The Male Escort

I sat up higher as well, very surprised by this information. "You really told your daughter you're seeing an escort regularly? And she didn't freak out?"

"No, not at all. Believe me, I thought I'd get some sort of blowback about it, but she was very accepting. She had a few questions, mostly about the social side of us, but she also asked me a few sexual based questions. I was as honest with her as I could be without getting too deep into the details of what we do."

"It wasn't weird for you, talking about your sex life with your daughter?"

"Well, it could have been, but we really bonded over it. And then she confided something to me that could have been uncomfortable for her. She told me she's never had an orgasm when she sleeps with a man. Not once. Sex feels nice, oral and intercourse, but she's never even come close to a climax except on her own. And she's been sexually active since she was 17, She's very frustrated and worried it will negatively affect her relationship when she's ready to get married, that she won't connect well with her husband."

I had a sense of where this conversation was going, If I was right, this was going to be a very odd request. "Anita, what are you trying to say to me?"

"Paul...this is hard... would you be willing to meet with Kelly and, if you connect well together, would you be willing to go to bed with her and see what you could do to help her? From what else she said, she might have a problem just letting her nervousness go. You're the best lover I've ever known. I don't know if you could help her. But I think you have the best shot."

"Wow, I don't know how I feel about this. It's definitely something I never would have considered, having sex with the daughter of a woman I sleep with. Tell me, did you suggest this to her?"

"I did. I told her how patient you can be, how tender and caring. She's thinking it over. I know this is an odd request, Paul. I just want to help my daughter find her sexual self. But if you can't do it, maybe you know one of the other men you work with who could help her? I'd rather it be you, strange as that seems. I trust you."

She cuddled closer to my chest, and I kept my arm around her. "Maybe I should think this over as well before giving you an answer. I wouldn't want anything to screw up what works for us. So give me a few days to consider this?"

"Of course, Paul. There's no rush. Let me know when you're ready." With that, we settled in for the night. And then, morning sex.

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This was a conundrum. On the one hand, I had to think about, even in my line of work, how many men would be willing to have sex with both a mother and her daughter, though, thankfully, separately. But on the other hand, I wanted to keep Anita happy. Not only was she my best client by far, but she was also a very nice lady and we had a good relationship. I enjoyed seeing her almost weekly, traveling with her, and the cultural life we shared. And her appointments alone paid for me to now be living in a luxury apartment and I was putting a lot of money away for my future between her and the others. And to put it simply, I liked her.

When I picked up my check that week, I sat down with Diana, like I usually do, and while we talked about the week and a few other things, I brought up the subject of Anita's request. "Diana, have you ever heard of anything else like this before? I sure as hell haven't."

She leaned back in her chair and thought for a moment or two. "Paul, I've been doing this for more than ten years now, almost twelve, and I've heard all sorts of things. A few years back, one of my clients asked her regular escort to help take her daughter's virginity after she turned 18. She said she knew she could rely on him to treat her right and make it special for her. So this doesn't really surprise me, except for the fact that it's Anita. She's one of your most 'straight' clients. You know, nothing kinky. Just companionship and sex."

"Yes, and I like her. She's been very good to me over the years and she's never once been rude to me. I would really hate to lose her as a client. It's not just the money. I care about her as a person."

Diana smiled at me, a warm smile. After three years, we had our own close relationship. I never had issues with her about getting paid on time or correctly, she never let a client get inappropriate with any of her escorts. I never felt degraded by her. From what I heard around town, some other women in her line of work could be not so honest. "I would say do it, but only if you can do it without feeling wrong with it. You'd also have to let her and her daughter know that you might not be able to make it work. We don't know why she hasn't been able to have orgasms. There are more than a few women this is an issue for. And there are all sorts of reasons why. Each woman's story is different. So, you have to be upfront with them. It can't cause trouble for you and Anita."

"I understand. Thanks, Diana. I'll decide in a day or two, so I can tell Anita on Friday, our regular night together."

