My lover puts me in a challenging but interesting situation with her daughter
Before you go any further, please read the themes list, and understand this is a fantasy involving an older man and young girl. I understand this is disturbing to some, and would point out that there are dozens of themes available for you to select.
Over the next several months, Kelly and I made the most of our opportunities to be with each other. In addition to giving us the chance to just develop our relationship, it gave our spouses time to tend to the things on their agendas. Often, Kelly and I would take the kids and plan special events, allowing us to be with each other without taking every waking moment away from Jason and Allison. Other times, we would have only her kids or mine. We were as flexible as possible to ensure our spouses didn't feel we were abusing them with the gift they gave us.
Though we did spend plenty of time developing our sexual relationship, we also spent time just talking and sharing. We explored all of the desires on our original lists, created new lists, and discussed every aspect of the "Dirty Little Secrets" about which we had opened up to each other. I learned that Kelly was aroused by the thought of sexual encounters with younger partners. She shared more about her encounters with another woman. We talked about my past, when I had sex with two different 13-year old girls. Kelly seemed genuinely turned on by the thought of me inside such young girls, and several of our sexual trysts involved role playing with her as the young schoolgirl.
And we discussed the incest that was part of both of our younger days. We knew that those relationships had formed much of our adult sexuality, and we shared with each other about the sex we had with family members. Kelly, having slept with her dad, had a very different perspective than me. My experiences with my sister had been considerably different, as had the impact on my life. Though Kelly looked on her relationship with her dad favorably, she didn't really have any desire to renew it. The memories of my sister were a constant reminder of our love, and I would willingly take my her back into my arms and my bed.
Of course, those discussions were limited to times when we were alone, as we certainly weren't going to share such stories with the kids. Most of the time we had one or more kids, so our conversations were more mundane. In fact, when we were with the kids, our energy was focused on them. With the wide age difference between our children, our activities together varied depending on which kids we had at the time. When we had my kids, the activities tended to be more limited and more erratic.
Those nights we spent with just Kelly's girls, though, often turned into a sort of family game night. Both of her kids loved to play different games, and I was apparently more open to the game night theory than her husband. So, the kids took advantage of it. We almost always split into teams of one adult and one child. The girls would alternate so the teams would be more or less fair, over time.
Over the weeks and months of our relationship, we had several such nights, and the girls seemed to really enjoy the time together. They began to look forward to having me over and always gave up the chance to watch t.v. in order to play one game or another. I enjoyed the opportunity to get to know the girls better and grow closer to them. And since most of those nights ended with Kelly and I having sex in one form or another, I always looked forward to the night, regardless of what the girls decided to do.
Nearly a year into our very unique relationship, Kelly scheduled another "date night" for us on a night when my wife had a full schedule. Her husband took the opportunity to go out with friends for dinner and a late movie. Kelly arranged for a sitter for my kids, allowing us to spend time with her girls. The timing would also give Kelly and I a couple hours alone, after the girls went to bed. Confident we could find a way to fill the time, I spent the week looking forward to the evening.
That day, Kelly called me as I was heading home from work and asked if I could just head right to her house. She explained that she had already called Allison and let her know of the change, and that it would really help her out. I told her that was fine and that I would actually be at her house within a few minutes.
I pulled into the driveway wondering about the change in plans, and found Kelly standing in the doorway. She apologetically explained that her sister needed her help that night, and that she hoped I would be okay with watching the kids. Jason was heading right out with friends after work, and wouldn't be home until quite late. And unfortunately, Kelly's sister was dealing with things that apparently only Kelly could fix.
Though saddened by the loss of time with Kelly, I was more than willing to help out. She threw her arms around me and kissed me in thanks. Grabbing my ass, she said she'd make it up to me, before the end of the night if possible. We went inside, and Kelly gave me the rundown on the kids, dinner, and bedtimes. I'd spent enough time with the kids to know the rules, and figured it would be an easy night. Kelly told me she hoped to be back sometime between 10:30 and 11:00, when we'd be able to discuss my payment for the night.
As Kelly headed out the door, I called the girls and we discussed what we would do for the night. "Is it game night, or a movie after dinner?"
