As we made eye contact, “Wow, very cute,” I thought and seeing them smiling, I smiled back and instinctively said,”Hi.” They were both giddy and after saying, “Hi,” they looked at each other and giggled. Yea, they were both very attractive, and up close, it was obvious they were way too young, but it really was tempting and as I looked at the one in those white short shorts, I half embarrassingly said, “Those are great looking shorts.”
Earlier this summer, I went up to where my cousin and his wife lived, to see a bunch of bands at an outdoor venue. The event spanned a few days, each lasting into the night, with bands playing pretty much all day. In addition, there were booths set up for various vendors and they had other activities, including competitions. Anyways, since this happens every year, a group of friends and I had planned to go months in advance, and as the date rolled around, we were all excited to go, at least I know I was.
Unbeknownst to me, this year would be exceptionally good time, not only because I got to hang out with friends, but I also ended up being with a very pretty young lady that was a surprise for many reasons.
It was the middle of summer, just before the Fourth of July weekend, and it seemed that every day at this event, brought out a new crowd and different vendors, and people watching was at a premium. We made sure to get set up early every morning, staking our claim with some chairs and a blanket, in the shade of a couple trees that was perfect for listening to the bands, watching people, and of course drinking beer.
As the final day of the event rolled around, I happened to spot an attractive young lady walking with her friend, a little ways away. They both looked to be very pretty, but pretty young too, and I couldn’t help but check them out as they passed. As I continued to look their way, one of the girls happened to look over at me, and seeing her smile as she took a spoonful of shaved ice, I couldn’t help but think, “That’s sexy,” as she seductively sucked on the spoon.
Continuing to check them out, hoping it wasn’t obvious as they passed, they both had nice little bodies and they were dressed almost alluringly in white shorts and tops.
“Oh my god,” I thought, “so attractive,” especially the one that wasn’t quite as tall, I thought was very attractive. She had on these white short shorts that she let ride up her ass, conveniently showing off her plump little ass cheeks. In addition, the white crop top she was wearing, draped over her boobs that seemed to accentuate them, but as I continued to look at her, I could see she really wasn’t that big.
Watching them as they meandered through the crowd, I knew they were both probably very young, but the way they were dressed, I tried to convince myself otherwise, and the more I looked at the two of them, the more I thought about being with the one in those white shorts. As they continued to move further away, I couldn’t get enough of that firm little bubble butt and her great thighs.
I knew I was staring, trying to take in as much as I could, and when she happened to reach back to adjust those ashen white running shorts, casually trying to get them out of her crack. It was to no avail and smiling to myself, seeing her ass cheeks still hanging out, I decided to go try to talk with her.
She really was a turn on and as they moved further away into the crowd over by the vendors’ tents, I wanted to see more, and standing, I decided to follow them.
I hoped I’d get up the nerve to talk to them, and as I got up, I smiled at my friends and said, “I’ll be right back.”
I’m sure they didn’t know what I was trying to do, because if they did, I know they’d have tried to shame me, attempting to stop me. In any case, as I headed toward where I last saw the two girls, trying to go around so I would deliberately run into them, I unfortunately lost track of where they were.
Frantically scanning the crowd, trying to locate the two of then, I suddenly said to myself, “There they are.”
As I got closer, intentionally looking away as I walked toward them, trying to be as inconspicuous as possible, I looked up suddenly, trying to act surprised. As we made eye contact, “Wow, very cute,” I thought and seeing them smiling, I smiled back. I think they were surprised to see me, and after casually looking them up and down for a moment, I instinctively said,”Hi.”
Giddy, they looked at each other and after giggling they too shyly replied, “Hi”.
In a tease I think, they looked me up and down now, and then smiling suggestively, they kiddingly jostled each other. Yea, they were both very attractive, and up close, it really was obvious they were way too young, but it really was tempting. Looking at the one in those white shorts, trying to get her attention as we moved a little closer, I half embarrassingly said, “Those are great looking shorts.”
I don’t think she got what I was saying right away, but as I turned slightly to see her reaction, I saw the two of them talking and then as she tried to look back at her ass, she suddenly looked over at me. She was smiling shyly and maybe a little embarrassed, because she again tried to quickly adjust her shorts as they hurriedly walked away.
I actually hoped she might feel a little flattered in a way, and when I saw they continued to playfully push and shove each other like school girls, it was obvious they were talking about my comment. Smiling to myself, thinking, “Man, she really is cute,” as I watched them walk away, hoping they might look back again.
Eventually, she did, and when we again made eye contact, she smiled as they huddled against each other. I smiled too and hoped that maybe we had made a connection but then as I ended up losing them in the crowd, I panicked thinking, “Where did they go?”
