Copyright 2017, Jeremy J. Watson
I’m normal in every way, except one. If you saw me on the street, you wouldn’t remember me. I’m average height at 5′ 10,” wear my brown hear medium length, and have a trimmed beard. I’m not thin, but I’m not fat. But the one thing that’s different about me is that I’ve always been a rebel.
My embarrassing father taught me to be rebellious before he drank himself to death. That’s the one thing I got from him, his repeated admonishments, “Think for yourself, boy!”
He was one of those happy drunks. Never violent, just making messes wherever he went. Dad couldn’t keep a job, especially after he lost his driver’s license. He was a loving father, but just sloppy drunk too often. I lost him when I was sixteen. It was a shame, and it messed up my life and my mother’s life. We were already in poverty, and then, we had to come up with $800 for his cremation. All Mom and I had was a junky house, and even that we were on the verge of losing, always being late with the mortgage month after month.
As the end of high school approached, I was hopelessly behind sexually. I hadn’t had any sort of sex with anyone. At the time, I was trying to get laid by girls thinking that was the ‘right’ thing to do.
From as early as I can remember, I’d swivel my head whan a good-looking guy rode by on a bike or when I saw underwear ads, When I’d see a girl in a bikini or something, I usually forgot to even look until one of my buddies might say something like, “Did you see the knockers on her?” I didn’t know what to make of the situation, but tried to stay focused on women. My dilemma concerned me greatly, and I spent hours trying to understand how I fit into the world.
With my friends, I’d play along. I’d share in all the off-color jokes about women, and pretend that I was on the verge of dating one girl or another. Truth is, I didn’t really know how to talk to women, let alone anything more. One by one, my buddies fell away, as they each in turn hooked up with a girlfriend. I was secretly jealous, but what could I do?
Finally, Michelle came along. She was second-generation Korean, short, slim, small-breasted, with long, straight hair, and cute as a button. I actually found her attractive. And she seemed to like my quirky, rebellious sense of humor. Maybe she liked my shyness too, because she was the opposite, always saying whatever was on her mind, no matter how outrageous. Among the 12th grade girls, she was a sort of leader. She and I started having conversations, and it was easy. It wasn’t like talking to other girls. I finally figured out why: She was a rebel, too.
We got closer, and started kissing. It was OK. Not super-great, but definitely OK. The day came when she started wanting to have sex with me. I had been resisting. I don’t know why, Maybe, it was because deep down, I knew I was gay. I wasn’t really attracted to her the way I thought I was supposed to be.
I could only put her off for so long. She became insistent. She’d do things like pinch my crotch while kissing, try to pull down my fly, or get us into games of strip poker.
One day, after the usual gym class shower, in which I tried hard not to get an erection, successfully I might add, she and I got together at my house while my mom was at work. I was still horny from seeing a couple of naked guys in the showers.
She had a deck of cards, and wanted to play strip blackjack. I went along. It seemed to me, that although the thought was scary, getting naked with her might actually be enjoyable.
So we played, and lost clothes at a nearly equal rate. Finally, she lost her bra, and I saw my first-ever set of live girl tits. Oh, I had seen stuff on the Internet, but never really paid attention. I kind of liked what I saw in Michelle. She was like a little boy, in a way with her small, nearly flat boobs, and perhaps that enhanced my appreciation. I was surprisingly attracted to her small, pointed, dark nipples, and imagined myself sucking them.
Then, I lost a hand, and my last covering, my underpants, were no longer going to protect me. She insisted that I remove them. So what could I do? I did. My penis wasn’t erect, for which I was grateful. Somehow, having an erection in front of her seemed like it would be embarrassing.
Michelle frowned. “Why aren’t you hard? Don’t you like me? Don’t you like what you see?”
I didn’t know how to answer that, and so I hesitated for a moment. Her lower lip started to quiver.
OK, it was now or never. I had been kind of admitting it to myself for the last year or so, but to avoid hurting her feelings, I had to say it, and I hoped that my good friend, Michelle, of all people, would be understanding.
“Michelle, I have a… well, a secret. I might be attracted more to guys.”
“Hot fucking damn!” she practically yelled. “I knew it.”
Within seconds her frown turned to a smile.
“Ben, it’s OK. In fact, I think it’s great!”
Wow, that was easier than I thought.
“But Ben, let’s continue the game.”
“Really?”
“Yes, fuck yes.”
I was feeling all weird inside, but she seemed to want to continue our strip card game, so what the hell, right? I was already naked, so it couldn’t get any worse. In fact, it wasn’t that bad. It felt somehow freeing to be naked with a good friend. I could swear I felt a breeze on my ass and balls, even though we were in my bedroom, and I liked it.
She lost the next hand, and she took off her little underpants right away. Of course, I noticed the dark curly hair around her vagina, Now, you’d have thought I’d get excited, or at least a little twinge, but nothing. Not even like the bit of excitement I got in the school shower with the guys. Well, maybe I had a bit of curiosity, but that’s all.
She then said, “Let’s keep playing.”
“How? I mean, what’s more to lose?”
“Well, if you win the next hand, I have to do what you tell me. If I win, you do what I say.”
“Fuck that!”
“Now Ben, I won’t ask you to do anything you don’t want, I promise. And, I’ll bet you can’t think of anything to ask me that I wouldn’t want to do for you.”
‘Wow,’ I was thinking. ‘Now, that’s interesting.’
I won the next hand, and I wanted to see a vagina up close. I didn’t really like the looks of pussies, from what I’d seen on the internet. They seemed like wounds into a girl’s body or something. Still, I was curious. So, I asked her to let me look closely.
I was expecting her to put up a fuss, but no, still sitting, she scooted to the edge of the bed and spread her legs really wide.
I approached tentatively, and after a moment, I placed my fingers in that hair, and kind of separated it so I could see her slit. I just looked. She told me to spread it open. I started to, but she said “Ouch.”
I guess I had pulled her hair. More carefully, I did spread it open. It smelled kind of fishy, but not terrible. I found the little thing called the clitoris, and carefully rubbed my fingertip against it. She leaned back and said “Mmmmm!”
I had read that girls like this, so I kept doing it for a while. She leaned back further, and scooted so she was laying on the bed. I noticed that her pussy was getting quite wet. She was starting to arch her back, but suddenly stopped me. “Not yet,” she said.
