The Male Escort

I bent to pick up her skirt, but she stopped me. "Don't worry about that. We need to get undressed, Paul." I could sense her urgency, so I left the skirt alone and pulled her shell over her head and I saw her medium breasts in a black lace bra. The woman had incredible sexuality, no question. It was turning me on as much as her physical appearance. She really was a beautiful woman.

"Let me help you with this" I said as I undid her bra, and her tits were free. She had very little sagging and they had that slight banana shape, with very long nipples at the end. I kissed her neck and her shoulders, and she gasped as she reached for my pants and soon they were on the floor next to her skirt. My hands slid all over her back as hers glided over mine, and I pushed my hands down the back of her panties and her tits scraped along the hairs on my chest. She bit softly into my chest as I picked her up like she was a sack of feathers and carried her onto the bed. "I really do want you, Diana. I want us to have a great time together."

"I can feel how much you want me" she responded, referring to my now throbbing dick, at its full 8 inches, tenting out my boxers. "You are so wonderfully hard!"

"And you are incredibly wet!" She was, too. I could feel it in her panties, which were saturated around the crotch. We were grinding together as we kept kissing and licking each other, and I moved so I could suck on her breasts. I kissed them with great ardor, flicking her nipples with the tip of my tongue, and I felt her shudder as her pussy got wetter.

"Take me, Paul. Make me do what you want. I'm yours tonight." She was gasping like she was on the edge. She was like many powerful men and women. They were in command in their public lives and their work, but in private, and sexually, they needed to be submissive. Diana was no different. I understood what she wanted.

I got onto my knees on the bed, still in my shorts, and I told her "Take my cock out. Better yet, pull my shorts down. I want you to suck it. I want to watch you."

Her eyes looked up at me as she got on her own knees and leaned over, kissing my tummy, licking my torso, and I couldn't help but let out my own loud moans. She was so damn sexy, so hot. She pulled my shorts down to my thighs and grasped my pulsing cock, stroking it a few times, bringing up a large bead of precum, and she lapped it up like it was ambrosia. She kissed my dick all over and I thrust forward so the head pushed through her slightly parted lips.

Diana really knew her stuff. Her hands were all over my hips and my ass as she sucked me with skill and pleasure. I could tell this was something she enjoyed. Her tongue swirled around my head, making me groan, and I gently pushed her head down so her lips coated my shaft. The way she was using her tongue, I thought she might be testing me to see if I got too excited and would cum too soon. No worries there, though. I had excellent control of my body.

Diana kept on sucking my cock, giving me a great time as her mouth moved skillfully up and down, then along the shaft from the outside as her hand toyed with my balls. She really was checking my endurance, so I decided to change things up on her. She did say she wanted me to be in charge, after all. So I pulled back, leaving a strand of her saliva from her red lips to the head of my dick, and I flipped her on her back and kissed her lovely body all over, paying atten tion to her nipples again while my hand rubbed her inner thighs above the band of her stockings and then over her pussy, still in her black satin panties.

"Oh my God" she muttered as I kept suckling on her thick nubs, then I kissed my way down her almost flat tummy, all the way to the elastic of her panties. I personally get a charge from a lovely woman in sexy panties, and Diana fit the bill. I nibbled at her mound through the satin, then I slowly started to tug them down past her hips and then down her legs. She had her natural hair, a little darker in color than the hair on her head, and it was well groomed, as was everything else about her. "Please, do it, please..." she moaned as I took in her scent, musky with a touch of her perfume, and I started to lick her most sensitive region with considered probes. I licked slowly, savoring her pussy, which was already nice and wet before my tongue added my own moisture to the mix. My tongue alternated between flicking up and down her sweet slit, then I went back to her lips, slowing things down.

"Put a finger inside me" Diana gasped, and she whimpered as I pushed first one, then a second finger inside her eager pussy. "Oh, Paul, you're so good at this!" She was writhing on the bed, her stockinged legs rubbing on my back, spurring me on. I kept going down on her and fingering her until she almost shouted "Now! Enter me now!" She stuffed a condom in my hand and I rolled it on as quick as I could before pushing her legs apart and sliding into her well soaked pussy, going slow, but not too slow. She lifted her ass off the bed to get the best angle for her, and I moaned with her as her pussy, surprisingly snug, wrapped around my dick. When I was fully inside her I held still and ground my hips on hers, putting incredible pressure on her throbbing clit.

