I'm Just a Gigolo Ch. 03

In this chapter, Daniel has sex with his first real job, Andrea. He also helps train Cynthia some more so she gets better at licking pussy. Daniel also recruits another female for Elite, for women only. This chapter contains regular intercourse, oral sex, lesbian sex, and group sex. This work is copyrighted, and not to be altered, duplicated, copied or published anywhere, including alternative media, without the written consent of the author. © Copyright 2025.

I'm Just a Gigolo, Ch 3

Andrea, My First Paying Job

On my walk to Andrea's place, I stopped for some flowers for her from a street vendor. Some daisies as opposed to roses, as I certainly didn't expect this would be a romantic relationship. I arrived five minutes before my appointment. I rang the doorbell and the door was opened by a butler or valet wearing the house livery. There was a maid setting up a silver service in the room the butler led me to, a type of sitting room. There were a half dozen powdery cookies laid out on a plate next to the silver tray. The butler asked if he could take my flowers, but I wanted Andrea to get them from me, so I declined.

"Coffee or tea, sir?"

"Coffee, cream, no sugar."

"Yes, sir." She poured me my coffee and she poured out a hot tea with some lemon for who I assumed would be Andrea. I took a seat and sipped my coffee while I waited. I made a mental note that Andrea liked hot tea with lemon. The maid left.

Andrea arrived about five minutes after seven, so ten minutes after I'd arrived. She swept into the room wearing a lovely dress which accentuated her cleavage. As Julie had warned, she was a little overweight, perhaps twenty to thirty pounds by my estimation. I stood up as she entered the room. She stopped on seeing me, and gave me the once over, smiling at what she saw.

"Daniel Bancroft, I presume," she said.

"Yes, Ma'am."

She handed me her hand saying, "Andrea Gormley."

Instead of shaking her hand, I bowed over it, kissing her knuckles. "Your servant, Andrea."

I reached down to the table and grabbed my small bouquet of daisies, handing them to her. "For you. May I say that your gown is almost as lovely as you are."

Andrea smiled again, accepting them. "Somebody raised you right."

"My parents."

She rang a bell and the maid returned. "Please put these in water and put them beside my bed."

"Yes, ma'am."

As soon as the maid was gone again, Andrea asked, "What did Julie tell you about our date tonight?"

"Only that it was a play, not which one."

"Have you seen Wicked?"

"Only the movie. I can't afford Broadway plays. I was disappointed they broke it into two parts."

"We'll remedy that tonight. Why don't you have a seat and tell me a little about yourself."

I spent around fifteen minutes telling her a little about myself, where I was born, where I was going to college and my degree program, my high school sports efforts and the like. The butler came in and informed us that her car was ready. I helped drape a stole over her shoulders and we went to the limo idling on the street, the driver holding the door. I helped her into the car and slid in beside her. I held her hand on the drive, gently rubbing the back of it with my thumb. Andrea took advantage of our closeness to put her hand on my cock, giving it a little squeeze before releasing it, checking me out.

"Mmm, nice," she said.

The driver dropped us off at the theater and Andrea handed the usher our tickets and he led us to our seats, good ones about a third of the way back from the orchestra pit, the middle section, on the aisle. I let her in and sat on the aisle. We had a chance to chat a bit more before the orchestra started warming up. I continued holding her hand during the first act, slowly and softly rubbing it. At the intermission, we got up and I used the restroom before rejoining my date and buying us a glass of champagne.

She'd apparently run into a couple that she knew. When I joined her they both gave me the once over, the woman developing a slight sneer as she figured out my age.

"My, my, Andrea, aren't you robbing the cradle," she said.

"Your friends?" I asked.

"Lincoln and Nancy Hawkins, meet Dan Bancroft."

I took Andrea's hand, kissing her knuckles again. "You need a better class of friend," I said.

"What?" Nancy said. Of course she'd be the most offended, the offensive one.

"Just because Ms. Gormley is no longer married, do you expect her to stay at home waiting to meet the next Mr. Right? She's still a vibrant, beautiful woman, who should be seen out in public, not withering away at home. I, for one, think she's very brave for choosing to find someone who can escort her to events like these, instead of staying cooped up. I hope I can have courage like hers when I get older. I admire her." I brushed her cheek with my lips. "Why don't we find our seats, I don't see any reason to spend more time here where you or I can be insulted."

Andrea's smile lit up the room. "I think we shall."

I took her arm and we went back to our seats, where she gave me a kiss on the lips.

"Thank you for that. Nancy's a harridan."

"Don't be afraid to stand up for yourself," I said. "You deserve to be treated like a lady."

I put my arm around her for all of the second act, and during the third, rested my hand on her leg, very close to her pussy, lightly rubbing her thigh. I could tell she was building some sexual heat. While her dress was too long to go under without being obvious to everyone, she spread her legs enough that my hand could drift closer to her holy of holies. At the conclusion of the play, I helped her up and led her out of the theater, her hand on my arm, with me patting that hand the entire way,

As soon as we were in her limo, which was waiting outside, she was wrapped in my arms kissing me. There wasn't enough time or distance to engage in major hanky-panky, but I could slide the strap off her shoulder and pull down the dress enough to reveal a half shelf corset, with her bare nipples pointing out like bullets. I gently tongued and sucked each one before pulling the top of her dress back up. She was practically humming with sexual tension. I checked my watch. It was midnight, the witching hour.

"Our date is over," I said.

