Virtual Dating

By Korianne DeLonge

Published on Oct 17, 2008

Transgender

My first summer after high school my parents went on a 4 month trek across the US in a mobile home. It was heaven being 18 and having a whole house to yourself. I didn't have a bunch of parties or anything because I hardly saw any of my friends. They worked day shifts and I was working 4 to midnight. The other reason was that I was using my new privacy to explore my sexuality. I had known I was gay for some time and I had a fetish for dressing in sexy women's lingerie. I had acquired a great collection of sexy panties, stockings and garter belts, as well as a collection of dildos and anal toys. I spent most of my time that I wasn't working exercising, dressing up, masturbating and cruising gay dating sites for older top men.

One day, dressed up in a merry widow and heels at about 11 in the morning, I was checking my email to see if any of the guys I had been flirting with online had written. There was an email there from a website called "virtual date" saying "One of our members has requested you to come and be his virtual date, do you accept?".

It had a spot to get more info so I went and checked it out. You would load in a serious of pictures and the company would generate a virtual character in your image. You would then go on a serious of virtual dates, even going as far as virtual sex! You could load in fantasy scenarios to show your date your desires as they could to you, or you could interact in real time. The eventual outcome was that through virtual exploration you would meet your most suitable partner, knowing each others true desires inside and out. It sounded like a lot of fun so I accepted the invitation.

When I logged on I was getting together some pictures to compile my profile but an email was waiting for me. " Hi Kori, I'm Ray. I'm the guy who invited you out on a date on here. I hope it doesn't make you uncomfortable but I took the liberty of compiling a virtual physical profile for you. I've admired you for a very long time and I even dressed you in my favorite outfit."

I was shocked. How could this guy have compiled my physical profile??? Is there some guy with pictures of me out there? Has he been following me? Spying on me? Has he seen the way I've been spending my summer in the house??

I decided I was being paranoid and decided that the program had probably inserted my name automatically. This is probably just a computer generated guy and they are probably going to start charging me money anytime soon. I decided I'd play it out and see what my virtual guy generated virtual me looked like. I accepted his proposition and then I had to answer a few more questions but still no charge. Next I was ushered into a virtual living room and there I stood, merry widow heels and all! It looked exactly like me, like I did at that very moment!

Then a chat box opened up. "Did I do a good job?"

I was totally freaked out and my hands were shaking. I typed "It doesn't look like me but he/she is very beautiful".

" I think she's the most beautiful sexy thing I've ever seen and I think she looks exactly like you"

I was shocked, winded but so turned on "Who are you?" I wrote.

"Give it some time here Kori, I promise I will tell you but I want to see if you will be my girlfriend. If you don't I'll never bother you again and I'll never tell anyone your secret."

There was another email from the company saying "Ray has sent you a fantasy scenario to view, do you accept?"

I was dizzy at this point but very turned on and very curious. I accepted and the screen went to black.

It faded up on a candlelit bedroom and there I was gently licking up and down a very big thick what looked to be 9 inch cock. It was a very romantic scene with gold satin sheets. Ray, who I was presuming was the owner of that monster, was breathing heavy and whispering words of encouragement in a deep sexy voice. I had my hair flipped over my shoulders and I worked that cock for all I was worth. It was almost identical to the long practice sessions I do with my lifelike 8 inch dildo. The virtual me really went to town on virtual Ray and eventually I wet his cock and gave him and intense handjob, causing him to explode in my waiting mouth.

A window came up "Did you enjoy that Kori?"

I was shivering I was so turned on. I could barely type but I managed a yes.

"I've been dreaming of that for a very long time Kori, I'm glad I finally got to show it to you" Ray typed

"I'm glad you did too Ray, I couldn't tell by the video who you were but you have a very beautiful cock." I wrote fishing.

" I can't wait for you to know who I am. But we need to date a little more. Soon. Will you meet me here tonight after midnight?"

My heart was racing as I typed a yes.

When I got off the site I went straight to bed and began playing out Ray's scenario again with my big lifelike cock dildo. I was just getting into a really good place when my concentration was shattered by a knock at the door. Very confident and insistent. It almost sounded like the police. I decided I would answer it and rushed to get out of my lingerie. The knocking continued so I rushed around and ran to the door scared and annoyed at the same time. It was my parents friend Wayne from two doors up.

"Hi Kori how are you enjoying having the place to yourself?"

"Oh it's great thanks Wayne how are you?"

"Great, hey Kori your dad said I could use his chainsaw if I decided to take down that apple tree in my backyard. Ok with you if I go into the garage and get it?"

"Sure Wayne you can help yourself to anything you need"

He put on a wide grin and said "Anything? Well I'll have to back up the truck then."

