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Everyone Jerks Me Off

Another story from a client. I had a harder than usual time getting him to talk about this, but once he got started, he seemed to really enjoy telling me.

When I was 55, about 4 years ago, I had a checkup, and the doctor said I had BPE, benign prostate enlargement. I knew something was up, because my pee stream was not as strong as it once was. Evidently, this is common among men my age, and not really anything to worry about, as long as you monitor it, and/or take proper care of it. The doctor wanted me to start taking some sort of medicine. Since I don’t take medicine for anything else, I didn’t want to start, especially after he told me the possible side effects. So, I went home prescriptionless, and told my wife about it.

She did some research on the Internet and found that there are some natural things one can do. Get proper nutritional support, like vitamin E and pumpkin seeds, get regular prostate massages, and have plenty of orgasms. Hmmm, that last part sounded great!

My wife offered to help, of course. Starting that very day, she came up with a routine in which I’d lay naked on the bed, face up, with my legs spread fairly wide. She’d put on one of those blue rubber gloves that everyone uses for household chores and what-not, and slowly poke a lubed finger into my ass. She’d curl the finger upward, and massage against my prostate. I had no idea that could feel so great. If you don’t know, it kind of feels like you want to pee, but much better. With her other hand, she’d grab my rapidly hardening penis and start stroking. In just a couple of minutes, I’d shoot. Giving me a minute to recover, she’d then slowly pull her finger out of my ass, and that was that. She said she very much enjoyed doing it. When I came, she said she could feel my inner ass area pulsing against her finger, and she liked watching my face when I was orgasming. Interestingly, she has lost interest in sex during the past several years, and this was the only sexual activity we participated in at all. So, I was glad for the attention in whatever form it may cum.

We did this twice a day for several weeks. As you can imagine, like any frequent activity, it started to lose its greatness. It took me longer to get hard, and longer to cum. She started getting a bit bored with the process. But we trucked on for another month or so, duly doing the treatment twice a day.

I found out that she told her sister about the treatment. I was totally embarrassed, and not a little miffed at my wife for disclosing something so private. And later, I found out that the sister had told her husband. Geez!

One day, my wife announced she was going out of town for two days for a bowling tournament. She asked me whether I’d be able to take care of myself. I told her that I was an expert at jerking off. She asked, “What about the prostate massage?” I told her it would be fine if I missed a couple of days of it.

“No way, that’s not properly taking care of your health,” she responded.

“So what, exactly, am I supposed to do?” I was getting a bit agitated.

“I’ve got an idea.” Lenore (her sister) had already been informed, and she was planning to bring me a home-cooked dinner both days, and something more. She was going to give me the treatment!

“No fucking way!” – I believe that was my response, if I remember correctly. But secretly, I was instantly excited at the prospect, yet feeling very shy about it at the same time. Could that really happen?

Well, it did happen. The first evening when Lenore came over, she seemed a bit giddy, moreso than usual, which is saying a lot for her. She is a rather excitable, and exciting person. Whereas my wife has a calm demeanor, Lenore is the most flamboyant, outgoing woman I’ve ever met. She is also tall and, well, I guess I can say it, she is fat. Oh, not super-heavy, but compared to my skinny, perfect wife, her sister is rather a tanker. Her personality is nicely matched by her skinny, husband, who is the opposite, a quiet introvert. How they get along so well, I don’t understand, but they do.

So we nervously, excitedly ate the chicken dinner Lenore had brought, then she told me to hit the shower. I did. While I was in there, I was trying to figure out how to handle, even how to instigate what was to come next. I needn’t have worried. As I was about to step out, Lenore walked right into the bathroom like she owned the place. More than that, she reached into the shower, grabbed my hand, and gently guided me out, where she toweled me off, and then pushing lightly on my naked upper back, she walked me into the bedroom. She had me lay down just as my wife does, and put some KY on her forefinger. No glove! She just stuck that finger right in my butt. She did it a bit too fast, and it felt invasive, but nice in a way.

I was concerned about having an erection in front of her. Like it might not be appropriate. Go figure. Here is my rambunctious sister-in-law with a finger in my ass, and I’m worried that I shouldn’t have an erection! And so I didn’t. I wanted to, but I literally couldn’t. She spent several minutes massaging my prostate, and while it felt great, better than usual somehow, I stayed soft. She pulled her finger out, and went to the bathroom, presumably to wash off her finger. I figured it was over. I’d just have to jerk myself off later.

