Paying for College The Crazy Way
by Jenelle Watson
I was quite uninterested in sex until I turned 18 years old. Oh, I talked about boys with my friends. We talked about boys a lot. But it was always in an abstract, dreamy way. Suddenly everything changed drastically, triggered by an ordinary medical exam.
Four days after my birthday, my mother scheduled medical exams for me and my twin brother, Zachary. We are paternal twins, so although we both have blond hair, otherwise we are quite different. He’s tall and athletic. I’m not. As expected I came through with flying colors, other than being told I should eat more. The only weirdness is that the doctor, for the first time in my life, performed a gynecological exam. During that part of the exam, I started feeling rather delicious tingles, although I really didn’t understand what that was about at the time.
My gorgeous brother, on the other hand, did have a problem. He was diagnosed with “phimosis,” a medical condition in which the foreskin is so tight that one can’t enjoy sex or in some cases even masturbation. He was aware that he had a bit of a problem, but always thought he’d grow out of it. The medical exam brought it back to his attention, front and center.
He was told circumcision, something he really didn’t want, would be required, unless he was willing to try some exercises first. He was scared about the idea of surgery, and so all for doing the exercises at the time, but within a few days, forgot about it, never having tried the exercises.
My mother reminded him, but still, he didn’t do the exercises. One day, she took matters into her own hands, quite literally. Right on the living room sofa, in front of me, she had him strip off his shorts and underwear, She got him erect, and started rhythmically pulling down his foreskin and holding it.
That very moment was a sexual awakening for me. I can’t quite explain why, but I became very interested in the male penis, and sexuality in general.
The reason my mother allowed me to be present in the room is that she wanted me to learn to do the exercises. My dear twin brother, I have to admit, is a terrible procrastinator. Since my dad is a useless drunk, and my mother works two jobs, she wouldn’t have time to do the exercises, and we knew my brother would forget, or fail to do them properly. So, it was left to me to make sure they were done every day. The reason he couldn’t do them himself, even if he was willing, is that they hurt a bit, and so he’d probably do it too lightly to have an effect.
So, every day at 4pm, we’d arrange to have him lay down on the sofa, and I’d fo the exercises for him. I found it remarkably exciting. So much so that I was peeing my panties a little bit. Or so I thought at the time. Soon, Zack, more knowledgeable of such things than me, pointed out that it wasn’t urine soaking my underwear. I was sexually excited. I guess I kind of knew that, because the fluid wasn’t yellowish urine, but something clear and a bit more viscous.
The first few times I ‘did’ my brother, he didn’t really like it. But soon, I didn’t have to instigate his erection with light touching of a feather. Soon, he arrived with a hardon all ready to go. He started looking forward to the exercises.
Within a week, he had his first ejaculation in my hands. In fact, it was his first ever waking ejaculation. He had partially remembered some waking wet dreams, but had never jerked off. His tight foreskin hurt him too much to want to try that. But during the exercises with me one day, he came! Although that first time freaked him out a bit, he soon started loving it.
Meanwhile, I was tingling in my vagina, my lower stomach, even my upper legs and breasts every time I did the exercises to Zack. It felt great, but somehow frustrating also. As if something more was required to satisfy me. I was so sexually unaware in those days that I really didn’t know what was going on.
Oh, I had seen naked people on the Internet, and I vaguely knew what masturbation was, but I had always thought such things were for other people, not me.
The first time Zack asked whether I wanted him to reciprocate, I thought he meant he was going to cook me a nice dinner, or maybe fix my bike – which would have been nice. But no, he spelled it out: He was willing to give me an orgasm.
I shockingly, but politely declined. But, it got me to thinking. A week or so later, I asked him whether the option was still open. It was! With the greatest loving and care, he gave me my first orgasm. That first time was rather weird, as it turns out, but still quite enjoyable.
I believe he must have studied up on the Internet, because what he did seemed quite expert. He had me remove all my clothes, get on the sofa, and started with a massage of my arms, legs and back. He returned to my upper thighs, and slowly worked his hands into my butt cheeks. I was feeling a fantastic tingle all over my lower body, and I started jittering, almost shivering uncontrollably. Then Zack started doing something. I believe he was lightly circling his finger just around my anus. Right then and there, I had my orgasm! He hadn’t even touched my vagina.
