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Sex games

Like Mother, Like Daughter!

Author: Quillpen

Date: 29 July 2026

Prostitution, massage, First Time

  • Font:

Êàðòèíêà ê ðàññêàçó

Part One

My name is Clifford Wagner. When I was a teenager in the late 1970s, I was a normal, healthy male who desired intimacy with females. Unfortunately, I was not a very attractive lad. I had a crooked nose thanks to a baseball colliding with it when I was ten years old. My chin was a bit too large for my face, as were my lips. To say I was no girl’s dream date was a huge understatement. I was very good in school, but my academic achievements had absolutely no appeal to any of my female peers.

In locker room conversations, I often overheard stories from my male counterparts about their various romantic and sexual conquests. In retrospect, I suppose a lot of them were greatly exaggerated. Nevertheless, I felt left out. I suppose I was jealous of them. I couldn’t even get a girl to go on a simple date with me, much less have a sexual relationship with one. It bothered me. I thought I might go through my entire life without ever sampling the carnal delights of a compliant gal.

One day I happened to be watching a comedian on one of the late-night talk shows. He was joking about how much a prostitute costs compared to the money that a male typically spends on a classy date. He noted that sex with a hooker was a sure thing, but that was far from the case with a girl you treat to a night out. “If you are only interested in sex,” he deduced, “a call girl is the best way to go. It’s a simple monetary transaction. There’s no guessing or hoping. You’ll get what you pay for no matter who you are or what you look like.”

It was supposed to be a funny remark, but that comedian was absolutely right! To me, it was a eureka moment: Courtship rituals often paid no immediate dividends. (Often the benefits never arrived at all.) Why not just pay for sexual favors up front, get them, and go home happy? Accordingly, beginning at age 17, I sought the services of professional sex workers whenever I felt horny—which was quite often.

In the 1980s, finding harlots required a bit of detective work. There was no internet at the time, of course, but there were classified ads in newspapers that listed “escorts”—a common euphemism for hookers. Often prostitutes would leave stickers in public telephone booths that had their phone numbers and the services they provided. One of those stickers got me my first romp. It came on April 17, 1981 with a woman who called herself Candi. (Who knows what her name really was?) I went to her apartment. She was likely twice my age and not especially attractive, but neither was I. I told her honestly that I was a sexual newcomer and she treated me very kindly. When I ejaculated onto her breasts, I felt like I had gone to heaven. To heck with traditional dating! (I wasn’t doing much of that, anyway.) From that date forward, I’d be spending my disposable income to hire pros. I began averaging a romp with a hooker about once a month. That comedian was right. It really was more economical than romancing a female and hoping to get laid.

By the time the mid-1990s rolled around, massage parlors were legal in my part of the world. I was curious enough to try the first one to open in my suburban hometown. When I entered the building and climbed a steep flight of stairs, I was met by a forty-something woman named Daphne. She was wearing a black negligee and not much else. I explained I had never been to a massage parlor before, but I wanted to have some “naughty fun.”

Daphne gave me the rundown of how the business operated: There was a mandatory "room fee" that paid for a 30-minute sensual massage with one of the employees. If I wanted unspecified “extras” I could negotiate the price and the service with the girl. I was informed that such bonus services would make the time limit disappear. I said that sounded fabulous to me.

Daphne led me into a waiting room where four other horny males were waiting for their “sexual releases.” We were a cross-section of ages. I saw a nervous someone who was probably just 16 or 17 (and shouldn’t have been allowed to enter if the laws about such places were strictly enforced). I saw a grey-haired fellow who had to be pushing 70. Good for him! The other two customers I estimated to be in their thirties, like I was. There seemed to be an unwritten rule about patrons not talking to one another, so I followed the pack and didn’t say a word. I just patiently waited my turn, knowing there were four anxious people ahead of me. I had no clue how long I would have to wait before getting to the front of the queue.

Part Two

It took almost exactly one hour for me to get what I had come to this place for. I was now the only client in the waiting area. I noticed that the four fellows who had been ahead of me seemed to be happy campers when they departed the premises. I took that as a positive sign.

