I was an older guy, in pretty good shape, not married, and when I attended a friend’s outdoor barbecue, i was lucky enough to thrust into a situation where I could be with Anna, the daughter of one of my friends that was attending the barbecue.
Periodically, a group of my friends get together in the summer to have a backyard party to catch up and to have a little fun, just hanging out. This particular time last summer, when I was invited to a friend’s house for a barbecue, I was reluctant at first but would be glad I decided to attend.
The day of the party all started out very innocent, and when I finally got there, there were already a bunch of people talking and drinking, so I dove right in, trying to socialize with some friends on the back porch, quickly trying to polish off a couple beers.
I really wasn’t expecting anything to happen but when I suddenly found myself in a conversation with Anna, the daughter of one of my other friends, as her parents stepped away, I instantly became very nervous seeing how attractive she was. Anna became a little nervous too I think, and after excusing herself, she moved over to where her parents where standing.
We knew each other casually and even as a young girl, Anna had an alluring look. However, now being that she was probably in her late teens and taller, she was even more attractive. She was light skinned, had long blonde wavy hair, pretty brown eyes, a sexy smile, chubby cheeks, and being she was still kind of young, she seemed to have what I would call, “A little baby fat,” but she definitely wasn’t fat.
I wasn’t really sure just how old Anna was now, but when I saw that her parents were allowing her to drink, I felt she must be at least 18 or 19. Anna looked to be having a good time, talking loudly and laughing with people and as I continued to look at her, I felt she was actually trying to get my attention, which wasn’t hard.
She had her hair loosely braided, which allowed some of it to wisp around in the wind, and the pink lips stick she was wearing, trying to look older was really attractive, especially when she smiled. She had on a short blue jean skirt, which showed off her legs, a loose fitting, off white tank top, no bra that I could tell, and some hoop earrings and pink leather bracelets.
As I continued to look at her, it was obvious that she didn’t really expect to see anyone she knew, because whenever she saw me looking her way, she seemed to shy away, constantly looking down, adjusting her top and skirt, wanting to make sure she looked okay.
At the time, I was probably more than twice her age, but even with that, I had always thought about being with her and even though I was in pretty good shape, and not married, there was no way I would ever consider pursuing her, well maybe.
Eventually, I was able to approach her when she happened to be standing by herself and as I tried to keep our conversation light-hearted, joking around as we chatted, Anna ended up pushing against me, and laughing, trying to act older. It was nice but when Anna suddenly reached up, and gave me a hug, I found myself smiling, and as I instinctively hugged her back, I suddenly realized I could feel her firm little boobs pushing against my abdomen.
Holding her away from me now and looking at her worrying, there was an awkward moment. I was pleasantly surprised and when I saw her smiling and looking down at her chest, adjusting her top, I had a feeling she had deliberately pushed her tits against me, trying to get my attention, which she did.
Nervously looking around now to see if anyone was watching, and seeing that everyone was preoccupied, I turned back and seeing her smiling, I quickly hammered down my beer, trying to hide my embarrassment.
After slurping down the last little bit, I smiled and shaking my empty beer can, trying to signal I needed another I said, “I’ll be back,” and then asked, “Do you need one?”
I really just needed time to gather my thoughts and as I turned and headed over to the beer cooler, all I could think about was how, “How could I get her alone?” but there was no way.
I had always been attracted to Anna before, but she was so young, and yea I had thought about being with her in the past, but there was no way for many reasons. She was always very friendly and being I hadn’t seen her in a few years, she had definitely grown up and as I looked at her while I stood by the beer cooler, I again started to fantasize about being with her.
Thinking back to this moment at the barbecue, I finally realized that she had probably been trying to give me hints that she was interested for a long time, but naively I never got it. As I regained my composure, and continued to check her out, I thought, “How nice to be able to talk to and socialize with her,” especially now, since I felt there was an attraction.