Cassie, the older of the two, pointed out that games with just the three of us would be difficult. Sarah agreed, and suggested we watch one of the new movies Kelly had picked up for them. I told them to decide on which movie to watch and proceeded to get dinner ready. Kelly had picked up some take and bake pizzas that were already in the oven, so it was about as easy as it could be. There were some sodas in the fridge, so I grabbed a few for the girls and set them up in the downstairs family room where we would watch the movie.
In addition to picking a movie and setting up the home theater system, the girls had dug up some t.v. trays, where I set the drinks. We ran upstairs, grabbed some pizza, and headed back down to watch the movie. The girls had settled on one of the High School Musical movies, but I was stuck. They weren't about to let me off the hook to head upstairs to watch something more age appropriate.
Sarah laid claim to the sole comfortable chair in the room, leaving Cassie and I to share the sectional sofa. Cassie sat next to me and took control of the remotes. "You're a man, but it's our system. We get to run it. No remotes for you!" She laughed at her joke, and I joined in. With two young kids at home, remotes are hard to keep under control, so I didn't feel out of place.
We ate while the movie played, and the girls had a great deal of fun teasing me about watching "HSM" as they put it. Sitting further away, Sarah's teasing was all verbal. Cassie, sitting right next to me, was much more physical. She would lean into me and look up, giggling. "Uncle Tom, who's your favorite character?" Or she would take my hand and try to get me to dance with her (I wouldn't). Then she would dance right in front of me, blocking my view of the t.v.
When I would point out that she was in the way, she would look back saying, "You don't want to watch the movie, anyway, do you?" And she would continue to dance in front of me. Several times, Sarah joined her sister, dancing in front of me, trying to simulate the moves of the actors on the screen. They would then flop back into their seats, laughing and giggling. They acted just like the young girls they were, and we all spent a great deal of time laughing at their antics.
Later in the movie, I mentioned it was time for a snack. Cassie looked and asked, "What do you have for us, Uncle Tom?" I rattled off the list of things Kelly had left, and they called out their choices, giving me a chance to get away from the movie. I ran upstairs, taking my time to get the snacks ready, then went back downstairs.
The girls were whispering together, and giggled when I walked into the room. "Are you two conspiring against me, planning your next big idea?"
"Of course," Cassie replied. Sarah chimed in, "Isn't that what all cute little girls do, Uncle Tom? Use their cuteness to get whatever they want?"
"And what do you two want," I asked.
"To stay up late," they responded in unison.
"Not tonight, girls. Your mother gave very specific instructions that you were to be in bed no later than 8 p.m. I'm not going to cross your mother, tonight."
They jumped up, hugged me, and said that was fine. They understood. Cassie, who stands just over five feet, despite being only 12, also reached up and gave me a peck on the cheek. "You have to obey mommy, too, don't you."
"Of course, she's in charge," I said as I handed them their snacks. The girls ate their snack as the movie finished. Once the show was over, I sent them to get ready for bed as I cleaned and straightened up. The girls were in pajamas and brushing their teeth when I finished, and I asked if they needed me to read them a story. They giggled, and reminded me they aren't babies.
"Of course not. So I assume you will get into bed and go to sleep on your own?"
They both hugged me goodnight, with Cassie again standing on her toes to give me a kiss on the cheek. Both went into their rooms and turned out their lights. After changing into some lounge pants, I sat down in the living room, and flipped on the t.v., turning the volume down. Finally able to watch what I wanted, I started flipping channels. After about half an hour of watching various shows, I heard footsteps in the hall which stopped, then continued toward the living room.
Looking up, I saw Cassie standing at the end of the hall, and asked if she needed anything. She came into the living room and said she had a note from her mom. She handed me an envelope and sat down on the couch. In addition to her being out of bed, I noted that she had changed out of her pajamas and into a t-shirt. In fact, it was one of my t-shirts, and it fit her more like a short skirt, reaching to just above her knees.
"I'm not sure how comfortable you should get, honey. You're supposed to be in bed." Cassie didn't move, and said I was supposed to read the note. I opened the envelope and took out the letter, which was obviously written by Kelly.