So, that’s where I left off in my first book, “Crazy Erotica – My Brother’s Handjob.”
In just a couple of weeks, Zack’s foreskin had stretched so we could see about 3/8-inch of a circle open up around his peehole. Before that, it was only about 1/4-inch.
We kept doing the exercises every day, and sometimes twice a day. He reciprocated quite often. Pretty soon, he was rubbing my clitoris and my G-spot like a pro.
The G-spot was a bit tricky because I was still a virgin. The doctor, during my recent exam, had confirmed that my hymen was mostly intact. But there was a small opening, and Zack was managing to gently get one finger through that hole without stretching it too much, and work up to my G-spot.
From time to time, we discussed whether we should go farther. Should we try sex? We thought we could do it safely enough. And we certainly wouldn’t be giving each other any STDs. But we decided that would be crossing the line. What sort of line it was, we didn’t really know, but we thought since we didn’t know, it would be best not to cross it. We did experiment a bit with kissing and licking each other, but we ended up preferring what we came to know as handjobs.
While the first part of our summer vacation was being filled with this wonderful new adventure between my brother and I, an idea was hatching in my brain. I wanted to become a psychologist since before I can remember. I think it started when I saw an old movie called Mumford, about a guy who posed as a psychologist. I don’t know now why that affected me so strongly, but it did.
But now, with this new experience with Zack, and the way I felt about my first and subsequent orgasms, I suddenly realized I would like to become a psychologist specializing in sex. Sex therapy. I figured I’d love doing that for a living.
Since this business with my brother, and my sexual awakening, I started studying everything I could find on the Internet. You know what? There is a ton of information about sex online! But I discovered that half of it is wrong, or just plain crazy. Still, it is all quite interesting. Yes, I knew I’d love to be a sex psychologist!
The problem was money. My father used to be a professor of herpetology, the study of reptiles, at the university. He was asked to leave, after trying to lecture drunk one too many times. That was probably when I was around eight years old. Since then, he has had to take menial jobs, and doesn’t manage to hold a job for more than a few weeks at a time. Whatever money he makes goes to alcohol. My mom, trying to hold things together, has two jobs, and still money is tight. So of course, there’s nothing to pay for my education. I mean, damn, if my dad hadn’t screwed up, I could have had free tuition, and could have gone to college right here in town. Now, I couldn’t even get a student loan, because who, with good credit, would co-sign?
I recently graduated from high school with good grades, and did qualify for a couple of minor scholarships, but I was still tens of thousands of dollars short of what I’d need.
What to do, right? You can bet I spent most of my waking hours trying to figure something out. Whatever waking hours were left, were spent reflecting on the very good time my brother and I were having. Those two trains of thought started to converge.
One night, in about the third week of summer vacation, I couldn’t sleep. I became completely excited, because I had a plan!
Around one in the morning, I grabbed my crappy old, barely functioning laptop, and placed an ad on Craigslist. My first attempt is laughable now, but it got me going in the right direction.
I figured I wasn’t the only woman who had not experienced an orgasm. I figured most women who hadn’t had no idea what they were missing. I found I was mostly right. And many of these women were much older than my 18 years. Imagine that, going through life for 40 or even 50 years, and not having the full joy of sex! Evidently, there’s a lot of women who have sex with their men, but are missing the best part. What I got wrong at first, and it makes me laugh now, is that I assumed it was the same with men. That a large number of grown men had also never had orgasms.
So what kind of ad did I place? I was offering to teach “How To Have An Orgasm” to men and women. I figured people would come over to our house, and I’d do for them approximately what Zack had done for me. I talked with him about it, and to him it seemed like a good idea as well.
Then I told my mom. Now, we’re a very open family. Everyone has seen each other nude. We can talk about everything, although we just hadn’t happened to talk much about sex. I was rather certain she’d embrace the idea. It would bring us a lot of money. I mean, a typical piano teacher gets $30 for a half-hour lesson. That’s $60 per hour. Zack and I could bring that in all day long, if we had enough clients. That’s $120 per hour between the two of us.