Diana gasped as she grabbed my shoulders and her nails dug in a little as she came with her eyes bulging open. My moves were steady and considered, taking my cues from her as to when she wanted me to speed up or do something different. She was the "client" after all, at least in this situation. She was making sure I had what it took to please the client and give her what she needed, not what I wanted.

"Faster, Paul. Make me cum again, and try to cum with me if you can" she said with an ethereal quality to her voice. I moved faster, enjoying myself as well as giving her the pleasure she craved, and soon I was almost there, but I tried to hold back until she was ready.

"Whenever you're ready, Diana. I'm there." She nodded her head briefly, and then tightened her legs around me as her pussy spasmed in her own climax, giving me my signal to cum, and I did, filling the condom with a thick load of semen. I didn't pull out, instead just resting on top of her while bearing most of my weight on my arms and knees. I kissed her softly, as her lover, since that was how we started. She had told me not all women want to be kissed by an escort; for some, it was too personal and they were only looking for the release from sex. Every woman is different, and I had to follow their leads.

After a few minutes my cock softened enough to ease out of her body, and then I turned to my side and stared at the lovely woman with me. The fact that she was older was of no consequence to me, The fact that she was about to be my employer was also insignificant in this situation. I enjoyed myself, and so did Diana. She had also warned me that it wouldn't always be so for me, but I always had to try to please the clients, in whatever way they wanted, with some restrictions.

"That was great, Paul" Diana said with a kind smile. "I think you'll do very well at this part of the job. And I'm pretty sure you'll do well as an escort as well. You have the brains and the charm. A little polishing and you'll be fine." She sat up and gave me a quick kiss before she excused herself to the bathroom. I laid back and thought to myself how Diana was a very different person in bed as opposed to the office, where she was strictly no nonsense.

When she came back, I used the bathroom and then we talked a little more. She told me how some of the women had fantasies they would want me to act out with them. "Some will want you to play a given role. Like men, women have all sorts of fantasies. Some may even want you to pretend to be their son's. They'll want you to call you 'mom' or even 'mommy'. Will that be a problem for you? You can be honest with me. That's not something every man can do." She looked at me hard.

"I don't think so. I'm not very close with my own mom, so I'm pretty sure I could do it. Whatever the lady wants, right?"

"Yes, except for the restraints. Don't let anyone get you in a position where you can't protect yourself, remember. Also, there are some women, and their husbands, who will want you to screw her while he watches, like a cuckold. People have all sorts of desires when it comes to sex. I'll usually be able to warn you in most cases about what the women like. They trust me with their secrets, and I keep them."

We went over a few more things before calling it a night around midnight. She sent me home by car service at her cost, and I plopped into my bed around 1AM, wiped out. The next few days would be very busy as I prepared to start my new career.

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The next day, at 11:30, I went to the haberdashery Diana had an arrangement with. She had told me to ask for Vincenzo, the owner, and though he was running a busy store, he waited on me personally, and, over the next three hours, we picked out material for 5 suits and 3 tuxedos as well as a dozen pairs of boxers and boxer/briefs, a dozen pairs of socks, ten button down shirts and a dozen ties, all conservative patterns. We chose four pairs of shoes, all Italian designers, and some jewelry pieces such as tie pins and clips, cuff links and even the cigarette lighter. We talked while we selected patterns and fabrics, and while he fitted me, he told me he always took care of the young men Diana sent personally. He clearly knew what was going on and he didn't seem to care either way about her business. He was making a lot of money through her, and he wasn't about to judge her.

At the end he told me he could have a tuxedo and three suits, plus all the extras in 5 days. and the rest within 2 weeks. The total bill almost made me gag; Diana might be paying it up front, but I'd be responsible for paying her back. Her 20K estimate was far off. At least she was letting me pay if off from my earnings, 50% of each weeks pay. It took a few weeks to fully pay it off. I would be available to start working the night I got the first of my new clothes.

