Forced Crossdressing: A Collection of Forced Crossdressing Stories

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Honey she said smiling you must let go so you can put your arms through the bra straps. As I let go expecting the breast to fall they just hung there pulling on my chest. Mom could tell what I was thinking as she spoke up. I eliminated most of the replies and narrowed it down to two that seemed promising. One of the ‘finalists’ was only available that night, which was not possible, so now I was down to one. I was hoping this would pan out. I’d hate to miss out on this opportunity. I only had a few days. So this last prospect sounded really serious. He just needed 20 minutes notice to get there, and promised he would show up. 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.

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

Tiffany kept at him, "Well, my parents are out of town and Jess and Michelle are coming over to hang out. Michelle thought it'd be fun to invite you over too." Holly had also been disappointed because she had planned on giving Amber photos of Derek dressed up like a sissy for her birthday. Angela also worked in town at a busy store and they both used to catch the bus to and from work Monday to Friday and sometimes Saturday for Angela. Tiffany grabbed another spare pair of dirty panties that were laying nearby and stuffed them into Chris' mouth.As he pulled up in the van, he could see his sister standing alone against the wall near the gymnasium. They were Angelina and Dana. Both were 17, in junior year, and both were members of the soccer team. I was a freshman and on the baseball team. Honey she said, how did you like getting your nails done dear. Before I said anything I gave her a big hug. It’s my old hair dryer silly it will help speed up your hair drying. As the hair dryer hummed along she started on my face. I could tell she knew just the look she wanted as she really didn’t say much except for the occasional wow you are going to look fabulous tonight. When she was all done she had me sit next to her as she applied her makeup. I just sat there and watched as I still loved the way she did her makeup. I always enjoyed wearing my mom's high heel shoes and dresses. They made me feel powerful and confident. Even though I was a little, I thought I could do anything in those shoes. Now that I'm all grown up, I still enjoy wearing high heel shoes and dresses. They make me feel sexy and beautiful. And I love the way they make me feel powerful and confident.

Stories by Janet L. Stickney (Page 7) - StorySite Stories by Janet L. Stickney (Page 7) - StorySite

Are you hungry dear mom asked me? I was hungry as I hadn’t eaten sense lunch and didn’t even think about how I was dressed. We went in and had a lovely dinner and spent the time talking like a mother and daughter would and no one seemed to pay us any attention. When we got home I was on cloud nine and I was walking on clouds. Mom helped me take my makeup off and gave me a night gown to wear for bed. I slept so well that night as for the first time I dreamt I was dressed in beautiful dresses with my makeup perfect. The rest of the week went great. I would get home and do my makeup. Friday morning when mom dropped me off she smiled and kissed me goodbye. Once aunt left, I had the urge to peek into her boudoir, and there on the bed, was a lovely shade of pink, nightdress. Oh gosh, as I stared at it, but dared not touch it, in case aunt had placed it, in a certain way. Weakness of a man overcame me, and I found myself holding it up in front of me, then dropping the towel, to the carpet, and stood in front of the mirror, and with a rampant erection, as I had not mastur-bated for about five days. Oh gosh, as I was now mesmerized, then it touched the top of my pe-nis. Oh no, as I hoped my precum had not stained it.Sweetheart she smiled, you didn’t let me finish. There is one other choice; you could be Rachel for the whole time. I was about to say something when mom stopped me. Just wait dear she said, before you make up your mind if you do choose to be just Rachel for the summer I can help you but it will not be as easy as being Rachel on the weekend. I thought about it and I really liked the idea. Jess, Michelle, and Chris could't understand what was so funny and waited eagerly for her to calm down enough to fill them in.