"You aren't going to leave me like this are you?" Andrea asked.

"Of course not. It only means we can get to the good stuff."

She smiled again. She really had a good smile. I kissed her some more, doing a little tongue tango. All too soon, we reached her house and we straightened up before getting out of the limo.

Andrea led me straight to her bedroom, which had a huge bed, larger than any king size I'd ever slept in. I helped her with the zipper, and the dress dropped to the floor. I picked it up and laid it over a chair near the bed. Her nipples were still puckered and she had a wet spot on her tap pants.

"I'm sure I'm a little bigger than you're used to," Andrea said. "I hope you're not disappointed."

"Not at all. You have what would be called a Rubenesque figure. A hundred-fifty years ago, it would have been considered the female ideal, a lush, full bodied woman with a little padding. I suppose tastes have altered over time, but you still have curves in all the right places."

"Oh, God, you're good. Take off your clothes." She sat down on her bed.

"Do you want a show, or speed."

"A show."

I started humming the music 'You Can Leave Your Hat On' by Joe Cocker as I slowly teased my clothes off for her. When I finally pulled my underwear off showing her the goods, Andrea gasped.

"I knew you'd be good from my quick feel in the theater, but you've even better than I expected."

"I'm glad you like it," I said.

"Like it? I love it. Come closer so I can touch you."

I approached the bed and her hand encircled my cock.

"I can't even reach all the way around it with my hand."

"You're still overdressed," I said.

"I'd like to leave my corset on. Otherwise, I look a little too lush."

"Nonsense," I said. "I want to see you in all of your naked glory." She looked doubtful. "Are you afraid I'll lose my erection if I see you naked?" I asked.

"Maybe."

"I can promise you it's not going anywhere, but inside of you."

Andrea nodded and I stripped her bare. Like I thought, maybe twety-five pounds overweight. She still had curves, despite the loss of her corset, her breasts big and unfettered. I gently pushed her back to the bed, then spread her legs as I got between them. She had a neatly trimmed bush. I licked and fingered her to three good orgasms before I got up as she moaned and shivered through my attentions to her pussy.

"Where are you going?" Andrea asked, raising her head.

"To get my condoms from my pants pocket. You do want to fuck, don't you?"

"Do I ever!" Laughing

As I got them, I asked. "Has anyone ever told you how good you taste?"

"Never."

"They should have. You taste delicious." I turned to face her so she could see I was still erect and ready. "Do you want to do the honors or should I?"

"I'll do it."

I knelt over her waist and opened the packet, handing her the condom. Before she rolled it over me, she licked a drop of precum off the tip.

"I love your cock. I bet it's going to fill me so good."

"You're about to find out," I said.

I got between her legs and rubbed the tip over her dripping pussy a few times to soak it in her juices before I placed it for penetration.

"Are you ready?" I asked.

"So ready."

I started to push inside, going slowly in case she couldn't handle the girth. Apparently, I'd done my job. It was one long, slow push to enter balls deep. I then commenced making love to her. As I kissed her, I slowly pumped in and out, frequently squeezing or mauling one of her big breasts as I did so. Despite my sex earlier in the day and the rubber, I only managed to fuck her fifteen minutes and her to two orgasms, before I gasped and filled my condom. I got up and threw the condom away, then joined her in bed once more.

"That was heavenly," she said. "Thank you."

"We're not done yet."

"Aren't we?"

"Not if I can spend the night. I brought six condoms. I'll be very disappointed if I don't use three of them before I leave."

"Oh, God, please tell me you're not joking."

I laughed. "Not joking. One of the benefits of robbing the cradle." I placed her hand on my cock, already beginning to swell again.

"Lord love a duck."

I laughed again. "Would you like to help me along?"

"Please, yes."

I fed her my cock, and she sucked on it, cleaning off most of my cum as I grew in her mouth. The harder I got, the less she could fit inside. When I was hard again, I handed her another condom and she rolled it down my shaft.

"What do you say we start with doggy this time?" I asked.

She got on her hands and knees, presenting me with her broad backside. I had an even easier time entering her the second time, and I lasted longer.

While I fucked her, I gave her tiny swats to her ass, love taps really. She seemed to enjoy that. She also seemed to enjoy me rubbing my thumb over her pucker, but she didn't invite me in, so that's all I did with it, letting her set the limits to our sex. I got four more orgasms out of her before I filled the condom with my seed. We were both pretty exhausted by the time I finished, around quarter to two, so after I climbed back into bed, I cuddled her and we went to sleep.

Andrea was still sleeping when I woke up at nine. I slipped out of bed and relieved myself, then came back. The sheet was down to her waist, so I got back into the bed and started kissing, sucking and fondling her breasts until she woke up with a lazy grin.

"I'll give you an hour to stop that."

"Sorry, but I've got other things to do."

"You're leaving?"

"No, moving on to your pussy," I said, flinging the sheet off of her.

"By all means, move along."

I made myself comfortable between her thighs, and licked her to three more orgasms before handing her a condom and kneeling over her waist again so she could roll my condom on. I made love to her once more, though hooking her legs over my elbows so I could long stroke as we fucked. I managed to hold off for about twenty minutes and as I climaxed, so did Andrea for the fourth time. We both moaned long and loud as we orgasmed.

"Tell me about your divorce," I said as we pulled apart, panting.

