A New Career, An Old Profession Ch. 03

Chapter 3 -- Not my usual client.

Life can change in an instant. Hanna and I had been together for six weeks, all was perfect until the call from her family. She had few relatives and her elderly aunt had taken ill and she'd gone to Florida to care for her. By now, a month had passed since I'd seen her and even the calls were getting fewer and further apart. With Hanna gone, I felt a little lonely and I'd stopped seeing lots of my old friends -- it was too complicated with my new work, plus there had been Hanna to explain too. The 'how did you two meet?' would require a complex and dishonest answer! There were certainly new challenges about this new life, and I cursed the fact that there was such a stigma attached to something that everyone needs and does that it had to be hidden.

A solid positive while I was missing Hanna was that work remained stable, I think that would be the way to describe it. So far, I'd been with men from their early twenties, right through to the seventies. I'd been fucked in every position you could imagine, and I think at some stage, most parts of my body had been splattered with semen. I'd started to feel like I had the job down, I was good at it and now, even had a few regular clients. In between work, I went to the gym almost every day and ran most days, so I was in the best shape of my life.

As always, with my new lifestyle, there was always a surprise and something new and unexpected right around the corner. Today the surprise was an email on my escort site from a woman, who called herself Jackie. Her message was simple, she wanted to know if I would accept an appointment with a female.

First off, this was unusual for more than just a woman contacting me but also the tone of the message. It was polite and formal and nothing like most of the messages which I would receive from men which would be straight to the point. I figured that I was Bi, that had never been an issue for me. I said on the site I was Bi, and it was a client and a new experience. I replied to Jackie and told her that I did take appointments from women and asked her how I could help her. I figured that it was quite unlikely that a woman would just want to pop round for an hour of pussy play, but you never know, I guess.

Jackie responded quite quickly and gave me a huge amount of information. She was 33, recently divorced, thought that she was Bi, or even lesbian and had fantasised about other women for years and years but was also shy and awkward and wanted to experience being with a woman in an easy way where there were no strings or complications and without having to go dating. She further explained that she didn't really enjoy sex with men anymore and had never orgasmed with a man, something she could only manage via masturbation. The point of her meeting was actually an experiment, she wanted to know for sure, if she would enjoy sex with a woman.

I thought about it for a while and this kind of client didn't really fit with the whole pop in for thirty minutes, or an hour and fuck me kind of arrangement that I was used to, and this was an entirely different situation which would require a little more careful handling than a horny man. I suggested to Jackie that she come for an evening, and I'd keep the entire time free, and we'd have no time limit so we could take things at her pace. In a short time, we agreed on the following evening at 9pm. To make the evening less weird, she asked to pay up front and did so using the escort site payment system. There was definitely something odd about accepting money from a woman for sex.

This all gave me some extra work to do the following day and I thought about how I could make this more feminine and less seedy. I wanted Jackie to be able to relax and so, I changed the bedding in the spare room with some I usually used on my bed which was far prettier than the basic sheets I used for the men and then added a small table and a floor lamp into the room and then, found some nice aromatherapy candles which had been lurking at the back of a closet and even moved a couple of plants into the room.

That evening, when the time came to get myself ready, I took extra effort with my hair and makeup. I went for a sexy black lace thong and bra but put on a knee length black dress, so I was cute and sexy, but less slutty than usual. I lit the candles, put the lamp on and waited for 9pm. It was actually just before nine when my buzzer rang out in my apartment, and I answered the intercom. A nervous, shaky, female voice, said. "Evening. Are you Cara?"

"Yes, are you Jackie?" I asked.

"Yes."

"Come on up, I'll see you shortly." I said and buzzed her in.

Pretty soon, I heard her footsteps clattering on the concrete stairs, and opened the door. I got my first look at Jackie who was a red head, with brown eyes, quite tall, large breasts and slim figure dressed in an ankle length, black skirt, deep red jumper and black coat with a small bag on her shoulder. She was perfectly made up but red faced as she entered my apartment.

"Hey Jackie, great to meet you." I said as she looked at me awkwardly.

"Thank you for agreeing to see me." She said. "I still can't believe I'm here!"

"I guess it's really strange for you to visit someone like me?" I said.

