?"
"Yes," I said, then hastily added, "please."
She sighed sarcastically. "Alright, you little perv. A preview, then." She took a deep breath and pulled her straps down. She tugged the tank top down until it was around her slender waist. She wore a black bra that perfectly framed her ample breasts. She was breathing hard, looking at me. She stood up, sliding the tank top down further. "Look only, okay?" I nodded, and she turned around. She reached behind her back and took off her bra, letting it fall onto the bed. She put her hands on her breasts and turned to face me again. I felt my breathing jump as she stood there, teasing. She turned to her side, still holding them, and then let go. Her breasts were large, but still pert and youthful. She turned to face me, and I stared open-mouthed at her tits. She laughed at the expression on my face, and her tits jiggled.
We said nothing for a minute, or an eternity, I couldn't tell. Time seemed to stop. I had seen other women naked before, but something about Jen topless was more erotic. I felt my dick swelling back to life.
"Okay, preview over," she said. She slid the bra back on and pulled up her tank top. Her tits looked magnificent in the tight shirt.
"Thank you," I said, my voice cracking a little.
"Let's grab some dinner," she said, checking her watch as if this was the most normal thing on earth.
Chapter 2
We ate dinner outdoors on the rooftop patio of a local favorite of ours. Her shirt was low cut, revealing a great deal of cleavage. Our water openly stared, which irritated me. Midway through dinner, the conversation turned to her showing her breasts.
"I'd say I can't believe I just did that, but this isn't the first time I've shown someone my tits like that."'
"I bet not," I said. "When did you first show someone, who was it?"
She thought for a minute. "Honestly, so many people have seen them, I'm not completely sure. I mean, my boyfriends had all seen them, of course. But just showing them off? It's a little embarrassing."
"Tell me," I said, urging her on. She looked around to make sure no one could hear.
"Probably my stepdad," she said, blushing.
"What?" I said. "Nick?"
"Yeah," she said. "I remember we were home alone, and in the kitchen. Maybe we were cooking together. I think that's what happened, because I remember getting something all over my shirt and I just pulled it off. I had a bra on, and he was staring, but trying not to stare, you know? And I saw he had a bulge in his pants, so I said whatever I had on my shirt and soaked through to my bra too, and took that off. I remember the look on his face. He told me to cover up, but I could tell he enjoyed himself. After that, it became kind of a game, for me anyway. I'd flash him whenever mom wasn't looking. He was mortified, but also secretly enjoyed it."
My mouth was open in surprise and she laughed.
"I can tell you, my tits have gotten me into a lot of trouble," she continued. "Nick was always cool about it. Mom's pretty top heavy, too, so it just came with the territory for him, I guess. But teachers, guys in school, anyone within ten feet of me just stares at them, or tries to get me naked." She looked at me mischievously, emphasizing that final word.
"I'm still floored that you flashed your stepdad. On multiple occasions."
She ate in silence for a minute or two before continuing. "By the way, I'm impressed. Sex in the church sanctuary, while people were touring it. That's a pretty risky move. Way crazier than any place I've ever done it."
"Hard to believe," I said. Jen was very adventurous when it came to sex. "What's the weirdest/riskiest place you've done it, then?" I asked.
She shifted in her seat, again making sure we couldn't be overheard. "Well, my stepbrother, that was pretty weird, right? But place? I'd have to say in the hospital. Your dad and I had been dating for a year. And he got in a car wreck, broke his arm. He was so pathetic, laying there all banged up. So, in between nurse visits, I sucked him off."
"Damn," I said.
"Yeah," she said, blushing. She paused as our waiter came by yet another time to check if we needed anything, and to check out her tits. When he left she continued. "I figured it would be too painful for him if I got on top of him, so I went down. I did it a few times that night, and almost got caught once. I had to pull away and throw the blanket over him as the nurse came in. He was hard a rock, and it was clearly visible under the sheet, but she said nothing. And when she left I finished the job.
"Also, once in college I worked the equipment issue at the campus pool. And this guy and I did it in the middle of work. I just bent over the counter and he pulled my suit to the side and went inside me. We had to stop and start a few times when people needed kick boards or flippers, but eventually he came all over my leg. I let it dry there and kept working the rest of the shift."
We finished, paid the bill, and drove home. We got home and put on a movie. Jen joined me in an oversized t-shirt. It was an old movie with a fair bit of nudity in it. It was one of Jen's favorites. She settled in next to me on the couch, her legs draped over mine as usual.