I was told by Daphne that I had my choice of three ladies who all came out to show off their wares. (She was one of them.) I quickly chose Valentina, who seemed to be about my age. She was wearing a sexy, red negligee. She was a little bit on the small size, but Valentina had oversize breasts that caught my attention. She led me into Room #3. Valentina had a foreign accent, likely eastern European, that was an added turn-on, not that I really needed to be aroused. My penis had been stiff since the moment I’d selected Valentina to be my masseuse. With dazzling strawberry-blonde hair down to her shoulders and sexy legs, she certainly was an appealing gal—and I hadn’t even seen Valentina’s best parts yet!

She immediately got down to business. Valentina said for a fully nude, body-slide massage culminating in a “release”, the total cost would be another $80. I told her that price was fine and gave her four $20 bills. She told me to disrobe and use the shower after which I was to lie face down on the mattress that was situated at the end of the room.

Valentina absented herself from the room and came back ten minutes later in an even skimpier outfit than she had been wearing before. I can’t describe it because she didn’t have it on long enough for me to get a good look at it. I was lying on my stomach, but I could see everything my masseuse was doing thanks to several mirrors on the wall. She got behind me, between my legs, and squirted oil on my back. At first, Valentina used only her hands to massage every part of my back from my shoulders to my waist. Then she dropped her lovely nude body on top of mine and began sliding it up and down. That was erotic and exciting! All the while she was engaging me in a polite conversation which I wasn’t really interested in having with her.

Then she said something wonderful to me: “Time to turn over!” I obeyed with alacrity.

Valentina repeated her body-slide, this time moving her tits from my navel to my face. “You can touch them if you want; that’s allowed.” I thanked her for telling me that, so I gladly cupped her lovely jugs and played with her nipples until they were rock hard. “May I suck on them, too?” I asked with hope clearly in my voice. I was told that was all part of the extra $80 I had paid.

When Valentina squirted more oil on my scrotum, I knew a hand job—known as a “release” in massage parlor lingo—was next on the agenda. I continued to lie on my back while she gave my hard dick some serious tugs. I asked Valentina for permission to sit up so I could continue fondling her breasts while she stimulated my penis. It was granted. Eventually, nature and biology terminated my fun. I strongly ejaculated. Most of my jism landed on Valentina’s torso. It was extremely sexy. She didn’t have to do it, but Valentina told me while she was cleansing my penis with a warm cloth, “Once you come, that normally ends the session. However, you’re such a nice guy, Clifford, let me lie beside you and we can snuggle for about 20 minutes.” That was a terrific offer, which I happily accepted. I used the time to caress Valentina’s bum and do some more tit sucking. That day I became a lifelong fan of massage parlors.

Part Three

I started going to the massage parlor instead of hiring hookers via classified ads. I found these businesses to be fairly accommodating. Normally, I was quite happy to lose my load via a hand job, but occasionally I’d ask for full sexual intercourse. About 80 percent of the time, the masseuse would say no, but occasionally I did find a compliant girl. There was a rapid turnover in employees, which I understood was typical at massage parlors. After a while, the quality of the masseuses waned, the prices got steeper, and I was leaving the establishment not nearly as satisfied as I was when Valentina was servicing me. She was long gone by then.

I returned to scanning the classified ads. This time I found a masseuse named Carly who operated out of her own house in the city next to mine. She offered “full body massages at reasonable prices” with “extras available.” I figured Carly’s services were worth a phone call, so I made an inquiry.

I was impressed immediately by Carly’s bubbly personality and eagerness to see me. She gave me a description of herself: 37 years old, brunette, 5’5”, slender body but luscious boobs. (Yes, Carly used that adjective to describe her breasts!) She even offered a “free extra” to entice me if I were to come to see her that Thursday afternoon in a specific time slot. I agreed, made the drive, and knocked on her door at 2 p.m. sharp.

Carly was basically average-looking, but what a terrific masseuse she proved to be! She had a proper massage table to do her advertised work—plus a small bed in the same room for her extra services. Her work was even better than Valentina’s was a couple of years before, which was quite a feat. Carly used her mouth on me, too—and not just for kisses! I was about to ask her for full vaginal sex, but she beat me to it. She mounted me and said, “This is your free extra for answering my ad today!” She gyrated and bounced on my erect dick for about three minutes before I fired my load. Carly’s sensational services had certainly relaxed me, but now I was exhausted from such a huge ejaculation.

