Forced Crossdressing: A Collection of Forced Crossdressing Stories

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Now we sat there at lunch and we talked and I was scared again doing my best to make sure she didn’t figure it out. I would talk to her as we have always been best friends plus I didn’t want her to notice how close I was watching her do her makeup. Are dinner came and as we ate Helen was still talking about marriage and I felt bad for Jill as she was taking all of this by herself but as much as I wanted to help I had to stay in the Kelly roll. As I hung up the phone I saw mom and Jill looking at me and all I heard was mom say, did you forget about your girlfriend?

stories: Aunty Helps Me (Crossdressing) - Blogger My dressing stories: Aunty Helps Me (Crossdressing) - Blogger

Helen must have realized what had happened as she told me she felt like it was her fault for startling me.

Mom placed them both on my chest and kept adjusting them till she had them right where she wanted them. I told Susie I had to work late you know making deliveries and we would go out the next night and do something special. Once aunt left, I had the urge to peek into her boudoir, and there on the bed, was a lovely shade of pink, nightdress.

Forced Crossdressing Short Stories Stories | Quotev

She smiled at me and asked how I like the color and it looked great on her but I didn’t say that I just told her she looked beautiful which she did and I didn’t want her to know I was thinking about the lipstick. Jill walked in at 6 and Helen got up and gave her a hug I stood up and Jill looked at me and said wow girl you look fabulous and also gave me a hug which helped as I was a little worried about all that had happened today. They were talking to each other and without interrupting, Chris pulled up a chair and sat with them. You wade through the people surrounding you, trying to find a place to sit alone until you bump into a building.Go ahead dear she said, it is just a moisturizing lipstick no color so you can wear it all the time. Believe it when I see it, but nonetheless, I was pumped, excited, nervous, scared… all the normal emotions I always feel when arranging a meet up with a complete stranger. She was going out of town to spend it with her grandma while I stayed home and spent it with my mom and sister Jill.

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Letting myself in with the key my friend had given me, I locked the door behind me and went upstairs to the bathroom. Since his parent's had left for their getaway on Friday morning, it was up to Ben to pick his little sister up from school that afternoon. She set the paddle down and released my feet and then pushed a couple keys on her laptop and the humming sound stopped and I could push the top up which I did. It was about 3 inches away from fully zipped and he noticed the pull that the dress had around his waist and chest. Ben thought that she was just being young and dramatic and that he could make it up to her somehow over the weekend.

I was really scared and the more I struggled but nothing worked I was trapped and as bad as it was my only hope was that Sarah would find me and set me free of course that would mean an end to our friendship. minutes or so later when my friend and two of our other buddies (who I didn’t know would even be there) walked into her room to check out her work. My valise case (a small travelling bag), just carried my bathroom kit, a few underpants and tops, a pair of blue jeans, a white ladies blouse, full sleeves with a Peter Pan collar, a pair of white knickers and ladies beige slacks, with a button and zip, side fastening. She didn’t seem to even notice my size and we became friend and soon we were dating which was a little hard as I was an inch shorter than her and more than once people mistook me for her little brother. I had always and still am, very fond of her, and fantasized about her, when in bed and in the shower.

MY DISAPPEARING BOYHOOD - Crossdressing Story MY DISAPPEARING BOYHOOD - Crossdressing Story

We spent the day together and had a great time and when I left I was wearing the bra and panty under my clothes.

I would say we had become friends which was so nice as I really didn’t have many because of my crossdressing.