"My husband cheated on me. That's when I put on most of my extra pounds, around twenty of them, eating my way through my sorrow. The more I gained, the less sex we had, until I finally divorced him. Tell me the truth. I'm not really that attractive anymore, am I?"

"You're still attractive. You could stand to lose a few pounds, but it should be mostly for your health, not because you're not beautiful. I think that a lot of beauty comes from inside, a confidence that no matter what you weigh, you're beautiful and have something to offer, but lose weight for yourself and your own confidence, not because of what anyone says to you. You have the money to afford a personal trainer. So hire one if you want, and follow his or her instructions until you feel good about yourself again, no matter how much you weigh. Personally, I think you're gorgeous just the way you are, but if it will make you feel better about yourself, do something about it."

She kissed me, a long, slow, heated kiss, then she got up and got her phone out of her purse.

Andrea called someone, and when they answered, she said, "Julie, you're not charging enough. Up your price twenty-five percent. You'll still have trouble scheduling him. Best I ever had. Uh-huh, three times, and it was magic. Don't undervalue this stud." She hung up. "I'll feed you breakfast and have my driver take you back to school. I want to thank you for a fantastic time."

"Shower first? We can still have a little play time."

She smiled and we took a sudsy shower. I managed to give her one more orgasm there before we finished. I dressed again and she slipped on some casual sweats. We had a nice brunch and then her driver arrived to take me home. Before I left, she gave me an envelope with a thick stack of cash.

"Worth every penny," Andrea said, kissing me again.

When I got back to school, I checked the envelope and found another thousand dollars in it. Wow.

I would see Andrea a few times a year for the next five years. She took my advice and got a personal trainer. Over the next six months, she lost twenty pounds and toned up a lot. She decided that was a good weight for her, so stopped there. I agreed that what she still had looked good on her. She stopped seeing me when she remarried. I attended her wedding, as just a friend. I don't know if her husband knew that I'd helped keep her from being too lonely between her two marriages.

As a side note, Nancy Hawkins hired me for a date about a year later, while she was married to Lincoln. I didn't have sex with her, much to her disappointment, because she grabbed my cock a lot during the date. I had never forgiven her for the snotty way she'd treated Andrea, and the lack of sex afterwards was a reflection of that. I told her why when I left. I doubt if it changed her personality at all, but baby steps.

*****

A friend at school was a lesbian. Her name was Rafaela and I told her that I wanted her to come to my place on Thursday afternoon at two for some free sex.

"I don't do guys," she said.

"I know you don't. I'm going to be showing another young woman named Cynthia how to better please a woman, and then she needs to practice on someone, and she can't practice on me, so I thought you might want the job."

"Why is she coming to you for instruction?"

"Her boss suggested it."

"Her boss?"

"She's working as an escort, and even though she's never had sex with a woman before last Saturday, she has agreed to learn how so she can date both men and women. It could mean more business for her."

"Still doesn't explain why you were chosen as an instructor."

"I'm pretty good. Her boss had experienced me and thought I'd do a good job."

"Why had her boss experienced you?"

"I'm working for her too."

"You're an escort?"

"As of last Saturday."

"You're getting paid for sex?"

"Not sex, companionship. It's just a date, but sex could occur, but I'm not charging for sex. That would be illegal."

"And you say she's cute?"

"Very."

"Okay. I'll show up. I don't know if I'll have sex with her, but I'd come just for the heck of it, to see what you're up to."

"Great. I'll feed you afterwards. Come a few minutes early, in case she shows up before two."

"You got it."

******

Cynthia did arrive a few minutes early, at the same time as Rafaela, so they entered my room together. I introduced them.

"Rafaela, Cynthia. Cynthia, Rafaela. I invited Rafaela because even though I can demonstrate on you what you need to do, you should practice on someone. Rafaela wasn't sure if she wanted to be your practice dummy, but she was curious about what we're doing, and we'll see how it goes. You might practice on her, you might not. If you do, she's a lesbian, and she might be able to add to your knowledge of pussy licking."

"Great," Cynthia said, "should I get undressed?"

"Not yet. Let's chat a bit, get to know each other a little more. I think you can jump into some things too soon, and it's important to know a little bit about someone. Why don't you tell Rafaela why you decided to become an escort?"

Cynthia shared the details about her husband, his accident, and why she chose to be an escort."

"Have you had any jobs since last Saturday?" I asked.

"One Sunday night, and one last night."

"Any sex?" Rafaela asked.

"The one on Sunday wanted a blow job," Rafaela replied. "The one last night was a dinner date, business meeting. I was like eye candy, but no sex."

"How much are you getting paid as an escort?" Rafaela asked.

"One hundred an hour, of which 25% goes to the company."

"So how much were you paid for the two dates?"

"The one on Sunday was four hours, a dinner and a movie. I got three hundred for the date, and tipped a hundred for the blow job afterwards. The business dinner was also four hours long. I got three hundred and tipped twenty-five."

"Have you been on a date?" Rafaela asked me.

"Saturday night."

"How much did you get?"

"Five hours at two hundred an hour, of which I got paid $750, and tipped a thousand when I left. I spent the night though, and had sex three times."

"Was she stunning, beautiful? Why did you spend the night with her?"

"Because she needed someone to pay attention to her. She was fairly ordinary, a little plump, but a nice lady."

"$1750 dollars for one night? Why do you get paid so much more than Cynthia."

"Dan fucked me last Saturday," Cynthia said. "I've got to admit that he deserves more than I do. It was the best fucking I ever had. I didn't know you got twice as much as I did, though."