I guessed she was getting close to orgasm.
While this was happening, and without me noticing, I was starting to spring an erection. I was feeling… well, many things. I was delighted. Maybe it meant I wasn’t gay, which was still a big concern for me. I was really confused back then. On the other hand having a boner was also terribly embarrassing. No way Michelle didn’t see it.
But she was delighted! She reached out, and gingerly touched it.
Bang! Electric shock! I had never experienced anything like that in my life. Oh, I had masturbated a million times by then, but that was the first ever touch by someone else. Not even a doctor had touched my dick. My parents didn’t even have money for medical insurance, didn’t understand paperwork, and so I had never been to a doctor.
I asked her to touch it again, and she did, and I got another, somewhat smaller shock effect. She kept her hand on my dick, and started slightly stroking it up and down. I got super-hard, as erect as I had ever been. I have to tell you that even though it was a girl touching me, it felt amazing!
She was pretty smart, and knew if she kept it up, I’d cum right away. Instead, she stopped.
She leaned over to the floor and started digging around in her backpack, eventually pulling out a small packet. I knew what it was, and what she wanted. I figured, ‘Why not?’
I asked her to put it on me, but she declined, saying I’d probably ejaculate if she did. In retrospect, she was probably right.
So, opening a rubber packed for the first time in my life, I took it out, and figured out how to unroll it onto my cock. She was so right, I almost came from my own attention to my dick at that point.
“If you’re gay, you’ll like it this way. Just pretend I’m a guy.” she said, and with that, she got back on the bed on her hands and knees with her ass up and open.
I got behind her, and actually enjoyed the view. Especially her small, puckered, somewhat brownish asshole was perfect. If I could only have one memory in my life, I was thinking, I wanted it to be that image! Oddly, I wanted to press my dick into that anus of hers, but I knew that wasn’t quite right. Girls like to be fucked in their vaginas.
Being a good-natured guy, I did that for her. She was terribly wet, and so we didn’t need any lubrication. I wouldn’t have known if we had needed lube at that point. As I said, I was completely inexperienced with girls, and guys, too, of course.
Kneeling behind her, I very slowly, and awkwardly, pressed my penis into her vagina. Even though I didn’t care for the look of that part of her, I noticed how beautiful and warm it felt, even through the rubber. Then I felt an involuntary squeeze from her pussy. I’m sure you can guess what happened. I came right away.
A minute later, my penis wilted and sort of fell out of her vagina.
She expressed a mild disappointment.
Now this is horrible: She asked if I could kiss her vagina or rub her clit some to give her an orgasm. I said “No,” and ran into the bathroom, still wearing the rubber.
I know that was very bad form, and must have hurt her feelings, but I was alarmingly conflicted. Five minutes later, without the rubber, I reappeared, and apologized. I still couldn’t bring myself to touch, let alone kiss her vagina, and she seemed to be OK with that.
So, I fucked a girl, and it wasn’t the worst thing in the world. I kind of liked it, even though it freaked me out.
But that was the only time. Michelle and I talked about it, and she decided she wanted what she called a “true, blue guy.” I was OK with it too, because I just wasn’t, well, I don’t really know. I just didn’t want any more sex with her. What I came to realize later, is I really didn’t want sex with any girls.
It’s like you really want chocolate ice cream. Someone gives you peanut ice cream. Yes, you’ll eat it, and it’s OK, but it’s not quite right.
We’re still friends to this day. I mean, if we see each other in the grocery store or something, we are happy to see each other and catch up a bit. But that’s all.
High school ended, and I graduated with fairly good grades. With my dad being gone, and absolutely no money, I knew I had to do something. I thought becoming a nurse might be a good idea. Since I’m kind of inept at dealing with people, what could be a better experience for me than to have to deal with people on such an intimate level as a nurse must do?
But, it wasn’t going to happen. I spent quite a bit of time with the guidance counselor trying to figure out how to get into a nursing school. There was just no way I could raise the money, and no one would co-sign for a student loan who had good enough credit. My mom was working full time, but her credit was shot to hell.
So I got to thinking about what might be similar to nursing that didn’t require a degree. It doesn’t take a particularly intelligent person to come up with massage as a possible alternative. You and I both know that there are various ways to do massage. I was talking about legitimate massage. But I didn’t even have money for massage school. Now, it’s technically illegal to do massages without a license, but I was desperate. I could do massages and make $60 for an hour, and maybe get my own place, help my mom out of debt and so on, or bag groceries for $10 per hour, and maybe barely manage to cover the cost of food. Rebel thinking, right?
In this case, I wasn’t enough of a rebel. I chose bagging. As it turns out, the world is full of 18-year-olds like myself who want to do that sort of minimum wage job. After spending a week applying everywhere, I discovered there were no openings for me.
My mom was supporting me, and she was sinking in a hole fast. I had to do something. So, I went to the library, and took out three books on massage.
I explained my plan to my mother, and she nixed it, saying she didn’t raise her one and only child to do something illegal. Completely frustrated, I asked her what my options were. She didn’t have an answer. The next day, when she came home from work, she said, “OK, but be careful. Furthermore, as soon as you can, go to massage school, and get properly licensed.” In her optimistic way, she was already seeing me being successfull in the massage business, which I suppose was contagious.
The books I borrowed were sort of exciting. Especially one, where a good-looking man was being the subject in the photos. They were old-style black and white pictures, and the guy was fully naked. In one shot, he was laying on his stomach, and his buttocks were being worked on. They were stretched just a bit open, and you could barely see his hairy asshole and the bottom of his scrotum.
As soon as I saw that, I took a break and jerked off. I was thinking, ‘I wouldn’t mind working on naked people all the time!’ Unfortunately, the other two books indicated that a massage practitioner usually drapes clients, meaning they are modestly covered with cloth most of the time.
I studied, and learned, also looking up ‘massage’ on the Internet, doing my best to focus on the legitimate stuff, not all the crazy sexuality.
A few days later, I felt I had picked up all the information I could. Now it was time to get a little practice.
I called a high school acquaintance, and offered him a free massage, explaining my plan. He was like, “No, too weird.”
I was embarrassed, and almost didn’t call another guy. But remembering my mom’s plight, I got up the balls and called another guy.
