A literotic sexstories: Internet Hookup Pioneer by Katie_Johnny ,
The year was 2001. My girlfriend was gone to Virginia to visit her family for a week, and it was just me and the dog staying in the house. We had a big, honking Gateway computer, and our dial-up modem was in full effect. I went by the liquor store on my way home from work, and after walking the dog, I promptly made a drink and got into a bubble bath as soon as I walked inside. I put on an Elvis CD as I stripped down and eased into the overflowing flowery bubbles to relax and leisurely clean myself up.
I had only ever been with one guy at this point in my life. He and I got together one night, and I was forced to reveal that I wear panties to him. I wrote about it in a previous story. We ended up getting together several times after that, and he would buy me panties, bras, nighties, etc, and we would fuck.
To be clear, he would fuck me, I would be the girl for him. It happened for years and while the sex was great, it also lacked in the intimacy department, meaning he would treat me like a fucktoy then act like nothing ever happened after he came.
Earlier in the day, I went home for lunch and self administered a mineral oil enema just in case anything wild went down later that night. I learned this trick from listening to 2 girls having lunch in a casino diner one day, and discussing trying anal for the first time. One girl told the other that her boyfriend told her to do it several hours before he picked her up, and that she had done so, and in return it, “didn’t feel that bad, and actually felt kind of good.”
Before getting in the tub, I followed with a warm water enema to make sure I had the all clear, and I did. I smoked a little bit of herb while in the tub to ease the stress of the day and welcome the weekend with open arms. After washing my hair and exfoliating my body with my girlfriend’s big, fluffy loofah, I grabbed her big pink razor and her pink can of shave cream, and proceeded to shave my underarms and face.
I can remember, “(You’re The) Devil In Disguise” playing, as I stood up and shaved my legs and entire crotch area smooth and clean. As I was finishing, I remember catching a glimpse of myself in the mirror and smiling. In moments like this, if I had to choose between being with girls or my lifelong desire to be a girl, I don’t know what my answer would be.
After covering my entire body in cocoa butter lotion, I proceeded to the bedroom to get dressed and sit down at the makeup table to make myself as pretty as I possibly could. I put on a pink floral satin bra and panty set, and a pink satin babydoll slip. I walked gingerly to the kitchen and fixed another drink, careful not to be seen through the windows by any of our neighbors, then went back to the makeup station.
I wasn’t the best at putting on makeup, but loved the process of applying foundation to smooth out my face as best as possible, then painting my eyes, cheeks, and lips. I have an affinity for pink sparkly lipstick. It really accents my lips well, and makes me feel sexy. After working on my face for about 20 minutes, I stood up and checked myself out in the full length mirror. “Not bad,” I said to myself, before blowing myself a kiss and going into the computer room to surf the web.
Dial up internet really sucked, but no one knew any better at the time, so it was fun and exciting to get online and interact with others. The whole experience was new to me, and to be honest, just sitting on the barstool we had in front of the computer, all dolled up in my slinky nightie and bra and panties was like heaven to me. I smoked cigs at the time, and opened up the windows to smoke inside while I sipped cosmos and looked around. *Side note – When you’re extremely turned on by being and feeling feminine like I am, simply seeing your lipstick prints on the rim of a glass is exciting.
The extent of adult content online at that point (at least to the best of my knowledge) was picture galleries. I would see the occasional video, but it would run really choppy, or take forever to load, etc. I searched online for pics or vids of trans or gay content, when I saw a link for “gay.com” I don’t know why this site ever went away, but it was amazing! Everything was easy to navigate, and you could enter your zip code to be connected immediately in a chat room with everyone in the area. Sure, it wasn’t high-tech, but it was way better than anything out there if you wanted to be interactive with others and feel shit out. If you chose to get one on one with someone, you could, but beyond that, the chat room was wide open and buzzing with tons of people.
After making small talk with a lot of people for about an hour and a half, a guy named Alan and I started hitting it off. He was about 8 years older than me, taller and stockier than me, and knew how to carry on a conversation. When I told him I was into crossdressing, he said that was hot, and when I asked him how he would describe what he wants in a lover, his response almost made me melt in my chair.
