by Jenelle Watson
Ever since I first touched a penis, I’ve been fascinated by them. Guys who cross my path generally get lucky. Very lucky. I’m Jenelle Watson, and here’s my story.
I got a late start. I think my mom protected me more than most young girls because of my looks. I’m short at 5’5,” skinny, have large breasts, long, straight, light blond hair, and I tan to a nice golden brown. I guess I have been fortunate. My heart goes out to women who are a bit rotund, or don’t have a certain look.
You’d think that being fairly good-looking, I’d have my pick of guys, maybe even too many. Instead, I think guys are afraid of me, like I’m too good for them or something, and that has been a detriment. That’s because I’m kind of a horndog. I really like some sexual activities, and for a long time, I wouldn’t have cared a bit if more guys would have approached me.
You may notice I said some sexual activities. Here’s the thing: I like giving handjobs. They are what I call the ‘laying on of fingers,’ and what I do may even have healing qualities.
It started soon after my eighteenth birthday. That’s when my loving mother decided to loosen the reins a bit. She actually let me start dating some boys. However, before I could go out with them, she insisted that I bring the guys by for her to meet. I don’t blame her. According to what she has told me, she was hassled more than once by men who weren’t always full of good intentions.
So, this one guy from high school, Franklin, was a real knockout. He was dating the most popular girl for a long time. They finally broke up because she wouldn’t have sex with him. I happened along at the right time to pick up the spoils. It’s just that I didn’t know why they broke up at the time. If I did, I would have picked someone else.
Franklin and I got to talking, and I found him enjoyable. He was humorous, and good to look at. He was one of those tall kids from the basketball team. Captain of the team actually. He kept his hair kind of long, and was growing a bit of e beard. He had the most attractive penetrating blue eyes.
The way he won me over, however, was in conversation. Every time we got to talking, he kept asking about me, not the other way around. Most of the people I’ve known so far, guys and girls, talk all about themselves ninety percent of the time.
He seemed very pleased that I was an A student. He wanted to know what I wanted to do for a living. I wanted to become a psychologist, and in fact, that’s what I ended up doing. He wanted to be some sort of sports coach, and that’s what he’s done with his life. Good for him. But, I’m getting ahead of myself.
I brought him home that one afternoon, and to my surprise, my mom liked him right away. So, we were able to start dating. All went well for a few weeks. We kissed. Boy, did we kiss! He was the first guy I ever Frenched, and it was twice as good as I would have imagined. That night, I masturbated myself to a great orgasm just remembering kissing Franklin.
Things started changing. He wanted sex. At first, he was very polite and patient. But as we got closer, and I was really starting to fall for him, he became more insistent. At first, he had round-about ways of asking. Like, he’d start a conversation with “Don’t you ever get horny?” Then, “What do you do about it?”
I was honest and told him I masturbated. That was probably a mistake, because for the next few days, all he could talk about was masturbation.
He became worse. Pretty soon he was just saying things like, “Let’s fuck!” and ‘or else’ was implied.
Now, I really liked Franklin. When he wasn’t being all annoying about sex, he was really sweet, caring, and did I say, good looking? So, I had to do something. But what?
Talking it over with my younger sister, who often seemed to have the wisdom of someone much older, she said quite simply and shockingly, “Jerk him off.”
I was like, “What?”
“Really. Boys like that, and you risk nothing. You lose nothing, not even any dignity, or at least, as long as you do it right. It has to be a gift. It can’t be because he asks for it.”
“Well, how many guys have you jerked off?”
Sheepishly, my wise sister admitted, “None.”
We laughed. Funny thing is, it started a thought process in me. Within a couple of days, I knew it was exactly what I had to do. Not only that, when I thought about it, that was what I wanted to do. Just imagining it, I got a tingle in my lower belly.
Thing is, I didn’t really know much about it. Oh, I’d seen cock pictures on the Internet a time or two, but how do you actually jerk a guy off? How long does it take? What kinds of things can you do wrong? I had a lot of questions!
I looked the topic up on Wikipedia of all things, and found a surprising lot of information. I also found some other websites with a wealth of information, but I believed much of it was wrong or just plain crazy.
The perfect opportunity came along. Franklin’s nineteenth birthday was coming up the following week. I hadn’t bought him anything because I didn’t know what to get him. I though, ‘A basketball? No, silly. A book? But what kind of book would a boy like that be interested in? How about a Swiss army knife?’ None of that made sense. But a handjob. Now, there’s a gift I thought he might just enjoy. And, being unwealthy, I liked that it wouldn’t even cost me anything.
His nineteenth birthday was on a Thursday. I waited until after school, and then invited him over to my house. By now, Mom was fine with Franklin, and even allowed us the run of the house when she was at work.