Looking through the crowd for them to no avail, I felt a little discouraged, thinking I’d never see them again, and felt I lost my chance, which was probably best. Going back over to where I had been sitting, I quickly found an empty chair. Somewhat despondent, I tried to not think about her, but her cute little ass and shapely body was definitely on my mind. I felt a little discouraged as I sat there, but I didn’t have to worry because, I think they must have been watching where I went, or remembered where I sat down, because later, the two of them just happened to swing by where I was sitting.
Of course I saw them coming my way, and sitting up, hoping to get her attention, I eventually stood up. Smiling as we looked at each other, I stepped out from the group and after saying, “Hi,” we shook hands, and introduced ourselves.
There was a brief pause, and being a little flustered knowing my friends were watching, I tried to block it out. Nervously smiling, I introduced myself and then listening carefully, they told me their names were Cassie, and Hannah.
Cassie was the one I really found attractive and as I stood there, all I could think was, “Cassidy Cassidy Cassidy.”
I wanted to make sure I remembered her name, and now being able to see them up close, Cassidy really was very pretty. Yea, her friend was attractive too, but she seemed to be more reserved, but when she said, “Yea, we call her Cassie,” which made the two of us look at each other.
As we talked, I casually tried to take in as much of Cassie as possible, but sensed that Hannah wanted to leave. Cassie was shorter, had brown, shoulder length hair, and steely green eyes. Hannah on the otherhand was a little taller, had longer, dirty blonde hair, and blue eyes. Continuing to look at each other, I became a little nervous, feeling my friends watching, but then as our conversation lulled, Cassie asked, “Why did you say I looked good in these shorts?”
It caught me off guard, I think it was meant to, but then after a moment I smiled and said, “Ummmm, well …”
I knew what I wanted to say, but didn’t feel it was appropriate, however after looking around I leaned forward and smiling said, “You’ve got a nice butt.”
I don’t think she was expecting it, because it seemed to embarrass her a little, and then as the two of them looked at each other, they smiled. Hannah then pushed Cassie, getting her attention and then turning, she smiled and simply said, “Thanks,” as she looked at me.
She had such a great smile and I hoped I might find the words to ask for her number, but being I was tongue-tied with how young she probably was, I couldn’t get the words out. After another awkward pause, we ended up shaking hands again, and then Cassie and Hannah walked off. Excitedly sitting back down, obviously smiling ear to ear, my friends asked, “What was that all about?”
Feeling a little embarrassed, I tried to shrug it off, and seeing them both look back, I wanted to follow them, but as I watched, they actually ended up sitting on a blanket a little ways away. They were more toward the front, where the stage was set up, and wanting to keep this casual encounter going, hoping I could think of a way to approach Cassie and maybe get her away from her friend.
Standing up, I took a deep breath and then deliberately walked past them, trying to get their attention as I moved toward the beer tent. Hannah saw me first, and after a nudge, Cassie turned and seeing her smile, I of course smiled too. She then turned back to her friend for a moment and then as I got closer, they both turned and smiling Cassie said, “Hi.”
Smiling, I said, “Hi again,” and then as we looked at each other, Cassie asked, “Where are you going?”
As I stopped, I pointed toward the beer tent and said, “I’m gonna go get a beer.”
Cassie and Hannah looked at each other and after a brief pause, I saw Hannah nod. Cassie then turned and facing me she smiled and asked, “Can I go with you?”
I was excited she wanted to go, but hesitant too, because I knew she was too young to actually get a beer. I felt they were playing me, and so playing along as we looked at each other, I innocently said, “Sure.”
Cassie and Hannah again looked at each other, and then smiling, Hannah gave Cassie a subtle push, coaxing her to get up. Cassie smiled apprehensively , and as I turned, and we headed away, Cassie cautiously looked back at her friend. I think we were both a little nervous, because we really didn’t saying anything as we walked over to the beer tent, but then as we stood in line, I casually asked, “How old are you?”
Hesitant at first, thinking about what to say, she eventually said, “I’m 21.”
I couldn’t help but give her a concerned look, I really hoped she was at least 18, but felt she was probably much younger given her immature mannerisms and, “Oh my,” her little body.
Don’t get me wrong, I liked it and I liked the attention she was giving me, but I knew I needed to be cautious. As the line to get beer started to move forward, and she saw them asking for ID, Cassie suddenly stopped and backed away saying, “I’ll wait out here.”
Pausing for a moment and looking at each other, I simply asked, “Do you want me to get you one?”
