I've always been drawn to women's clothing, the fabric textures, the prints, the styles. As a teen I began dressing up in my older sister's clothes whenever I got the chance. At first I'd just look at myself but before long I began masturbating when dressed up. When I met my wife, now ex, my last year of college I put that part of myself aside, unsure how to tell her my about it, worried about how she might react. We married, had twins, a boy and a girl, got our degrees and made a happy family life together. When our kids went off to college we began to see cracks in our marriage, we had little besides the kids in common. Eventually we decided to part ways as friends, freeing each other before it could deteriorate into bitterness and war.

I moved into a condo a few miles from the house we'd shared, after a few months I began feeling that old draw toward women's clothing. About a year after the divorce I went on a business trip to LA. While there I bought an outfit. Slipping into it at my hotel was amazing. The feel of the pantyhose pressing my erect cock against my stomach was nearly enough to make me cum. Once fully dressed in my silk wrap around dress, pantyhose, heels, wig and makeup I spent hours masturbating again and again. The next evening, dressed again, I chanced a walk down the hall to the ice and vending machines, both hoping to meet another hotel guest and fearing it. By the end of the trip I'd gone out to eat, shopping and for several walks while dressed up. Most people didn't give me a second look and of those who did there were 2 reactions. The first was disapproval and the second thinly veiled interest. I'd planned to throw the clothes away in LA but couldn't, when I got home put then in the back of my closet. A few weeks later I was wearing them again but only at home. I was buying more outfits.

I'd been divorced 2 years when I met Stacy, 3 years my junior, a redhead with a fire personality to match Stacy and I hit it off. A couple weeks after we met I invited her to my place. Over dinner we talked revealing secrets about ourselves. I decided to take a chance and told her I dressed up in women's clothing, finding it sexually appealing. She didn't bolt for the door as I'd imagined she would instead she asked questions learning when the fetish started, how far I'd taken it etc. Over after dinner drinks she asked if I would dress up for her. Initially hesitant she reassured me and eventually I agreed.

I went to my bedroom and selected a mid-length black floral print dress with gold accents, paired it with nude pantyhose and 3 inch nude pumps. I selected a blonde bob cut wig and shaved and applied light makeup and active length false nails. Stepping back into the living room my knees shaking a little I hoped she'd like it. Drink in hand she circled me a couple times before I gathered the courage to look into her face. She gave me a small accepting smile. Moving back to the sofa we talked some more, my cock slowly becoming rigid as I relaxed and enjoyed her company, feeling more and more comfortable in my dress in front of her.

"Have you ever imagined, thought about having sex with someone while dressed up? She asked.

My voice trembled as I remembered back to the many times I'd imagined it and answered "Yes."

Taking my face in her hands she kissed me gently. When I tried to reach for her she pushed my hands to my lap and said "No, I'll guide you." Kissing me again she pushed me back on the couch and began sliding her hand up my leg and under my dress. Before long she was stroking my cock through my pantyhose and telling me how hot I was. It took all I had not to cream right then. She let me help her get her clothes off and felt her body. Pushing the pantyhose down to my thighs she straddled me right there on the sofa and guided my cock to her steaming wet pussy. Inch by inch sinking onto me as I moaned. I rocked my hips up as she circled hers the sensation amazing. She whispered into my ear the whole time asking me how it felt, telling me things she wanted to do to, with and for me, asking me to imagine them. When I came it was explosive, I moaned loudly and held myself deep inside her as pulse after pulse ripped through me. Cuddling on the couch our bodied intertwined I couldn't help but thank her. With a smile she replied "It's only the beginning."

In the past 3 years with Stacy she's expanded my ideas. I now dress most evenings, my wardrobe expanded to include negligees and other sexy pieces. I regularly use an at home lazer hair removal system and now grow very little body hair. We've bought many toys including strapons. I finally feel completely fulfilled sexually, there's nothing like being dressed in a sexy negligence soon your hands and knees feeling your girlfriends hands on your hips as she pushes as solid into your anus and tells you "Stroke yourself, but don't cum." The teasing, the torture and finally being allowed to release is spectacular.