If you have this note, Cassie is no doubt sitting somewhere with you, as you wonder why she is out of bed. Rest assured she has my permission. She is up because I need your help and she needs your guidance. Several weeks ago, I caught her exploring her body. She was in her room using her fingers to pleasure herself. Over the next weeks, I monitored what she was doing, and found that it was not a one time thing. I asked her about it, and found that she has been developing an interest in boys. I'm not sure, however, just who she has been talking with, because she has suddenly become pretty knowledgeable about certain sexual things. Obviously, she has discovered how to stimulate both her boobs and vagina.
Given our discussions and your experience with young girls, I asked Cassie if she would like to learn more about her body with you. She said she might be, as long as I wouldn't get jealous. It seems Cassie is more aware of what we've been doing than we expected. I told her to approach you, after bedtime, once Sarah is asleep.
I hope you aren't upset, but my sister didn't really have an emergency. I am at her house, and will be home as planned. Cassie will let you know how much she wants to explore, and you can send her to bed at any time. She knows that she has to listen to you when you tell her that.
I sat there, looking at the letter, not sure how to react. On one hand, I wasn't sure how to respond. While the opportunity to mess around with a young girl with minimal risk was a dream, this was my lover's daughter. On the other hand, Cassie was apparently interested in exploring her sexuality, and she was sitting on the couch in nothing but one of my t-shirts.
Cassie could tell I was trying to think of what to say, so she acted first. "Uncle Tom, do you think I'm pretty?"
"Of course, honey. You're beautiful." I wasn't just being polite. Cassie has much of the beauty of her mother. She's very tall for her age, standing just over five feet tall. She is quite thin, weighing only about 80 pounds. She has her mother's bleach blond hair, complete with the loose curls. She wears it shorter than her mom, and it frames her round face in a bright frame. Though I had never really paid attention before, her long legs ran up to a rather shapely ass. Though she is essentially flat-chested, she has been wearing a training bra, helping give some shape to her developing breasts. All in all, she is a very pretty young girl.
Cassie jumped up and climbed into my lap as if she were a toddler, holding herself upright with her hands on my shoulders. As she sat there straddling my legs, she lifted her shirt up and asked what I thought of her boobs. Not quite sure how to respond, I said nothing. "Do you think they're as nice as my mom's," she asked, dropping her shirt back down.
That snapped me to some semblance of reality. "Cassie, you're way younger than your mom. And you've barely hit puberty. Give yourself time. You're perfect for your age."
Looking quite serious, Cassie told me how she liked to rub at her nipples. Then, she asked if I would like to touch them, too.
As if hypnotized, I nodded, then brought my hands up to her chest, taking one tiny, shirt covered tit into each hand. I gently rubbed the nipples, as that was nearly all that was there. Cassie, told me how good it felt, and asked me to keep doing it. As Cassie became excited by hands other than her own, she started to wriggle and squirm in my lap. The light silk of my pajama bottoms did little to isolate her crotch from mine, and my cock started to respond to the illicit actions we were taking. Unfortunately, my dick was caught in one pant leg, underneath her, and the fabric held it in place, pointing down my leg.
As Cassie continued to wiggle in my lap, her bare crotch rubbed across my now hardened rod. With only a layer of silk between her young pussy and my cock, if felt every bit of her developing womanhood. I was barely doing anything, yet Cassie was obviously getting aroused. The truth of her mother's letter became obvious as Cassie's hand moved down her body, toward her crotch. She started to rub at her slit, most likely fingering her clit. Watching her, I realized that she really was into masturbation. That made it time for me to make a decision. Send her to bed, where she would likely continue to play with herself, or allow her to stay on the couch, where I was likely to violate her.
It was the motion of her writhing on my leg (and cock) that shifted the balance, and I slowly lifted pushed her shirt up. Pulling Cassie's hand from it's spot between our bodies, I had her raise her arms as I slid the shirt over her head and dropped it on the floor. Pulling her toward me, I leaned my face into her chest and took one nipple into my mouth. As I sucked on her tiny little tit, her hand snaked back to her pussy. This time, it was obvious she was trying to get a finger to the lips of her cunt. She was again squirming in pleasure. I wondered if mine was the first mouth that had ever tasted her young breasts. It was obvious she had plenty of experience playing with her pussy, and that led me to question if she had tried anything else with anyone.
