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He was a senior and very cute. Preppy guy about 5'10" and 185 lbs. I believe he played wide receiver for the football team. He asked if he could come ...n.He came inside and offered me a beer and we began chatting. Paul finally asked, "So is it really true you like dressing like a girl, or was that just a one-time deal?" I don't know why, but I admitted I liked it. He then asked, "Can I see?"We went back to my sister's room and I did my makeup and put on a blonde wig I stole from my mom's closet. I said sorry and she was like, let’s have dinner and went to the table. I sat down had dinner and left. Then she became bolder and started inviting me to her home every afternoon for lunch. I had a lunch break in the office of one hour but started spending more and more time at her house every day.This went on for more than 3 weeks and she asked me to come home on a Saturday morning with a winking and kissing emoji. I went there fully dressed up, even shaved my balls and kept a condom hoping I. Right, Ted?"My face turned bright red, and so did Peggy's."See, what'd I tell you? But like I said a minute ago, you don't have anything to worry about, I'm not going to take it off. When we get to this point we can't take anything off without first getting dibs on it. So now, I get dibs on your blouse. Like this." And he rubbed his hands up and down the side of her chest, caressing the material of her blouse.She buried her face in her hands."Come on," he said, "it's Ted's turn."God how I. I joked with him “spare me the details Steve” and we both laughed.After talking to Janice about having anal sex I decided to go and talk to Steve. He said the first time a girl takes it in the ass it really hurts, so be careful. But if you use a ton of good lube like Astro-glide and slowly go into her about an inch at a time it will be less painful. Then when your whole cock is inside her just stay still and let her sphincter and ass muscles get used to the feeling of a cock being inside her..
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