“I want someone who is sweet, cute, giving and caring, and who enjoys me taking the lead in the bedroom. I’m dominant, but not in an aggressive way. I just enjoy being the leader, and making my partner feel exhilarated, special, and voluntarily submissive to me because they enjoy the feeling of safety that I provide for them. Also, I love making out, cuddling before and after sex.”
My heart was pounding out of my chest. I could feel it pulsing in my throat and in all extremities. He hit a homerun with is response. When he asked me what I was looking for, I simply replied, “I’m looking to be exactly what you want in a lover, and I can’t wait to show you how good I am at following your lead.”
He sent a smiley face back to me and said, “Can you come over here tonight?”
I felt a rush run over me when he extended an invitation for me to come be with him. I slammed my drink as I rubbed on my crotch and started spreading my ass cheeks through my panties in order to wedge a finger in there. I knew I had to do this, so I told him I would be there in 30 minutes, and that I just wanted to freshen up first.
He replied, “Hey, I think it’s hot that you dress up, but for your own safety and to keep my own sexuality a secret to all of my neighbors, can you bring your girl clothes in a bag?”
This seemed reasonable, so I agreed. I touched up my makeup, took off my babydoll and packed it in a bag, then put on a baggy shirt, a pair of khakis, and a baggy jacket. I fixed another drink for the road, grabbed disc 2 of my Elvis collection, and headed out to see my man.
His apartment building was old, very cool, like it was built in the early 1900’s. My heart started beating faster as I walked up his stairs. I hesitated for a minute, telling myself I could turn around right now and no one would ever know I was here. That’s when I saw him looking through the window at me, smiling and waving. I was there, he saw me, this was happening, and I was excited.
I walked to his door, and he opened it right away, and asked if he could take my bag. He then leaned in and gave me a kiss on the cheek and a nice, welcoming hug. I hugged him back tightly, before he gave me a peck on the top of my head and told me I was welcome to go change in the bathroom if I wanted to. I told him that sounded great, thanked him, and proceeded to go into the powder room to change.
“Would you like a drink?” he asked from across the apartment. “Do you have a preference?”
“A Cosmo would be nice, thank you,” I said, as I pulled out my babydoll nightie and touched up my lipstick. I looked at myself in the mirror, draped in satin, and in full makeup, and gave myself a kiss and a wink before walking out to meet Alan.
He had Marvin Gaye playing on his stereo, and when I walked out, he was standing right there in front of the door in his boxers and sleeveless undershirt, holding my drink.
“Thank you, sweetie,” I said. He came closer to me, handed me the drink, and gave me another strong hug. He kissed my cheek again, and ushered me to the living room, holding my hand.
“Have a seat on the couch, baby,” he said to me, as he was closing the blinds and lighting candles. He asked if I minded that he smoked, and I told him I was glad that he smoked, because I would love one as well. He grabbed an ashtray, gave me one of his Camel Lights, and lit it for me, before sitting down next to me.
Apart from one guy back home that I used to mess around with, I was very inexperienced in being with men. When I hooked up with my buddy back home, it was always done very late at night, typically in silence, and never felt like anything beyond straight up sex. This felt like a legitimate date, not just a meet up to fuck, and that turned me on a lot. Being treated like a woman outside of the bedroom was something I had never experienced, and I loved it.
As we sat there having a drink and smoke, in a sparsely candlelit room, while the sweet soothing sounds of Marvin were playing softly in the background had both a calming and aphrodisiac effect on me. He fondled my neck and shoulder gently with his hand, and started asking me questions. He asked me things like, if I was out of the closet, when I started experimenting with women’s clothes and if I had been with a lot of people. I told him that not only was I not out of the closet, but I also had a girlfriend, and that I had been drawn to women’s clothes for roughly my whole life, then told him that I had only ever been with one other guy in my life.
“That’s fascinating!” he said, as he moved in closer to me and started massaging my neck a little stronger than he had previously been doing. It felt so comforting and soothing to me. He continued, “So you’re telling me that this is only the second experience with a man you’ve ever had?”
Leave a Reply