My sister offered to stay out of the house until 6pm even though she didn’t know exactly what we were going to do. It didn’t feel right to reveal such details to her. But she knew I wanted some alone time with my boyfriend, and she was glad to help. My dad was on a business trip in Colorado. So, I had from approximately 4pm to 6pm to give Franklin his present.
He came over, and I think he had an idea something special was going to happen. We sat on the edge of my bed and talked a bit. I became surprisingly nervous. In my mind, it was a simple procedure. But now that the time had come, I felt like it was a very big deal indeed. I couldn’t quite figure out how to steer the conversation and I almost chickened out.
Then good ol’ Franklin comes out with “So when are we going to fuck?” The poor boy knew nothing about subtlety, let alone romance.
That was my opening. “We’re not going to fuck anytime soon, so get over it. However, being your birthday, I have something very special for you.”
I can’t imagine what that must have done to his mind, but I didn’t give him any time to think about it. If I didn’t act quickly, I’d lose my nerve.
“Frank, pull down your pants.”
“You heard me, don’t act so surprised.”
“Can I see your boobs first?”
He stood up and started unbuckling the belt he was wearing. He then opened that little button, unzipped, and dropped his pants down around his ankles.
I became surprisingly excited. I didn’t expect my reaction. There was that funny tingle in my belly, and even in my vagina. Oddly, I felt a little wetness down there also. I hadn’t even seen his prick yet. Again, I almost chickened out. I was thinking of telling him it was a mistake, or I wasn’t ready, or something like that. But that’s not my style. My parents taught me to see projects through.
At that point, he hesitated.
“Keep going,” I coached.
His face was turning red. I swear, he even seemed to be shaking a bit. I didn’t know it was that important to him, and seeing that, I knew that no matter what, I couldn’t quit now.
He hooked his thumbs in the waistband of his boxers and just stood there. Again he asked, “Really?”
Trying to sound annoyed, I said “Yes!” But I think it sounded more like some sort of desperation.
Next thing I knew, his underwear was down by his knees and I saw, for the first time in my life, a real, live penis. It was only about two feet from my face.
Now you might think that I would have been frightened, grossed out, or something along those lines. Not so. I was fascinated. Like an astronomer seeing a new planet.
It wasn’t as big as I imagined. I was expecting something long and sticking out. This was just a little wrinkled thing with a pinkish-purple tip sticking embedded in a nest of black hairs. Below that was a hair-covered little baggy thing, which I recognized as his scrotum.
Now, to some people, that may not be a pretty picture. But then, I suppose an insect that’s really ugly still looks great to an entymologist. I was in love. Not so much with Franklin, although I was falling in love with him. No, I was in love with what I was looking at. Why his genitals had that effect on me, I did not know then, and I still don’t know.
He was just standing there. I glanced back up in his eyes, and he looked like a deer caught in the headlights. Somehow, I thought he’d be all macho about this, but he was, well, he looked kind of nervous or scared. I told him to sit down on the edge of the bed. He complied silently.
I walked over to my computer desk and grabbed my rolling chair, bringing it to the side of the bed. Sitting down, the one thing I wanted more than anything else in the world at that moment was to touch his lovely penis.
So I did. I found it to be warmer than expected, soft, and ticklish.
When he flinched at my touch, I thought somehow maybe I had hurt him. Were penises that sensitive? But no, it tickled him. I tried touching his scrotum instead. Again he flinched.
Thinking that light touches are more ticklish than full on touches, I then just grabbed hold of his penis. He jumped again, but this time, he apologized. He said my hand was cold, and he didn’t mean to jump.
Hmmm. What to do? I knew what I wanted without a doubt. I wanted to really get to know his penis, and maybe his scrotum with those balls in it, too.
I had a plan. I went across the hall to the bathroom, and warmed my hands under hot water. Yelling from the bathroom, I told him to take all his clothes off. When I got back, he had complied, and this beautiful guy was laying down, entirely naked on my bed, his clothes a heap on the floor.
The next part of my plan was to help him overcome the ticklishness. I had him roll over, and started massaging his shoulders. No flinching. OK, so then I went on and massaged his upper arms, his neck, then his back. All the while, I was staring at his butt. It was quite different than mine. His was covered with a course array of black hairs. I rather liked that and so I massaged it also. He was starting to go “Mmmm” and “Nice.”
After what felt like an appropriate but also interminable amount of time, I instructed him to roll over. He didn’t want to at first, asking me to massage his upper legs. I did. Then I asked him to roll over again, and he still didn’t want to.
“Come on, speak boy,” I replied jokingly, but knowing something was up.
Instead of telling me whatever he was trying to say, he just went ahead and rolled over.
