I was, and still am, a strike out with the ladies. I was 22 years old, about to graduate from college and still a virgin. Now, I know that there are actually a number of people who make it that long without having sex, but they usually choose to do that; I had chosen the opposite, but I just didn't seem to be able to act on that choice. For the most part, I think my main failing was just being too shy; I couldn't go up to an attractive girl and say anything, despite being funny and smart with people I knew. I also wasn't all that attractive: 6'4" tall, dark brown hair and eyes, but I was 250 lbs. I wasn't FAT, I was just overweight. Being tall helped. But all the same, girls didn't seem inclined to strike up a conversation with me, and since I couldn't strike one up myself, I was always left to the sidelines.
One day, surfing the net, I came across an online dating site that seemed much more geared towards finding sex than anything else. Seeing as how that's what I was looking for, I decided to join. After quickly realizing that to get any sort of results I would have to pay for the site, I reluctantly pulled out my credit card and did so.
I very quickly came to realize that it wasn't going to be as easy as I had thought. I sent out literally hundreds of e-mails to other members, trying to describe myself and indicate a desire to get to know them, if not outright meet up and fuck. When I realized the only responses I was getting were automated ones directing me to "Come see my web cam" or "I put my contact info here to weed out the freaks" and all of them sending me to other pay sites, I almost decided to drop my membership and continue on my fated course to die a virgin.
Then I found her profile. To be honest, nothing about it stood out from any other. In fact, she didn't even have a picture. She was farther away than I had hoped for, but at this point I was really desperate. I sent off a variant of my usual e-mail and thought nothing more of it. Shortly after that, she "Blew me a kiss." Deciding to be daring, I sent her another e-mail telling her my actual e-mail address and saying that digital gestures were all fine and good, but a real conversation would be better. To my surprise, she sent me an e-mail... and it didn't ask for a credit card. To say I was ecstatic would be a bit over the top. I did have those proverbial butterflies trying to escape from my digestive tract, but in the back of my mind, I couldn't help a little prick of cynicism from whispering, "This isn't going to lead anywhere. Nothing you've done has ever worked. At best, she'll become a friend, just like every other girl you've actually been able to talk to."
With my body and mind betraying me at every step, I meekly soldiered on, replying to her e-mail. Soon we were chatting in an Instant Message. She sent me a picture of herself, and I was doubly sure that nothing would come of it. She was beautiful. She had a set of "chameleon eyes" that change color with mood, long red hair, pale skin, freckles, and a small petite body. An almost perfect example of a fantasy I could have cooked up in bed. No one this attractive would be interested in actually seeing my bulky, hairy body naked, I was sure. I hesitantly sent her a picture of myself. To my surprise, she wasn't turned off at all. In fact, we seemed to be hitting it off quite well. We had similar interests, where we disagreed, we could argue without getting mad. I was having one of the best conversations of my life with a girl I had never met for real. I was flirting, I was listening to her problems, and I was genuinely interested in everything she typed. She seemed just as anxious to meet as I was; even though it was plain our pasts were as different as possible. She wasn't a virgin; she'd lived quite a bit of life. My most adventurous story was about taking a ride from a stranger on a trip out to LA where nothing went wrong at all.
We decided to meet the next day. I had to drive over two hours to get there, and the entire way I was imagining various scenarios; all of them ending worse than the one before it. When I got to the city limits of her town, I called the number she had given me. My God, even her voice was sexy. She gave me directions to her house, and when I got there, she jumped in my car without an apparent second thought. We went out to eat a late breakfast and she gave me a tour of her town. Now I was very nervous. I had never been in a situation like this, and whenever I tried to think of something to do, my mind blanked. I was going to blow it, I just knew it. We decided on going to a movie, but the ones we wanted to see were already started. We decided on what we thought was a horror movie. It turned out to be nothing more than cringe inducing blood and gore. Neither of us was very impressed with it, and I managed to fulfill my own prophecy. Rather than put my arm around her, even when she visibly cringed, I merely sat there, supremely conscious of her leg, her arm, her body next to me.
After the movie, I drove her back to her place, let her out and drove off. I had mixed feelings. I was extremely attracted to her, and she had indicated a desire to do something again, but that voice kept telling me that she had only said that so as to not hurt my feelings. When I got home, she IMed me. The fact that she had initiated another contact had me overjoyed, but what she said caused me to crash. She told me she was disappointed that I hadn't touched her in the movie and that I hadn't lingered when dropping her off. Once again my psyche went to war. Part of me was amazed that, even after seeing me for real, she had wanted me to do those things, the other part slowly driving spikes into me saying I had royally screwed up my big chance, just as I always had.
The next day, we had another great IM conversation, and had another date set to meet. We decided to rent a movie, check into a hotel and just pamper ourselves all day. I know exactly what I was hoping for at the mention of a hotel, but I was still unsure about her desires. I know, some of you reading this are just calling me pathetic, obviously she was interested in going to bed with me. I'd made an art out of assuming that girls didn't like me; so even here, I was imagining reasons to go to a hotel that didn't involve sex. I almost succeeded in convincing myself that those were the only reasons that existed.
We found a hotel in her area that actually had a VCR we could rent, as well as a large whirlpool tub in the bathroom. It was perfect, or so we thought. I drove back to her town on the day we had decided, called her to tell her I was close, and pulled up to her place. After making me wait, she came out and climbed in the car, looking even better than she had the first time, if that was possible. We drove to the hotel before I mentioned that we hadn't rented a movie yet. Dumb move one on my part.