When I was preparing to leave as a very satisfied customer, I noticed a framed photograph of a girl who looked to be about 11 years old on a table. “That’s a pretty young lady,” I commented. “Is she a relative of yours?”

Carly replied, “That’s my daughter, Faith. She’s my pride and joy. She’s in the fifth grade and doing well in school. She has a dental appointment today, so I’ll be picking her up soon. Thanks for filling in the gap between now and then, Clifford. You are a gentlemanly client.”

“I’d like to make another appointment with you, Carly. Would the same time next week work?” I inquired. Carly checked her appointment book and said that would be fine. I told her if she serviced me just as well in seven days, I’d likely make it a weekly ritual to pay for her fine services.

“I really do love having satisfied customers!” she told me as I headed to my car.

Part Four

That’s exactly what happened. For some reason, Carly and I clicked. I was always hard as a rock when she worked on me and I always climaxed with a tremendous cum shot. About half the time I opted to pay extra to screw Carly’s pussy, but it was definitely worth the added expense. Her vagina just seemed to grab my dick and drain it thoroughly. I had a standing appointment with Carly each Thursday at 2 p.m. I looked forward to it. On some level, I think Carly did, too.

One Thursday I arrived at my usual time. I noticed Carly’s driveway was without a car—which was unusual. I knocked on the door and was surprised to see a teenage girl answer it. She looked vaguely familiar—and then I realized why. She was the girl whose framed picture I had seen for seven years. It was Faith, Carly’s daughter.

“Hi, Clifford. That’s who you are, right? Come in, please. Let me explain what’s happened today,” she said to me.

Faith told me everything. “It was supposed to be a routine Thursday,” she said, “but my mother got a telephone call at about 9 a.m. reminding her of a longstanding appointment with a medical specialist at 2:30. It was made two years ago, but my usually diligent mother somehow neglected to put it in her datebook. If she cancelled it, she’d have to wait two years for another appointment. She knew she had you and a pair of other customers booked for today. She cancelled the other two, but insisted that you be taken care of. You’re her favorite customer, Clifford, in case you didn’t know it.”

My mind was trying to absorb everything I had just been told. The first thing that occurred to me was to find out what was ailing Carly. She looked to be in fine health to me.

“It’s nothing that’s going to kill her,” Faith told me. “Her right wrist often aches and swells, so she’s hoping this doctor can diagnose the problem and do something to cure it. (The comedian in me was tempted to say that maybe giving hundreds of hand jobs a year had put a strain on it, but I kept that quip to myself.)

I glanced at my wristwatch. My next question was an obvious one. “Faith, how can your mother service me if her appointment is less than 30 minutes from now?”

Faith surprised me with an unexpected answer. “Mom suggested that I take her place with you.” Faith handed me a hand-written note her mother had left for me and said I should read it. It read,

“Clifford: Something has come up and I won’t be here for your 2 o’clock time slot. I am sorry because I do like our sessions together. My daughter, Faith, will explain to you where I am. I have asked Faith to take my place with you. She is taking the second half of the school day off to accommodate you. Faith is 18 now. She is learning the massage business from me. She’s already had two clients who seemed to like her youth and her enthusiasm. I hope you will be #3. If this plan doesn’t work for you, you can simply go home with my apologies. If it does work, however, just pay Faith the amount you normally pay me. I think you’ll get your money’s worth. Either way, next Thursday when I’m back for our weekly session, I’ll throw in a free fuck for you for having to put up with any inconvenience. Kisses from Carly.”

I set the note down, took one look at Faith, who was a real cutie, and said, “Count me in!” I promptly paid her $100 plus an extra $50 for a fuck. I had never screwed anyone that young in my life before, so I figured I’d pay more to experience the carnal thrill of bedding a high school student with her mother’s blessing.

Faith, a brunette like her mom, began shedding her clothing. She had a fairly nice figure for her age. Her boobs looked exactly like her mother’s set did. Faith did not have a shaved vagina, however. Her slightly hairy bush served to turn me on, though, so everything was good. I got onto the massage table, face down and let Faith do her thing. For someone with just two previous clients, Faith was doing a marvelous job with her hands and every other part of her sexy, young body. Mom had taught her well—including what to do when I flipped over onto my back! I had a great time receiving Faith’s body-slide and sucking on her teenage tits.

