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Female friend releases my inner sissy
I am Sean, but I secretly prefer Shawna! I am a closet sissy crossdresser. I used to be a fairly normal boy, but one day a female friend of mine drastically changed my life forever, and she doesnt even know it.
One day, about thirteen years ago now, I was hanging out on the couch with my female roomate at the time. We were both bored out of our minds since the area we lived in had nothing for entertainment. Out of the blue, she shot up with an evil and big smile on her face. She asked me to follow her down to her room. I was a little nervous and unsure but I followed her like a little puppy dog down to her room. Once in her room, she picked out a lacey pink nightie and asked if I wanted to wear it. I said no, but she assured me that I did. I really didnt want to but to make her happy I decided to be a team player and I took of my shirt and slipped on her nightie. I figured at least one of us would be entertained, little did I know, we both were very entertained. She laughed and told me that you dont wear pants with nighties, and she undid my pants and pulled my pants down quickly, and my boxers went down with them. She laughed when she saw my little cock poking out of her pretty pink nightie. Her laughing turned me on for some strange reason, and I was enjoying the moment. My friend told me that she has a matching lacey thong that she thouht would look "adorable" on me. She grabbed a pink thong from her panty drawer and told me to slip into it. She held out the panties allowing me to step into them. Once my feet were in the holes, she slowly pulled them up until they encased my little cock. Little cock at first, almost instantly I was rock hard! She laughed and said she thouht I would like playing dress up. I couldnt argue, the proff was in her pretty pink thong! She insisted I wore some cute heels with her lingerie. She grabbed a pair and slid them on my feet, they were almost a perfect fit. I have smaller feet for a "man", but I guess my small feet match my small cock.
My friend had me walk up and down her hallway, having me pretend I was a model on a runway. I pranced up and down while she lauhed and teased me. The more she did so, the harder my little cock got!
I ended up playing dress up with her for hours, modeling lots of her sexy clothes. I wore dresses, camisoles and mini skirts, tight lady jeans, lots of bras and panties, female pjs, one and two piece bikinis, nightgowns, a pair of daisy dukes with a tube top, and lots of her footwear (high heels, sandals, flip flops, slippers, and womens boots).
I loved every second of this magical day. It really woke up my inner sissy gurl!! I was only sixteen at the time, and now Im twenty eight and I have really enjoyed crossdressing over the years. My female friend knew I enjoyed it, but not as much as I really do! I wish I could tell her but I fear it would ruin our friendship, and she would probably out me to everyone. I am strictly a closet crossdresser at the moment., but someday when the time is right, Id like to go out fully feminized and be more open about my gay, sissy side. Hopeully soon!! Kisses to all, Muah!! xoxo
You should bring this up sometime in conversation. Like remember that time you talked me into dressing and acting like a girl? I can't believe I did that. She will surely come back with something about how aroused it made you. This opens the door. You can respond that yeah, it was really hot for some reason. And say but that is kind of too kinkiy. Let her talk you into it again. She will probably realize you are open to it, since you brought it up.