During one scene, in which case the young actress reveals her breasts, Jen said casually, "so how do I compare?"
"I'd have to see them again to give you an honest assessment," I said, joking.,
Jen, however, took it as a dare. She sat up and pulled off the t-shirt, revealing only a pair of black underwear. She looked at me expectantly.
"Honestly, yours are the nicest I've ever seen."
"Perv," she said, teasing, but remained topless. She swung her legs off of me and scooted close, leaning against me. She was practically naked, resting her body against me. "To be honest, I'm most comfortable like this."
"You have my permission to go around like this all day," I said.
She laughed, her tits jiggling. "I'd bet you'd like that," she smirked. On screen there was a sex scene, a pretty hot one, with the heroine riding her lover. "Sitting around, watching dirty movies with your topless stepmom."
"Well, I mean, why not?" I said.
"If I go around topless, then what are you going to do, walk around with a tent in your shorts all day?"
"I could go around naked, if that's what you mean," I said.
"Ha," she teased.
The movie continued and we put a second one on afterward. It was getting late and we were both tired. At some point we must have fallen asleep, because I woke in the middle of the night, both of us lying on the couch. Her back was pressed against me, and I realized with a start that my right hand was draped over her, my hand holding her breast. I also realized what had woken me up. There was a subtle movement. Jen was rubbing herself off.
She had done so when she had sucked my dick, and now, sleeping spooned together with her stepson's hand on her tit, she was rubbing her clit hard. I didn't move or let her know I was awake, but enjoyed the feeling of her in my hand. She ground her ass gently against me, and I was getting hard again. She must have thought it was an instinctual reaction in my sleep, because she did not stop. Her breathing was shallow and fast, her movements small to avoid detection. I could tell she was coming because she arched her back, her breath catching as she kept rubbing.
Jen came hard, her body tensing up as she kept a furious pace with her hand. She whimpered, the sexiest sound I had ever heard. I feigned sleep, enjoying this voyeuristic moment. Her motions slowed and her breathing returned to normal. Her hand slipped out of her underwear and she nestled closer to me. She put her hand on mine, readjusting it over her breast.
I couldn't take it any longer. With my hand gently squeezing her breast, I imperceptibly thrust against her soft ass. She was motionless as I slowly pressed against her repeatedly, my throbbing dick nestled against her ass. Eventually she started to press her ass against me to meet each of my thrusts, our bodies barely moving as I got closer to orgasm. Finally she pressed hard against me and I exploded. We froze, our bodies pressed together, as my dick pulsed hard and flooded my shorts with hot cum. She slowly relaxed as I kept coming, and finally we settled into each other comfortably. Slowly my cum soaked through my shorts, and through her underwear, and we fell asleep.
The next morning I woke up alone, with a note on the coffee table that Jen would see me that night. It was a miracle that Jen had unglued herself from me without me waking. I felt awkward, alone in the house after holding Jen all night. My shorts were stiff and stuck to me in weird places, and I got up and stretched with a jolt of pain. I heard my phone buzz and dashed over to check the text, hoping it was Jen. My spirits, fell, only a little, when I saw it was from Christine. She wanted to know if I was home, alone, because she wanted to come over and talk. I replied and went up to shower while I waited for her to come and see me
I showered the previous night's cum off of me and was drying off when I saw her car pull up. I hastily pulled on some jeans and a shirt and greeted her at the door with damp hair.
"Hey," she said brightly, grinning from ear to ear as she entered the house.
"Hi," I said. I was beyond feeling awkward after sex with a woman, Laura got me over that quickly. She had schooled me in the art of showing up, getting it on, and leaving. As Christine walked into the living room I followed her and sat on the couch opposite her.
"What's up?" I asked as casually as I could.
"Listen, we need to talk," she said.
When Jen came home, I was lying on a pool float, drifting aimlessly. I was a mess. An empty bottle of wine was floating in the pool near me, and my eyelids were half closed. She came out back, dressed in jeans and a flannel shirt, and saw the wreckage in the pool that was me.
"What happened?" she said.
"Christine," I said, not bothering to move. "She said she has a boyfriend, and needed a mercenary fuck to get it out of her system. She was a virgin, you know. So she needed someone for her first time, without any emotional baggage...for her. Must be convenient."