"The whole thing is strange, but I can't think of another way." She replied.

"I'm glad you chose me." I said

Jackie looked around and shrugged. "So, I'm not sure what the process is? Should I undress or ... how does this work?"

I smiled. "I have a nice and comfortable room ready for us to go to, or we can sit on the sofa for a bit, or, you can have a drink, or use the bathroom, we can take this entirely at your pace."

"I guess I'm really nervous. I don't think the small talk will help much." She said.

"I can understand that. Well, I think I can relax you, and I'll try my best. Why don't I show you into my room and I'll leave you to undress, maybe leave your underwear on for a while and we can see if my relaxation methods work for you."

Jackie nodded slowly. "OK." She said.

"This way." I said and led the way to the spare room.

Once inside, Jackie looked at around. "It's nice."

"I'll leave you alone for a few minutes, you can make yourself comfortable." I closed the door and waited outside.

Sitting on my sofa for a few minutes, I felt like I'd given her long enough then I knocked gently on the door and opened it slowly. Jackie was sitting on the chair, wearing just a pink lace bra and matching pink panties.

"Hey." I said as I closed the door behind me. "Are you OK?"

Jackie nodded.

"You look really pretty." I said with a smile.

Jackie smiled back, I could see she was unsure and nervous.

I walked over to her and turned my back. "Could you help me out and unzip my dress please? It's so hard to reach." Jackie pulled the zip down quickly and I felt my little dress get loose. Still with my back to her, I pulled my arms out of the straps and let it slide down my body to my feet. Stepping out of it as seductively as I could, I picked it up then walked slowly to the door and I could feel her eyes on my back. Hanging the dress up, I turned, and thanked her.

"You're a very pretty young woman." Jackie said.

"Thank you. That's so kind!" I replied and watched her blush and look away.

I didn't really have a solid plan on how best to help Jackie and she was more nervous that I was expecting so I wanted to be mindful of that but also help her get the experience she came for. I decided just to go with it and see what felt right in the moment, using my gut instinct, which for the most part had served me well so far on this crazy journey.

After standing with my hand on my hip for a moment, I walked back to Jackie and held out my hand, which she took, and I could feel how sweaty her palms were. With a little pull, she stood up right in front of me. Letting go of her hand, I put my hands loosely on her hips and bent my knee, so my thigh touched hers gently and looked at her and smiled, then kissed her shoulder.

"It's just us, we have all the time we need." I told her. "We don't have to rush or do anything you feel uncomfortable with. This is all about you and tonight is time for you to feel good and be looked after. I'll take good care of you."

I ran my hands up her sides and onto her shoulders.

"You feel so tense." I explained. "Would you like me to give your shoulders a massage?"

"That would be nice." Jackie said as she nodded. I felt this would be a great way to start touching her and hopefully, she'd settle into the moment and some of the nerves would disappear.

"Why don't you lay on the bed on your front?" I suggested. Jackie nodded and I moved away and watched her climb up onto the bed and lay on her front which gave me a nice view of her firm little butt with her thong nestled neatly between her mounds.

Once she was settled, I fetched a bottle of massage oil from the nightstand.

"Do you mind if I undo your bra strap and we pull your arms out? It's such a pretty bra and I don't want to get oil on it."

"Ok." She replied and I unclipped the hooks and she pulled the straps off and left the bra resting under her breasts on the bed.

Rubbing a little oil in my palms, I gently began to run my slippery hands over her shoulders and back, pushing firmly at the muscles which was a technique I'd picked up from having massages performed on me and also, knowing that guys like it when I do it to them.

"Does that feel OK?" I asked.

"It feels real nice." She replied.

I continued for several minutes, and I felt her tension falling away as she relaxed. I worked my hands lower down her back and covered her sides and arms before spending a long time on each leg. I even massaged her feet.

"Would you like to roll over now?" I asked.

Jackie rolled onto her back and pulled her bra away and dropped in onto the floor next to the bed. Her large breasts parted slightly and hung a little to the sides as her big, dark-pink nipples pointed upwards. While she was looking at me, I stood up, unclasped my own bra and pulled it off so she could see my breasts. Then I sat on the bed next to her and twisted around, put my slippery hands on her shoulders and again began massaging her body. After I'd massaged her arms and fingers, I went back her shoulders and this time, began slowly working down her chest.