She again hesitated but then looking around Cassie smiled and then leaning toward me she whispered, “I’m really not old enough.”
I knew that, but then looking at her and seeing her smile, I nodded and asked, “What do you want?”
Cassie again seemed hesitant but after looking around, she smiled and blurted out, “Get me whatever.”
I couldn’t help but smile too, and as the line again moved forward, I shook her hand and said, “I’ll be right back.”
This made her smile and after a subtle nod, she stepped back a little more. Cassie then quickly turned and looking over at her friend, she waved, and gave her a thumbs up.
I couldn’t believe what I was doing, but felt if I was going to have a chance to be with her, getting her a beer was a start. After getting through the line as quickly as possible, I went back over to where Cassie was waiting. Smiling in anticipation, Cassie anxiously reached out for the beer, but when I didn’t give it to her right away she said, “Hey!”
Smiling, I told her, “Just wait,” which made her frown.
I didn’t hand her a beer right away, because I knew people were probably watching, and not wanting to bring attention to us, I quickly headed us back over where her friends were sitting.
As we got close, I could see there were a few new people sitting there, and as we stood at the edge of the group, I felt all their eyes were on us. It made me suddenly feel out of place, they were all so much younger than me, but when I saw Cassie’s friend, Hannah smiling at us, I felt it was okay.
Cassie now quickly grabbed the beer from me, and then smiling she sat down, and motioned for me to sit down too. As I looked at Cassie, she deliberately held out the beer, making sure Hannah saw it, which made Hannah ask, “Where’s mine?”
Looking at her suspiciously, hoping she was just kidding, I smiled and jokingly started to stand up, which made Cassie quickly grab my arm. Pulling me close and leaning against me telling, “No,” giving Hannah a friendly glare.
Feeling more at ease with what was happening, I later ended up getting us another couple beers, and yea this time I got Hannah too, which seemed to make her a little more accepting.
It was now starting to get dark, and as many of their friends moved up front to watch the band. As our conversation lulled, Cassie suggested we should move to a different spot. Looking at her, I immediately became a little anxious, wanting to be alone with her. However, I still felt people we’re watching us, but as Cassie stood up, and tried to grab the blanket off the ground, I accomidatingly got up too. Seeing us about to leave, Hannah blurted out, “Where are you going?”
She was obviously concerned for Cassie, being I was a stranger, and for good reason, being I was so much older than her, but Cassie told Hannah we were moving so we could see better. Turning and S
smiling at me, Cassie said, “Come on.”
Moving a little ways away, and spreading out the blanket, we quickly sat down. As we pretended to watch the band, and Cassie ended up huddling against me, I so wanted to make a move. It made me smile and then putting my arm around her, Cassie suddenly turned and asked, “How old are you?”
Looking at her, surprised, I tried to think of just how to answer her, but, “How?”
Seeing she was waiting for my answer, I just smiled and said, “Well, I’m a lot older than you.”
She seemed hesitant and like I said, I knew I was more than twice her age, but I think Cassie was intrigued and then smiling she said, “You must be around 30, huh.”
I knew was probably blushing as I smiled, and yea I guess, I felt a little flattered, but I also knew her naïve inexperienced was the reason she felt I was much younger. Cautiously looking at her, I managed to say, “No, I’m a little older than that.”
She didn’t press it but seeing she was looking at me questioningly, I quickly trying to change to subject, by holding out my beer and asking, “Want another?”
I had finished my beer and as she looked hers, she gave it a shake, and then downed the last little bit. Smiling at me, we both stood up and quickly headed toward the beer tent. We were both a little nervous and as we waited in line I asked, “Where are you folks?”
Cassie didn’t says anything right away, but then she explained that they had gone to a free concert over in the next town.
“Wow,” I thought, and then Cassie said, “Yea, they told me they were going to get a hotel over there.”
I liked the sound of that, but tried to contain my enthusiasm, thinking that just maybe, maybe there was a chance, and looking at her, I think she felt the same way. I definitely wanted to keep our conversation going and after going back and sitting down, I wanted to find out more about her and looking at her, I asked, “Do you have a boyfriend?”
I knew she probably did and figured he was probably there somewhere, but then as she hesitantly smiled, she told me, “Yea, but we just broke up.”
Asking what happened, she explained that he had cheated on her and then said they were through. Pausing for a second, and looking at her I said, “That’s too bad,” which made her half smile and then looking down, Cassie quickly replied, “It’s okay.”
The sun had gone down and the only light now was coming from the stage, but as I looked at her all I could think about was, “How can I get her alone?”
Like I said, “I liked being with her,” and felt there was a chance and when she turned and asked, “What?” I smiled and tried to shrug it off.