Jen said nothing. She surveyed the wine bottle, and then spoke. "How drunk are you?"
"Very," I said. I was too far gone to be angry, that had faded hours ago. I let my arm splash into the pool in a half-hearted effort to steer my slow rotation away from her. She walked around the pool, keeping me in her sight.
"You could have drowned," she said.
"I don't care," I said. "All that matters is this float, it's my whole world.
"You're not making any sense," she said.
"Well, I've been passed around your friends," I said, suddenly bitter. "So I'm just going to float here for a while, until I figure out what I'm going to do. Maybe I'll move out. I don't know."
Her expression changed. "Listen, I'm sorry." She said.
"That's nice," I said, aware of the hurt on her face as I said it. "But right now, I'm going to stay here and not care."
I regretted it as soon as I said it, but my logic was a bit blurry anyway from the alcohol. Jen turned from me, and I expected her to walk into the house to stew a bit. My words were intended to cut to the bone. Instead, she unzipped her jeans and slid them off. She wore blue and white striped underwear, and even in my addled state my dick perked up a little
"Well, I'm sorry anyway, even if you don't care. And if you're going to lay there all night in the pool, I'm going to come to you to apologize."
Jen threw her shoulders back, sticking her chest out. I could tell she wasn't wearing a bra under her flannel shirt. She suddenly flexed her arms backward, sticking her chest out more. As she did one, then two buttons of her shirt popped open. Then, in a violent burst, the rest of the buttons gave way and her shirt opened, revealing her tits.
My eyes popped open and I slipped off the float in surprise. She laughed, hard, and threw her shirt onto the deck. She dove into the pool as I got back onto the float, and swam toward me. She surfaced, propping herself up on the edge of the float. Her tits—even more glorious in the water—rested on the float between her elbows.
"I see I got your attention," she said with a smirk. "Are you going to float around all night, feeling sorry for yourself? Or are you going to accept my apology?"
I sat up a little and she crawled onto the float more. She reached the zipper of my jeans and pulled. The wet fabric fought her, but she eventually pulled my jeans down and freed my dick. I wriggled out of my jeans and she let them fall into the water. She reached forward and took my dick in her hand, casually looking at it, and up into my eyes, as I propped myself up on my elbows. Wordlessly she started to stroke me, gently, my dick growing in her hand.
"I was worried you'd be too drunk for this to work," she said, licking my entire shaft to help lubricate her hand. She slid closer, her tits touching the inside of my thighs. She stroked me, maintaining eye contact, and I wondered what could lead her to act this way. What made a woman give her stepson blowjobs? This was more than a dare, or paying me back, I realized. Her eyes shone with an intensity I'd never seen before.
"Come for me," she urged, pausing her strokes to lick my shaft every now and then. I sat up, and she slid closer, stroking me furiously. "Come on me, please," she implored.
I reached forward, sliding my hands under her tits. She obliged, lifting herself so I could cup them, before resting her weight back down. We were in the deep end, floating in a slow rotation, the motion of her handjob sending small waves through the water.
I was close, and I started to buck my hips. I wanted her to take me in her mouth, but she was enjoying herself. I came, grunting as a large burst of cum shot out over her shoulder. She aimed quickly as I kept coming, and stroked me as I spurt cum onto her neck and tits. I came hard, my dick shooting cum with each stroke of her hand, as if she was in control of my orgasm. Her tits were covered in cum, dripping down into the water that had pooled in the center of the float. When my orgasm ended she let go of my dick and swam to the edge of the water, looking over her shoulder at me. As she swam she slid off her underwear and kicked them off, letting them float away as she reached the edge of the pool. I swam over to her. She swam up to one of the water jets, pressing her pussy against it.
"I used to come like this all the time growing up. We had a pool and it used to give me the best orgasms," she explained. She rubbed gently against the wall, finding the sweet spot as water rushed over her clit. She moaned, pressing her body against the pool wall. I hung my arm onto the deck next to her. I pulled close, putting my free hand on her ass. She moaned as I cupped her ass and the water washed over her pussy. She was getting closer, and I was getting hard watching her come.
"Oh, jesus," she moaned, and started bucking her hips. She came, pressing her body against the pool wall and shuddering. I swung behing her, pressing my body against hers. My dick nestled in her soft ass, pointing straight up between her cheeks.