Same thing, I explained how I was learning to become a massage practitioner, and needed to practice. I was bracing for the inevitable, but he said, “OK.”
We arranged for him to come over at 4pm. I also called my mom at work and asked her not to come home until 5:30. That was fine with her because she usually didn’t get home until around 6 anyway.
So four o’clock came along and James didn’t show up. I was crushed. But about eight minutes later, the doorbell rang. Suddenly, instead of crushed, I was nervous. What the fuck was I thinking? Me, a massage practitioner? Oh well, it was arranged, I had to go through with it.
So I opened the door and let James in. I should probably mention that he wasn’t a close friend. He and I had played chess a half-dozen times, that’s about it. The thing is, I had to go with acquaintances rather than friends, because I was kind of embarrassed about letting my friends know I was planning this whole massage thing.
James was not a close friend because he was out of my league. He was one of the really cool guys in the school. Fortunately for me, he liked chess, and I’m particularly good at that game.
James was really tall, probably around 6’4,” short-haired and thin. He was also very black, like straight African ancestry. He was also a great basketball player who had won a scholarship to a university in Ohio. He was a great first ‘victim’ because if the massage didn’t go well, he be gone away to college in a couple of months and hopefully wouldn’t tell anyone in the meantime. He came in kind of reluctantly.
After a bit of small talk, he told me he had been having some trouble with his left shoulder. He thought I might be able to help with that.
Blustering entirely, I said, “Of course.”
I showed him to the bathroom, told him to remove his clothes, and come out wearing a towel. A few minutes later he reappeared.
I drew in my breath, hoping he didn’t hear me. The guy was gorgeous. I should have maintained a professional attitude, but those long black legs of his caused an immediate horny reaction in my stomach and elsewhere.
Trying to seem professional, as if I had done this a million times before, I directed him onto the torn, second-hand massage table I had. He didn’t know how bad it was, because it was covered with a sheet.
James laid down, and I went to work. I knew enough to warm my hands and use massage oil right from the start. I kind of randomly rubbed his delicious, skinny, shiny back. Then, I decided to do what I could for his shoulder. I just kind of pinched here and there. As I was doing that, he’d mutter little things like, “Um hum,” “Oo,” “Yes,” or “Mmm.” Once, when I hit a sensitive spot he quietly said “Ouch.”
I practically jumped when he said that. I didn’t want to hurt the guy. I wanted to do it right, to give him a really good massage. All the while, I realized I didn’t really know anything about what I was doing.
After what seemed like a long enough time, I worked down his back, and down his upper arms to his hands. I was worried that he’d think it was ‘gay’ to massage his hands, but he seemed to like it.
Then I went to his upper legs, working my way to his feet. Something I didn’t realize about giving massages is that it is a lot of work. My wrists and thumbs were starting to cramp up. When I couldn’t take it any more, I figured a brief break would help, so I asked him to roll over.
He said, “Wait, aren’t you going to do my butt?”
I was like, “Oh, right.” and I tried to sort of reach under the towel and massage his glutes a bit. He knew I was struggling with trying to reach under the towel, and keep it on him at the same time, because he just reached back with one hand, grabbed the towel, and threw it on the floor.
What a magnificent ass! Smooth as an eight-ball, and nearly as black. I might have been starting to have an erection at that point, but that was unprofessional, so I tried willing it away. Not knowing exactly what to do, I started massaging his ass with both hands. I guess I got it about right because he was saying, “Mmmm, excellent!”
At one point, with one hand on each ass cheek, I made a movement which spread his ass cheeks apart, and I saw his asshole. It was mostly hairless, and if you can imagine, it was even darker than the rest of him. I was sorely tempted to touch it, but I knew better.
In retrospect, I’ll bet if I had rubbed my finger lightly around it, then slowly stuck it in, he would have loved it. But I still had a lot to learn.
After what seemed like the appropriate amount of time, I had him flip over and placed the towel back over his crotch area, but not before noticing he was sporting a nice erection. And his very black, uncircumcised dick was huge, like eight inches long. I resisted the urge to touch it, or even mention it. He didn’t say anything either. The sexual charge in the room was so thick you could cut it with a knife, at least for me. I don’t know what he was thinking, but his erect dick said a lot.
But I was trying to be a professional. I then massaged his shoulders again, remembering he said he wanted particular attention there, then his upper arms, lower arms, hands, then upper legs, lower legs, and feet, My aching wrists were shot!
I simply said “Finished!” and expected him to jump off the table. He spent a good minute just laying there and not saying anything. I was getting into a weird expectant space. What was he going to say? It was like tests in school. You think maybe you’ve done OK, but you may have failed miserably. You have to wait until the teacher hands the corrected tests back to you before you get to find out. And this was a really important test, in my mind.
He sat up ever so slowly, and pivoted around, dangling his long legs off the side of the table.
“Oh man, that was the most fucking excellent massage I’ve ever had!”
With that, he modestly went back into the bathroom to get dressed, as if I hadn’t seen his dick and all that. I mean, I saw him with an erection! How cool is that? Yes, I was going to like this line of work.
Right after James left, I called a couple of my closer friends, and then my best friend, Clinton. The first two guys turned me down, but Clint said “OK, as long as you don’t get weird on me.” We arranged a time for the next day.
All the rest of that evening, I was obsessed with his comment. By ‘getting weird’ on him, did he mean just because it was a guy giving another guy a massage, or did he somehow know I was tending toward gayness? This was still a time when I was not really sure what I was, and really didn’t want the whole world to know my situation.
I also called Michelle that evening, and she was happy to come over at 2pm.
I couldn’t wait for Clint to arrive at 10am. Fortunately, he arrived a few minutes early, because I was tearing myself to shreds waiting. It was a mix of nervousness, excitement, and I think maybe horniness, too. You see, I had been secretly hoping to get my hands on Clint, in a sexual way, ever since, well, probably around the fourth grade. A massage might not be sexual, but it would be the next best thing. I knew he’d have to be draped, but I was hoping to get at least a peak at his stuff at some point during the massage.
So Clint arrived. I’ve always liked his style. He’s of some sort of Scandinavian descent, with very light skin, hair so blond it’s almost white. Like me, he is otherwise medium-built. He’s also the kindest guy in the world. He’s polite and always-accommodating. Maybe that’s the real reason he accepted the massage. It may be that he didn’t want a massage at all, he was just going to do it for me. I was hoping he’d get some enjoyment out of it, at least.