We of course continued to casually flirt with each other a little, touching and grabbing, and then as we looked at each other, I so wanted to kiss her, and maybe she wanted it too. In either case, when Cassie stood up, and grabbed the blanket, she smiled telling me, “Stand up.”
I’m sure her friends were watching, sensing I wanted more, and because of them, and I think our age differences, I felt a little uncomfortable to actually do anything. Cassie quickly balled up the blanket, and then looking at me she said, “Come on.”
Smiling as I got up, I desperately wanted to get her alone, but again knew her friends were watching. We ended up sitting a little ways away from her friends, a spot where we could be alone but still see the band play. I was still cautious, nervous to make a move, but as Cassie scooted closer saying, “Keep me warm,” I smiled and immediately put my arm around her.
Looking at each other, I pulled the edge of the blanket over our legs, which made Cassie cuddle against me even more, and as I put my hand on her leg, she playfully pushed against me, trying to get a reaction. Smiling, I pushed back, and when I tickled her sides, she giggled and wiggled, eventually reaching over, tickling me too. It was nice, and I hoped no one was watching, but being it was starting to get dark, I don’t think anyone took notice, at least I hope no one did.
She had a great smile and as we continued to mess around, I accidentally on purpose, pushed on her chest. Feeling her firm little tits, I Immediately looked up. It surprised me, and it obviously surprised her too, because as we looked at each other, she really wasn’t smiling, instead she looked guarded. However, when Cassie eventually smiled, I realized she was trying to ignore it, but for a split second, I sensed some apprehension.
“Oh my god,” I thought, it really was an accident, and worrying I might have over stepped, I apologized by simply saying, “Sorry.”
Smiling, Cassie said, “Don’t worry,” and then giving me a subtle push, she grabbed at my crotch.
Instinctively turning and smiling back at her, I said, “Hey!”
Cassie had scooted closer, and as I put my hands on her waist, and we looked at each other, I leaned toward her, hoping to give her a kiss. However, Cassie got nervous, pulling away, and looking around she said, Not now,” and the shyly looking down.
Smiling to myself, I reached up, and as I tipped her chin, and we both looked around to see if anyone was watching us,we again looked at each other. It seemed everyone was focused on the band playing and then pulling her close, we eventually kissed. It was only a little kiss, but it made Cassie turned her head, again looked down. She was smiling embarrassingly, and feeling it was my opportunity, I leaned toward her more and laying her back.
Laying next to her, our eyes continued to be fixed on each other, and as I casually moved to partially lay on top of her, Cassie closed her eyes as I kissed her. It was nice and then as we kissed again, I slyly brought my hands up her sides, casually trying to move her top. I wanted to see her tits, however Cassie quickly blocked me and leaning up and looking around she said, “Wait!”
Smiling, I really didn’t care if people were watching and when I again leaned toward her, and tried to kiss her, I moved my one hand down, trying to get in her shorts. Again, Cassie nervously stopped me, grabbing my wrist, and pushing it away, saying, “Stop!”
Looking at her, I felt a little dejected, but seeing a sheepish smile, it was obvious Cassie knew what I was trying to do. As we sat there waiting for the other to say something, I sat up. I didn’t know what to do or say, but suddenly without hesitation, Cassie said, “Why don’t we leave.”
“Really,” I thought, as she turned to stand up.
It definitely surprised me that she would suggest it and then smiling and quickly standing up too, I excitedly said, “Sure!”
Smiling, Cassie quickly grabbed up the blanket again and as she took it back over to where her friends were sitting, I watched. I could see Hannah was smiling at first, which made me smile too, but as Cassie explained she was leaving, Hannah’s demeanor suddenly changed, and when she grabbed Cassie’s arm, trying to keep her from leaving, I started to get a little concerned.
Looking over at me smiling, I hoped everything was okay, and when Hannah eventually stood up and they gave each other a hug, I could see they were smiling. Cassie and Hannah briefly held hand and then after a wave, Cassie came back over to where I was waiting. She was smiling, which was a good sign and as we left, and headed toward the parking lot, we ended up putting are arms around each other.
I knew it was for good reason that Hannah tried to keep Cassie from leaving, but it was nice to hold her and the thought of getting her alone were racing through my head. As we got to my car I thought, “Where can we go,” but remembering no on was home at her house, I immediately thought about taking her there.
Cassie must have been thinking the same thing because after getting in the car she said, “Let’s go over to my house.”
“Oh my god,” I thought, “yea, let’s go!”
