Our Special Services (Part #2)

This is a sequel to "Our Special Services". Five high school boys who can't find summer jobs decide to create their own. They form a gigolo service!

Author's Note

This is a continuation of a story titled "Our Special Services". You are highly encouraged to read the first part in its entirety. If you choose not to do so, here is a brief summary...

It is the spring of 1982. Five 18-year-old Canadian high school students are having trouble securing employment for the summer. One of them, the highly sexually active Timmy, discovers by accident that there are many women who are widows, divorcees, plus lonely or unattractive gals who actively seek intimacy from young, healthy males. (A 45-year-old widow friend of his mother happily paid Timmy $100 for a thorough fucking.) Timmy figures that he and his four closest school friends (Johnny, Scott, Mike and Warren) ought to form a gigolo service to satiate such desperate women. Timmy easily sells them on the idea. They brand themselves as the ISF Boys; the abbreviation stands for "I Satisfy Women". The operate their enterprise out of Timmy's brother's vacated apartment. They place an ad in a local newspaper which immediately attracts attention. A radio interview creates even more interest. At his first assignment, Johnny, the story's narrator, has a marvelous time bedding a local 26-year-old single woman who is slightly on the homely side, but more than makes up for it with a fabulous body and an eagerness to excel in bed.
Johnny also narrates Part #2.

Part One

One week into the ISF's existence, all five of us high school gigolos had been busily screwing women of all ages and sizes, making money off it, and generally having the time of our lives. None of us had had a single bad experience to recount.

We learned this was the case when Timmy called for a meeting early on a Sunday morning just to get everyone's opinion on a number of topics. We all sported huge smiles and pockets full of money. With Timmy's guidance, we had stumbled into a dream job.

We all had plenty of anecdotes to share with each other. Scott started them off. He said to us, "I had a 42-year-old client who insisted that I come in her nose!" We all laughed heartily, but Scott insisted his story was absolutely legitimate. He continued, "She apparently liked the smell of a man’s semen, so she told me to come on her face and specifically aim for her nostrils. That seemed just a wee bit on the weird side, but I did it anyway."

I followed Scott with my favorite tale. I excitedly told my friends and colleagues, "One of my clients was supposed to be a 39-year-old single mom, but when I showed up at her home, she had booked my services not for herself, but for her 14-year-old daughter. I learned it was a reward for her improving her math mark at middle school."

Warren immediately interrupted me. "Our clients have to be at least 18 years old," he reminded me, "so I hope you walked away from that tricky situation, Johnny."

I immediately looked at Timmy, whom I knew had a definite fondness for young poontang. We both had incredulous expressions on our faces.

"Warren," Timmy said, "with your ridiculous puritanical outlook on life, I sometimes wonder how you managed to become my friend. I'd say Johnny hit the jackpot. I wish I had been him. Still, I have a hunch he did what I would have done. So how did it feel to screw a middle-school girl, Johnny and get paid well for it?"

"Bloody fantastic!" I shouted, after which Timmy gave me a high five—and Warren gave me a severe look of disapproval. My other two friends just smiled at my good fortune.

We had all acted as the ISF Boys booking agent at least once so far—and there were some highly amusing stories associated with that job. When I was answering the phone one day, a client specifically requested the sexual services of “the high school boy with the big dick.” I told the caller, somewhat immodestly, that her description “had narrowed down the list of our potential providers from five…to five!”

Timmy recounted an amusing tale of his own. One night, a fiftyish woman called to ask, “Can one of your high school boys make love to me better than my late husband Leonard?” Timmy paused and said to her, “Well, we can’t guarantee that specifically—only that he’ll do his best.”

“That will be just fine,” she said. “Leonard was lousy at sex!” Warren serviced her and she was apparently delighted by the outcome.

There were also some serious issues for us to discuss at our special meeting, which soon became a weekly ritual. It was determined that 100 percent of the money any of us received for performing our sexual services would be subject to the 15 percent fee we were required to pay to whoever was the booking agent that night. That included any and all gratuities. That made sense because we were free to charge basically whatever we wanted and include extras. Scott had a strange situation where his $80 fee was paid to him with $40 in cash plus a second-hand typewriter! (He agreed to the deal because he knew he could resell the typewriter for a quick profit.) For some reason, Scott thought the value of the typewriter ought not to be included in the calculation for the agent's percentage. All four of us disagreed with that logic. Scott stupidly chose to argue the point with a silly comparison. He said it was no different from when Mindy, my first client, gave me a soft drink before we began our session of fucking.

