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.