But, to my extreme joy, she returned and started fooling around with my cock. She had to coax an erection out of me. It didn’t take long. When it was obvious that she wanted me to ejaculate as much as I wanted it, my physiology accommodated fairly soon. What a remarkable experience to have an erection while getting a handjob form your sister-in-law of 18 years. I had never thought of her sexually, yet this experience was very, very sexual. And I came right away with a crashing, super-strong orgasm. She cheered, and seemed about as delighted as I was.

The next day, she showed up with her husband Mike. Oh well, no repeat of last night, I figured. Wrong! After dinner with Lenore and Mike, she commanded me to shower again. This time, I was met by both of them just outside the shower door. She led me to the bedroom, and guided Mike through the whole process. He was reluctant, and very shy. Not unexpected from him.

Before he stuck his finger in my ass (also without a glove), he kind of touched my scrotum a little bit. I’m not quite sure what he was doing. Maybe pulling it out of the way so he could actually see my asshole? But it had a very strange effect.

Now, I’m not gay, but I got an amazing, super-hard erection right away. The very minute he touched my scrotum, it was an uncontrollable, sudden rise. I was embarrassed! A minute later, he ever so lightly touched the tip of my penis. My cock kind of pulsed upward an inch, involuntarily, which brought a smile to Mike – and Lenore, who was watching intently, like a scientist looking at an insect through a magnifying glass.

As the process continued, and he slowly and gently pushed his finger into my ass, while slightly stroking my cock with his other hand, Lenore’s reaction was unusual: She was dead quiet, and just watching us with an almost hypnotic expression. I don’t need to tell you that I ejaculated immediately with his finger in my ass, and his fist wrapped around my cock. I shot all the way up to my chin, leaving a trail of sperm from belly button on up.

The next day, my wife returned, and had Mike and Lenore over for dinner. We all talked boldly and openly about what happened, and all agreed it was good and proper.

Next month, my wife is going on a month-long trip to Italy. I’m not much interested in travel. She calls me a ‘stick-in-the-mud,’ so she’s taking Lenore with her. So far, it has been discussed that Mike is going to offer the treatments. The four of us have figured out that Mike can’t handle all those treatments by himself. Of course we all realize that the treatments are unnecessary and/or there are other ways to do the therapy, but of course none of us would ever admit that. So we have been discussing who else to train for administering the treatments. We have lots of friends and relatives who with just a bit of training would be perfectly qualified.

Mike has also stated that he feels his prostate may be enlarging a bit, so he’s going to need some treatment also.

To my great surprise, my wife wondered what the treatment felt like, and so I had to administer it to her a few days ago. She actually orgasmed when my finger was in her ass. I was delighted, because it is the first sexual thing she has enjoyed in quite some time.

So far, Lenore hasn’t expressed any interest in any kind of reciprocation, but I’m sure we’ll all accommodate her needs, whatever they may be, when she lets us know what she’d like.

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Computer Guy and Horny Couple

So you know my business is housecalls for computer support. I can’t tell you how many times I’ve discovered porn on guys’ computers. And sometimes, oddly, the women, too. With the women, it is usually their own naked selfies, or maybe their husbands standing there, right in front of the camera with a hardon. With the guys, it is more like you’d expect: Commercial porn, mostly, you know, young girls with impossibly huge tits. Most of my clients act quite embarrased, or at least a little sheepish when I discover such things. The women seem to be actually more comfortable with me seeing them – their actual naked selves on the screen, than the men do when I see their stupid commercial porn. I don’t know half the time whether the stuff is there intentionally for me to discover, or if these people are really embarrassed.

Anyway, one day I came to a fairly nice home and was greeted by an athletic-looking husband and wife team. They seemed especially close. You know, with most couples in their homes, at least when I’m around, they seem to be in separate rooms, and don’t talk all that much with each other, unless they are both telling me a story or something. And then, it’s generally something about their kids.

Anyway, I get there, finding, as I expected, that they had malware. I plugged in my flash drive, and started the anti-malware software. It takes ten minutes to run, and so during this step, I usually make small talk with my clients. I noticed that their desktop image was a tasteful nude shot of her.

I didn’t have to work very hard at small talk this time. They were standing before me, to the side of the desk, she with her arms wrapped around her guy, and she started right in with some really weird stuff. First, she wanted to know whether I had recognized the picture on the screen behind all the icons, as her. I said I did.

