I started dating this super cute,young, thin, sexy girl about a month ago. I knew she was either a very convincing crossdresser or a tranny and she did admit it after our second date as we started getting romantic with kisses. I'd not dated, but did fuck a tranny before, mostly dated or lived with women, and have had some men in my past as well. She wouldn't let me reach between her legs, but I did get to feel her little A cup breasts (if even an A cup) and her bare bottom. She started jacking me off, then gave me a BJ. That went on for 3 weeks, I started getting more demanding, and she told me that she didn't let anyone fuck her, she never had done it. Last night in her apartment I told her getting blown wasn't enough. She had a thong on covering what I eventually saw was a tiny little cock about the size of my thumb. I wasn't interested in that little thing, I wanted to fuck. Kissing her and rubbing her butt my 8" hard as a rock, I rolled her over and she started yelling to stop but I was too far gone. I brought my own lube and after I got myself lubed up, she was crying, begging me not to do it, and tried to get up out of bed. I roughly pulled her down and got on top of her and fucked my crying young virgin. I wasn't gentle, I know it had to hurt. After she just laid there whimpering. Eventually she stopped, and still just laid there. I kissed her a bit with no return kiss or pucker from her. I went down her belly and brought out her little cock and gave her a bj. "No" was all she said; I continued anyway. As she was approaching orgasm, I stuck my finger in her sperm lubed ass and rubbed her prostate. She blew off and her whole attitude changed. She was no longer a woman who was forced to give up her butthole in a violent r**e, she was someone who had (as I found out) gotten her first oral sex to her orgasm. She'd only jacked off prior and that not very often.

After that I let her recoup, then started on her again, and when she was approaching another orgasm I pulled up between her legs with her on her back and inserted my cock again. This time for a very gentle fucking, while I played with her little cock. She blew and I scooped her sperm into my mouth and into hers, we shared it and both swallowed. She'd already swallowed mine many times by that time. I continued fucking her and she never lost her little hardness in that tiny cock.

This morning she met me with breakfast, a cute nightie with no panties, and while I ate, she danced and lubed her asshole again. We fucked and I left. I guess I did force her, I r**ed her really but I now have a girl to have full sex with, nothing held back.

Comments

Anonymous

by Anonymous

Last summer I had my cute sissyboy bottom rudely taken by an experienced aggressive top. He knew I was a boy, virgin and just wanted to make out. I'd blushingly suck him, but surely didn't want that big thing of his getting in my ruffled panties.

After a few dates he had other intentions though. My deflowering was similar to your friends. Maybe that's how it's supposed to be?

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Anonymous

by Anonymous

When I was a littler kid an older boy had sex with me. It was soon after I lost my virginity that I started trying my sister's clothes on. They made me feel freshly pretty and felt so good that I started sneaking out dressed in them.

That's how I ended up having sex with a man the first time. He was all over me and when he got his hand up my skirt he could feel I was a boy through the panties I had o. He didn't care!

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Anonymous

by Anonymous

All total BS, even the comments.

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