“Do you want to go to bed and have a fuck now, Clifford?”

I chuckled and said, “That’s a silly question, Faith! Of course! What could be better than that?”

I decided to give Faith a good fucking because who knew when I’d ever be sharing a bed again with an 18-year-old, especially one as attractive as she was. I lifted Faith off her feet, which surprised her, and promptly carried her to the bed. I pried open her legs, fondled her vagina for a few seconds, and then I climbed aboard. Faith’s pussy was as tight as I’d hoped it would be. I could not have asked for a snugger fit from a girl her age. Overcome by lust, I drilled it, plowed it, slammed it and ravished it. The best part was that Faith smiled the entire time she was being impaled with my throbbing rod. What a girl she was! Faith absolutely loved my rough approach to coitus! Somehow, I postponed my ejaculation for ten minutes before firing my load of semen—a huge one—into Faith’s warm crevice. It was a truly wonderful sensation, without a doubt the best $50 I had ever spent in my lifetime.

Faith was in no hurry to shoo me out of the house. I had nothing on my schedule either, so we, by mutual agreement, stayed in that bed together cuddling and kissing. We were there until her mother came home a few minutes past 4 p.m. For fun, we allowed Carly to find us happily conjoined.

“Well, Clifford, I see Faith was an adequate substitute for me today,” she deadpanned.

“Yes, indeed!” I replied. “She was great at everything and has a tight, young pussy that is out of this world!” I added, “It does present a problem, though.”

Both Carly and Faith asked me almost simultaneously what the problem was.

“My financial budget,” I said. “I’m going to have to rethink it because I want to continue with both of you on a weekly basis. It might require me to go without food one day a week, but that’s a sacrifice I’m more than willing to make for this type of extreme pleasure!"


1725   41 17004  11   1 Rating +10 [5]

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Comments 10
  • GreNreNor
    Ìóæ÷èíà GreNreNor 1767
    30.07.2026 17:03
    This story definitely deserves a 10 from me. It was hot as fuck 😍

    Although, the only confusing part was about Faith’s age, as Carly first mentioned her being in 5th grade, being 11 years old. So does that mean there’s like a 7 year gap between part 3 and 4 or am I wrong?

    Answer 1

  • Quillpen
    Ìóæ÷èíà Quillpen 5039
    30.07.2026 18:45
    Thanks for the kind compliment. I'm glad you're enjoying my stories asa mmuch as you do. Yes, there is a seven-year gap. The rules of this website don't allow for descriptions of sexual activities with minors. I often have to alter my original stories when I post them here.

    Answer 1

  • GreNreNor
    Ìóæ÷èíà GreNreNor 1767
    30.07.2026 18:51
    Okay, that makes sense 😉

    Answer 2

  • Quillpen
    Ìóæ÷èíà Quillpen 5039
    30.07.2026 18:57

    I'm going to recommend two of my favorite stories for you. They are both on this website. They are "Susan and Gatsby" and "Finally Getting Janet". Both are strongly based on classmates of mine from my school days.

    Answer 1

  • GreNreNor
    Ìóæ÷èíà GreNreNor 1767
    30.07.2026 20:35
    Nice. I’ll check them out

    Answer 1

  • Maisie
    Maisie 2101
    30.07.2026 20:26
    They should let you keep the age as intended. We’ve literally cum here for the taboo aspect.

    Answer 2

  • Quillpen
    Ìóæ÷èíà Quillpen 5039
    30.07.2026 20:57
    If it were up to me...but it's not

    Answer 1

  • Maisie
    Maisie 2101
    30.07.2026 21:03
    It is only a number after all.

    Answer 1

  • Quillpen
    Ìóæ÷èíà Quillpen 5039
    30.07.2026 23:39
    I agree when it is fiction. Doing the horizontal hokey-pokey with someone's whose number is small can get you into big trouble in real life.

    Answer 0

  • Maisie
    Maisie 2101
    30.07.2026 23:41
    Oh absolutely. Goes without saying.

    Answer 1

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