It was at a local restaurant that I visited a lot and seeing her, I was immediately attracted to her. I knew she was young, probably too young for me being i was in my late 40s, but I eventually decided to see if I might be able to get her to go out for drinks and maybe even go to my house. Well, it worked nd being alone with her was amazing.
Peyton
Well to start, there’s this small family owned Italian restaurant by my house that’s probably my favorite, especially Friday evenings after work, when I need a drink, and something to eat. The staff there is always very friendly, and being I’ve been going there for a very long time, many know me when I walk in, or at least it feels that way. Anyways, the owner likes to hire high school and college kids, trying to give them their first opportunities to work, which I support.
With that said, this one particular Friday, I immediately noticed there was a new hostess they had hired. She was a very attractive young girl, and her friendly smile and, bubbly demeanor almost immediately had me drawn to her. She really was pretty, had a friendly personality, and a smile that made me stupidly smile too.
She had dark straight, shoulder length hair, and being she was petite, small framed, she didn’t have big boobs, which I liked. It really was hard to not check her out every time I’d follow her to my table, and think about being with her, especially seeing that great looking little butt. Furthermore, seeing that pretty face smiling back at you, it really was hard to not get caught staring at her firm little body and tits, especially whenever she happened to wear one of her tight black top.
Most of the times, when I followed her as she took me to one of the booths, continuing to smile, I couldn’t help but look down at the fancy design on the back pockets of her jeans. “Man,” I thought, “she’s got a great little body,” and seeing her shapely little ass and somewhat long legs in those jeans as she walked away, only accentuated the fact.
Sitting down, I couldn’t help but watch as she walked away, and again think about being with her. However, being I had to be more than twice her age, I knew there was no way, but it was still hard to not fantasize about getting her in bed. Every time now, when I visited this restaurant, which was starting to be more and more often, I always found myself looking for her, always hoping to strike up a conversation, hoping there might be that opening to ask her out.
However, being she was obviously a student, she wasn’t there much during the week and when I realized she was usually there only on weekends I tried to go not only Fridays like usual, but Saturdays too. She really was so attractive, naively friendly and whenever we happened to talk, I always ended up clumsily flirting with her. I wanted it to happen but it was easy to see it made her a little uncomfortable, especially when there were other customers or staff nearby. Yea, I know it was awkward, and I didn’t want her to feel uneasy, but I really liked her and continued to hope maybe there would be a chance.
She was all I could think about and after a couple weeks, I got up the nerve to ask her, “What’s your name?”
I already knew the answer, because I asked my waitress one time, and when she smiled and simply replied, “Peyton,” there was an awkward pause.
Smiling too, I introduced myself, and as we shook hands, I stumbled over my words, trying to hold a conversation. It was a little embarrassing and as she eventually left, I couldn’t believe how tongue tied she had made me, which left me again to think, “There’s no way.”
However, the more time I spent there, the more obsessed I was becoming, and when she happened to wear a pair of these tight yoga pants, that more than accentuated her tight little butt, I thought, “My god, I want to be with her.”
I wanted to see her as much as possible, and it had to be obvious I was looking to make something happen. We were becoming more personable, and the more we saw each other, the more it felt like we were becoming more friendly, leaving me to think, she might be attracted too.
Maybe I was giving her a lot of attention, but it was for good reason and maybe it was just me, but every time after taking me to a table, and saying my waitress would be over soon, she’d always give me a parting smile, always leaving me gawking as she walked away.
She had to know I was interested, at least I hoped she did and whenever she’d happen to casually stop by to check in and talk to me it made me think, “Maybe, just maybe, she is interested too,” but then again, I felt it was just her needing to be a good hostess.
I tried to ignore my feelings for her, being she was so much younger, but it was hard, and when I found out from one of the servers that she was actually in college, I again thought maybe, which again had me searching for a way to graciously ask her out.
Yea, I was fantasizing about being with her, and coming to realize there was no way, I left it alone. However, she was always on my mind, and feeling I needed to push it, I went way out of my comfort zone this one time when she happened to stop by my table to talk, and seeing an opening I bravely asked, “Do you maybe wanta go get a drink when you get off work?”
I knew it surprised her, I’m sure of that and after a long pause I said, “Yea, I’m sorry, you probably have a boyfriend.”
It made her smile and blushing she said, “No, I don’t have a boyfriend,” and looking at each other, I smiled, and as I thought of a way to respond, I shifted in my seat, but before I could say anything she said, “Sure I guess.”