The next few days were a bit nerve-wracking. I did a lot of studying online, brushing up on the music and art scenes, what was fashionable in current literature in New York as well as being up to date on local politics and Who's Who among the 'upper crust'. Diana called me the day before to make sure I was ready, and I assured her that I was. She promised to set me up with an 'easy' client for my first night, easy as in non-demanding. Then she gave me a name, a Mrs. Anita Forsythe, divorced, very rich with her own family fortune. She was 52 and when I looked her up online, her picture was of a woman who looked 5-10 years younger, a brunette with longish hair, a little overweight. Overall, I thought she was attractive, a woman I wouldn't have any trouble being able to function for and please her. Diana gave me a time and a corner, 5th Avenue and 53rd Street, to meet Anita. She'd pick me up there in her limousine. We were starting the evening at a fundraiser at the Metropolitan Museum of Art, dinner included. Definitely a tuxedo evening. She told me I didn't need to collect any money; Mrs. Forsythe had an account with her and paid her bill monthly. That actually made me more comfortable. I could, in my mind, just think of it as an evening out with an older woman.

I may have felt confident that day, a Wednesday, but as I dressed Thursday, I was scared stiff. Scared of not being actually smart enough to talk my way through the evening, not being charming enough to impress Mrs. Forsythe, and of being obviously a paid escort, though I assumed that was known being over 20 years younger. I knew it wasn't uncommon for women to have a paid escort for events, but she was also paying me for sex, and I was afraid that part would be obvious, like it was tattooed on my forehead. I thought about having a belt of whiskey, but I didn't think the client would be happy if I had even a hint of liquor on my breath before our date.

I left my apartment early, and I was at the right corner twenty minutes early, and Anita Forsythe picked me up promptly at ten minutes to 8. I climbed into the limo, and I was officially on the clock, starting my new 'career'.

"Hello, Mrs. Forsythe, I'm Paul, and I'll be your escort for the evening." I smiled with more confidence than I felt, and I shook her hand, not like I would with a man, but gentler though not with a limp wrist. I wanted her to know I was a man who knew how to behave with a lady.

"Hello, Paul. It's a pleasure to meet you." She greeted me with a radiant white smile with perfect teeth. She was more attractive than her picture led me to believe, and she wore a beautiful gold lame (pronounced 'Lam-A') gown.

"The pleasure is mine, Mrs. Forsythe." I was trying to be charming and respectful.

"Oh, please, don't call me "Mrs. Forsythe". It's Anita, please. Calling me Mrs. Forsythe will make me feel like an old woman."

"Anita, you're hardly an old woman. You're older than I am, but so are most women. You're actually a very lovely woman."

"My, aren't you the sweet talker. Don't worry, Paul, I'm still going to tip you tonight."

"Gee, and I was hoping to get stiffed at the end of the night."

"Ummm no, that's ME who's supposed to get stiffed!" And that broke the ice, a kind of silly joke that made us both laugh heartily. It let us both let our hair down, so to speak, and the rest of the evening we were completely at ease with each other, whether we were engaged in conversation or when I graciously asked her to dance a few times between courses. Anita was very pleased by my courtly manners, when I held the various doors and when I led when we danced.

And I also had a nice evening with her. She was very smart, well versed in art especially, we even talked a little about her ex-husband and her grown kids who never seemed to have time for her. I could see the hurt in her heart, and I took her hand and gently squeezed it. I didn't say anything on the subject, just offered her comfort in public, and I could tell she appreciated the supportive gesture.

I stuck to the guidelines Diana had given me: two drinks limit, don't talk too much about myself ("the ladies are looking for a man to listen to them and take interest") and to be kind, courteous and charming. That last part was especially easy from the way I was raised and from the fact that Anita was a kind woman. The gala at the Met went very well, she enjoyed showing off the handsome younger man on her arm to her friends.

Outside, we got into her limo (the driver of course held the doors for us) and in the back seat we kissed lightly. Nothing had been decided for afterwards in advance. The decision was totally hers.

She leaned forward a little and touched my knee. "Paul, I've had a lovely night, and if you're amenable, I'd like you to come to my penthouse with me. You're not obligated, and I would gladly use your services again for another night out. But if you'd like to come home with me...with this old lady...."

