My Life of Leotards, Lingerie, and More

By Pacific Chris

The following is a true story, true in every way, except the names have been changed and the conversations have been paraphrased.

Part 1 – My First Leotard

I believe I was born to love leotards. Ever since I was a very small child, I have been fascinated by girls and women in leotards. I remember being about 4 years old and watching women in leotards on late-1970’s TV exercise shows, wishing I was one of them. In elementary school, the girls would sometimes do gymnastics during gym class while the boys where playing basketball, and I found myself unable to get my eyes off their pre-pubescent bodies in their little black leotards.

My parents both worked, and while my sister was considered old enough to be a “latchkey kid”, she wasn’t old enough to look after me too, and therefore I still needed to go to a babysitter after school for some time. This was a woman in her early 40s, and she used to do yoga in front of the PBS yoga show on TV, wearing a baby blue long-sleeved leotard and white tights. I would often watch her and the show. After a couple occurrences of this, she asked why I was doing that instead of playing, and I mumbled some non-descript answer. Some weeks later she asked the same question again, and I came clean and said I wanted to do it too. She said I could join her right then, it wasn’t a big deal. I said it wasn’t the same, I didn’t have a “yoga outfit”, pointing at what she was wearing.

“Oh, would you like an outfit like mine?” she asked.

“Yes, I really would. But I couldn’t ask my parents,” I replied. “My dad would beat me,” I lied. In truth my dad never beat me, but I wanted to garner a little sympathy from her. To this day, I’m surprised I thought of that ploy on the spot at that age.

It apparently worked, because she said she said she would get me an outfit as a gift, and then we could exercise together, and it would be our secret (I would use this “exercising together” more than once in my life). The next day after school, she took me to a dance apparel store. I was very nervous that she might embarrass me, but she didn’t; she politely dismissed any help from the saleslady when she approached. Instead, she went over and looked at some black leotards for me.

“What do you think about this one for you,” she asked as she held up a small black tank leotard.

“Well… it’s very nice, but I would really rather be dressed just like you,” I replied.

She gave a curious smile, then picked out a small baby-blue long-sleeved leotard and white tights. The leotard was almost the same style as hers, although it lacked the pinch-front of hers. She paid for it out of her own money, her gift to me.

She drove us back to her house, and she showed me how to put it on. From that time on, I did yoga side-by-side with her, three times a week, both in our matching outfits.

For those first few times, I kept my underwear on underneath. After a while, I started dressing myself, and I eventually put the tights and leotard on without any underwear. I have no idea if my small penis ever got erect, but if it did and she ever noticed, she never told me.

The outfit would stay at her house, and she would wash it regularly. On Tuesdays and Thursdays, she didn’t do yoga, but cleaned the house instead. For the first few of these days I stayed in my school clothes, but eventually I would miss getting to wear my blue leotard and tights while I played with my toys or watched TV. One cleaning day, I simply put on the outfit anyway, and that was that. After school became my leotard and tights time. I was such a happy little boy, with no real concept of what cross-dressing or anything else about sex was. I just loved wearing my leotard and tights.

This went on for about 18 months, but then my family moved to another city, and my days as a latchkey kid began. Before I left, my babysitter asked if I wanted to keep my outfit. I really wanted to, but I knew it would eventually be found, and it was starting to get too small anyway. Sadly, I wouldn’t wear another leotard for years.

Part 2 – My First Touch

One of my school friends, Dan, apparently had the same fascination. While many other boys our age went through the “girls are yucky” phase, we never seemed to. We always liked girls, and apparently we both liked them in their leotards (although at first, neither of us mentioned that to each other).

One day when we were about 10 or so, I was over at Dan’s house after school. We were both latchkey kids, so we always had a few hours every school day with no adults around. Dan had discovered the Sears catalog, and besides the usual bras and panties stuff, back in those days the catalog had a huge collection of leotards and tights. We were pouring over these pages, fascinated by the pictures of the women and girls in their skin-tight outfits. Of course, I secretly wanted to have the outfits for myself, so I could wear them. Then after a while, Dan let something slip.

“I wonder what it feels like to wear that?”

I was stunned to hear it. I wondered if he was serious. I kept my eyes down on the page, and didn’t react. He was quiet too, I think he realized what he had said. We kept looking at the pages for a while, then I said I had to go home for dinner.

All that night, I couldn’t get my mind off the pictures, nor what Dan said.

The next day after school, we headed to Dan’s again, too look at the catalog. There was less talking between us this time, and so I decided to break the ice.

“Dan, what did you mean when you said you wondered what it felt like to wear an outfit like that?”

“Well… I don’t know. It’s just that my cock gets hard when I look at these pictures, and I wonder what it feels like to wear them.”