"Try to set up a lunch for the three of you, not on the clock, where you can all talk it over and make the decision together. Then you should get some time alone with the daughter to see if you get along and maybe she can give you information as to why she has trouble. It could be a trauma from her past. Or maybe she has a very different need to reach orgasm, not just regular sex. She might not feel comfortable saying it in front of her mother. Some fantasy she needs to get excited enough. That can be kind of hard to talk about in front of your parent.'

That Friday, when I saw Anita for our weekly 'date', I told her I was undecided, and we should get together with Kelly for a casual lunch to see if we had some chemistry. If we didn't get along at all, this wasn't going to work. Monday, Anita called me (she was one of the very few to whom I gave my private phone number) and we arranged for lunch on Wednesday.

She picked a quiet little cafe in the West Village (Greenwich Village) where we would be left alone to talk. Instead of my usual suit, I wore a Ralph Lauren long sleeve shirt with tan slacks, and the ladies were dressed equally casually. Kelly looked a lot like her mother, though her hair was almost jet black, and she wore it fashionably short and a little spikey. She was slender, even a little slight, with small breasts, but definitely attractive. We shook hands nervously; this was not exactly a typical meeting.

We ordered, including a drink each, and after some ice-breaking small talk and a light lunch, Anita got up and said "I think I'm going to leave the two of you alone to talk. I'm going to that little boutique on 4th Street and 6th Avenue. Come meet me there afterwards, Honey" she told Kelly. "Lunch is on me. Have a nice talk. Paul, I'll see you?" She said it simply. Kelly knew our relationship, but Anita didn't want to speak of it.

"Friday night. Thank you, Anita." I stood with her and kissed her cheek goodbye. Then I sat back down with Kelly to see if we could be comfortable together.

"Well, this is kind of weird" she said with a wry smile. "I guarantee none of my friends have ever been on this kind of set-up."

"No, probably not. It's a first for me as well. Would you like another drink?"

"Yeah, I think I need it to talk about this." We got a second drink each and we started by just talking about our lives. She was working at a fashion magazine as someone's administrative assistant, and she enjoyed her job and hoped to have a future in the industry. She was bright and personable, and we relaxed.

"Paul, do you mind telling me how you got into your line of work? You can tell me it's not my business. I can understand why you might not want to tell me." She leaned forward on her arms, and her body language told me she really did want to know, and it might make a difference towards her decision on whether we would go forward.

I explained my encounter with Hal three years before, how that led me to Diana, how at the time I planned to make enough money to go to graduate school, but now I wasn't so sure.

"Aside from moving into a much nicer apartment than the dump I was in, I don't live high on the hog. I travel a little when I take a week off, see friends and family, though I'm not all that close with anyone. I can't exactly talk about how I'm making a living with most people, right? I kind of miss having someone that I can be that direct with. I only talk to a very few people about any of my private life."

"Like my mother? You probably talk to her, correct?"

"Sure. I know her a long time now and she's been good to me. And she's a very nice lady. I think the world of her." I found it was easy to talk to Kelly, even about this. "Do you mind if we talk more about you, Kelly? It's really why we're here."

"I guess that's right." She lowered her voice and we started to get to the point of the afternoon. "I've never really been able to enjoy sex. I don't NOT enjoy it. It feels good, but there's not big build up and definitely no climax, at least as my friends have described. Damn, this really is weird to talk about. But I think knowing that you're so discreet makes it easier."

She was blushing, but she was opening up to me. I just sat and listened, maybe in a way no one listened to her before. "Kelly, are you able to have an orgasm when you masturbate?" I had to be direct with her.

She turned beet red, but she saw I was not judging her. I just was looking for insight into how I might be able to help her. "Yes. It's the only times I've ever orgasmed. Mom thinks maybe you could be the kind of lover who could help me, but I doubt it."

I smiled, a warm smile, not snide. "Why do you think that, Kelly? Not to brag about my bedroom skills, but I'm successful at my job, and that means I'm kind of in demand. I've heard just about every kind of fantasy, and I can usually work with just about anyone. I have a few things I won't do, like I won't do bondage. I can't let someone tie me up, in case they get beyond my comfort zone. Nothing scatological. There isn't enough money in the world for me to do that."