I giggled and said " that's ok but you just have to be sure to get it home before my parents get home"

He thanked me and started to head off and said "Oh and if you get lonely you're always welcome to drop by"

"Thanks Wayne, take care"

I was very eager to shuffle him off and get back to my bedroom to finish playing. Wayne was a very handsome older man, and I'd even had fantasies about him doing me before, but I don't think that would be his thing. Anyway I went up to my bedroom, finished off, had a shower and went off to work.

Work went by even slower than usual and all I could think about was that virtual date. I rushed home and logged on to my computer. There was a message from Ray instantly welcoming me home. "Do you need some time to get dressed up?" He asked.

"That would be great" I said "Any requests?"

"How about your school girl outfit?"

"How do you know I have a school girl outfit?"

"Because you would look great in it and I know you like to wear things you look great in"

This made me smile and I went about getting dolled up in my schoolgirl outfit.

When I returned Ray sent me another message "Have you loaded any fantasy scenarios yet?"

"I don't know enough about you to do that yet Ray"

Then a message came up saying "Ray has sent you a fantasy scenario would you like to view it?"

I accepted and the screen went black.

There I was in my schoolgirl outfit kneeling in front of a fireplace with Ray standing in front of me, his cock bobbing in front of my face. I went to work licking up the shaft and tickling the head with my tongue. The I gently sucked his balls while I looked up towards the mystery man's face. He reached down and smacked my bum issuing some direction as he did. I could tell the man had short hair and a beard but that described many men. It looked like he was muscular, hairy and tall. Virtual me knelt on my hands and knees and Ray got behind me and buried his face between my ass cheeks. I was liking it much as I would. I could still only see Ray's muscular smooth back and broad shoulders. I noticed his nice butt too. I could tell by the action on the screen that Ray had his virtual tongue up my virtual ass and I was heading for an orgasm. When virtual me came, virtual Ray caught it in his hand and made me lick my virtual cum off his hand. Then he began to hotdog his cock between my ass cheeks spitting into my ass crack to keep it slippery and smooth. Real me and virtual me were loving it thoroughly. Ray was working his finger in and out of my ass, sometimes breaking to slip it into my mouth and make me suck and get it wet again. Real me had an orgasm. Next thing Ray was holding me by the waist and gently sawing his huge cock in and out, picking up the pace and groaning as I squeeled. Finally he pulled out and had me kneel in front of him and glazed my face with globs of cum. I gleefully licked it up. He caught a big glob on his finger and began gently rubbing it into my lips as I gazed up at him adoringly.

I was floored and turned on. I played all night and hardly got any sleep. I hadn't seen a face, but I did get a really good look at his whole body and if he really looks like that, he's a super stud. I also like the beard. I think that's one of the things I found attractive about Wayne, that and that he's very tall. Come to think of it Wayne's in good shape too. I briefly entertained the fantasy that Ray could be Wayne and then moved on. I knew that who ever Ray was, I wanted to be with him soon. Virtual dates weren't going to do it soon.

I spent all night riding on dildos, cumming touching and lost in sexual bliss. I fantasized about Ray, about Wayne, about Ray and Wayne. I whimpered out my last orgasm at 5:30 am and fell asleep.

Three hours later I was awoken by the sound of the chain saw. I looked out the window and saw Wayne over in his yard working. He looked up and smiled as though he knew I would. He had his shirt off and I knew instantly that he was Ray. I practically collapsed! I pulled the blind and sat on my bed winded. My god that means that Wayne knows all about me. My god that means that Wayne wants to fuck my ass off, cum on my face and do all the things in my video.

I decided to go and load my Wayne fantasy and share it with Ray later that afternoon. It involved my dressed up like a business woman and Wayne dressed up as a biker fucking my over a pool table. Wayne has a pool table and for some reason I've always pictured him bending me over it and fucking me. The part of Wayne would be played by Ray who I am sure is Wayne. I included clues in the scenario to let Ray know I think he's Wayne. If he's not, he won't pick up on them.

I met up with Ray at 2 in the afternoon. I noticed there was no more chainsawing. I proposed he look at my fantasy scenario and he accepted.

It ran and when it was done he sent me a note.

"Tonight when you get done work dress up in your sexy little costume and come over for a game of pool, Love Wayne"

Work took for ever that evening. When it was done I rushed home, cleaned up and dressed up. I was so nervous when I went to Waynes house. The street was quite and no one would have seen me. I knocked lightly and he answered immediately dressed head to toe in leather.

The virtual world never prepared me for the ecstasy that followed, or the adventures this beautiful man and I shared for the remainder of the summer and years beyond.

Next: Chapter 2


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate