Online Encounters

I've been reading Literotica for a long while and this is my first attempt at a story. Some stories might completely true, completely false, or a little of both. Hopefully they are enjoyable. Feel free to let me know what you think.

I've always been a very kinky guy and love showing off my body in silk g-strings, leather thongs, etc. Spending a lot of time online with my business I would break away from the monotony on a webcam site watching, showing, and chatting. From time to time I would record myself and my naughty acts and save them in a inconspicuous file for later use. You can still find me there to this day. One night I got a PM from female saying she was from the my area and made a few remarks about my cock size and how she would love to wrap her lips around it. We had a brief conversation then she said she had to go but would find me later. I thought it was pretty cool to have run into a local female on the site since in the two years I've been on it only as few have been from my area.

Several days went by and no sign of my new chat friend so I began to think I wouldn't hear from her again. Finally one day during the afternoon a PM pops up with NaughtyGurl's name. I was in my usual attire for the site a pair of silk g-string underwear and the cam pointed at my package since I rarely show my face on the site. She told me how sexy I looked and how she would love to be sitting in my lap with no panties on rubbing her bald wet pussy lips all over my silk covered cock. This of course got a nice reaction from me as my cock started growing and becoming impossible to hide in my tiny underwear. She told me how she laid in bed the night after we talked and fucked herself silly with her favorite dildo thinking about me and making herself come five times until she was so exhausted she fell asleep and woke up the next morning with it still inside her.

She asked me to pull out my cock and stroke it for her so I did. She told me to get some lube, grease it up, squeeze it real tight as I stroked it, and think about sliding it into her tight ass. She told me she had never been fucked in the ass but she was so hot for me she would let me do anything. I was falling for this girl quickly and it was easily shown as I shot cum all over my body. This time it was me that had to end our conversation early. I told her I had to be at work shortly but would love to see her gain soon. She replied back with a "You will" and poof gone once again. After she left I realized I don't know this girls name, age or anything else about her for that matter so I checked her profile to find nothing there. I jumped in the shower jacked off once again thinking about my new online playmate and got ready for work.

I have a son from a short relationship who is my world. From time to time the neighbors girl one of four girls would watch him when he was in town and I had to work for extra cash at night. Alyssa was 18 the youngest of the four girls and seemed to be the bookworm type so she didn't go out much on the weekends anyway. The others were party girls from what I could tell with the backyard functions they had. From time to time I would catch one or two of them sunbathing in the backyard by themselves or with friends by the pool and they all had very nice bodies. On many occasions I would jack off while watching them take in the rays. Alyssa had the best figure of the bunch by far and was usually in the majority of my fantasies. Anyway she showed up and I was off to work.

When I got home that night my son was already asleep and Alyssa was on my computer chatting with a friend. I paid her and told her I would need her again tomorrow night if possible. She smiled and told me sure. I hoped in the shower and thought about what it would be like to have Alyssa in the shower with me bent over with her ass facing me, hot water pouring down her body and me burying my face between her sweet young thighs. I toweled off, wrapped the towel around my waste and walk out hoping Alysaa would still be there chatting with her friend but no luck.

The computer was still on so I logged into the cam site jumped in my favorite chat room and there was my new friend. I sent her a message to let her know I was online. She sent my a smiley and said she has been thinking about me. I told her I have been doing a lot of thinking about her since our chat. I told her I would love to know more about her. She told me she would tell me anything I wanted to know as long as I did the same. I agreed.

First was her age, "18" she says, this threw me for a loop as I was 29 and I told her this. She said she loves older men and asked If I had any problems with younger women. After thinking about the hot young thing in my house earlier I replied back with a "No, no problems at all." I asked her if she had a cam or picture online she said she didn't but gave me her description. 5'2, 115, long dirty blonde hair, 34d breasts, nice ass (so she's told), and pouty lips, and tan. I pictured all of this and responded back with a "Very nice." Thanks was hers.

