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?
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
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.
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
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.
I went over to Jessica’s duplex on Central Park West right on time, dressed nice but casually since we weren’t going out. I had been told to come hungry; Jessica enjoyed cooking and before her husband died, they entertained and cooked for friends. I ate plenty of fine meals over the last few years, but not many were homemade.
After being let in by the doorman, I went to her apartment and I was greeted by a woman who looked about 70 and very well maintained. She was tall, about 5’7″, with nice curves, a little bit of a tummy, with medium length silver hair, nice and silky. There was no indication she was sick, not from looking at her. And she had a pretty face, age-lined, with a gentle smile.
We introduced ourselves and I sat in her kitchen while she cooked for me. She told me how she was the daughter of a family of one of the oldest families in New York, going back to the late 1600s. They invested in land, and she admitted without any bragging that her family was one of the wealthiest in the City.
“We’re famous in the high society circles, but we’re not well known otherwise, which is how we like things. Most of the old families don’t want to be known. We are charitable and busy with all manner of social causes. But we do most of it anonymously, or close to it. Unfortunately, having money can cause problems, especially when someone dies. My cousins and I have sued each other a few times. Money does give you great comforts and the ability to do good things and fun things. But it can also cause huge problems.”
She prepared this incredible Moroccan food, Couscous, lamb, fresh vegetables all in these amazing spices. And it wasn’t a heavy meal, which might have interfered with our plans for later on. Just delicious, with a nice bottle of wine. I did bring her flowers for her table since she cooked dinner for me. I couldn’t go empty handed.
After I helped her clear the table (I was raised with manners), we went into her living room, where the windows overlooked the park. We sat near each other on her couch with the rest of the wine, and we got to know each other more intimately. I said “Jessica, I know Diana told you she’d tell me some of your story unless you objected, so I know you’re sick. I’m very sorry. That must have been a terrible blow.” I moved a little closer to her and saw, in the low light of the room, there were a couple of tears in her blue eyes, but none were falling down her cheeks. “If you could tell me what you’re looking for tonight, whether it’s loving sex or something more aggressive, if you’re seeking affection…. whatever it is you desire, if you can share with me, I’d like to make this as wonderful an experience as possible for you.” I reached for her hand and held it in mine, with affection. I was careful not to hold her too firmly.
She crossed her legs, still fairly shapely, with a very expensive low-heeled pump on her feet. “I’ll be honest with you, Paul. I’ve loved sex right from the beginning, when I started dating. I loved being touched, and then I also loved it when a man used his mouth all over my body. And then, from the first time I had sex, it was amazing, I love everything about sex, in all manner of positions. My family was very conservative, as you might expect, but I rebelled. It was the 60s, I went to Woodstock and other concerts with various boyfriends, and I learned a lot about my sexuality. My husband Martin and I had a great sex life, passionate, sometimes kinky, even dirty. You might not believe it, but when we were deep in passion, I could talk up a blue streak, and my husband loved it when I did. Then he died four years ago, and I just assumed that part of my life was over. I was all right with it. But then I got this infuriating diagnosis. Right now, I still feel good, as good as I can expect. The doctors told me it will change within a few months and things will go downhill fairly quickly. When I thought things over, I realized I wanted to experience the pleasure of sex one more time. Maybe more than one time; I’m not sure. Anyways, I have a friend who I knew hires a man through Mrs. Royce. I’m sure you can put the rest together.” She wasn’t sarcastic or bitter, at least not in my company. Jessica just made her point.
“I’m glad you decided to do this, Jessica. And I’m very glad Diana asked me to be your date for the night. I like you; I think you’re a very nice lady, and I can see a very sensual side to you. I’m looking forward to exploring that aspect of your sexuality. I want to share all the lust and desire I can with you.” I kissed her hands, then I moved my lips up her right arm to her shoulder and her clavicle. I kissed the side of her neck, and before I went to her lips, I said “Jessica, would that be good for you? Would a mixture of lusty and loving sex be what appeals to you tonight? I’ll do anything you want. I’ll BE anyone you want. I want us both to have fun tonight.” With that I kissed her lips, soft and playful at first, a few times, and then our lips ground together and our tongues did their waltz as they got familiar.
“Take me upstairs, Paul. I want everything you spoke of. And more. I promise, I’ll be one of the most exciting lovers you’ll ever have. Maybe THE most exciting. It’s been a few years, but I think it will be just like getting back on a bicycle. Let’s go.” Jessica was practically dragging me behind her when she paused for a moment. “And Paul? Don’t try to treat me like some sickly creature. I’m plenty strong now, and I expect to have a wild night together.” Jessica continued to pull me along, up to the second floor, where the bedrooms and library were.
We entered her private bedroom and Jessica adjusted the lighting, so it was soft, all from recessed lights. No lamps. It gave the room a sexy glow. “I’m going to use my bathroom for a few minutes before we start. You can get comfortable if you like. But try to keep your underwear on. I like to be playful.” She smiled, a slightly nervous expression, and then she disappeared into her bathroom. I looked around the room. A king-sized bed dominated the room, with a few chairs, a large mirror behind the dresser, framed photos, expensive artworks, and a fireplace for the colder weather. All the furniture and furnishings were very classic and very expensive. The room, like the rest of her apartment, spoke to both her wealth and excellent taste. I folded my jacket and tie, then I took off my shirt, leaving me bare-chested. I slid off my shoes but stayed in my grey slacks. I wanted there to be some mystery.
I sat on the foot of her bed and a few minutes later, Jessica came out and stood still, shaking a little. I stood up and took in the sight of her, now out of her beautiful dress, just wearing a light pink peignoir with lace trim on the bottom, low cut to expose most of her breasts, but not all. Sure, they sagged, but I could also see their full shape. The material in most places was almost sheer, and I could see her legs were still lovely. I didn’t expect her to look young. She was who she was. And she was still a very attractive woman, even more so because of the person she was inside.
I stepped forward slowly, making sure she could see me taking her in, from head to toe. She kept eye contact with me, and I could see she was shivering now, as if she was cold. But she was shivering because she was excited. Very excited. A few inches in front of her, I stopped, and I smiled warmly. I touched her cheek, then ran my fingers lightly down her neck and down to her cleavage. “You’re a very sexy lady, Jessica. We’re going to have such a good time together.” I kissed her lips and she let out a soft moan as her arms went around my mid-back. Then she was kissing me, her tongue tracing my lips before I parted mine just enough for her tongue to tease its way inside my mouth. The woman could definitely kiss.
