I was 14 at the time. I was at one of my female friends house and we were just chatting about school and stuff. Not to long after being there we some how got onto the topic of dresses and bras, and with me being a secret crossdresser i was familiar with these types of clothing. I had dropped many times before subtlety that i kinda liked to dress and she remembered this. She said she would dress me up and let me have the time of my life. I, of course, accepted.

We spent about half an hour on make up leaving me with bright red lips, blue and pink eye shadow and all the other basics. She then got a matching bra and pantie and told me to put them on. For some reason, that i don't know of, she had some D cup silicone Breast forms in her cupboard. I slipped them into the bra and it gave me a great feeling. she bought out a corset with suspenders attached. it was hard to get on but after i had a beautiful hour glass figure. she bought out black stockings and some knee high leather boots. after putting all this on i felt even more feminine then i ever had before. we went to her mothers closet, because she was out of town, and found me multiple outfits.

the first was a business skirt and blouse, after that a beautiful red dress, then to top it all off she had me wear her wedding dress, which was amazing. we walked around for 20 minutes talking and trying to find some more stuff. we found a brown wig with hair that went half way down my back. she styled it very well and we proceeded talking.

an hour later we were lying on her bed talking, both very close together. we got into an unbreakable gaze and started to kiss. we got serious and were really getting into, she then stood up and said ill be back. i waited for a minute waiting to see what she was doing. she came back with her mothers *****, she jumped onto me and we kissed some more. she then said "bend over you little **** im gonna ride you till the sun goes down". excited, i bent over and she put it straight up my ***, she kept pushing it in as far as it would go, i was almost screaming. she then rolled me over and jumped on me, pushing it in even further and we kissed for about 15 more minutes.

after the excitement was finally over, we lay there getting our breath. i still knew that the penis was in my *** and loved it being there. we talked some more and then i realised i had to go. i got undressed and removed the make up. i asked her if we could do this again and she said anytime.
Thecdman Thecdman
26-30, M
4 Responses Aug 19, 2014

Unbelievable!, as in I don't believe the story

a fantastic and sensual story. you had a fantastic friend

Great story

It was, we now do it on a weekly bases and shes now my girlfriend!

That is so awesome hope I can find a girl like yours

Dude you have no idea how lucky you are

You have no idea

There a dime a dozen but when you've got them they're there to stay.

2 More Responses

sounds like a fun night