That made her chuckle, which also made me laugh with her. "It's good to have SOME limits!" she replied, and we were finding it easy communicating together. "OK, let me tell you what I think about when I masturbate. See if you can deal with it. I never told my mother. I think I'd sink through the floor if she knew."

"Kelly, your secrets are safe with me, whether this leads to something or not. I'll never tell a soul. That's a promise." I touched the back of her hand, and she decided she was safe with me.

"You know, at this age, most people don't really know what they want with sex. And the men all think they need to be in charge in bed, and honestly, that does nothing for me. I feel the need to be in charge. I even want it to be kind of rough. I don't want to be spanked; I want to spank my partner. I want to demand he do what I want when I want. When I think about it..." she closed her eyes briefly and I could see this really was her desire. And I knew what she was saying about younger men. When I was in my early 20s, I couldn't imagine I would have let a woman be in charge. We're programmed to dominate. If we're not really built that way, it usually doesn't come to us until we're in our 30s at least. Sometimes much later.

"How rough do you think you need to be? Is spanking it? Or do you think you need to really hurt your partner? Because I can do this if it's not too hardcore. I can't allow someone to mark my body or face or pull my hair so it gets torn from my head. I wouldn't like it, and it would affect my ability to work."

"I don't want to hurt someone. I'm not angry. At least I don't think so. But I've looked at some videos and I love the Mistress/Submissive roleplay." I could see it in her eyes; this really was what she needed.

I looked at her as she composed herself. I had to decide if I thought I could trust her to set limits and respect safe words. Even if I wasn't bound, we would have to set those boundaries.

"I think I can help you, Kelly. I haven't done this type of thing before, but I can study it and prepare for it. I've gotten good at that the last few years. Let me ask you, do you have any sort of costumes for this? Things like leather, heels, stockings. There are some things that will make it even better for you that you can buy in specialty shops. And if you wanted me to wear something, that can be arranged as well."

"No, I don't have anything like that. But I know what you're talking about. Does this mean we're going to do this? Could you do this with me?" She was fidgeting around, clearly aroused now. If I had suggested we go shopping right then, together, I'm sure she would have done it. But we needed to go slow. I needed to talk to Diana and figure out a price for my services.

"I can and I will, if it's really what you want. But I'm going to ask you something. I rarely try to talk a lady out of hiring me, but I want to suggest something to you. Have you thought about going through one of those 'underground' websites to find a man who is experienced with this kind of kink? Someone who would know how to do this from experience?"

"No, I wouldn't do that. At least not at this point. I would be afraid of meeting a man who is dangerous, who is looking for a woman to hurt. I need a man I know I can trust, and who will also be discreet. You couldn't tell anyone about this, not even my mother. I guess you have to tell your manager?"

"Yes, but you can trust her. She's silent about her clients, like a tomb. I'm going to give you my email, and you can text me if there's anything you want me to wear or any other special request. I would have to go shopping, and I'd have to charge you for it."

She smiled kind of shyly. "I figured that would be the case. You know money isn't an issue. So, are we going to do this, Paul? You're sure you're willing?"

"If you weren't Anita's daughter, I don't think I would. But you seem like someone I can trust to know the boundaries."

"Believe me, I have no intention or interest in hurting you. I don't think that's part of my fantasy. Besides, if I damaged you, mom would kill me." We laughed over that, but honestly, it was a bizarre thing to laugh about. The entire situation was a little bizarre. We parted with a handshake, and I saw a gleam in Kelly's eyes. Her mind was racing as she already was thinking about how she wanted to live this out. It was her best, safest opportunity and she wanted to do it right.

I also wanted to do it right, but I hadn't had years to think it over. It wasn't my desire. I'd never really even thought about it in a sexual manner. I'd seen porn on the theme, but it really didn't rock my boat. So, the challenge was going to be making it work for Kelly and getting enough of a sexual charge out of it myself so I could perform. She wanted the sexual part, not just the Dominatrix part; some women just want that. I was going to have to do some serious research.