It surprised me and as I searched for where we could possibly meet she said, “I’ll be right back.”
I worried that she was blowing me off but she eventually did come back, and seeing her apprehension I waited for her, hoping she’d indicate that she meant it. Wanting to see if there really was a possibility, I smiled and taking the opportunity, I suggested, “ How about somewhere down in olde town?”
She was hesitant how to answer, and I think she was hoping I really didn’t mean it, but then smiling she said, “Sure.”
I couldn’t believe it, but after talking about when and where, and exchanging phone numbers, she again left, heading back to the hostess station.
From a distance, I could see her looking my way, occasionally smiling, and not wanting to appear overly excited, which I was, I tried to not show it. I was so excited to maybe be alone with her and after finishing my drink and plate of spaghetti, I paid my bill and got up to leave. We ended up smiling at each other as I left and when I casually but nervously said, “See you later,” she smiled.
It was an awkward one, and then after quickly looking around, she again turned and smiled as a couple of the other hostesses said, “Bye.”
Maybe it embarrassed her a little, and I really hoped she meant it, but as I sat at home waiting impatiently, and feeling she was just being polite I thought, “It’s not going to happen.”
I wanted to text her, but I didn’t want to look overly anxious, and knowing when closing time was, I waited, continuing to think about being with her. Hoping she’d contact me, I checked my phone often, but after a while, I again felt, “She’s blowing me off.”
Yea, it was for good reason, being I was so much older. I worried it wasn’t going to happen, but then suddenly there it was, a text message. Quickly grabbing my phone and looking, it was her. It made me smile and as I opened it and I saw her message telling me she was off, I immediately responded, “Great!”
I was excited, but nervous, and as I searched for where we could meet, she texted me, suggesting we meet at a little pub down in olde town. I sensed she was nervous too, and maybe a little anxious about meeting, I know I was, however I wanted the chance to be with her.
I knew where the bar was and after a few messages about timing, I got cleaned up a little. I didn’t want to appear too anxious, so I didn’t change my clothes, but I did spray on some cologne and then thinking, hoping, I decide to grab a condom out of my drawer. Smiling, I tucked it in my pocket, and then decided that I should probably bring a Cialis too, just in case. Yea, I know it’s weird, but I had the pre***********ion for those times when, you know, you didn’t want to fail, and this was just one of those times.
Quickly pushing it into my pocket too, I headed off to meet her. I so wanted this to go well and after parking a little ways away, I made my way up to where we were going to meet. It was already kind of dark and when I saw her waiting out front, I confidently smiled, as I continued to walk toward her.
Eventually, Peyton turned and seeing me coming up the sidewalk, she smiled too. It looked to be an excited one but a little nervous too, and after saying, “Hi,” we shook hands and headed inside.
I couldn’t help but think, “This is so nice to finally be with her,” but in the back of my mind I continually thought, “There’s no way,” but convinced myself, “just enjoy it.”
We ended up talking, having a couple of drinks, and jokingly we got to know each other. In conversation I found out she had graduated from a nearby high school and that she had been a cheerleader there. It wasn’t hard to imagine, being she was so attractive and friendly. We were definitely having a good time, but seeing we might be drinking a little too much, too soon, I suggested we order some appetizers.
It really was a good idea, I so wanted this to go well, I didn’t want either of us getting too drunk, and after awhile, when there happened to be a lull in our conversation I brazenly asked, “Do you wanta come over to my place?”
It obviously surprised her, because she seemed to be leery, questioning it. I definitely didn’t want that, and seeing her reaction, I stupidly tried to take it back by saying, “It’s okay, I understand if you don’t want to.”
I could, however see her thinking about it, trying to determine what my intentions might be, but then she smiled and nervously suggested, “How ‘bout we go to my apartment instead.”
I didn’t know if she really meant it, or if she was really looking for a way to end our, let’s say date and escape. In either case, I said, “Okay,” and trying to not act overly excited to be alone with her, I simply smiled.
She still seemed unsure at first, but smiling she too said, “Okay.”
I think in a way she felt obligated, but it still made me smile to think about being with her. I really was excited to go over to her apartment, and as we finished our drinks and the last of our appetizer, I got our waitress’s attention.
Quickly paying the bill, I looked over at Peyton and when I asked, “Are you ready,” Peyton smiled hesitantly, and nodding, we left the bar. I still had a feeling she was maybe a little apprehensive about being with me, but trying to shrug it off, I asked,” Where do you live?”
Smiling she said, “Why don’t you follow me.”
