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In the early days of chatting online, so many years ago now, I used to chat a lot in various kinds of sexually themed chatrooms. More often than not I chatted under a female screenname. I’ve always had a very strong feminine side and I was good enough to get away with it. Under the various female names I used I chatted with men and women alike. Usually it was just straight up cybersex but on a few occasions I engaged in long erotic role-plays that could go on for weeks.
There was one woman in particular that I really got it on with. We role-played that we were long-distance girlfriends and “the sex” was awesome. After we had chatted for about a month it almost felt like a real relationship and that lead to her wanting to meet for real. Needless to say that was not an option for me since well … my cock was a little too big for me to pull it off without telling her I’d just been pretending to be a girl. I panicked and there was a brief moment when I actually thought about coming clean and hope she still wanted to meet up. In the end I just blocked her from my messenger.
After that incident I decided it would perhaps be better to be up front about being a guy wanting to role-play as a girl. To my surprise there were a lot more people online willing to accept that premise and I even got asked to have phonesex while playing a girl. One of the best phone sessions I had was with a girl who wanted to play a guy to my girl. It was totally hot when she talked about showing her big cock into my tight cunt. We ended up calling each other a few more times before it faded out.
It was also about this time that I started to dress up as a girl when I went online to play, at first just casually, a pair of panties, stuffed bra and maybe stockings too. Then I met this guy who totally bought the concept. We started chatting via messenger and kept a nice long-term online relationship going with me playing his neighbour’s daughter Nicole. Whether she existed for real or not I have no idea bit it quickly evolved into so much more than just sex and slowly I started to build up a whole backstory for myself, partly based on my own life partly made up. I invented boyfriends that I told him about, even the occasional girl I had a crush on. I had issues with mum and dad that I vented to him. It became very intimate even if it was largely fiction.
After this had gone on for about 6 months I had started to build up quite a feminine wardrobe. I had dresses, skirts, blouses. I even had a special drawer for panties, bras and stockings. When I chatted to this guy all dressed up I totally felt like a girl and it was such a ikitelli escort bayan good feeling that he so completely accepted me as a girl without making any veiled suggestions about my cock or anything.
One day as we had just finished a two hour long cybersex session he told me that he’d be passing through the town where I lived on Saturday the week after and wondered if I wanted to meet. That is, whether my female persona would like to meet. I said yes before I had a chance to hesitate.
We exchanged phone numbers and as soon as we said goodbye I went into town to shop. As I said I had managed to build quite a wardrobe but I still hadn’t experimented with makeup yet. I bought bright red lipstick, eyeliner, eyeshadow, blush and a pair of new shiny stockings. I also picked up a short low cut red dress to wear for him.
I spent much of my free time that week practicing putting the makeup on to make it look feminine. Every time I did I dressed up in panties and bra first. Every time I was done I was so horny I had to jerk off several times just to be able to think straight. I felt so sexy and the image in my mirror was so hot when I took on various sexy poses, sticking my ass out while pushing my breasts out, legs straight, looking over my shoulder with my hips pushed to the side, leaning forward pushing my fake tits together … you get the idea. I posed like that for half an hour every night after having put my makeup on.
I had the feminine voice relatively well under control, I had the walk and the posture down and by Friday I felt that the makeup was at least passable. I was nowhere ready for Saturday afternoon but then again I would never have been ready. It was now or never and if I didn’t take this chance I knew I would regret it for the rest of my life. That night I went to bed wearing panties and a bra.
Saturday morning I woke up with an epic erection, vaguely remembering a dream about being a professional gloryhole girl, taking load after load of strange men’s cum in my mouth, on my firm round breasts and deep inside my sopping wet cunt. I used the lingering dream to jerk off to, twice, before I got up and went to take a shower and start preparing myself for the big “date”.
After the shower I put on a bra and panties and had a some coffee and a couple of cigarettes on the balcony. It was a beautiful early summer morning, then I tried to read a bit but I couldn’t focus. I was feeling more and more nervous with each passing minute nervous and time just seemed to stand still. It was like one of those kartal escort bayan dream sequences in movies where everything happens in a sort of blurred slow-motion. To pass the time I started to clean the house. That took a couple of hours especially since I had to stop twice to jerk off.
