It was very difficult for my father and me when my mother left us when I was only twelve years old. She was very beautiful and sexy looking, and probably still is. It turned out that she's a real slut and cared more about finding a lot of different cocks to fuck than she cared about us. Dad does his best and makes many sacrifices to be the best parent he can.
My name is Ashlee, and I’m now sixteen years old and Dad is forty. We live in a comfortable condominium in the Little Rock area. Dad works long hours, so I am sometimes home alone in the evenings, and even on Saturdays.
I don’t mean to brag, but I am a very pretty, five feet six inches tall and one hundred and fifteen pound brunette with blue eyes and a great body. I guess I got my looks from my mother. I was kind of plain looking until the summer before my junior year in high school when I turned sixteen. But all suddenly I matured. My tits are a full and round D-cup and I have a gorgeous heart-shaped ass with prominent cheeks. It's fun to see all the boys, and even many of my teachers and other adults, including women, staring at me wherever I go.
Dad has always been a little shy when dealing with women’s issues. Although he did approve me getting birth control pills after I turned sixteen. He certainly isn’t endorsing me having sex. He agreed that it was better to be safe given how crazy the high school years can be. He followed the lead of my best friend, Emily’s, mother in most of those types of decisions. The only problem is that I stopped taking the pills because they made me gain weight. I wasn’t sexually active yet anyway.
Emily is seventeen and she is very pretty and has a great body, just about like mine. I’ve never had sex, but recently used one of Emily’s dildos to get myself off and busted my hymen. Emily was already fucking several of the boys from our school, and even a couple of the husbands of her neighbors. Emily’s lust for older men must have rubbed off on me, because I also found them attractive. She has always been the wild one and pushing boundaries. That’s how the events of this story started.
We slept over at each other’s homes pretty often. One Friday night at Emily’s home she showed me a website she had been going to. It's a site geared for older men to chat and hookup with legal-aged high school girls. She was showing me how much fun it is to chat with horny, older men. She had never met up with anyone from the site yet, as far as I know. I knew that it was only a matter of time since she is always so horny.
When I got home from Emily’s on Saturday, I went onto that same site and setup my profile. I used the screen name Amy and my location as Memphis, which is a little over two hours from Little Rock. I just wanted to be anonymous since I wasn’t sure what to expect from the men who used that site. Then I attached to my profile, a few revealing pictures that Emily took of me.
None of the photos are completely nude or showed my face, but I do have some in my thong underwear and a skimpy bra. Some others that Emily suggested were supposed to get the older men excited. One that she insisted on was from the rear in my thong and bending over. You can see my thick, hairy labia parted by the thong, all framed by my shapely ass.
I started going onto the site every chance I got, even on school nights. I was very popular with the men. I got dozens of messages from the men who said they just loved my pictures. Most of them were just plain rude and gross though. I went to many of their profiles and they're either way too old for me, with graphic pictures of hard cocks and cum, or they would start a message by saying how badly they wanted to fuck me and fill me with their cum.
My purpose of going on that site was to have a little sexual fantasy fun. I didn’t like how forward and pushy a lot of those men could be. One night things changed for the better. Soon after I signed in, a chat window opened from a man named Frank located in Little Rock who said he's forty years old. His profile pictures are very tasteful, and he was wearing shorts with an unbuttoned casual shirt showing his bare chest, but no face photos.
His first message to me was, “Hello, pretty little lady. You're a truly beautiful girl. Would you mind chatting with an older man?”
Finally, I had been approached by a nice-looking man, as far as I could tell. He was very polite, especially when compared to the other horny men on the site. I replied, “Sure, Frank, I’d love to talk with you.”
Then he surprised me when he asked, “If you don’t mind me asking, what’s a beautiful, young girl like you doing on this site with a bunch of horny older men? Aren’t you worried about someone taking advantage of you on here?”
That was getting interesting. He was actually being protective of me, and I thought that he must be a nice guy. Then I messaged, “Frank, I’ll tell you why I’m here if you first tell me first why you’re on here. Aren’t you on this site to find a sixteen-year-old high school girl to meet and have sex with?”
He responded, “I just found this site a few days ago while I was surfing the net and it caught my attention. I’ve been divorced for several years and I’m now living alone. I have a daughter who is about your age. She moved to North Carolina with her mother. I miss her a lot and I’m just curious why a pretty girl like you would be on a site like this."
I was very impressed with his candor and felt some compassion for him being away from his daughter. So, I replied, “Wow, Frank, that’s really sad. My mother also left my father and me several years ago. She's such a slut that I'm living with Dad.”