Anna definitely had a sexy look about her and as I watched her drink her beer, it seemed that every time I looked her way, she was looking my way too. Taking a deep breath as I moved back over to where she was, I was cautious, but as I smiled and we again started talking, Anna said, “Sorry.”
I wasn’t sure why but when I asked, “What for?” she said, “For giving you a hug.”
I was really okay with it and after looking down at her chest I replied, “It just surprised me.”
Anna smiled seeing me looking down at her boobs and after shaking hands, she glanced over to where her parents were standing. Looking over at them too, Anna held up a finger, signaling for me to wait, as she smiled and walked over to them.
Standing there watching Anna and her parents, I thought, “Maybe there always was something,” trying to justify that even though she was really young, and our ages were so greatly different, it would be okay.
Anna’s parents wanted to leave but for obvious reasons I think Anna wanted to stay, and seeing her parents talking with Anna and gesturing my way smiling, I was scared that maybe I got caught messing with her. As they started to walk toward me, I got scared, and nervously moved over to the table of hors d’oeuvres.
Cornering me and saying, “Hey,” I casually turned, and smiling said, “How’s it going?”
Anna’s father smiled and half jokingly said, “Are you trying to avoid us?”
Worried, I looked at Anna and seeing her shyly smile, I apprehensively looked back at her parents. They too were smiling and as I shook hands with him he said, “Hey, my wife and I want to go home,” and then said, “Anna really wants to stay,” and continued by saying, “she suggested that you might be willing to take her home when you leave.”
“What a relief,” I thought, and smiling I again looked at Anna.
They actually lived kind of near where I did and it wouldn’t be too out of the way to drive her home, but as I thought about being alone with Anna, I didn’t know what to say. However, as I glanced over at her, she tilted her head slightly and smiling questioningly, I smiled, and turning to look at her folks, I agreed, “Yea, that should be okay.”
Looking at Anna smiling, she immediately moved away, not wanting to betray her feelings, and as I watched, she eventually stood away from us, continuing to curiously smile as she sipped at her beer.
Shaking their hands again and smiling, they walked over to where Anna was standing and after talking briefly, they waved and ended up leaving.
Anna really didn’t have friends at this party that I could tell and as she meandered around the porch, I ended up casually moving to where she happened to stop. Looking at me as I said, “Hey,” she turned giving me a fake surprised look, and as we smiled at each other I said, “Let me know when you want to go.”
As we looked at each other, I could tell she definitely wasn’t feeling any pain and as we talked, continuing to laugh and playfully push on each other, I wondered, “How many beers have you had?”
I figured that I probably drank 3 or 4 and as we continued to flirt with each other, it wasn’t long before she was hanging on me. Looking around, hoping no one noticed and feeling that maybe the drinking was catching up with her, I asked, “Ready to go? “
Trying to keep her at an arms length was tough; I wanted to be with her and I felt she wanted the same thing, but right now she was a little drunk and all I could think, “She’s way too young and she’s your friend’s daughter.”
Feeling I was getting a little caught up in the situation, and seeing the party was starting to wind down, I told her we should probably get going. Anna was definitely a little more than just tipsy now, and after a smile and a nod, she stepped toward me stumbling. Grabbing my arm, trying to keep from falling, I smiled but knew we needed to go.
Telling her to wait there, I went over to the couple that was hosting the barbecue and explained that I needed to take Anna home. Seeing she was a little drunk, he patted me on the back and smiling said, “Thanks for coming,” and after I shook their hands, I gathered up Anna and we left.
I wasn’t sure if Anna was drunk, or maybe tired, but in any case as she continued to hang on my arm, I thought about how easy it would be to take advantage of her, but having conflicting thoughts, I tried to focus on getting her home.
As I drove, she leaned over the console continuing to hang on me, which made me nervous to the point where I had to ask her to stop. Anna suddenly seemed a little sad, put off and as she sat back, I glanced over at her. I didn’t want her to be sad but felt she was overly sensitive, being she had had a little too much to drink, or maybe, she was actually trying to signal her openness or maybe it was a little of both. In any case, she again grabbed my hand and as I looked over at her a little surprised, Anna slurred, “Do you think I’m pretty?”