Smiling too I jokingly replied, “Don’t lose me.”
I’m sure she was thinking about it, but being she lived kind of close, it didn’t take us long before we pulled into her complex. Parking, I hurriedly got out of my car and seeing her smiling, I smiled too and followed her toward her building.
Like I said, it was already dark, and as we went inside, she flipped on a light. I was nervous, and as I looked around, all I could think was how I wanted this to go well. I knew I had to tread lightly being there was such an age difference, but trying to be as casual as possible I said, “Nice place.”
It made her smile and as we stood there for a moment, she asked, “Do you want anything to drink?”
“Definitely, “ I thought, wanting to keep the buzz going, really needing it to keep going, I naively smiled and asked, “Whatcha got?”
Smiling and following her into to the kitchen area she said, “Well, I’ve got a couple beers or I can make us a couple drinks,” and continued by saying, “I can make us rum and cokes!”
It wasn’t my favorite but I knew it was easy and seeing that she liked them, I smiled and excitedly agreed saying, “Sounds good!”
Eventually, we headed back over to the living room and as I sat on the couch, we made a toast and then took a drink. It really wasn’t that bad and looking at it I remarked, “Mmmm, that’s pretty good.”
It made her smile and after taking a drink herself, she nodded, giving me another big smile. Sitting there talking, I think she was still nervous, and needing a little distraction she asked, “Wanta watch some TV?”
I really didn’t care, I just wanted the chance to be with her, hoping to maybe get her in bed, and as she got up and grabbed the remote, I couldn’t help but look at her little ass as she bent over. Smiling, I boldly scooted over closer to where she had been sitting and as she sat back down, she brushed against my thigh.
Looking over at me, she smiled and then immediately shifted over a little. It made me smile too, but I worried that I might have over stepped, however as she took a big gulp off her rum and Coke, she put her hand on my thigh and said, “I’ll be right back.”
She had stood up and as I smiled nervously, she looked at me and casually said, “I gotta pee.”
Relieved for a moment, continuing to smile, she headed into the bathroom that was just off the kitchen, but as I sat there I thought, “Oh yea, that’s it, it’s probably over now.”
However, she wasn’t in there very long and as she sat next to me she smiled and said, “That’s better, and as she grabbed her drink off the table, Peyton had casually put her hand on my leg again, bracing herself in a way.
I could smell that she had sprayed a little perfume on, and as she took a big drink, I smiled and looked down at her hand briefly, thinking, “Maybe she’s trying to signal to me that she’s interested, wanting me to make a move.”
Looking over at her and seeing her smiling, I couldn’t help but smiled too. I wanted to kiss her, and hoping it’s what she wanted, I got up the courage. However, as soon as I leaned toward her and put my arm around her back, she asked, “What are you doing?”
It surprised me, I didn’t know if she actually meant it but then seeing her smile, I leaned into her, and giving her a hug, I pulled her close and innocently kissed her on the head. It made her look up at me, and when I again went in for a kiss, Peyton closed her eyes.
Closing my eyes too as my lips pressed against hers, I excitedly pulled her closer, trying to press against her. It was only a simple little kiss and after another hug, we both nervously reached for our drinks, and took a big sip.
Sitting back, there was an awkward pause and as we looked at each other, Peyton suddenly blurted out, “How old are you?”
I didn’t know how to answer but smiling I asked, “How old are you?”
It made her smile, but seeing she wanted to know I replied, “How old do you think I am?”
Looking at me questioningly she said, “You’re 30, right?”
Again it made me smile and after a second I lied saying, “That’s close,” and when she asked, “Are you 32,” I said,” “Yea,” and continued by asking, “Am I too old?”
It made Peyton blush, and then smiling she quickly replied, “No, you’re not too old.”
I knew she was probably around 21 or 22, but want to keep the conversation going I again asked, “How old are you?”
Looking at me unsure, she cautiously asked, “How old do you think I am?”
Smiling, looking her up and down briefly I said, “Are you 25?”
It made her smile and after saying, “No, I’m only 21, she asked, “Am I too young?”
“Oh my god,” I thought, “no you’re not,” but wanting to play along I remarked, “I thought so, but you carry yourself much older.”
It again, made her smile, and again I was relieved she was okay with me being older, but maybe it was the alcohol too, but I do think right now we were both thinking the same thing.
Yea, she was much younger than me so I didn’t press it, but wanting to break the tension, wanting to keep it going, I took her hand, and as Peyton looked over at me, I smiled and said, “This is nice.”