"Really, Scott? You're actually trying to equate basic common courtesy with getting a typewriter as partial payment for your services?" I asked with incredulity. He was, so we put it to an official vote where Scott lost, 4-1. He was required to cough up another $6 to the agent that night, who happened to be Mike.

From the money we were siphoning from the agent’s fees, we also decided to buy an answering machine for the office solely to pick up any and all telephone calls that were coming in during the wee hours of the morning. Apparently, there were plenty. The first night we had the answering machine installed, it picked up 11 calls between 2 and 6 a.m. Timmy returned every single call. Nine of those messages resulted in appointments with customers who were very satisfied at the end of the day. We had made a wise investment!

Part Two

We had all done our best to conceal our identities, except for Timmy, of course. He absolutely savored being a famous teenage gigolo. The rest of us, despite loving our new jobs, didn’t generally go around bragging about it to other people—only to each other. School still had a month to go before summer vacation and seemingly everyone in the twelfth grade knew that we five were paid sex workers. Some of us got scorns and dirty looks, mostly from girls. Some of us got high fives and handshakes, mostly from boys. Once I was heckled in the hallway from a voice I didn’t know as I passed by a classroom. “Hey, Johnny,” someone shouted at me. “What’s it like to screw a 50-year-old widow?”

I calmly retreated two steps and addressed all and sundry, “It’s about the same as screwing a 50-year-old spinster, I suppose. The widow is usually more grateful, however. The pay is exactly the same, though.”

Being famous—or infamous—often has its rewards. Being known to my classmates was about to get me an excellent booking from someone I had been acquainted with for years but never really knew. It was the night I agreed to accept Jenny Matlock as a client. She had been a classmate of mine since the first day of kindergarten in 1969.

Jenny was one of those classmates who can be alongside you during your entire elementary school career and make almost no impression. Out of curiosity, I later went through my class photos from kindergarten to grade eight and discovered Jenny had been in my class seven of those nine years. We may have had three significant conversations during that whole time. All of them pertained to group work we had been assigned. I had no social dealings with Jenny ever—until the phone rang that Friday night when I was the group’s booking agent.

“Hello,” said the caller. “Can I request a specific one of your male service providers?”

I said hello in return and pointed out that we only had male service providers, and yes, she could certainly ask for any specific one of us.

“Yeah, I knew that already,” the voice said. “Okay, then…I want to book time with Johnny Easton. That would be great if it could be arranged.”

“That’s very flattering,” I said sincerely. “I’m Johnny Easton. May I ask whom I am speaking with?”

There was a bit of a long silence. For a moment, I was afraid I had spooked the caller, and she had hung up on me. After a few awkward seconds, she said. “You know me. I’m Jennifer Matlock. We started kindergarten at the same time nearly 13 years ago.”

I replied, “Jennifer Matlock! Wow! How lovely to hear from you…and how lovely that you want to have a sexual encounter with me! Of course, I’d be delighted to oblige your sweet request.”

There was another long silence. “I hope you are being serious, Johnny,” Jennifer said rather sternly. “I had to muster a lot of courage to make this phone call. I had no idea you’d pick up the phone when I called. I figured you guys would have had a professional answering service.”

“Nope, we answer our own phones,” I informed her. “Does that make us an amateur answering service?”

“You still have the same sense of humor, Johnny,” Jennifer said kindly. “That’s why I’ve always liked you. To be totally honest, I’ve liked you since Day One.”

“You have? That’s news to me,” I told her.

“I am a shy girl by nature,” Jennifer responded, becoming more serious by the moment. “I can never be forthright and just tell boys that I like them and want to date them. But since I heard that you are now sort of a professional escort—if that’s the correct term—I figure I’m free to tell you whatever I want to say since I’m paying for your time.”

“That’s one way of looking at it, Jennifer,” I noted. “You know something, Jennifer, I love the quiet, demure type of girl best. Perhaps we should have gotten together years ago. We could have made a nice couple.”

Jennifer asked me what my going rate was. When I said, “It’s $70 for any and all things you can possibly imagine,” she wanted to know what the time limit was. I told her there really wasn’t one. I’d stay long enough to please her, please me, and then some. If I was having a truly terrific time with her, I’d stay with her for numerous hours.

Jennifer enthusiastically announced, “Let’s plan on that! I’m home alone all weekend. Johnny, can you come to my house tomorrow at 12 noon?”