Surprised, I glanced over at her briefly and thought, “What was she trying to get at?
As I looked back at the road searching for what to say, she pulled on my hand, wanting me to say something.
“Anna,” I said, “you’re very pretty,” and as I glanced over at her, she smiled.
This made her again lean over and as she grabbed my arm and hugged me, she said, “Can we go by your house?”
I couldn’t believe it and as I looked over at her, Anna gave me those big eyes as she tipped her chin down and when I asked, “Are you sure,” she nodded and smiling, she pulled my arm close.
I already had a hard on but being able to feel her little tits again pushing against my arm as she held me, it was almost uncomfortable.
Telling her, “Okay,” Anna smiled and sitting back, she took a deep breath as she continued to hold my hand.
I felt she was wanting to sober up a little now, and seeing her close her eyes I thought, “What was I doing?”
As I continually looked over at her as I drove, I hoped she’d change her mind, but deep down, I really wanted to be alone with her. When I happened to look over, I could see that Anna’s little blue jean skirt had hiked up a little as she slouched in the seat. Seeing her legs, I found myself reaching over, and as I put my hand on her thigh, I asked, “Are you okay?”
Not opening her eyes, she moved her hand on top of mine and nodding she smiled. It was already getting dark as we pulled into my neighborhood, and as we headed down my street I asked, “Are you sure you wanta stop?”
Nodding her head again, I took a deep breath and putting my hand on top of hers now, I gently squeeze it as we pulled into my driveway. Opening her eyes, and unbuckling her seatbelt, she slowly started to get out. As we exited the car, Anna said, “This is nice,” as I took her hand, and tried to usher her up the walk.
As we got to the front door, she suddenly seemed a little unsure, but as we went inside, she seemed to have sobered up a little. Going over to the living room and sitting her down on the couch, I asked, “Do you want something to drink?”
Anna immediately asked, “Whatcha got?”
Knowing she didn’t need anymore alcohol I suggested, “How about a Coke?”
Coming back out to the living room and sitting next to her, I handed her the Coke and as she set it down Anna leaned forward and asked, “Wanta show me around?”
Looking over at her suspiciously, she said, “Come on.”
I felt she had an ulterior motive, but smiling, I stood up and as I took her hand, she stood up too.
Showing her the kitchen briefly and then only pointing down the hallway where the bedrooms were, Anna hastily pulled my hand saying, “Show me your bedroom!”
As we made our way down the hall, I pointed out two small bedrooms and a bath, but that didn’t interest her, she wanted to see my room.
As we went into the bedroom at the end of the hall, I said, “Okay, this is it.”
Seeing her smiling as she looked around, I pointed out a small bathroom that was at the back, and as she moved about the room, I suddenly cut her off. Looking at me smiling, she got up on her tippy toes and throwing her arms around my neck she said, “This is awesome.”
Looking at her I asked, “Why did you want to come by here?”
Letting go, and nervously moving away from me, she turned and as she looked at me she said, “Do you really think I’m pretty?”
I knew what she wanted and it made me a little nervous, but I so wanted to be with her. Smiling, I subtly moved over to where she was standing and as we looked at each other, I put my hands on her waist and said, “Anna, your very pretty.”
Anna blushed and as she leaned up on her tippy toes again, we kissed.
I had wanted this but now that it was right in front of me, I was apprehensive.
Backing her up against the bed, I immediately reached up feeling her chest and as she felt on mine, I kissed her. She didn’t have on a bra and when I tried to pull her top up over her head, she lifted her arms, letting me. Looking down at her stomach, Anna had a belly button piercing and when I saw it I jokingly said, “Do you have any other piercings?”
Looking down, Anna slyly said, “What do you think?
Smiling, I quickly threw her tank top aside, and again reached up with both hands to feel on her boobs. They were cool to the touch and as I leaned down to kiss her, Anna tilted her head to one side. As we kissed, I immediately tried to push my tongue into her mouth. I think it must have surprised her at first but as she opened her mouth and our tongues met, I moved my one hand down under her skirt, to feel her crotch.