She didn’t say anything, but smiled, and then leaning against me again, I casually put my arm around her. It was kind of an awkward moment as we sat there holding each other, and as we continued to watch TV, I thought to myself, “How can I keep this going?”
Searching for how, and needing a way to give me time to think, I immediately asked to use her bathroom, and it worked! Peyton smiled and enthusiastically said, “Sure, you don’t have to ask.”
Smiling and patting her on the thigh, I quickly stood up and headed into the bathroom. Closing the door, I took a deep breath and as I stood there peeing, I remembered the pill in my pocket. Smiling to myself, I washed my hands, and after getting it out of my pocket, I popped it in my mouth and taking a handful of water, I swallowed it. “Oh my god,” I wanted it to happen and after drying my hands, I again took a deep breath and went back out.
Moving over toward her, I jokingly asked, “Did I miss anything?”
It too made her smile and as I sat next to her, I grabbed my drink and took a sip. Smiling, I remarked, “Thanks for letting me come over,” which made Peyton smiled too.
Putting my arm around her again, I pulled her closer, and when we again looked at each other, I put my drink down and then taking hers, doing the same, I again leaned toward her. Smelling her perfume, and seeing Peyton smile as she looked at me, I immediately went in for another kiss.
It really was nice to be with her, and I think she was feeling more at ease, because as we again hugged, she snuggled up against me. I really wanted it to keep going, and when I again kissed her on the head, she again looked up at me. Smiling at each other, she leaned up and closing her eyes, we kissed.
Pulling her close, I immediately tried to push my tongue into her mouth, which I think surprised her, because she pulled back a little, but eventually she opened her mouth too. Smiling to myself as our tongues met, I casually moved my hand up, trying to feel on her boobs.
“Oh yea,” I thought, it felt good to finally be feeling her and even though it was through her top and her bra, feeling her firm little tits was amazing.
Looking at each other, smiling, we again hugged and when I tried to subtly move my hand up under her top, she didn’t stop me, which made me smile to myself. Kissing her again, wanting to actually feel her boobs, I casually cupped one of them and then slipped my fingers up under her bra.
Realizing what was happening, she drew in a big breath, and holding it in, she quickly reached up to block me. We had stopped kissing and she looked a little nervous but smiled, and after a few seconds, she leaned over to kiss me.
Being with her had already given me a hard on, but now being able to feel the soft cool skin of her boob, and her little nipple, made my cock kind of uncomfortably bound up in my pants. Reaching down, I casually adjusted it and when I saw her glance down too, she must have known, because she smiled.
Taking my hand out from under her top, and looking at each other, we smiled, and again we tried to give each other a kiss. It really was amazing, and feeling her smiling as we kissed, I couldn’t help but smile too.
Putting my hands on her sides now, holding her, I deliberately let my thumbs press against the bottom part of her boobs. I so wanted to keep going and when Peyton feistily slid her hand down to my crotch, I thought, “Oh my god, yes!”
Kissing her, I wanted her to feel how hard I was, and when I turned slightly and she happened to feel it, we stopped kissing. Looking at each other, I smiled and when she took hold of it, and gave it a squeeze, I could see her smiling as she continued to look down.
Eventually, she looked up at me but it was a cautious look, and then reaching down, I took hold of her hand and had her start rubbing my cock through my jeans. After a kiss, we smiled at each other, and as I laid her back a little, I went back to feeling on her tits, and we again kissed. Again, I immediately put my hand up under her top feeling on her bra. Her nipples were definitely hard, pushing against her bra and wanting more, I looked down at her legs, and slid off the couch. She had to let go of my cock, and as I knelt next to the couch, I put my hands on her thighs.
She was watching and when I tried to undo the button on her jeans, she scooted back a little. Peyton again took a deep breath and when I started to unzip her pants, she reached down stopping me. Looking up, I knew she was nervous, unsure, but I smiled and moving up, I gave her a kiss. I didn’t want her to worry, and I didn’t want her to stop me either, and as she leaned back, I got up and sat next to her again.
She was smiling but I thought to myself, “Did I maybe go too fast?”
It did make me a little worried but then as we continued to look at each other, she said, “Can we slow down a little?”
Smiling back, relieved, I gave her a hug, and putting my hand on her thigh, I said, “Sure,” and leaned toward her giving her a simple little kiss.
The couch really wasn’t ideal and when I again moved my hand up to feel on her chest I thought, “Please don’t stop me.”
