My Stepsister’s Summer Affair

Haley was a whirlwind after our first weekend together. My relationship with both girls had evolved dramatically for the better. She started hugging me more frequently when she and her mom would run into me around our complex, and she even told Cheryl that she was going to start calling me ‘Daddy’ because I was nicer to her than her own father, who she hadn’t seen in forever.

Cheryl seemed a bit uneasy about it at first, but ultimately didn’t object to it. Summer arrived two weeks later, and Haley would come over almost every day after I got home from work. I usually got home a couple of hours before Cheryl did, giving us time for a quickie. We practically had sex every day during that summer.

She would come over as soon as she saw me walking up to my door. My favorite was when she’d be lying out by the pool in her little bikini, showing off her tight, sexy little body. She’d come straight over to my place, and I’d remove her bikini to uncover her little titties and expose her smooth cunt.

Cheryl started going out with the girls from work, giving Haley and me more time together. The first time it happened, she called on a Friday evening, asking if I could check in on Haley, telling me she was going out with the girls for a quick drink after work. She hadn’t done this before, but I suppose she felt comfortable knowing she could count on me to look in on Haley.

That was the first time I made love to Haley on her own bed. It felt so special fucking my little girl on her own canopy bed. At times, Cheryl would go out with the girls on a Saturday night with Haley’s encouragement, telling her she was fine staying alone.

Besides, if she ever got scared, she knew she could come knock on my door. The pretense of her staying alone didn’t last long. Cheryl knew Haley loved hanging out at my place and said nothing when Haley would come over immediately after she left to meet the girls.

Often, Haley would be on her knees with her ass up in the air and my cock deep in her cunt when a text would come over letting me know Cheryl would be late, asking if I’d mind if Haley spent the night. “No problem, I’ll send her over in the morning” was always my answer, making sure not to add “with her pussy full of my cum.”

“No problem, I’ll send her over in the morning.” I’d say, making sure not to add “with her pussy full of my cum.” Fortunately, she never suspected a thing. She made several comments on how we’d developed a special bond during her Hawaii trip.

Over the next three years, our time together only got better, and Haley’s oral skills improved with her learning how to deep throat me. Haley had also convinced Cheryl to put her on the pill, claiming it would help with her irregular periods. During that time, she became the perfect girlfriend.

At times, she’d tell her mom she was going out for a walk and would stop by for a quick visit to suck my cock and get a mouth full of cum. Other times, she’d come over extremely horny, only wanting to get fucked in the ass.

I’d been playing with her ass for over two years before she told me she was ready to try the real thing. After starting her off with my finger, we’d gotten a small dildo slightly bigger than my finger. The first time I penetrated her tight little ass with it while fucking her, she actually passed out when her orgasm hit her.

The intensity of having both her holes filled was too much for her. That was her first DP experience. The first time I fucked her in the ass, I think I was more nervous than her. Cheryl had gone out with the girls, and we were expecting her to come home late, so we made arrangements to have Haley spend the night.

Haley and I had the whole night to enjoy each other, making love with no interruptions. By this time, she’d become an insatiable nympho. Whenever she came over, she’d be completely naked before the door had even shut behind her.

That night, we were watching a porno with a guy getting ready to take a young girl from behind as she begged for it. One of our favorite things to do was to reenact whatever we watched. While the porn played, Haley got on her knees with her ass up in the air and also started begging to be fucked in the ass.

“Please, daddy, I want you to fuck me in the ass,” she said, her voice trembling with desire. I went over to retrieve the lube and her favorite little dildo, but she stopped me and told me to only grab the lube, telling me that she wanted to feel the real thing.

Her words both excited me and concerned me. I loved her and really enjoyed fucking her hard when we got going, but I never wanted to hurt her. Little did I know at the time how much she was really going to love it and beg me for it in the future.

“I’m ready, daddy. I want you to fuck me in the ass,” she said, her voice firm and determined. I told myself I needed to take my time and make sure she was really ready before I started penetrating her.

By then, she’d experienced the joy of having me eat out her little ass more times than I could count. I enjoyed coming up behind her as she laid naked on my bed. She’d purposely wait for me on her tummy, knowing how much I loved her ass.

I’d grab a butt cheek in each hand and slowly spread them out as my tongue licked and kissed her inner thighs as it slowly slithered its way up and in between her cheeks. I loved the way she’d moan, letting me know she was enjoying herself.

That night, I approached it the same way. I grabbed a cheek in each hand and spread them as I started licking. The anticipation of what was about to happen had her excited, with her moaning louder than normal and telling me how much she loved daddy’s tongue in her ass.