"It's more now. My date called Julie and told her to up what she was charging for me, and Julie told me on Monday they're going to start charging $250 an hour for me. Julie is hoping I can get Cynthia on a higher level. The more she can charge for Cynthia, the more they get."

"What makes you so fucking special?" Rafaela asked.

"Expertise."

"Fucking expertise?" Rafaela asked.

"Not just fucking, but making a person feel good about themselves. If you're going to go somewhere with someone, it helps them to feel like they're on a real date, and not that your services were bought and paid for. I made her feel like she was on a real date, except I was just a little more than half her age. A woman she knew even made fun of her, accusing her of robbing the cradle. I wanted her to believe she was better than that. Her vibrator might have given her as much pleasure as I did, but it was the extras that counted."

"What did you do?" Cynthia asked.

"I brought her flowers, kissed her hand when we met and throughout the night, propped up her ego when her acquaintance criticized her, made love to her, not just fucked her. I treated her like a romantic date."

"What's your secret then?" Cynthia asked.

"My parents taught me to be unfailingly polite to everyone, hold their chair at dinner, open doors, treat every woman like a lady, even my little sisters, and that was damn tough, let me tell you. Next, I figure this is a service profession. Anyone can be present, put you on their arm, but you need to be more than just there. You have to feed into their needs and fantasies.

"I made it a point to ask my date a lot of questions, get to know her a little. I found out that Andrea had a rough divorce. Her husband cheated on her, and in her sorrow, she ate more and gained more weight. He ignored her even more, and quit having sex with her until she finally divorced him. I wanted her to know that I still found her beautiful even if she carried a few more pounds than she needed. I made sure that every time I had sex, I found her sexy and that she aroused me. I've even started making notes about the things she liked and didn't like on our date. If I ever go out with Andrea again, I'll review my notes, and I won't have to ask her the same questions all over again. I'll know what she enjoyed about the sex and what she didn't like. I can ask her new questions about her life or updates on what we talked about before. While I encouraged her to get a personal trainer and lose a little weight and tone up for her own health, I found her sexy regardless, and to do it only if she wanted to, not because anyone else told her to. I made her feel better about herself, not just gave her good sex."

"As a woman, I can't really go around holding doors or chairs for my dates," Cynthia said.

"True, but you can express appreciation for when it's done for you. A glance with a smile, a word of appreciation, a touch on the arm or shoulder, letting them know you noticed their courtesy, and that you enjoyed it and would encourage them to keep doing the same thing, and reward them for it later."

"Okay. I can see that."

"Let's talk about the sex a little bit. When I went out on romantic dates with girls, I tried to pay attention to the things they liked and didn't like, not just the general things we just talked about, but the gestures, the touches they liked. What they said, or even what they didn't say, that told me something was turning them on."

"Like what?" Rafaela asked.

"Let's say I'm helping a girl take off her coat. In taking it off, I might notice a noise or a flinch she makes if I touch her neck in the process. Was it an indication she liked me to touch her neck or that it bothered her?"

"Fuck!" Rafaela said. "You did that when you helped me take my sweater off."

"And did you like it when I brushed against your neck?"

"I loved it. If you were a girl I would have turned and kissed you."

"Exactly. I may not ever be able to use that information with you, but I know you like your neck touched. If I ever had sex with you, I'd make sure I touched your neck rather frequently because it turns you on. Sometimes, it's more obvious than that. 'Oh, keep doing that. Don't stop,' or in the alternative, 'I'm too sensitive right now. Quit licking me right there.' Of course, some people think that the person wants the licking to stop altogether, rather than I like what you're doing but not right there, not right now. You have to pay attention to all the cues someone is giving you, not just the verbal ones. I pay attention to that shit."

"So it's not just your big dick?" Cynthia said.

"I hope not. Quite a few people might have a big dick, but I hope that when push comes to shove, they're going to prefer me to a bigger cock."

"How big is his cock?" Rafaela asked.

"Over eight inches and quite girthy," Cynthia said. "It filled me up so good."

"Of course, everything I just told you could be applied to the guys who hire you as well as the girls. Pay attention to what makes a man's cock twitch, and you'll quickly learn what will make him ask to hire you time after time. Anyone can suck a dick, but doing it better than almost everyone else will make you stand out in a crowd filled with beautiful women, just as making a woman scream your name as she cums will bring you repeat business. You're not selling a cock sucking, you're selling a fantasy that you're his or her girl."

"Bullshit! You think you can lick my kitty as good as a girl can?" Rafaela said.

"Not better than all girls, but I'd be willing to bet I can do you better than fifty percent of the women you've ever been with, who frankly, being as young as you are, wouldn't know much more about licking pussy than I do."

"You just trying to get into my panties?"

"I'm not trying to break your gold star lesbian status by fucking you, but you should at least suck my dick if I make you scream during oral sex, so a blow job to completion seems like a reasonable bet."

Rafaela thought about that for a couple of minutes, then said, "Deal. I've got to admit I'm curious. Even if you're shit as a pussy licker, I want to see if you're close to good. I probably wouldn't have to pay off anyway."

"I'll make it even better for you. We both lick Cynthia to orgasm, and if she says you're better, don't even bother with the bet. It costs you nothing, but if she says I'm better, you let me lick your pussy, and if I make you scream, you suck me off and swallow my load."