Like I had done it a million times before, after a minute of chit-chat, I instructed him to go in the bathroom, take off his stuff, and return wearing only a towel.
He came back and I had him lay face-down on the table. The table was covered with the same sheet that I had used with James the day before. I hadn’t yet learned that you change the sheets between each client. Geez!
I asked Clint whether he wanted anything in particular, and he didn’t think so.
I warmed my hands, got some oil, and started on his shoulders. At first he was totally quiet, but then, same as James, he seemed to really get into my attention, letting me know with little quips of “Mmm…” and “Nice.” I worked my way down his back then his shoulders to his upper arms, then his lower arms, and his hands. Again, I was hoping he wouldn’t think it too ‘gay’ of me to massage his hands. He seemed OK with that.
Then I did his upper legs, calves and finally his feet. Having learned from James yesterday, I then whipped off the towel to start on his buttocks.
“What the fuck?” he practically screamed.
I was shocked. I didn’t expect that, quickly putting the towel back on, and explaining that I was going to massage his glutes.
“Oh, I see. Go ahead.”
Ah, I didn’t expect that, either! So, I took the towel back off, half-expecting him to tell me to put it back, but no, he was good with it, and I went to work on his butt. After a minute, I purposely pulled his ass cheeks apart a bit so I could see his anus. I wasn’t going to miss that opportunity. And, what a butthole it was! It was just ever so slightly pinkish, or maybe a brownish-shade of pink, and had slight radial wrinkles leading to the center. I also saw the back of his scrotum, which was drawn up, and had feather-like wrinkles. Very nice. Oh what I would have given for this massage to turn sexual.
After a minute, I asked him to roll over.
“Hey Benjamin, would you mind doing my butt a bit more first?”
Would I mind? Heck no! Without a word, I resumed on his butt. I noticed that when my fingers came close to his asshole, he seemed to push toward them, as if he wanted me to focus more on that area. So I did, slightly, just running my fingers along near where the color turns darker, about an inch from the opening itself. He didn’t seem to mind, and I was pretty sure he was liking it.
I decided I had to try something, but I knew it was a big risk. I figured I could brush my fingertips right over his asshole itself for a split second. If he freaked out, I’d just say, “Sorry, I wasn’t paying attention.”
But the thing is, I didn’t get up the gumption. I really wanted to do that, but was afraid it would be too much.
After perhaps a full five minutes of butt rubbing, I asked him to turn over again.
“Ben, if you don’t mind, just a little bit more.”
So, I did more. Now it was time to try the finger on the anus thing, and hope for the best.
I did it. I ran my finger directly over his anus. I don’t know what it did for him, but it increased the erection that had been in my pants for the past several minutes. He didn’t object, so after a few seconds, I did it again.
“Ben, Uh…”
I though he was going to tell me to stop, or maybe even call me a faggot or something.
“Benjamin, I, um.. well, I get erections easily. It’s not a sexual thing.”
For a second I didn’t understand where he was going with this. Then it dawned on me! He was having me do all that butt work because he didn’t want to roll over and have me see his erection.
Sounding exactly like the expert I wished I was, I tried to say as casually as possible, “Oh, guys get erections all the time, it’s no big deal.” The only problem was my voice squeaked a bit when I said it. I cleared my throat, and continued, “No big deal at all. Part of the business.” I had been so happy to simply see his anus, let alone touch it, and now it seemed I might not only see his penis, but it would be erect. This was too good to be true!
He pushed his hand against the table and rolled over. His magnificent erection stuck straight up in the air at a 90 degree angle. His ordinary six-incher was uncircumcised, and very white, especially there, and to my added delight, he was one of these guys who shaves his crotch. I’d seen a couple of shaved guys in the gym shower, but never up close, and never as magnificent as Clinton!
What does a professional massage practitioner say when seeing such a thing? Nothing. That’s what I decided. I knew I couldn’t throw a towel over it because it was sticking up too prominently. The towel would not only be a joke, it’s weight on his erect dick might hurt him a bit. So, I just went on with my massage. First his shoulders, then his upper arms, working my way to his hands. I hoped he didn’t notice that I was shaking a bit.
After that, I worked on his upper thighs. I really wanted to touch his dick or maybe his scrotum a bit at that point, but I knew that would be going too far. Instead, I worked my way down his legs, and then did his ankles and his feet.
Not only his erection stay solid, it was bobbing up and down a bit with every heart beat.
Now what? I could certainly sense that I was leaving something unfinished. And of course I knew what it was. Clint needed release. I really didn’t know how to respond, so I went back to the head of the table, pretending some more massage was needed. But what to do? I had already massaged his shoulders and neck. But not his face! Well, why not? So, I started gently rubbing his cheeks, his temples, and his jaw, thinking he’d stop me at any moment. But no, he held his eyes closed, and I could tell he was enjoying this very intimate massage.
Finally, there was nothing more I could do.
I told him I was finished, and remembering how James had gotten up so slowly, I let him know he could take as long as he needed to get off the table.
After only a few seconds, Clint practically ran to the bathroom, with his erection waving before him. He took a bit longer in there than I expected, I’ll bet he jerked off. I know I would have.
Finally, he emerged, a bit red in the face, and thanked me profusely. He also apologized for the erection. Without thinking it through, I told him something that was perhaps a bit more forward than I intended, I said, “I enjoyed seeing it.”
The minute he left, I sat on the table, took off my own clothes, and rubbed myself to a spectacular orgasm.
Two o’clock came, and along with it, came Michelle. I told her the same thing, go in the bathroom and change into a towel. She came out after a few minutes and laid down on my table.
I started on her in the usual way, working her neck, shoulders, upper arms and so on. When I got to her hands, she said, “Ben, I’ve had massages before,…”
Alarm bells went off in my brain. What was she going to critique? What stupid thing did I forget or not understand?
“…but this is the best ever!”
I thanked her for the kind words, and then worked on her thighs, calves, ankles and feet. I then came up to her butt, and trying to leave the towel in place, massaged her butt. She asked me whether the towel was necessary.