I thrust my dick upward against her ass cheeks, pinning her to the pool wall. She shuddered, coming again suddenly and violently. The constant stimulation on her clit was almost too much for her. She came a third time, shaking with the intensity of her orgasm as I thrust against her ass faster and faster. She came a fourth time, this time crying out in pleasure, begging me for a break. I pulled away, my dick throbbing. She led me to the shallow end of the pool and motioned for me to sit on the edge. I did, and she immediately pressed her tits around my dick and started to rub me off with them. I was so close, and her tits were so perfect, that I exploded quickly.
This second, smaller orgasm shot upward from between her tits, hitting under her. Pulse after pulse of cum flooded her cleavage as she pressed her tits against me, letting me come in the slick crevice. My orgasm ended, she stepped back, looking at the rivers of cum dripping down her stomach. She dove under, trailing blobs of semen as she retrieved our clothes. She tossed them onto a deck chair and exited the pool. She took my hand and handed me a towel. We dried each other off, and she led me into the house by the hand. I followed her up the stairs, mesmerized by the view of her ass as she led me to her bedroom. She pulled me into her bed, and we fell into spoon positions. I was pressed against her back, feeling her warmth against me as she turned off the light.
Chapter 3
We left the next day for the wedding. When I woke up Jen was already dressed, packing last minute items. She wore yoga pants and a loose top that showed her freckled shoulders. We packed quickly, making good time to the airport. The flight was uneventful, although Jen fell asleep against me and I was treated to a good view of her cleavage the entire flight. By the time we landed, my dick was dripping pre-cum.
Jen seemed aroused, too. Her face was flush, and she kept putting her arm around mine as we walked through the airport or into the hotel. The wedding was on her side of the family, one I was adopted into. Still, even for Jen it was the step-side of her family, and we found ourselves outsiders at the wedding. At the rehearsal dinner we found ourselves at a table with Jen's stepbrother, Jason, and his wife and kids. As we made small talk, I found it hard to concentrate on anything other than the fact that Jason's dick had been in Jen's mouth. Her own stepbrother. Of course, my dick had also been in her mouth. But talking to his wife and young kids underscored how bizarre it must have been for both of them. And, of course, he had fucked Jen's sister. I wondered if he had fucked Jen, too.
My moment to find out came later in the evening. The kids had wandered off to eat more food, and Jen and some of the other women were chatting across the room. I found myself sitting next to Jason, alone at the table. We made some small talk. I liked him, he was an easy-going kind of guy. He had had a few drinks, and I knew that this was the time to ask.
"Jason," I said, making sure no one was nearby to overhear us. "Can I ask you some questions, about Jen, when she was young?"
"Sure," he said, leaning in. "Any time I can embarrass my stepsister, I'm game." He grinned broadly.
"Well, I don't know how to bring this up to you, but she mentioned, one night to me, that she wrecked your car. And you were pretty mad. And she said she made it up to you, but she didn't say how. Did she pay for it?"
"Oh, that," he said, looking around the room. He paused, his fingers fidgeting. "No, I didn't make her pay for the damages. She just apologized."
"That's it? Just an 'I'm sorry.' I thought she must have done something to repay you. I know that when she was in college she'd bet sex on things. She told me about that stuff. So I wondered if, when she wrecked your car, she might have done something," I emphasized the last word.
Jason said nothing, but looked at Jen and his wife talking. Then he turned to me, he face red. "What are you getting at?"
"Nothing, nothing!" I said quietly, throwing up my hands. "I'm just curious, I'm trying to understand her."He took in my words carefully, and nodded slowly. "Understand her. Does she, um, has she had to...repay you for something?"
"You can put it that way," I said, grinning. I mouthed the word 'blowjob' slowly.
Jason exhaled. "I thought you were going to confront or judge me. Or worse, tell my wife. That was a long time ago," he mused. "So she's still at it, I see." His expression softened, and he grinned. "I can tell you, I was not expecting it. I was pissed, right, because she had wrecked my car. And she came to my room, and was all sweet and innocent about it. She apologized, and while I was ranting at her she just casually said she'd suck me off to make up for it. I thought she was kidding. And then she opened her shirt, and god, those tits."