I didn’t realize what was up until I saw it, and it certainly was up. This guy had a much larger penis than the one I had seen just a few minutes before. I didn’t realize they could change so much. Now what I saw was about six or seven inches long, at least an inch thick, and sticking almost straight up at nearly a ninety degree angle. The only way I recognized it was by the same pinkish-purple tip, but even that was now larger than what I thought I saw a few minutes ago. Could I have been mistaken at the change in size? Maybe it was bigger than I thought when I saw it soft. You see things like this on the Internet, but there’s no way to gauge size until you see them in person.
As I stared at it, I noticed something else, something I didn’t know they did: His penis was pulsing up and down just a little bit, evidently in time to his heartbeat. Way cool!
Oh, I so wanted to touch it. To hold it in my fingertips. So I did.
With my right hand, I reached out, and pressed my thumb and first finger across the shaft of his penis. It was surprisingly hard and soft at the same time. I noticed the skin was kind of loose, and so I moved it up and down a bit. At that moment, his penis started pulsing in a different way, and suddenly white stuff was squirting out of the top and splashing onto his stomach. Of course I knew what it was, but had never seen ejaculate in person. Wow, that’s all I can say. It wasn’t huge like a jet landing or a presidential election, but to me, it was the most exciting thing I had ever seen.
When the stuff stopped coming out, I reached forward and stroked him some more, wanting to see that again.
To my surprise, he pushed my hands away, covering his genitals with his own hands.
“Ah, I’m all sensitive now.”
“So, you want me to do it lighter?”
“No, when a guy cums, he cums.”
I didn’t know exactly what that meant, but kind of had an idea that the giving of his gift was completed.
To my extreme disappointment, he quickly mopped up the ejaculate, which he called “cum” with his underpants, put them back on, put on his pants, shirt, shoes and wanted to go home. He was polite, but brusque. He went home right away.
What the fuck had I done? I wanted this to be a great thing for him. It was close to what he wanted. He wanted to fuck. I wanted to give him a handjob. Was that the problem? It wasn’t right? Maybe it was so far from what he wanted that it upset him. I couldn’t understand, and cried myself to sleep.
For three fucking days, not a peep from Franklin. I texted him like twelve times. I would have texted a million times, but I felt like I was being too dependent. I left voice messages too, but no Franklin.
On the fourth day, he texted back. All he wrote was, “Sorry. Can we talk?”
I had a good mind to text back “No,” but I didn’t.
So we got together at McDonalds, and he kept saying he was sorry, that he handled it wrong. We couldn’t talk details being in a public place and all, so the meeting was short. I hoped to get back with him soon and sort this all out.
The next day, between classes, whispering so no one in the hall could hear, he asked whether we could do the same thing again, and this time he promised to do it right.
The problem was, it took more than a week to arrange a time when my house was empty, and his place, with all his brothers and sisters, was never empty.
Finally the afternoon came, and he was in my bedroom again.
I was more nervous this time than last, but one thing for sure, I was hoping to see that penis of his again. And his scrotum. I sure wanted to know more about that, too.
He started talking at once, which was unusual for him. I think he may have rehearsed. “It was me, not you! I freaked out. Plus, I was embarrassed. I wanted it to be something good for you as well as for me, and all I did was cum right away and ruin everything.” Then, I felt so weird I couldn’t even communicate. Geez! I’m so sorry Jen.”
“Well, you ought to be sorry for not communicating. As for the rest of it, you didn’t ‘ruin’ anything. Let’s see what happens if we do it again.”
That last bit might have been too forward, but whatever, right?
He started to pull down his pants. As a concession, at the same time I took off my sweater, T-shirt and then my bra revealing my boobs to him. I mean, he really wanted that, right? His underpants were just coming down as my bra came off, and he stopped in mid-flight, his underwear just covering his genitals by an inch or so. He simply stared at my tits, and froze in amazement, I guess. Now, I never thought they were all that special, but he was going nuts in a quiet, frozen sort of way.
It was time for me to break the trance. It seemed like he had been frozen for minutes, but it was probably only seconds. I gave him a light push on his chest, and he took the hint, essentially falling onto the bed while entirely removing his underwear. For a second his legs were up in the air, and I caught a glimpse of a dark hairy area around his asshole. I made a note of trying to see that later.
I had warmed the room with a portable heater, and warmed my hands before he came over, so I had him flip over and started the massage stuff again. He seemed to like it, and it seemed to calm him a bit, because after the frozen spell, he was kind of jumpy. I decided to massage his back and his butt for quite a while, hoping it would settle him down even more.
I think it did. When I asked him to roll over, there was that magnificent erection again. I hesitated but really wanted to touch it.
Knowing better this time, I asked him if he was OK with me touching it. Not whether he wanted me to to touch it, you understand, because it was all about me in that moment. I simply had to touch that erection of his. It may not make sense to you, and it doesn’t to me, but I simply had to feel his penis in my hand.
