The Male Escort

"You're really excited for me, aren't you" she said with a sense of wonder, like she didn't believe it was possible. But it was VERY possible. I really did want her.

"Anita, I'm incredibly excited to be with you. This is all me" I said, obvious in what I was referring to. "Why don't you sit on the bed and watch me."

She moved like she was on autopilot with her mind locked on something else, me. She sat and watched as I smiled at her, then I slowly disrobed in front of her. My bow tie, jacket, cufflinks.... all came off and I carefully piled them together. Her expensive gown may not have been a concern for her, but I hadn't even paid for that tux yet.

Then I was down to my pants, I dropped the suspenders from my shoulders, but then Anita said "Wait! Please come closer. Let me do that. I always loved taking down a man's pants. It just gets to me." Her eyes were bright and glowing, and her color was high, pink turning to a light shade of red.

I smiled at her and stopped what I was doing before I walked over to her. "Anything you want. I want to please you tonight, Anita." I was standing inches in front of her, and she looked up at me before kissing my flat stomach. A bunch of kisses both above and below my belly button, where there was a curl of thicker hair. I closed my eyes as I felt her fingers confidently unbutton my pants. As she helped pull them down, she kissed lower down, to where my Egyptian cotton black boxers began. Then the boxers started going down, and my cock sprung up like it was a Jack-in-the-Box, hard as steel.

"Oh my, Paul. That is some prize you have there!" She admired my cock, holding it lightly in her hand as she looked it over from all angles. "Very nice, indeed. But would you help me get out of my underthings? I love being undressed by a man."

I helped her to her feet and kissed her repeatedly as I reached behind her and unclasped the expensive lace bra, and her breasts were free. They were medium size, with some sag (She was in her 60s, after all), but they still had a nice shape and softness which I planned on getting to experience. But first I got on my knees and rolled her pantyhose down her tummy, then past her hips and down her legs, very carefully so as not to cause a rip or run. Then after I helped her step out of them, I covered her tummy with kisses, just like she had done to me. Her tummy wasn't flat, but she was hardly heavy. She was a mature woman, Parts of her showed her age but overall, she took good care of herself.

"Paul, that's incredible" she said with a voice that was drifting. "You've got me so excited, Please keep going. I think you know what I want." I did, and I tugged down her silk panties and I could smell her pussy. She was still able to create her own lubrication and I smelled so feminine. I eased her back onto the bed and pushed her so her legs were up in the air while I stayed there, kneeIing in front of her. I licked slowly on the back of her thighs, and I blew warm breath on on the lips of her pussy. I wanted to take my time and get her burning hot,

But Anita was already blazing. "Please taste me already! I've been needing this all night!" Whatever the lady wanted. I went at her pussy, licking all around her lips in a long oval, stopping at the top to flick her clit, which made her shudder and writhe. My fingers pulled her lips apart and I licked up and down her dripping clit before I went back to going around. I alternated my techniques as well as the speed, and soon Anita was planting her feet on the mattress and thrusting her hips up like she was trying to fuck my tongue. My hands slid under her ass and I held her while I sucked her stiff pearl, and she yelled "Oh, fuck! Don't stop!" as she came. More of her natural juices oozed on my face, especially my lips and chin, dripping down my neck. Anita was hardly an old woman, and she still knew how to enjoy sexuality. And I admit, I was kind of shocked when she said "fuck". She had been so proper during the evening and I just didn't expect it.

I stood up, my cock sticking out like it was seeking her, and Anita was very pleased. "You're still hard! I haven't done this in a while, but... would you like me to suck your penis? Just remember I haven't done this in a long time."

"I would love it if you did, Anita. I think there isn't a man alive who would tell you not to suck him. Do you want me to stand here or get on the bed?"

"Stand there, for a little while at least. It's been so long..." she said as she got down on her knees in front of me. I assumed she'd want to sit on the bed and blow me, but when she got on her knees it was a huge added turn on. She held me by the base and covered the head with kisses. Her tongue peeked out every so often and tasted the head, then the shaft, moving up and down along my dick from tip to base. Then she licked my balls, and I thought I was going to collapse from the bliss I was feeling. I gasped when she swirled her tongue all around the head and it pleased her so much that she sucked my cock into her mouth, hollowing her cheeks. I held her head in my hands to steady myself, not hurting her in any way, and I wondered how long it really could have been for her if she was this talented at giving head.