Looking at me, we eventually kissed and as our tongues again mingled in and out of each other’s mouths, I casually slid my hand down, letting my fingers search inside the front of her pants, now that they were open.
I again felt her smiling and as we continued to make out, she again slid her hand back to my crotch, feeling for my cock. It was getting a little more heated and when I felt the little band of her panties, sneaking my fingers under it, we suddenly stopped kissing. Looking at each other, I again hoped she wouldn’t stop me, but then giving me a subtle little kiss she suggested, “Maybe we should go to my bedroom.”
Smiling, surprised, I stood up and after pulling her to her feet, she leaned up on her tip toes and we kissed. Peyton took my hand now and holding her pants up with the other, she led me toward what I suspected was her bedroom.
Holding hands, going back toward a short hallway, and then through a doorway on the left, we moved over toward her bed. It was kind of dark, except for the light coming in from the hallway, and as I turned her to face me, she smiled. Smiling too, we again kissed, and then backing her toward the bed, I immediately lifted her up, sitting her on the edge.
Peyton giggled a little, and then leaning down, I kissed her. We were both smiling in anticipation, and when I casually tried to lift her top over her head, she seemed to hesitate at first.
However, giving me a sly little smile, Peyton obligingly lifted her arms up. Quickly, I got it over her head, and smiling, I cast her top toward a chair, missing it. Looking at each other for a moment, I couldn’t help but drop my eyes, watching her adjust her lacy little white bra. She was making sure it still covered her boobs and when our eyes again met and we smiled at each other I said, “You’re beautiful Peyton.”
She really had a nice little body and after a giving me a subtle little smile and a kiss, she slyly tried taking my shirt off too. I was a little self conscious, and hesitant being I was so much older. However, seeing her adventurous look, I lifted my arms, helping. I was in, well pretty good shape, but still was unsure how she’d react, being I was older. “It was now or never,” I thought and as I dropped my shirt off the edge of the bed, I could see her blushing as she looked at my chest and stomach. Looking up at me briefly, Peyton gave me a little smile, and then apprehensively reached out, touching my stomach.
Peyton seemed excited as she looked down and ran her little hand over my stomach and chest. It was nice to see her comfortable enough to play with the small amount of hair that ran up my stomach and covered my chest, and when she looked up at me and she smiled, I was glad she was okay with it.
Smiling back, I eventually put my hand on hers, and when she looked up at me, I leaned down and giving her a kiss, I laid her back. At that moment, I don’t think she knew what I was doing, however, as I casually slid off the bed and started tugging at her pant legs, trying to get them off, she smiled.
I so wanted to get them off, I wanted to see her pussy and her legs, and being they were already undone, they easily started to come off. Looking up at her, she seemed to smile, and then an attempt to help, she lifted her ass, which surprised me.
She was so petite and as I got her jeans down to her feet, and I pulled them off the rest of the way, Peyton reached down, adjusting her little white panties. They were sheer, almost see through and as I held her pants out briefly, I smiled and then dropped them to the floor. Instinctively, I look down at her crotch, and seeing her shapely legs and her little pussy pushing against her panties, all I could think about was wanting to be in her.
Smiling, I quickly look back up at her and then as I stood up, and started to undo my pants, Peyton leaned up on her elbows to watch. She was watching intently and when I let them fall to the floor, and I turned to face her, I knew see could see my cock bulging to get out. It was a little embarrassing and seeing her staring, I quickly adjusted it, which made her look up at me.
She had a concerned look, and when I told her, “Why don’t you scoot up,” she smiled.
Immediately when I climbed on the bed with her, she sat up. Kneeling in front of her, she continued to glance down at my crotch, and when I put my hands on her waist, she looked at me.
Giving her a kiss, I tried to pull her up, and then smiling, Peyton shifted a little, swung her legs under herself, and eventually got to her knees too.
I think we were both anxious, and as we continued to kiss, my hands again found there way up to feel on her boobs. I could feel Peyton smiling as we kissed and then as I reach my one hand around to her back, and quickly unhooked her bra with a simple pinch, Peyton immediately reached up, holding her bra against her chest.
It made us both stop kissing and as we looked at each other, I could see she was again overly concerned, but I couldn’t help it, I wanted to see. Peyton however, continued to hold her bra not letting it drop, even though the straps had slipped off her shoulders. Looking back up, I smiled at her, and when I reached over and coaxed the straps down her arms some more, she eventually dropped her hands, letting me take her bra off.