“Is your cock hard now?”

“Yeah. You?”

“Yeah. Let me see yours, Dan.”

I can’t believe I said that, but I did. Dan blushed, but then he stood up and dropped his pants and underwear. There was his little dick sticking out, but since it was as small and hairless as mine, it looked pretty normal. He asked to see mine, and since he had been willing to drop his pants, I did the same. We stood there, facing each other, with our little dicks all hard.

Then Dan did something else I didn’t expect or even understand. He laid on his back on the carpet. He told me to go on all fours, facing his feet. I did this, and then I asked what to do now. He said we each stick our dicks in each other’s mouth, and suck. I didn’t understand this; I had never heard of it. Apparently, he had heard of a 69, but I hadn’t, and I didn’t want to. But before I could say no, I felt his warm mouth sucking on my little cock. Oh God, it felt incredible. I closed my eyes and just let him do that to be for a while, enjoying this amazing feeling, then he stopped for a second and said “What about me?”

I opened my eyes, looked down at his little penis, and with all the great feelings going on in my own, I gave in and started sucking. Not bad, actually. There we were, two 10 year olds sucking each other in a 69. Through mutual sucking, we both quickly discovered that you can suck TOO hard, so we quickly got pretty good at making the other feel fantastic. Orgasms at our age just simply didn’t happen, and there was no ejaculations which was probably a good thing; I would have been totally freaked out. But from that point on, we would meet almost every day after school for some 69’ing.

Sadly, less than a year later, his family moved to a different part of the city, and I never saw him for a long time. But I would see him again…

Part 3 – My First Toy

At that age, my dick was always hard, small though it was. I kept a small collection of department store catalogs with girls in leotards, tights, and bodysuits underneath my mattress. I would play around with my dick, but it never felt nearly as good as 69’ing, and the idea of an orgasm was still foreign to me at the time.

Then one day, I was bored and looking through my parents’ closets, just seeing what’s around. I came across my mom’s “beauty kit” that she had received as a Christmas present from my dad one year. It had this control unit, and you attached various things to it. Many were nail files, cuticle pushers, things like that. You turned on the thing, and it vibrated. But there were also little massage attachments of various types. The surface of each massage attachment was a little bigger than a quarter. Snap them on the control unit, and voila, a vibrating massager.

It didn’t take me long to figure out that it felt good to rub these massagers against the head of my dick, as I held the shaft of it with my free hand. It felt SOOOOOOOOOO good. I held it there as long as possible, and then as I built to a climax, I suddenly had to stop. Essentially, I had my first orgasms, but since I was pre-pubescent, there was no ejaculate and no over-the-top release. It felt great up until the climax, but there was no release.

I started using the massager every day after school. I eventually discovered that 2 of the 6 attachments felt the best, both basic small flat surfaces. One had a hard plastic surface, the other was rubbery. I also discovered that this massager had both 120V and 240V settings. While it might not be such a great idea to change those if you’re in Europe, in North America it was fine and I realized that I could get 2 “speeds” out of the massager. Some days I put it on the 240V setting (slower) with the hard tip, some days I put it on the 120V setting (faster) with the softer tip. Eventually, I realized that my mom never used the “beauty kit”, and I ended up hiding it in my bedroom for both day and late night use (but only on the 240V speed which was much quieter).

Over time, I realized that not only did my dick feel good with stimulation, but also my little ass. I was still someone sheltered in my exposure to some things, and the idea of anal sex (either with men or women) never occurred to me. But I did like to stick things in my butt. I started small, like fingers or smooth pens, and eventually moved on to bigger items, and discovered that I could use Vaseline to help with the insertion.

I don’t remember how I came across it, but somehow I came upon the idea to stick the neck of a bottle of Brut After-Shave in my ass. If you don’t know the Brut bottles, they have a long straight neck and a fat base (somewhat similar to a butt plug). My dad had both a large and a small bottle of Brut; they came in some gift pack that they sell at Christmas time. I started with the small bottle, and quickly worked my way up to the larger one (about 5” long and the thickness of an average dildo). Sticking that in my ass was GREAT, and the base meant it couldn’t slip in too far, but it wasn’t tapered like a butt plug so I had to hold it there or it would slip out while I squeezed my butt muscles during masturbation.

I realized that I could keep the bottle in my ass during masturbation if I lied flat. Not perfect, but it would do. Cleanup was a bit of a problem, and I eventually starting putting plastic food wrap on the bottle prior to insertion as a pseudo-condom (even though I had never heard of a condom at that point in my life). I masturbated every day, with something in my ass about one third of the time, and was very happy at that point in my life.

It was only to get better.