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I am a thirty-something crossdresser. This is the story of my first sexual experience as Jackie.As my male self I was a very conservative Manager for ... very large corporation headquartered in the San Francisco Bay area. There was no way I could come out at work so I limited myself to going out as Jackie after work, I would go to restaurants and bars in the bay area and was having a great time. I joined a couple of TG organizations in the area and found some great friends.One evening I was going. Just as our mom said “Okay, good night dear” I pulled out of her tight pussy and erupted. I gushed cum into the crack of my sister’s ass, down her butt to the bag. When I was done convulsing, I lifted off her and went back to my side. Helen was grinning, her eyes sparkled in the dark, she whispered “You messed up my bed.”“Better than in you.”She put a hand on my cheek and pulled my face close enough she could breathe in my ear “Yeah, maybe, but I’m not done, I hope you can get it up again.” . More

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