“Here we go,” I thought, and as I cast it to the floor, trying to not look down, I smiled, gave her a reassuring kiss and told her, “Don’t worry.”
She still had her hands on her boobs, covering them, but it did make her smile, which I was glad, but it was a slightly cautious one. Looking at her, I rose up a little, and now tried to pull my boxers down. It was a little awkward, but eventually I got them down enough to where I could leaned away, and pulled them over my feet.
I could see Peyton looking down, smiling and when I dropped them off the bed, I looked at her. She gave me a flirtatious smile and reaching her hand down, it was obvious she wanted to feel my cock.
It too made me smile, and as she got her hand around it, we both looked down. She had kind of small hands, but when she gave it a squeeze, feeling how hard I was, she looked up and remarked, “You’re big.”
It made me smile and then looking back down, she gave it another gentle squeeze. Moving to give her better access, I said, “I’m really not that big,” and when Peyton started feeling on my cock, rubbing and pulling at it, I hoped, “Maybe she’ll go down,” but really I wasn’t sure.
Peyton continuing to look down as she fondled my cock, I tried to lean back a little more, and deliberately lifting my hips, I hoped she might take the hint. Peyton eventually looked up smiling, and smiling too, she suddenly shifted a little and then as she actually started to go down, I thought she was just teasing me.
I didn’t think she’d do it, but as I continued to watch, she gently used both hands to pull the skin down and then smiling, she took it in her mouth. It was only for a few seconds, and when she looked up at me smiling, I couldn’t believe it, “Is she …,” but before I could finish my thought, she again took my cock in her mouth.
Peyton’s eyes were closed, and as I watched her move my cock in and out of her mouth, continuing to pull the skin back, slowly stroking it, and tonguing it, I sat back, trying to rest on my legs. It really felt good and whether or not she knew what she was doing, I closed my eyes and thought about wanting to cum.
Smiling to myself, I eventually reached down putting my hands on her head, and needing her to stop before she made me cum, I pulled her up. Peyton looked up at me and after glancing down briefly she ask, “What’s wrong?”
“Oh my god,” I thought, “no, nothing was wrong,” and smiling I continued to pull her up.
Peyton again glanced down briefly, obviously not wanting to stop, and as I lifted her chin to kiss her, she let go. Laying her back, she swung her legs out from under herself, and seeing her smile, I climbed on top of her. With her legs spread, Peyton scooted up a little more, and even though she still had on her panties, I made sure to press my cock against her crotch.
Peyton had leaned up on her elbows, and kissing her, I deliberately tried to slide my cock against her crotch, grinding against her. She was smiling shyly, but as our lips again met, she closed her eyes. I’m know she could feel how hard I was, and continuing to kiss her, continuing to grind against her, she grabbed a handful of the covers. Smiling, I slid down, kissing her chest, eventually finding myself passionately tonguing and sucking her little nipples. Peyton had subtly moved her hands to my shoulders and when I moved down further, kissing her stomach, I looked up smiling.
She was smiling too, and when I leaned away, and reached down to feel on her mound, she took a deep breath as I continued to gently rub it with the palm of my hand. Eventually, I found myself moving down, nuzzling against her pussy and as I held her sides, I could smelled her body spray or maybe it was her perfume. It was what I had wanted, and as I feistily grabbed each side of the thin band on her panties and started to remove them, she scooted up on the bed more, pulling away.
Looking up at her leaned up on her elbows, and seeing she was watching, I smiled and asked, “You okay?”
She was smiling and after a subtle nod I told her, “Don’t worry.”
It again made her smile, and as I tugged at the sides of her panties, Peyton laid back. Inching them down her thighs a little, she eventually lifted up slightly and then looking up, I quickly peeled them down over her ass. I could see Peyton smiling and after getting them over her feet, and casually tossing them over the edge of the bed, I put my hands on her thighs, shifting down the bed slightly.
She really was beautiful, pubic hair trimmed neatly, firm thin legs, and “My my,” I thought, “what a tight looking young little pussy.”
It made me anxious and looking up at her, remembering just how much younger she was, especially seeing that tight little body and pretty face. Smiling, trying to not look too hesitant, I again told her how pretty she was, which made her smile. We again kissed and when I again started feeling on her pussy, she inhaled, closing her eyes.
I wanted her to enjoy it and as my finger found its way into her slit, she again leaned up to watch. Trying to steady her, I put my other hand on her stomach, and after giving her a subtle smile, I went down.