Looking over at her and smiling now, I hastily leaned over the center console taking her hand. Eventually, we kissed and as she closed her eyes, I reached my hand slide up her side to feel on her right boob. She really was small, and when Cassie realized what I was doing, she shifted a little and pushed my hand down.
As we stopped kissing and we looked at each other, she gave me a sly smile and then reaching over, she groped on my crotch. I wanted her to feel how hard I was and when she finally felt it, I think it surprised her, because she leaned away and smiling asked, “Are you hard?”
Pausing and smiling back at her I said, “Oh yea.”
Cassie was smiling from ear to ear, maybe even a little embarrassed, but then after giving my cock a little squeeze, she leaned back and looking at me said, “Let’s go.”
Her house wasn’t very far away and after going inside, she led us down a short hallway and into what I suspected was her bedroom. Immediately, she went over and sat on the edge, and then laying back she said, “I’m tired.”
I knew she must have been joking, but looking at her, I moved closer and asked, “Tired, why are you so tired?”
Cassie, with out hesitation leaned up on her elbows and smiling said, “Well, it was a long day.”
I agreed it had been a long day and hot too, but as we looked at each other, and I moved closer, I got between her legs as she laid on the bed. Casually putting my hands on her thighs now and gently giving them a squeeze, Cassie looked up at me as she leaned on her elbows. Seeing her smiling, I moved my hands up to her sides, sliding them so her top inched up. Looking down at my hands now, Cassie asked, “What are you doing?”
I knew what I wanted to do, and as Cassie happened to look up at me, I asked, “Do you want me to leave?”
Of course I didn’t want to leave, I just wanted to see how she was feeling, and when we continued to look at each other for a moment, Cassie shyly asked, “Do you wanta leave?”
Smiling slyly, I slid my hands up her sides a little more. I wanted to see and feel on her boobs, but seeing she was still a little suspicious of my intentions, I instead leaned up and gave her a kiss. Kissing, Cassie closed her eyes and then after another little kiss, Cassie looked at me and shyly said, “That was nice.”
It made both of us smile and then after giving each other a hug, I again subtly brought my hands up, under her top. Moving my one hand to the front, wanting to feel her tits, I slid it up until it was under her one boob. Cassie didn’t stop me, but as we looked at each other, and my hands moved up and gently caressed her tits, she acted a little surprised, but again didn’t stop me.
She really was small and as we cautiously looked at each other, I tried to lift her top. I wanted to see her boobs, but Cassie feeling a little self conscious, reached up, stopping me. She didn’t have on a bra, she didn’t really need one, and yea she was rather flat chested but it still felt good to feel the coolness of her skin.
Looking at her, I subtly moved my hand down to her waist. I couldn’t help but smile as I desperately thought about wanting to see her tits, and when we again kissed, I boldly slid my hands up her sides again, under her top. Cassie’s little top immediately started to bunch up, and then opening her eyes and drawing in a big breath, I could feel her ribs. We eventually stopped kissing, and when I moved my hands around and cupped her little boobs again, she seemed a little apprehensive.
She didn’t stop me, but as I felt on her tits now, and tried to scoot her top up, she put her hands on mine, stopping me. Feeling her boobs and her little nipples was such a turn on, and when Cassie pushed my hands down, I politely moved my one hand down to her thigh.
Continuing to smile at each other, I put my hand between her legs. At first, Cassie didn’t realize what I was doing, however, as my hand moved up, she gasped a little. Quickly kissing her, as my hand up reached her crotch, and I felt her warm delicate little pussy through her short, my cock was so hard.
Again, she didn’t stop me, and feeling she didn’t have on panties, I pressed my finger into her slit slightly. Creasing her shorts, realizing she doesn’t have anything on under them I thought, “Mmm, I wanta eat her.”
I wanted to go down on her, but wasn’t sure how she would react, but feeling she might, I again pushed my finger into her, creasing her shorts a little more. Looking at each other, Cassie was wide-eyed and when I gently started rubbing her clit through her shorts, I think it shocked her a little, because she instinctively reached down, grabbing my wrist.
Pausing for a moment and looking at her I asked, “Are you okay?”
Cassie gave me a sheepish smile, and then when she nodded, I lean up to kIss her. I was so horny and as we kissed, I closed my eyes and tried to push my tongue into her mouth. I think it startled her a little at first, because she pulled back, but eventually opening her mouth a little, our tongues met. It was great and then as she turned her head slightly, allowing us to French kiss more deeply, I pulled her closer.
Smiling to myself as my tongue continued to dance with hers, I casually moved my hand trying to slip my hand down the front of her shorts. “Oh yea,” I thought, as we kissed, but then not feeling she had vert much pubic hair, I opened my eyes, surprised.