"Is this, OK?" I asked as I reached the top of her right breast.

"Yes, you are so good at that." She replied.

Gently, I ran my oil covered hands over both her breasts, encircling them which made Jackie take a deep breath. Making sure I brushed her nipples gently; I massaged her big breasts until she was breathing heavily, and her nipples were hard. It was lovely to see her responding to my touch and it was clearly starting to arouse her. I spent a long time on her breasts and shoulders, by the time I was done, her big nipples were rock hard and glistening with their oily coating.

Continuing my work, taking my time and, if I'm honest, really enjoying having my hands on a woman's body, I massaged her belly and then the fronts of her legs, working my way up, allowing myself to get dangerously close to her panties and I could tell she was getting more turned on. Even though she was hardly speaking, her breathing was speeding up and sounded a little uneven.

"Jackie." I whispered. "Do you feel ready to let me take your panties off?"

She nodded quickly and lifted her butt as I pulled her thong off and down her thighs, before pulling it off her feet. I surveyed her perfectly trimmed triangle of short hair which adorned her pronounced pubic mound before I once again massaged her legs and thighs, this time, getting even nearer her labia. Jackie had her eyes closed and her chest rose and fell quickly. This time, as I ran my hands up her left leg, I lifted it and gently pushed it away, doing the same with her right leg until they were spread wide apart.

"You feel OK like that?" I asked.

Jackie nodded. I could now see her puffy, pink pussy lips which were glistening with her leaking juices. I was happy she was clearly aroused and intended to make the most of that but, for now, I decided to add more oil to my hands and then, as I rubbed up her thigh, I let my had cross the border to her soft pubic mound and, using my fingers, I massaged it, hearing a light moan from Jackie. Now, I was going to finally focus my attentions between her legs and see if I could give her what she clearly needed. I massaged the area next to her pussy lips slowly, working just two fingers up and down the soft skin at the very top of her thighs, and, finally, let my fingers brush across her labia, just once. She shuddered as my fingers made contact.

Repositioning myself, so I was next to her on the bed. I ran my right hand down over her belly, across her pubic mound and firmly over her clit and labia, cupping them in my hand. Jackie virtually lifted off the bed and groaned. I kept my hand in place, gently pressing my palm into her wet folds. I heard her groan as I applied a little pressure to my hand.

"You ready, Baby?" I asked her.

"Yeah." She said with a trembling voice and, with the gentlest of pressure, I rolled up two fingers and let them sink into her warm and wet pussy. Jackie arched her back and gasped as I slowly entered her, feeling her velvety, wet, warm pussy on my fingers. Now I began to slowly slide them in and out, rubbing her clit with my palm as I did, curling my fingers up to drag over her G spot with each, firm, slow pass.

The liquid sound my hand made was delightful as I slid my fingers deeply into her body, before withdrawing them, almost all the way, swirling around her entrance and sinking back in. Jackie had closed her eyes and moaned as I did my work. I saw her grip the bed sheet with her left hand briefly before she gingerly reached out and placed her had on my thigh.

"It's OK, you can touch me anywhere." I whispered. "Just feel every moment and do whatever you want to."

Jackie slid her hand around and massaged my butt cheek as her moans grew louder. I felt her pussy twitch inside, and she was writhing around on my fingers now, her head rolling. Leaning forward, I brushed my own breasts over hers as she got real close, then I took her right breast in my hand and, while working on her pussy, began to massage her breast, rolling her nipple around in my palm.

Her fingers began to grip my butt and I began pushing my hand tighter against her clit and I gently brought her over the edge easily and quickly. Remaining silent as I felt her start to climax, she thrashed her head around and started gasping loudly. In her pussy, she started a series of little muscle spasms which grew stronger as the seconds passed. She suddenly ran her hand up my back and pulled me tight to her as she fell silent, arched her back and went rigid as she came hard. Her pussy tightened on my fingers over and over and she finally let out a long groan through her gritted teeth as she began to tremble and spasm. I held my fingers still inside her deeply throughout her orgasm but as she came down, I kissed her forehead and let my fingers slowly slip out. I suddenly became aware that my own panties were soaked, a female client, it turned out, was a serious turn on.

