Chapter 2 - Hanna
One thing that was always in favour for working as call-girl was that it was always interesting and always different and, if I hadn't of set out on this journey, I would not have met Brittney which would have been sad, because she turned out to be a very cool addition to my life for a short while and the first person who would come to know me personally since I started sex work and so knew what I did for a living. In short, she became, for a while, the only person to really know me and see me for who I am.
I guess I'd been working for about seven, or maybe eight weeks, and it was a Friday morning when I logged into my escort site and checked my messages. This could be a frustrating process, because there would often be more than thirty messages but most of them would be asking for free pictures or video, asking for unprotected sex, anal, or something I didn't offer, all timewasters amongst which, there would be the odd genuine enquiry and maybe even one that would turn into an actual client visit. I came across a message from someone called Brittney which immediately stood out in my inbox. I mean, almost a couple of months in and this was the first time I'd seen a female name on that screen and so, I was immediately intrigued.
Brittney introduced herself as an escort, also working in Woodlawn and was the same age as me. She gave me a short bio about herself which said that she'd been an occasional escort for two months, and that she was a trans girl. I clicked on her profile, and you'd have never known that, unless you reached the naked images. She was a petite, with small breasts and, a small dick proudly on display in some of her pictures. Not what I was expecting at all. Brittney wanted to know if I was interesting in working any duo sessions with guys that wanted a trans and regular girl. She explained that she often had enquiries but didn't know anyone else, but she reached out to me as we were in the same area and a similar age. I'd not given any thought at all to the reality of working with anyone else at this point, let alone a trans girl but I decided to be polite and reply and keep all my options open. Once you started having sex with men for money, it wasn't any longer beyond the realms of possibility that you'd push your boundaries sooner or later and I accepted that. Plus, being honest, I was interested in getting to know a trans girl like this now the opportunity presented itself. There were two colleagues in my old job that I occasionally worked with, who were trans, but I didn't really know much about them, although we all got along well.
I soon started emailing with Brittney on most days and we seemed to be getting along just fine. We weren't really talking about the job, or anything, just regular stuff, about the city, life in Woodlawn and soon, we decided to meet in person at a bar near the end of my block and we settled for Tuesday afternoon, and I decided to start work later than usual that day. We lived only a few minutes' walk from each other.
I turned up at Benny's Bar at 2pm prompt, looked around and couldn't see Brittney and so ordered a beer and sat at booth at the far end. The bar was real quiet. Brittney finally arrived about ten minutes later and I watched her walk in, dressed in denim shorts, white sneakers and check shirt with her brown hair in a ponytail and a back bag slung over her shoulder. I watched the guys all check her out as she recognised me, waved at me and then ordered herself a beer. I laughed to myself that these guys would probably run a mile from her if they knew her secret but damn, as I looked at her, you'd really never know.
Getting to my feet as she approached, we hugged each other and sat.
"Great to meet you, Brittney." I said as we sat.
She immediately laughed. "Hey, you think we should keep the working names, or, you know, use the real ones?"
I stared for just a moment, and then burst out laughing. We'd been emailing via the escort site, and I was so into the zone, I'd totally forgotten to actually introduce myself, clearly, as she had too.
I stuck my hand out, which she took, and I shook it mock-formally. "Mel. It's nice to meet you."
"Hanna. She said as she smiled at me. You really don't look like a Cara!"
We spent a few hours in the bar that afternoon, just chatting and we got along real well. Surprisingly, the subject of joint working didn't come up until nearly the end.
"Look, I gotta split in a while." Hanna said. "I've got a client at 7 but what do y'all think about working together sometimes, you up for that?"
I stuttered a bit. "Yeah, I mean, sure, I'm so new to all this but why not, never done a duo before but yeah, I'll give it a try."
"I never arranged one but been booked to join other girls a couple times, it's OK and we seem to get along, but I would prefer it to be with someone I know and like. Let's hang out another time, you want that?"
I said I would, and we agreed to meet the next week.
Hanna actually emailed me after her client and, by then I was waiting for one of my own to turn up and after seeing to his needs, we ended up arranging to have coffee the following morning and then again, a couple of days later. I really liked Hanna and enjoyed her company and of course, she was the only person who knew my secret, so it was finally reassuring to be able to share that stuff with someone else. We began to discuss some of our clients and share some of the more funny and embarrassing moments.
Winter was ahead and the weather was cold, wet and stormy. I think the cold weather made the local men seek out hotter fun and I had an extra client or two that week. I was well into my stride and, other than the odd man who just couldn't get hard, most of the guys left happy and I found that I could get guys off easily. I'd never had guessed that I had that hidden skill. Planning to take the next day off, which was a Sunday, and probably the Monday too, I asked Hanna if she wanted to meet up and, I decided to invite her to my apartment and cook her dinner which she accepted on Monday evening.
By Monday afternoon, a storm hammered Chicago, the worst one of the year and, by the evening, lightning lit up the sky at regular intervals. The soup I'd made for dinner was ready and, right on time, Hanna showed up, and I took her long coat and hung it in the bathroom to dry off. I complimented Hanna on her appearance, she always looked pretty and tonight, her choice of ankle boots, black nylons, knee length black skirt and a multicoloured abstract shirt really worked well for her.
We ate, chatted, drank some wine and then more wine and the conversation turned to work. I was on the edge of being drunk and enjoying the feeling and felt suddenly very comfortable with Hanna, maybe even a little too comfortable and so I blurted out the question that had been nagging at me for some time.
"So, like, I've seen all your pictures on the site, right? A-and you've seen mine, right?"
Hanna leant on the table across from me, put her chin in her hands and raised her eyebrows and gave me a cheeky grin, clearly enjoying my obvious discomfort. "Hmm, hm."
"Right, so, you still got a, got a, ... You still got a dick, right?"
The smile crept further across her face. "Well, nothing gets past you, does it?"
"Right, so, I was wondering, like, when you're with a client, how do you, ... how, urm, ... do you fuck them, or do the guys fuck you, or both? ... Sorry, there it is, that's what I wanted to ask!"
Hanna giggled and sat back. "OK, so, I'm your first trans friend and so I'll share our secrets!" She said, between giggles. "For me, when I'm with a man, I am totally passive, that means, I never fuck a guy, if he wants sex, he fucks me. If I'm with a woman, then I'm much more active and I fuck women, use toys both ways, whatever works in the moment. That answer your question?"
