Boards - confessions - Hi I am Mark I am 19 very shy boy, I still live with mum and probably will for a while as since I ha

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05 Mar 2017 10:23PM

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Hi I am Mark I am 19 very shy boy, I still live with mum and probably will for a while as since I have no job I can't get a place of my own. I spend quite a lot of my time on the net looking at porn, I found this site a few months back and my god I love it. Now being very shy I had never been with a girl, not that I didn't want to, but I have never been good at talking to girls, My only friend Is David, we have been friends since we were 5 and he is very like me, shy and never had a girl. Now I am quite short and skinny as a rake, David is a bit taller and also very skinny. A few months back we were looking on the net and found some pictures of cross dressers. We were at his house alone and we raided his older sisters clothes and we were soon dressed up like girls, she walked in and caught us, I thought we were going to get into some real trouble but she laughed and said we both could pass for little girls, so began the blackmail, she called me up one day out of the blue, said I should come over, I told her I was busy but then she said she would tell my mum what I had done. I got there and she answered the door, she only had a towel on, now I had always had naughty thoughts about her but never thought anything would happen. She told me to go up to her room, on her bed was her old school uniform and a matching bra and panties set. She told me to put them on, I was stuck between a rock and a hard place, so I picked them up and was about to head to the bathroom, she told me no, I had to do it in front of her. I had no idea what was going on, but she told me to do it quick or she would call my mum. I stripped off to my underwear, and she told me to take them off too, I did as she said, my cock was semi hard and as I stood there naked I put on her panties, then bra and was soon dressed in her uniform. She sat down and put make up on me, and with the bra stuffed I had to admit I did look like a girl. She stood up and said I deserved a reward, she let the towel fall to the floor and she was naked in front of me. She put the towel back on told me to change and get out. I was so confused but did as I was told.
The next few weeks she would call me almost every day when she was home alone and get me over dress me up, she would always let me see her naked at the end of it. Then one day she opened the door naked, as soon as I was in the house she told me to strip, we were both naked and my cock was rock hard, she grabbed it and pulled me to the bathroom, sat me on the bath and shaved all my pubic hair off, under my arms and legs, all that time my cock was hard. She said she was going to do something else to me today and told me to close my eyes, she came back in and told me to open them, she was wearing a strap on. She told me to suck her cock like a good little girl. Again I did as I was told, and after a while she told me to bend over, I felt her fingers at my ass they were wet and she slid them in, I have had things up my ass before but she pushed that strap on in me and fucked me hard and rough, it hurt like hell and I knew I must be bleeding too, she finished and came round in front of me, she slid 2 fingers in her pussy and pulled them out and pushed them into my mouth, that was my reward. I was in so much pain but it got better. I will tell you more if you all like part one

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Anonymous

05 Mar 2017 10:46PM

yes tell us more!

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naughtyallthway

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05 Mar 2017 11:15PM

Tentatively curious. Do continue.

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Anonymous

06 Mar 2017 12:01AM

Dude don't you have pussy at home. Own it. First sniff her underwear it doesn't matter if they're not used. The action alone will give a healthy stiff. Now wrap the panties on your hard on and stroke. Don't cum. Save that for her pussy.

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