Putting the work in

This gay guy from this site messaged me and said he was happy to dress as a girl for me if I wanted to fuck him. I looked at his pics and he looked like he could pull off a decent girly look if he dressed right but I wasn’t going for it. I was sick of topping everyone, my ass has needs too. I told him it was only going to happen if he was going to fuck me whilst wearing girls clothes. He agreed he’d come over to my place as long as he could get changed here into a girls outfit but then said he didn’t have any girls clothes. I moaned. It had been so long since I’d had something other than a toy in my ass so I logged on to a few websites and ordered some slut suspenders and panties/bra, a wig and a cheap makeup kit. I set a date for a few days away and gave him firm instructions: the door will be unlocked, the lingerie, makeup and wig are in the master bathroom, let yourself in, the more makeup the better. When I hear the bathroom door close I’ll come and lie on the bed and I’ll be waiting for you when you come out. I suspected he wasn’t very experienced and so I told him I expected no body hair.

The day came and I was sitting in my living room when I heard the front door open and then my bathroom door close. I walked straight to my bed, turned my red lamp on, turned the other lights off and took off all my clothes. I had the bed side table prepared nicely, with a few condoms (which I don’t like to use if I’m topping but bottom I couldn’t care less), a tube of lube, a butt plug and 9” dildo, just in case things got really wild. I put on a ball spreader and dabbed a tiny bit of lube on my freshly smoothed ass hole. Then I lay down and waited. Would he be like his pics or had I been fucked over? Eventually the door slid open and I was very impressed. He was now a very convincing she in the dark, with the exception of no tits. I should have bought tits...

She asked “is it okay?” and I said it was more than okay. She didn’t seem to know what to do next so I sat on the bed and pulled her towards me. I put my hand on the front of her panties and she was still limp and she was clearly extremely nervous. I started rubbing my hand up and down the front of her panties and I asked if she was nervous and she simply nodded. I asked if she’d ever fucked anyone in the ass before and she shook her head. I lay her down on the bed and told her to relax, everything was fine, then I told her to close her eyes. I needed to get her relaxed and hard, so I spread her legs, pull her cock out of panties and started to kneed it slowly with my hands.

I put it in my mouth as it was still limp and just kept flicking my tongue up and down against the very tip and it started to come to life. Then I moved upwards until I was kneeling next to her head and told her to keep her eyes closed. I was so hard, it was a shame she wasn’t a full time crossdresser because in women’s lingerie she was stunning. I pressed the end of my cock into her chin and then began to run it around her lips. She reached up with her mouth to try and suck it but I kept it just out of reach. She opened her eyes and grabbed it and put it in her mouth, this was clearly far more her thing and she started to work hard on it, but I was more distracted by her own cock. She was now fully hard, so as she kept sucking my cock I grabbed the bottle of lube and put a few dabs onto her cock and then worked it all over.

I got into the cowgirl position then I reached behind my and grabbed her cock. It wasn’t huge but it would do the trick. I let out a huge groan as I sat back and felt it go all the way inside me, as much from relief at finally having a cock in me after so long as from the pleasurable sensation. I began to bounce up and down on it, inhaling loudly as the initial minute of pain turned into the feeling of intense anal pleasure. After a few minutes my legs started to tire and so I climbed off. I told her to swap places, so I lay down on my back, grabbed by knees and lifted them as high as they would go. I told told her to fuck me, fuck me hard, fuck the shit out of me. She put her cock back in me and slowly began to thrust. HARDER! FUCK MEEE!!!! Harder, harder, harder. Yeah, that’s it, keep fucking, fuck it hard. Do you like my tight ass? Do you like my cock? Fuck me!

I told her do not cum in me. Tell me when you’re about to cum. She kept fucking and fucking. That’s it baby, you’re doing well, fuck my hole hard. “I’m close” she strained as she started to slow down. I pushed her cock out immediately and lay her back down with her legs spread and I got down between them. “Tell me when you’re gonna cum” I said as I grabbed her dick and started tugging it, glistening in the red light with all the lubricant on it.

I swapped hands over and with the hand I’d been tugging her cock with I took a finger and pushed it against her ass hole. It was clenched so I wiggles my finger a little but to give her ass some encouragement and eventually the finger slipped in. After sliding it in and out a few times I hooked the finger so it was pressing right onto her prostate. In almost no time at all she said she was cumming and this was what I had been waiting for. I put my mouth over the end of her cock and formed a tight seal with my lips. Ooooaaaaaaooooowwww she moaned and then it happened. The warm liquid hit the roof of my mouth and then went straight down onto my tongue. I kept the seal tight as the cum kept on cumming, another spurt every few seconds for about ten seconds each spurt I was pressing and then letting go of her prostate. After I was sure she’d finished, I pulled my mouth away with all the cum still in it and sat up and then swallowed. There was still cum all through my mouth and so I ran my tongue through mouth a few times to make sure I got all of it.

I was so aroused at this point, I still had the post-fucking feeling in my ass and I told her not to move. I kneeled over here and pulled at my own cock, looking down into her eyes, waiting to put my cock in her mouth but unable to wait even a further second for release. I stopped jerking just at the point of orgasm and shot all over her stomach. I wiped the end my cock on her panties and then I collapsed on my back beside her.

I loved the whole experience and mind went to repeating it so I told her how amazing she’d been. She seemed pleased, and then asked if she could have a shower. She left afterwards, sadly back to guy outfit. She was a regular for a few months, usually as a bottom though, before she, met a guy and that was the end. The first experiences with a new partner are always the best ones though.

Which just leaves me with a few sets of size 12 lingerie and nobody to wear it...