Doing It While Crossdressed

There are two things that really get my motor revved up. One is swimming fully clothed. The other is crossdressing. And if I combine the two, it is a high octane erotic rush.

I discovered my wetlook fetish at a very young age. I was probably as young as 5 when witnessing someone getting thrown in with their clothes on made a very lasting impression on me. I was too young to be sexually aroused, but clearly, some of those erotic feelings were stirring inside me.

I was 8 or 9 when my older brother pushed me in the pool with my clothes on for my first personal wet experience. Of course, I was angry at my brother, but I could not help but feel that euphoric sensation of wet clothing being plastered against my body. The weightless feeling of the clothing flowing around me, and the heaviness I experienced as I got out of the water. As upset as I was, I was also turned on. Still, I was too young to really understand this was a sexually erotic experience, but it made enough of an impression that I would try it again, and again.

As I reached the age of 12, nature threw me yet another fetishistic curve. I became enamoured with women's clothing, particularly pantyhose. My first crossdressing experience involved trying on my mother's pantyhose. I was old enough to understand sexual arousal, and my initial experience wearing pantyhose was imprinted on my soul.

Soon after trying on pantyhose, I began to add other items of women's clothing. Panties, slips, bras, dresses, skirts, tops, high heels.

One of the interesting things about our kinks is when two fetishes collide. Indeed, it would not be long before I would crossdress and get wet. I've written about the shower in my bathroom. I tried wearing a number of things in that shower.

My mother had an box of old clothes she didn't wear any longer. There wasn't a whole lot in there of interest to me, but I did find a few things. One item was a pink sheath dress. It was something my mom or my sister had actually sewn for themselves to wear. I'm not sure why it ended up in the box, but I was glad it did. The dress was knee length, lined, and zipped up the back. I would just zip up the dress and pull it over my head and slide into it. I would wear it along with a pair of pantyhose and get into the shower. I enjoyed the sensation of the shower gradually soaking the dress and nylons. As an added bonus, the shower had a spray nozzle that could focus a strong stream of water in just the right places to induce ******. I did that a lot!

The bath tub was also a source of joy. I got in their crossdressed a number of times as well. I especially enjoyed lathering up, and re-submerging.

I should note that in both cases of the shower and the bath, I never wore shoes.

While getting in the tub and shower while crossdressed was fun, there was still one body of water left I had not yet experienced. Oh...I had been swimming in my boy clothes before, but not in women's clothing. I knew I would have to try it. And I told myself, when I did do it, I would be wearing shoes...women's shoes. This was a tall order. Mom did not exactly have a box of old heels she didn't wear. And there was no way I was going swimming in her good pumps. Then one day, I made an amazing discovery.

I was cleaning up some space in our loft over the garage, and was digging through some halloween costumes, when I found an old pair of slingbacks that probably belonged to my mother. They must have been up there for years. They were a tan or camel color, closed toe, and a short chunk heel. My heart began racing. I still remember taking off my shoes and socks, and slipping on these heels. I was 13 at this time, and my foot was actually about the same size as my mother's. Back then, I used to try on her shoes, and they fit well. With the realization of such a discovery, and my deviant imagination, I was practically breathless, weak kneed, and had something of a nauseated feeling in the pit of my stomach. I took the shoes off, put my own back on, climbed down from the loft, and put the shoes in the box with the old clothes.

I knew I was going to swim wearing these high heels. I needed to select an outfit to go with the shoes, and develop a plan for swimming in the pool.

In the clothes box was a brown/multi colored, plaid, a-line, knit skirt, with a knee length hem. It was fully lined. There was also a dark brown, ribbed cotton, long sleeve turtle neck sweater that went with the skirt. The sweater and skirt matched beautifully, and the shoes looked reasonably good with the clothes, but I wasn't going to find anythig better.  I had a pair of suntan L'eggs pantyhose - classic for the day - that I would wear with the outfit. I was all set with what I would wear.

I had to figure out a good day. My parents both worked. It was more of a Monday - Friday thing, but occasionally, they both would be working on a Saturday. As the days progressed, there came a Saturday in which both my mom and my dad would be away at work. My brothers and sisters were older - they were either in college, or had graduated and moved away. On that day, I would have the house to myself. There were risks of course. There was a pool service that came to the house periodically. A neighbor could come over, or look over the fence. It wasn't that unusual for someone to come to the house, and even stroll into the backyard unannounced. I decided to throw caution to the wind. It was fairly early - about 10:00 am - warm, but not yet hot, and I figured I was probably not going to be discovered.