She wasn’t stopping me and maybe she should’ve but when she scooted my shirt up, trying to get it off, I immediately helped her, taking It off and tossing it on the floor. As we again kissed, I searched for the front button on her skirt and when I found it, I quickly got it unbuttoned and then unzipping it, I let it fall to the floor.
Backing away to look at her, Anna became self-conscious trying to cover herself. Looking at her as she tried to cover her boobs and seeing her white little panties, I immediately undid my shorts and pulled them down, kicking them off.
Pulling her close, kissing her, and being able to feel her cool, naked body against mine, made me so hard. She had to have felt my cock pressing against her as we kissed, because Anna suddenly reached down groping for it.
Instinctively reaching down too and putting my hand on her pussy, I immediately dipped my finger into her slit through her little white panties. Feeling how wet she was, I immediately decided to help the situation by hastily pulling down my boxers as we continued to kiss. Getting them down to my knees, we stopped kissing and as she watched me wiggle them down the rest of the way, and stepping out, I pushed them away with my foot
Anna now had full access to my cock and when she felt how hard it was and how big it was, she looked up at me, concerned. Smiling at her, I helped her stroke it and as she looked down to watch, I pushed on her shoulders to go down to her knees. Looking up at me again, she smiled and as she knelt down I said, “Go ahead.”
As she looked at me holding my cock, I could see she was apprehensive, but as I started rubbing it , I said, “Open your mouth.”
She was definitely scared and after a pause I quietly said, “Close your eyes.”
Anna again looked up at me, and hesitantly said, “I’ve never done this before.”
Putting my hand over her eyes, having her close them, she reluctantly opened her mouth. Carefully trying to put it in her mouth, not wanting her to stop me, I accidentally touched the head of my cock against her lips.
Pulling away and opening her eyes, Anna looked up at me, unsure. Not wanting her to be scared, I pulled her to her feet and smiling at her I told her, “Don’t worry.”
Anna nodded and then said, “Sorry, I’m just a little scared.”
Holding her, I again said not to worry, and as she hugged me back I asked, “Do you want me to take you home?”
Hesitating, Anna shook her head, “No,” and as I continued to hold her, I kissed her on the head and then lifting her chin to look at me I said, “I’ve always wanted to be with you.”
That made her smile and as we kissed, I backed us up to the bed. We were both naked and as I lifted her up on the bed, she nervously giggled. Scooting her over and climbing on the bed with her, we kissed and as we started to make out, I laid on my back. Ann’s leaned over me and as she rubbed my cock and looked up at me smiling, I said, “I’ve always wanted to be with you Anna.”
Leaning against my chest hugging me, I could see she was smiling. Grabbing her and hastily trying to pull her on top of me I said, “Come on.”
Anna again giggled a little as she straddled my waist, and seeing her blushing, I smiled. As she shifted a little trying to get comfortable, I reached up to feel on her little tits.
Anna instinctively put her hands on mine, making me stop and as I looked at her, I moved my hands down to her waist. Giving her waist a little squeeze as we looked at each other, I eventually found myself reaching behind her, wanting to finger her pussy. Putting my hand up under her from behind, she lifted up slightly and when I felt her little slit, I immediately spread her pussy lips and quickly dipped my finger into her wet little pussy. Looking up at her, she had her eyes closed, and as she mumbled, “Mmmm,” she leaned forward, spreading her legs as she straddled my waist.
Asking her if she was okay, she opened her eyes and leaning forward we kissed. She seemed to be into it and as Anna leaned back smiling, she reached one hand back, taking hold of my cock. Looking like she was in a trance, she immediately started trying to work it in her little slit as she moved back.