Peyton squirmed a little, and when I got my head between her legs and I looped my arms up around them, she lifted up slightly, bending her legs. Seeing Peyton’s young little pussy was exciting, so young, so fresh, and when I spread her pussy lips, she laid back.
She again twisted a little, which made me look up at her. Peyton had closed her eyes, which made me smile and when I went in to tongue and lick at her young little pussy, smelling a mix of her body spray and her pussy I thought, “Mmmm.”
Immediately, I lapped at her clit, and closing my eyes, I concentrated on trying to get her off. I felt I had a chance and when she happened to start to squeeze my head between her legs, grinding, I tried to fuck her with my tongue as I rubbed her clit with my fingers. It kind of hurt, her squeezing my head but not stopping, she reached down, grabbing my head. Peyton was breathing hard and gyrating slightly, she asked me to stop. It made me smile, knowing she was going to cum, and when I didn’t stop, she pulled at my head, in an attempt to get me to come up.
Looking up at her, I could see she was flushed, and when I saw a little smile, I realized, “Yea, she must’ve cum.”
Smiling too, I climbed on top of her and after asking, “Are you okay,” I grabbed my cock and gently tried to guide it into her.
She was definitely wet and when I teased her tight little opening with the head of my cock, she reached up, pushing on my chest. I knew I needed to go slow and when she said, “Wait,” I looked at her.
Smiling, I laid on top of her, and adjusting my cock, making sure it was riding in her slit, I kissed her. I wanted to be in her and feeling her warm little pussy, I casually started sliding my cock, pushing it, moving up and down in her wet little slit. I didn’t stop, I wanted to fuck her and when we happened to stop kissing I questioningly remarked, “Do you want me to use a condom?”
I think it surprised her at first, but seeing her smiling tentatively, and then give a subtle nod, I too smiled and quickly slid off the bed. Grabbing my pants off the floor, and getting the one condom I had brought out of my pants pocket, I smiled as I held it out, showing her.
Moving back over to the bed I asked, Are you on the pill?”
She smiled, and again nodded saying, “Yea.”
I figured she probably was, and smiling I got back on the bed, opened the package, and looking at her I asked, “Do you wanta do it?”
Kneeling there, I hoped she might want to put it on, but seeing her hesitate, I smiled, and quickly went ahead and got the condom out of the wrapper. I could see she really wasn’t ready for it, but she was definitely curious, and when I put it over the head of my cock and started rolling it down over it, she looked down to watch.
Getting it down over my cock all the way, I looked up at her and after giving her a smile, I leaned up and gave her a kiss. I really didn’t want to use a condom but right now, I really didn’t care, and wanting to be in her, I laid her back, and then as I got on top of her a little more, and after a kiss I asked, “Are you okay?”
It made her smile and then smiling back, I reached down, grabbing my cock. Leaning up a little, guiding it toward her tight little pussy again, she squirmed a little as I worked the head of my cock up and down her slit. I knew it might hurt when I tried to push into her, and looking up I said, “If you want me to stop,” but before I could finish, she quickly leaned up and gave me a kiss.
Smiling, I slowly tried to push into her and seeing her gasp with her mouth open wide and then push on my chest, I stopped. I really didn’t want it to hurt and when she happened to pull away a little, I again asked, “Are you okay?”
Peyton let out a big breath and seeing an unsure smile and a shy little nod, I tried to smile too. I knew I needed to be careful and as we kissed, I again tried to push into her a little more. I again could feel Peyton clinching a handful of the sheets, bracing herself and being I was in her just a little way, I again kissed her.
Again, I thought, “Please don’t stop me,” but as I pushed into her a little more, she again pulled away a little.
I tried to ignore it, and not wanting to stop, I slowly tried to move my cock in and out of her, gradually pushing into her more and more. I was in her pretty much all the way now and when I happened to stop and we looked at each other, I smiled and again asked, “You okay?”
Peyton was smiling and when we kissed, she moved her hands to my sides. Pushing into her more, she again opened her mouth and after a gasp she remarked in a breathie voice, “You’re really big.”
She was smiling and it made me smile too, but I really didn’t feel I was that big. Kissing her, realizing that even though the condom was lubed, it probably was because she was so tight. Smiling, I told her, “Try to relax,” and after a kiss, I started trying to fuck her.
I was going to cum, there was no doubt, and wanting her to enjoy it too, I went slow. I tried to hold her and as I tried to fuck her a little faster, knowing she might stop me, I tried to concentrate.
Holding her under each arm, thinking, “Oh yea,” I whispered in an out of breath voice, “I’m gonna cum.”