“Here’s the thing, Jen…” and then he hesitated. Finally, he blurted out, “I came too quickly. I wanted it to last. Your touch was just too magical and it drove me over the edge. This time, I might have to say something like ‘Wait,’ and when I do, let go for a bit. That way, I won’t cum too soon.”
I didn’t understand that entirely, but got the general idea. I guess when guys orgasm, it’s a done deal. They’re done, and can’t stand anything more. Not like us women, who can orgasm again and still like, even want, to be touched afterward. I did some reading online, and that’s what I discovered.
I tried to find all sorts of details on the male penis, handjobs and all that, and mostly what I came up with were sex videos. They didn’t excite me. In fact, I mostly didn’t like the actors. I did come up with one thing interesting: After a man ejaculates, he needs time to recover, sometimes lots of time. If you try to continue touching them at that point, it must be a bad tickle or something, because they call it ‘post-orgasm torture.’ Interestingly, some men play with the sensation, like a ‘can you take it’ sort of thing.
I reached forward, trying not to drool, and wrapped my fingers around that spectacular stick. Again I marveled at how it felt hard and soft all at the same time, and warm, too. With my other hand, I touched my fingertips to that pink top part.
I let go right away. After a minute, he said “Alright,” and I grabbed it again. Almost instinctively, I started moving the skin up and down.
Not knowing any better, I assumed at the time that all guys had such hair trigger orgasmic reactions. After a moment, I decided to check out his scrotum instead. It had a light covering of black hair, but I could see it had a sort of rubbery effect, and herringbone wrinkles leading to a central ridge. Very interesting! Later, I found out that the scrotum is polymorphic. It can take many shapes. As soon as I touched that, I got another “Wait!”
When he settled down again, I was able to touch his scrotum longer, and felt the weight and bulk of his balls inside. I felt them exceedingly lightly, since I had read that guys’ balls are sensitive.
Still, he moaned. I thought at first I was hurting him, but, no, he was very much enjoying it.
I came back to his penis, and just moved the skin up and down a little bit. I swear, it was only like a quarter-inch, and only for a few seconds. Sure enough:
“Wait!” Then, “Oh no,” at which point it started pulsating slightly again, and as soon as I realized he was going to ejaculate, he did. As he came, I wasn’t even touching anything, and the cum jumped up in squirts like five or six little ropes, and then fell to his stomach.
I rubbed my fingers in some and brought it to my nose. It smelled something like chlorinated fish. I kind of liked the smell.
Moments later, his penis lost its strength and started to wilt back down to the way I had first seen it.
“Happy birthday, Franklin!”
Finally, he was willing to communicate properly, and talked me through the whole thing. He had an orgasm, which resulted in ejaculation, and he felt like running out of the room again, but this time, he said, he wasn’t going to. And he didn’t. He and I talked about what had happened for a good half hour, as I stayed topless, and he bottomless in my bedroom. He thanked me profusely. Finally, we got hungry, put on our stuff, and went into the kitchen to see what we could put together.
Franklin and I stayed together for a while, but it wasn’t meant to last. I gave him several more handjobs. I thought it would stop him from begging for actual sex, but he kept right on asking, and wanting the handjobs too. So, he got handjobs, but no sex. He also got a couple of blowjobs from me. The first time, I spit it out. Too gross! The second time, I swallowed his cum, and it wasn’t too bad. In fact, it excited me.
That’s not all we did. Although I’ve masturbated a million times, I was wondering how much I was missing out on. I didn’t want to have sex yet, and the more Franklin bugged me about it, the less I wanted to fuck. But I did want a handjob of my own, and I let him know. He was delighted, of course.
So, one day in my bedroom, he masturbated me before I ‘did’ him. For the first time in my life, I took off all my clothes in front of a man. He took his sweet time, ever so lightly touching my pussy, then finally pulling it open a bit so he could look inside. This attention from him felt great, much like a good masturbation session, but better than anything I had ever done to myself. And I hadn’t even orgasmed yet.
I pointed out my clit, my peehole, and where my hymen used to be. He thought virgins always had intact hymens, but I informed him that that’s a myth. Most hymens end up broken through ordinary life activities or masturbation long before a virgin gets fucked.
I showed him how I rub my clit, and he did it with his rough fingertips. That sent me over the edge and I orgasmed. I had to explain to him that I wasn’t spent, and almost begged him to do it again and again. Yes, getting masturbated by someone can be way, way better than doing it yourself! It started to make me think that I’d have to try fucking some day soon. Somehow, even then, I realized it would never be with Franklin, however. He was, usually, a good communicator, but truth be told, he just wasn’t my guy.
