anal
18/06/2008me and my girlfriend wanted to try something new, so i sugested anal and she said she would only taking it if i had exprienced it first. Obviously i was reluctant but she expland she would put a strap on on and give it to me. However i still needed a lot of convincing. Once i agreed she said we had to do it dressed up as the opposite sex to which i also agreed.
A few days later she said she...THE STORY CONTINUES BELOW....
...would go out to the sex shop and get a strap on and dress up as a man and when she returned i was to be dressed up as a woman and we would then go at it. So she left the house with a bag of my clothes and i went up stairs.I started to look through her clothes decided to dress quit sluty (not hard with my girlfriends clothes) we had agreed to wear each others under wear as well ao i put on a pair of her frenchies (red) which were a bit of a squeeze and one of her bras also red. I then put on a short skirt and a very low cut top. It was very uncomfatable but i was excited if a little nervous. I went to wait down stairs.
A while later hannah returned and i went to the door. She was wearing a pair of my shorts and a polo.
"Well dont you look lovely"
"Your looking very hansome yourself" I replied
With that she stated to kiss me, really taking the lead which she never does, she even put her hand on my "breast" whilst i was cupping her ass. We moved up stairs and continued kissing untill i eventually started to feel her crotch. This was a very strange thing to do and the strap on she had seemed quite big.
She took my top off and started kissing my chest and i started taking her top off as well, she hadnt worn a bra and her tits looked amazing.
I then took the plung and moved down on her yanking down her shorts which revealed some of my boxers(fcuk tight ones) i started kissing her strap on through the boxes then took them down. I took the strap on in my mouth and started sucking very slowly.
Hannah started talking dirty to me telling me to go harder and how i was a slut. After a few minutes she pulled me back up and took off the bra and started to kiss me through the skirt untill she took that down as well as her frenchies
She then moved inbetween my legs and started kissing me hard again, moving my cock out of the way she took the strap on which had been lubed up by my mouth and placed it at the edge of my ass.
Looking me straight in my eyes she slowly pushed it in. this hurt like hell and i screamed out in pain but she didnt stop. she started to slowly pump away and the pain went away and was replaced by a slight pleasure. She started to pump harder and harder still looking each other dead in the eyes.
"Moan like the bitch you are" she demanded in a sexy voice so i did she kept pumping away for about ten minutes as i kept moaning it and enjoying it more and more.
Eventually she moved out and started to kiss my body again then moving up and kissing my mouth she then whispered very seductivly in my ear
"roll over"
so i did and went on all fours. She positioned herself behind me and once again entered me. It was even more pleasurable this time and she was pumping away like a pro. After about five minutes she reached around with her hand and grabed my cock which was rock hard. She started to wank me off untill i came about five minutes later. We stopped there but later that week we did it again but this time the proper way round and let me tell you it was all worth it
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