It didn’t stop me, I wanted to feel her pussy and when I eventually ran my fingers up and down along the sides of her tight little clamshell slit, we stopped kissing. Taking my hand out of her shorts, I smiled and after a simple kiss, I again asked, “Are you okay?”
I think Cassie was looking for reassurance and after giving a nod, I smiled and we again kissed. Putting my hand down her shorts again as we kissed, I felt her take another deep breath when my hand found her pussy. She was wet and as my finger slipped inside her and I gently rubbed her clit, I thought about wanting to fuck her. Taking my hand out of her shorts again, I immediately started tugging at them, trying to get them down.
Cassie eventually realized what I was doing, and reaching down, she stopped me. Looking up at her, she was smiling, and when she said, “Why don’t you take yours off first,” I couldn’t help but smile too.
Raising up on my knees, I quickly peeled off my shirt, and then looking at her, she stared at my shorts, and suggested I should take them off too. Smiling, I slid off the bed and as I stood there, I unbuttoned them, and let them fall to the floor. Kicking them aside and adjusting my now hard cock in my boxers, Cassie smiled and said, “Umm, take those off too.”
Looking over at her and seeing her smiling, I smiled too, and then nervously said, “Are you sure?”
I’m sure she could see my hard cock bulging against my boxers and when Cassie anxiously nod her head, I suggested, “You wanta do it?”
It caught her off guard I think, and then reaching my hand out, taking hers I coaxed her to get off the bed. Standing there looking at each other, I put her hand on my crotch and then said, “Ready?”
Immediately, she looked up at me and then as I started to inch them down, Cassie looked to see what I was doing. It was obvious she wanted to see what I had and as we both pulled down my boxers and my cock suddenly tumbled out, she stopped helping.
Looking at each other, I smiled, and as I continued to pull my boxers off, Cassie eventually looked back down and when she saw it, she was obviously hesitant. I’m really not that big but big enough and then as I held it I asked, “What now?”
There was an awkward pause as we stood there, but then smiling I grabbed her hand and pulled it down toward my cock. It was again obvious she had never done any of this and when she hesitated, pulling away a little. Looking at each other, I could see she was smiling, but I could tell she was nervous, and maybe a little curious too. As I again moved her hand, trying to put it on my cock, she actually grabbed it.
Cassie was examining it closely, and seeing her little hand on my cock was a turn on. As Cassie felt on it, she suddenly looked up and said, “You’re really big.”
I hoped she might go down on me, but figuring I better not push it, I lifted her back on the bed. Cassie had let go, and as she rolled to her side, shifting a little, I again tugged at her shorts. Lifting up a little, she smiled and then reaching down, she helped me.
Trying to be as nonchalant as possible, I couldn’t help but look at her pussy as I got her shorts all the way off and dropped them to the floor. She really was beautiful, and yea she was young, but still really pretty, and as I put my hand on her mound, and gently started rubbing, she rose up a little.
Looking up at her and smiling, I gently spread her legs, wanting to see more. Suddenly though, Cassie became self conscious, pulling her legs back together as she covered her pussy with her hands. “Oh my god,” I thought, but smiling I moved back up, again trying to lift her top up.
Cassie did stop me momentarily, but as I continued, she sat up, and lifting her arms over her head, she let me take it off. Dropping it to the floor, Cassie again embarrassingly crossed her one arm over her chest, covering her boobs, while at the same time covering her pussy with the other.
I didn’t want her to feel self-conscious, she was so pretty, and when she said, “Sorry they’re not very big,” I smiled and told her, “It’s okay,” and then said, “I like it.”
This made her look at me and seeing her smile, made me smile too. I didn’t want her to worry, because right now the size of her boobs really didn’t matter. I wanted to fuck her, and when I went to move her arm, and I looked at her, Cassie smile too, but nervously.
As she dropped her arm, exposing her chest, I moved my hand to feel on her budding little boobs. It was very apparent she was probably younger than 18, and when she suddenly blurted out, “I’ve never done this before,” I looked up at her.
I figured she hadn’t, and trying to put her at ease, I smiled and said, “Cassie, your beautiful.”
This comment made her look down and seeing she was blushing, I put my hand under her chin and then lifting her head I said, “Don’t worry,” as I gave her a kiss.
She smiled, and then as I continued to feel on her little breasts, I moved down, eventually tonguing and sucking her nipples. Cassie again took a deep breath, as I mouthed her nipples and took most of her boob into my mouth. Stopping, I laid her back now, and then climbing on top of her, I looked at her and said, “If you want me to stop, tell me, okay.”