Well, let’s just say she didn’t embrace the idea at all! I deleted the ad from Craigslist.
But here’s the funny thing. After trying to discuss it with her in a way that she could get behind the business idea, and after she started bringing up all the negatives such as our safety and ‘what would the neighbors think?’ she started actually coming around to liking the idea. Finally, about four weeks into the summer vacation, she said, “OK.”
But the idea had been greatly compromised to meet her requirements. Zack and I had to both be present in the house any time either of us had a client. We had to make sure to call it ‘education’ and not any sort of ‘massage,’ or ‘sex,’ since those kinds of things are illegal. We weren’t sure, but we thought it might be illegal anyway. Surprisingly my mom declared that it was morally OK, maybe even a good thing, and “morality trumps legality” – her words.
So, the ad went back up.
Guess what happened? Nothing! No one responded. Then, someone flagged the ad, and it disappeared. I must have done something wrong.
Zack and I talked about it, and I think the flaws were that we didn’t mention who we were. The readers probably thought we were crochety old men or something. We also put it in the wrong place. It seems the “Lessons” section of Craigslist isn’t right. Now the “Casual Encounters” section, That’s a whole different story. It took a couple of days to figure this all out. I was freaking out as I watched our summer melt away, and I hadn’t made a penny toward my education. I had already been accepted to a university 2,000 miles away, but what good was that if I couldn’t pay for it? I couldn’t even afford the bus fare to get there. I was kind of jealous of Zack, because he had a full-ride tennis scholarship to the university right here in town.
Then, we got the ad right, including head and shoulders pictures of Zack and I. We thought about not showing our faces, or disguising ourselves, so our friends, neighbors and family wouldn’t find out what we were doing, but then we realized that if we felt we had something to hide, we weren’t approaching it the right way. Teaching something that gives people a sense of freedom, joy, self-esteem, and good health is a good thing, and we, ourselves, had to make sure to always see it that way.
People started emailing, just a trickle at first. A couple were obviously creeps, or way off-base. Like, “I’d be happy to lick your pussy.” Things like that didn’t even get a response from us.
I should say “men” were emailing. Nothing came in from any women. I was kind of alright with that, at least for now. I was starting to understand that not having orgasms was mostly a female thing. Pretty much all men knew how to have orgasms from a young age. I had been ‘doing’ Zack, so I shouldn’t have any trouble doing something similar for other men. Yes, I did realize they already knew about orgasms, and I was offering to teach what they already knew, but hey, they were willing to pay, right?
Zack, he wasn’t so sure he wanted to work with men, but to his credit, he didn’t discount the idea entirely.
From the few applicants who seemed promising, Zack and I selected our first one. According to his correspondence, he was 45 years old, married, a bit overweight, and enjoyed ‘new experiences.’ He didn’t say whether he had ever had an orgasm, but Zack assured me he must have.
So we set up a time and invited the man over. To say I was nervous would be the understatement of the year. Ten minutes before ‘show time’ I went to the bathroom and almost threw up. It was just like the stage fright I had in the school play when I was in middle school.
It would have been nice if Zack had been willing to help with this first client, but he shied away, telling me he’d be elsewhere in the house, and listening in case any help was needed. As to Zack providing security, I wasn’t worried. Did I mention, he is a big, strapping, and yes, handsome guy? He also took karate lessons for a couple of years.
Right on the dot, John, our first client, arrived. The session started out quite awkward. Even though Zack and I planned everything out in advance, this thing went off into the weeds almost immediately.
As soon as John walked in the door, he wanted to kiss me. Not like a family friend or something. He wanted to really wrap around me and kiss me on the mouth like a lover, or maybe like a prostitute. I backed off immediately, glad Zack was in the house, and told John it wasn’t going to be like that. To John’s credit, he was mild mannered, and backed off apologetically.
I then started on the preplanned spiel, knowing that John most likely knew all about orgasms already. I explained what orgasms and ejaculations were and the reasons they are good things. That having regular orgasms eliminates sexual tension, horniness, so that one doesn’t bother the wrong people at the wrong times, tell off-color jokes in inappropriate places, and so on. That regular ejaculations are good for health, protecting the prostate, and lowering blood pressure. And that regular orgasms help with body awareness, mental clarity, and all that.
