So this is a true story about the 1st man that I ever met. I was a transfer and had been talking to a much older man on gay phone chat lines. He was about 50 if I remember correctly.
I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not considered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural.
The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?
I had never met anyone before; no one had ever seen me dress before? But I agreed. I then spent the next day trying to think of excuses, ways out of doing this, I was in denial, I told myself I was straight, It was not what I wanted. I tried talking myself into not meeting him. But I couldn’t… something inside me made me do it. I hated myself for it, I was disappointed and disgusted in myself, BUT the self hate made me want it more??? I knew it was wrong. It was too late I had already committed and agreed to this. The man was travelling a long way for me.
On the morning of the meet I remember my heart racing, I was even more terrified and scared. I made my excuses why I would not be going to school and was staying home. I think we met around mid-day so the morning was a rush of getting ready.
I tried not to think about it, I tried to put what could happen to the back of my head. I focused on getting ready. I had the longest shower ever, soaping myself with my mother’s scented potions and washes, I loved that feminine smell. Luckily I didn’t need to shave, as I had not really started growing any body hair. Once showered I raided my mother’s wardrobe, I choose a very short and tight fitting back dress, some black French panties, stockings and suspenders, I used some of mothers perfume and then raided her jewelry and make up! I can’t remember much about what I choose but I know I had very bright red lips, this was a request form the man I met. Sadly her shoes no longer fitted my feet so I had bare stocking clad feet. I had however painted my nails so they were a nice slutty bright red colour.
Once ready I was terrified, I wanted to back out even more, I could feel my heart beating faster and faster. I don’t know what made me go through with it, just something inside me told me this is what I needed.
I had arranged to meet him close to my house in a secluded lay-by. I had not thought his part though, how was I supposed to get there dressed like this? I had no shoes, no wig and very poor clown like make –up! I actually threw on a tracksuit and trainers (sexy I know). I was so nervous on my way, I felt sick, this was not natural, I did not know this man, I had never been with a man before!
It was about a 10 minute walk, but it felt like forever, I was still trying to talk myself into backing out. The feeling of the panties and stockings felt amazing though, I loved the feel.
I arrived early; I am always a little early and had to wait. I hoped he was not going to turn up, and then it would not be my fault it did not happen. I didn’t know what to do with myself. After about 10 minutes a car arrived. I felt like I wanted to wet myself, I was so scared. I had not considered the danger until he was here. What the fuck had I done?
The man got out the car and said hello. He was not what I had imagined, he was rough, he looked older than I imagined. He handed me a plastic bag containing a pair of cheap heels and a bottle of MD20/20.
I cannot really remember the conversation; I just remember drinking and him telling me to dress. I slowly and shyly undressed form my trainers and tracksuit and put on the shoes. I had not walked in heels for a while so I bet I looked stupid. I was ordered into the car so we could find somewhere more secluded.
I sat frozen, not talking and my mid racing. I remember him undoing his jeans as he drove and I immediately without thinking started rubbing his crotch; I was shocked how easily I did it and without being prompted. Soon after I was wanking his semi hard cock as we drove. It felt weird, it did not felt like mine or how I felt it would, it was warm. I just wanted it.
After hat felt like hours, but in reality was minutes we were down a quiet secluded road. He pulled over and we got out of the car.
I don’t remember the conversation but I remember I was soon on my knees, he wanted me to suck his cock. Without thinking or hesitation I did it. I remember thinking “fuck I am sucking a cock!” and I loved it! I loved everything about it, how it made me feel, how feeble and powerless I felt, ow light headed I was from the booze, I loved the taste, the texture. I loved the fat I was making this man moan and his cock grow in my mouth, his pre cum tasted sooo good.
After a few minutes he told me to stop. He wanted to fuck me. By now I would do anything, I loved this! I loved this stranger and old man talking to me like a piece of shit, I loved being dressed this way. I loved what I was doing. I was no longer scared. I was just excited.
While he put on a condom on I was told to bend over the car and pull up my dress. I remember him f***efully pulling my panties down before I could feel him behind me. I had never been fucked before, I had used a vibrator my mother owned and carious other household items so I know of knew what to expect. But it wasn’t like that. It was not a good experience. He did not use lube and although he was not that well endowed he f***ed it inside my ass. My body felt like it was going to split in half, pain shot all the way though my body. I screamed lots. He was stronger than me and didn’t pull out, he didn’t stop. He was pulling me closer by the hips. Pushing himself into me deeper. I tried to escape but couldn’t. After a few minutes of me begging him to stop he did. My head was spinning. I felt sick, I felt in pain but I felt excited.
I was then back on my knees sucking his cock as he wanked it until he came over my mouth and chin and onto my dress. I had tasted my cum before but this was nicer, it as warmer. I loved the feel of it on my skin.
Once he had cum he totally lost interest in me, he just wanted to go, but was kind enough to give me tissues to clean myself up (I was bleeding slightly from my ass) and I quickly dressed again in my tracksuit.
He drove me back to where he picked me up in silence. I could smell sex on myself, my ass was on fire and burning. But I was happy. I was no longer a virgin. This experienced shaped who I am now…
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