“Sure, I’ll mark it on my schedule!” I cheerfully said as I wrote down her address. “I’m looking forward to it!”

“Well, I’ve been looking forward to it since we were square dancing partners in the second grade,” Jennifer noted. “I had a big crush on you back then, Johnny. Now, finally, I’ll be able to do something about it!”

Part Three

There was nothing especially noteworthy about Jennifer Matlock except that she was quite petite in stature. She had been one of the smallest girls in my class every year. I sometimes imagined a strong breeze would have blown her over on some windy days. She had blondish hair that was usually cut short. She had an average face and less than an average build. She could have accurately been described as flat-chested. I couldn’t say much about her personality because over the years she seldom raised her hand in class to ask a question or make a comment about a lesson. We all had to make speeches and oral presentations to the class from time to time, but I don’t recall any of hers at all. The telephone conversation we had in which she booked this unexpected sexual tryst was, by far, the longest and most in-depth talk we’d ever had. For some reason, the mere thought of my bedding someone who was “a familiar stranger” turned me on! Go figure!

According to my diligent records, Jennifer was my 23rd client since Timmy began our ISF Boys team in April. The first 22 were all wonderful lays. I’d enjoyed screwing every last one of them. Some were better than others, of course. (The middle school cutie who got me as a gift from her mom was the best fuck I’d had thus far!) Jennifer Matlock was the first case, however, where I knew the client before arriving at her home or at a hotel. I decided to bring Jennifer a box of chocolates as a gift. I figured such a goodwill gesture could not hurt my cause. As with most of my other clients, I arrived at my destination by city bus because I did not have a car of my own yet. Jennifer’s house was about three-quarters of a block away from the Sanderson Street bus stop. I was about five minutes early when I saw Jennifer’s house number—27. She was eagerly awaiting my arrival.

I opened the door and handed Jennifer the box of imported chocolates. She set them on a table, smiled, said thanks, and basically leapt into my arms to give me one of the best kisses I had ever gotten in my life. Wow! This was one keen and enthusiastic girl I was holding. Jennifer was wearing a pair of sky-blue shorts. I immediately began to caress her bottom. It was a small tush, but it was a high-quality one. As our lengthy kiss edged toward a full minute, I began to reposition my hands, so they were now up her legs and inside her shorts and panties. My fingers began to wander to her most private place.

Jennifer ended the kiss to announce, “Well, it appears you have the same idea I do, Johnny. Let’s move on to fucking right away. We can catch up on old times later—much later!”

I hadn’t thought much about reminiscing with a girl whom I’d seldom spoken to in the past, so I was totally in favor of Jennifer’s sexy suggestion move quickly towards the act of coitus. I set her on her bare feet, albeit reluctantly, and off we went to her bedroom at the end of the hallway.

Jennifer had dressed minimally, presumably so she’d be naked in a hurry. She wore no shoes, nor socks. I was hardly a fashion expert, but her blue shorts did not seem to go well with her dark-yellow t-shirt featuring a seagull motif. On the other hand, I had dressed fairly well in an expensive sweater imported from Scotland and dark slacks. In contrast to my naked bedmate, I looked like I was perhaps heading to a job interview.

By the time I had fully disrobed, tiny Jennifer was sitting on the edge of her bed, patiently waiting for me to join her. She hadn’t worn a bra. She really didn’t need one as Jennifer had perhaps A-cup size breasts. I loved women’s boobs for many reasons; one was the wild variations they came in. Jennifer Matlock’s small pointy goodies with large areolas but tiny nipples were making me extremely horny. My rapidly rising erection was ample proof of that. I wish I had seen her take off her panties. She had shed them so quickly that I didn’t know what color they were until I saw them lying on the floor. (They were pink.)

“You are one sexy girl, Jennifer,” I told her sincerely. “Thanks so much for booking an appointment specifically with me. I’m flattered. I promise you won’t regret it for even a single moment.”

Jennifer excitedly gushed, “I hope that’s the case, Johnny!” she said. “Now come fill my pussy with your warm cum.”

I liked girls who spoke their mind and got right down to business! “Hell, yeah!” I said. What else could I say?

Jennifer propped herself up with three pillows. I snuggled up beside her. I intended to plant kisses on every inch of her sexy small body, but her tiny tits were a huge distraction. I focused on them almost immediately. I quickly wrapped my arms around her so I could have both her breasts literally in the palms of my hands. I knew Jennifer would be an excellent bedmate when she didn’t just sit by passively. She busied herself by stimulating my rising penis with her hands.