John quietly took it all in, pretending it was all news to him.
Now, it was time to get down to the real business at hand, just as Zack and I planned. We had John remove his clothes, slowly and one at a time, until there was nothing left.
For a fat guy, he wasn’t really that bad to look at. Mostly, I noticed his penis. It was erect from even before he removed his underwear. I could see the shape of it through the white cloth. It was a nice penis. Fatter, and I think just a bit longer than Zack’s. This was only the second real, live penis I had ever seen, and I immediately liked it. But I couldn’t touch it.
That’s a big thing that Zack and I figured out. We thought the act of actually touching someone would get us in trouble. Now, if I had a massage license, or was a doctor, or if I was a sex therapist, that would change everything, But, I wasn’t. Not yet.
So what we decided to do instead is coach people through the orgasmic process. And that’s exactly what I did. I ‘taught’ John how to masturbate himself. He was hesitant at first, but after only a few minutes, he got more and more into it. Within probably five minutes, he ejaculated quite a bit of stuff onto his stomach. I handed him some paper towels so he could wipe himself off. Then, he immediately put all his clothes back on. The whole damn thing happened in less than ten minutes. John thanked me profusely, explaining that having an 18-year-old girl watching him, was in his mind, just fantastic! And then, he handed me not the $30 I had advertised, but a crisp $50 bill. I started to give him $20 change, but he said that was a tip. He then thanked me again, and left. Just like that!
A minute later, Zack came in, and was all like, “So what happened? How was it? Tell me exact details!” I realized he had totally wished he had been there to see it.
The next day, we had another client at 10am, and scheduled another at noon. The first guy was surprisingly similar to John. He, too, was heavyset, but a bit older, and almost totally bald. His penis was smaller, and it took him a while to get it hard. Still, the whole thing was over in 20 minutes, with this guy, too, having a nice ejaculation. Like John, he went along with the ‘lesson,’ even though it was pretty obvious he knew all about orgasms. He also mentioned something that made me think about things a bit: He said the best part was having me watch him. Hmmm.
The guy at noon was something that we later found out is somewhat rare in this business, a man in his early twenties. He was tall, slim, and looked like he could have been one of Zack’s basketball friends. Zack and I both greeted him at the door, and I offered to take the guy to the sofa and started in on the ‘spiel.’ As Zack walked out of the living room, the guy said, “Hey, you’re welcome to stay, too.”
Zack’s eyes sparkled. This was an opportunity that he had been secretly but strongly hoping for.
I have since developed a theory that everyone is somewhere on the bisexual scale. Some are pretty nearly 100 percent straight, others nearly 100 percent gay, but most are closer to the middle than you may think. So, it shouldn’t be a surprise that my dear, sexy, seemingly straight brother would enjoy seeing a man jerk off.
So, I coached this guy to his orgasm while Zack and I watched, and collected our $30. This was turning out to be a fun business!
The next day we had three men scheduled. The first and second went perfectly. It seems we were developing a formula that these guys liked. No one was disappointed, because we did spell out the procedure in the Craigslist ad. They pretty much knew that they would be ‘instructed in how to have an orgasm’ and would actually have one. We guaranteed it, with a money back warranty. But, we left it to them to wonder whether we would be naked, whether we would participate in any way, and so on. We didn’t do any of that stuff.
I kind of wanted to participate more, but didn’t even dare think of it at the time.
The third guy was a bad surprise. I mean, really bad. He was good-looking and fit, being perhaps 35 years old. His complexion was very black, like first-generation African. His hair was short. This guy’s name was Luke. He seemed friendly, but kind of reserved. I sensed something was wrong, and so did Zack. My brother didn’t say any words, but I could tell he was feeling something was off, too.
We asked Luke whether he wanted just me as his instructor, or both of us. He wanted both. Zack presented the spiel. We then instructed Luke to start taking off his clothes, but he didn’t want to. We reminded him that it would be necessary if he was going to have an orgasm. Luke wanted an exact description of what was going to happen, so we told him. We were quite specific, saying how he would be instructed to take off his clothing bit by bit, then would be told how to touch himself, bring himself to an erect state, and finally how to have an orgasm and ejaculate. He asked if we were going to touch him in any way.