Before high school ended, I gave handjobs, but nothing else, to two more guys. They loved it. I loved it, too! They both offered to do anything I wanted. They knew I didn’t want to have actual sex, so they offered what they thought I’d like: clit licking or handjobs. I declined. There was something about doing them, then masturbating later, by myself, that I particularly liked.
Oh, there was a big part of me that wanted to lose my virginity, but not with these jokers. I wanted the first time to be the ‘right’ guy.
So I got into college. I like education, and although the work was hard, and sometimes I objected to memorizing things that could be googled, but overall, my first few weeks were a delight.
I got to talking to an interesting guy in my biochemistry class, a strange prerequisite to psychology. He was in school on a basketball scholarship. Yes another tall guy. Our school doesn’t have any sort of championship sports department, so I was surprised they gave scholarships of that sort at all. Anyway, James was way taller than Franklin, like maybe 6’8.” He was thin as a rail, and kind of awkward in his movements. He kept his short hair and beard neatly trimmed. Oh, and he’s the blackest guy I had ever seen. He turned out to be second-generation pure African.
James spoke softly, and like Franklin had been at times, was a great communicator. He had me disarmed from the first time we met. I invited him to my dorm, and we hung out. My roommate, Junie, who was born in the Philippines, liked him too. The three of us went out to pizza one time, and she said, “Jen, if you don’t take him seriously, I’m going to steal him from you.” It was a joke, because plainly, James totally focused on me when the three of us were together.
Her comment didn’t worry me, but it did start me to thinking about James. I mean, I could truly picture being with him!
One night, she had gone out to dinner with her parents when James came over, and so, what do you suppose happened? Right, I gave him a handjob.
Now James is a confident man, and I think, a bit experienced in sexual matters. He accepted my gift with delight. Like with Franklin, I started out with a massage. I had James step out of all his clothes, then lay on my little twin bed against the wall. His feet hung off the bottom. It’s a good thing those dorm beds don’t have tailboards. Sitting on the edge of the bed, I gave him a bit of a backrub. Then I had him flip over, and he was already erect.
His penis was way different than the others. First, he kept all that hair down there shaved away, or lasered or something. He was smooth as a billiard ball. And speaking of balls, his scrotum was even blacker than the rest of him. His penis didn’t have a pink tip like the other guys had. Well, he had that, I supposed, but it was covered with skin that was so long it formed a point beyond the tip of his dick. His long dick, I might add. It was eight inches long at least.
After commenting on how sexy his dick was, for which he smiled from ear to ear and thanked me, I reached out and wrapped my fingers around the amazing thing.
He was like “Ah, that’s so nice.” Then, he seemed to lose all his muscle tension, laying as calmly on my bed as a person ever could. He just closed his eyes, and absolutely enjoyed my stroking. I pulled up and down, and up and down, and both of us were in heaven. It took a very nice long time before he squirted his cum. I was expecting a huge ejaculation based on the size of the man and the size of the penis. But no, it was just an ordinary five or six squirts. They looked amazingly white against his black six pack. When he was finished, he very quietly thanked me again, and promptly fell asleep.
I don’t know what prompted me, but I took off all my clothes, curled up next to him on the tiny bed, and fell asleep also as he wrapped his arms around me.
He was still there with me in the morning. So was Junie. That was a bit embarrassing. Both James and I were still stark naked, with no covers on, since it was a warm autumn day and the campus was stingy about air conditioning. We had central air, but somehow, it wasn’t very cool on a hot day. So anyway, there was Junie in her bed about six feet from mine, snoring away. She must have seen us when she came in. We got up, put on our clothes as quietly as we could, and left for breakfast. Either we didn’t wake her, or she pretended to be asleep. She never mentioned the incident.
My relationship with James grew and Junie kept telling me how lucky I was. She had a boyfriend too, but he was so ordinary in comparison. Her guy, Jason, was a regular, white, sweater-wearing, computer nerd. Nice, and I was happy for her, but Jason was no James! On top of everything else, my James was kind of a minor celebrity around the campus. Everyone knew him, or wanted to know him. I was proud to be seen next to him. I was also happy that he never once expressed anger, frustration or anything like that around me. He didn’t even swear. He was a bit religious for my tastes, but he didn’t try to convert me.
It wasn’t long before I knew it was James with whom I wanted to lose my virginity.
Well, I was all set, but he wasn’t. He said he just loved the handjobs, and the occasional blowjob I’d give him, but he wasn’t ready to have what he called ‘pre-marital sex.’
I didn’t see that coming. As a consolation price, he ate me out, not once, but a hundred times in the next few months. He also did some very cool things that I’m so glad I experienced with him. Things that I didn’t even knew existed.
