Internet Hookup Pioneer
By Katie Johnny

Posted With Permission from Katie Johnny

Part 1

This is the true story of the first time I talked to someone online, and actually followed through with going over to his house to serve him and make love.

The year was 2004. 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 day on accident. In other words, he caught me being slutty while jerking off and I was forced to reveal that I wear panties to him. We ended up getting together several times after that, and for several years. 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, but it really lacked in the intimacy department, meaning he would treat me like a fucktoy then act like nothing ever happened after he came, but I digress. Back to the story.

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 onmy 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 his 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 ownsexuality 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 ofthe 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?”

I replied, “I’m telling you that this is the only other experience I’ve ever had with another man in my life, and so far, you’re way more romantic than he ever was.”

He said, “I know I told you that I was dominant on the message board, and I am, but that only means that I like to provide comfort, pleasure, and strength to the people I hook up with. I’ve hooked up with a lot of girls, but I haven’t hooked up with many more guys than you have, to be honest. I’ve never hooked up with a crossdresser in my life. I always thought they were sexy, but just never had the chance, I guess. What got you into crossdressing to begin with?”

I didn’t really know how to answer that question. I mean, it’s obvious that women’s clothes are so much better than men’s clothes, but for me, it went beyond the luxurious fabrics and cute dresses. I answered as best I could.

“Well, I wish it were as simple as enjoying dressing up, but it isn’t, really.”

I nervously finished my drink, so he got up to get me another one, and asked me to continue talking.

“I guess I’ve always quietly felt like some kind of genetic mistake was made when I was being put together in the womb. Growing up, I always felt like I was different on the outside from how the entire rest of my being felt on the inside. Sure, the clothes were arousing to me as a younger person, because I knew what I was doing was considered taboo, but honestly, the only times I really ever felt like I was ever being honest with myself were when I was dressed up and being a girl.”

He came back in with my drink, and noticed I was visibly anxious and vulnerable from talking honestly with him. He acted quickly.

“Relax, baby,” he said, “you’re safe with me. Nothing can hurt you. Understand?”

He handed me the drink and moved in closer to me again when he sat down. Our knees were touching, and he put his arm around my nervously shaking shoulders, pulling me in closer to his body. I took a big sip of my Cosmo, then set it on the table, and put my head on his shoulders. This felt really good and very normal. His presence had a calming effect on me. I continued,

“So, for me, it’s not just a fetish, it’s my desperate attempt to claim some of the real me away from what society deems who and what is or isn’t male or female. Does that make sense to you at all? Or is it TMI?”

He snickered when I said that, kissed the top of my head, and said, “If I’m being totally honest, I don’t fully understand someone being confused about their gender, but I totally respect it, and find your earnest desire to be a woman fascinating, and I think it’s totally hot.”

As my head rested on his chiseled shoulder, I glanced down his entire body with my eyes, and saw his cock was very hard, and that his boxers could barely contain it. I sighed longingly, and he subtly laughed under his breath, then made his cock jump around in his boxers, telling me that it was saying hello to me, which made us both laugh, and he gently pulled me in tighter and closer to him.

He was running his hand up and down my back, and sticking it between my babydoll nightie and bra, running it all the way down to the waistband of my panties, and gently drifting his fingers down to the top of my ass crack. It was so arousing that I was breathing heavier with each rub he gave me.

“I know this much: I want you to feel comfortable and safe with me,” he said in a low tone, practically a whisper.

I replied, “I do, baby. I’m nervous, but in a good way. I don’t know if it’s possible that I could feel any better than I do right now.”

He replied, “I’m willing to bet that you could feel better, and that you will feel better soon.”

That really turned me on, and I turned my head into his chest, giving a soft, wet kiss to his moderately hairy pecs, which made his breathing intensify.

“Would you mind if I kissed you?” he said to me, as he gripped my shoulders tightly.

I replied, “I thought you would never ask,” and smiled at him as I moved my lips closer to his, where we locked our mouths together in unison.

He was a tremendous kisser, gentle but forceful, with lots of tongue, but he knew how to use it. We were both breathing heavy as we made out uninhibited. I don’t know what came over me, but instinctually I fully turned my body and straddled him, with my legs spread, and resting my silky ass right on his throbbing cock.