I did feel bad for him and wanted to compliment him to help him feel a little better. So, I continued, “You're the first man who has contacted me who hasn’t been nasty and rude. I think it’s okay to talk about sex after we get to know one another a little. But many of the older men are just interested in getting between my legs, "into my sweet, young cunt", as some of them say, with no conversation or anything.”
Then he messaged, “Well, I really do think you're a lovely lady. The similarities of our situations are interesting to me. But I also must be honest and admit that your photos are very arousing. You are very luscious to be only sixteen years old. Given the chance I know that I would really enjoy having sex with you. There's a girl living right across the way from me in my condominium complex who has a body just about like yours, at least as far as I can tell in her bathing suit. I’ve seen her down by the pool many times but have never spoken with her.”
I was a little bit curious about the girl in his condo and asked, “Frank, I know that most people try to be anonymous on these types of sites. But if you don’t mind me asking, what is that girl’s name?”
His response didn’t come back immediately because he was probably deciding whether he should risk using her real name, but then he replied, “Her name is Ashlee and I think she turned sixteen about five months ago. Why do you ask?”
I sat in my chair stunned. Was it possible that I had been unknowingly contacted by my neighbor? Our situations sounded very similar, and he was spelling my name as Ashlee, which isn’t the most common version. So before responding I went back to Frank’s profile to see if I could find any clues.
I looked carefully at his pictures and got the answer I was seeking. My condo is on the second floor and many of the units have windows facing other units. My bedroom window overlooks a small walkway and the units on the other side are only about ten feet away. In the background of Frank’s pictures, I saw through his window to the other side of the walkway. I recognized my window from the large decal of my high school logo that's in my window.
I had seen a neighbor down at the pool who looks a lot like the photos I saw online. I think someone said his name is Frank. He is handsome and in great shape. I’ve seen him in his bathing suit and his body looks a lot like the one in the internet pictures. Holy shit! I was likely chatting with my neighbor. He had no idea he was talking about sex with the girl he saw at the pool, and who lives right across the walkway from him!
After regaining my composure for a few minutes, I was able to respond. I answered, “I only asked her name since you mentioned her, and I was curious. Ashlee is a very pretty name.”
I knew that I had to remain anonymous, but I wanted further proof that I was talking with the Frank that I saw at the pool. I continued, “I know that a lot of people don’t use their real names on here. I’m curious about whether your real name is Frank.”
Then he replied, “I’m glad you’re still online. I was worried that you might have left the conversation since it took you a little while to answer. Since you show that you live in Memphis and would most likely never know me, I don’t mind telling you that my real name is Frank. May I assume that your real name is Amy?”
I obviously had to lie about my name and think all of it through. So I said, “Yes, my real name is Amy. I need to go for now and do some homework. I have really enjoyed talking with you, Frank, and hope that I can find you online tomorrow night. You seem like a very nice man. I’d like to get to know you better.”
Then he replied, “I have enjoyed talking with you too, Amy, and hope to talk with you again soon.”
I immediately went to bed but couldn’t go to sleep for hours. I had to think about all that had happened and decide whether I should continue chatting anonymously with Frank like that. I knew that he thought I was sexy and he was thinking about having sex with me. Even so, I had to clarify my desires for him. I woke up the next morning excited about the possibility of having my first sexual experience with my neighbor. I could think of nothing else all day at school.
After school Emily came over to my home and I told her all about accidently chatting with my neighbor on that site. She was excited for me since she had seen Frank by the pool and always thought that he's hot. She helped me take some more pictures, but that time completely nude. Those photos showed my big tits, hairy pussy and nice ass. We even took a couple of extreme close-ups of my pussy when my labia are puffy and juicy. Then we added those photos to my profile. I could hardly wait to talk to Frank again that night.
After dinner I did my homework and then logged onto the site. I had dozens of messages from men who just loved my new pictures. All of them were telling me how much they wanted to suck my pussy and tits and fuck me. Then around 9:30 p.m. I noticed that Frank had logged in. I opened a chat window saying, “Hi, Frank. You might want to look at my new photos. Maybe you’ll want to post some new photos of yourself too.”
It took several minutes to get a reply, and then he responded, “Damn, girl, you're really putting it all out there. You are simply gorgeous and so yummy looking. I could just eat you up, and especially your juicy pussy. What a luscious body you have for being only sixteen years old! Just give me a few minutes and I’ll post a few more pictures of myself.”
I dimmed my bedroom lights and looked across the walkway to Frank’s window. He had his curtains partially drawn and I couldn’t see all the way into his room where he was likely at his computer. But I did see several flashes of light that meant that he was taking some new photos for me.
