Becoming A Crossdresser Ch. 02

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First time dressed and being seen by someone else.
2.3k words
4.26
37.8k
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Part 2 of the 2 part series

Updated 09/22/2022
Created 08/26/2014
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So into the showers I went. Getting a little carried away, I brought a razor and some shaving cream to remove what little body hair I had, which in my case was not all that much. After rinsing off, I couldn't help but gently glide my hands over my now hairless body and enjoy the new sensations which could only be described as electric. So much so that it started to give me another hard on.

Well, I had to do something about it; I mean what kind of girl had that kind of bump down there. Even at my little size, it would be a dead giveaway, so I stepped out of the showers and grabbed a seat at the edge of the counter. To my surprise, the pressure from sitting down on the butt plug created yet another new sense of pleasure that I had never experienced before so I started to play around with it. Started by rocking around sideways, back and forth but nothing compared to when I started in a circular rotating pattern. That was heaven.

Using one hand to balance myself, I leaned back and spread my legs the way you see in porn when the girl is getting eaten out while sitting up on a ledge. With my free hand, I started to stroke myself gently while still grinding against the butt plug and counter. As I felt more and more comfortable in my position and movements, I sped up the stroking and grinding. As I sped up, I could feel the tension and the orgasm building quickly. Even after only cumming less than half an hour ago, I was ready to shoot again! That's never happened before, I was pretty much a one and done guy my whole life!

As I sensed my muscles tensing up and contracting in anticipation of the moment, I sped up the stroking even more; I was just so horny that I needed it really bad. It wasn't before long that every muscle in my body was contracting and releasing in waves of pleasure. I didn't shoot as big a load as the first time, but I was still able to coat most of my stomach in cum for the second time in just under an hour!

At this point I couldn't help but wonder to myself (and I know this sounds really silly), if I was ever going to be clean and cum free long enough to ever try on my new outfit, or if I was doomed to spending the rest of my life in the showers cleaning off cum and the smell of sex. This time in the showers I made sure to do nothing that would get me started again, and just rinsed off as fast as I could before coming back out and drying off.

As soon as I was dried off, I rushed into my room and went straight for the panties and bra. I slowly step into the panties and slid them up my legs, relishing the moment. As I got closer to my cock, I tried my best to tuck it and hide it.

Looking in the mirror, I noticed it wasn't the best job of tucking, but it would do for now and it wouldn't matter anyways. It was good enough that no one would notice, because of how well the boy short panties framed my ass. It was just perfect, just the right shape, and in perfect proportion to my legs and mid-section.

Now moving on to the bra and boy did it present some challenges (nothing that I haven't learned to get around now though). After I finally got it on (took me like 10 minutes, I know kind of sad), it just felt right. It didn't look right because I had no boobs to speak of, but it just felt so right, like it was meant to be, like I had finally found something that had been missing for my entire life.

Getting a little curious, with the butt plug still in (of course I relubed it to keep in nice and slippery), I made my way over to the mirror with hips swaying gently back and forth like any proper lady. At the end of the short trip across my room what I saw in the mirror surprised me a little bit. I mean of course I knew I would be nowhere near passable at this point, but I didn't expect what I saw.

Even with very little in terms of a transformation, I looked feminine. The push up bra gave me a little more cleavage than I thought it would, and the outfit gave me the look of a slightly flat chested early 20's female with a unisex haircut. Now this did nothing but make me rush back over to my dress, wig and breast forms so that I could try and complete the look and see how far this could go if I invested enough time and money into it.

Picking up my dress, I tried to remember the instructions I was given by the store keeper on how to put it on. I know it sounds silly, but remember , I had never put one on before and had no clue how up until that point. So I undid the zipper down the one side (the side without the shoulder strap) of the dress and slowly and carefully stepped into it. While sliding it up, I found I had to wiggle a bit to get it around my ass, but once I did get it by everything sat very nicely, which was important because I forgot the most important part! I hadn't put my breast forms into my bra yet! Well needless to say I grabbed those and slid them in as fast as I could so that I could get this dress on me right and proper.

Now as I pulled it closer to my shoulders, I slid my right arm through the one strap, and before zippering it up, I tried to make sure everything was where it was supposed to be and no wrinkles that would ruin the look. Happy with my work, I zippered it up and enjoyed the feeling of the fitted dress wrapping around my body for the first time. After letting the moment settle in for a minute, I took my wig and put it on the best I could and figured I could adjust it once I made it back over to the mirror if I needed to.

Walking over to the mirror, even in such a short distance, I couldn't help but enjoy how natural my hip swaying and sashaying had already become, and the feeling of wig brushing against my face and just beyond the tips of my shoulder on my sides and a little bit down below my neck on my back.

The only way that I could describe my reaction to the reflection that I saw in the mirror was stunned. Looking back at me was what appeared to be a cute girl in her early 20's with curves in all the right places. With a little bit of make-up applied in the correct places she could be a knock out and probably get a lot of boys in trouble as she was walking up and down the streets of campus and town. I remember standing there for 5 to 10 minutes, just soaking up the image and loving the way it made me feel physically and mentally. It was like I had found that long lost treasure, something was just so right about it and I was sure nothing in the world could ever make me give this up.