Over the next week, I kept my other appointments, including with Anita. I had my days off, Monday and Tuesday, and on those days, I did a lot of searching on my computer. About costumes, about the psychology of this role, about what Kelly probably needed. She'd have to tell me specifically, but I wanted a general idea. So that week, I didn't have a lot of 'me' time. I talked to Diana just to let her know I was putting a lot of work into this so she could charge appropriately for my time. Maybe that sounds like of cold to some of you. But this was my job, and I was acting as a professional. Professionals get paid for their time. The other side of that is as a professional, I wanted this to be the best possible experience for my client.

Kelly called me ten days after we met. She told me what I should buy for myself, and she told me to bring her the bill directly. It was a way of keeping things as discreet as possible, so Diana wouldn't know what she craved. She wanted this to be as private as it could be. Not even her mother would know.

I went to her apartment on a Sunday with a small satchel, dressed like an upscale young man calling on her, dressed in sports jacket and slacks, no tie. Just like we were getting together for a romantic Sunday afternoon. I even brought a bottle of wine, kind of like a cover in case one of her neighbors saw me. Kelly was trying to cover her tracks as much as she could. I thought she was overdoing it, but it was her call.

She met me at the door dressed in a light pair of slacks and a shell, very expensive designers with Jimmy Choo shoes. She was beautiful, classy, and nervous. I could feel it in her handshake.

She offered me a drink and though it was something I usually didn't accept the first time I was with a new client, I accepted the offer this time. She wasn't the only one who was nervous. We each had a scotch on the rocks while we went over the ground rules for the occasion. She did have a request that went against what we had agreed to. "Paul, I know you said no restraints, but it would really help me if you wore these handcuffs." She took out a pair of steel cuffs, but she showed me that I would be able to let myself out of them with just a movement of my wrists. I took them and tried it out, finding them easy to release, so I agreed to wear them for her. She smiled, and I could see her excitement rising. "You have what I asked you to wear for me?"

"I do. Let me show you." I had a shopping bag with me with the items, a pair of tight black leather shorts and a matching vest as well as a collar with metal studs. All brand new and with receipts for her to reimburse me. These were not items I would have bought for myself otherwise.

Kelly then led me into the back bedroom where she had a queen-sized bed with metal slats on the headboard, which would be just right for the handcuffs. She excused herself to get ready in her room while I changed for her in that room. I stripped down and hung up my jacket and slacks and put on the leather items, with a black silk thong under the shorts. I looked like a real submissive, or at least I did to my eye. I sat on the bed, my stomach in knots while I waited for Kelly.

20 minutes later, she came into the room, and she was really dressed for the role of a Dominatrix. She was clad in PVC leather, almost head to toe. She wore a biker style cap with a brim and silver chain, a lace-up corset with holes cut out for her small but perfect breasts (with very light pink, very thick, stiff nipples), gloves that went past her elbows and Fuck Me (FM) boots with a four-inch heel that went up past her knees with black thigh high stockings. The only part not in leather were her panties, small and snug, maybe a size too small, in satin. She looked amazing in that outfit, and my cock was straining to find space to expand to full hard, but the space wasn't there.

I got right into my role. "Mistress, you are so beautiful." But that wasn't quite right.

"Slave, you are not to speak until you are given permission!" Kelly grabbed my face with her right hand, squeezing my cheeks with a sense of menace. "Do you understand?"

"Yes Mistress! I'm sorry. I was just overwhelmed with your beauty!"

"I'll let it slide this time! But don't forget your place!" She released me and walked around me while I looked down, not making eye contact. "Very nice, Slave. You obeyed my instructions just right." She ran her hands all over my body, my back and chest over the vest, then my ass and my thighs, and finally over my crotch. She could feel how taught the material was, especially with my erection trying to burst out. "Very nice..." Her voice had a guttural quality, a sign of her significant arousal. I peeked and saw her nipples thick and swollen. I wanted to wrap my lips around them and bite them softly.