He seemed lost for a moment, then continued. "So, yeah, I let my stepsister suck my dick. I came all over her, it was in her hair and everything. Our parents were downstairs, and she had left the door open. I was so afraid we'd get caught, it just heightened everything. There she was, on her knees with her tits out and my dick in her mouth. It was—and maybe still is—one of the craziest moments of my life. Anyway, I came and she got up and cleaned up and buttoned up her shirt and that was it. So, has she already, or did she say she was going to?"
"Since we're speaking confidentially," I said, "she already has."
"I wonder if she's as good as she was back then," he mused. "She's certainly had a lot of practice. So just a BJ?"
"Yeah," I said, omitting some of the details. "It was amazing."
"I bet," he said. "I didn't think it could get any better with her." He stopped short. I looked at him and he said, "never mind."
"Come on, you can't say that and stop there. What did you mean?"
He sighed, taking a drink. "Well, since you're not judging, I'll tell you this. We did it, once. And it was wild. It was at our family reunion, a year after the BJ. If you want to get her to talk about it..."
As he whispered his final comments the women returned. I looked Jen over, and I saw Jason do the same. His wife did not notice. Jen extended her hand and said to me, "are you too cool to dance with your stepmom?"
"I'm the least coolest person I know," I said, and took her hand. We walked out to the dance floor and slow danced with everyone else. Jen wore a silver dress that clung to her curves. It was modest, but I also knew she had a bra on and nothing else. When we had gotten to the hotel room we had ended up kissing, naked, her hand wrapped around my throbbing dick, when someone knocked on our hotel room door. We quickly got dressed and she opened the door to well-meaning relatives wanting to say hello. In the scramble, her underwear had ended up tangled in our sheets, and we had headed out to the rehearsal dinner.
We danced as one might expect from a stepson and stepmom. As we danced, she asked what Jason and I had talked about.
"Oh, not much," I said. "Just about you, when you were young and stuff."
"Embarrassing stories about me?" she asked.
"Sure," I said. "Not more embarrassing than anything you've told me. I mean, how many people here have you done something with?" I said this with a smile, and, in the dim dance floor lights, reached down and gave her ass a gentle squeeze before returning my hand.
"Oh, you know," she said casually, "I'd have to think about it." She looked around as we danced. "Just two, here, actually. God, that sounds awful."
"Who else?" I said, looking around.
"You are going to think I'm horrible," she said.
I leaned in close, "given how I've spent my last few weeks, I'm not going to judge. Seriously, who was it?"
"See that guy in the light grey suit?"
"The guy in his sixties?" I asked.
"Well, he wasn't in his sixties back then, but he was older than me by over twenty years. That's my stepdad's friend Mitch. He and I did it a lot one summer, when I was home from college. He hired me to help in his dental office, and I stayed late a lot, and, well, we fucked right on the dental chairs. He was married, which I feel bad about, really. But his wife wasn't interested, and he was interested in me, and we did it once because I felt bad for him. And after that we did it at least once a day, because he was so good at it. Once he fucked me from behind and my mom had an appointment the next day in the same chair. It was crazy. We must have done it like a hundred times."
"Jeez, how many times have you done it?" I asked.
"I couldn't count, to be honest. Let's just say I enjoy myself."
"And who's the other family member—or friend of the family—that isn't here that you've done it with."
The dance ended and the lights came up. She looked around and someone she knew asked her to dance. She smiled and left me to dance. I looked the retired dentist over. I decided against talking to him, and before I could do anything else Jason's wife, Danielle, asked me to dance. We made small talk, all the while I wondered if she knew that her husband had had sex with his stepsister when they were younger. When the dance ended Jen found me and took me by the arm.
"Let's get some fresh air," she said, and led me out of the room. The music faded as we walked through the hotel halls. We wandered, her draped on my arm, before she started talking. "Do you think I'm terrible?"
"No, of course not," I said. Then I asked a question I had wanted to ask, but was afraid to. "Did dad know about all of this?"
"No," she said. "I wasn't keeping it from him, you know. But it just never came up. He knew some things, here and there. Like the football game bet. God, that turned him on. He used to bet me all kinds of things to get me in bed. Even though he'd get me in bed whenever he wanted, it was fun to make it due to a lost bet. Or some kind of favor. I know it's been a long time, but I still miss him."
We walked the hotel grounds, a beautifully manicured garden, in silence for a while. I finally spoke, "about, well, about Dad. I guess he wouldn't be happy with either of us right now."