I felt her hands moving over my back and then down to my butt. She squeezed me with just the right amount of pressure. Not too hard, not in the beginning, but she was letting me know what she liked. My hands were exploring her from the back of her head, down her shoulders and back, and I also gave her butt a very firm squeeze.
Then I felt her skillfully undoing my belt, then the buttons of my pants. Before they fell down, her hand was over the front of my boxers, caressing my rapidly expanding cock and my heavy balls. She was touching me with confidence as well as experience, giving my cock a series of tender squeezes. In no time at all I was fully hard.
“My god, Paul” Jessica whispered in my ear. “You’re making me feel so desired. I might not even need my lubricant!”
“That’s because I do want you. No lie. You’re incredibly sexy, Jessica. Any man would want you.”
“Come on, Paul. I’m hardly young and beautiful. Don’t bullshit me, please. I don’t have the patience for it.” Her arousal was fading, I had to do something to fix this.
“Come with me” I said simply, leading her in front of her mirror. “Look at yourself, Jessica. Really look.” I was standing behind her, looking with her. I also stood close enough so she could feel my erection pressing into her cheeks. I kept kissing her neck and shoulder, peeling down the strap of her sleepwear. Soon her breast came into view, sagging but full. “Jessica, I find most women beautiful, each in their own way. I don’t care about your age because it just doesn’t matter to me. You have a lovely face” I softly spoke as my hand covered her bare left breast for the first time.
“You have a lovely body. I don’t expect you to look like you’re 30. If you did, it would be from so many surgeries that you’d be plastic. You’re not, though. You’re you, the real you, and you’re a beautiful lady. Now, would you please let me take you to bed and share what we both have been needing all night long?”
She turned back to me and kissed me really hard before letting it go. “I’m sorry, Paul. I shouldn’t have said that to you. You’re such a sweet man, a kind man. And now you’re going to take me to bed and you’re going to fuck me hard. That’s what I need.” I raised an eyebrow when she said ‘fuck’; it caught me by surprise. Then we both broke out in laughter, and there was no more nervousness between us.
I got out of my pants and left the blue striped boxers on. We got into bed and were kissing like long time lovers. Our lips moved all over each other’s bodies, and the moans and gasps were very real, for both of us. She was a very exciting lover. Her hands were skilled and from her kisses, I got the feeling her mouth was as well. It’s not like my generation invented oral sex.
I eased her out of the peignoir, and she was just wearing a pair of pink embroidered panties with a very sexy brief cut that fit her well, and open toe slippers. The effect was powerful, and my cock throbbed with hunger. I didn’t have to fake anything with Jessica. I rarely do with any woman, but there was something very special about her. I didn’t feel sorry for her; I felt honest to God desire.
“I bet you enjoy being tasted, Jessica” I said with a lusty smile.
“I sure as hell used to. Why? Do you want to taste me, Paul? It’s been a long time for me.” Her eyes were a little glassy and her hips were moving a little, side to side. I ran my hands all over her torso, and I could feel how aroused she was.
“I do. After I taste other things first.” I kissed her hard, our tongues darting back and forth, and our bodies moved against each other. I kissed down her throat, down to her chest, to her nipples, a little misshapen from the effects of time, but still beautiful. I licked all over her full tits, sucking and softly biting, causing Jessica to whimper as she ran her fingers through the hair on back of my head.
“My god, I’ve missed this so much” she said kind of offhandedly, like it wasn’t directed to me nor to herself. “You’re so good at this. My body is firing on all circuits.”
I didn’t respond; there was no reason to. Instead, I gradually made my way down her body, over the slight bulge of her tummy kissing all the way, until I was looking right at her bush. I took in her scent, faint but pleasant. “I hope you still like this, Jessica” I smiled. “It’s one of my favorite things to do to a woman.”
“Paul, I know I’ve gone through some changes down there over the years.” Her expression was sweet but also a little sad. “You really don’t have to do this.”
“What if I want to? I want to give you all the pleasure you deserve. You’re excited, you’re beautiful and I want do all the things you love.” I took a long slow lick along her lips, and she shuddered with a deep gasp. I kissed all around her pussy, along her inner thighs, on her mound, and I bent her legs higher so I could lick her butt cheeks as well. Every so often I went back to her pussy and caressed her lips with my tongue. All the while, Jessica made low guttural sounds and she writhed every time I touched her lower lips.
“My clitoris, Paul. Please don’t ignore it.” Her tone was getting desperate.
“I would never ignore your clit, Jessica. I’m just teasing you, working you up to it.” I rubbed her lips with my fingers as I bit softly on her thighs. Jessica whimpered, almost there. So close now.
She arched her back, really in need now, and then I went to her swollen pearl and swirled my tongue all around it. My thumbs pulled her lips apart and I hit it again, and Jessica grunted, her body went taught, and she had an orgasm, a strong one, that took her breath away for a few seconds. The fingers on her left hand pulled on her right nipple and the right hand grabbed my head, pushing my face hard on her pussy, which now was nice and wet.
While she recovered, I eased off my shorts and got a condom from my pants. “Paul, you don’t need that. I haven’t had sex in four years and there’s nothing you could pass on to me worse than what I have already. And besides, I’m sure you wouldn’t do that to me anyways.” I thought for a second and decided she was right. Besides, I knew I was ‘clean’. I got tested regularly. I put the square foil back in my pocket.
Jessica’s legs parted a little wider, inviting me to enter her, to fill her with my warmth. I got between her thighs and slowly let my cock slide in her pussy as I kissed her repeatedly, sweet little kisses until I was all the way in; then I gave her a huge lover’s kiss as her legs closed around my hips. Her moans were deep and her breaths were shallow. “Paul, so good, so good” she whimpered with her eyes, clear and blue, locked with mine.
She wasn’t all that tight; her muscles weren’t what they once were. But it was a comfortable fit, with enough pressure on the head of my cock, and she was surprisingly slippery between her natural lubrication and my saliva. I kissed her lips and her neck, then her shoulders and her breasts. Her nipples were sensitive and each time I suckled, she shifted her hips around, giving me a really great ride. Jessica was right; she WAS a great partner in bed.
I lifted on my hands and smiled tenderly. “Honey, you’re a wonderful lover. I hope you’re feeling as good as I am right now.’ Another series of kisses.