After several minutes of my playing with her pre-pubescent tits and nipples and her rubbing at the opening of her pussy, I picked her up off my lap and laid her back on the couch, against one of the pillows.
"You like to play with yourself. Would you like to see what it's like to have someone else do it?"
She nodded her head, with a quick and excited, "Yes."
Kneeling on the floor by the couch, I put my hand on her leg and slid it up toward the slightly puffy lips of her pussy. Cassie had obviously been fingering herself hard and fast. As my hand reached her slit, I marveled at her naked body. What I thought was a bald mound was actually covered in the downy precursor to pubic hair. Because her hair is so blonde, it blended in perfectly with her skin. Like her mom, Cassie is apparently a very true blond.
Moving my hand onto her puffy mound, I started by gently rubbing one finger up and down across her damp slit. Unlike her mother's distinct lips, Cassie had the tight slit common on younger girls. Watching her face for any sign she might want me to stop, I continued to slide my finger through the outer part of her pussy, easing it closer to the opening of her cunt with each pass. As the finger slid further in, I eventually shifted my position and started to direct pressure directly into her hole. Having watched Cassie just finger herself, I wasn't overly concerned with her ability to take a small finger, but I took my time easing it inside her body. She was obviously enjoying the feeling, and her breathing was starting to become noticeably louder.
As Cassie's young body became more and more aroused, I leaned my head toward her nubile titties, taking the little nipples into my mouth. Though I'm sure she will one day rival her mother, I reveled in the tiny tits she had at the moment. I continued to lick and suck at her flat chest while slipping my finger in and out of her now wet cunt. Cassie's breathing had picked up considerably, and I decided it was time to give her what I hoped was a new experience.
Slowly, with gentle care, I worked my mouth down her body, making my way toward the pussy I was currently fingering. Licking from her chest, down her ribs, I slid my tongue across her taut preteen belly, lingering at her belly button. Cassie gasped with sexual tension as my tongue moved past her waist and across her pubic mound. Licking lightly at her downy hair, I moved the final inches toward her young pussy.
I lifted her knees up, drawing her feet toward her body. Gently, I pushed her knees apart, giving me a wonderful view of her developing vagina, and better access for what I intended on doing. Positioning myself as if we were going to 69, I lowered my mouth to the slit between her legs, and licked softly at her pussy. Cassie again responded with a sharp intake of breath, and let out a soft moan. Confident that meant she wanted more, I continued to lick up and down her slit, easily spreading her open with my tongue. With each thrust of my tongue, I shoved further into her pussy, until I was licking at the opening of her cunt.
Pushing hard, I forced my tongue past the opening, literally fucking her with it. I started to ease my tongue in and out of her pussy several times, then shifted my mouth up so I could lick at her tiny clit. She had yet to develop the larger button her mom has, but it was still sensitive to my touch. I licked around it, then directly over it, savoring the taste of her prepubescent juices. Something about the taste of young pussy drives me wild, and I began alternating my attention between the button of her clit and the opening to her cunt.
Cassie was starting to vocalize her pleasure, and I felt her hands move to her tiny titties. Looking up at her, I realized she was, in fact, rubbing her own little nipples while I ate her out. As she got more into her own play, I moved my mouth back to her tiny clit and moved a hand back to the opening of her pussy. While gently caressing her clitoris with my tongue, I eased a finger back into her cunt, slowly fucking her with it.
Cassie started to shake with pleasure, and had to push me away from her body and she clamped her legs together. She was breathing heavily, moaning from the excitement. It was pretty obvious she had reached the boiling point, if not outright experiencing an orgasm.
Lifting her feet up, I sat down on the couch with her legs over mine. Staring at her young, naked body, I asked if that was better than playing with herself.
She was still dealing with the feelings running through her body, and she just nodded. Then, she added, "Way better."
