A New Career, An Old Profession Ch. 02

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?"

I nodded. "Yes, yes, but I have others!" I replied.

"Well, go on, ask away and I'll tell you." Hanna said.

"So, do you want to have the surgery and transition fully one day?

"Wow." Hanna said. "That's a great question! I dunno, maybe. I used to want that badly but right now, I feel happy with how I am."

"Good, OK, one more!" I said.

Hanna nodded. "It's your last one and then it's my turn!"

"So, when, like a guy fucks you, like, in your butt, doesn't it hurt?"

Hanna was silent for a moment and smiled. "Well, sure, if he is like King Kong, or not enough lube, or he forces it, but most of the time no, it feels good." She stuck her finger up in the air. "Wait, wait a minute." She said. "Are you telling me you never took one in the ass?"

I shook my head. "Never, always figured it would hurt."

"Wow, you work as a call-girl and you never even tried it, oh, that's so cute!" Hanna said. "I bet lots of guys ask for it!"

"Oh yeah, loads." I replied.

We spent the next drunken half an hour discussing the pros and cons of anal sex, like all good friends should. Finally, feeling tired from all the alcohol and chatting, we found a movie online and settled on the sofa next to each other and began watching a horror movie. Hanna slumped her head on my shoulder and together, we screamed and jumped through the first hour and finished all the wine.

Suddenly, out of nowhere, a massive clap of thunder overhead, shook the entire apartment and we both screamed, and then laughed at the real-life special effects. Hanna settled back on my shoulder, and I draped my arm around her. "I'll save you!" I joked.

With that, the apartment lit up blue and the lights, and TV went out.

"Fuck, this is bullshit!" I said, annoyed at the power outage which was now affecting our movie night.

"Shh, shh!" Hanna said, urgently. "You hear that?"

"Hear what?" I said, in the eerie silence and darkness.

There was a pause of a few seconds before I felt something clamp around my thigh and Hanna yelled, "THIS!" right in my ear.

Felling like I lifted three goddam feet off the sofa at the same time as letting out a squeal, I understood the prank.

"Oh, you fucking bitch!" I laughed. "I nearly fucking pissed myself!"

"Pussy!" Hanna replied and we laughed, still very drunk.

"Well, what the fuck shall we do now?" I asked.

Hanna shuffled around next to me in the dark. "What do you want to do?"

"I dunno, I hadn't imagined ending our evening in the dark, and, I want to know, if the bimbo in the movie survives!" I said.

"Of course, she doesn't survive." Hanna said. "Which is a shame, cause she's hot."

"Oh yeah, I'd fuck her!" I giggled.

"Me first!" Hanna said.

There were a few seconds in the dark, where we were both silent and then, I felt Hanna's warm hand, gently touch my cheek. My initial reaction to that was to expect another prank, but instead, I felt her breath on my face.

"You know, it would be a shame if we let the power outage totally ruin our evening, don't you think?" Hanna whispered, her voice gentle and soothing.

You know those fleeting moment where you just stop logical thought because, right then, it all feels right? This was one of those very rare moments and I nodded.

Hanna rested her forehead on mine for a moment and then our lips touched, and I kissed her, slowly, taking her bottom lip between mine and holding it for a second or two. It felt so good and soon I found myself putting my hand on the back of her head, scrunching her pretty hair in my fingers as I allowed my mouth to open a little further as we kissed and Hanna gently, slipped her tongue into my mouth and kissed me deeply which sent shock waves rippling through me as we explored each other in a sensual and slowly intimate introduction.

Right then all I wanted was this woman. I didn't care that she was trans, or a friend, or a potential work colleague. I just wanted her.

As our kissing continued, she threw her leg over me and straddled my legs, almost sitting on my knees as our kissing became more urgent. I began to unbutton her shirt and, as soon as I reached the top, I pushed it off her shoulders and ran my hands down the smooth skin on her back until I reached her bra strap which I quickly unhooked. Hanna pulled away from my mouth and giggled as she pulled her bra off and threw it onto the floor somewhere in the dark and then thrust her tongue back into my mouth leaving me to grab her face for a bit and then run my hands down her neck, down her chest and over her small breasts. Hanna let out a delightful moan into my mouth as the palms of my hands brushed gently over her small, hard nipples.

Hannah moaned so much that she had to actually stop kissing me and rested her head on mine as I massaged her breasts, each time gently rolling her nipples between my finger and thumb. She grabbed my tee and lifted it up, Reluctantly, I let my hands leave her breasts for a moment and I lifted my arms up and sat forward allowing her to remove my top. Hanna then went right for my bra and in a split second was pulling it off my chest. Hanna stood up, grabbed my hands and pulled me up too. A flash of lightening lit her up allowing me a tantalising glance of her naked breasts. Reaching around, she unzipped my skirt and let it fall to the floor. I did the same pulling myself close to her and feeling her skirt fall to her feet.

Running my hands up and down her back as I pulled our bodies tightly together, I allowed my fingers to squeeze her ass cheek which was now exposed save for the back of her thong nestled in the gap. I also felt her dick press into my belly, bulging in her lace panties, an unusual and delightful sensation. Hanna explored my back too, gently running her nails down my bare skin which made me shiver. After giving me a deep kiss, she pushed me back down on the sofa and I parted my legs as she climbed on top of me and again, kissed me deeply for long, long minutes. The moment I felt her weight on me, her warm skin pressing against mine coupled with her tongue deep in my mouth, my arousal turned reached the liquid level and I felt my panties become wet in an instant.

