The Male Escort

I got a lot of requests to keep writing Paul Miller's story, so I'm going to honor those requests. Paul is going to find himself at a crossroads. He could stick with his career, a very well paid, and not unpleasant career, as a male escort/gigolo. But he finds one of his clients, Kelly, fulfills his own need for an emotional connection, something he tried to avoid in his work. Will forming a relationship with Kelly compromise his ability to have sex with the other women on a professional level? Will Kelly object to his career, since she knows what he does from the beginning? Or will he just continue his work while he is still young and handsome and in demand?

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Kelly was the daughter of Anita, my very first, and very best, client. Anita and I had an almost weekly appointment on Friday's, almost always to go to a gala of some sort or just dinner, and almost always followed by sex. She even took me with her on a vacation about two or three times a year for a week or so at a time, and she'd been my client for three years when she asked a very unusual request of me. She wanted me to have a session with Kelly, who, at 25, had never had an orgasm with a man. I agreed to meet Kelly, we connected well, and I agreed to play out her fantasy of her being a Dominatrix (for the details, see The Male Escort). Kelly had a pounding climax, and then we used a Hitachi vibrator together until we both came explosively. After that, we talked for a while and found we had a real personal connection, something I wasn't supposed to develop with any client, and something I found I was missing. It had been three years, since I started working as an escort, since I had a real personal relationship with a woman based on our mutual desires. It was very confusing for me. And now she wanted to make love with me. Heartfelt, tender, caring sex.

I should elaborate a little. The woman I worked for, Diana Royce, told me to avoid developing any real, deep connection with the women I 'escorted'. It wasn't an order, rather more of a warning, so as not to screw up my ability to do this line of work. I wasn't involved with anyone when I started and, much to my parent's chagrin, I never mentioned or introduced them to a woman as someone serious in my life during those last 3 years. I deliberately avoided getting involved with anyone, not even going on a date. And now here was a beautiful, petite woman my age (I was 28), and by talking, we were forming a connection closer than the one I had with her mother, who was in her mid 50s and whom I liked and knew very well by then. I felt that closeness after a single day, because I let myself open up to her in a way I never did with any client before.

"Well, Paul? What do you think? Do you think we could be real lovers?" Her eyes, doe-shaped, dark brown and curious, were locked on mine. The first move, if there was to be one, was up to me. "I'd like to see if we have the kind of chemistry to maybe have a personal relationship, beyond just sexual. I'm very attracted to you."

I looked back at Kelly with a distinct desire to satisfy a hunger I hadn't felt in three years. I crawled across the bed, and I ended up right in her arms, embracing and kissing. We were kissing in a way I never, ever kissed a client. This wasn't work; this was what I wanted, for me as well as for her. I couldn't even explain the way I was feeling. I barely knew this girl. It was only the second time we met and the first time we went to bed, and I felt an inner desire for her. Something personal.

We moaned as we gently rolled back and forth on the bed, from one side to the other. What remained of our clothes, mostly underwear, was gone in a few seconds as our bodies rubbed together in a very intimate manner. My fingers traced the line down her spine and her sleek nails lightly scraped me behind my neck and across my shoulders. We were sending each other direct signals. We craved each other.

"I want to taste you, Paul. I really didn't get that pleasure before. It's something I enjoy doing." Kelly said that between kisses on my lightly hairy chest.

I sighed as I said "I never would deprive you of that bliss, Kelly. Or myself, for that matter." I gave her a wink and a bit of a ball-busting grin.

"You're fun" she responded with a sexy smile that made her eyes glow. "Now, let's see if you taste as good as you look." Kelly kept kissing my tummy, teasing my Pleasure Trail, that very sensitive region from my belly button to my pubic hairline. Sensitive it was, and she blew softly on those very soft hairs. I squirmed beneath her as her hands lightly massaged my thighs, especially the inner part. Maybe she hadn't had powerful orgasms with a man before that day, but she had skills. Someone was patient with her and taught her a few things.