I removed it, and continued on her butt. I couldn’t resist looking at her asshole, and was kind of amused to notice that it really looked about the same as a guy’s asshole. Like her pussy and nipples, it was somewhat darkly pigmented. I also noticed her ‘wound’ – the way I though of vaginas. Somehow, I was not only not attracted, I was kind of grossed out by it. I know I shouldn’t feel that way, but I did.
I had her roll over and was confronted with a new problem. With guys, you can massage their chest just like the rest of their bodies. But what do you do with a woman?
Something else I got from my dad: Communication. He always told me, “When in doubt, communicate.” So I just asked her, would she like her breasts massaged?
She assented, and voluntarily removed the towel, so her whole self was naked before me. You know what? She was really quite attractive, wound and all.
I did her arms, her hands, her thighs, lower legs and feet. Then I came back up, got the front of her neck, her shoulders again, and then, gingerly started rubbing and squeezing her breasts. She loved it. I noticed that ever so lightly rubbing her nipples sent some sort of shiver through her, which she seemed to particularly enjoy.
Something came over me, and I worked lightly down her stomach, and then I started rubbing around the top of her crotch hair. I touched her vagina, and she didn’t object. Interestingly, I found it easier to touch a woman’s vagina than a man’s penis. Go figure! Maybe because it meant less to me.
Michelle became vocal, directing me in exactly how to touch her. She had me rubbing generous amounts of oil on her clitoris, then she wanted me to stick a finger inside. I really didn’t want to do that. It seemed kind of gross. But she’s a friend, and she really seemed to want it. I can understand being horned up, even if it’s a girl, so I went ahead and did it for her. It was surprisingly warm in there. I had experienced that warmth before with my dick, but this was the first time with a finger. She instructed me to turn so that my finger could curl upward and rub the area it contacted inside her. Then she wanted two fingers in there. I was just about to quit when she suddenly started moaning and arching her back. I realized she was orgasming. After a few seconds, I pulled my fingers out.
“No!” she screamed, then told me to put my fingers back in and keep going. So I did, and brought her to a second and third orgasm before she finally calmed down.
Oddly, I enjoyed doing that for her. Very much.
Right after her appointment, the phone rang. It was Kers, a friend of James. He heard I was giving free massages. Would I have time to do him?
Thinking so fast that I’m proud of it, I said, “Yes, but they’re no longer free.”
“Oh.” He sounded crushed.
“Well, how much?”
Thinking quickly again, I said “Sixty bucks.”
Silence.
“Oh Dude, I’m sorry, I don’t have that kind of money.”
“How much do you have?”
“How about $20?”
“Deal!” I would have done it for free. Especially since I know Kirs a little bit. He’s another tall guy. He kind of looks like a modern version of Cary Grant.
He came over the next day, and everything started in the usual way. He, too, didn’t want the towel when I did his butt. He too, seemed to like it when I brushed my fingertips over his anus. He too, had a nice erection when he rolled over. I ignored it, of course.
As the massage was nearing a close, he said, “Dude, I was kind of hoping for something more.”
Sometimes I’m a bit thick. Trying to give him what he wanted, I started working on his shoulders again, more than happy to comply, even though my wrists and thumbs were hurting a bit.
“Thanks, that’s nice, but do you ever give…” Then he hesitated, and finally hoarsely whispered, “happy endings?”
Call me an idiot, but I didn’t know what he meant. I wanted to ask him, but thought that would be unprofessional. So I had a problem, how could I possibly give him that, whatever it was, since I didn’t know what it was? Remembering what my dad taught me about communication, I went ahead and asked, “What’s that?”
“Really? You don’t know? OK, so… um,.. it’s like I’ve got this boner, and I guess it’s a natural effect from massage…”
I was starting to get an idea of what he wanted.
“Yes, lots of guys get erections during a massage.” Like I had actually done ‘lots of guys’.
“Well, can you do something for that?”
The rebel in me came out. I was delighted to help Kirs out. “Got it!” and with that, in a kind of going for broke attitude, like the first time jumping off a diving board, I grabbed his very erect penis like I owned it. It was the first time in my I had touched a penis besides my own. It was surprising in many ways. First, it was warm. Then, it was really harder than I expected. At the same time, the skin over it was very soft and flexible. I knew all this from my own dick, but somehow, feeling it on someone else reminded me how warm, hard, and soft a penis can be, all at the same time.
I started pumping it up and down the same way I jerk myself off. He shot three or four good squirts into the air almost immediately. That was easy, and it was fun!
He cleaned up, gave me my $20 and left. I was now, officially, a professional! I had collected money for a massage. It was time to hang out my shingle.
But the problem was how to give massages without a license, and stay legal? Well, I had looked that up on the Internet, I had studied long and hard one evening, and came up with the answer. You can’t legally advertise yourself as a massage practitioner, but you can teach massage all day long. It turns out you don’t need a license to teach. I found that to be an amusing loophole, and one I was planning to take full advantage of. All I had to do was figure exactly how.
I posted in the services section of Craigslist that I would teach one-on-one hands-on massage ‘tutoring.’ Fifteen minutes later, my post went live, and literally sat near the phone. I kept expecting the phone to ring, and kept checking my email. Nothing. A couple hours later, I went back to Craigslist, and someone had flagged my ad. It was gone. I reposted it. An hour later, gone again! To say I was disappointed would be a huge understatement. Now what to do?
I figured out that my ad was posted in the wrong place, and probably written incorrectly. I tried several experiments over the next few days, but nothing worked. Sometimes the ads stayed up, but no one responded.
In the meantime, James came around again. Since Kers had arrived because of James, and because James had been so appreciative of his first massage, I gave him a free massage.
Taking note of Kers’ interest in the “happy ending” I came right out and offered it to James, kind of cringing as I did so, because there’s no telling how he’d react.
Here’s what he said: “If I give you a blowjob, it’s gay. If you give me one, it’s just a guy getting a blowjob.”
I freaked. “Who said anything about a blowjob?”
“No, I mean, yes, I’d like a happy ending.”
I massaged James in what was becoming the usual way and he enjoyed it. When I started to give extra attention to his sore shoulder, he said that I had cured it the other day, and that he’d rather have me spend more time on the ‘ending.’