Like one time, after rubbing my clit for a while, right before I was going to orgasm, he stopped. He took his finger off my clit, covered his first two fingers with my juice, and slowly introduced them into my vagina. No surprise there. That’s happened before, and it always felt great. But then, he curled his fingers forward, and started rubbing the front side of my vagina. I had heard about the G-spot, but never realized it was anything significant. I sure found out different, as I started quivering, and then had the most amazing orgasm of my life. It came from a different place. I mean, it felt like it was coming at me from throughout my whole lower belly, not just my clit and vaginal area. I had no idea! It was so strong I continued to quiver for several minutes later, and he had to throw a blanket over me, as I was feeling feverish.
A week or so later, just when I thought it couldn’t get any better, after I had given him another handjob, he did something else. Again, he coated his fingers with my slime. Then he instructed me to roll over and get up on my hands and knees on the little dorm bed. My ass was up in the air, fully exposed. He scrunched into a sitting position behind me. I thought he was going to put his fingers in my vagina from behind, but that’s not what happened. Instead, he started swirling my girl-juice around my asshole. No one had done that before, and it was fucking awesome! Not orgasmic, but just being touched there, was like the best, most comforting massage in the world.
And it got better. After a few minutes of that, he ever so gently placed a fingertip against my anus itself. I almost orgasmed then and there. He left his finger just sitting there for a moment, which I could have enjoyed forever. But then, he took his finger away, put it in his mouth coating it with saliva, and replaced it against my asshole. Then, ever so slightly, twisting back and forth a bit, he pushed it in. It had never even occurred to me that someone could do that. I had no idea what I had been missing out on.
He kept pressing his finger in, then rubbed around inside a little bit. I orgasmed big-time, and he hadn’t even been touching my pussy. Then, slowly, he withdrew his finger. I could swear it was a foot long. That’s a strange sensation, having a finger pulled out of your ass.
That whole ass experience got me to wondering whether guys like it too, so of course I had to offer it to James. He was like, “Really?”
“Alrightly then,” he said, laughing.
I had him get on his hands and knees on my little dorm bed. He barely fit, with his legs, even in that position, extending to the edge of the bed. I got behind him, and admired his black ass, while noticing his erect penis hanging down farther than I thought it would.
First, I toyed with his balls a bit. I may have squeezed a bit hard at one point, because he flinched. I apologized, but he said he was loving the attention.
Then it was time for the main attraction. First, with a dry index finger, I did to him what he had done to me. I just swirled my finger around his anus for a while. He was loving it, and making the appropriate noises, like “Mmm” and “Yes, Baby.”
I thought it was going to stink, but I found out the secretions at the edges of an asshole can smell very sweet and attractive. Who knew?
When I felt it was time, I coated my finger with some face cream and touched it to his anus. I then ever so slowly pushed in. Once my finger was all the way in, he asked me to add a second finger. It took a bit to work that in. I didn’t want to hurt him. Once I had done that, he wanted me to curl my fingers forward. He explained in the same way that women have G-spots, guys have what are called “A-spots.” He went on to explain that I could curl my fingers forward and massage his prostate gland, which felt very good to him.
So I did that, and he was obviously in heaven. I have no idea what that feels like to a guy, but it must be something good.
Unlike the other guys I had given handjobs to, James gets what he calls “pre-cum.” It’s a clear fluid that forms a drip on the tip of his cock. On this occasion, as I was massaging his prostate, my bed became wet with what seemed like a teaspoon full of it. It was also whitish, not quite like his usual pre-cum, but not like cum, either.
After a bit, I reached around with my other hand, and grabbed the obvious handle sticking out under him – his penis, and gave it couple of playful tugs. Suddenly, I felt something rhythmic happening around my fingers in his ass, sort of like pulsing contractions, and came to realize he was ejaculating. It left a big wet spot in my bed that I had to sleep in that night, but I was glad to do so.
By now I had learned a few things about sex. OK, I had learned things about what you might call sexual activity, but I was still a virgin.
Junie kept inquiring about my activities with James, and the guys before him. A couple of times before, I had told her in very generic terms what I had done, with the only detail being that I have particularly enjoyed giving handjobs. By saying that, I accidentally set off a chain reaction, that changed my whole life.
First, Junie started bugging me for details. I was at first reluctant to tell her the exact blow-by-blow events, but that’s what she wanted. Slowly, I started revealing more and more. She was so sincere, so curious, and so loveable in her own right, that I finally let the dam burst, and told her everything, like the anal fingering things. Her eyes were as big as saucers.
A couple of days after the ‘big reveal,’ she shyly asked me a question that knocked my socks off: Would I be willing to do that to her man Jason while she watches?”
After the briefest pause while I was trying to figure out why that might be a bad idea, trying to act nonchalant, I said, “Why, certainly. Glad to teach what I know.”
As I said it, I had a big realization: By claiming to teach, the whole naughty, bad-girl aspect falls away, and suddenly giving a guy a handjob is educational, not sexual. Hmmm… Interesting!
