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Discovering crossdressing.

We sat down to have a few more beers and had chatted for an hour or so when my arousal got the best of me and I decided to go for it. Mid conversation I walked over to him, got on my knees and started to undo his pants. He lifted his ass to help slip them down and was greeted by his cock popping up in my face. The room was silent and they were both watching as I let the head of his cock slide past my lips and into my mouth. Like I said I had sucked cock before and I certainly knew what I liked, so I made it my goal to give him the best blowjob of his life. His moans made me think I was on the right track. Next thing I knew he tapped me on the head and told me he was cumming. I was unbelievably turned on as I held the head of his cock between my lips and he filled my mouth with jet after jet of warm cum. Normally I would have been hard as a rock but the chastity device was doing it's job well.

Dave then stood up, zipped up his pants, chugged the rest of his beer and made his way to the door. "Thanks for the blowjob, I'll see you girls later"

"You can drop by tomorrow if you like." Lisa said before I had a chance to respond. Dave looked at me for conformation and all I could do was smile as he closed the door and headed off.

"My turn!" Lisa shouted as she pulled down her pants and flopped back on the couch spreading her legs and showing me her shaved pussy. "God I need to cum after watching that!"

Now eating pussy is something I have done a lot and I'd like to think I'm pretty good at, and Lisa's pussy is a pleasure to go down on so I immediately went to work. After I brought her off we moved to the bedroom. I was beyond horny by this point and heard the best phrase I could have heard. "How would you like to fuck my brains out right now?" The look on my face said it all. "Great, I'll just go get the little something we need then." she said heading to the closet. To my surprise she returned handing me a strap-on dildo rather than the key to the chastity device and all I could do was stand there.

"You agreed to live like a girl for the weekend didn't you? Girls don't have penises to use so we have to make do with the tools available. Well, go on strip down to your lingerie and strap up I need it bad."

Like I said I was beyond horny and would have done just about anything so I stripped down and stepped into the harness pulling it up to my waist. It felt very odd to have my caged penis pushed down and out of the way while a rubber cock slightly bigger than mine stuck out in it's normal place. By then Lisa was naked and begging for me to take her. We then screwed in about six different positions and while she had five big orgasms while I didn't feel a thing. I started to complain but she reminded me of all the quickies we have had that she didn't get to cum. "Girls don't always get to have orgasms, but we can try for you next. Go wash the strap-on and give it to me."

The final part of my fantasy was coming true next, letting Lisa have her way with me was the ultimate in submission and I was ready. It was a little weird, I had absolutely no desire for male contact in that way (I enjoy giving head but that's it) but the thought of her taking my anal virginity was incredible. She had me remove my thong and lay on my stomach with a pillow and towel under my hips. Lisa was very gentle and with lots of lube used her fingers to relax and loosen me up. Finally she asked if I was ready and lined up the head of her dildo with my ass. With a moan from me as confirmation she slowly pushed into me. It was awkward at first but soon I relaxed and began to enjoy it, before long she was thrusting in and out like a pro. It felt fantastic. After what felt like an hour (I have no idea how long it was) she pulled out and said it was time for bed. I sat up and noticed the towel was wet with cum. I guess this was my introduction to milking. Lisa gave me a short nightshirt to wear to bed and I drifted of to a fitful sleep after not receiving any real satisfaction.

"Hey baby, how's your ass this morn

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