I got dressed. I was in a tizzy really. I was so nervous, my hands were shaking trying to put on the pantyhose. My knees practically buckled under me as I stepped into the skirt, zipped it up, applied the hook, and re-positioned it on my hips. Next, I slid the sweater over the top of my head. Imagine, a long sleeve sweater and knit skirt in the middle of summer? I was already beginning to sweat from being nervous and hot. This was really an outfit for fall or even winter, and would have been more appropriate with boots. It was definitely out of place on a warm August day. Oh came the shoes. I slid on the first shoe, and pulled the sling over my heel. I then did the next shoe. I didn't wear any makeup back then - I was only into the clothes. And it was done...I was dressed.

I took a look at myself in the mirror. I felt kind of ridiculous. Part of me wanted to take all of those clothes off, and go play baseball or ride my bike. I had that really odd feeling in the pit of my stomach. But I persisted out of the bedroom. I grabbed some towels, and went outside. It was the first time I'd ever been outside wearing high heels, and they went click clack on the concrete aggregate patio. It sounded so loud. I was sure the neighbors could hear each step I took and and soon would be looking over the fence to see what was going on.

I stared at the pool. The water was pristine. My knees were wobbly. As I approached the water, I began to think about how I would do this. I hadn't planned out his part.  I mean, would I dive in, or jump, or walk down the steps slowly, or sit on the pool's edge, soaking the heels and then slide in gracefully?

My breathing accelrated. I'm sure I was really perspiring because I was so nervous. I always appreciated diving or jumping in because I enjoy that sensation of going from completely dry to becoming completely soaked. I decided to dive in. I walked over to the diving board. I lifted my skirt slightly as I stepped up onto the board, turned, and faced the pool. OMG...this was it. In my mind, I was practically hypervenhilating. I realized I probably couldn't just run to the end of the board and dive. Afterall, I had on high heels and was not particularly skilled at walking in them. So...I slowly stepped toward the edge of the diving board. My heart was pounding. I was incredibly aroused and quite obviously erect. I started to bend my knees to get some spring action into the diving board. As the board went up and down, the lined skirt was brushing against my nylon encased erection. I wasn't wearing panties...and the sensation was electrifying. Suddenly, I realized something I had not considered. My arousal was getting the best of me. I panicked...I started thinking about baseball, my homework, anything non-sexual, but it was no good. An ****** was coming on like a run away freight train. I wasn't ready to dive. I wasn't quite ready to get wet. I wanted more time, but just didn't have any.  So, without much more thought, I simply jumped. I launched myself straight up and out over the water. Everything was in slow motion. I could see the water below me. I was still dry, but the inevitable plunge under the water's surface awaited me. There was no going back. I reached the peak of my jump, and then began my descent toward the water. The water's surface was very smooth, and my perception of when I would hit was distorted. It seemed like I was falling forever. And then suddenly, I crashed through the water's surface and went under. My skirt was now inverted up around my shoulders. My heels touched down on the bottom of the pool, and the sensation of going from being completely dry to totally soaked had now engulfed me. was such an amazing feeling. And the sensation that had been building between my legs hit it's climax. Instead of thrusting myself back up to the water's surface, I just slowly began to kick to see how it would feel to swim with high heels on. As I did this, my ****** began and I released rope after rope of ***** into my pantyhose as the wet skirt caressed itself against my swollen member while I swam to the surface.

As I broke through the water's surface, I was gasping for air. Swimming with heels on isn't easy - you expend a lot of energy kicking, and it simply does not get you anywhere. I had to use my arms almost exclusively, with practically no strength to speak of. My ****** had drained almost all of my energy, and I struggled to get hold of the pool's edge.

I had done it. I had gone swimming dressed in women's clothing for the very first time ever.

I allowed myself to regain a bit of strength, and swam around a bit more. But post-orgasmic guilt and paranoia took hold. I quickly got out of the pool, wrapped myself in the towels, ran inside the house and got out of the wet clothes.

I would try swimiming in women's clothes a few more times, but this was probably the best wet experience of my life. I only wish I had been a little more mature and self assured to stay in the pool and enjoy it a little longer.

BizSuitStacy BizSuitStacy
56-60, T
2 Responses Sep 18, 2012

Great story,i´d like to be with you both swimming crossdressed and feeling water inside heels. Cheers!

Thank you!

Wonderful article Stacy, thank you for sharing.

My pleasure Sherry! Thank you for commenting!

You're most welcome Stacy.