I clasped her hands in mine and hushed her there. "Anita, first of all, I had a great night as well. You're fun and funny, sweet and kind. And you're very bright. And....you really are a very attractive woman. You're far from an old woman. You're older, and that's all we'll say about this tonight. It would be a pleasure for me to escort you home and from there.... well, we can see what happens. I doubt you'll end up disappointed. And I know I won't be." I kissed her again, a more passionate kiss.

She looked up at me, making sure, in her own mind, this wasn't going to be some sort of pity fuck. It wouldn't be, not from me. I really did like her as a person, and she was a looker. Yes, I was getting paid for this, but I could see myself sleeping with her in different circumstances. I kind of have a thing for older women. My first sexual experience was with one of my mothers' good friends, something mom never knew about, and it was amazing.

She told her driver to take us home, and a few minutes later we were in the garage under her building, so she could enter her penthouse with more discretion. She even had a private elevator to whisk us up the 48 floors to the top, where she had the entire floor.

That penthouse was everything you can imagine. Floor-to-ceiling windows all around, in every room, with drapes that could be closed for privacy. The rooms were all huge, almost all bigger than my entire apartment. And they were decorated professionally in a classic yet comfortable style. There was no question whether she could afford Diana's prices. Anita was the definition of New York rich.

I helped her off with her wrap, and she asked if I wanted a drink with her. I told her I'd make the drinks and she sat down while I poured us each a short drink. We sat on the couch, taking in the view south from her windows, all the way to the lights of Lower Manhattan. She picked up a remote control and some soft music came from hidden speakers. She wanted sex, no question, and she wanted romantic sex. She wasn't looking for a man to dominate her or vice versa, no kinky fantasies. Diana had told me my first night would be an easy one, and she was right. Anita just wanted loving sex. She wanted to be desired.

After talking a little and after the alcohol helped us get rid of our nervousness, Anita, anticipating what was about to happen, said "Paul, you don't have to do this. I know I'm not young and beautiful, like the women your own age. I would be happy to have a man to hold me all night."

I felt bad for her, for her lack of confidence in herself. But I wasn't going to pity her. That would have been the worst way to treat her. "Anita, I know we don't have to do anything. I'd love holding you in my arms, if that's what you really want. But if you want more...I'd love that too. You say I don't have to do this. But what if I want to? I've already told you, I think you're a beautiful woman. I meant it before, and I mean it now." I leaned a little closer and I kissed her lips. She didn't move her lips for a moment, making her final decision. Then she leaned to me and we were joined in a great kiss, all authentic passion and heaps of desire. Anita didn't want to do anything considered kinky, no fantasy role play, she didn't want to be submissive or dominant, she just wanted to make love with a man, and I wanted her too.

After kissing for a while, and after our hands barely started to explore each other's bodies, Anita whispered "Paul, please take me to bed. I really need to be loved." There was a definite hunger in her eyes, and I kissed her over each eye.

I stood up and held out my hand, and Anita took it as she stood with me, both of us still dressed in our formal wear. "Gladly. Just show me the way." Leading me by the hand, she led me to the corridor which led to the bedrooms in the back, all three of them. We stepped into the master bedroom, and I closed the door behind us.

She was starting to get some doubts again, so I just walked to her with a smile I hoped was seductive. I took her face gently in my hands and kissed her deeply, and she let me probe her mouth with my tongue. Then her own tongue sought mine, and that was it, all doubts were gone, replaced by an overwhelming desire.

We kept kissing, over and over, getting hotter for each other with each kiss. Anita turned away an asked me to unzip her gown. I held her hair carefully away from the zipper and pulled the little metal tab down slowly, a sound that was very sensual under the circumstances. When I kissed the back of her neck and down her spine, Anita audibly gasped her approval. The gown was falling from her and I went to gather it to hang it up, but she said, breathlessly, "Never mind that, Paul. I don't care about the gown now!" She was wearing very expensive lingerie, nude bra and low brief panties in lace, under nude pantyhose. They gave her some control under the gown. I thought she was a damn sexy woman. and by then I had a very obvious erection which caught her eye.