Cassie nodded, which made me smile, and after giving her another little kiss, I kissed her neck, eventually making my way down her chest and stomach. I could smell her faint perfume or maybe it was a body wash, in either case, I wanted to taste her.
Putting my hand on her mound again, I looked up at her, and seeing she had her eyes closed, I got between her legs. Cassie quickly leaned up on her elbows and looking up at her, I smiled and then dropped my head between her legs. She now reached her hand down, touching my head and as my tongue dipped in her slit, she laid back again.
Eating her pussy, Cassie arched up a little, and as I put my hand on her chest, trying to steady her, I closed my eyes as I licked and tongued her little pussy. I wanted to try to get her off, but then Cassie suddenly reached down, grabbing my head saying, “Stop.”
I didn’t want to stop, but looking up at her and seeing a concerned look I asked, “Are you okay?”
Cassie nodded, and seeing her smiling guardedly, I smiled too and moved back up, casually wiping my mouth. Kissing her, I grabbed her sides and giving them a little squeeze I said, “Don’t worry.”
Smiling at each other, I again explained, “If you want to stop, just tell me.”
Cassie again nodded, but it was obvious she was nervous, and seeing this I kissed her again. Looking at me and smiling she told, “Just go slow.”
Telling her okay, I kissed her again, and then out of nowhere I subtly asked, “Are you on the pill?”
This made us both pause and then smiling Cassie said, “Yea, my mom put me on it.”
Giving a more serious look I smiled and said, “That’s a good thing.”
Cassie smiled too and then nodding shyly, we again kissed. Leaning off her a little, I grabbed my cock, and as I guided it toward her little opening, I stopped and asked, “Do you want me to use a condom?”
I didn’t really want to, and when she didn’t say anything I said, “I’ll be careful,” she unknowingly nodded.
Seeing she was a little apprehensive, I said, “Just relax.”
Cassie now laid back and as I moved up, I brushed the head of my cock against her pussy and then gently pushed into her. “Oh my god,” I thought, “she’s so tight,” and as I moved my cock up and down her slit and pushed a little harder, Cassie grabbed the covers, clinching them.
I knew it must have hurt, but I wanted to be in her and then as I pushed into her more, the head of my cock suddenly slipped in. Cassie immediately raised up and quickly pulling away, she exclaiming, “Ow!” which made me lifting off her, letting my cock slip out.
I knew it was uncomfortable and seeing a somewhat distraught look I asked, “Are you okay?”
Looking at each other, I could see Cassie was concerned, but then after taking a deep breath she said, “Just go slow.“
Smiling, I felt Cassie wanted to do it, and then as she put her hands on my waist, I looked at her and said, “Try to relax.”
Nervously nodding, she laid back again, and seeing she was really trying to relax, I again tried to push into her. Right away I struggled to get my cock in her even a little, and thought, “Oh my god, don’t let it hurt.”
Again, she was so tight, it was frustrating and when she felt me take in a deep breath, she asked, “What’s wrong?”
Desperately wanting to be in her, I didn’t say anything but then as I said, “You’re really tight,” she smiled and laying back Cassie told me, “It’s okay.”
Again, I didn’t want it to hurt but I knew I had to just push into her. Trying to go slow as I leaned into her, I hoped she’d relax enough to let me in. Looking at her, she put her arms around my neck, smiling and as I pushed into her a little, she wiggled and then holding me, I asked, “Are you okay?“
Cassie nodded, and seeing her continuing to smile, I kissed her and then hurriedly pushed into her. Immediately, Cassie let go of my neck and pushing me, exclaimed, “Ow!” as the head of my cock slipped in.
I knew it hurt and when she tried to pull away, I tried to hold her still. Telling her to relax, Cassie twisted and grabbing a handful of the covers she said, “Stop!”
Pulling out, I hoped she’d relax, but seeing it was obviously hurting and feeling Cassie arching her back, attempting to get me to stop, I slid down a little kissing her chest. Frustrated as I continued to hold her, I let it slip all the way out of her. Cassie then took a deep breath, noticeably relieved and then seeing her smile, I asked, “Are you okay?”
She had her eyes closed tight, but nodding and smiling she again wrapped her arms around my neck. I hoped she was okay, and I hoped she let me try again, and after giving her a kiss, I asked, “Do you want me to stop?”
It made her pause for a second, but then opening her eyes and looking at me, Cassie simply said, “It hurts,” and then said, “I don’t know.”
Immediately I asked, “Maybe we should stop.”
Again, I really didn’t want to stop and hoped she’d let me keep trying, and seeing her apprehensively smile and not say anything I said, “Let’s try it again.”