She told me she had been thinking about me all night and wanted me to turn on my cam get on my silk g-strings so she could finger her clean shaved pussy while watching me. I had no problems with that. She told me what she was wearing, a pair of silk g-strings and a t-shirt. Then she began to tell me about how she loved walking around the house in them driving he father up the wall. She got a thrill out of it and he would always tell her to go put some clothes on. She would act all innocent, walk over, kiss him on the cheek, and walk away knowing he watched her ass and every move it made as she did. I told her she was a naughty girl, she said "More than you could imagine." She said she was so hot thinking about it she was going to go get something to drink and tease him some more. I laughed, she said she would brb.

She came back and said she had her dildo out and was taking a ice cube and rubbing it on her clit. She asked me if I have ever been with a girl 11 years my junior I told her no but think about the neighbor girls all the time. She seemed interested in this and wanted more details. I told her about them all and how Alyssa watched my son when I worked. She asked me if I ever tried anything with her and I told her no but wished she would have been there when I walked out of the bathroom tonight with just a towel. I explained to her how nothing would ever happen because she didn't seem the type. She told me if we met she would seduce her and get her to sleep with both of us. I thought great she's bi also! We both got ourselves off and decided to meet in the near future and said our goodbye's. Once again I forgot something. I don't know her real name.

I didn't see her online during the day the next day. Alyssa came over wearing skin tight almost see through white shorts and a white tank top which showed off her breast very well. It appeared she wasn't wearing a bra because I could make out her nipple color or panties because there were no lines. I couldn't help but stare and I complemented her on her figure. She thanked me and I was off to work. As I drove to work I thought about how my life would be complete to have my new found friend and Alyssa as my lovers.

I got home from work and once again my son was in bed and Alssa on the computer. It was getting late so I gave her the cash she gave me a hug bye which I thought was weird but instantly gave me an erection that I had to hide as she walked out. My regular routine of jumping in the shower changed instead I jumped online. A couple minutes later NaughtyGurl came online and we said our hello's. She told me she had been thinking of me all night a day and she wanted me right now. I told her it wasn't possible until my son went back to his mothers in a couple of days. She sent a sad face, I said sorry, and told her I needed to jump in the shower. She said ok and I did.

I got out of the shower threw on my favorite silk g-strings and walked into my office sat down to find she had gone offline. I was disappointed but figured she would be back on. I heard something in the house and figured it was my son waking up so I threw on some shorts and went to check on him. I walked into the living room to find Alyssa standing there. I asked her if she forgot something, she said no. Confused I asked her what she was doing here and she said "I told you I wanted you right now and I always get what I want." My mouth dropped open she gave a sexy little smile, walked over, reached into my shorts, planted her lips on me and slid her tongue into my mouth before I could say anything.

She dropped to her knees, dropped my shorts to the floor, pulled out my cock, ran her tongue over the tip, looked up at me and said "I've wanted to do this for a long time. I found the saved movies of yourself awhile back and masturbate to them every time I'm over here. I even emailed a couple of my favorites to myself so I can watch them at home." She told me she just figured out what site I frequented a month or so ago and has been building up the never to do all of this since. Then proceeded to give me the best blow job I've ever had. While giving me head she fingered my ass which sent me over the hill quickly blowing my load and she swallowed every last drop.

We moved into my room where she walked over to the computer, turned on the camera, hit the record button, and told me she wants to have her "first time" recorded. She walked over to the bed peeling off what little clothing she had on, laid down on her back, and said "Come and take the cherry I've been saving for you for years." Although she had no cherry to take it was the thought that counts. I looked down at this young goddess smiled and told her that will come shortly. First I wanted to bury my face between her thighs and smother myself with her sweet juices. And sweet they were. I lost count how many times she came while I slid my tongue in and out of her tight love hole and fingering her ass at the same time.

Eventually she begged for me to take her virginity and I obliged. She had the tightest pussy I have ever had wrapped around the head of my cock. I'm a decently sized guy and wondered if I was hurting her as I slid in and out of her tight pussy. I asked and she told me "No, now fuck the hell out of me big boy." So I did. We screwed like animals an uncountable number of times that night. Just before daylight she said she had to get home before someone noticed she wasn't there. Before she left she asked me if I had any regrets in what we have done. I told her no except the fact that I wouldn't be having two gorgeous young ladies in my bed. She laughed kissed me on the cheek and said, "I have plenty of friends." But that's another story. :)