"When he passed away, he told me to be happy. And he asked me to take care of you. And right now, I'm happy taking care of you. He knew what I was like, I don't think he's mad. Are you feeling guilty?"
"A little," I said. "Just thinking about family a lot tonight."
"I know," she agreed. "Seeing everybody is bringing back a lot of memories. I'm glad I have you here. And don't worry about your dad. You know, he really wanted me to give someone a blowjob in front of him. He never asked explicitly, but I knew he wanted to. He knew that I once did two guys at once, and when I told him he was so turned on he fucked me three times in a row, a record."
"Two at once, huh?" I said.
She stopped, and sighed, "yes, once. It was Jason, believe it or not. And his cousin, Brian. We were visiting for a family reunion, about a year after I blew him. I'd never done anything with him again, although I knew he wanted to. The extended family had rented a campground and we had tents everywhere. Jason, and Brian, and I were hanging out in a tent, mid-day, it was so hot. And I don't know how we got on the subject, but we started talking about whether or not size mattered. Brian, as he liked to tell everyone, had a very big dick. He brought it up constantly to anyone who would listen.
"I remember Brian was bragging about how, by virtue of his size, he was bound to be better at sex. He was specifically trying to get at Jason, and I was defensive of my step brother. I told Brian that size didn't matter, and he said he didn't believe me. So, I told them that I'd judge right then and there. You should have seen their faces. I slipped off my shorts, buried my face in the sleeping bags, and told them each to go inside me and stroke a few times, without telling me who it was. And I'd tell them who felt better, who was better at it.
"So I did. And I remember waiting, with my ass in the air, for one of them to stick it in. I was getting pretty wet as one of them got behind me, his dick probing me. He slid in slowly, and I knew just by the size it was Brian. He was pretty awful, just thrusting away like he was sawing through a log. I let him enter me and thrust for about a minute before I told them to switch. He pulled out and after a little bit Jason slid into me. He was smaller, but immediately he angled differently, and each time he thrust into me I felt an electric tingle building inside me. I let him keep thrusting for a while, and finally said 'whoever this is, you're so much better. Don't stop.' And he started fucking me. I could feel an orgasm building inside me, and I came hard, biting my lip to keep quiet.
"I lifted my head up, and Brian was sitting next to me, looking dejected. His dick—and it was the biggest I'd ever seen—was still pretty hard, and I felt sorry for him. All those years of bragging, and I crushed his spirit. So I told him to let me suck his dick. He jumped at the chance, and Jason was thrusting into me while I sucked Brian. Jason came first, and I let him come all over my ass and back. Brian got close, and I stroked him to the final point, and he came on my face and neck. And I rolled over onto their sleeping bags, exhausted."
We were near the elevator when she stopped talking. I looked at her, and wordlessly I hit the up button. We said nothing as we entered the elevator and took it to our room, as a woman was already in the car. As we walked into the room I pulled her close and kissed her. She pressed her body against me as I unzipped her dress. She let it fall to the ground and took off her bra. She stood, naked, her pussy dripping in anticipation.
"You owe me," I said, "for what happened."
"I know," she nodded.
"But you're not paying me back right now," I said, taking off my clothes quickly. "This is about us, right now. And right now, I want you."
"I want you to," she said, pressing her body against me. I cupped her ass and ground against her as we kissed. I ran my hand through her short, wavy hair and she dipped her head back. I took it as an invitation to kiss her neck, running down and over her collarbone. I then reached down, grabbing her by the ass and lifting. She jumped up, wrapping her legs around me as she fell gently against the wall.
"Now," she said.
I didn't hesitate. I lifted her a little more, so that the head of my swollen, throbbing dick was rubbing against her slick labia. With barely any effort the head of my dick popped inside her, and I thrust deep into her. I was inside my stepmom.
We fucked hard, against the wall, our bodies plastered together. It was all I could do to stay upright, as I held her up and she wrapped around me. Jen came quickly, her pussy tightening around me as she panted hard. I kept thrusting, lost in the feeling of her body against mine, and she came again. This time I could not hold off, and I exploded with her. She cried out as I came inside her, filling her with all of the arousal of the moment, and the hours that led up to it. We stayed against the wall, her pussy and my dick pulsing in unison as I filled her with my semen. Then, as we came off our mutual climax, I set her down gently as I pulled out of her. Cum ran out of her and down her thigh, and she laughed.
