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"First time anal"

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This is a true story, not exciting but just as it was and true. I’ve been a closet cd for many years, loving dressing but thinking I was straight with it. Via SH I’d finally got up courage to meet and I’d met a couple of guys dressed and played a little, though not much.

I belatedly accepted I was bi. I’d often wondered what it was like to feel cock inside me.

I’d chatted for some time with a guy, got comfortable with him and decided to meet and see if I might succumb to anal, not sure. We hadn’t discussed it much.

He picked me up on a retail park and took me to his house. I changed into sexy black undies and a see thro red mini dress which I’d got from Love Honey. Heels and wig. I’m quite slim and he was impressed. He held and felt me asked if I kissed, I said no so we didn’t. He was a bit overweight for me but I slowly took his clothes off him leaving him naked and rock hard. I put myself in his arms, guided his hands let him kiss my neck and feel me as I rubbed my hands through his hair and over his body. On his bed our hands were everywhere, I sat across his chest. Everything was so exciting and frantic I knew being dressed as I was was driving him wild. I knew I was pleasing him and I felt like a woman driving him mad. I’d been sucking him while he sucked me.

I thought if he asks to fuck me I’ll let him so long as he’s protected. It was clear I was driving him wild and he asked if he could fuck me. I thought, sod it, and said yes with a condom though.

He said he wanted me bending over, I was still dressed except for my panties which he’d had off ages ago. I lubed myself while he put a condom on although he was so worked up he could barely stop feeling my body especially my cock and balls.

I told him this was my first time, I’d told him before I had never been fucked. I asked him to be gentle and he slowly got his bell end inside me (stretched by using a dildo on myself for quite some time weeks before). Then he started to push his cock in hard, wow it started to hurt as he thrust into me.

I couldn’t cope with it and told him to stop and moved away. I said I was so sorry but it hurt too much. He asked me to wank him off so he removed the condom and I kissed and caressed his body as I worked his hard cock until he shot his load.

I stroked his body and said sorry again, he was ok with things, he said sorry too but also said that me being dressed and all the things I did to and with him had driven him wild and he was desperate to fuck me.

In reality, I had just got him so worked up wanting me that when it came to it he just couldn’t be gentle because he desperately wanted to fuck me like crazy.

At least I got to know what a cock felt like inside me and the reason it didn’t work out perfectly was the old saying - ‘ six of one half a dozen of the other’ - both to blame but I doubt if he’s ever forgotten the morning. I haven’t.

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Written by Robyn1911

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