I didn’t know what to make of that. Was he not wanting to be touched? Or, was he wanting to be touched? Either way, Zack and I were resolute that we were not going to touch any client. I was becoming quite concerned. Not for our safety, but that something was off with this guy Luke. Something was going wrong. Hesitantly, Zack explained that we never touch anyone.
Luke broke out in a great big smile. “You passed the test!”
I was like, ‘What the fuck?’
Then, Luke pulled something from a back pocket. I thought at first it was a cellphone in a flip case. But no, it was a police badge. He explained that he was a detective, and among his duties was to bust any sort of illicit prostitution or happy ending massage practice. He said that he didn’t like that part of his job, but it was the law, and he did have to uphold it.
Even though he said we passed the test, we were still quite concerned at that point. It took me a good couple of minutes to get my heart back out of my throat, and looking at Zack, I could see he was going through the same thing.
Luke went on to tell us that if we kept going on the same way, we’d be totally legal, and he, and ‘his men’ as he called them, would not only leave us alone, they’d protect us to any extent they could. He then wanted a discount.
At first, I didn’t understand. He said his men might like some instruction, and could he work out some sort of group discount?
Whew, talk about sigh of relief! He wanted half off for anyone carrying a police badge. I would have been fine with that, but Zack offered $5 off. We settled on $10 off.
I can’t tell you how happy we felt to know we were on the right side of the law. We had been quite concerned about that.
Days turned into weeks, and our business grew. Luke had been a major stroke of luck. Some of his buddies on the force started emailing right away, and the next thing you know, we were booked solid for eight hours a day! Not one of those guys got weird on us. Some of our non-police clients would act up a bit, but just a bit. We never had any sort of violence or anything we felt we couldn’t control.
Well a couple of guys pulled something unexpected. These guys didn’t want me, they wanted Zack. At first, he was a bit weirded out by it, but pretty soon, he seemed to have gone through some sort of transition, and liked coaching ‘his men.’ Those few homosexual guys had more friends, some on the force, and some not. Pretty soon, Zeke was doing guys in his bedroom, and at the same time, I was doing other guys on the sofa. Not long after that, we bought two massage tables, and did everyone in the living room, often two men, strangers to each other, at a time. I silently got a kick out of seeing many of the guys trying to surreptitiously watch each other’s ‘lessons.’
Luke came back a couple of times, and partook of our service just like any other client. He seemed to prefer me over Zack, but received coaching from both of us.
Working this way all day had a strange effect on me and Zack. At the end of the day, when the last client left, and an hour or so before either of our parents came home, Zack and I would throw off our clothing with rapid abandon, and we’d do his exercises, and he’d masturbate me. We learned to take each other to the brink several times, before having orgasms, and that only heightened the pleasure. Oh, I loved handling his penis! And, of course I have to say, I loved getting his treatments also.
My mom and dad monitored our new business with great concern. But, since both were out most of the day, and since we kept the house pretty much in order, they started to settle down. I’m surprised they didn’t say anything about the sessions Zack and I gave each other, but then, they didn’t really know about them, and I was authorized to administer Zack’s exercises, after all. In retrospect, I can only imagine what was going through my mother’s head regarding me ‘doing’ Zack.
It had to happen eventually: Friends, family and neighbors starting finding out what we were up to. We had known it might happen early on, and decided the best approach would be to face it honestly and head-on. When someone would mention knowing about our ‘sex education’ business, we’d just say “Yes, it’s going nicely.”
The first person to discover the business was my grandfather. When he confronted me about it, I wished Zack was there. But he wasn’t, and I felt like I was back in grade school, had done something bad, and was being set to the principal’s office. But guess what? My grandfather congratulated me! He said it was marvelous that I was willing to ‘try something so outside of the box.’
And that’s the way it went with everyone. No one got all high-horse on us or anything else. For some reason, everyone was almost overly supportive. Maybe our society is ready for change, and everyone knows it.