Kelly didn't rush things; she was teasing and fun. Her tongue moved lazily around the crown and head of my cock, then she moved down to my balls and sucked each one separately while she used her thumb on the glans. I was moaning involuntarily, and my hips kept lifting off the bed like I was trying to fuck her hand. She shifted again so she was sucking my shaft again while her fingers toyed with my balls. I tangled my fingers in her short hair (it was cut short, but it was thick and there was plenty to grab onto) and tugged a little, pulling her mouth up and down. My cock was shining from her saliva and my balls were getting wet as well. I could have cum like that, but I wanted Kelly. As my lover, and as my playmate.

I pulled my cock away from her mouth and she gave me a slight pout. "Why did you do that, Paul? I was having fun. And I would have loved to taste your cum. It's a turn on for me." Damn, she was so fucking sexy. Her eyes were shining like she had a real fire glowing inside.

"Maybe you can taste it when we finish, but I want you now. I want to make you cum from my cock, from the way I fuck you and kiss you." I moved so she was on her back and I was climbing on top of her. She showed no reluctance at all; she wanted this as well, to see if I could help her cum from more traditional sex. From making love.

Her thighs were apart for me, inviting me, and her feet were pointing to the ceiling. She grabbed my face and we kissed rapidly and with great heat as the tip of my cock met with her lower lips. We both shuddered as I eased into her pussy, slow and steady. I made sure the top of my shaft grazed along her clit so she felt every millimeter of me. Her body shook as I bottomed out, not an orgasm, but I knew from experience it was a very intense feeling for her.

"Paul, that's just wonderful!" Kelly exclaimed with her eyes wide open. "I might not need a climax if you can keep doing that to me!"

We kissed hard a couple of times as my hips moved from side to side. "Oh, no, Babe. You're going to enjoy this, every moment, just like I am. You feel great to me as well. We're both going to have such a great time."

I kissed along her neck and shoulder as I moved in and out, nice and slow to start. Her French tip nails lightly scraped the back of my neck as Kelly closed her eyes and focused on the great pleasure we both were experiencing. Her breathing was irregular and deep while mine was steadier as I made sure I was doing everything I could to please her. I kissed her breasts, sucking on her aroused nipples, and I grabbed her round ass tightly in both hands as my movements gradually picked up the pace.

Kelly grabbed my hair and pulled my mouth to hers for a deep, urgent kiss. Her legs wrapped around my buttocks, controlling how much I could pull back. My cock was soaked, her juices were dripping down her cheeks and the wetness caused my balls to make slapping sounds every time I lunged into her. I was grunting, looking down into her lovely face as I saw her features scrunch up. Then her eyes opened wide again and she urged me "Faster, Paul! Do it harder! Oh my god, oh fuck, I'm so close!" I rolled us over, so she was on top, and I pressed my thumb to her swollen clit, pressing hard like a sticking button. Kelly smiled broadly and flipped her head back, thrust her tits forward, and she cried out "It's happening! Oh fuck, Paul I'm cummingggggggg!" She screeched and thrust down hard to my hips as her muscles gripped my dick over and over, and it was only through the years of practice that I was able to keep from cumming right then. Her hips were moving in tight circles as she kept thrusting aggressively. I knew what she wanted, and I used my other hand to pinch her thick nipples, and Kelly came again, bathing my groin in warm moisture.

Kelly fell to my side, shaking a little as she came to grips with her first climaxes from fucking a man. I laid there, my dick still stiff like a board, and I smiled towards her as I stroked her legs, a soft touch that helped her mellow out. The way we were spread out, we almost filled the entire bed area.

When she settled down a little, I moved to her, getting behind her on our sides so I was spooning her. Kelly shifted back into the protection of my body and arms, making soft sounds of contentment. "You are an amazing man, Paul. I can't believe I finally came with a man, and it's thanks to you. You sexy man!" She turned to face me and cover my face with kisses.

"I helped you, Kelly, but trust me, it really was almost all you. I think I just made you feel comfortable and safe in a way you've never felt before with a man. I don't know why that is, but that would be my guess."

She didn't confirm or deny, she may not have been sure herself. She just snuggled against me before she noticed I was poking her tummy. "Paul, you didn't cum yet!" She reached down and grasped my cock, nice and gentle, making me moan in her ear. "Don't you need to get off, sweetie?" Her voice was so sweet and sexy at the same time.

