The Chance Fantastic Pt. 03

Vivienne's Grotto wasn't really doing it for me anymore. The videos were still hot, and I had started to enjoy chatting with new visitors to the room the way Jennifer had chatted with me, giving them that subtle or not-so-subtle push to start their own journeys. So it was still enjoyable. But it had gone from a pulse-racing taboo experience to just a run-of-the-mill night viewing porn. It wasn't that exciting to be in a place where everyone thought like you, and acted like you. I wanted to stand out.

I started out searching for some webcam opportunities. Not to view them. That had never been my thing. But to maybe start my own webcam experience. I didn't really want to jump through hoops to set up an account, and besides, I didn't know how to make myself stand out against all of the prettier, more experienced performers. I needed a site that had an option to webcam, but whose main purpose was not to purvey streaming experiences. Which led me to my first hookup site.

From the little research I did, the hookup site I chose seemed to be a more legitimate one than the many other hookup sites that got advertised on porn websites. You could create a free account, which lowered the barrier of entry for me. And you could set up a quick stream via the chat function if you wanted.

I took my time and had some fun creating my account. I got all gussied up, applying my basic makeup and red lipstick. I stripped down to my pink lingerie, and I put on my b-cup breast forms. I even stepped into my heels so I could get a better image of my ass. I still looked like a guy playing dress-up, but it was no longer disgusting. For the more degenerate side of the internet, I looked cute and vulnerable. I could see what would be attractive about me and my newly pert ass.

I was not that experienced at taking photos of myself. I lacked all the equipment and know-how. The lighting was bad. I couldn't find a pose that emphasized my features how I wanted. I tried taking it from the right angles, but without a selfie stick or an easy-to-use mirror, I failed. It was also hard because I didn't want my face in the photo. I didn't actually have anything against posting a face photo - I mean, I put on all this makeup for a reason - but not as my main profile picture. I would lock face photos behind the wall so that only those that I accepted as friends could see them.

In the end, I settled for a fairly simple photo. I folded my legs underneath me and took a picture of my whole back half using the mirror. You could see the bottom of the back of my head, but that was it. It did a decent job of emphasizing my ass, which, now that I looked at it in the right light, had grown a bit, or at least firmed up a bit due to my workouts.

I took a few more - one, arching my back with one leg popped to give my ass that nice rounded look, one where you couldn't see my eyes, but you could see the dildo in my mouth, one of my small dick in its pantied cage, and finally, one of me splayed out on my bed, resting on my hands, with my chest thrust forward, where you could see my full face.

I wrote a description, explaining everything I had learned. That this was a recent foray into being a sissy, and that I loved being sexy for people. That I had never been with a guy, but that I was beginning to see why some people thought that was attractive. That I was mostly looking for online play, and that I still considered myself straight. I posted these photos, and started exploring the profiles of those people that got advertised to me.

I quickly learned the limits of the free version of the site. I could only visit certain profiles. I think there was a feature where a paid member could pay an additional fee that allowed free members to visit. I could only read certain emails - like the email I got from somebody that was clearly a bot, or the email from the person assigned to welcome me to the site. I also could only send out 5 chat invitations per day.

Getting a little disappointed, I fired up a stream, and posted a status saying that I would be online for a bit if anybody wanted to see me have fun with myself.

While I waited for someone to show up in my chat room, I saw a tab that said "members near me." I wasn't really interested in meeting up with anyone. But I was interested to see what other like-minded people were nearby. The state I was in was fairly conservative, so I imagined there were a bunch of people hiding behind online aliases nearby. And I was right.

There were clearly two camps of people: those who posted pictures, who either weren't so closeted or seemed to be of the more pathetic/desperate variety, and those who didn't post pictures. A lot of those who didn't post pictures had usernames that began with "rm_," which baffled me until I realized it meant "return missionary." I smiled to myself. Returned missionaries meant they were members of my church. It made me happy to see such hypocrisy on display. It meant I wasn't the only one.

A thought struck me. Wouldn't it be kind of fun to flirt with one of these RMs? I started scrolling through names. I used the filters to narrow the search to the people in my immediate area. Maybe I would recognize one. I then added a new filter, limiting it to people my age. On page three, something caught my eye. Someone had the username "rm_shymas." He had no picture, and, like me, he was a free member, which meant that I couldn't see his profile. But it had to be him. Who else would choose a username like shymas other than a certain Greg S. Hymas?

Reality hit me at that moment. I could be recognized by someone I knew. I quickly closed out of my stream (no one had joined, anyway), and then out of the website. I sat there for a bit, stunned. I had no idea what to do with this information. I mean, it probably didn't change anything.

I knew Greg had a pornography problem, and he probably made that profile a while ago, and then never checked it since all the good features were locked behind a paywall. But still. Greg and I were on the same hookup site together. Me, dressed as a woman and open to men. Him, as a male, looking for women. The thought scared and excited me.

I didn't even bother to finish masturbating that night. I took off my clothes, showered, washed off my makeup and the remains of the stuff that stuck the breast forms to my chest, and went to bed. Even as I tried desperately to think of something else, the thought of Greg finding my profile kept sneaking in. I should probably delete it. But then, what if he thought the girl in the pictures was hot? Indecisive, I spent the rest of a restless night dozing, waking up, getting excited, getting scared, and then dozing. But I never deleted my profile.