We then spent a lot of time trying to find a place with a selection of VHS as most places had switched to DVD only. When we found one, she informed me that she was really bad a picking out movies, and I was stuck staring at all these movies, wondering what would be appropriate. After a much longer time than deciding on a movie should take, she said she wanted to sit down, so we went back out to my car. Since it was quite cold out, I started the motor to let the heat run. I suggested going back to the theater and seeing if one of the movies we had actually wanted to see was playing. Dumb move number two.
When we got to the theater, we were treated to the obvious fact that theaters don't often have movies playing during the day on a weekday. We pulled out of the parking lot and began to aimlessly drive around. We were talking and having a good conversation, but I was freaking out inside, trying to figure out what to do. Should I suggest just going back to the hotel and making it obvious that I expected to just have sex? Should I let her make the first move? As it turned out, we ended up going to Chicago and having a pretty good time. She had never been to the Sears Tower and it was actually quite an enjoyable drive, our conversation remaining pretty free and easy. By the time we got back to her town, it was again late, we were both tired, and when I dropped her off, she didn't even give me the chance to linger, saying she was really tired. I drove the 2 hours back home, once again mentally kicking myself on one hand, and remembering fondly the great time we had actually had. I kept remembering seeing her in the seat next to mine, sitting beautifully, getting animated when a topic she felt particularly strongly about came up.
When I got home, I decided I absolutely had to take the situation into my own hands... completely out of character. I told her that the next time I would bring a movie, we would get the hotel room, and nothing was going to change our plans. I even called the hotel, reserved a room and rented a movie on a weeklong rental. Within a few short days, I was once again driving toward her town. I was nervous, but excited. If I could just keep up my courage, I knew what was going to happen. I picked her up, drove to the hotel, got the key for the room, and went up. We looked into the bathroom and saw the whirlpool tub. It was huge. It was still short for someone as tall as me, but it was much bigger than I had been expecting.
"This looks fun," she said to me and started the tub. While it was filling, we went out and sat on the bed. I noticed that I had forgotten to rent the VCR, but forced myself not to say anything.
"I'm gonna go get ready," she said to me.
"Okay," I responded, wonder what exactly she meant by 'get ready.'
She went back into the bathroom and closed the door. I sat on the bed, wondering what had happened to make me so lucky, and what could possibly go wrong to bring the universe back into a balance that was on the verge of being tipped forever. That's when the door opened again. She walked out wearing nothing but a towel. I was speechless, she was absolutely beautiful. She came and sat on the bed next to me and we started talking about a lot of trivial nothings, but we started playing with each other's hands. My fingers caressing hers, then hers caressing mine. We lay down, holding each other, our hands still touching. In a bold, for me, move, I brought my other hand up and started rubbing her shoulders. Her skin was so soft. In all of my fantasies, I hadn't imagined it would feel like it did. After quite a while of this, she sat up and looked at me.
"Time for the tub?" She asked it so nonchalantly, like it was the most natural thing to ask.
"Sure," I responded, trying to appear just as nonchalant, but failing miserably. She grabbed my hand and pulled me up. We walked into the bathroom and turned off the water. For a few seconds, we fumbled with the controls, trying to turn the jets on, and then there was nothing left to do. We both straightened up. She turned away from me and dropped the towel. Her ass was just as beautiful as the rest of her. I could see one breast sitting on her chest, the other one on the far side, the nipple already hard. I was actually turning her on, it was a powerful feeling. Quickly, I shucked my clothing and followed her into the tub. We sat next to each other, the easiest formation in the tub. I put my arm around her; she snuggled deep into my side. My hand started rubbing her side; I was just sitting there, marveling in the feeling of a beautiful young woman sitting naked next to me. Very slowly, she moved in front of me, her back toward me.
"How about a back rub?" How could I refuse? I started massaging her back, going all the way from the back of her head down to her exquisite ass. She was really enjoying it. Obviously I was too. After about 10 minutes of this, she leaned back against me. My cock, definitely quite hard, was pressed up against her back. I moved me legs so she was sitting between them, and I put my arms around her. She moved my hands to her breasts. They were soft and full. I rubbed over her nipples and she flinched. Her breasts were very sensitive, and I decided to exploit that. I started pinching her nipples, rolling them between my fingers. She squeezed her eyes shut, but didn't tell me to stop. At times, it looked like it was painful, at other times it looked like she wanted it to be painful.
Almost as a spasm, she arched her back pushed her head higher and pulled my lips to hers. It was at once the most awkward and the most sensual thing I had ever done. She tasted sweet, she felt great, and best of all, she was responding to what my hands were doing. She slid one hand behind her and started rubbing my cock. Again, she moved as if it were the most natural thing to do, and I suppose in that situation it was. I slid one hand down off her breasts, reaching for the last bit of territory I had yet to feel. In our position, it was a bit of a stretch, but I was never happier for my long arms as I was at that moment.
My hand slid down over her shaved slit and parted her lips. It felt warm and kind of spongy. I couldn't be sure, since we were sitting in water, but it certainly felt like her juices were flowing. Once again, we kept ourselves going; this slow exploration of each other's bodies. We lay like that for close to 15 minutes, my hand rubbing her clit, sliding into her pussy, my other hand still pinching and twisting her nipple, our mouths pressed together, sucking on each other's lips, her hand rubbing my cock behind her. I could have stayed there forever, it was so sensual, our entire bodies pressed against each other, the water of the tub allowing us to slide slightly, skin sliding against skin. Then she disengaged from my body, spun herself around and pulled herself up. This was it, the moment I had been waiting for since I was 10, and with the person I had wanted since I first saw her picture.