“I must…be having a better time” she gasped, almost breathless. “Please don’t stop, Paul. I’m right on the edge. So close. You can go faster. Please go faster. I can take it. Oh God!” She cried out as her climax shook her. Her fingers dug into my shoulders and she pulled me down for a great, hot kiss.
We cuddled closely, as nice as any woman I’d ever been with of any age. I can’t exactly say what it was about Jessica that I found so exciting and so fulfilling. All In can say is she was one of the best partners I ever experienced. I think it was the way we connected emotionally. There was just something so special about her, age 72 notwithstanding.
Jessica smiled warmly at me. “That was something else, Paul. I haven’t felt that in….well, a very long time. I missed it. I miss a man in my bed.” I went to her and kissed her passionately as my cock brushed against her thigh. “I love that too. The feeling of a very hard penis against any part of my body. Including my tongue.” Her smile became more playful. “Like it’s going to be now.”
“You don’t have to, Jessica. This is all about you, remember?”
“What if I want to? I always enjoyed giving head.” Again, her language was a little shocking, as if my grandmother talked like that. Thankfully, Jessica was NOT my grandmother. She was sexy and sensual, something I never associated with my grandmother. “I want you to stand up for me. I want to do this my way.”
“I’m not going to argue with you, lady” I said with a chuckle. She had me stand next to the bed and she sat on the edge. She grabbed me around the base, and I felt my cock swell in her hand, “You look very tasty, Paul. And I’m hungry.” She looked up into my eyes as she placed kisses all over the head and shaft. I sensed she wanted to be watched and watch her I did. Her lips were thin, but her tongue was very talented. I’d bet she was as good at giving head then as she was years before. Some things you just never forget.
“You’re really good at that, Honey” I said as I ran my fingers through her hair, encouraging her with the touch of my hands. She applied more pressure with her tongue as her mouth moved up and down, then she used her hand to hold my cock up towards my tummy as she licked my balls. Why this surprised me, I don’t really know. She told me she loved sex, and it really shouldn’t have been shocking that she was good at it and loved to have fun with it.
I took charge then, pushing my cock back into her mouth, moving as if I was fucking her. Not too forcefully: I didn’t know how much was too much. Her fingers were travelling all over my ass and thighs, doing her own exploration of my body. The fingers of one hand teased my balls, now wet from being licked and sucked, while the fingers of the other hand found the crack between my cheeks and moved up and down along that channel. I was doing my own moaning, all authentic, when the tip of her finger found my anus. She looked into my eyes, blowing me as well as any woman had before, when the tip pushed up past my tight ring.
It was all I could do to keep from blowing my load right then. “You can go ahead, Honey” I said with a soft grunt, and she pushed that finger all the way into my anus. My cock jumped in her mouth as my dick swelled. “Do you want me to cum now? Is that what you want, Honey? My cum in your mouth?” She responded by sucking faster and harder, rubbing her flat tongue firmly along my member. Then I pushed a little deeper and my cock started spewing thick gobs of my semen. She took some down into her throat, then she pulled my cock out and jerked me fast as the rest hit her cheeks and nose. The woman could be freaky.
When she got my all, I leaned over and kissed her lips, with a few drops of my cum right there. We swapped those drops back and forth before breaking the kiss. “You’re a very sexy man, Paul! Kind of nasty too.” She said it with a big, happy smile.
“I could say the same about you, Jessica. Dirty girl.” We chuckled together and I sat with her on the bed, holding her in my arms like her lover would. I then went and got a small towel, ran it under warm water, and I brought it to her so we could clean off her face. “You really surprised me there, Honey. Taking that facial. Not many women I work with care for that sort of thing.”
“I liked it when I was in a particularly naughty mood. Not all the time. But sometimes, when I’m in the mood…. and tonight, I don’t want to leave anything out. It very well might be my last time. The only thing that would be off the table would be anal. I doubt I’m up to that these days.”
We stretched out on the bed. “Whatever you want or not, Jessica. It’s all up to you.”
“You can keep calling me Honey. It makes me feel desired. Romantic. You’re a very skilled lover, Paul. Not that I’m surprised. I really enjoyed that. And you’re a very kind and sweet young man.” She nestled closer in my arms.
“Why are you acting like this night is over, Honey? We can go again. I would love to fuck you this time, if you want. We can be a little wild.”
“I think I would love that, just like I always did. I let it slip my mind that you’re so young. And virile.” She let her fingers tickle my lower torso and I sucked in my breath sharply. And my cock began to stir. I was definitely virile. At 28 I should be.
“Honey, I am up for you. I want you.” I kissed her tenderly and reached for her right breast, massaging it in my left hand. “I’m going to make you feel as good as you ever have felt in your life.”
We kissed, over and over. More and more passionately, moving together as if we were long term lovers. Soon I was hard again, and Jessica’s eyes went wide open from a feeling of joy. “Do you need some lubricant this time, Honey? I don’t want to hurt you.”
“No, surprisingly I don’t. Between your mouth before, your first orgasm, and how turned on I am, I feel like I’m soaked. Do you mind if I’m on top? I love being in charge, at least to start.”
I kissed her once more. “We can get into any position you like, Honey. Come ride me at your own pace.”
“Oh, I’m going to fuck you as hard as I can.” Her tone was wicked and playful as she moved on top of me, straddling my groin. I held my cock upright as she lowered her pussy down. She closed her eyes and clenched her jaw as I filled her moist pussy completely. She wasn’t all that tight, but she could shift forward and put pressure on the base of my cock. Before long she was moving as hard as she could, her hips rising and falling, her ass slapping on my thighs.
“Oh my God, Paul! You feel amazing! Grab my tits and don’t be gentle about it!” I did as she ordered, roughly massaging both her bouncing tits, using my thumbs to toy with her pulsing nipples. Jessica bit her lower lip and closed her eyes as she concentrated on the old, familiar feelings she hadn’t experienced in years. She didn’t ignore me and my needs either. As she kept moving her hips, she leaned down and licked all over my nipples, getting an occasional hair on her tongue. The woman was a very giving lover.
We went like that for a while, moving together with a good rhythm, and I could sense her getting close. Her breath was coming shorter, her moans were getting raspy. I held her by her hips and I carefully turned us over so she was on her back. My cock slipped out for a few seconds, but she grabbed me and pulled me right back inside her. She raised her right leg onto my left shoulder so I could get as deep as possible, and after a couple of minutes of sweaty, vigorous screwing, Jessica grabbed my biceps and cried out “Fuck me, I’m cumming!” I slammed into her as hard as I dared (I did worry just a little about hurting her) as she reached her peak.