Then she got more involved, like about how bisexuality is a good thing. I had to agree, but I did so very cautiously. I kind of figured where this was going, and even thought it has always been a dream of mine to have something happen with a client, this was potentially too good to be true.

He started talking about wanking, and, well, male sexuality. Interesting. He admitted that he likes her blowjobs very much.

OK, I took the bait. I answered that I love a good blowjob too, but haven’t had anything like that in a very long time.

I’ll bet you can imagine what happened next. Right! He came right out and offered his wife’s services. I accepted.

The computer was abandoned, and we went into their bedroom. They have a very nice, inviting king bed. But, at this point, I kind of stalled. I’m not quite sure why. I guess maybe because it is just too strange to pull down one’s pants in front of people you’ve just met. No worries, he was out of his clothes in a heartbeat. And his shlong was already hard and pointing out at a 90 degree angle. Shaved, I noted, with a shiver of delight. As I was sorting that out, she stepped out of her robe. I hadnt’t noticed that until now. She had been wearing a simple bathrobe and nothing else! Why hadn’t I noticed that? It was pretty obvious in retrospect. Now, she had nothing. And she was beautiful. Next to her rather skinny, 6-foot-something husband, her small Asian body was a miracle to behold!

Well, I won’t bore you with the details. In short order, she did give me a blowjob. The husband suggested that I not cum just yet, as there was more that could happen. Then he blew me far a while. While he was doing that, she kind of pushed my legs up over my head, and started swirling her fingertip around my anus. Unfortunately, I came right away. They cheered. Then the two of them started in on 69 while I recovered. I’d like to say I made a full recovery and was able to cum again, but no, that, unfortunately, was it for me. In time, I returned to the den and finished the computer. I said my goodbyes, and they told me they would really, really like to have me return soon! It wasn’t said explicitly, but I believe they were insinuating that they’d like to be even more intimate. Problem is, it’s been more than a month, and they haven’t called me, and even though sometimes I’m super horny and know how nice the evening could be, for some reason I haven’t called them. Oh well, soon!

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Best Fake Female Ever

This is for guys who think they want to be with a real lady. Maybe this will be OK to. Maybe better!

Buy a small watermelon. That’s your only expense. So, this will cost far less than taking a real lady on a date.

Leave the watermelon out in the sun until she is nice and warm.

Carve a hole in the watermelon just a little bit smaller than you-know-what. I’m talking about your dick, Stupid. Make a hole that will be just a slightly tight fit for your erect penis.

Put the watermelon in your bed. Surround her with some sheets so she won’t tip or roll around. Just like you wouldn’t (usually) hold a lady in front of you during intercourse, you don’t hold the watermelon. You lay on top of her.

Now, go to work and fuck the bejeepers out of her.

A little of the red fluid may leak out. That’s nothing. She’s just at the end of her period.

This woman won’t get pregnant, so there’s no need to hold back. I think you’ll also enjoy that you can do everything your way, when and where you want, without compromise. She won’t disagree with you about anything.

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You Want the Car Keys?

Another story from a client.

I knew he planned to go out playing poker with his buddies again. I’m a lonely woman on Friday evenings when he does that. He comes home late, and just falls asleep. I hate that. So, one Friday, I invented a little game that changed everything.

I prepared before he came home from work. I should explain, we each have a bicycle which is our primary mode of transportation, by choice. But we do have one car between us for when we need to transport stuff or longer trips.

So, he wanted the car keys.

“Where are they?” he asked, looking in the little tray on the hall table, but finding it empty.

“Hot or cold,” I teased, letting him know I wanted to play a little game.

It took him a while, but he kept getting hotter as he guessed places closer to my body.

When he finally understood, his face actually flushed red a bit, and he meekly said, “Really?”

“Yup, and you have to get them. I’m not going to just hand them over.”

“OK, you little beauty, you asked for it!”

And with that, he carried me into the bedroom, and practically tore my clothes off. I made sure he was textile-free as well.

We pretended to wrestle, although if he had really wanted to, he could have thrown me down on the bed in one second flat.

He didn’t need any lube. He unceremoniously stuck his fingers in and got the car keys.

Normally, I orgasm fairly quickly, but this was ridiculous. As I felt his fingers wiggling around, and then the scrachy things being removed, I came instantly, and it was a strong, crashing orgasm.

Once the keys were removed, they were forgotten. He stayed home. We played, we showered, we dined, we watched a movie, we talked late into the night.