"Very much" I croaked. I was blazing hot and beyond eager to cum.

"What can I do for you, Paul? I'll do almost anything you like. I want to feel you explode." Her words, her voice, were driving me to the next level of lust.

"Do you still want to taste my cum, Kelly? If you do... "

"Oh, I do, Paul. I want to taste YOUR cum. Sexy man." Kelly kissed down my body, moving quickly this time, eager to suck on my cock and drain me of my essence. Before I knew it, I was on my back and she was bobbing up and down my shaft, her eyes pointed towards my feet and her body just a few inches from mine. I touched her, her legs and thighs, caressing her ass, my hand wandering all over her slight curves. She sucked me hungrily, moving quickly but skillfully, and in mere minutes I arched my back, cried out softly, and burst like a river breaking through a dam. I was left limp and drained.

We stayed in each other's arms for a while, silent, comfortably so. It was peaceful and it felt natural. I was very drawn to Kelly, and I could sense she felt the same towards me, and it wasn't about sex. Well, not just about sex. After a while, we were hungry, actually famished, so we got up and cleaned up before calling a local fine Italian restaurant (in that neighborhood, almost every restaurant was a 'fine' one) and ordered in some baked clams, a salad and a delicious veal entree, all to share. And I paid, something I hadn't done with a woman in years. The business part of our date ended hours before. This was personal time, and Kelly was MY date. We talked easily all during dinner, discovering the little things you usually discuss on a date. We just had done things kind of backwards, having sex before the date part of the evening.

After we cleared away the dishes, it was time for me to get going. I hadn't planned on how things worked out, I had no clean clothes with me, no personal grooming items, so I wasn't prepared to spend the night. The next day, a Monday, was a day off for me and I had a bunch of things to do, and Kelly had to work the next day. As I dressed, Kelly sat on her bed and we had our first uncomfortable moments. Basically, we had to discuss where we went from there.

After talking around it for a few minutes, I decided to be more direct. "Kelly, I had a great time today. Both when we were on your time, and even more when we were just ourselves." I was dressed now, and I sat next to her and took her hand in mine. "As you know, I haven't had a personal relationship in years, and I think I'd really like to see you socially. But it's complicated."

"Complicated doesn't begin to describe things, Paul. Not only are you a gigolo, and I'm not trying to insult you when I say that, but your work times are mostly weekends, which is usually the only time I have to see someone. Friday night through Sunday. And then there's mom. Not only don't I have an idea what we would tell her, but how the hell do we have a relationship while you continue to see her most Fridays? Shit, I'm competing with my mother for a man. Not exactly something I would have ever imagined." Kelly tried to smile, but it didn't work. I didn't feel much like smiling either. "Besides, how do we have a relationship when you're 'working' all weekend long?"

"Kelly, sweetheart, I don't have a clue what to do here, either. This is a strange situation. I probably should have directed you to one of the other men who work for Mrs. Royce. But I'm glad I didn't, because I'm very happy I met you. But until we know where this is going, I'm not prepared to stop working. I have some very regular clients and I make a lot of money. I'm saving for my future. When I do decide to stop, I'll be able to do whatever I choose with my life. I originally planned to go back to school and become a psychologist, but now I'm not so sure. I think I'd rather find some sort of business to own, but I don't know what yet."

We were holding hands, feeling unsure about a number of things. "I don't like the idea of going behind my mother's back, especially when were finally getting along again after years of a distance between us. But I want to have some sort of relationship with you. Do you have regular clients on Sundays?"

"No, actually. Sundays I almost always have open if Diana has a new client or an existing client who asks for someone different. Sometimes I don't work on Sundays at all."

"If I asked you to stop working Sundays, to set it aside for us, would you do that?" Her pretty eyes searched mine, hoping for my acceptance.

"I could do that. I'd love to, actually. But then I'd have to work on Wednesday nights. Right now, I'm off Mondays, Tuesdays and Wednesdays. So to make up at least some of the difference, I'd probably work on Wednesdays. For now, will that work for you?"

"I guess so, Paul, but I don't know how I'll feel about this whole thing. I know you don't have emotional attachments to these women, but if we get close, if things develop for us, I don't know how I'd handle this. And that doesn't even count my mother into the equation."

