I hadn't really thought about it, but my friend with benefits, Steve, DOES look a little, well, MORE than a little feminine. He has a girly, hipped figure, and is quite small for his age. Certainly not a muscular hunk. We were goofing around in my room, talking about sex as usual, and I asked him if there was something he particularly liked, or, better yet, something he really wants, but has never yet done.....
.....well, talk about mood killer! Suddenly, he went very serious. "I'm afraid if I tell you, you won't want to see me any more." (Oh fuck....what is he into?) then he went on....."I've always wanted to dress up. Dress up as a girl. But.....but not in clean clothes....if you know what I mean?" Well fuck me with a pineapple! I felt an immediate rush of wetness....I was going to enjoy this. I grabbed him by the hand and pulled him into my bathroom and made him strip. "Well, we girls often shower together" and while we were in there, I very carefully shaved every inch Of him. "There! Now your pussy is as smooth as mine. Now, lets get you dressed." Once dried off throroughly, I used my talc and deodorant on him, before picking a discarded bra from my laundry hamper. It was, I must admit, quite sweaty, but thesweat, coupled with the deodorant worked. Next, I plucked yesterday's panties out. They were still moist (and so they should have been....I'd cum in them several times). As I slipped them up Steves legs, he started to get a semi. "Hmm...looks like your clit it swelling a little." And with that I tucked it between his legs. It's remarkable how a guy can look like a girl if he gets his cock far enough between his legs. So, panties on, and he though we were done, but I had other ideas. Next, I chose a dress...a nice summer flowery one. And after that, I sat him at my dresser and applied some make up. When I'd done, he really could pass for a girl. So much so, that I insisted we went for a walk through the fields to my favourite outdoor barn. As he relaxed he got more into role, and we even agreed a name for 'her'. When dressed like this, she becomes my close friend, Jessica. Me? Oh I was melting! My quim was leaking into my own panties so fucking much! I hadn't made any plans for what we would do in the barn, whether he would fuck me, or whether we would be two girls together, or maybe even two girls, one with a very realistic strap on....I just figured we'd wing it. I did, however, decide to tease him. I remember d what his ex had said "sometimes, the dirty cunt asks me to pee on him....even pee my panties." As we got to the barn wall, I pulled him around to look at me, while I hitched up my skirt, squatted and slowly wet myself. 'Jessica's' eyes were like saucers as she watched me, and then, to my surprise, she lifted her dress, squatted and paused for a moment, silently asking my permission. I nodded, and she slowly peed into her panties. Then, she stood me up against the wall, and took my skirt off. Leaving my panties in place, she sucked me, while wriggling her fingers deep inside me. It was without doubt one of the most erotic things anyone has ever done to me, and I came hard. Then I leaned her against the wall, and slipped the dress off. She looked so good in my bra and panties. By now, however, his cock was hard and needed release, so I tugged her panties down a little way, and sucked it. Then I realised that I wasn't being fair. I fingered myself until I was slick and then pushed first one, then two fingers up his arse. "Oh Jessica.....can I finger you?" Bless him...he was so into role that he started rotating his hips and when he came I felt it deep in his bum, By now I was ready to go again, and I led him into the hayloft, and lay down. He spread my legs, and pulled my panties aside. I let him screw me like a girl would with another girl. Afterwards, Jessica told me she wanted me to fuck her with a strap on one day........well, why not?
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