“Cum for me, Honey! Cum all over my cock!” I throbbed inside her. Then she surprised me by slapping my ass a few times, hard slaps.
“Cum with me, Baby! Cum in me!” The slaps put me over the top and I lunged in deep as my cock twitched with each pulse of my orgasm, my third of the night. It was great, an intense climax with one of the best women I had ever been with. And she was 72. It goes to show, sex is primarily about attitude.
I eased myself off of her body and laid next to Jessica while she again sought the shelter of my arms, which I shared gladly. I really felt affectionate towards her. It wasn’t only because of sex; she was a great lady. “That was something else, Jessica. I bet I enjoyed that as much as you did.” I kissed her head.
“Oh, I highly doubt that. I should have done this a couple of years ago. I wasted so much time. You really made this old lady feel wonderful.”
“Hey, you are NOT an “old lady”, Honey. You’re old-er. You’re only as old as you feel, and there’s no way you’re feeling old these days. You were a great partner.”
“And you’re a very fine young-er man.” We both laughed and from there on, we just talked lightly. She let me take a shower in her very comfortable bathroom and she sat with me while I got dressed.
Before I left, I sat next to her on her bed, where she was wearing a long, silk robe. I took Jessica’s hand and said “I hope you’ll call on me again while you’re feeling able. I know, that sounds like I’m trying to solicit more business for me, but it is more than that. I enjoyed the evening. If you want, we could even go to dinner one night before coming back here. But even if you don’t, would you mind if I called you sometime just to see how you’re feeling? I like you personally. I care about how you’re doing.”
Her kind eyes were a little wet. “Paul, I wish my son, Edward, was more like you. I’m not talking about sex. I mean like a man. He’s 43 and we don’t talk at all. He doesn’t even know I’m sick. He expected his father and I to support him while living as a playboy. We stopped when he was 30. We had a bitter fight, then another when his father died. Martin wrote him out of his will, and Edward was counting on his inheritance. Now, I’m sure he’s waiting for me to die, to collect. But he’s in for a surprise. He’ll get a token amount, and the rest will go to various charities.” She cried a little, the first time she did so in my presence, and I wrapped my left arm around her. “You’re a much better man than he is.”
I didn’t know what to say. I just comforted her and let her be sad for a time. Eventually she escorted me downstairs to her door. “I’d be pleased if you called me, Paul. You have such a good heart. And I hope I’m still feeling up to another appointment in a few weeks. This has been the best day I’ve had in months. Maybe years.”
I kissed her, very tenderly. “You’re a wonderful lady, Jessica. But may I make a suggestion? Call Edward. Try to bury your pain. He’s still your son, and you should make some peace with him if you can. Don’t die with this hurt in your heart, not if you can do something about it. If he treats you poorly, well, then that’s on him. Your time is short, Honey. Just try. That’s what I think, for whatever that’s worth.”
She touched my cheek with her slender fingers. “I’ll think about it, Paul. It’s the best I can do.” We kissed and said goodbye, and I went home, feeling both good and sad for her. Jessica deserved much better than the pain she was going through in her soul.
We saw each other once more as a sexual arrangement. Afterwards, she told me she did reach out to Edward through her lawyer, but he wanted nothing to do with her. At least she tried. By the time I called her a month later, Jessica was feeling the effects of her illness. I just went to her apartment to visit and keep her company a half a dozen times; I even took her to lunch once (though she really couldn’t eat much) and each time it was obvious she was deteriorating. She appreciated my visits. It helped her take her mind off the inevitable.
Then two weeks after our last visit, I got a call from her lawyer, informing me that Jessica died two days before. I knew it was coming, but it hit me hard. I don’t know why exactly I formed such a warm connection with her. You can’t always explain why some people become friends. Jessica and I were friends, though, and I went to her funeral the next day. Her son was there, seemingly unaffected by his mothers’ death. Maybe he just came for his inheritance. But she left the bulk of her fortune to various charities, and she left Edward a token $100,000. And to me, she left $1,000,000. Her lawyer, at the probate meeting, told me she told him I was a great comfort to her in her last months. I was shocked, and honestly, I didn’t want her money, not like that. I would have greatly preferred for Jessica to be alive and well. I split that million up among the charities she favored. It was my way of honoring a wonderful woman.
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
That Sunday morning, after the first time I met Jessica, I met Kelly to rent a couple of e-bikes near Central Park on the East side, and we spent a couple of hours biking around the park at a nice, leisurely pace. We rode mostly side by side so we could talk as we rode. It was good exercise but not intensive; instead, it was relaxing and fun. When we were done, we went for breakfast and then to my apartment on West 54th Street. I bought it two years previous. Two bedrooms, two baths, living room, small dining room and a kitchen (of course). It was spacious and came with all modern appliances. Before I took this job, I never dreamed of being able to afford such a place.
Kelly and I showered together, which, as you might suspect, took a lot longer than showering individually would have taken. We had a lot of fun soaping each other up all over, every nook and cranny. She was about 7 inches shorter than I am, which gave her a good angle for giving me head, but I really had to crouch down to do the same for her. I licked her all around while my hands kept sliding all over her small tits, gliding actually thanks to the soap. Her eyes watched me, and I stuck out my tongue as far as I could so she could see me lapping at her lips and her clit. She held onto the safety bars while she ground her pussy down hard on my tongue and chin.
After she came, I stood up, kissing her very warm body along the way. “I can’t believe how much I enjoy sex with you, Paul. No one’s ever been able to do that for me before. I think I’m still shaking!”
We kissed hungrily; I didn’t cum when she sucked me and she wasn’t done yet. We still wanted to screw each other, so Kelly turned away from me, grabbed one of the bars again, and presented her cute ass to me. “You make such an inviting target, you sexy girl. I’m almost tempted to fuck your nice round ass instead.” I gave her a light spank and we both laughed.