I sped through the rest of the standard massage steps, then went right to the heart of the action. There he was, laying on his back, with his erection laying against his belly. Evidently when one’s dick is that large, it doesn’t stick up in the air. Gravity lays it down. I gingerly put my fingers around his warm, rock-hard penis, and he was obviously in heaven. I started stroking up and down. He didn’t cum right away, and I was glad, because I truly liked doing it.
After five minutes, he still hadn’t cum, and my arm was getting tired. I thought I’d try something based on what I thought I might like in similar circumstances. With my other hand, I started lightly squishing his balls back and forth, kind of massaging them in his sack. He said “Mmm,” so I knew I was on the right track. Moments later, he ejaculated all over my hand and his stomach. I was almost as delighted as he was. After he left, I sat on the table, remembering his penis, and jerked myself off to a quick and strong orgasm.
While waiting for Craigslist to give me some clients, I was thinking about this “happy ending” thing. In my limited knowledge, it seemed most of the guys became erect during massages, and even Michelle became quite horny. No doubt they’d all like happy endings. Maybe I should specialize in some sort of masturbation practice. Little did I know at the time that most massages in the world aren’t like that. I was to learn years later that most massage practices are ‘legitimate’ and happy endings are rare.
Being frustrated by the lack of response on Craigslist, and at the same time wary of circumventing the law, and also being a bit of a rebel, I came up with an idea.
There was no chance of being illegal if I didn’t touch people at all. What if I offered some sort of instruction, not massage? What if I taught what I know? But what exactly do I know best? That would be masturbation. Somehow, I could teach masturbation. That would certainly be easier on my thumbs and wrists which were aching after every massage.
I called Michelle, the only person I knew who could be objective and supportive, and told her all about my new idea. I could imagine her pretty dark eyes sparkling on the other end of the phone conversation as she said that was a ‘fantastic’ idea. She even helped me flesh out some of the details.
I stayed up almost an entire night learning advanced masturbation techniques on the Internet.
I called James and Clint, and explained to both of them what I was thinking of. A few days ago, I could never have mentioned such a crazy and rebellious idea. But since their happy endings, I figured they’d be on-board with helping me out. I was right.
Clint was first, and I told him to pretend he was a new client. I was going to talk him through an advanced masturbation session. Although I wasn’t going to be touching him, he was still all in favor of the idea.
He came over, took off his clothes, and sat on my massage table. He had an erection even before his pants came off. I started filling the air with instructor-like talk, kind of hypnotically guiding him through a couple of grips, showing him how to rub the palm of his hand over the head of his dick for a very sparkly sensation, how to pull the frenulum to stay near the point of orgasm longer, and so on. All the things I had learned, some of which I hadn’t even had time to practice on myself yet.
It worked well, and he shot a good load of cum within just a few minutes. I thought it would have taken an hour or so.
Next came James. We did pretty much the same thing. He wasn’t hard when he removed his pants, but it didn’t take him long to get that way. I really enjoyed watching him stroke his big, black, shiny, eight-incher. He particularly liked the frenulum pulling thing. After he ejaculated, he told me that it was especially ‘hot’ having a guy watch him masturbate, causing me to think I was onto something big.
I went back to Craigslist, and posted that I was teaching advanced masturbation techniques.
An email came in. A real, honest-to-goodness client, not some sort of spam for a change. I had the guy come over, and although a bit nervous, I did a good job, and the session went well.
This fellow, Greg, was a fat, forty-something, balding fellow. Not much to look at, but with an enjoyable, jolly personality. With Clint and James, I had started to develop a kind of spiel, and so I started the same way with Greg. He got hard in rapid order. I was a bit concerned that he might not, and it seemed he didn’t have much to work with. When he first removed his pants, his penis was not much more than a walnut-size nub sticking out above his scrotum, and in a field of long straggly gray and black hairs. But once it started to grow, it made it to a full six inches. In less than fifteen minutes, he ejaculated. Less than five minutes after that, his pants were back on, he was out the door, and I was $40 wealthier!
For the next two days, nothing at all. I was starting to get depressed when the phone rang. It was another customer!
I had him come over, and we went through the same procedure. This guy was probably around 70 years old, but did just fine in the erection department. He, too, came within minutes, thanked me profusely, and left after paying not the $40 I had asked, but a crisp $50 bill. I went to make change, but he said, “Keep it.”
The phone rang again, and I had another client, a guy named Nelson. I had him come over, Seeing him, I figured this might be a particularly nice session. The guy was good to look at. He was short-haired, fairly tall, thin, and very fit. I figured him for some sort of athlete or at least a gym rat.
But something was off. I can’t quite explain it. He didn’t seem as friendly as the others. His sentences were short and clipped. He asked me to explain the procedure in its entirety. I complied. Then I asked him whether he was ready to get started, and let him know that if for any reason he didn’t want to proceed, it would be OK.
He was reluctant to pull down his pants. I figured he was just shy or something and thought maybe I’d just have to talk with him a while so he could relax enough to be comfortable naked in front of me.
He then asked me whether I’d pull down my pants. As I had practiced in my mind, just in case anything of this sort of thing came up, like if a policeman or something wanted to check out my service, I told him, no, this was just a lesson for him.
Suddenly, he smiled so big it was almost a laugh. I didn’t understand. He then explained:
“You passed the test. I’m an undercover officer. There’s nothing to be afraid of. You are, in my opinion, and I’m sure under the law too, doing nothing illegal.”
Whew! I can’t tell you what a relief that was. In the back of my mind, the thought of being busted for something hadn’t quite gone away.
So Nelson left, but then for the next two days, nothing.
Finally, the phone rang. “Hey, I’m a friend of Nelson. He told me about your service, and I’d like to get me some of that.”
I invited this new guy over, and he jerked off in front of me, having a delightful time in the process. I got my $40.
Later that same day, I got another phone call, and sure enough, it was an other friend of Nelson. When he arrived, and before he disrobed, he explained that he was also a detective, but wasn’t here on business, and assured me he was in total alignment with what I was doing. I talked him through a session, and it went great.
To cut a long story short, I had more than 40 clients over the very next month, Most were friends of Nelson, or friends of his friends. Within a year, my business grew to a full clientele, and I continued to learn a lot about my very specialized business.