Up and down her lips moved, up and down, taking more of my length than I thought she would be able to accept. I didn't know when the last time was she gave a man a blowjob, but she was damned good at it. So good I had to think about other things so I didn't disappoint her. I had to tell myself I was actually getting paid for this.

All good things have to end sometimes, and after a while, Anita asked me to help her up and I did, just like a gentleman. She kissed me and I enthusiastically returned her passionate kiss. She backed up a couple of steps and I followed, and we fell onto her bed, still kissing and touching each other like a couple of randy teens. I sucked her nipples again and kissed her tits all over while rubbing her slit with my fingers. Anita in turn was stroking my cock with a skilled touch, better than most of the women my own age I had been with. I was ready when she was. I hoped it would be very soon.

Sure enough, after a few minutes she nuzzled my neck and softly said "I need you now, Paul. Don't make me wait any longer. I need you inside me. Please, don't be too gentle. I like a man to be a little aggressive."

"I'll be as gentle or aggressive as you want, Anita. I promise, we're both going to have a great time. I'm already having a great time." She smiled at me, a mix of appreciation and lust on her face. I reached for my pants, got a condom from my pocket, and Anita helped me roll it down my cock, kind of urgently. Then I moved between her spread legs, and I let her guide me right into her waiting, wet pussy.

She wasn't tight like a young woman, but she was hardly loose either. Actually, we fit pretty damn well together. When I was all the way inside her, I held still, ground my hips against hers, and made my cock flex a few times as I lifted on my arms to give her a little space. I was pressing on her clit against the base of my dick, and her fingers dug into my upper arms as waves of pleasure flowed through her.

"My God, this feels so good, Paul. Sooo good." Her legs were around my thighs, nice and tight. She obviously kept in shape; she may have had a little extra weight, but her muscles were toned and strong and she was able to hold me where she wanted me.

I kissed her a number of times as my butt started to rise and fall, quickly finding a pleasing rhythm for us both as if we'd been lovers for some time. Slow to start, but soon we were moving faster together. She lifted her body so she was meeting me almost every thrust. As her excitement grew, she moved her hands to my ass and squeezed my cheeks with a firm grip and her nails dug in a bit. The pain was also pleasurable, and it made my cock twitch involuntarily inside her warm, wet home.

"Paul, go faster. This is so good, but I need it a little harder, a little faster. I'm so close. So close." I bent my head and kissed her chest all over as I started to fuck her harder, thrusting deep and moving fast enough so my balls were slapping her ass. I grunted with each stroke, not from being tired but from my own desire. She kept encouraging me to go faster, and we were fucking hard. "Cum with me, Paul! I want to feel you!" I was close enough myself, and after a dozen more strokes, my cock throbbed as I let loose my own climax, filling the condom as I cried out, and Anita followed seconds later, actually squeezing me a little with her own inner muscles. Her climax kept going as long as I could maintain my erection. I eased. back a little, leaning lower to kiss her a few times, and she wrapped her arms around me, holding me close.

After a few minutes I rolled to the side as my cock slipped out from her pussy. Anita rolled with me, draping her arm across my body as she rested her head on my chest. We were both breathing harder than usual, but not uncomfortably so. Then her fingers started playing lazily with my chest hairs as I tickled her up and down her back, especially along her spine and she shivered in a very pleasant way.

She kissed my chest, tasting the light coating of sweat on my body. "You were wonderful, Paul. Really. You were the best lover I've had in a very long time. Better than any of the other young men Diana has sent me before. She told me this was your first time out as an escort. Is that really true?"

"I'm surprised she told you that, but yes, it's true. You're my first." I was a little uncomfortable talking about something so personal.

