The semester ended and I celebrated my seventeenth birthday on the first day of summer vacation. I got a job with a landscaping company cutting grass ...and I spent my days working and my nights running with my buddies. One night we were in Harry's Malt Shack and Norm Prince said:"Did you hear the latest? Maine Barber is pregnant. She told Dick Spaulding that he was the daddy and he told her to piss off. Then she went to Bert Ellsworth and told him the same thing and he laughed at her. I wonder. Anyway, I'm mild-mannered, 12st, 59 and have never crossdressed in my life or even thought about it, well not until two different black guys asked if I would dress for them, one who I hadn't met and one who I had.I had only met this guy twice. We met socially and chatted before retiring to his hotel roon and repeated the evening a second time. I had given him my number should he want a third, fourth or fifth for that matter!Out of the blue, he did call me one day and simply told me we are going. I fell asleep in her big bed without jerking off, and about a month out from sleeping with anyone. I was fast asleep for several hours, but I slowly woke to a pleasant sight. Catie never slept with a bra on, she'd put on an old tee directly over her naked breasts along with some cute panties. I woke to the fresh smell of her hair with a powerful erection, my nose touching her head and my erection pressed firmly against her perfect ass. My first instinct was to roll away and deal with my. Jen has to be home in like twenty minutes. There’s no way she could get to your place, grab the keys, drop me off at home and still get home in time. But your apartment is on her way home. If she dropped me off, would you be willing to give me a lift back home?’ The two girls traded worried looks in the fractured light. Melissa reached out for Jen’s hand, needing the support as she waited for Robert’s answer. She heard a sigh. ‘Yeah, I can do that. Where are you?’ Melissa squeezed Jen’s hand.