For instance, on day, an older guy named Andy came by. He was in his mid-sixties, exceedingly friendly, totally fit, and rather good-looking with striking white hair and a matching, neatly trimmed white beard. He kind of reminded me of the Kentucky Fried Chicken guy, Colonel Sanders. I started in on him, and found his whole self surprisingly attractive for a guy more than three times my age. It felt reassuring to know that guys can still be like that at that age, because that’s what I hope to be like someday.
We started in on his session, and I really felt I would have liked getting naked along with him, and jerking him off, or maybe have him jerk me off, or maybe even a blowjob or something.
I got the sense he was playing along with me, as many of my clients did. They already knew this advanced masturbation stuff, but I think they just enjoyed the company, and maybe having a guy watch them jerk off. I think too, that they liked the weirdness of it. I mean, how often does a guy get masturbation lessons?
After a while, Andy offered to teach me some new things. For a second, my professional pride was hurt. Like I’m supposed to be the expert here. But Andy was disarming, and I thought about it logically: Yes, if there’s more to be learned, then I certainly ought to find out.
So we talked a bit after his session. I offered him some tea and some crackers, and we sat around my mom’s kitchen table talking some more. I had an hour before the next client, and I was really enjoying my conversation with Andy. He invited himself over to see me during my next opening, which was two days away, and teach me some things.
He wanted to do it for no charge, although I gladly would have paid him something. I mean, if he actually had anything useful, it would make me a lot more money!
I was already way beyond my dreams, making over $4,000 per month, got my mom’s mortgage caught up, we were eating better, and had a few new things, but I could always use more. Maybe Mom could even retire!
During the next two days, and especially during various clients’ sessions, I though a lot about Andy. First, there was something so likeable about the guy. He even smelled nice. But what could he possibly teach me?
Finally, he arrived, and I had a two-hour block for him. As soon as he was in the door, he threw off all his clothes, but then he did something unexpected. He told me to take mine off also. I started to object. I mean, this has always been a one-way business. But he said this wasn’t business as usual. He wasn’t a client. He was the teacher this time, and the lesson required that I be naked. Surprisingly, I was uncomfortable with taking off my clothes, but what could I say? I was also secretly delighted.
In all that time, with all those clients, all I ever did was jerk myself off. Never did I even touch another guy. The last times where when I massaged James and Clint with their happy endings.
At first hesitantly, because it was a bit weird, and then quickly finishing, I took everything off. It was easy to do, because I kept the house warmer than usual for my clients, so they’d be more inclined to get naked. Anyway, there I was, already erect in front of old Andy. I was simultaneously embarrassed, and yet proud of my erection.
He had me lay down on the table and the very first thing he did was a surprise. I figured he’d grab my dick and do, well, something. Instead, he reached forward with just one fingertip, and ever so lightly touched my frenulum, the little fold on the underside of my penis near the head.
My penis jumped nearly an inch. It felt very, very nice. I had never experienced anything like that. After a few seconds, he did it again, and it felt just as great as the first time. He did it several more times and it was excellent every time. He kept doing it for several minutes, and although it wasn’t orgasmic, it was absolutely delightful.
Then he did another weird thing. He grabbed my frenulum between his thumb and the side of his first finger, and lifted my penis up by it. Now that, almost instantly, felt orgasmic. Oh, I didn’t cum, and wasn’t even close. But, he kept pulling, and then shaking my penis a bit, still pinching the frenulum. If he kept it up, I would cum.
Andy was an artist. He knew exactly when to quit and move on to the next technique. He asked whether I liked intensity. At that point, I was up, literally, for anything.
He put some of my massage oil on the palm of his right hand, and grabbed the shaft of my penis with his left hand. Then he lightly rubbed his right palm over the tip of my penis. Now, I had instructed my clients to do this many times, and it seemed to make them flinch, although delightfully. But I had never had it done to me.
It was the most ungodly feeling! Kind of a tickle, but no, something almost torturous, but not that either. It was very hard to take, yet I loved it. He kept rubbing, and I was squirming all over the place. He told me to pretend I was tied down and couldn’t get away. He kept rubbing his palm over my glans, and I kept squirming and something more. I discovered that I was kind of shivering or maybe you’d call it jittering. That sensation has no equivalent. If you haven’t experienced it, you’ll have to give it a try. The only problem is, you can’t do it to yourself. You won’t stand for it. You need someone, and it doesn’t matter who – could be a man or a woman – to do it to you.
In time, it transmuted into something less difficult to accommodate. I settled down, and noticed that it had changed into a sort of ‘gotta-pee’ feeling combined with a ‘gonna-cum’ feeling. Yet, neither happened. I would have loved to have that happen all day, but Andy explained that even with the massage oil, it would eventually irritate the skin of my glans.
So far, all of these techniques were magnificent, but I couldn’t use them with my clients, because they are about one person ‘doing’ another. However, I was having thoughts about expanding my business for some of my better clients into mutual sessions of some sort.
Andy’s next trick was something I could indeed use on my clients. He had me masturbate myself just to the point where I feel the orgasmic feeling coming on, then stop. I did this a few times and it was nice, but also frustrating because my body really wanted me to cum.
Then, he wanted me to keep going when I started feeling like I’d be ejaculating momentarily, but greatly reduce the stimulation. But only for a second or two until the feeling started to subside just a little bit, then resume full stimulation. He explained that it is possible to stay in orgasm, without ejaculating, all day long, if one wishes, with practice.
On that first occasion, it almost worked for me. I was in that pre-orgalmic state for perhaps an entire minute. I felt new sensations I had never felt before. One was a sort of horniness deep in my lower stomach. It was almost frustrating like the previous sensation. I really wanted to cum, but it wasn’t quite the same. It was remarkably satisfying. Because for that minute, I didn’t cum, but I was orgasming, and it was OK. I also felt a delicious momentary stinging in my urethra. A moment later, I was having actual dry orgasms. I felt some contractions, but nothing came out. This was truly amazing, and something I never expected was possible.
Oops, I slipped over the edge and ejaculated. Andy cheered me, and told me with practice, I’ll be able to stay right in the middle of an orgasm for minutes at a time. He also told me about some variations in which I can have mini-ejaculations, in which I cum just a drop or two at a time, but can stay hard and in the mood, doing it over and over, for hours, if so desired.