“Maybe some other time when I’m feeling more adventurous. I’m still learning to enjoy you in my pussy. Which you need to do already!” This time she spanked herself, a little harder than I did, and I stepped closer and pressed the head of my cock to her lips before easing into her hot hole. We both made obvious sexual sounds as my cock slipped all the way inside her, and we quickly found our rhythm. Slow and easy became moderate and pleasurable became hard and exquisite. I thrust hard and reached around her hips to tease her clit, and Kelly pulled on her nipples. Her pussy was spasming all around my cock, causing me to erupt inside her, which brought her off with me. Just awesome.
After enjoying the afterglow, I helped Kelly stand up straight and she turned to me to kiss me. “You’re doing the most amazing things to me, Paul. I can’t believe what I’ve been missing all this time.” She pressed the side of her face to my chest as water kept pouring down our bodies.
I kept my arms around her, reminded of what I had been missing the last few years. “You’re doing great things to me as well. And I enjoy your company. But I think we should take the rest of this cuddle-fest to the living room, after we dry off. It’s really hot in here.” We smiled as I turned the water to a lower temperature setting, so we could cool off before we stepped out.
We took our time in the living room, looking at the Sunday paper to figure out what we wanted to do with the rest of the day (I liked getting the Sunday New York Times and going through the sections during the week). Kelly had brought a bag of clothes with her, enough so she could spend the night and go straight to work in the morning.
We figured if we hurried, we could make it to Lincoln Center to see a visiting orchestra. With a little luck catching a cab, we’d make it just in time to get there for the beginning. It turned into a nice afternoon of great music.
Afterwards, we just chose a restaurant nearby, with a good reputation for Hungarian food. Over a good dinner we talked. And we talked and talked. We stayed at the table long after we finished coffee and dessert, lost in conversation. It felt completely natural; we even ignored the waiter giving us dirty looks for keeping his table from turning over. When we finally left, I gave him an extra-large tip for the inconvenience.
We walked slowly, enjoying the warm spring evening and the sounds of Manhattan. I took her hand, and she leaned as close to me as we could get while walking. I asked her “Kelly, would you like to spend the night? I’d enjoy it if you did. We might even find something fun to do before we go to sleep.” I grinned at her, showing off my perfect teeth.
She showed me hers and said “I was hoping you’d say that. I didn’t want to go home tonight. You really do put me at ease, Paul. I had such a nice time today.”
“So did I, Baby. One of the very best days I can remember having with a woman.” We stopped and kissed right in the middle of the block, people passing us by at various speeds and from both directions. Barely anyone paid us any attention. That’s how New York is. People mostly mind their business.
Later that night, after we made love, slow and sweet, we were cuddling in bed, tired and relaxed. Her fingers were playing with my chest hair, and I was tickling her butt. Nice, soft, with a perfect shape. Every so often she giggled from my touch while I sighed from hers.
“Paul,” she said softly in the mostly dark room, “I know it’s way too soon to talk about where we’re going with this. Right now, I’m enjoying seeing you, and you’re giving me a bliss I thought I was going to have to live without. So, for right now, I’m content with this casual, comfortable thing we have. But if it continues, at some point you’re going to have to make a choice. Not now, but at some point. I’m not even asking you about my mother or to stop seeing her Fridays. It’s weird if I think about it, so I’m trying not to think about it.”
“I appreciate you not pushing me on this, Kelly, because it is too soon. This feels great, not just the physical aspects, but the way we connect. But it’s too soon to be talking about anything long term.”
“Paul, do you mind if I ask you a question?”
“I guess it depends. I don’t know if I’m ready to answer every question you might have. I don’t think we’re quite that close yet.”
“It’s up to you. If you don’t want to, I’ll understand. You said you’ve been doing this for over three years now, right?”
“Yes, a little over three.”
“Why are you still doing it? I have an idea what a man whose clientele are all women like my mom pay for your services. She gave me a rough idea. You must have money set aside unless you’re a gambler or something. Why continue? You could use that to start any sort of life you want, any sort of business. Well, almost any.”
“I’ll answer that. First, up until now, I haven’t had anyone in my life to whom I need to be accountable. So I might as well make the money while I can. I’m only 28; it’s not like I’ll be retiring. I have to do something with my life. At one time I thought it might be a psychologist, but I’m not so sure about it now. Opening a business can cost a lot of money and then you need funds to live off of while you pray your new business makes it. So a million is not all that much. I used to think I’d do it for another three or four years. Now, I’m not so sure. I’d have to be in love with someone, heading for a permanent future, to quit before that.”
“Even if I could live with you doing this while we are a couple, I’d eventually have to put my foot down about my mother. I can’t imagine she’d want to keep hiring you if she knew we were together as a couple.”
“Honey, believe me, if we get to that point, I’ll have to end it with her, at the least. I think it would be too strange for all of us.” And with that slightly unsettling thought, we turned over so I spooned Kelly and we fell into a slightly troubled sleep.
XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX
Over the next month, Kelly and I continued to spend our Sunday’s together most weeks as well as Tuesday nights when she didn’t have to work late. I started calling my parents in Brooklyn each week, trying to work towards a rapprochement. It was an iffy situation. I tried because of that talk I had with Jessica. I encouraged her to make peace with her son, after all. It would take time to see if we could fix things.
Sometimes one of our established clients, or a new one, would call Diana and request something… different. Like those couples that wanted to act out their cuckold fantasies. That, as I mentioned, was not my thing at all, though I did it. It came with the job. But sometimes the client wanted to relive a memory from their younger days or live out a fantasy they never had the opportunity to play. One of my semi-regulars, Samantha “Sam” Waterman, had such a request: she wanted a threesome with me and another woman. That was hardly a chore for me because she wanted Diana to supply the other woman, which meant a youngish call girl. Diana had a few Madame’s she knew who had their own women working for them. Their costs, and therefore their fees, were a little higher because they had to supply physical protection for their young women whether they went to a single man’s home or were hired for a party. That could be dangerous for the women.
Anyways, Diana had an arrangement with a woman named Stacey. Sometime Diana supplied a man for Stacey and sometimes Stacey supplied a woman for Diana. I’d done this a couple of times over the years and met a few nice young women. Very beautiful young women. And they were personable and intelligent, or Stacey never would have hired them. So it was hardly going to be a chore for me.