One day, we had a female client. We asked whether she wanted me, Zack, or both of us as instructors. Normally, we would have offered only Zack or me, not both, because we’d make half as much money, but for this, it would be worth it. It hadn’t yet occurred to us that we could charge twice as much for both, and plenty of people would pay it. She opted for ‘both’.
It turned out to be rather uneventful. We did exactly what we did with the guys. We instructed her to slowly remove all her clothes in front of us. She was about as shy as our shyest male clients.
Now, some guys will drop their clothes easily. Others are reluctant, and have to be coaxed to disrobe. Some guys will spring immediate erections. Some take forever to get hard. We have had sessions that run long. We have even had to offer refunds a couple of times when the guys simply couldn’t cum at all. Most of those guys refused the refund, and we offered them ‘make-up’ sessions, where they could come back for free and we’d try again. And good news: Most of them were able to orgasm the second time around.
So this lady, Carol, reluctantly disrobed in front of both Zack and I, and I started coaching her. I had long since lost the wet, tingling between the legs effect with every guy that came in, but to my surprise, I got it again when I saw Carol totally naked. She was red-haird, had big pendulous but smooth breasts, with freckles on her face, arms, and upper chest, but none on her milky white, delicious tits. Her nipples were particularly small, totally light pink, almost blending into her skin color, and pointy, which I found intriguing.
The thing that really got me was that she was totally shaved on her vagina. Some of our guys shaved their lower regions also, but this was different. I was immediately attracted to her more complete nakedness, and I could tell Zack was too.
Well, we instructed her to her orgasm, and although it took a while, it came on very strong. I don’t know, but I think that may, possibly have been our first legitimate lesson, in which we actually instructed someone to orgasm for the first time in their lives. I felt it would have been unprofessional to ask her afterward whether that was her first.
We gave her a few minutes to compose herself, after which in a very business-like manner, she put on her clothes, paid us, and thanked us.
Many of our clients were repeats. They’d come every week or two for ongoing instruction. Not Carol. That was, unfortunately, her first and last time, so we never did find out whether that was her first-ever orgasm. Maybe she, just like the guys, played along with us about the ‘lesson.’ Maybe not.
At the end of the second day after Carol’s appointment, Zack and I threw off our clothes in our usual hurry to have our own orgasms. I had to laugh. Zack had shaved off all his crotch hair. Oh, I wasn’t laughing at his baby-smooth naked crotch, but at the fact that I had done the same thing. When he saw my naked pussy, he went nuts with zeal, rubbing me to a fantastic series of orgasms while he stood next to the massage table with a fantastic hardon, occassionally dripping precum on the floor.
Our parents were very good about staying out of the house until 7pm, after we had finished with our last client, and we did a little something for each other. I think Zack and I were already making more money than Mom.
One evening around 7pm, my dad, who was surprisingly sober for once, came home and started asking about exactly what we did. I think Zack and I got a bit red in the face, because it… Well, it just felt weird explaining it to Dad. Then Zack, hero that he can be, said, “Dad, you’ll just have to experience it for yourself.”
Holy fucking cow! Did he just say that?
Without missing a beat, my father said, “Oh, I’d like that.”
I couldn’t believe my ears, and didn’t know how to proceed.
Fortunately, Zack knew what to do. He handled Dad, just as if he was another client. Slowly, in the procedure we had come to know so well, he instructed Dad to take off his clothes one by one. There was my dad, my own father, in his underpants, and I could see that he, like half of our clients, was already erect. Next thing I knew, the underpants came off, and here was Dad, naked as the day he was born, standing in front of his two children with a full-blown erection.
And, it didn’t feel as weird as you might think, other than I felt that all-too familiar tingling in my vagina. I rather liked my father’s body. He was thin, and still looked like the athletic field-tripping reptile-hunting professor he used to be. His penis was surprisingly like Zack’s – kind of thin but long. But Dad was circumcised.