"Oh, Fuck. That was even better than I ever imagined." She whimpered.

Stroking her body for a moment. I asked her. "How do you feel now?"

"Amazing. That was... wow...I never..." She replied and finally opened her eyes. "I can't believe you made me feel so good. I hope that one day I can touch a woman that well."

Standing up for a moment, I smiled at Jackie and slipped my thong down and stepped out of it. Jackie watched me as I took her hand, put one leg up on the bed next to her shoulder, then guided her hand between my legs, turning it and pressing it into my dripping pussy lips. "You made me feel good too." I told her.

Jackie froze for a moment, holding her hand in place.

"Do you like how it feels?" I asked.

"Yeah, you feel so wet and soft," She replied. "I never touched another woman before."

I reached between my legs and ran my hand over hers. "Go on, you can touch me, if you want to." I encouraged as I pressed her fingertips into my pussy.

We both moaned at the same moment as she slid two fingers inside my wet pussy.

"Ohh, Jackie, yes, that's nice." I assured her as her fingers reached inside me and I savoured the feeling of something other than a strange man's dick in my pussy.

"Can I ... I, urm ..." Jackie stuttered.

"Anything ... remember." I said.

"Taste you?" Jackie said.

"Oh, thank God, I thought you'd never ask." I said with a giggle, and I climbed on the bed as Jackie got onto her knees. No sooner than I'd lay back and opened my legs, Jackie had positioned herself between them. Reaching down, I used my fingers to spread my labia open so she could see my clit and my pussy. "It's all yours."

Jackie made a noise like she'd just tasted the world's most expensive chocolate as I felt her gently suck my clit for the first time. A sensation which ripped right through me. She may not be experienced with other women, but she knew how a clit worked and soon, I was grunting and moaning as she swirled her tongue around. I no time, she sank two fingers back into my pussy and began to finger fuck me firmly. It took around five minutes of delicious pleasure before I knew I'd cum. This would be my very first orgasm with a client and I had no intention of trying to hold it off. This, I was going to enjoy.

"Oh, Fuck, Yeah, you're gonna make me cum." I moaned, which seemed to make her speed up.

"I squirt sometimes, OK Baby?" I warned her as I rapidly approached the point of no return.

Jackie didn't stop but squeezed my thigh in a way that let me know she understood and with a really long, firm suck on my clit, I squealed out and felt myself start to cum. My back arched and every muscle tightened, and I shuddered as I began to enter the almost cramping paralysis that wouldn't release until I started to squirt. Jackie, pulled out her fingers, opened her mouth and pressed it into my cumming pussy. I literally, squirted in her mouth as I yelled out. She lifted her head up and she was soaked, but smiling and, for the first time, relaxed.

"Fuck! I can't believe you've never done that before!" I said as I rolled around, enjoying the post orgasm glow. Damn, she had gotten into that and had taken massive steps forward since her nervous faltering undressing to taking a mouthful of my squirt. I guess I'd done a good job.

"I always wanted to try that." Jackie said with a big grin.

I decided that when Jackie left, I'd make certain she'd remember me forever. Grabbing her hands and pulling her onto the bed, I rolled her over and dropped my head straight between her legs and pushed my tongue straight into her wet pussy which made her arch her back and squeal. Giving her long licks up her pussy lips, I settled on her clit and sucked it firmly while I sank two, then three fingers into her pussy and fucked her hard while sucking and licking her clit. As she grunted and wriggled, she grabbed my hand which was on her hip and I fucked her harder, slamming my fingers in deeply and dragging them outward over her G spot. It took only a couple of minutes, and she came again, harder than the first time. Her pussy clamped down on my fingers and she thrashed around on the bed, gripping my head between her thighs as she spasmed.

As she came down from the peak, I climbed up the bed, lay next to her and rolled her into my arms, holding her trembling body for a few minutes.

"Was that what you needed?" I asked.

"Oh yeah, it was exactly what I needed."

"How did it feel to orgasm with another woman?" I asked.

"Fulfilling! I always kinda knew but I now know my path for sure and I'll be forever grateful to you."