For some reason, he doesn’t go to those poker games any more.

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Answer to a Crappy Mood

Another story from a client.

My wife is great, don’t get me wrong. But sometimes, she gets in a crappy mood. Don’t we all?

Our arrangement is that I bring in all the money, and she takes care of all the domestic chores. I’m a psychologist. Sometimes, I’ll get a client who is very problematic, and sure, I might complain too.

However, on this particular occasion, it was she who was complaining. It was laundry day, and she hates doing the laundry.

We live in a naked household. I guess you’d call me, Connie, and the kids nudists, but only in our own home.

So there she was standing in the middle of our bedroom holding a laundry basket, feeling frustrated, and I wanted to help.

I suppose I could have volunteered to do the laundry, but not really, I had my first client of the day in a half-hour. So what could I do to help Connie?

While I was thinking about it, I coated an index finger in spit, and pushed it against her anus. She changed her stance to spread her ass cheeks, making it easier for me. I didn’t have any plan as to where this was headed, I just knew that she loves anal fingering. I just didn’t know whether she’d like it in her current mood and while standing there holding the laundry.

Her change of stance, granting me access, said it all. I started to become erect, but ignored it. Instead, thinking quickly, I said, “Let’s go.”

She started walking, and I walked right along with her so I could keep my finger in position. We walked that way past the kids’ rooms – they were still sleeping – down the stairs, where I had a little trouble keeping my finger in position, and all the way to the basement.

Connie separated the whites and colors and some delicate things, put a load in the washer, added the soap, and turned the machine on, all with me standing next to her with my finger still in her butt.

As the machine started filling with water, I had her turn toward me while I knelt on the floor. So now, she was facing me, with my arm curved around her butt, and the finger still in her anus. My tongue was right in line with her clit. I did exactly what you would expect. I licked her to orgasm with my finger still in place. I felt her orgasmic contractions, her anus was squeezing my finger. I also felt her knees buckling slightly. I had to kind of get sideways to bend lower to keep licking until her orgasm was finished.

Connie’s a one-orgasm woman. Some can have continuous orgasms. Not Connie. Like a man, when she cums, she’s done.

I pulled my finger out and bid her ‘good-bye’ as I went back up the stairs to get dressed and greet my first client.

She seemed happier for the rest of the day.

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An Hour Before Work

Another story from a client.

My wife grabbed a large feather…

It was an hour before I needed to leave for work. I usually noodle around on the computer at that time, but my wife invited me back into our bed for what we call ‘touching.’

She’s no longer sexual. She says her hormones have changed. I’m OK with that, because she really seems to enjoy ‘touching’ me. Believe it or not, I like her handjobs even more than I liked fucking in the old days. I really do!

This happens every few days, generally in the evenings after work, weekend afternoons, but sometimes in the mornings.

What she did yesterday: She started with the feather. That part was new. She usually just uses her hands. She ever so lightly touched it all over the underside of my flaccid penis as it laid against my belly. She also rubbed it ever so gently over my scrotum. Within a minute, my penis was as hard as stone, and lifting off my belly at a 15-degree angle.

Sometimes I worry that I won’t get hard. At my age and experience, having had many bisexual encounters, sometimes someone can spend quite a bit of time with me before I become fully erect. That kind of bothers me. It’s sort of embarrassing, plus I like whoever is doing that to feel they are succeeding.

The truth is I enjoy the sensations very much, even if still soft, but, I’m somehow thinking it isn’t ‘manly’ or something to stay soft. And, of course worrying about it, or wishing it to happen, keeps me softer longer. Figures, doesn’t it?

Well, I hardened up yesterday just fine, with the feather and all. After a while, she put it down, and started gently massaging my balls. I like that. I like the actual physical feeling of them squishing around in my scrotum under her fingertips. But I also like the vulnerability. She could squeeze really hard and hurt me at any moment, but I know she’d never do that. She’d be horrified at the thought.

She massaged my penis the same way, and after a while she started stroking me up and down. When that starts happening, my concern changes. I’m no longer concerned about being hard, because now I’m very hard. Now, I’m concerned about cumming too soon. But that always happens. The feeling starts to build. I try thinking about computer science or something, but the feeling continues, and then, there it is, I ejaculate on my stomach.

