Stories I thought I’d take to the grave Part III: Crossdressing

The aftermath of being molested by my friends dad brought some changes to my life. The first was dressing up in women’s clothing.

After being molested at age 11 by my friend Tony’s dad, I went through a lot of changes. The depression was a real kick in the ass. I hated him for doing that to me and I hated myself because I kind of liked it. In fact, the more I thought about it, the more I liked it. So when the “am I gay?” question came up, I had no idea what the answer was.

I was a pre-teen in the early 90’s and didn’t have access to pornography. The internet was not really a thing at the time so I did what I could. I would get sports magazines that were full of athletes with their shirts off. I would masturbate to that regularly. The real confusion set in when I realized I still liked girls as well. By the time I was 14 I had finally realized I was bisexual.

The first big change in my life after I was molested, was I had an obsession with my mother.. more precisely, her clothing.

As a child I would always eavesdrop on my parents having sex. I would press my ear against their bedroom door and listen. If they were in the living room, I got a show as well! So watching them have sex was my introduction to sex. Sigmond Frued said that every boy wants to make love to his mother. That’s not meant to be taken literally. I think he meant boys are attracted to women like their mother. Which is definitely true in my case. But also in my case, it was kind of true. Seeing my mom having sex so many times, I developed an attraction to her. She was a thin, athletic woman with perky breasts even into her late 50’s. It was easy to attracted to that when I had watched her have sex many many times.

One day when I was 13, I was home alone and I couldn’t hold back my urges anymore. I quietly crept into my mom’s room, even though I was alone I was still nervous I’d get caught. I started digging through her drawers and pulling out all the underwear and lingerie I liked and laying it out on her bed. I spent 3 hours in her room trying on everything she had. Even her daily clothes like jeans and shirts.

As I said she was toned and in shape, and I was a chubby little 13 year old boy. Surprisingly her clothes fit well. Everything but the jeans that is. My favorite was her bras. I already had chubby little boy boobs and my mom’s B cup bra fit perfectly.

I spent the entire summer between 8th and 9th grade at home wearing my mom’s clothes while she was at work. As soon as she’d leave for work, I’d run into her room and pick out bra and panties, and then an outfit I could wear. I’d wear it all day around the house, no matter what I was doing. Eating, playing video games, watching TV, I’d have her clothes on. I even began doing the housework, pretending I was my mom.

My friend Tony lived next door to me and on the other side of his house was another friend of mine. Her name was Megan. Megan was 2 years older than me, same as Tony, and if you saw her you’d think she was a lesbian. She was 6’ tall and a little overweight, but to mine and probably everyone else’s surprise, she was really into guys. Megan and Tony were having sex regularly. They were a walking stereotype; black guy and a big white girl.

Megan was incredibly nice and really easy to talk to and one night when I was 14 and she was 16, I told her about being molested. I didn’t say who did it or give any details though. She revealed that her stepfather had molested her as well and from that point on we were incredibly close.

After a year of dressing in my mom’s clothes, I went through a growth spurt and sprouted up to 6’2”. I also put on a bunch of weight as well and I couldn’t fit into my mom’s clothes anymore. At first I just tried to accept that that phase of my life was over. After just a few weeks though I couldn’t stop thinking about it.

One night while I was over at Megan’s house, she was on the phone with Tony and had left the room for a moment. I quickly ran over to her dresser and began rummaging through her underwear drawer. Unfortunately she returned a lot sooner than I had anticipated and she caught me with one of her bras in my hands and a pair of her panties in my pocket.

She was so mad at me but because she was such a nice person and we had become close over the last year, she gave me a chance to explain myself. I had 2 choices. Lie or tell the truth. In the 10 seconds I had to think, I realized the truth was going to be the only way I’d have a chance to get what I wanted. I told her everything about me dressing up and how I had grown and couldn’t fit into my mom’s clothes anymore and just needed something to wear.

Of course Megan being the kind person she is, completely understood and was so unbearably nice afterwards that my guilt grew stronger by the minute.

Megan was a tomboy through and through, and despite her being into guys, she didn’t dress like a girl. Her parents would always encourage her to do so but she just didn’t like it. She wore men’s boxer shorts and sports bras. When it was all over she sent me home with a grocery bag full of her bras and panties she was never going to wear.

A few days later I was over at her house again and she had come up with an idea to get me more clothes. Seeing as her and I had similar builds, we would go to clothes stores and she’d try on clothes I liked and if they fit her or were a little big, we bought them. Within a month I had spent my entire allowance savings on women’s clothes.

“So.. I’ve avoided this question for a while but, are you into boys then?” She asked while I was trying on clothes for her in her room.

“Both boys and girls actually.” I said out loud for the first time. “..although I’ve never been with either.” I added

“Really? Hmmm..” she replied drifting off a bit “..I shouldn’t say this but.. no, I shouldn’t.”

“What?” I asked curiously

“Well.. you know how Tony and I fool around? Sometimes he says and does things that make me think he’s into guys. I can’t really explain it but, maybe you could test the waters there.” Megan explained

I had spent the majority of the last year dressed up in my mom’s clothes masturbating while thinking of Tony. That I kept to myself though. Instead I played it cool or so I thought I did. What really happened is even though I denied it, she saw through me and knew I was into him.

“Subject change please.” I said embarrassed

“You look fucking hot in that outfit!” Megan said

“Thanks. I like it!” I answered

I had a B cup bra on that was white. Matching cotton white panties. I tight black shirt and an even tighter pair of jeans.

“Your ass looks great in those pants.” She said laughing “…so you’re into boys AND girls, right?”

“Yeah.” I mumbled back trying to catch a glance at my own ass in the mirror.

“Wanna fool around with me?” She asked

I turned around and Megan had already taken her shirt off. Even if I didn’t want to it would’ve been hard to say no after she removed her sports bra right in front of me.

“Interested?” She asked

I stood there staring at her breasts which were large B’s or small C’s. I wasn’t super attracted to Megan but she wasn’t ugly by any means and with her tits out she looked even better.

I was actually speechless. All I could do was nod my head. Megan took two steps forward and we were nose to nose. She started by giving me a quick peck on the lips. Followed by another ad another. Then she put her arms around me and her tongue in my mouth. We stood there making out for a few minutes. Finally, she took my new jeans and pulled them down to my ankles. She sat on her bed and pulled me closer. Then she wrapped her hand around my shaft and put it in her mouth. My head fell back and I let out a large breath of relief. Her warm mouth felt incredible on my dick. I watched her head bob back and forth and my cock slide in and out of her soft lips.

“Umm.. I’m going to cum!” I quietly mumbled

“Do it on my tits.” She mumbled back while pressing her breasts together.

I grabbed onto my cock and squeezed as I got into position. Then I shot a hot spurt of cum right between her tits. Then a second shot hit her chin and immediately dropped down on her hand. She grabbed my cock and squeezed out a few more drops. The she stood up and kissed me.

“Did I do a good job?” She asked nervously

“Are you kidding?! That felt incredible! I want more!” I said laughing quietly.

“Maybe tomorrow.” She said wiping the cum from her chest and putting her shirt on.

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