"There ain't no way you're going to lick that pussy better than me, cowboy. I'll take that bet in a heartbeat."

"Do you have any problem with me starting, so you know what you have to do to beat me?"

"I was going to suggest that myself."

Great, as undressing Cynthia was going to give me clues to what turned her on.

"Stand up Cynthia, and I'll undress you now."

She stood up and I slowly removed her clothes, unveiling her to Rafaela as well as myself. I pretty much touched her all over as part of the process, paying attention to everything her body was telling me, whether she vocalized it or not. I already knew what Cynthia looked like, and I knew Rafaela would enjoy her as much as I did. She was keeping her muff shaved, so that was good.

Once she was naked, I led her to my bedroom, with Rafaela following along behind. Without undressing myself, I put my very best efforts into my oral seduction of the young beauty. I wanted Cynthia to enjoy it, and I wanted to have Rafaela wrap her luscious full lips around my cock. She was a stone cold fox and I wished she didn't bat for the other team, but damn, I was looking forward to licking her pussy in the worst way.

Taking my own sweet time, and I'm talking over twenty minutes here, I brought Cynthia to a screaming orgasm, and she squirted on me. That had happened to me a couple times before, so it wasn't completely unexpected, although it took both Cynthia and Rafaela by surprise.

"Damn, Danny. That surprised me," Rafaela said. "I'm worried that I might actually have to suck your dick. Not looking forward to it."

"We'll see. Cynthia gets to decide if I even have a chance to lick your kitty, so do your best, and we'll see how it shakes out."

While Rafaela got started on Cynthia's tasty snatch, I got a towel and wiped off my face. I didn't change shirts or the bed, in case it happened again. Cynthia was more sensitive now that she'd already climaxed, so she only lasted ten minutes this time before she orgasmed on Rafaela's tongue.

"What's the verdict?" I asked. "Who licked you better?"

"You were both better than anyone who's ever licked me before, but I have to give the nod to Danny on this."

"Shit!" Rafaela said.

"I've still got to make you scream, Rafi, so don't get all bent out of shape yet. Do you mind if I undress you?"

"I guess not."

"Cynthia still has to practice on you, so you'll need to be naked anyway," I said. "It's all good. At the very least, you should get some excellent oral sex, no matter what."

Rafaela smiled. "I feel like I've just been taken for a ride."

"I told you I was good. You just thought you were better. Maybe on another day, another woman, this comes out different."

I took my time undressing Rafaela, cataloging her sensitive spots. I already knew about her neck. I added a half dozen others I could play with on the way to the big O. She had great breasts, a lovely peach with a landing strip, but otherwise shaved close. Her ass looked to die for. Once again wishing she played on my side of the tracks.

Take whatever I did with Cynthia, and double it. I went to town on Rafaela. I didn't know if I'd ever be able to do this again, so I wanted to take full advantage of the dish laid out before me. I teased and tempted, bringing her close to release a half dozen times, without ever taking her over the edge. She was pretty much begging for an orgasm before she got one. She screamed loud enough two of my roommates were knocking on the door, wondering if someone was being murdered. Someone was sprayed, but no one got murdered. I got another soaking.

"Everything's fine," I said. "Just a nice orgasm."

"You're lucky it was the afternoon," Jack said. "You woke me like that at night, I'd have hurt you."

"Understood. Back to your studies, boys."

"Fuck me, Dan. That was great," Rafaela said.

"Have you ever had a better one?"

"Honestly, no."

"Do you want me to get naked, or just pull it out of my pants?"

"I'll tug your pants down to your ankles. Fuck!"

"While you suck, I'm going to give pointers to Cynthia, if you don't mind. She needs to get better at cock sucking too."

"Fine."

Rafaela unbuckled, unsnapped, unzipped, and pulled my pants down. Ii was already half hard, and climbing.

"You don't expect me to deep throat this monster, do you?"

"I'd be very surprised if you could, but don't worry about it. Deep throating a dick is not the goal here."

Rafaela started to lick. I wondered if it was the first cock she'd ever had in her mouth. It seemed like it.

"Remember, Cynthia, you're not just sucking some stranger's cock, you're selling a fantasy. You're not just a vacuum cleaner, you're a beautiful woman attached to one of the most versatile and facile things on your body, your mouth, controlled by the most important sexual organ, your brain.

"Regardless of what lipstick you wore on your date, apply some bright red lipstick before you suck your date's cock, something to really stand out. Don't just hoover his dick, tease it. Do some licking, some stroking, some sucking. The most sensitive area is the head. It will be arousing to see you completely swallow his cock, but most of the action should be around the head. I once had a girl give me a blow job and all she did was lick the little spot where the head joins the shaft." I pulled Rafaela's head back a second to show Cynthia where I meant. I releases her head again so she could continue. "It would be boring if that's all you did, so don't just do that, use all of his cock and his balls too. Lick and suck on them a little, just to change things up.

"Next, you want him thinking that you want and desire him, that it's not just a job you're getting paid for. So a little dirty talk is appropriate, but don't just sound like a whore. Make it a little bit real. Don't say, 'This is the biggest cock I've ever sucked.' Say something like, 'You're so hard. You must really be enjoying this. I'm enjoying it too. This cock is just perfect for me.' Do you see the difference?"

"Yes, I understand."