"Well, you are a very impressive young man. You were a very pleasant date at dinner, very capable at conversation and dancing. And you really gave this lady one of the best sexual experiences I've had since before I was married. Between us, my ex wasn't much of a lover. He thought he was, because he always enjoyed it. Me, not so much." She paused and looked up into my eyes. "Paul, I hate to talk about this like it's a business transaction, but let's face it, it is. This is a little uncomfortable to say... I agreed with Diana to have you for one, um, encounter tonight. But if you're not in a rush to leave, and you're able, I'd really like for us to have another go. I'm still kind of horny. You really got my juices flowing, and I'm feeling a little greedy. Of course, I'll pay you for your service."

"Anita, I had a great time with you as well. I'd love to be with you again. I know you'll do the right thing with Diana. Could you just give me a couple of minutes to use your bathroom first?"

"Of course. Better than going in my bed" she said with a chuckle. But could you use the one in the hall? I need to do the same, and my bathroom is kind of my personal space." I understood how she felt, and I did what I had to in the guest bathroom, and then we met back in bed, where we had a bawdier time. We were more familiar with each other that time, and the sex was a little more aggressive on both our parts, the language between us was saltier, and it felt like it was more about pure release sex as opposed to making love together. When I finally left at 3:30 in the morning (Anita paid for a car service for me), she handed me an extra thousand dollars as a tip. "Don't you tell Diana about that, Paul. It's for you alone. You were just amazing all night long. We kissed briefly as I finished getting dressed, not putting on the bow tie. She called for a Town Car for me, paid for on her account, and she asked me before I left if she could call on me again.

"I'd like that, Anita. I enjoyed this evening in every way. I'd be glad to be your escort any time you need one."

"And what if I just want you to come here for an evening or afternoon of just sex? Would that be acceptable?" She acted like my answer was no big deal to her, but I knew it was. I could see it in her eyes, where her smile didn't quite reach.

"Anita," I said, bringing her hand to my lips, "I would be glad to spend the time with you doing whatever you desire. We could go to a show or lunch or dinner. another gala, or, we could just stay in and have a very, very good time together." I kissed her hand before her lips and then I was on my way home.

I was pretty beat by the time I got to my apartment. I got undressed and carefully hung up my tux, then after brushing and washing up a bit I kind of fell onto my bed. I was tired enough to fall right asleep, but instead I was thinking. Thinking hard. This was my first experience as a 'pro', selling my sexual favors for money. The escort part, being Anita's 'date' for the evening at the party, was the relatively easy part for me. It just required me to be a gentleman and kind and charming as well as knowledgeable. That part came easy to me. The other part, the gigolo part, was my moral dilemma. For almost an hour I tossed it over in my mind. Should I keep doing this? There was a lot more money involved, but there was the old moral judgement regarding selling ones' sexual services. In the end, I decided I would keep doing this. Not all the women would be as attractive and as easy to be with as Anita was. She was charming and gracious, and we had a good chemistry. They wouldn't all be like that.

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That's my story of my first time working as an escort and a sex worker. Anita Forsythe was my first client, and for a while, she was requesting my services every week. Sometimes we went to parties and other social events, other times to dark, discreet restaurants before we ended up back at her penthouse. Other times, she'd request me just to come to her place for sex, often in the afternoon. I enjoyed spending time with her, but I had to be careful, as Diana warned me, about emotional attachment to a client. This was a work relationship, after all.

That first week, I saw three clients, and all went very well. One other just wanted sex, relatively straight sex, oral and intercourse. She was a nice lady of about 50, married, and she needed what her husband didn't or couldn't give her. The other, Catherine, wanted something different, something kinky. She was one of the women who had a fantasy about having sex with her 'son'. She wouldn't actually do that (her son was 22 and in graduate school out in California), but she did have a need to explore her fantasy. That didn't bother me at all. As a psych student, I knew people had all sorts of fantasies and most would never act on them in real life. So they needed someone to role play with them. It was something many men and women kept hidden from their spouses and even their friends, especially something that was so taboo. Diana had asked me in advance if I could go along with this kind of thing, and I told her I could. As long as I wasn't being hurt, I was capable of working with almost anyone.