She was also squirming more than usual. When I felt her arousal was at a peak, I lubed up my finger and slowly started penetrating her for a while before I added a second finger, making her grunt when she first felt it.

I reminded her to relax and just let it happen. The whole time this was happening, I was talking to her, reminding her how much daddy loved her and how much I was looking forward to finally being able to shove my cock in her ass.

Those words only made her more determined to make it happen. By the time I was up to three fingers, I knew she was ready. With my free hand, I somehow managed to squeeze some lube into my hand.

I grabbed my cock, which felt like a lead pipe, and made sure it was well lubricated, making sure it was ready to make an entrance. I removed my fingers and quickly got into position behind her.

I grabbed my cock and lined it up to her little brown starfish, anticipating how tight it was going to feel on my cock. Wasting no time, I grabbed her hips and held her in place as I pushed forward.

My cock head popped in easier than expected, with her grunting when she felt it go in. “Oh fuck, oh fuck… wait a minute, wait a minute,” she said, her voice trembling with surprise.

I offered to pull out, but she told me not to move. She said it felt bigger than what she was expecting, so she needed some time to get used to it.

After a while, I started pushing in again with no objection from her. She only kept repeating “oh my god, oh my god” and “fuck, fuck, fuck” until her ass made contact with my pelvis and my nuts were on her pussy.

After waiting for so long, I was finally in! I held my place for a moment, allowing her anus to get accustomed to my dick. Her ring felt great, squeezing tightly on my cock.

Slowly, I started pushing and pulling in small increments. She went from grunting in the beginning to moaning, telling me she always knew it would feel good when we finally did it.

Soon I had a steady rhythm going, allowing her first time to be as enjoyable for her as much as possible. She was spending the night, so there was no hurry.

When she came the first time, she begged me to speed up. It was excruciating feeling my nuts getting stimulated as they hit her pussy, but somehow I managed not to cum when she had her first orgasm.

She actually started crying, telling me that I was the best daddy in the world for showing her so much love. Staying in her ass, I stopped for a moment to allow her to enjoy her orgasm before I started up again.

So many times I was tempted to do exactly what I was doing, wanting to cum in her ass while I fucked her. Now that I was there, it was hard to hold back, especially with her talking dirty to me, telling me how much she loved it.

“Oh my god, daddy. Your dick feels so good… Do you like my tight little ass, daddy? How does it look daddy, how does your big fat cock look in my little ass?” she said, her voice trembling with desire.

“Keep talking like that, baby girl, and your gonna make me cum.” I said, my voice firm and determined.

“Do it, daddy, do it. I wanna feel your cum in my ass.” she said, her voice firm and demanding.

I was so close to cumming when she said those words, the words that my cock heard so clearly. There was no warning. Before I knew it, I was pumping squirt after squirt of cum deep into her bowels.

I felt like I couldn’t stop cumming, nor could she. The moment she felt my hot cum explode in her ass, she too started cumming as she shook uncontrollably.

It felt too good, with me not wanting to remove myself. Eventually, my cock softened, and she squeezed my dick out. After that, anal became a part of our lovemaking, with her always asking that I fuck her in the ass.

One evening, I was over at their place, hanging out with Cheryl on a Saturday night. Everything was unintentionally revealed. Haley was now a junior, and we’d been enjoying our secret affair for close to three years.

Cheryl and I were out on the patio, and we’d finished a bottle of Merlot, getting ready to open a second bottle when Haley got home from a party. She seemed to have had a few herself and was happy to see me when she got there.

She kissed her mom on the cheek and nonchalantly sat on my lap to hug and kiss me. She was obviously not thinking straight when, out of habit, she opened her mouth and her tongue came in searching for mine.

I too got lost in the moment and my hand grabbed her ass, as I parted my lips and gave her a proper kiss between lovers. “What the fuck, Haley?!” Cheryl exclaimed, immediately reminding us of where we were.

We quickly separated, but she didn’t get off my lap and kept her hand on my shoulder. “What the hell was that all about?” Cheryl asked, directing her question at Haley.

Haley quickly apologized to her mom, admitting that she’d indulged in a few drinks at the party and was feeling a little frisky, saying she may have gone a little overboard with me.

She hugged me again, hiding her face in the crook of my neck, not really sure on what to do, allowing me to wrap my arms around her for comfort and tell her it was not a big deal.

After all, we were all friends. We went back to our conversation for a while, although things felt a bit awkward. Several glasses later, the subject turned to kissing.

Cheryl was talking about the time Angelina Jolie had kissed her brother and how she thought it was so hot with them being siblings. She wondered if they were getting it on.

Then she surprised me. She added that even though it was unexpected, she thought it was so hot the way Haley had kissed me. She herself had always had a thing for older men as a girl and thought it looked so hot watching her little girl making out with an older man.