"Make eye contact frequently. You may not be able to look up adoringly in his face every minute, but keep looking at him while you're teasing. You can get a lot of feedback from both his expressions and his vocalizations. Are his eyes closed? Does he have his hand in your hair? Is he encouraging you to take him deeper? Is he moaning? Are his abs tightening up, his testicles climbing? Lots of little signals are given off and you should be paying attention to what they are."

"Have you ever sucked a cock?" Cynthia asked.

"Never."

"How do you know so much about cock sucking?"

"Because both pussy licking and cock sucking are similar, and because I know what I like. It's the reason Rafaela thought she could lick pussy better than I could. She has one, and she knows what she likes, but I suspect, she did you like she likes and didn't pay attention to what you like as much as I did. I don't know what having a pussy is like, so I had to learn, and I learned all women aren't the same. Some like one thing while others don't. I pay attention to what seems to be working, not what should work. I even know that different things turn me on, and different women do different things sucking a cock, and they can all be pleasurable when done in the right way.

"Lastly, don't make anyone cum right away. Let them get close a few times, but don't take them over the top. That's the reason both of your orgasms were so good. I could have made you orgasm sooner than I did, but I let the sexual tension build up longer so the orgasm would be better. Does that make sense?"

"Yes, perfect sense."

As I was explaining blowjobs to Cynthia, Rafaela was listening, and she started practicing some of the stuff herself. She was doing some sucking, some licking, including my shaved balls, some hand pumping, she was making eye contact. It was going from a pretty boring and useless blowjob, to something much better. I don't think she was going for the build up, because Rafaela would want it over as soon as possible, but it was definitely improving.

"When you lick Rafaela, you'll do the same things. Find her sensitive spots, but don't ignore the rest of her. Play with her boobs, touch her neck, she likes that. She has a sensitive anus, and I suspect she'd enjoy anal, but don't shove your finger up there without asking for her permission first. Recognize when she's close to her orgasm, but back off the first couple of times she approaches. Continue caressing, but don't focus on her clit, focus on something else she enjoys but won't make her cum." I moaned. "You're getting much better, Rafi. Good job."

"This is the biggest cock I've ever had in my mouth," Rafaela said. "You're such a stud."

I laughed and stroked her hair. "I believe you."

She smiled and went back to work.

"The last thing I'll tell you is that your client isn't there to make you feel good. You're not paying him or her. If you manage to enjoy it, great, but at the very least, he or she should. Give them what they want, and they'll appreciate what you did."

"I'll remember that."

"Are you getting close?" Rafaela asked.

"Two or three minutes away at your current level of expertise," I told her.

"Good, my jaw is getting sore." She went back to work.

I laid back and closed my eyes, enjoying the avowed lesbian sucking my cock. Her lips alone would tend to make her an adequate cock sucker. They were perfect, soft, smooth, pliable. She did seem to recognize when I got close, and finished me off with a sucking flourish, and I orgasmed, moaning as she drank my cream down, choking and sputtering a little.

"Thanks, Rafi. You really started to listen and it wasn't half bad."

"Yuck, sperm. Can I have a drink?"

"Water or beer."

"Beer."

I pulled up my pants and got her a beer. She drank half of it, then Cynthia practiced on Rafaela three times as I gave her pointers. I could tell she was getting a lot better towards the end, something which Rafaela confirmed when she finished the last time.

"I'm taking Rafaela out for dinner. Do you want to go," I asked.

"No. I better get back to Jimmy. I've got another date tomorrow night, and I have to see Julie on Saturday so she can see how my pussy licking skills improved. I might blow Greg again to see if I can get a raise. Thanks for the tips. You really are very good."

"I'll see you around," I said.

"I hope so. I wouldn't mind getting another nice fucking from you in the future."

"So, pizza?" Rafaela asked after Cynthia left and she was getting dressed, hiding all of those assets.

"What? Didn't you hear, I made beaucoup bucks last Saturday. How about DeStafano's for a steak dinner?"

"I'm not dressed for that?"

"Change. We've got time. My reservations aren't until six-thirty."

"You made reservations?"

"I did."

"For two or three."

"That was open to either," I said. "I guess it's two."

"No sex, right?"

I laughed. "We had all the sex I was expecting, and maybe more, since it was a bet. No, we're good. I'll pick you up at 5:45. Be ready."

Rafaela went back to her place while I showered, changed the sheets, and got into my suit again. I didn't use Greg's tie, as I had my own. I had to admit I looked spiff in my duds.

I called a taxi when ready, and he was pulling up in front of her apartment five minutes early. I went to the door and knocked.

Rafaela came to answer my knock in a nice little black dress, some three inch heels and stockings. She'd brushed out her hair after the sex and added make-up. She looked like a million bucks.

"Are you ready?"

"Yes. Treat me like you would one of your clients tonight, except for the sex."

"If you won't get catty if I treat you like a queen," I replied.

"I'll behave if you do," she laughed.

I walked her out to the cab and held her door, then went to the other side. I took Rafaela's hand. She almost pulled away until I said, "Pull your claws in, kitty cat. I'm just holding your hand."

She smiled and left her hand where it was, while I softly rubbed her knuckles. When we reached the steakhouse, I jumped out to get her door, paid the cabby and took her arm as we walked to the restaurant.

"Reservations for Bancroft, just two. Our third couldn't make it."

"Yes, sir, if you'll follow Margot, she'll take you to your table."

I took Rafaela's arm again and we followed our hostess to a small table for two. I held her chair for her and got her situated before taking my seat.

