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Whats YOUR First Time Experience Like Having Sex With Crossdresser

The first time I had sex with a crossdresser. It was something I wanted to try, no maybe needed would be better

I had tried sex with other bi and gay guys and whilst I enjoyed the oral and anal part of the meet, I knew inside I wasn’t gay and whilst being with bi guys was great, I still wanted the feminine part.


Yep I was feeling a little confused and being married didn’t help that. When I got divorced things did change and whilst I was still using some cottaging locations for oral and even sometimes getting fucked I knew I wanted the touch of a women.


I found a crossdressing personals site one day whilst looking around and thought I would give it a try. The first thing that did surprise me was the diverse number of crossdressers, those that just wanted to wear knickers to crossdressers that you could easy mistake for a real woman, it’s those girls that caught my attention.


Sarah….Mmmmm what can I say around my age, long hair, makeup and loved to wear lingerie. She looked amazing and whilst she didn’t mention her cock she said the she love oral and anal and was versatile when meeting males. We started chatting and soon started to swap more sexy photos and FUCK what a cock and pussy she had, I knew I wanted her and even now just thinking back have a hard cock.


She didn’t go out but after messages and even talking on the phone she agreed to meet at her house and we both knew just what for.  She did ask me to shave my cock as she loved sucking on a bare cock and balls which I was more than happy to do as she was also fully shaven.


Getting to her house I pulled up, walked in and almost came in my pants she looked so HOT. She was standing wearing a tiny bra & panties, stockings with suspenders and I could clearly see a hard cock being pushed against her knickers.


We both knew what we wanted and taking me by the hand took me upstairs and sitting on the bed I knelt in front of her cock and kissed her legs getting to an erect cock now waiting for my open mouth. I was able to take most of her in as I was used to sucking a cock and she tasted amazing and even rewarded me with a little pre cum that’s was so sweet.

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She teased me with fingers, her tong and more .

She told me to strip and I removed everything other than my boxers as she wanted to take that off. Walking up to me she kissed me, her lips were soft and I wanted more, we kissed tongs swapping and sucking juice’s from each other’s mouths.


She moved down and pulling my boxers off took my cock all the way in and started to suck and fuck my cock with her mouth, it was all I could do to hold back myself from cuming, but at some stage I needed to pull her mouth away.


She turned me around and pulling my arse apart start to tease my arse first with her fingers , next tong and the way she was kissing and sucking my arse was something I never experienced both. I knew about a black kiss but had never had it done to me, Oh my god feeling her tong inside my arse pushing deep inside and then followed by fingers was something that really awoke my passion for anal sex.


She pushed me onto the bed and carried on teasing and pulling with bottom, till I felt something large against my arse, I knew it wasn’t her cock but could feel something bigger opening me up.


Slowly the plug was pushed in and then pumped to make me able to take her cock. She moved back up and rolling me over with the butt plug firmly inside sat across me, and pushing her cock into my mouth I sucked her and again had that taste or pre cum, fucking my mouth so hard I just wanted her cum,and she told me if I carried on I would get a mouthful and did I want that or to be fucked. I sucked harder and harder and could feel her cock throbbing in my mouth and pulling her arse firmly towards me she gave me the reward and shot her load.


I drank every drop not wanting to waste any and pulling out she looked at my cock and I had also cum. Moving down she liked and sucked my cock till I could handle more and moving up kissed me with us both swapping cum between our tongs.


Whilst doing this I moved my hand down onto her cock and could feel she was hard again. Now she said its my turn to fuck you…. 

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