Sam Waterman requested the two of us for a Saturday night at 8, so two hours before 8 I met up with a young woman named Vanessa at Stacey’s office. We had to make sure she and I had some compatibility. We sat together in a small office with coffee, and we talked a while, getting to know each other. Vanessa was a bombshell. She was about my age, about 5’4″, Latina whose parents came from the Dominican Republic. Busty and curvy, an amazing figure with broad buttocks, and dark eyes and black wavy hair to her shoulders. Sexy and sophisticated. Vanessa wasn’t her real name, any more than Paul was mine. (Anita and Kelly knew my real name, but I’m sticking with “Paul” to make the narrative go easier). She took it because she resembled the legendary porn star from the 70s and 80s, Vanessa Del Rio. If her sexuality was even half of the original Vanessa’s, she would be a wild ride for both Sam and me.
I gave some information about Sam to Vanessa, so she knew what to expect. Sam was in her mid-40s, a tall, slender blond with zero fat. Long, lean legs, nice B cup breasts, and she moved like a dancer. A real trophy wife whose husband was out of town on business half the time. She only called for an appointment when her husband was away, so discretion was vital. I saw her once or twice a month. The contrast between the two women was pronounced. I wouldn’t be surprised if Sam asked for someone like Vanessa specifically.
We took a town car over to Sam’s townhouse and talked quietly on the ride over, going through the range of possibilities, depending on what Sam requested of us. We both had few limitations, but you never knew what a client might want. We were both dressed like young, well-to-do professionals on a night on the town. For me that meant expensive grey slacks and a Navy sports jacket, no tie, and Vanessa wore this form-hugging multi-colored flowing dress that went midway down her thighs. She was wearing 4 inch heels and patterned black hosiery, all very expensive. And her makeup was not subtle, a little heavy, like she was going out to be seen.
Sam met us at the door; there were no servants working whenever I came over. She kissed both Vanessa and me on our cheeks and guided us into her plush living room. She was also dressed as if ready for a night out clubbing. A dark blue silk blouse unbuttoned to the beginning of her tummy, no bra (she didn’t need one), and a tight red skirt that just hugged her slender ass, and red hosiery. And black pumps, three inches, that made her almost as tall as me.
We sat with drinks and got to know each other all around. Sam clearly liked what she saw in Vanessa, and they had an immediate connection. We chatted amiably for about an hour, making sure everyone was comfortable with each other. Then it was time to get to business.
I opened things up. “Sam, Vanessa knows that you and I have a fairly longstanding acquaintance. I met Vanessa a few hours ago, and we’re also in sync with each other. So why don’t you tell us what you’re interested in tonight? Tell us how we can make this a special evening.” Vanessa leaned forward, as curious as I was.
Sam took another sip of her vodka and said “I’ve actually got two fantasies I want to live out. Well, one will be only halfway.” Another sip: she was clearly nervous, though she shouldn’t have been. We were there to please. “I’ve wanted to have a threesome for a long time. I have some attraction towards women, but I don’t think I’d want a one-on-one encounter. I want to be with a man at the same time and I trust Paul completely. At the same time, ever since I saw my first dirty movie back in college, I get hot at the thought of being in one. I know we’re not actually going to do that. There will be no filming of this. I wouldn’t actually do it, and I wouldn’t expect anyone to do it either. I just want to do this as if we’re in a very dirty movie, dirty talk, different positions. And some very hot screwing. Are you both into this?” She asked nervously, biting her lip. It was a very sexy look.
I let Vanessa answer first. “Speaking for myself, I’ve had a number of female lovers as well as threesomes, not to mention a few orgies. And those were in my private life.” She was smiling warmly, friendly with a measure of danger. “And men often ask me to play the role of a porn actress.” Vanessa turned to me, not at all worried that I might not be on board.
“Hey, this is all fine with me. I’ve been asked to do all manner of kinky things over the years. It’s good for me, Sam. I think we’re going to give you a great time, and I think Vanessa and I are going to have some fun as well.”
As Sam put our empty glasses on her bar cart, she said “I expect so. At first, I want you two to start things off while I watch you. Then I’ll join in. I also like to watch.” She blushed, but she had nothing to feel embarrassed about. Sex workers are the least judgmental when it comes to other people’s personal fetishes. Vanessa and I had heard much worse in the past. She then asked us about certain sex acts and whether they made us feel odd, but we were just fine. Sam smiled broadly; she knew she was going to have a great time with us.
We took our signal from Sam, and we all stepped into the small elevator that couldn’t have held another person. We rode up to the fourth floor, which was where 2 bedrooms were, including the master bedroom. A big king-sized four poster bed took the center of the room. Same took off her skirt only, so we could see her in a red lace garter belt with matching almost micro-panties. She sat in an overstuffed chair and made herself very comfortable, ready to watch the opening act of the show. It was time for Vanessa and I to get things going.
We spoke quietly for two minutes, deciding how we wanted to start things. Sam left it up to us to roleplay it any way we wanted. She’d be following along, and she let us know she had no hangups when it came to whatever we wanted to do. After a quick back-and-forth, we decided a good way to make the sex hot and dirty with the nasty language Sam craved was to act out a hate fuck. I’d done it a few times, but Vanessa said a lot of her clients requested it, so she was well skilled with that scenario.
“You little bitch!” I said with a growl in my throat. “You think you can cheat on me with one of your fucking girlfriends? You’d cut my balls off if I slept with another woman!”
“If you had any balls at all, I wouldn’t have to get my kicks with another person! Sam screws me better than you ever have, and she doesn’t even need a dick to do it! You worthless….” OK, you get the idea. We were playing out a couple dealing with her infidelity with another woman.
“You think I can’t fuck you right? We’ll see about that!” I aggressively (but carefully) threw Vanessa on the big bed and climbed on top, straddling her body while we were still clothed. “If it’s dick you want, I’ll give you all you can handle!” I grabbed her around her throat with one hand (not hard enough to leave any marks, simulated) and while she ‘struggled’, I undid my belt and pants with my free hand and I whipped out my cock through the fly on my red silk boxers.
“Fuck you, you bastard!” Vanessa had a look of defiance as she pretended to fight me off, but when I pushed my cock to her lips, she didn’t resist all that much, accepting me into her mouth.
“No, FUCK YOU, you bitch!” I started fucking her face, fast and a little rough, and we were making very wet sounds as she sucked me with great talent. I looked briefly over at Sam and saw she was enjoying the show so far. She hiked up her skirt, showing off her stocking tops attached to a matching red garter belt. Her panties, also red, were pulled aside and I could see her fingers floating over her distended lips and her fingernail teasing her clit. She was having a good time, but she didn’t want to cum, not yet.