"Would you like a wine list, sir?"

"That will be up to the young lady. I'll have a Crown Royal on the rocks, please, and ice water, with lemon."

Rafaela took the wine list and glanced at the prices. "Is there an upper limit on what I order?"

"I'm not made of money, so let's say $200 a bottle."

Rafaela ordered a Cabernet which was around $150, and the waitress left us with our food menus.

"How about the food. How careful should I be?"

"We'll set the same limit on the food. I have another job tomorrow night."

"I feel like you're trying to butter me up before you put me on the spit."

I laughed again. "It's probably no secret I'm attracted to you, but I'm not one of those cavemen who think you're only a lesbian because you never met the right man. If you ever want to change your gold star status, I wouldn't mind if you considered me to do the deed, but I don't expect you to fall madly in love with me. Life doesn't work like that. You're funny and smart and I like funny smart women, but if you want to keep me in the friend zone, I'm good with that. If I get tabbed to train some more women to lick pussy, I'll keep you in mind."

"I never in my wildest dreams thought you could lick a pussy as well as I did."

"Hey, I've been doing it just a long as you have. I'm not an ignoramus. I can figure shit out."

The waiter came for our food order. Rafaela got the filet mignon and I got a New York strip. She got the rice, I got the au gratin potatoes, and we both had the seasonal vegetables. She'd finished about half of her wine by the time our food came.

We continued to chat about things, school, our majors, some about being an escort.

"Do I have to do dick if I worked as an escort?" Rafaela asked.

"You probably won't get as many jobs, but you can specify women. You probably won't need the pussy licking training, but remember what I told Cynthia. It's not all sex. In fact, you may not even be attracted to someone, but they might still appreciate sex. You should be ready for that."

"I can refuse if I want?"

"Yes. It's illegal to charge for sex. Your clients are being charged for your time. How you choose to spend it is up to you. The tips may very well depend on the sex. If you do someone good, they should pay you more. If you don't do them at all, you might not even get a tip. They're related, but not connected. You don't ask for additional money for sex, or suggest that you be tipped for sex. That could get you arrested. You go out on a date, and then the date's over, and if you enjoyed their company, sex might follow, and if it follows, you should get tipped more. If they don't tip well, you won't go on another date with them. I can give you Julie's number if you want to talk to her."

"I think I'd like to speak to her if she'll talk to me and I know I don't have to date guys."

I sent her Julie's contact info. When she left to use the ladies', I stood, when she returned, I stood again and held her chair. I was the perfect gentleman, all night long. I think she enjoyed the attention, despite my gender.

By the time we left, she'd knocked off the whole bottle of cabernet. I teased her about it.

"Still trying to get the taste of sperm out of your mouth?"

She laughed. "No, it's just really good compared to what I normally drink, and it went perfectly with the meal."

I hailed a taxi, gave him the address and held Rafaela's hand once more. She didn't pull away at all, and I thought that was fine, then I realized she'd fallen asleep, or passed out. I canceled her address and gave the driver mine. When we arrived, I helped her out of the cab and carried her to my apartment. Dante let me in when I kicked the door softly.

"Who's the sleeping beauty?"

"A girl from a couple of my classes. She had a little too much to drink. Knocked off a whole bottle of Cab herself. I need to get her to bed."

"Need any help?"

"No, Perv. I've got it. I'll be sleeping on the couch tonight. Don't forget and sit on me."

"She's a cutie."

"Also a lesbian, so don't mess with her."

"Why'd you take her out?"

"She helped me with something earlier, and I offered her dinner for the help."

I carried her to my room, Dante opening the door for me, then I kicked him out. I couldn't leave her in her LBD, and I had seen her naked already, so I took off the dress and hung it up on the back of the door. I left the rest of her clothes on, including her nylons, and tucked her in. I put the trash can next to the bed in case she might need to puke, then I grabbed some sweats to sleep in, plus my toothbrush and toothpaste, and turned off the lights and locked the door behind me. The locks were easy to overcome, but I didn't think anyone was that desperate, and I was sleeping fifteen feet anyway. I called it a night.

******

Rafaela stumbled out of my room around eight, wearing my robe, which was huge on her.

"Oh, my aching head," she mumbled.

"Bottle of water in the fridge, Extra Strength Excedrin on the counter next to the coffee, which is hot, if you want some. Water is better for you, however. You need to rehydrate. Coffee won't."

She tiptoed to the kitchen like she was afraid of making noise, grabbing the water and a couple of the pain tablets, then sinking on the couch beside me while guzzling half of the water.

"Why am I at your place?"

"I didn't know what to do with you once you passed out. Didn't know if anyone would be at your place to let me in, and I figured you'd be safer here where there was someone to look after you."

"We didn't..."

"No. I promised to be a gentleman, and I was, except for the dress, which had to come off. I figured I'd seen everything already so bra and panties weren't a big deal."

"I think I missed my first class."

"Do you really feel like going to class now?"

"Fuck, no."

"Why don't you go lie down some more. If you feel like it later, I'll give you a back rub."

"Really?"

"Hey, if I didn't molest you while you were passed out in my bed, I wouldn't while you were awake and able to kick my ass."

"Where did you sleep?"

"The couch. I didn't want you to wake up with someone beside you in bed."

"Thanks for taking care of me. Sorry I was such a lush."

"No problem. It's not every day you can drink a $150 bottle of wine."

"Yeah," she ruefully grinned. "Good stuff. I'm taking your suggestion and going back to bed."