As soon as we could arrange it a couple days later, Junie, James, Jason, and I were all in our little dorm room. We had pushed the twin beds together to make a funky, but functional larger bed.
As Junie and I had planned, we decided to start with strip blackjack. We decided strip poker would take too long. Everyone was excited about the idea, but no one had remembered to bring a deck of cards. James disappeared down the hall for a minute, and came back with a borrowed deck. I think at that point, the combined heart rate of the four of us was over 500 beats per minute. I know I was excited, with my whole belly tingling, and my knees weak.
We started with me dealing. Jason lost the first hand, and took off his bow tie. James commented that it wasn’t fair. Jason seemed to have come over-dressed so he’d likely be the last one to go naked.
“Take off a couple of things sweetie,” Junie said to Jason.
He seemed reluctant, so we all started chanting, “Off, Off, Off.”
He removed his sweater and his shoes, keeping his socks on.
It was then decided among the four of us, that we had to even out the advantages. So a couple of people took shoes and belts off. Then we started in earnest, laughing all the way.
For some reason, I won practically every hand. On the other hand, Junie was losing every time, and I could tell she was trying desperately not to. Soon, her tits were out, and she had nothing left but her panties. I, on the other hand, had my T-shirt, bra, panties, sweat pants, and one sock. Jason and James were each down to their underpants and T-shirts.
I couldn’t help glancing at Junie’s breasts. She’s just a small Filipino girl, but she has some sizeable breasts. I guess I do too, but her’s were amazing, much better than mine. Unlike my areolae which were large and pinkish, her’s were tiny and dark. I noticed her nipples were looking pointy. I think she was excited. There was that lower-belly tingle and weak knees again. That was the first, but certainly not the last time that a girl affected me in that way.
Guess who lost the next round? Right, Junie! She was brave. Without much protest, she was stark naked in front of all of us. My roommate was beautiful, and I have never really noticed until I saw her naked. What a knockout! To what I can only imagine was everyone’s delight, she shaved her vagina smooth as a baby’s behind. And speaking of behinds, she was mostly facing me, but I could tell I liked what I saw of her behind already. Toned, small, beautiful!
We had to figure out what to do next. What if Junie lost the next hand? We decided that anyone who had already lost all their clothes would be the one to do some sort of sexual technique to the loser of the next hand. Weird, but functional. We also decided that no penetration was the order of the evening. I was still a virgin. I didn’t know about Junie, but we had all figured that penises shouldn’t be where they, well, shouldn’t be.
Junie didn’t lose the next hand. Jason did. And he lost again, and suddenly, he was reluctantly, but totally naked. His penis was surprisingly attractive for an ordinary guy. Furthermore, it was already erect, even before his underwear came off. In fact, I noticed that the fairly well defined 45-degree angle bulge in his underwear described his hard penis nicely. As he removed his underpants, my belly felt another twinge, and my heart did a little flip. He may have been ordinary, but like all penises, his was extraordinary.
The next one to lose everything was James. I was thinking, ‘Oh, oh, he might regard what happens next as ‘gay.'” Because, if we went according to plan, that would mean Jason has to do something to James.
I was surprised to see that James, too, was erect. He didn’t usually get erect right away with me. I usually had to work on him a bit. This evening was going nicely, I decided. Well, it might go OK, if James doesn’t get all weird about the arrangement.
As soon as we reminded the guys what the rules were, meaning that Jason would have to do something to James, I was expecting the worst. I was even imagining that the guys would get upset, wreck the mood, and we’d all put our clothes on and quit the game, quite unfulfilled.
That’s not the way it happened. James made some lame joke about it being “gay,” but he was smiling. Jason said something like, “When in Rome…” and it seemed they were totally fine with the situation. But what was the situation going to be exactly?
It took only a moment to find out. Jason knelt down next to James on the beds we had squished together, with Junie and I watching from the corners of the beds. The next thing you know, he’s sucking on James’ dick. I didn’t expect that, and swear to God I almost had an orgasm while watching.
James very much enjoyed it, leaning back and closing his eyes the way he does. After about a minute, he said, “Stop, I’m gonna cum.”
Jason backed away, and we played another hand. I lost my T-shirt. Then I lost the next hand and lost my bra. Jason inadvertently gasped. I guess he liked my breasts, alright.
On the next hand, it was James’ turn to do something, and the recipient was to be Junie. You’d think I might be jealous or something, but I wasn’t in the slightest. For me, this evening was better than a trip to Disneyland for a six-year-old. I could have been happy just being a fly on the wall watching everything.
He put his mouth on her right nipple, and I thought that he was just going to suck her tit, but he also reached down with his left hand, and started fooling around with her clit. In short order, he had worked two fingers into her vagina and was going to town on her G-spot, while still sucking her nipple. She arched her back, and screamed with a powerful orgasm.