Catherine had me come to her brownstone in the East 60s at 2PM on that Saturday, when her husband was out for the day. She was a stunning woman, late 40s, auburn hair, petite but very curvy with a slender waist and great tits. A real looker.

We sat and she offered me a drink. I asked for a club soda while she mixed herself a vodka martini, then we got down to getting to know each other a little. She had a great personality, vivacious with a great sense of humor, and we had a nice chat for about an hour, which put us both at ease. Then we got down to the reason I was there.

"So, Paul, I assume Diana gave you some idea why I hired you for the afternoon? Besides the obvious."

"Yes, she did. It's not a problem for me. I have a degree in psychology, and I understand people have various fantasies for various reasons. Sometimes it has to do with something they saw or experienced in their past. Whatever it is, most of us have them. I have my own, but that's not why I'm here. I'm here for your fantasy, Christine. You want to have sex with your son, so to speak."

She blushed and she said "Well, yes, kind of. I would never do such a thing, but the idea of it really gets me thinking. Do you want to know why, and what I want you to do?"

"Of course. I want to make this the best experience possible for you. So tell me what you want."

She gave me the details of where her fantasy came from and how she wanted to play it out. I nodded and told her that was fine. She smiled with relief, finally able to share her deepest secret with someone. (Diana knew the basics, but she didn't know any of the details). "Your 'props' are already in my son's old room. Give me about 20 minutes to change and be ready then. I won't come in earlier than that, but I[m not going to knock. I'll just enter as soon as I'm ready after that, so you should be ready then."

Catherine then showed me into her son's room, typical for a male of about 20. A full-size bed, a computer desk and chair set (no computer though), some sports and music memorabilia on the walls and the bookcase along with various textbooks and casual reading. It was familiar and different from my own old room back home. I used the bathroom attached and then sat and made myself as comfortable as I could sitting in the desk chair. The 'props' for me were a xxx-rated magazine, not softcore, and a pair of her panties, blue satin and very small. Very sexy. And I could tell they were worn recently and had her feminine odor. Catherine was really committed to doing this just as she wanted.

About 5 minutes before she was expected, I got out of my clothes except for my boxers, which I left around my knees. I picked up the magazine and checked out a few pages with a young man fucking a beautiful older woman, then I took my cock in my hand and stroked myself until I was fully hard, then I lightened up my stroke so I was going just hard enough to maintain my erection, rubbing it with her panties.

Less than 10 minutes later, I was still jerking my cock, nice and slow, reading the magazine, when 'Mom' just let herself into 'my' room. She was now wearing a medium length red silk robe, carrying some clothes in her arms. She quickly looked my way and acted like she was shocked to see me jerking off with the magazine and my 'mom's panties.

"Oh my, Paul! Wh-what are you doing? Are those MY panties?" She pretended to be both surprised and angry.

"MOM! Don't you knock? Can't a guy get a little privacy in his own room!" I was playing my part the way she described it. I hope I was getting it right.

"How can you talk to me about privacy when you're doing... that, with my panties! Those are the ones I wore yesterday! You had to go into my hamper to get your hands on those!" She looked even hotter with her cheeks turning red. "Talk about invading privacy!"

I then started to act sheepishly, like I was caught red-handed, which was what I was supposed to be. "Mom, I... um... dammit, you're right. I never should have done this, not with your underwear. I'm really sorry." Under normal circumstances, a young man busted like that would almost certainly have gone soft and covered himself up as soon as possible. But that wasn't part of the game. The game had me, as Catherine's son, staying hard and not trying to hide it at all. "I just couldn't help myself."

"What do you mean, Paul?" She was also not trying to avert her eyes; instead, she was eyeing my hard cock closely and her voice was trembling. She was really into this, so I kept playing my part.

"Mom, you're so beautiful, and I was very horny. And I have a thing for women's panties. I wanted to know what kinds you wear." I was smiling as my character took more and more control of the situation. Just like she told me she wanted.

"But-but those are my DIRTY panties! You could have taken clean ones at least!"

"But these smell like you, Mom. I wanted to know what you smell like. What your vagina smells like. It's a very sweet scent."