[M] Confessions of a crossdresser…

I have been a secret crossdresser for over 20 years.

Nobody in my life knows this.

I live in a large, American city with fairly progressive friends. But I can’t imagine a situation where I can even “come out” to them. Crossdressing is misunderstood. Honestly, I can’t even pretend to understand what drives my obsession. I imagine most people stopped reading this after the first few lines–because even in a place that caters to a little of everything, it just seems weird to most. I get it.

There are people who will defend gay and trans rights who are judgmental toward crossdressers. “It’s just a fetish” is the typical response. Different than not comforming to the gender you were born.

And they’re probably right. But that doesn’t make it any more common among the fetish community. If you crossdress, you’re expected to be a sissy or a submissive. But I’m neither of those things. If anything, I’m dominant.

[mF] My mom’s friend has been borrowing me for housework. What will she do when she finds me trying on her panties?

**This story is true…up to the point of me getting discovered. That’s just fantasy…**

Mrs. Robinson was like a little sister to my mother. I wasn’t even sure how they’d first met, but she was always around when I was growing up. When I was in junior high she’d gotten married and bought a house just up the street from my family. Unfortunately, the guy had turned out to be a jackass and she’d caught him cheating on her–just after their first kid was born. She got to keep the house. And, of course, my mother felt it was her duty to offer the services of her teenage son to help out with the yard work.

The first time I went over I was just pissed off. As a kid about to finish high school I definitely felt there were better ways to spend my time. I hated my mom for volunteering me and I was just as mad at Mrs. Robinson for accepting the offer. Mostly i just mowed the lawn. But sometimes she had me to some handiwork around the house. “Man jobs” is what she called them. I knew it was her attempt to make me feel a little more grown up.

[Str8][mF] Wearing Auntie’s Panties

I was supposed to be home alone that day.

At least that was the plan.

It was the break between college semesters and I was staying near the beach with my uncle and his girlfriend, Pam. The plan had originally been to come down with a pal and spend the week blowing off steam before classes started back. A supervised vacation in the eyes of my parents–one where I couldn’t get into too much trouble since there was adult supervision.

But at the last minute my friend had to back out. I could have just stayed home, but instead I was excited. This presented me a different type of opportunity. I packed up my suitcase with swim trunks, jeans, t-shirts…and a week’s worth of panties. Some of them were purchase, but most were secretly pilfered from ex-girlfriends and relatives. I could hardly contain my erection on the drive down wearing pink, nylon panties beneath my shorts. I planned on indulging myself all week with my little stash.

But that changed the first night.

Taking a shower I glanced in the laundry basket and caught a glimpse of Pam’s panties. It wasn’t a tiny, uncomfortable thong or boring white granny panties. They were black satin with a red rose pattern.

[MF] Down By The River, New Orleans 2009

“You’re not to talk for the next five minute.”

Her big blue eyes widened.

“I can do that,” she said.

“I don’t believe you.”

She was nervous. And that was causing her to prattle on. I found it endearing. But she needed to be tested. I needed to see if she would comply. Or if it was all just a fantasy.

“Five minutes,” I repeated. “Not a sound.”

“We’re just going to stand here for five minutes?”

She glanced around. We were standing near the Mississippi in New Orleans. The sun was down. We were within site of Jackson Square, but away from the crowds.

“Starting now,” I said.

I took her hand in mine and we walked closer to the water. We stood at an overlook point. She stepped up and gripped the rail. She was wearing a lacy white dress with short sleeves and an asymetrical skirt. I stood behind her and leaned in so she could feel me weight.

She quickly turned. Her big blue eyes looked up at me. I kissed her for the first time. I could see the surprise on her face. She wasn’t expecting things to happen so quickly.

[MF] She Caught Me in Her Panties

Angela caught me red-handed.

It was December 1998 and I was home for the holidays. I went out drinking with a friend and when we got in his mom offered me the basement to sleep. She brought down some sheets and helped me pull out the sofa.

Before she’d even left I’d noticed the laundry room. I waited 20 minutes with my heart racing and my cock getting hard. Finally I didn’t hear any more footsteps above me.

I crept over to the washer and dryer. There was some stacked laundry on top. Socks. Sheets. Nothing exciting. I opened the dryer, trying hard not to make a sound. Inside was the mother load. It was all delicates. I was worried someone would come down the stairs. My heart was pounding. I quickly grabbed two pair of panties and shut the dryer. I scampered back out of the laundry room and over to my bed.

I had grabbed a black satin bikini style and black nylon full cut briefs with a floral print. The second pair looked more accommodating. I quickly shed my pants and underwear. I pulled the panties on. They hugged my hard cock. I climbed in bed and turned off the light. I closed my eyes and started touching my cock. I fantasized about someone else touching me.