A Cross-dresser’s Fantasy

Hello everyone, I’m a regular reader of the site and figured that it’s about time that I write a story. Let me first say that the story is completely fictional.

Let me first give you a description of myself. I’m really petite and have an average ass. I’m 21 years of age and weigh about 50kg. If my face and chest weren’t visible, one could easily mistake me for a girl of 18-20. I’ve a light brown complexion and a darker ass. And my cock is about 6 and a half inches.

Going back a few years, I got in to cross-dressing as a means to satisfy my own sexual needs. I would role-play as a hooker or a maid and feel aroused. This was temporary and I had forgotten all about it, till I moved to my own apartment last year. While browsing the internet, I found the old urge rising up and I couldn’t stop myself. I went out and bought a few clothing, namely, two sarees, a few blouses, skirts, bras, panties …etc. I didn’t buy everything together. Bought each item from different stores at different time.

Anyway, I would dress up for people on cam and used to feel hot when people would ejaculate seeing me. I wanted to have sex physically with a guy but I was too afraid. But all was about to change.

Two months ago, I had to travel to another town, and I was travelling by a private bus. It was late, about 10:30 pm. I had a few hours of journey left and the bust was practically empty with a couple sitting in the front row and me sitting near the middle. The bus made a regular stop at a bus stand and two people boarded. A guy about the age of 19, who sat toward the front of the bus. The second guy was an elderly man, wearing a dhoti. He was bald, round and big.

He probably weighed around 85-90Kg and had a pot tummy, which I should say, is not the best way to describe it. One can just call him fat. His face looked fresh and fair. With a thick mustache. He had a gold chain around his neck. He wore what seemed to be an expensive shirt and had the fragrance of the perfume he used still on him. He came and sat next to me, which I found a little weird because there were so many empty seats. But I didn’t care about him and pretended as if I am asleep because I did not want to have any kind of conversation.

A few mins later, I felt his hand really close to the underside of my thighs. I was worried if someone would see, but at the same time, a bit aroused. I pretended to be asleep and decided to see what was going to happen. After a few more minutes, I felt his hand really under my thighs and trying to move towards my ass. I opened my eyes to find him retract his hands as fast as he could. I looked at him for a bit and then smiled, hoping that he would realize that I liked it. And yes he did realize that and he soon put his hand under my ass and started to massage it. But it was risky, since the bus conductor was constantly moving from one end to another. Finally, when we reached the bus stand, he asked me to give him my phone number, which i obliged. He said he would call tomorrow and left.

That day, I could barely sleep, thinking about what I was going to do if he calls the next day. As the sun rose, I was as excited as I was nervous. At about 11 in the morning, he called me. He asked me to take a bus and drop at a bus stop. And to get to a hotel. I quickly got fresh and left for the hotel and reached there in an hour and a half. He had already booked a room and took me to the room right away. He was grabbing my ass all the time. Once we got to the room, he closed the door and started undressing. I asked him to stop and told him about my cross-dressing fetish. He couldn’t believe it. Funnily, he had never heard of such a thing. But I told him that I had nothing to wear. He told me not to worry and left to buy dresses for me. When he got back, he had a blue saree, a blue low cut embroidered blouse, skirt to wear under it, laced bra and panties. He had also brought a shaving kit and a few makeup items. I took the whole package and went in to the bathroom. In 30 minutes, I was all done. I looked more like a girl than a boy. He was astonished when he saw me dressed.

He grabbed me and threw me on to the bed. And me being so petite and light, it felt like I was being attacked. He took his clothes off and let me tell you, he was really hairy. He was like a bear. He came and lied next to me.He started by kissing my lips. It was a light kiss at first, but seeing that I was helpless even if I wanted to defend, he started doing it forcefully.

He started thrusting his tongue deep inside my mouth. Then he bit my lips. My lips started to bleed a little and he enjoyed it. Well, I enjoyed it too. At the same time, his hands were massaging my things really hardly. He removed my blouse and saree, and kissed my navel for a few minutes. He played with it which made me so horny. He came up to my chest/breast. I had stuffed my bra with cotton, which he didn’t like. He threw it away and started biting my nipples. Even though I enjoyed it first, when he started biting harder, I cried in pain. But he didn’t care. I was almost suffocating now because of his weight on me.

He untied my skirt and threw t away.Then he lifted me by his single hand and went and sat in a chair, with me lying down on my tummy, with face down, on his hips. He started spanking me hard, over the panties, which I really enjoyed. It was so hot because I had imagined this happening to me for a long time. After he was finished with spanking, he took me to the bed, and asked me to stay in doggy position. He took off my panty and started fingering my asshole.He used his ring finger on his left hand to drill my hole and then also inserted the index finger once it became loose. He spanked me a bit more before he came in front of me and told me to suck his cock, which I obeyed like any slut will do.

His cock wasn’t that long, just about less than 6 inches. But it was really thick and I had a hard time sucking it, since this was my first experience. But I tried passionately to pleasure him. He took my head and started fucking my mouth slowly, which I should say, was not the most comfortable of the experience. But if it gave him pleasure, I was all in to it. Then he lied down on the bed and asked me to suck him off lying down in between his legs. He would at times, bring his leg up and shove it in my face. Put his big toe in my mouth. He also asked me to lick the underside of his leg. I had no option but to oblige, considering he could easily make me do it.

Finally, when all the cock sucking was done, he wanted to fuck me. But I wasn’t ready for it. I knew it would hurt a lot. But he was adamant. He made me stand in doggy position again and slowly put his cock near my ass hole. Slowly, he started putting it in, pushing it. Then he took it back out. This went on for a few minutes, and finally, the cock was all inside. But it did hurt a lot and I had to bite on a bed sheet so that I won’t scream. He started fucking me slowly and increased his pace. Then, he took me to the missionary position and fucked again for a while. I was really tired by then. Finally, he took his dick off my asshole and asked me to sit on the floor like a dog.

He told me that he was about to cum. He came on my face partially and spilled the rest on the bed. He then ordered me to lick it off the bed,
which I was more than happy to do. We cleaned up after half an hour of rest. But before we got dressed, he asked me to lie in bed and started biting my ass. he bit so hard that he left 3 bite marks on my ass. After that, he said that he would call me again and I was to come wherever he called.

I said yes, because I didn’t want to make him angry. I left first and haven’t heard from him again. I’m not sure if I want to either…..

The End..

I hope you guys liked the story. It’s a bit long. Mail me at [email protected] and maybe we can have some fun online ;)

Mail me and I promise that I won’t disappoint you!