I kept fucking Vanessa’s face as I leaned backwards and put my hand up her black skirt, which I pulled up so Sam could see. Vanessa had thigh highs on and she moved her legs around while I rubbed her pussy over her silk panties. She groaned loud so Sam could hear. I took out my cock and slapped her cheeks with my turgid, sloppy member. “You’re such a dirty man, you bastard” she groaned, but her lust was obvious. Hell, she was even wet; I could feel it through her silk. Then, before I put my cock back in her mouth, she said as softly as she could “Rip off my blouse. Don’t worry, I have a change of clothes in my bag. Just do it, she’ll love it!”
I didn’t hesitate; I just grabbed her blouse by the buttons and pulled hard, sending buttons flying all over the place, and Vanessa’s big, beautiful brown tits were barely contained in a black lace bra. From where Sam sat, we heard her cry out as she stuffed two fingers into her dripping snatch, fingering herself furiously.
“You can make me suck your dick, you prick, but I doubt you can fuck me proper!” my playmate spat at me. “Do it, you worm! Do it!”
“You wanna get fucked, you whore? I’ll give you the fuck of your life!” I got off her and turned her over, not gently at all. I pulled her up to her hands and knees, still in her skirt, her torn blouse, and what I found were crotchless panties, and I shed my clothes as fast as I could.
“Come on already! Do it, show me you can fuck me, you asshole!” She sounded hot as a volcano, but I didn’t know how much of that was real and how much was for Sam, who had ditched her own blouse and was rubbing her own small tits hard while her fingers stayed buried in her cunt. Her body was writhing in the chair and I suspected she’d be joining us soon.
Vanessa took her tits out from the cups of her bra and pulled hard on her long nipples as I got behind her and took her pussy with one smooth stroke until my groin was on her brown, round ass. She clawed at the sheets, gritting her teeth. “Fuck me, motherfucker….harder, do it harder!”
“Yes, fuck her, fuck that slut hard!” Sam moaned, almost like she didn’t expect to be heard. She was leaking copious amounts of lubrication, more than I ever experienced with her before. Then she got up from the chair and bent in front of Vanessa, kissing her like long time lovers while I fucked her hard and rough. “Spank her, you bastard. Slap her ass red!” Sam grabbed the back of my hair and then kissed me just as hard, just as I brought my hand down on Vanessa’s ass, making her yelp. “Harder!” Sam demanded, and I looked at Vanessa first to make sure she was up to a harder spanking. She nodded her head, and I smacked her ass hard enough to sound like a thunderclap. She grunted briefly, until Sam reached down and pushed her pussy into Vanessa’s face, ‘forcing’ the younger Hispanic woman to eat her blond cunt.
Sam was almost immediately thrusting her hips back and forth and Vanessa, a true champ, was eating her vigorously as I kept fucking her from behind and spanking her until her ass was pink.
Sam pulled away, on the verge of an explosive climax, and laid down on the bed on her right side, spreading her legs wide. “Eat me! Both of you! Eat my ass and cunt! Fuck, I need it so bad!” I pulled out of Vanessa’s sloppy pussy and we both made our way to Sam. I went for her pussy while Vanessa dug into the crack of her ass. We were eating her aggressively, as if we were all starring in a dirty movie, while Sam shook all over, going through a series of orgasms, spewing a long stream of foul words as our tongues kept up the attack. We switched back and forth, we kissed as we licked her, and finally Sam screamed as an explosive climax overtook her.
Vanessa and I slowly eased off, until Sam just kind of collapsed. We kissed her all over her body, keeping her fire stoked. I knew from my own experience with her that Sam could take it. She could keep going all night long, even after I was done for the night.
“You two are awesome!” Sam complimented us. “I wouldn’t believe you’ve never been together before. And you’re so fucking hot!” She exclaimed as she kissed Vanessa warmly.
“Thank you, Sam. You’re pretty awesome yourself” Vanessa said, returning the compliment.
“What about me?” I asked, pretending my feeling were hurt. I grinned as I said it.
“You, Paul, I already knew to be a very hot and sexy man. We do have a history.” She moved to me and shared her lips with me, kind of sweet and fun, but she was definitely still hot. Good thing, because my dick was still hard like petrified wood. And looking at Vanessa, I could tell she was pretty hot as well. I had no idea if she usually got aroused when she was working, but she had been all through the earlier part of the evening, and she didn’t cum before.
Sam’s tongue was in my mouth, and I pulled Vanessa into that kiss, so the three of us were locking lips and swirling tongues. Sam took Vanessa’s bra off, which had to feel better for her. Then both women’s skirts were gone, and I found my face in between Sam’s thighs, licking hungrily all over her inner thighs and her pussy, which was freely flowing, as she went down eagerly on Vanessa, who was blowing me in our little triangle. Then Sam moved away so she could share my cock like you often see in a movie.
The two women were having a great time licking my cock all over, and of course, I was having an even better time. Sucking on the head, licking up and down the shaft, sucking my balls…. they were doing every nasty thing to me they could think of, including rimming my ass. As turned on as I was, I was struggling to keep from cumming. Whether I came then or later was up to Sam, who was kissing Vanessa while my cock was between their lips.
As if she could read my mind, she said to Vanessa “Do you want to share his cum with me? I know we can get him hard again. He gets so nice and hard so quickly.” Talking about me like I was in another room.
“Yeah, let’s get him off. Then you can fuck him when he gets hard again. Stand up, Paul. We want your cum on our faces.” Sam nodded enthusiastically, so I stood up with my cock sticking out straight, except for the slight curve of my shaft.
“Do you want me to jerk off on your faces? Or would you like the pleasure?” I asked with intense lust. My hand was sliding up and down the length, waiting for their answer. I had to go easy; I was very close.
“Let us do it, you sexy man!” Sam decided, and both women grabbed my cock and jerked me fast. “Cum on us, Paul. Shoot that hot cum all over us!”
“Do it, do it, cum for us now!” Vanessa chimed in, tickling my balls, and in a few seconds my ass clenched tight as a hot spray of semen covered both their faces as they started kissing and sharing before I was even finished. I grunted as the chords on my neck were tight and they milked me dry. For a little while at least. Sam was right. I would recover quickly with a little help from my playmates.
First, though, I had to sit on the bed, and both women attacked me, kissing wildly, getting my own cum on my face before we all started sharing it back and forth. I’d had a few threesomes before, mostly in my job, twice in college, but this was by far the hottest one I’d been in to that point.