Now, my final concern: I’d like to have ejaculated a whole lot, like ounces of cum. But generally, only a rather small few squirts come out, totaling less than a teaspoonful. She hands me a paper towel, and runs off to the bathroom to wash her hands. I thank her and put on my pants and head off to work, a very happy man.

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They Ran My Teacher Out of Town

Another story from a client.

The year was 1986. I was a high school girl in a small town in Oregon. The school was correspondingly small. For instance our two gym teachers, a man and a woman, were also our History and Math teachers. We had coed gym classes, but of course separate showers and locker rooms.

It fell on our gym teachers to teach sex ed, which became required just that year. It was my senior year. Frankly, by then, it was already too late. Most of us kids learned about sex by then, some even with actual experience, if you know what I mean.

So one afternoon, we arrived for a gym class, after the usual changing into T-shirts and shorts. Mrs. Forester had us all sit in a semi-circle on the floor for some sort of lecture. The 30 boys and girls in the class were all looking at each other like, “What, no exercise?”

Then Mrs. Forester launched into a lecture on sex. Mr. Johnstone, the other teacher, sat on the floor along with us, looking like he really didn’t want to be there. He stayed quiet as a mouse the whole time. The kids were all tittering and she had to shush us several times so she could go on. The poor woman was red in the face, talking about condoms and such, but I had to give her credit for frank, and dare I say, naughty, straight-forward information.

She then announced that since the sex ed was brand new to the school, they had not yet received any materials. I believe she meant charts, pictures, maybe instructional videos. So she called for two volunteers. I had no idea what she wanted, but I’m kind of crazy in that I’ll volunteer for just about anything. I always believe new experiences are good for me, and that by volunteering, I’ll have the best opportunity to experience new things, compared to just watching. The other volunteer was Jay Cranston, a tall, cool guy that loved baseball. I often fantasized about Jay. I won’t tell you exactly what I fantasized about him. Let’s just say it was X-rated.

I figured the teacher would have us stand next to each other and point out that boys are generally taller, maybe show that girls have the second layer of fat that makes us a bit rounder, and so on.

She did have Jay and I stand up next to each other. Then she matter-of-factly asked us to remove our T-shirts. Of course he was OK with that, but whoa, what about me?! Glancing at me like ‘Is this for real’ he did remove his T-shirt, so after a moment, I did too, revealing my white bra. Mrs. Forester said, “bra too” as if this was an everyday request.

Naturally, I hesitated. Mrs. Forester explained that the point was to show the boys, and perhaps the girls too, about the sexual organs. She then added, “But Judy, you don’t have to. We probably have someone else who will volunteer.”

As I said, our school is small, and everyone knows everyone else. To this day I can’t explain why, but I didn’t want anyone else to have to do it instead of me. Was I protecting the other girls? Did I have an exhibitionist streak? Was I proud of my rather large breasts which were still rather new to me?

Plus, it wasn’t like she was asking me to pull down my shorts or something. It was only my tits. I have always felt that it is unfair that boys don’t have to wear shirts, but us girls do. What’s wrong with people seeing breasts? Everyone has them, even though the breasts and nipples on boys are much smaller. My thinking was totally intellectual. I’d never actually do anything about it. But geez, this was really weird. I continued to hesitate. I’m pretty sure I was blushing in front of everyone.

Mrs. Foresteter interrupted my hundred-mile-per-hour thought processes by repeating that I didn’t have to do it. She’d get someone else.

So I did it. In front of every kid in the class, and even Mr. Johnstone, I twisted my bra around, released the clasps, and there I stood, topless. At that moment, I couldn’t believe I had done it, and wanted to run out of the room. The fact is, I probably couldn’t have. I was feeling feverish and woobly, basically scared to death.

Mrs. Forester didn’t miss a beat. “You’ll notice, class, that Judy’s nipples are larger in diameter than Jay’s. What you may not know, is that although Judy’s nipples are sensitive to a very light touch, a good practice in foreplay, so are Jay’s. Yes, women can excite men’s nipples as one of the many techniques in sexual foreplay.

While she was doing this, she was using a yardstick as a pointer, and kept lighly poking the side of my right breast, and then my nipple. I should have found that terribly objectionable, but instead, I found it electrifying.

Sandra Berkley raised her hand and asked, “Can you tell some other techniques in foreplay?”

“I will,” the teacher answered, “but that will be next Tuesday. Today, we’re just going to introduce the comparative anatomy.”