The kissing became more intense, and I naturally started grinding up and down on his crotch. He lifted up my babydoll and grabbed two full hands of my ass cheeks as we were slobbering all over each other’s faces. It was at that moment that he sweetly, but forcefully slapped my ass through my panties. I gasped organically, and was as turned on as I’ve ever been in my life, then let out an approving whimper as we kept making out, and it prompted him to do it again, which made me whimper in ecstasy again.

“Shall we take this to the bedroom?” he asked, as we kept on kissing and grinding on each other.I smiled at him in between kisses, and again said, “I thought you would never ask.”

He laughed, and slapped my ass again before saying, “Go make yourself comfortable in my bed, sweetie. There are toys and party favors on the nightstand. I’m going to refresh our drinks, make sure the door is locked, and use the bathroom.”

I grabbed my bag out of the bathroom to get my lipstick, and walked like a giddy sissy girl to his bedroom. He had candles lit on the bannister and on the window sills, and soft, sweet soul music playing at a low volume on the stereo in his room. Daddy had game.

I looked in the mirror and applied more sparkly pink lip gloss to my pouty lips before getting into his bed. I laid down on top the sheets, and wriggled around, trying to find the perfect pose for him to see as he entered the room. I glanced over at his nightstand, and saw rubbers, cherry flavored lube, and a fresh bottle of poppers. Yeah, like I said, daddy had game.

I stacked two pillows on top of one another and laid back on them. I spread my legs, took 2 fingertip sized dollops of lube, and made my way down to my sissy pussy to get it nice and wet. I pulled my panties to the side, and slowly massaged each finger into my hole, getting it nice and moist. My pussy was being really sensitive and responsive to my toying with it. I worked two entire fingers into it, and was running them around the interior of my pussy when he walked in.

He had his muscle shirt on, no underwear, and his cock was extremely hard. As he got closer I noticed that he had a cock ring on, and that was making him bulge out even more than he normally would. What can I say? It turned me on. I started to get up from where I was so that I could kiss him again, when he told me to lay back down. I did as I was told.

He got up on the bed, and crawled with his knees to get on top of me. I was breathing heavy, very excitedly. He kissed me deep and long, and I wrapped my arms around him, rubbing his strong shoulders as we briefly made out. He pulled my nightie up and started slowly kissing me all the way down my body. Once he passed my tits, he put his hands on them and began sweetly squeezing and rubbing them through my bra as he descended between my legs with his head.

I could feel him breathing heavier as he put his mouth on the front panel of my panties, and kissed my cock through the fabric, before going further down. He pulled my panties to the side and immediately stuck his tongue into my pussy. I couldn’t believe how fucking amazing it felt to have a man lapping at my sissy pussy. I naturally spread my legs even further, as he started spreading my ass cheeks open with his hands, and French kissing my quivering sissy cunt.

I was squirming in pleasure the entire time, which felt like forever, but in reality was only 3 or 4 minutes. He stopped abruptly, and quickly scurried his way back up my body, then started kissing me aggressively. We were both breathing heavy, I had my arms around him again, and was holding him as close to me as I could when he pulled up from me.

He scooted on his knees over to his nightstand, with his engorged cock at eye level with me. He took a sniff of poppers, and then offered me a sniff, which I also took. He told me to hold it as long as I could, and as soon as I exhaled, he told me to take 2 more and hold it as long as I could,which I did. This was my first experience with poppers in a sexual situation. I remember sniffing them in high school with friends. We thought it was just a head rush followed by a headache. My head was spinning, I felt every inch of my body tingling, and no sooner than I exhaled, he put his cock on my sparkling pink lips and plopped it into my mouth.

As the waves of synthetic euphoria rushed over my body, I began fucking his cock with my mouth. I was breathing through my nose, and had his entire throbbing rod all the way down my throat, and his balls were bumping into my chin.

“You look so sexy,” he said, gently thrusting his cock in and out of my sparkly lips. “You’re so good to me, you make me feel so good, baby.”

...continued in Part 2