When I was a Junior in high school I had a girlfriend (Nicole) who pleasured me by giving me hand jobs with her panties. Eventually I opened up and confessed to her that I liked to dress up in my mother’s lingerie and jack off. She thought that sounded really kinky and a great deal of fun so she invited me over to her house when her parents were away. The thought of wearing Nicole’s delicates consumed me to distraction.
When I got to Nicole’s on the appointed day, she took my hand and led me into her parent’s bedroom and gently told me to get undressed. Suddenly I realized that I was going to be dressed up in her mother’s items and became extremely aroused. “Would you like me to dress you up in my mother’s clothes? You’re about her size and she has some lovely things I want to see you in. Go pick out some panties from the top drawer.” The selection in front of me was incredibly soft and feminine, much like my mother’s panties.
My hands were trembling as I selected a pair of pastel pink nylon briefs that had an ecru lace medallion on the front right side. “Those look cute. Let me put them on you,” she said. As she was pulling them up, I could see that she had arranged a bra, garter belt, nylons and a full slip on the bed.
She then proceeded to fit me into a white bra and filled the lacy cups with more of her mother’s panties… and then a pink satiny garter belt followed by a pair of the softest, sheerest white nylons I had ever seen or worn. The feeling was exquisitely cool to my skin and deeply arousing. Then Nicole had me raise my arms as she placed the slip over my head and shoulders. She pulled it down across my bra and torso and proceeded to straighten out the lace hem.
“Let’s take a look in the mirror. How does it feel to be wearing my mother’s clothes? Does it turn you on as much as your mother’s?”
“I’m in heaven. I have never had someone dress me up and see me like this… let alone in another woman’s lingerie… your mother’s lingerie! I don’t know how much longer I can stand it. Would you please jack me off?”
“Yes,” she said with a grin. “There’s just one more thing I want you to try on.”
“What’s that?” I asked.
“Have you ever worn a dress?” Nicole asked.
All I could utter was “Please don’t tell anyone about this.”