“That’s a nice, stiff cock you have, Johnny,” Jennifer said. “Just what I expected.”

“I aim to please,” I told her. “I can’t wait to put it to good use!” Still, before I began the inevitable sexual penetration of my longtime classmate, I wanted to suck on her beautiful titties for a few minutes. I did, culminating with my rubbing my dick against them for sheer pleasure.

With my dick so close to her mouth, Jennifer took the initiative to suck on it. “Scrumptious!” she declared. I had never heard that particular adjective used to describe my penis before, so I openly laughed at it.

“If you say so, my dear,” I said.

“I do say so, Johnny,” Jennifer replied. “I think it is sufficiently hard now. Please shove it inside my vagina and give me a big load of your semen.”

I had also intended to give Jennifer’s vagina some oral stimulation, but I understood her anxiousness for me to get down to fucking basics. I quickly mounted Jennifer and promptly slid my penis deep inside her hole. Since Jennifer was basically about a quarter of my size, her pussy was marvelously tight. It was comparable in snugness to the pussy of the 14-year-old I had screwed about a week earlier. That was fantastic. I hadn’t come inside that girl, whose name was Vicky. (She, instead, got a great facial from me.) However, I was going to follow orders and deposit my love juice squarely in Jennifer’s vagina. About a dozen long, slow thrusts later, I felt the semen move from my testicles into my shaft and then into Jennifer. “Holy smokes!” I said. It may have been the first time in my life I had uttered that mild interjection, but it was apt. I had something akin to an epiphany. I now believed that I had been put on the planet to impregnate this 18-year-old whom I’d ignored for years. My screwing certainly had a positive effect on the girl I was drilling. Jennifer was positively glowing.

“What a shame we didn’t do this back in our kindergarten days, Johnny!” Jennifer ludicrously stated.
“Uh, we were both five years old in kindergarten,” I reminded her. “I knew nothing about sex then. Furthermore, my dick couldn’t ejaculate, and you certainly weren’t built like you are now.”

“Trivial details!” she stated before laughing hysterically. I realized Jennifer was easily amused by her own jokes. If that was her biggest fault, I’d forgive her.

I was still semihard, so I figured I’d work on achieving my second ejaculation. Jennifer seemed to be happy to let me dictate the action from this point onward. I put her in a side-by-side sexual position that some people call “the spoons.” I always believed this was vastly underrated, especially if the female is well built. It allowed me to fondle Jennifer’s succulent little tits unobstructed while continuing to penetrate he pussy from behind. It was great! I told her she was a marvelous fuck no matter how my dick entered her vagina.

Jennifer let me ramble about her charms at length before declaring, “As long as you keep giving me your cum, I don’t care how it is delivered. Keep fucking me, Johnny. It’s a fun way to spend a Saturday afternoon.” I had actually forgotten what day of the week it was, never mind the time of day.

Almost on cue I came a second time. “You asked for my semen, you got it!” I said while panting. “This is quite a workout you’re giving me, girl!”

“All part of my plan to fuck you into blissful oblivion, Johnny” she confessed. “Okay, let’s see who runs out of energy first!”

We both slowed things town. We did more romancing than screwing for the next two hours. I refocused on Jennifer’s tits. She performed fellatio on me again. It had the desired effect. She was so good at giving blowjobs that I nearly came in her mouth. My tepid third ejaculation struck her chin and neck.

“Don’t waste you cum like that, Johnny!” she chided me. “You only have so much, you know. It needs to go in my pussy, not on my face.”
“That wasn’t much of a cum shot, but it does look good on your face,” I told her. “I can’t see it when it collects deep in your pussy.”

My testicles were clearly empty, so Jennifer and I just snuggled together for the next four hours. All the while we expressed our mutual admiration for the other’s sexual appeal.

“Am I worth $70?” I asked her jokingly.

“Double that at least, Johnny!” she told me. She then followed with a cute kiss on the head of my flaccid penis. She continued, “I left $100 on the kitchen table in anticipation of you being very good at your job. You probably didn’t notice it. I’ll gladly add another $40 to it before you leave. But you’re not leaving yet, are you?”

“No,” I said to my beautiful bedmate. “We still have some reminiscing to do before I go home.”

This puzzled Jennifer. “We hardly knew each other before we fucked so wonderfully tonight, Johnny. What can we possibly look fondly back at?”

I shrugged and said, “How about my three cum shots from earlier today. The first two were especially great. I think I could talk about them for hours.”