She was so tight but as she leaned back and gradually got my cock in her, I could see it must have been a little uncomfortable, but at the same time as she kept her eyes closed, there was some pleasure in her face too.Anna now suddenly leaned forward to kiss me, which made my cock inadvertently slip out, and so I quickly reached behind her, grabbed my cock and immediately tried to guide it back in. As I blindly tried to push into her, I ended up pressing my cock against her tight little butt hole, which made her reach back and as she looked at me smiling she said, “Wrong hole.”
Letting go and smiling, I let her guide my cock, and as it slipped into her, she leaned back, taking it almost all the way in. Grabbing her ass and helping her move up and down so my cock was going in and out of her, I gently spread her ass cheeks.
It was such a turn on watching her pretty face as she leaned back, and then again, having her full little tits and puffy nipples in my face as she leaned forward had me wanting to cum.
Excitedly, as I continued to spread her little butt, and I moved my fingers closer to her puckered little hole, Anna mumbled, “Mmmmm,” which I felt let me know she liked me touching her there.
Looking at her as I spread her ass a little more, and making sure to dab at her tight little hole with my finger, I could feel her tighten up. Quickly looking down at me, I could see her slyly smile, and as I smiled back, I pressed my finger into her ass. Instinctively, Anna rose up a little, but then as she settled back, she again closed her eyes. She had a big smile and when I pushed my finger into her a little more, she wiggled a little.
Keeping my finger in her ass as she started moving up and down on my cock, I really felt she was into it and as she continued to bob up and down, I felt I was going to cum.
Putting her hands on my chest, she looked at me and when Anna smiled and lean forward to kiss me, my
cock suddenly slipped out again. I quickly reached behind her and taking hold of my cock, I deliberately tried to push it into her ass. Anna immediately looked at me, knowing what I was trying to do and lifting up, she again stopped me saying, “No, don’t.”
Anna smiled slyly and pushing on my chest, I really hoped she might be receptive to trying but it was obvious she was apprehensive about it. As I looked at her though I said, “Sure you don’t want to try.”
Shaking her head and smiling, she paused but then said, “No.”
Leaning up and kissing her, I sadly said, “Okay.”
Having her sit up again, continuing to straddle me, it was obvious that she was concerned and when I told her again to relax, she nodded. Being she was still a little drunk, and maybe she was a little curious about trying it, but I let it go. Reaching behind her again and trying to guide my cock into her pussy, Anna reached back making sure I put it in the right place.
Looking at her face as she inched back, letting my cock slip into her pussy, as I felt on her tits, I could see it must have hurt a little. Moving my hands down to her waist and thrusting my hips up a little, trying to push into her a little more, Anna suddenly brought her hair forward, tossing it so it partially covered her chest, and trying to smile as she leaned back on my cock, she said, “Ohh … fuck,” as she put her hands on her tits, gently squeezing them.
Moving my hands up to feel on her tits too, she leaned forward again, so my cock slip out. Seeing it must have been hurting, I rolled her to her back and as I got on top of her and kissed her, I immediately tried to put my cock back in.
Pushing on my chest and telling me to wait, I looked at her and as I moved down I asked, “Are you okay?”
Nodding Anna said, “Give me a minute, okay.”
Smiling, I moved to suck her neck and as I closed my eyes and moved down to suck and tongue her puffy little nipples, I hoped she’d still let me fuck her. Continuing to move down, I ended up kneeling between her legs and as I rubbed her thighs, eventually rubbing her pussy, she seemed to relax.
I wanted her to relax and when I scooted down further and kissed right above her slit, she leaned up on her elbows to watch. Glancing up smiling, I put my hand on her chest trying to steady her as I went down to eat her pussy.
Smelling her and tasting her was such a turn on and as Anna laid back again, I had her spread her legs and bend her knees. As I licked and sucked on her pussy, she put her hands on my head. I knew she liked it, but I also knew I wanted to finish, and feeling I was in somewhat of a hurry, I moved back up and as I asked if she was okay, she nodded, a she continued to keep her eyes closed.
Smiling, I reached down and as I tried to push my cock in her again, she pulled away. I had to be careful because it was obvious she was tender and so I tried moving my cock up and down her slit, hoping she’d relax enough so I could get my cock in her.
