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It was amazing, it had been over 6 years since I last crossdressed or had any anal play, but I did not hesitate and quickly slipped into the white thigh high stockings and 5 inch white pumps. She then asked, "Have you ever been fucked before?". I felt very comfortable around her, so I told her about my crossdressing and anal play experience, but that I had never been with a man or fucked before.I wanted to get on my knees and suck her "cock" but instead she wanted to do some cock sword fighting the entire time telling me my cock was smaller than hers. She then told me to get on the bed doggy style so she could fuck my ass. I did as I was told, but was shaking with fear and anticipation since I have always controlled what went in my ass, how deep, how fast, and when I had enough - also my ass was really tight now since I had not been stretching it on a regular basis for years. I felt the lube as she squirted it on my ass. I could tell she rubbed some on her strap on, but wasted no. She asked if anyone else was home and I said "no". She asked me if I wanted to watch the movie here with her and I said "sure". We went downstairs to watch the movie. I put the disc into the DVD player and the movie started playing. Half way through the movie there was a sex scene and Olivia started moving around a little. To my surprise she started rubbing my dick through my shorts. "Do you want to have some fun?" she asked. Getting a little horny myself I said, "sure". She pulled down my gym shorts and started to suck my dick. She spit on it then stood up and pulled down her bootie shorts and panties. All she had on now was her shirt! I stood up took off my shorts, my boxers and my shirt. After I took off my shirt, she did too. Olivia is one of the hottest girls I know, with her being 5 foot 5 and having brown hair and 32c sized boobs. She pushed me down onto the couch. She started sucking my dick again and within minutes I shot out about five strings of hot cum right into her.
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