Finally the clock showed 2:30 pm, an hour and a half left before we had agreed on. I took another shower, slipped into new underwear, a black 36c bra with skimpy thongs to match. Then I sat down in front of the mirror and started putting on my makeup. Little by little brushstroke by brushstroke I transformed myself into a tall, kinda butch girl. Once I was happy with the makeup I put the dress on. It hugged my ass and breasts tightly and really enhanced what I myself felt were my two best features. I waited with the stockings because I didn’t want to risk tearing them before he got a chance to do so.
All dressed and made up I still had 20 minutes to go. I used the time to perfect my walk and my voice, making sure I passed the mirror as often as possible to see myself. I had just stopped in front of the mirror to practice a few sexy poses when the phone rang. It was his number. I answer in my sexiest girly voice. We agreed that when he was outside my door he would first ring once, count to ten, then knock and I would open the door for him. While waiting I put my stockings on and made sure the seams were perfectly straight over my thighs and calves.
Four minutes later there was a ring on the door, then a pause and I counted the seconds, when I reached ten there was a knock. I unlocked the door, straightened the dress, checked myself in the mirror and opened the door for him. He was dressed in a pair of tight fitting jeans, striped shirt and a jacket. He was so handsome and sexy.
His first word was “Wow”. I giggled girlishly and let my eyes drop to his crotch. The bulge looked promising, very promising indeed. I couldn’t resist it. I dropped to my knees and started fumbling with the zipper. I couldn’t get his cock out of his jeans and into my mouth quick enough. I was so horny and the moment I closed my lips around his cock, my bright red lips around his thick veiny cock, I almost came.
I worked my lips up and down that shaft leaving red smears as I bobbed back and forth on it, tickling his balls as I pushed more and more of his cock into my mouth. I could hear him grunting, his hands found the back of my head and he wrapped my hair around them. His hips started to move, thrusting his cock into my mouth, making me gag so that spit kadıköy escort bayan gushed out of my mouth messing up my lipstick even more and making me even hornier.
His grunting got deeper and more intense and I could taste his precum smear against my tongue. Remembering my dream I grabbed the back of his thighs and pushed myself balls deep onto his cock despite my throat protesting. That sent him over the top and he shot a big load of creamy white cum into my mouth, damn near shot it down my throat. I gagged and when I pulled off him it dribbled down my chin and onto my fake breasts. I coughed violently but then I looked up at him with a big happy smile. He smiled back and helped me up.
I lead him into my bedroom and offered him to sit in the chair while I crawled onto the bed, wiggling my ass at him. I turned and put a cigarette into my cum covered mouth, lit it and leaned back against the wall. I pulled up my dress and started to slowly rub myself the way a girl would. I was so aroused that the very touch of my fingers through the thin fabric of my panties was enough to make me cum so hard I almost fainted.
Next thing I knew he was laying me down on my back, lifting my legs up towards my shoulders. I looked up at him barely able to focus my eyes as he pulled my panties aside. He scooped up some of my own cum and used it to lube my ass before leaning over me. When I felt his cock slowly start to open me up I moaned and reached down to spread my cheeks open as wide as possible.
Slowly he began to fuck me, deeper and deeper until I felt his balls slapping against me. He leaned in and kissed my messy lips.
“Fuck me.” I said, “Fuck my tight little cunt hard.”
He grunted and fucked me as requested, deep and hard for a good 10 minutes without pause. In that time I came again and when he pulled out his cock I was a big fuzz of sexual energy.
“Fuck my tits”, I said with a moan and pushed my fake breasts together as an invitation. He smiled and pushed his cock down between my fake breasts. I still had the dress on but by then neither of us cared whether it got ruined or not. He started thrusting back and forth between my fake breasts and it wasn’t long before he blew a second load all over my neck and dress. Gasping for air I reached between my legs and rubbed myself fast and hard and came for the third time within fifteen minutes.
Before he left he used my shower to clean himself up and I ended up giving him another blowjob in the shower. I had taken the dress off but was still in panties, bra and stockings.
Once he had left I stood in front of the mirror for a long time looking at myself. The makeup was a mess, there was barely any lipstick left on my lips and I had cum dripping down my thighs. I looked like a whore and I liked it. I liked it so much that I actually met a few other guys while dressed, except then the premise was that they were paying me for sex and we met at their apartments. The idea of playing a prostitute turned me on so much.
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