The evening went on, with everyone getting everything. The guys were very good at not ejaculating too soon and spoiling the fun. They kept letting themselves get close to orgasm, without going over the edge. As it turns out, I wasn’t just a fly on the wall. Whereas I’ve always been satisfied with giving handjobs and not getting anything in return, I’m also happy to receive. And receive I did. It started with a most amazing French kiss from Junie. I was momentarily freaked out, but just fell into her arms and loved it within seconds. I recieved a good G-Spot fingering from Jason, and an ass fingering from James, which Jason and Junie watched closely, and were just delighted to learn about. There’s that learning notion again.
Lately, I had been thinking about this idea of teaching sexual things. Something seemed to be brewing in my mind.
The night wasn’t over yet. The boys had been holding out nicely, but I could sense it wouldn’t last much longer. Suddenly, Jason and Junie broke the rules. He stuck his penis in her beautiful cunt and was pounding her big-time. James and I just sat there for a moment watching. Even though I had already experienced three or four orgasms I was still as horny as ever. I’m sure James had his hormones running wild also. I mean, he had been close to orgasm several times, but hadn’t actually orgasmed. I can imagine what that would do to me, so he must have been going crazy.
“I’ve got a rubber,” he whispered in my ear.
I lost my ability to withhold, and was glad I did. “Go for it!”
He French kissed me like there was no tomorrow, then he broke away, dug in his pants on the floor for his wallet, took out a condom packet, tore it open, and expertly rolled it over his super-hard penis.
There was no doubt in my mind that I wanted this. The handsomest man in the world then hugged me close and whispered again, “Are you sure?”
I responded by pressing my pussy against his crotch. With me laying under this super-tall thin guy, he ever so carefully set the tip of his penis against me. Then, with the subtlest pressure, he was in. A couple of small wiggles, and he was all the way in. I was open – so open to him, I was stuffed full, and it was so right! I had thought the first time might hurt, but oh no, it was bliss! In a moment, he was breathing hard and funny. I could feel his muscles – his arms and upper legs jittering. And he came in me! I didn’t have an orgasm right then, but I didn’t need to. It was the most perfect thing in the world!
I continued to study psychology, but switched my interest from communication to sexology. I decided I’d like to be a sexual coach, and ended up with a masters in psychology. I then went into practice, and found that it’s not an easy field. There are too many sexologists, or psychologists who take on sexual issues, and not enough clients willing to even admit they have sexual problems.
I tried everything, even advertising on Craigslist. I did get a few clients, mostly women, sometimes couples who had real issues, such as no longer being attracted to each other, or erectile dysfunction. I was even able to help most of the time. But it wasn’t until I developed a specialty within the specialty that my business really started to grow.
Remembering one day how I like giving handjobs more than anything else, I put a little thing on Craigslist that I was giving intimate sexual instruction. Being a psychologist, I could get away with that.
Business started trickling in. Mostly guys this time. My ad wasn’t very clear, on purpose. When contacted, I would tell them that I was teaching how to have more overall confidence and self-awareness through learning about one’s own sexual self. Still not clear, right? That, too, was on-purpose. I wanted to build a situation in which I was basically telling guys that I would be giving them legal handjobs. And, by God, it worked!
Now, I did want it to be legitimate. I was convinced that one does become more self-confident, and in fact an overall winner in life, if one shamelessly masturbates frequently. I still believe that’s true. So, I was showing guys what I called “advanced masturbation” and, well, I was basically giving them handjobs, while telling them how important masturbation is, and then showing them some of the advanced techniques I’ve learned. Many of the guys started coming by for follow-up ‘lessons.’ Then the bolder ones among them told their friends, who came by, and so on.
One guy swore up and down that I cured his sore back. I was happy that he was happy, but I made it clear that I didn’t think I was the cause of his cure. He didn’t listen to me, and told people what ‘I had done for him.’
The next thing you know, more guys, and even occasional women, were coming by for my ‘laying on of hands.’
Stories started circulating that I fixed this guy’s diabetes, another guy’s eyesight improved, and yet another person’s blood pressure miraculously lowered.
I told each and every one of my clients that I was not the reason they were getting better. I’m sure it was a placebo effect. However, I could see how this placebo might be stronger than usual because there’s something about masturbation, orgasms, and all that, which do invigorate people, and invigoration goes a long way toward many maladies.
No one listened to me. Soon, my practice was full, even though I was charging huge amounts of money. I started holding workshops for ever larger groups of psychologists teaching them my techniques.
Last year, at the age of 28, I retired with enough money to live in style for the rest of my life.
I still enjoy giving handjobs, but just to my husband James, these days.