Hanna dragged her sexy mouth away from mine and kissed my cheek and then licked around my ear which made me squirm with pleasure just before she drove me further by gently dragging her teeth down my neck at the same time as kissing me. My back arched and I groaned loudly as she took my breasts in her hand and kissed around them and between them until she kissed me right on the left nipple and then hungrily sucked it into her mouth. It caused another immediate flood between my legs, and I lay there, racked with pleasure as she worked her magic on my breasts.

Hanna was nowhere near done with me and she slithered downwards kissing my belly and my lower abdomen, sinking her teeth in occasionally as I whimpered in anticipation. She knelt up between my legs and grabbed my knees, pushing them further apart and I felt her slowly run her hands down my inner thighs and her right hand ran over my panties, sending another wave of pleasure through my body.

She giggled. "Oh, wow, you've really creamed those panties."

Grabbing the tiny waistband of my thong, Hanna pulled them down as I lifted my butt and then put my legs together so she could slide them off and there I was, naked. Before I could blink, Hanna's head was between my legs, and I felt her lips land straight on my clit.

"Fuck!" I muttered as my back arched.

Hanna began to give me, what was easily, the best mouth action of my fucking life. Her tongue slithered around my pussy lips, around my opening and then circled my clit, over and over, sometimes, she sucked on the hood of my clit driving me wild. I put one foot on the back of the sofa and the other on the floor, opening my legs as wide as I could.

"Oh, fuck, Hanna, fuck! That's so fucking good!"

She responded to my encouragement by slowly sliding two fingers into my pussy, opening it gently and then expertly seeking out my G Spot. Her fingers rubbed me in circles, and she settled her mouth over my clit and sucked hard. It took no more than a minute of squealing and grunting while Hanna worked her magic for me to feel the inevitable orgasm begin to build.

"Oh Jesus, you're making me cum." I almost shouted through gritted teeth as I tried to prolong this beautiful sensation.

As I felt the first tiny spasms start deep inside my pussy, I began to uncontrollably shake, and Hanna responded to this cue by pushing a third finger into my pussy and sucking my clit twice as hard. I began to cum immediately, my body shaking violently as my pussy spasmed. I was frozen in place, I felt rigid as the waves passed through me, I couldn't even breath and felt like passing out as the relief from the spasm came with a gush of liquid as I squirted harder than ever before, spraying my new lover on her neck and chest.

Hanna released my clit from her mouth and withdrew from my pussy. She gasped for air for a second or two and then let out one of those cute little giggles. "Damn, Mel, you squirt! That's so hot!"

I sat up, gasping. Grabbed Hanna's hands and spun her around, I got up as she lay on the sofa. Resting my hand on her thigh near the top of her stocking, and running it up to her belly, I leaned down and kissed her lips. "No one ever made me fucking cum like that. You are fucking amazing!" I told her.

Turned out Hanna had seriously sensitive nipples and she squirmed herself as I enjoyed a long, slow, sucking and nibbling session, loving every second of how it made her groan and whimper. Still kneeling beside the sofa, I kissed down her belly and reached her thong. I gently stroked her cock through the lace of her panties which were literally saturated with precum. Carefully lifting her panties away from her dick, I slid them down her thighs and soon, they were somewhere on the floor in the darkness.

Dutifully, Hanna opened her legs I ran my hand up her thigh and gently stroked her balls which were shaved perfectly smooth, she moaned as I ran my hand up and onto her dick, gently encircling it, and sliding my fist up and down, coating all her precum down the length of her shaft.

"Ohhh, Fuck, Mel!" She squealed as my warm lips slid over the end of her cock and I gently and slowly swirled my tongue around her pretty little swelling cock head. I sucked her gently for just a minute util I felt her hips bucking with her moans. I knew I could have made her cum, but I wanted more of this woman. I could have gone and got a condom, but I didn't want to, I wanted to feel this woman inside me for real. This would be the first time I ever had a bare dick inside me, and it just felt right.

Swinging my leg over her I straddled her. Her cock touched my right thigh as I leaned forward and held her face in my hands.

"I want you so much." I told her as I pushed back and felt her wet cock slip between my thighs. Moving up and down, she squirmed as I rubbed her cock along my pussy lips, coating us in each other's juices.

"I want this so bad." Hanna replied and I pressed my lips to hers and let my tongue slide into her mouth. As I gently pushed my butt back and down, her cock head hit the mark and she groaned into my mouth as she easily and slowly entered my warm pussy, and I sank myself down to take her all the way in, holding still, feeling the sensation of her bare dick reaching inside my wet tunnel.

Sliding myself up and down on her, felt like heaven as her cock slid in and out, rubbing on my pussy walls and hitting every perfect spot on the way in and out. Lovely squishy noises punctuated our combined moans as I rode her. She was getting even harder in me and suddenly, she rolled us over and I was again on my back. Opening my legs wider, I quickly felt her push in deeper and I welcomed the deeper penetration.

Hanna began to shake and gasp as she gently fucked me. I pulled her down, so she lay on top of me, and our sweaty bodies rubbed against each other as she rotated her hips into my body.