It only took another few minutes until his next message saying, “Okay, Amy, you can check my profile now. I hope enjoy my new pictures.”
I went to his profile and those new pictures made my pussy wet immediately. The first picture was of his soft, uncircumcised cock which appeared to be very thick and over six inches long. It also showed his large balls hanging down past his soft cock. Then there were a series of other pictures of him getting hard, with the final one showing what must have been a nine-inch-long and very thick cock. Then there were also a couple close-ups of his cock head and balls.
His cock never looked that big down at the pool and I was impressed. I looked at the photos for a few more moments and then responded, “Damn, Frank, what a gorgeous cock and balls you have. It would make any woman happy to be fucked with that monster.”
Then I thought I’d step it up a little and said, “Too bad we don’t live closer. I’d really like to feel that thing in me.”
He replied, “Seeing your pictures and hearing you talk like that makes me want to suck your tasty pussy and tits and fuck you for hours. I know that we’re only about two hours apart, but it would still be hard to meet up with our different schedules.”
I thought about his comments for a few minutes and then I had a great idea. It would be exciting if I could entice him to fuck me in his condo, with a little encouragement from my online Amy persona. I replied, “No, it wouldn’t be easy for us to get together. Maybe I can help you in another way. I could give you some advice on how to find out if your neighbor, Ashlee, would be interested in fucking you. Would you like me to help you fuck her, Frank?”
It took him a few minutes to respond, and I guess he must have been struggling with the ramifications of approaching me, his neighbor, for sex. Then he replied, “I have been thinking about having sex with Ashlee, but didn’t have the courage to pursue it. You've gotten me very excited about it now and make it seem like this could really happen. So yes, I would like your help in fucking Ashlee.”
I was so happy hearing him say that he wanted to fuck me. It was all I could do not to call to him out of my window and invite myself over to fuck him. I also knew that it would be much more enjoyable to somehow seduce him into giving me my first cock. Then I replied, “Oh wonderful, this will be fun. I just wish it was me getting that nice cock of yours.”
I thought for a moment and continued, “The first thing we need to do is make you seem more approachable. My guess is that you're very shy around Ashlee when you see her by the pool. I think you said that you have never talked with her. Try to go down by the pool a lot and engage her in conversation. I know that it can be scary for a grown man to approach a teenager that way. Who knows? She just might be receptive to you. And maybe wear a tighter bathing suit than you usually do, to give her a hint of your big cock. Give it a try and see if she warms up to you. Then let me know how it’s going.”
I went down to the pool on Saturday, wearing one of my normal bikinis. Frank was there and was wearing a tight bathing suit that showed his big cock bulge. I could hardly wait to see if he would approach me. Nothing happened at first. Then at lunchtime I went up to the concession stand to get a sandwich and a drink. Frank followed me up there and also ordered some lunch.
While we were waiting, he looked over at me and said, “Hi, my name is Frank. I think one of the life guards told me that your name is Ashlee. I’ve seen you down here many times with your friend and just thought I’d introduce myself.”
It was so exciting to me that he was following my advice and I liked his approach. I wanted to encourage him further, so I said, “Hi, Frank, it’s nice to meet you. I’ve noticed you down here many times too and you’re always alone. My friend, Emily, couldn’t come today so you can join me for lunch if you want to.”
Frank replied, “Thank you, Ashlee. It does get awfully boring sometimes. You seem like such a nice young lady and I would enjoy sitting with you.”
We sat at a table together and talked about our family situations and life in the condominiums. He knew that my bedroom is right across the walkway from his. But we usually have our curtains closed and we never saw one another. I made it a point to glance down at his cock bulge when it wasn’t real obvious, but I knew he saw me. He was also checking out my body. Sometimes I would stretch or shift in my chair in different ways, so he could see the curve of my ass and my big tits jiggle and sway.
We had a good time talking and I didn’t make it seem like I was anxious to get away from him. After a couple of hours, I had to get back home, so I said, “I’ve really enjoyed meeting you and talking with you, Frank. I hope to see you down here tomorrow.”
Frank replied, “Yes, Ashlee, this has been a most pleasant day. I look forward to seeing you tomorrow as well.”
Meeting Frank had gone much better than I could have hoped. He is just as nice in person as he is on that website. His cock looks so big and I think I saw him getting a little hard a few times. I was looking forward to seeing him again and talking with him.
I saw him down by the pool on Sunday and he wasn’t the least bit shy. He walked right up to me, assuming that I would want his company. I wore a very skimpy bikini that day. The bottom is little more than a thong and the top barely covers my large, brown areolae and nipples. His eyes were almost bulging out of his head from watching me when he thought I wasn’t looking.