Looking at me, Cassie smiled, and then nodding, she took another a deep breath. Smiling too, I said, “Try to relax,” which made her shifting a little, as she laid back.
I knew she was trying to get comfortable, and then as I slowly pushed into her a little and then took it back out, I hoped she’d relax. I wanted it to work and then as I gently wiggled the head of my cock in her wet little slit, and I felt her relax, I pushed into her. “Mmm,” I was in her, but as I guided my cock into her, every now and then, Cassie wanting to wiggle free.
Again, telling her to relax, I slowly tried to move my cock in and out of her, Cassie again grabbed a handful of the covers, continuing to squirm. It did feel good to be in her and I hoped it wasn’t hurting to much.
“Mmm,” I thought as I continued to push into her.
I wanted to cum, and as I started to fuck her, moving my cock in and out, I knew it wasn’t going to take long before was going to cum.
Holding her and kissing her, trying to fuck her, I continually tried to reassure her by softly asking, “Are you okay?”
Cassie again nodded saying, “Just be careful.”
Right now, I didn’t want her to worry, I wanted her to know everything would be okay, because there was no doubt I was going to cum, that’s if, she didn’t stop me. Trying to be as careful as possible, continuing to move my cock in and out of her, I wanted to cum. Bucking my hips into her a little faster and a little deeper, holding her and kissed her, I felt it.
“Oh my god,” I thought, “I’m going to cum,” and as I held her close, giving a couple deliberate pushes into her, my cock started to jerk inside her.
I was out of breath and when I stopped briefly and said, “Oh shit!” she raised up and asked, “Are you okay.”
“Oh yea, I was okay,” and then as my cock faintly buck and cum drained inside her, I again slowly moved in and out of her.
Stopping and holding her I kissed her cheek and said, “Yea, I’m good.”
Continuing to lean up, sensing something was wrong, Cassie pushed on me hastily asking, “What are you doing?”
Continuing to hold her, not saying anything Cassie said, “Don’t cum in me!”
Leaning up and quickly pulling out I thought, “Oh my god!” as I moved down.
It was too late, and seeing she was distraught as she pushed me to get off her, I grabbed my cock and knelt in front of her. It felt good to have cum, but as Cassie sat up and saw me inconspicuously squeeze the last little bit out, she hastily reached down to her crotch.
Watching her and seeing her reaction as she felt the sticky slippery cum that was oozing out of her, I moved to lay next to her. Bringing her hand up and looking at her fingers, it was obvious she was upset, and then showing me she said, “I didn’t want you to cum in me.”
Not knowing how to respond I simply smiled and said, “Sorry.”
Looking down as she frantically fingered her pussy, trying to get it out, I could see cum had spilled out onto her bed. Wanting to reassure her it would be okay, I put my hand on her leg, and then patting her thigh I said, “It’ll be okay.”
She was definitely upset and after a pause, Cassie quickly rolled off the bed, and hurried into the bathroom, closing the door behind her. “My god,” I thought, “what if she’s not actually on the pill.”
Worrying as I lay there, thinking why she didn’t say something sooner, I asked myself, “Why didn’t I thought about it too.”
Eventually, I heard the bathroom door open and as she came back in the bedroom, I tried to smile. She had a towel wrapped around her, making sure it covered her and then without looking at me she wistfully said, “I think you should probably go.”
I understood what she was feeling and not saying anything, I got off the bed and started getting dressed.
Pulling up my shorts and putting on my shirt, I tried to reassure her by asking, “You’re on the pill, right?”
Cassie didn’t say anything right away but then as she sat on the edge of the bed, she said, “Yea, but I didn’t want you to cum in me.”
Again, not knowing what to say, I finished getting dressed and as I started to leave, Cassie followed me. Turning for a second, as I got to the door, I said, “Don’t worry, okay.”
This seemed to make her half smile and then after looking at each other, I walked out and she closed the door. Leaving, I wanted to keep in contact with her, but how? I didn’t have her number and didn’t live in that town, only visiting a few times a year.
Before I headed home, I decided to swing by her house, wanting to see her. However as I drove by, I saw there was a car in the driveway, and figuring it was probably her parents, I kept driving. I just wanted to make sure she was okay and maybe get her phone number, but mainly I wanted to make sure she was okay with what had happened and hoped she didn’t get pregnant in case she really wasn’t on the pill.
I have visited my friends up there and I’ve driven by her house, but as of now, I haven’t run into her. I continue to see her little butt whenever I think bout her and hope we’ll see her again. I do however, worry about what kind of reception I will get if we see each other.