But unfortunately, I wouldn't be me if I didn't start to doubt if I really looked as passable and cute as I thought I did. I guess one thing that has plagued me my whole life was a bit of insecurity and a lack of self-confidence because of the way I looked. Even now when I looked like a really cute girl, I wasn't sure of myself.

So sitting there for a bit, I kind of pouted and thought about how I could build some confidence and eventually go out in public dressed like this. How could I expose myself to people as a female but maintain the ability to get away and never been seen again if things do go badly for some reason. I needed something that could give me complete anonymity but still put me face to face with other people.

Well it didn't take long for me to think of something thanks to the internet. I had my choice of any of those random cam to cam chat sites that I could use. It had the benefit of putting me pretty much face to face with a stranger but also gave me the sense of anonymity that I needed. The wonders of modern technology and all its benefits!

Well, grabbing a chair, I turned on my laptop and set up my webcam for my first foray into "public" and crossed my fingers hoping for the best. I logged into the site, and set up the web cam so that everything above the desk (from around chest height) would be in the shot and hit start.

And as fate would have it the first connection I got was two girls who looked like they were my age and they were hot. Both of them had that athletic build with just enough curve in all the right places to turn heads, especially in bikini season. I froze for a moment thinking I would be busted really fast and would get laughed out of the "room" but it didn't happen.

They waved hello, and I waved in response.

They didn't have a mic, but they typed over, "cute dress and I love the way you have your hair styled."

I responded, "thanks, I'm trying out a new look, glad to hear it looks good :)."

From there we made some small talk, I discovered they were entering their sophomore year of university at a small west coast school and I told them I was a freshman at an east coast school. We made some jokes how we could turn some heads and cause some "trouble" with the boys if the three of us went out together.

I discovered that both of them played for their schools varsity soccer team (which would explain their build). I told them I wasn't much into sports but did run a little bit so that I could at least keep in half decent shape. Well, as with anything on these sites, the conversations usually only last so long before people move on and that's what happened. We parted ways wishing each other good luck with our school years and in all the associated activities.

My next match was a little unfortunate so to speak. For those of you who've been on sites like these, I'm sure we all remember those idiots on their showing their cock and wanting some girl to watch them jerk. Well that's what I got next. At least it was big (I was guessing about 8 inches or so and looked pretty damn thick). However, for some reason I didn't click next like I thought I would (3 months later I knew why, but that's for a later story) and instead just sat there and watched.

I guess he took that as a sign that I was interested and he wrote over, "hey cutie, want to help me cum?"

I responded, "Sure honey, what do you want me to do?" (Again at the time I didn't know why I responded that way, but I sure do know.)

He responded, "Mmm why don't you stand up and give me a twirl?"

I stood up and did a slow twirl, and as I spun I looked over and noticed that he was starting to stroke himself faster. As I sat back down I gave him a playful wink.

To that he wrote, "Why don't you show me where you want my cum?"

Feeling ever more playful and now a bit horny myself, I leaned in close, opened my mouth and gave the most seductive lick around my lips I could. I must have done something right at that moment, because he started to cum shortly after.

As this was happening I wrote, "Mmm, that's it baby, cum for me, all over my mouth and face!"

He shot rope after rope of cum and didn't stop until he coated most of his hand and the shaft of his dick. After he finished he used his clean hand to type, "thanks, that was hot, you have a killer seductive look when you did that."

And that was the last message he sent to me before disconnecting. After that chat I hit the pause button to gather myself and think about what the hell just happened. I mean in a way I have always dreamed about being like that female porn star that all of the men want but I never thought that what just happened would happen.

I know it was a small sample size but did I really just pass as a girl and looked hot enough to get a guy off on camera? Did I really just do that? Did I really look that hot and seductive? Was this really happening to me?

After sitting there thinking for a while I got knocked back into reality when my phone alarm went off reminding me to call my parents. For now I would have to put these thoughts on hold, but I was excited with where this was going and how far it could possibly go.

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5 Comments
STUGPOLESTUGPOLEover 9 years ago
Enjoyed this

Please do continue

AnonymousAnonymousover 9 years ago

Ropes of cum is the right phrase people, good choice of words actually. So you go and tell them "learn to wright." Your the one who doesn't know your english buddy. Ropes refers to a shot that sticks together as it exits and makes a line, so it looks like little cum ropes. A liquid that has a stream in the air that is narrow but long can be called that. So go learn you english before getting on here and bothering other people with it, your probably a kid anyway.

jocrossjocrossover 9 years ago
liked this story

you are doing ok, although you may have to edit a bit (spools), but you are capturing the essence of it all

AnonymousAnonymousover 9 years ago
Interesting new theory!

So cum is now available in spools? It must be. You said there were "ropes" of cum!

Go learn to write and then come back and try again.

AnonymousAnonymousover 9 years ago

continue please

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