By now, I had seen a whole lot of penises, and was surprised by the variety. Of course you have your circumcised and uncircumcised ones, your white and black ones, but there is much more to it than that. Some guys have a half-inch long peehole slit. Some guys have a little tiny peehole. A few seem mismatched, color-wise. There are some guys who are not quite white, but lightly complected, but they have surprisingly dark genitals – penis and scrotum. It’s almost as if they were wearing someone else’s parts. Scrotums vary quite a bit also, but I found out it’s more about the current situation than the guy. Their scrotums tighten up in some circumstances, such as when they are feeling cold, or when the scrotum is touched or tickled, and get loose when warm and left alone. Some guys have a large penis, and some small. The actual measurement isn’t all that different, but to me at least, a five-inch penis looks much different than a seven-incher. You may be surprised by this, but I like the smaller ones better. I also like the guys who start off soft, and require quite a bit of time to become erect, even though it can get a bit boring at times. I think I like the feeling of success when they do get hard and finally ejaculate.
Now, I was getting horny seeing my dear old dad with an erection! We were a nudist family to some degree. I mean, we had often passed each other on the way to the bathroom, or passed open bedroom doorways and seen each other nude. But never with an erection!
And, cool as a cucumber, Zack instructed Dad on how to have an orgasm, as if he didn’t know how. Of course we knew he knew how, or we wouldn’t have been there experiencing that! But, like almost all our clients, he pretended we were teaching him something new. Pretty soon, my own father was beating off in front of us, his son and daughter. He was breathing hard, and just kind of staring into space. It didn’t take him long to cum. Somehow I was expecting a huge spurt of semen, but it was only the same as an average client.
The first thing he said afterward was, “Zack, that was great instruction. I do believe you and your sister are offering an excellent service.”
The second thing he said was a question: “Zack, how are those exercises of yours coming along?”
That sounded like an unmistakable invitation to me. I was wondering whether Zack understood it the same way.
“Hey Dad, look.” And then he pulled down his pants.
“Well, I can’t really show you unless it’s hard.”
“Go ahead and make it hard, son.”
“Well, Jenny usually helps with that.”
I knew exactly what was expected of me at that point, and didn’t mind a bit! Somehow, I was very excited to put on this show for Dad. I threw a clean sheet onto one of the massage tables, had Zack lay down, and went to work. Ever so lightly, I started waving my right index finger over Zack’s penis, as I explained the whole procedure to Dad. Zack hardened up right away. I then pulled the foreskin gently back, revealing almost a half-inch circle of glans through the opening of the foreskin. Zack explained that it used to be impossible to expose even half that much, and that now he had high hopes he could become completely normal. And, just as he said it, he ejaculated all over my hands and stomach, causing us all to laugh.
A minute passed as Zack cleaned up and we exchanged some small talk. Well, not exactly small talk. Dad said that he had the same problem as Zach, but had been circumcised when he was 16 years old. We asked for details. He said that Zack had made the right decision. First, the circumcision hurt like the devil for several days after the surgery. He’d wake up with partial erections that were particularly painful pulling on the stitches. It turns out that babies can be circumcised without stitches, but adults need them. Then, for at least a year, the glans, which for all his life until then had been encased in the moist, protective skin, would rub against his underwear and drive him crazy with a sort of tickling feeling so intense it was almost painful.
Then Dad cleared his throat, and at the exact same time, he and Zack said, “What about you Jenny?”
I said something non-committal, like “Oh, don’t worry about me,” thereby destroying the opportunity. I immediately regretted that response. Unfortunately, neither Dad nor Zack pressed me. Damn! That night, I masturbated myself to several orgasms imagining what might have happened if I had responded differently. I would have liked Zack to start lightly, and then put his finger deep into my vagina and rub my G-spot to a crashing orgasm. It would have been just fine if he destroyed what was left of my hymen in the process. Or better yet, what if I could have Dad do that? Oh, my God!
The next day, after Zack’s exercises, he offered to ‘do’ me, and I gladly accepted, imagining that Dad was still there, and had yet another crashing orgasm.
Summer was drawing to a close, and after helping Mom with the mortgage, I had only just a bit more than half of the money for the first payment I’d need to start college. Oh, well, I certainly tried!. Surely next year I could start becoming a psychologist. Then Zack did the sweetest thing: He gave me all the money he had saved up! He said it was a loan, not a gift, but it was still the greatest gift in the world!