Then we rested a bit, laughing, sticky, having a very good time. It could be a hell of a way to make a living, something many guys would have envied. And a hell of a living it was.
Sam excused herself, first to use her bathroom, which she offered us when she was finished, and then she went to get us all cold bottles of water. That left Vanessa and me alone for a few minutes. I offered to go with Sam, but she told me to stay. “Rest, Paul. I need you to get recharged. I still haven’t been fucked yet.” She went with a chuckle.
When we were alone, Vanessa said “This is the best threesome I’ve ever done professionally. She’s a wild one, isn’t she?”
“Oh yeah. Sam always is a great partner. I wouldn’t be surprised if she wants us both from time to time in the future. Her money is hers; she’s an heiress, so she doesn’t rely on her husband’s money. And she’s just a really sweet person as well. She’s never been rude to me in any way. It’s actually something I rarely have to deal with when working with women.”
“I wish I could say the same. So many of the men, after they get what they wanted, treat me like some sort of tramp. It’s hard not to take it personally sometimes. They can be such assholes. This is so much better. Just one thing, Paul. I haven’t cum yet. You’d better make sure you take care of that!” She giggled and I joined her as Sam came back in the room with three bottles of ice-cold water.
It wasn’t long before I was hard again, thanks to a little more cock sucking from Vanessa while I watched Sam bury her face between her thighs, digging in on her bronze bare pussy like she was starved for it. It was Sam’s first time with a woman, and she took to it like a true natural. Watching her was a great help for my erection.
Soon I was fucking Sam from behind while she kept lapping away at Vanessa’s now steamy pussy. Both women were close, and Vanessa got there first. She grabbed the back of Sam’s head and thrust her hips roughly in her face as her legs flailed in orgasm. Then she turned around so her face was right under where my dick thrust over and over into Sam’s snatch. She licked both of us, from my balls to Sam’s clit while Sam rubbed Vanessa’s lips and clit. We were all too deep in lusty feelings to speak, and then we all came within a few minutes of each other, with me filling the condom with another thick load that just left me wasted. We fell into a heaping mass of tangled limbs, all of us sweaty and gasping for breath.
After some light chat, Sam welcomed us to join her in her oversized shower and the three of us cleaned up with no funny business (well, a little bit of pinch and tickle; it was fun), and then Vanessa and I dressed. After thanking us for a great time and letting us know she’d be calling for us both again, Sam said goodnight to us at about 1 AM. I asked Vanessa where she lived to see if we could split a taxi.
“I know I should be exhausted and ready to collapse in bed, but I could really go for a drink, Paul. Would you like to join me?” She was flirting with me, giving me looks with those big brown eyes of hers.
“I wouldn’t mind a drink or two. There are some bars over on 2nd Avenue.” I took her arm and we walked less than a block to 2nd and went into a bar that was still very busy (it was Saturday night) with some music blaring in the back. We sat near the front where it was quieter and ordered drinks from the waitress.
“That was actually fun tonight, Paul. I almost never get excited with my clients. It’s not what I’m there for.”
“It’s different for me” I replied. “I can’t fake it. I have to get off; it’s expected of me. And it means I can’t book more than two clients at most on a given day. Even that can get challenging by the end of the day.”
“Poor you” she said with a light laugh. “Making thousands of dollars AND getting off! You have a lot of men’s dream job!”
“Funny, I was just thinking that a little earlier tonight. But there’s a lot of work to this as well. I’m sure you also have to be something of a psychologist with your clients.”
“Like you wouldn’t believe. Well, maybe YOU would.
We talked and ordered another drink, along with a couple of appetizers. I found I really liked Vanessa as a friend. We had a lot in common besides our work. We came from middle class homes that were not exactly happy. We both studied psychology in college, me at Columbia and her at NYU. She also enjoyed cultural outings like I did. And she loved to go out dancing, something I hadn’t done in years. There was a lot to be attracted to in Vanessa. Of course, there also was a woman named Kelly out there….
About 2:30, the day was catching up to us. Vanessa lived downtown in the East 30s while I lived in the other direction, in the West 50s. After I paid the check, we went out to flag down a cab. I figured it would be hard enough to get one and besides, I thought at that hour I should escort her home before having the driver take me to my place.
We rode in mostly comfortable silence, holding hands and smiling. If we hadn’t had such a wild evening, I’m sure she would have invited me in to spend the night. But we were all sexed out, and besides, the next day was Sunday and I had plans with Kelly.
When we got to Vanessa’s building, I asked the driver to wait with the meter running while I escorted her into the vestibule. We were a little unsure as to what to say at that point. There was a certain sexual tension between us, even after the events of the evening. “Vanessa, forgetting why we met today, I had a good time with you when we were alone, talking. Under other circumstances I would love to see you in our private lives. But I’m kind of seeing someone on my days off. It’s new, and there’s no commitment or exclusivity, but I like her, she knows what I do, and I don’t think I have the time to see someone else right now.”
She smiled shyly, and she looked a little disappointed. “That’s too bad, Paul. I like you as well and I had a good time with you. It would be nice to have someone in my private life as well. It’s been quite a while for me. Our jobs don’t exactly work well for personal relationships. Let me give you my number. Maybe we can at least be friends. I would like to have a man I can talk to when the job gets to me, or just to talk with. And perhaps your relationship with that woman won’t work out. I usually have off Tuesdays, Wednesdays and Thursdays. Though I’m not working tomorrow. I don’t have any appointments and I don’t think I have it in me after this evening.”
We laughed lightly, and we were clearly attracted to each other. But one woman was already enough of a complication. Two would be unmanageable. “I would like for us to be friends at least, Vanessa.” We exchanged numbers in our phones, and after we kissed cheeks goodnight, I went back to my cab and had him take me home.
I got out of my clothes and wearily brushed and flossed before falling into bed. And honestly, my thoughts were more of Vanessa than they were of Kelly, whom I was set to meet at 1, without set plans for the day. A normal guy with a normal lifestyle could have seen both of them. There was no commitment with Kelly. I liked her, a lot. But I couldn’t commit to her even if I wanted to unless I left my job, and I wasn’t sure if I even wanted to do that. With Vanessa, I probably wouldn’t have to. Vanessa. I was thinking about her, and I knew her all of nine hours.
Note: You can change font size, font face, and turn on dark mode by clicking the “A” icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here