Once I went over the edge, I felt it would be nice to reciprocate, and he must have figured I would, since he had been naked also. So, I got him on the table. His penis was already hard, about 5 inches long, kind of thin, circumcised, and sticking straight up. Like me, he shaves all the hair from that area. His chest was covered in a blanket of thick white curls.
Andy wanted the glans – head of penis – rubbing thing, and I gave it to him big-time. He squirmed just like I did, plus he yelled and laughed. Then, he wanted me to massage his balls. I was afraid to do it as firm as he wanted, but he kept telling me to squeeze harder.
The trick, he taught me, is to avoid squeezing the area on the rear of the testicles near the top where the spermatic cords attach, which he called the ‘epididimis.’ That’s a sensitive area, and probably fragile too. But whereas the testicles register pain with the slightest impact, they can take a rather tremendous squeezing force anywhere except the attachment area.
He let me know that he’d say something if I squeezed too hard. Still, I wasn’t squeezing as hard as he wanted. He told me that balls aren’t like grapes. They’re more like raw chicken gizzards. They have a thick rubbery covering that won’t burst or anything like that.
I found his pain threshold, and it was really high. He explained a man will feel extreme pain well before any damage can be inflicted. It’s hitting balls that hurts, not squeezing, unless it is very intense. He also let me know he’s not necessarily typical. Some men don’t like their balls squeezed at all.
Finding the amount of pressure just short of where it hurt him, I continued to squeeze both balls simultaneously, one between the thumb and first two fingers of each hand. Sometimes, they’d suddenly slip to another position in his scrotum, which made him jump, but he said he particularly liked that effect. Suddenly, his penis started spurting cum, even though I hadn’t been touching it. He was very happy indeed.
Andy and I hit it off, and started seeing each other regularly, generally after all my clients in the evenings. We’d practice our techniques on each other, right there on the massage table in the living room. Sometimes my mom came home in the middle of our activities, but she was fine with it, just ignoring us, and going into the kitchen or wherever she was headed.
She seemed to like Andy, but who wouldn’t? We found out he was a former golf pro who had been frugal with his money in his mid-twenties to mid-forties, and has been living off his investments ever since.
One Saturday I came home from some errands, evidently sooner than Andy and my mom had expected. There, on the massage table, was my mother, getting a treatment from Andy, and in the throes of ecstasy. He had two fingers in her vagina, and his index finger from his other hand was in her butt, and she was bucking and screaming like a wild horse. She’s not at all overweight, but her large breasts were flopping around like crazy. I was surprised, and momentarily shocked, to see that she had no crotch hair. Heck, truth be told, I was absolutely shocked to see my own mother, naked, and having a wonderful sexual time.
I thought under the circumstances, the thing to do would be to instantly let them know that I had no problem with what was going on, so I smiled, and said, “Don’t let me stop you.” They didn’t.
That started happening more and more often. And why not? She’s only about ten years younger than Andy.
What you may find more shocking is what happened with Andy and I. Our sessions became more. Much more. It started with the time he was doing something to me, and I suddenly pulled him toward me and kissed him. As soon as I did that, I knew I had crossed a line. He didn’t back away. More than that, he kissed me back, turning in to Frenching. I was delighted!
In one session, he added another technique. He took his index finger, and rubbed it around my anus a bit, just like I had done a year ago to James. But then he lubbed it with massage oil and very slowly slipped it in my ass, right there in front of my mother who had been enjoying seeing her son have so much fun. I was rather proud of her seeing my erection, and the man, the sexual being, I had become.
At first his finger didn’t feel right. It felt kind of achy, but only for a moment. Suddenly, it felt great, and I wanted him to jam it all the way in. But he took a long time putting it in, kind of twisting back and forth a bit as he gently pushed. Finally, it was all the way in, and I couldn’t have been happier. But there was more coming: Next, he curled his finger forward, found my prostate, and massaged it. I felt a bit like I had to pee, but something much nicer.
After a minute, he pulled his finger out – very slowly. I could have sworn his finger was a foot long. Then he put two fingers in. It kind of stung, so he quit for that session. He told me there’d be more of that, but didn’t give any details.
In other sessions, we started sucking each others dicks and that became so common that we enjoyed it almost daily. Sometimes we cum in each others mouths, which was nice, and his cum tasted nice, but we usually saved our ejaculations for all our masturbation-like activities. A couple of times, my mom sucked Andy right in front of me. You’d think that would be disgusting, but no, it was hot! I kept hoping she might volunteer to suck me, but that never happened.
In the next few weeks, Andy and I did the anal finger thing to each other. One day, he handed me a condom in a packet and told me to fuck him, much as I had seen him and my mother do on the massage table a few times. Of course, he meant fuck him in the ass, however. I didn’t hesitate at all. I got right on that job. My super-hard cock went right in. It was probably a more sudden thrust than Andy might have wanted, but to his credit, he seemed to enjoy my dick in his ass completely. It was the first time I had ever butt-fucked anyone, and I must say it was way, way better than when I fucked Michelle in the pussy. An ass is much tighter, and well, I have to say, more enjoyable. Especially Andy’s ass.
In that session, he managed to get three fingers in my ass. I really wanted more, I craved more, but he said that we’d do that another time.
The next session, we went all the way. He put on a condom, put me on the table on all fours, and fucked me. That in itself would have been sufficient to be a cherished memory for the rest of my life, but something else happened too. My mom sauntered over, reached under me, and as casually as if she was making a salad, she pulled on my penis a few times while he was in me. He came and I came at the same time.
It didn’t take long for Andy and my mom to get married. They moved out of the funky little house, and into his big house in the suburbs. Meanwhile, I bought a home and rented an office in town, and my business continues to grow. I still teach advanced massage to beginners, but offer a fuller range of services to the established clients. Oh, and I charge a lot more than $40 per session these days!
My mom is happy to share Andy with me, and often all three of us play together. However, another client came into the picture. His name is Ralph and he is just a year older than me. He started out like any other client, but things soon progressed. He especially appreciates rebels like me. No, he especially appreciates only one rebel, me. He loves me. And I love him to death. And he and I live in my fancy new house, and we practice all sorts of techniques on each other.
One of us is supposed to be a bottom and the other a top. But we’ve never figured out which one is which. We just play every which way.