I lifted her chin so I could kiss her soft lips. "I get the feeling if things develop well, if we become very close, I'd have to quit my job earlier than I planned. Much earlier. But we're getting ahead of ourselves. Let's take it one day at a time. We'll see what happens." I kissed her again, a deeper, sensual kiss. "Can I call you Tuesday night? Just to say hi?"

"I'd like that. I like YOU, Paul. I haven't felt like this about anyone in some time. I'd like to see if we have a possibility."

"So would I, Kelly. This is going to be a challenge. I can't say if this is going to be more than casual, not for now. But anything is possible. I'll call you Tuesday night. And I'll make sure I keep my Sundays clear." Kelly walked with me to her front door, and before opening it, we turned to each other and kissed a few times, a few short kisses and one longer, sexy kiss. "This was a pretty great day, Kelly. I'll talk to you Tuesday."

"I'll be looking forward to it. And I had a great time as well. You're very sweet, Paul, and very sexy." She playfully grabbed my ass, and I jumped a little, with a smile on my face. "Good night. Talk soon." With that I was in the hall and then taking the elevator to the street and on my way home.

On the train, I thought about Kelly, and about whether I was ready to change my life. Too soon to say, I said to myself. Way too soon to say.

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On Tuesday I called Kelly, about 8, and we had a nice chat. Friendly, no mention of Anita or other of my business. She didn't want to know, and as I've said, I don't talk about the women, in any aspect. One of the things I'm paid so well for is discretion. We talked for over an hour, nice and easy, and we confirmed plans for Sunday to meet early and start out bicycle riding in Central Park. We were both very physically fit and worked out regularly. I didn't ride often, but my legs were strong from swimming and using a step machine, and you could (and still can) rent e-bikes at various places in the city. After we rode, we'd keep our options open.

I told Diana Royce I needed to keep my Sundays to myself for the time to come, and I'd work on Wednesday nights instead. She didn't ask me why; I'd taken a Sunday here and there for personal reasons before. I'm sure she suspected why I wanted to stop working Sundays, that it involved a woman. She was certainly no dummy. I'm sure men came and went in terms of working for her many times over the years. No one can do that job indefinitely. You get older, you can't perform like you did in your 20s or 30s, your looks fade, and there's always younger men coming along. Sooner or later, the time comes to move on in life I knew I was one of her best employees over the years (she had raised my fee a year before due to how much I was in demand), no drama with her or her clients, though I was possibly about to change that. Kelly was the daughter of one of her clients, after all. And I had the brains, and now the means, to do something else with my life. Not all do.

On Wednesday she set me up with someone new, a woman named Jessica. An heiress of an old money family, she had been widowed for several years and had never used Diana's service before. One of her friends recommended Diana to her, and she had a very personal story that Diana shared with me, so I'd know what I was dealing with. It was kind of heartbreaking.

"Before you say yes to taking this job, you need to know a couple of things, Paul" Diana said as we sat down in her office that afternoon. "She's older than most of our clients (the typical age range was mid 30s to 60 or so, but there were exceptions). She's 72 and she told me she was happily married until 4 years ago when her husband died suddenly. She told me they had a good sex life together (Diana knew how to talk to clients and keep them from feeling embarrassed about hiring us), but when he died, she figured that part of her life was past. A few months ago, she was diagnosed with a fatal blood disease. She has time still and right now she feels good most days. But she knows her time is coming, and she wants to enjoy sex again before she's too sick to do so. Is that something that will bother you, Paul? Will you be able to give her whatever she needs?" Diana's eyes showed real empathy. I appreciated that about her.

I'm also a very empathetic person by nature. God knows why, since I didn't grow up in the most loving home. I must have gotten it from my grandmother, Frances, whom I was close to when she was alive. She made me appreciate the charms of older women as well. "I'm sure I can, Diana. I'm sorry she's sick, but it sounds like she's ok right now. I'll treat her right. You know me."

"I do. That's why I want you to take care of her. You're my best man. In three years, I've never had an issue with you. Never a complaint. I wish I could clone you." We smiled at each other. I appreciated the compliment; I also thought she was trying to make me forget about the possibility of leaving. We'd see.