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First underwear experience

Posted by: Age: 16 at the time Posted on: 6 comments
8 likes 41 views Category: Sex Stories Anal Tags: Cross dressing, anal sex, gay, first time, virgin, oral sex

When my friend found my mum's sexy underwear


My parents were away for the night and I could have a friend to sleep over. It was a normal sleep over, me and Kevin had planned a take away, and games console night with a beer or two.

For the first few hours all was normal, until I popped to the toilet only to come back with Kevin holding my underwear in his hands. To say I went red with embarrassment was a understatement, he asked who's it was and what I was doing with it, So I came clean explaining I enjoy wearing women's sexy undies while masturbating and playing with my ass.

To cut the story short, he asked me to wear it, which I did, stockings, suspenders, bra and painties (my mum's). i got hard straight away, so did Kevin, he was only wearing his boxers and his hard cock had started to poke through the front slip. 

I took the initiative and asked him to stand while I knelt in front of him, taking his five inch cock in my mouth. i sucked my first real cock and my! it was wonderful!

After ten minutes or so he said he wanted to fuck me. I bent over my bed, he quickly slide his cock inside me, not an issue as I'd had larger objects up there, he must have been turned on as he just went as fast and hard as possible, taking my anal virginity. Oh how I'd loved every second of it! Before long he said he was going to cum, so I begged him to cum in my mouth, I turned around and just got into position with his cock an inch from my mouth when he started cumming. I managed to catch some in my mouth and it tasted great. Once I sucked him dry I got undressed, and we settled for the night. 

Was a great first experience that I look back on fondly

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