We sat there on the couch, me admiring her developing body, her recovering from the flood of intense emotions and feelings. After several minutes, she pulled her legs off mine, and sat up onto her knees. She then moved across the couch, and straddled me just as she had when first joined me on the couch. "Really, Tom. That was better than anything I've felt before. And I've tried quite a lot on my own."
The combination of what had just happened, having Cassie jump back on my lap, and just having a naked 12-year old in my arms brought my dick to a new level of hard. Cassie's position put her right on top of it, with nothing between us except the fabric of my pajama bottoms, and my precum had created a pretty significant wetspot on those. Cassie's was pretty wet, herself, and her juices mixed with mine to create a pretty wet mess of my pants.
Cassie started to wiggle her crotch against mine, obviously aroused by the feeling of yet another body part rubbing across her already sensitive slit. The effect on me was quick and profound. I told her to stop for a moment, and I raised my body up, sliding the pajamas down far enough to free my hungry cock.
Sitting back down, I pulled Cassie back toward me. "There, you can keep doing what you were doing, now."
Cassie needed little encouragement as she felt the length of my shaft pulsing in attempts to get at her tight little hole. Cassie started to rock her hips, sliding her wet slit across my cock, driving me wild. She continued that for a short time, until I couldn't take any more.
Reaching down, I positioned myself so that the next time she rocked her hips back, she slid onto instead of across my cock. I held her waist in order to slow her down. At 12, I didn't want her sliding onto my cock in one motion, so I helped her ease herself back. Slowly, the head of my cock pushed toward her cunt. She continued to rock back, and I was amazed when my cock slid inside her with relative ease. She moaned loudly, and her eyes started to close in unbridled lust. We both started to breathe in short, quick gasps as my cock started to slide further into her tight pussy.
Surprisingly, though, I never felt the resistance I expected to encounter from her hymen. And when she forced herself all the way down on my shaft, there was none of the pain that comes from breaking that cherry.
With a 12-year old girl starting to slowly bounce on my cock, I had little time to consider that at that exact moment. Instead, I relished the feeling of my rod sliding in and out Cassie's body. She leaned into my body and I hugged her tightly to me as she continued to slide up and down on my cock. Her tiny hole sucked and grabbed at my cock, and I loved the feeling.
As she loosened slightly to accomodate my size, Cassie started to fuck me harder and faster. She was lost in the feelings, and continued to squeeze me tightly with her arms. With my arms around her back, I pulled her tightly into my body, and lost control.
As she dropped onto my cock one last time, I experienced a crazy orgasm and my cum flooded into her pussy. She went wild as that happened, and I was sure she had never experienced a man cumming inside her, before. As she continued to rock on my now sensitive cock, she made sure every last bit of sperm was pulled from me. All too soon, I had to lift her off me. When my dick popped out of her, I saw bits of cum ooze down her leg and grabbed the t-shirt to wipe it up.
Cassie laid back on the couch as I cleaned up the cum that her cunt couldn't hold in. Realizing I was cleaning her with the t-shirt she had been wearing, I apologized and said we'd have to find another shirt.
"That's okay, I think I'll go to bed like this. Besides, I'm not sure if there are any of your t-shirts left. We took the last two."
I wasn't sure if she meant to say that, but I definitely caught it. "What do you mean 'we' took the last two. Who's 'we?'"
Cassie didn't say anything, at first. Instead, she stood up and jumped back into my arms. "Thank you, Uncle Tom."
Pushing her back a bit, I told her I had two questions. "First, what experiences have you had and with who? Because I'm betting you've had sex, before."
Cassie looked at me and said she hadn't. "But, this isn't the first time I've had something inside me. I found one of mom's things and used it."
"Things? You mean a sex toy? Something that you use to play with yourself?"
"Yeah, I accidentally saw mom with it, once, and took it to try, myself. But I've never done this, before."
"Okay," I said. "That makes sense. Well, it's believable. I'm not sure any of this makes sense. Second question. Who's 'we?'"
"You already asked that. All I can say is that you'll find out, soon enough. But now, I have to get to bed."
With that, she gave me one more hug and kiss on the cheek, then ran off toward her room, still naked. I watched her nude form heading down the hall, savoring the view. Then, pulling my pajama bottoms back up, I tried to get back to whatever was on t.v.