"Finish your water. It will help."

"Got it." She held up the water bottle. "Nighty-night."

I went back to studying before I left for my 10 AM class.

******

I came back at noon, bringing a Big Mac and QPC. Rafaela was still in my bathrobe, but now on the couch with another bottle of water, her feet tucked under her, looking a little clearer than the last time I saw her.

"Greasy food?" I asked, holding up the bag.

"Whatcha got?"

"Big Mac or Quarter Pounder with Cheese, both with medium fries."

"Do you have a preference?"

"Nope, You can pick your poison."

"Big Mac. I like the special sauce," Rafaela said.

"I gave you special sauce yesterday and you didn't like it all that much."

Rafaela laughed. "Not the special sauce I'm used to."

I handed her the Big Mac and her fries.

"How's the head?"

"Better, the water and Excedrin helped. Almost normal."

We didn't say much as we ate. As we got to the end of our mini meal, she asked, "About that back rub?"

"What about it?"

"Can I get one?"

"Definitely."

"No strings?"

"No strings."

She got off the couch and took my hand, leading me into my bedroom, and closing the door behind us.

"You'll need to take the bra off unless you want baby oil stains all over it," I said.

While she looked at me, Rafaela reached behind her and unhooked the bra, dropping it when she was done, showing me her tits, those beautiful tits.

"Nice. I know you appreciate the female form, so you must know those are great breasts, right?"

"I know."

"So go lie on the bed and cover them up."

"Are you going to strip?"

"Too risky. I think I'll keep my clothes on. I wouldn't want to offend you with my dick again."

"You can take your pants off. Maybe the shirt too, Leave the briefs on."

She didn't wait for me to disrobe, getting on the bed and lying down, her head facing the wall, not me. I got the baby oil and rubbed her back. I gave her a damn good back rub, too. Not as good as the cunnilingus she had earlier, but good.

"What time is your date?" Rafaela asked.

"Six arrival time. Dinner and an art exhibit to follow. Black tie affair."

"Would you give your date a back rub?"

"If she wanted one, sure."

"How old is this one?"

"Forty-three, I believe."

"Where are you going to eat?"

"Don't know, someplace in Manhattan."

"Do you enjoy it, being an escort?"

"Well, I've only had one real date, but the woman who told me I should become an escort wanted to be the first one to tip me for a weekend. She bought me lots of clothes and gave me a thousand on top of it. I have so far. Everyone's been pretty nice."

"Are you going to keep doing it after you graduate?"

"I'm not sure. Depends upon what my options are, and how well it's paying."

"You're very good at rubbing backs."

"I like doing it, so I practiced a lot."

I finished up and gave her buns a couple taps. "All done."

"Can I ask a favor?"

"No law against asking."

"Would you lick me again?"

"I'd love to."

"Is it going to cost me anything."

"Are you suggesting paying for sex?"

"No, more of a quid pro quo."

"I thought you hated the taste of sperm?"

"I do."

"So I was that good, huh?"

Rafaela laughed. "You were okay."

"Just can't admit a guy could possibly be as good as a girl, can you?" I laughed.

"Fine, you were great, the best ever. What do I have to do to get another one?"

"Nothing. This one's on the house. I should save my meat for my date, don't you think?"

"Please, save it for your date. You have to pay for last night's meal somehow."

Rafaela flopped over onto her back. I grabbed the tops of her panties.

"May I?"

"You can't lick me until you do," she replied, matter of factly.

I drew her panties down her legs and gave Rafaela another screaming orgasm, although she shoved my pillow in her mouth to keep from disturbing anyone. She didn't squirt this time, although her pussy was flooded. She seemed to enjoy it just as much. She even took a shower with me, although we sort of stayed away from each other except for back washing. She went home afterwards, no bra or panties because she was clean, and they weren't, but it was only a couple blocks. I finished studying for the day, then got ready for my next date.

*****

I would work with or see Cynthia on occasion. She turned out to be very popular, and after her training with me, got bumped up to $175 an hour, though she hit $200 without much more effort within a couple of months. I never fucked her again, except once after Jimmy died. He got pneumonia around five years after Cynthia became an escort and passed away. Cynthia married one of her clients around two years after Jimmy died. I guess she seemed like a girlfriend when she dated him. To the best of my knowledge, they're happy and have two children. I wondered if Jimmy ever found out about what she did for a living to stay married to him.

Rafaela also became an escort at Elite. She only did girls for six years, and she was immensely popular with them. After the first six, she started doing couples, though never single men. When she decided to do couples for the first time, accepting her first couple for a week to one of the Caribbean Islands. Since she knew she was going to be giving it up to the husband anyway, she let me take her cherry, such as it was. It was the only time I had penetrative sex with her, although we made a weekend of it, fucking like rabbits. I made sure I cleaned her pussy every time I made a deposit, which she loved.

But every so often, when she was between girlfriends, she'd ask me to lick her. I never turned her down if I wasn't busy, and I probably consumed more of her pussy juice than anyone but Alberta. I never asked her to blow me again, nor did I bet her, because she wouldn't have taken the bet anyway. She often slept naked in my bed when I did her, and that was pretty sweet. She quit after three more years, marrying a woman she'd met while out on a date. They moved away from New York. I attended the wedding, but never saw her again. I missed licking her pussy, as well as her friendship.

Up next, is the youngest woman I ever escorted.

******