I pulled her to the bed, and she lay down and spread her legs wide. She was a dripping mess, and I was still hard. I knelt between her legs and leaned forward to kiss her breasts, crushing her nipples gently between my lips. As I paid attention to her, she stroked my slick shaft, begging me to enter her again.
"How will you repay me if I fuck you again?" I asked between kissing her breasts.
"I'll fuck you every day, how about that?" she panted.
I grinned, and slid into her. She gasped, her eyes closing in delight as I started to fuck her again. It was more enjoyable now that I wasn't holding her up against the wall. My hands were free to roam and I felt her magnificent tits as I thrust into her. I was not even close to coming, and as I thrust into her, she came repeatedly. She moaned softly with each orgasm, her pussy gripping me tighter and tighter. Eventually I felt myself getting closer, and I came inside her again. She laughed in delight as I came inside her a second time, my orgasm just as intense as the first. She sat up and pushed me to lie flat on the bed. She crawled between my legs and started to lick my dick clean.
She took me into her mouth gently, mindful of how sensitive I was. She sucked me slowly, my flaccid dick trying to give up despite her efforts. She swung herself around so her pussy, dripping with my cum and her wetness, hovered over my face. I dove in, licking her labia and clit as she sucked me. I could feel myself getting hard again, but was enjoying the feeling of her pussy in my face. I licked recklessly, listening to her squeals when I hit the right spots. I teased her, avoiding her clit until she'd shift herself so my tongue would hit it. I was hard again, and now she was sucking me in earnest.
Jen came suddenly, her body shuddering. A flood of wetness and my cum leaked out of her and onto my face and chin. Was a mess, covered from her pussy's contractions. I kept licking until she leapt off of me.
"I need a break down there," she panted, laughing. I pulled her close, kissing her. I felt her tits as she stroked my dick, and I was inspired. I straddled her, and put my dick between her tits. She understood, and pressed her tits together around my dick as I started to thrust. I was lubricated from all the cum and wetness, and I slid between her tits effortlessly. She maintained eye contact while talking dirty to me.
"That's it, baby," she panted. "Fuck my tits. Come all over me."
I had come twice already, but eventually my orgasm started to materialize. I was getting closer, and she could tell by the angry, deep red color of my dick. She picked up the pace, rubbing her tits to match my thrusts. I came, a relatively weak spurt of cum shooting from between her tits and hitting her face. Smaller pulses of cum shot out, covering her tits. I kept thrusting, willing myself to stay hard.
When I stopped coming I got off of her and took her hand. She accepted, and let me pull her gently out of bed. She looked puzzled. We both looked worse for wear. Her hair was damp and hung in loose waves over her forehead. We were both wobbly on our feet, and she laughed and fell against me when she stood up.
"What now?" she asked. "I'm a little worn out, it's been a while since I've been with someone with so much energy."
"I had an idea," I said, and gestured to the balcony.
"You've got to be kidding," she said, looking over my shoulder. She was pressed against me, and I gripped her ass gently.
"No one will see who it is at this time of night," I said.
"But anyone who looks up from the grounds will see two people doing it on the balcony," she replied.
I took her hand and led her to the balcony. "I bet no one will see us," I said. I pushed her gently and she bent over the balcony, her ass sticking out to me and her tits hanging over the stucco. It was late, and the neighbor's balconies were empty and dark. We were six floors up, and anyone looking up would see us, but not recognize us.
As I thrust into her, beating my father's record, I looked down on the grounds. She thrust backward to meet my motion, our bodies slapping together. We fucked hard, our bodies exhausted. I never wanted it to end, that perfect night with Jen. I could no longer tell when she was coming, as her body shuddered over and over. She cried out, and a couple down below looked up. Jen's tits were swinging as she leaned over the balcony. It was obvious what we were up to as they pointed up to us.
I came, my body giving out as my dick pulsed inside her. I didn't even know if I had cum left to give her, but it didn't matter. I pulled out of her and we stumbled back to the bed and collapsed together. We were too exhausted to move. As we drifted off to sleep, she whispered in my ear.
"I won that bet."
"You cheated," I said.
"We never said we couldn't make any sound, so I won. And since I won, my prize is that you are going to move into my bedroom when we get back."
"What if I had one the bet?" I asked.
"You'll have to make a new bet to find out," she said, kissing me. And, finally, we fell asleep in each other's arms.