She didn’t stop me and as I purposefully started bucking my hips into her, it didn’t take long. Peyton had passionately wrapped her arms around my neck hugging me, and when I pulled her close, wanting to cum, I started to fuck her more excitedly. Instinctively, I pushed deep into her and again telling her, “I’m cumming,” she squirmed, trying to pull away.
I knew it probably hurt, I didn’t want to stop, and when she again tried to pull away saying, “Stop,” I held her close telling her, “Don’t move!”
It shocked her I think and when I eventually did stop and I tried to kiss her, she turned her head. Holding her close as my cock jerked inside her, I again tried to kiss her. I’m not sure if she could feel it or not, but as cum surged, filling the condom inside her with warmth, and I gingerly started trying to fuck her again, she had to know.
I was done, and yea it really did feel good, but when I looked at her, and I tried to smile, I saw she was uneasy, I kissed her. Giving her a hug, holding her I asked, “Are you okay?”
I really didn’t want her to worry, but seeing it was, I continued to hold her, trying to keep my cock in her as long as possible. However, it didn’t take long before it quickly started to go limp, and when I slid down a little, and kissed her chest, I reached for my cock, wanting to make sure the condom didn’t come off as my cock pulled out.
Peyton’s hand had now moved to my shoulders, and I’m sure she felt me pulling on the condom, because she drew in a big breath as my limp cock slipped out. Resting my head on her chest and holding her sides I said, “That was nice.”
Yea, I should have said something better, and after a pause she asked, “Did you cum?”
I couldn’t believe she had to ask, but smiling, I casually said, “Oh yea.”
She had a concerned look, and really I didn’t want her to worry, but maybe it was just me, but I think she was suddenly starting to realize how old I was and, that she had let me fuck her.
I tried to smile, hoping she’d snap out of it but feeling the condom hanging heavy off the end of my now limp cock, I worried, “What will she think if she sees it?”
Embarrassingly, I tried to hide it and after telling her I needed to use the bathroom, I quickly turned, and slid off the bed, hoping she couldn’t see it. Not stopping, I ducked into the bathroom, and after closing the door, I pulled the condom off.
Looking at it, I remarked to myself, “Wow, that’s a lot,” and knowing I couldn’t just flush it, I balled it up in a tissue and tried to hide it deep down in her waste paper basket.
Cleaning up a little, I washed my hands and after gathering my composure, I opened the door and came out with a smile. Moving back over toward the bed, Peyton was wrapped up in the sheet, not really smiling, and seeing me come out and move over to where she was, she seemed to pull away. I tried to make the best of it, and when I sat on the bed I again asked, “Are you okay?”
Knowing she was maybe a little scared, I tried to give her some space and when she suddenly said, “I think I need to use the bathroom,” I stood up, giving her room to get off the bed.
She didn’t look at me and tried to stay covered with the sheet as long as possible, but eventually turned, dropped the sheet and went into the bathroom. She was in there for what felt like an eternity, which made me nervous. Sitting there, I didn’t know what to think, however as I looked down and I saw the condom wrapper on the floor, I quickly grabbed it, and stuffed it back in the pocket of my pants that were on the floor.
I was so nervous, but eventually, she did come out of the bathroom. She had a towel wrapped around her, and seeing she was thinking, obviously concerned about what we had done, I again tried to put on my best smile asking, “Is everything okay?”
She hesitated and then smiling guardedly she nodded and said, “Yea.”
Standing up, I moved over to where she was and as I hugged her I hesitantly asked, “Do you want me to leave?”
I didn’t want to leave and seeing she was unsure, I backed away telling her, “I think I’m gonna go.”
Peyton did smile, but it was an unsettled one, and as I grabbed my clothes off the floor and quickly started getting dressed, Peyton sat on the bed, watching.
It really was nice and I really wanted her to be okay, and then as I left, she said, “I had a good time.”
I knew she was just saying that, but it did make me smile, and after giving her a parting little side hug, I left. I hoped she’d be okay, I didn’t want her to worry, because I so wanted to be with her again. I did have her phone number, and I thought about calling her, but not wanting to appear brash, I decided to wait for her to call me.
She was probably thinking the same thing, or at least I hoped she was and even though we still saw each other now and then at the restaurant, and she was friendly, we never got together.
I do however feel we had a connection for a moment, but I also think because of our age difference, she has come to realize it just wasn’t right. I still flirt with her at the restaurant, but very carefully, all the time hoping there might be a chance, but as of now, it just hasn’t happened.