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Adult Dress-Up With My Sister

Posted by: Age: 45 Posted on: 2 comments
14 likes 5779 views Category: Masturbation Male-Female Tags: brother-sister, handjob, lingerie, exhibitionist, sister
I discovered I had a submissive, slightly sissy side to me when I was a kid and played dress-up with my sister. Thirty years later we started doing it again.

When I was younger, I began playing dress-up with my sister. We had an attic with some suitcases full of clothes. At some point, we decided to switch clothes, so that I ended up dressing as a girl. I found that I liked how I looked and felt wearing girls clothes. We did it several times, and each time, I would get an erection from it. My sister would tease me about it, and I would feel embarrassed, but then we would continue. Among the clothes was some lingerie. My sister would have me strip naked in front of her and would choose what I should wear. I remember getting terribly excited and aroused, standing in front of her completely naked, waiting for her to choose what I would wear, and then her helping me dress into an old-fashioned negligee or slip, even panties. Eventually, we tired of the game and moved on. But I never forgot that feeling of excitement wearing female underwear. 30 years later, both my sister and I were married and divorced. When I lost my job and needed some temporary housing until I got back on my feet financially, my sister let me move in with her. One evening after dinner and a few drinks, we were reminiscing about our childhood when the topic of playing "dress up" came up. I told her how I enjoyed it. My sister laughed and said she noticed that I enjoyed it very well, judging by my stiff penis. Thanks to the drinks we had, my tongue was a little loose, and I let her know that the experience led to a life-time interest in female lingerie. My sister got intrigued and suggested we play again, only she would really make me look feminine. Not sure what she meant, my sister led me into her bedroom where she proceeded to put some eyeliner and mascara on my eyes and a bit of blush. I have to say she did a good job. Next she pulled out some lingerie of hers and laid it on the bed. She wanted to recreate the experience we had in the attic and asked me to strip. I could already feel an erection coming on, so said no. But she insisted, so eventually I did. I stood in front of her, naked, my cock throbbing, while she held up different garments and finally had me put on a negligee she used to wear when she was married. After admiring her handiwork, she looked down at my cock. By now it was aching badly. "We need to do something about that," she said, so she asked me to lie down on the bed. Deeply embarrassed, but too aroused to say no, I did as she asked. She reached for one of her panties (they were silk and smooth) and then slid her hand under the negligee and began to stroke my cock with the panties. It didn't take long before I began groaning and shot a massive load of cum into them. My head was spinning from what happened. Since then, we played adult dress-up several more times with the same results. I've tried to coax my sister into letting me reciprocate. It hasn't happened yet, but I'll keep asking as long as we keep playing.

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