Haley immediately jumped on her comment and asked if she wanted to see it again. Cheryl hemmed and hawed, seriously considering Haley’s offer.

I was shocked when she said “Okay, but we better go inside before somebody sees us out here.” The wine had definitely enabled her voyeuristic side.

“Okay, but we better go inside before somebody sees us out here,” Cheryl said, her voice firm and determined. I was shocked when she said that, the wine having definitely enabled her voyeuristic side.

Haley was ecstatic, and I could tell she was already planning our next move. I couldn’t help but feel a sense of excitement and nervousness at the same time.

As we went inside, I couldn’t help but think about what was to come. I had no idea that this night was going to be a turning point in our little family’s dynamics.

Cheryl sat on the easy-chair to my right, her eyes fixed on Haley as she sat next to me on the couch. Haley’s question about Cheryl’s crush on her uncle Mark was met with a hesitant smile, but it was clear she was hiding something.

“Nobody in particular,” Cheryl said, trying to brush it off, but Haley’s eyes sparkled with amusement, and she knew her daughter wasn’t buying it.

“Come on, mom, tell us,” Haley coaxed, and Cheryl relented, her voice barely above a whisper. “I had a crush on Uncle Mark,” she admitted, her cheeks flushing with embarrassment.

Haley let out a squeal of delight, and I couldn’t help but chuckle at the sight of her mother’s blush. “I can see why,” Haley said with a grin, “he’s definitely sexy.”

“And so is your father,” Cheryl shot back, a sly smile spreading across her face.

“Oh yeah?” I asked, raising an eyebrow, and Cheryl’s smile grew wider. “Well, that explains the kiss,” she said, her eyes sparkling with mischief.

Haley leaned in, her lips brushing against mine, and I felt my heart skip a beat as our lips touched. The tension between us was palpable, and I knew we were on the cusp of something special.

As we kissed, Cheryl’s eyes never left ours, her gaze fixed on the scene unfolding before her. She looked…turned on, and I knew exactly what was driving her desire.

I reached out, my hands caressing Haley’s thighs, and she moaned into my mouth, her body melting into mine. I squeezed her ass, and she ground against me, the friction sending sparks flying through my body.

Cheryl’s eyes widened as she watched, her hand drifting down to her own body, and I felt a thrill run through me. She was getting off on this, and it was only going to get better.

Haley broke away from my kiss, her eyes sparkling with excitement. “Uncle Mark wants to fuck me, mommy,” she whispered, her voice husky with desire.

Cheryl’s eyes locked onto mine, and I knew we were both thinking the same thing: this was happening. This was really happening.

Haley threw off her skirt, and I could see the pink panties she wore, the sight sending a surge of adrenaline through me. I reached for her, my fingers tracing the curve of her hip, and she leaned into me, her lips brushing against mine.

“Mommy, help me,” Haley whispered, her eyes locked onto Cheryl’s, and I knew what she was asking for. I knew what Cheryl was thinking, too: she was giving her daughter to me, and she was going to watch.

Cheryl stood up, her eyes never leaving ours, and reached out to pull down Haley’s panties. I was already hard, my cock straining against my pants, and I knew it was only a matter of time before I was inside Haley’s warm, wet body.

Cheryl’s hands were trembling as she helped me remove my pants, her eyes fixed on mine, and I knew she was thinking the same thing: this was it. This was the moment we’d all been waiting for.

Haley’s eyes locked onto mine, and I felt a jolt of electricity run through me. She was ready, and I was ready, and Cheryl…Cheryl was watching, her eyes drinking in the scene unfolding before her.

As Haley lowered herself onto me, Cheryl’s hands grasped my cock, holding it in place as she aligned me with Haley’s wet slit. I felt a surge of excitement, and then…we were moving, Haley’s body rising and falling on mine, Cheryl’s hands guiding me deeper into her daughter’s body.

The sensation was incredible, Haley’s warm, wet body enveloping mine, and Cheryl’s hands holding me in place. I was lost in the moment, my senses heightened as I felt Haley’s body come alive under mine.

And then, just as suddenly, Cheryl was gone, replaced by a dildo, her body moving in time with mine as she watched us fuck. The sound of her own pleasure was like music, a symphony of desire that only added to the tension building inside me.

Haley’s body was a tight, wet glove around mine, and I was close, so close to coming. I warned her, my voice barely above a whisper, but she didn’t stop, her body pounding against mine in a frenzy of desire.

“Mommy, come ‘ere,” Haley whispered, her voice husky with desire, and Cheryl’s hands grasped my cock, her mouth wrapping around me as she swallowed my cum, her eyes locked onto mine as she drank me in.