5' 7" and about 130lbs or so, twenty-seven inch waist. We started slow. Girls' skin-tight jeans, peasant top, sandals. All done up I looked pretty and not at all like a guy. I was thrilled. We made out so hot; she loved it.One day she suggested we go to a movie. I was dressed similar to the first time. Nothing that would attract attention. No one noticed I was a guy. I felt so pretty. She called me Michele. We were like best girlfriends when she had me dressed up.Over the next few weeks, we played dress-up more and more. She thought I was very convincing as a girl. Eventually she even started dating another guy. An older guy. A very hot older guy. She promised me it was just for dates. She said she needed to be with a strong masculine man sometimes. But she assured me that she loved me. I was not happy, but I accepted this as part of our relationship. I felt I had no choice.Finally, after a few more weeks of experimenting, she challenged me to dress up super slutty with her one. ”“I gave him the cash.” She paused, then bit her lip. “Dante’s got a great cock, let me tell you.”“The suitcase, Frankie.” Bill swung the key, did a three-point turn, and drove about a mile before he was on a paved road again.“The butt-plug I wore on the way barely prepped me for him. His cock is so thick.”“You’re not going to tell me what’s in the suitcase, are you?” Bill’s grip on the steering wheel tightened and he ground his teeth.“So Dante was so pissed I took so long to call him after I got here. I told him, you know, I wanted to chill out with my family for a bit first before I tried to get the money together. Of course, at this point, he doesn’t give a fuck because he wants what he’s owed, right?”“Right…” Bill stared at the roadway.“Riiight.” She raised an eyebrow and rolled her eyes. “Anyway, so he was all pissed and grabbed me by the hair asking if I did what he wanted, to which I responded ‘yes, daddy’. So this fucker pulls my pants down, yanks my hair, and slaps me hard on.
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