Pushing into her again, it suddenly slipped in, but Anna again pulled away and as she pushed on my chest she said, “Go slow.”
Pulling out a little and stopping for a moment, I soon ended up moving my cock in and out, trying to fuck her, hoping she’d relax. Hunching over her one shoulder, with both of my hands under her shoulders, she put her hands on my back and when I heard Anna say, “It’s okay,” and then say, “I’m okay,” I really hope she was, but knew it was still hurting a little.
Trying to concentrate my thrusts, hoping she’d relax as I tried to be careful so it didn’t hurt too much, I still tried to focus on cumming.
She really was tight and almost immediately I was close, but as I continued to focus, I suddenly felt her body go limp, which made me stop and ask, “Are you okay?”
Seeing her nod as I looked at her, I again started fucking her, knowing I needed to hurry and when I was ready to cum, I hoped it wouldn’t hurt. Trying to be careful as I slowed, holding back, so the pressure would build a little before I came, and breathing hard, I quietly told her, “I’m gonna cum.”
She immediately moved her hands, from my ass to pushing me to stop as I held her down, pushing deep into her. Stopping as cum pumped deep in her pussy, she seemed to whimper a little, which scared me.
Anna laid back now, obviously sensing that warm cum had spilled inside her as my cock continued to faintly jerk. It felt so good to cum and when I started to slowly move my cock in and out of her again, Anna tried to wiggle free.
My cock soon started to go limp as I held her and when it slipped out, I scooted down kissing her chest. Lifting off her, I heard a little air escape from her pussy and instinctively looking down, I could see a little cum seeping out onto the sheet. As I continued to look down, Anna again leaned up on her elbows and seeing her smiling, I hoped she was okay.
As I rolled to my side and laid next to her, Anna leaned over and smiling she asked, “Did you cum?”
Smiling and nodding my head, she again smiled but then with a concerned look, she laid on her back and spreading her legs, she reached down touching her sticky little pussy. Feeling the cum oozing out of her, she brought her cum covered finger tips up, and showing me, she looked scared.
Immediately she reached back down, and as I watched, she vigorously fingered her pussy, trying to get it out. Anna now gave me a concerned look, and as we continued to look at each other, not saying anything, she looked a little mad as she slid off the bed.
Looking back at me briefly, with her legs clinched together, she turned and stumbled into the bathroom. As I sat there, I hoped she’d be okay, but I continued to worry, as I waited.
Anna finally came out with a towel wrapped around her, trying to cover up and as she came over to the bed I asked, “Are you okay?”
Anna simply nodded and after a brief pause I said, “I should probably get you home before your parents start to worry.”
She was obviously tired, and maybe a little mad, but after another little nod, we both quickly got dressed. Hurrying her home now, we didn’t really say anything, and as Anna closed her eyes trying to fall asleep, but she always woke herself up when her head would happen to dip.
As I pulled up front, Anna took a deep breath and not saying anything, she quickly hurried up to the front door, and as she went inside, I did a u-turn and headed home. Continuing to worry about her as I drove, concerned she might say something to her parents, it was hard to sleep.
The next day, I got a text from Anna’s father saying, “Sorry, Anna was kinda drunk last night.”
I didn’t know what to say, but responded with, “Is she okay?”
He texted me back, “Yea, she threw up last night, but she seems okay.”
I responded back, “Wow, sorry,” with a sad emoji.
Waiting impatiently, I got another text saying, “It’s okay, we had her take a shower last night and she’s sleeping it off now.”
Sending a blushing smile emoji, I really hoped she’d be able to keep it a secret and after following up with a text saying, “Keep me posted,” he immediately sent me a thumbs up.
It made me feel that she hadn’t said anything, at least not yet, and as I tried to relax the rest of the day, all I could think about was her.
We’ve seen each other a few times but only casually and we always seem to end up carefully flirting; hoping and wanting to do it again, at least I know I do.