Suddenly, I panicked. ‘Comparative anatomy?’ Surely Mrs. Forester wasn’t going to have me and Jay show everything. Surely not! Right?

She did! As Mrs. Forester requested it, I felt even more scared than I had been already. Really scared. I mean all jittery and with weak shaky knees. Why? I have no idea. Worse, I felt like I might not be able to keep my pee inside me. I don’t know what was happening with Jay. I couldn’t even look at him. I couldn’t look at anyone. I’m sure my gaze was fixed on the floor.

Suddenly, the class went crazy. First a dead hush, then a whole bunch of murmering. Everyone was looking at Jay. The fool had removed everything but his socks. Standing not six feet away from me was a totally naked 18-year-old boy. I later came to find out that Jay is quite an exhibitionist. He actually likes being seen in his entirety, and will show off at any opportunity.

Somehow, it made me feel better. I mean, even though he’s a boy, I felt something kindred with him, and when Mrs. Forester asked me for the second time to take off my skirt and underpants, I just did it. Like ripping off a bandage. A big, important bandage!

So there I stood, stark naked, with a naked boy right next to me. I can’t tell you how many emotions I felt at once. Fear for sure. Naughtiness, as if I had done something terribly wrong and was going to be punished any moment, even though it was Mrs. Forester who had commanded it. But something else, too. I felt an odd sense of pride. I feel my breasts are, well, let’s say prominent. I had actually had masturbatory fantasies of people, including some of my classmates seeing them. Now, it was happening for real, and they were seeing the rest of me too. Oh, not the way I dreamed of, but, well, geez!

Now, Mrs. Forester broke through all boundaries with her next request – as if things weren’t crazy enough already. She wanted me and Jay to turn around, bend over, and show everyone our anuses. Really! Even crazier than that, I wanted to do it. I can’t tell you why. I just did.

So, I complied. Jay also turned around and showed his anus. He balked, but then he did too. So there we were, side by side, bent over, and holding our ass cheeks apart so the whole class could see our buttholes. I glanced over, and momentarily marveled at how this big boy had such a skinny little ass.

Mrs. Forester poked me lightly in the right buttock with her yardstick. Then the unthinkable happened. She touched the end of the stick right against my anus. You know what? It felt like a surprisingly wonderful electric shock. I wanted her to do it again, but no such luck. She was saying something about how boys’ and girls’ anuses are nearly identical in appearance, function, and the response of the nerve endings.

She had us turn back around and face the class – and Mr. Johnstone. I’m sure I blushed when I noticed him staring right at me.

My thoughts went briefly to Jay, and he was really red in the face. He looked like he was about to run out of the room. You want to know why? His penis, the first one I had ever seen in person, was erect. It was sticking up at a 45-degree angle.

Mrs. Forester just kept right on talking and poking us occasionally with her stick. As she was explaining something I don’t quite remember about erections – my mind was a mess at this point – she pushed the stick lightly against Jay’s penis, pressing it fully vertically against his belly.

Guess what happened to me? Seeing that, I orgasmed. I don’t think anyone noticed, and fortunately, I wasn’t wet enough to start dripping. I was so fucked up, I mean wobbly legs and all, that I had to sit down on the floor.

But the weirdness wasn’t over yet. Now, Mrs. Forester asked me to show the class the inside of my vagina. And I complied! Without thinking it through, using my fingertips, I opened up my lips, and let everyone have a good hard look. I noticed Mr. Johnstone was staring as hard as anyone. He almost looked like he was drooling.

Suddenly, it was over. We were commanded to dress, the bell rang, and the class was over.

We were to have another sex education session on Tuesday. I could only imagine what Mrs. Forester had planned.

As Tuesday approached, I couldn’t hardly think or sleep. Every waking moment was filled with ‘What’s going to happen next?’ Would I be volunteering again? I really didn’t want to go through anything like that again, and at the same time, I really, really hoped she would pick me.

Finally, finally, it was Tuesday afternoon, and time for gym. The thirty of us were surprised to find that Mrs. Forester was not there. Neither was Mr. Johnstone. Instead, the principal, Mr. Henrickson, led the class. It was super disappointing. Basically, he said it’s OK to masturbate, explained the birds and bees as if we had never heard that a thousand times before, and that was that.

The school board, consisting of my mother and two other members of the community held an inquiry. Jay and I were the witnesses. We both told what happened, but as minimally as possible. You see, we liked Mrs. Forester, and wanted to protect her. It did no good, they fired her. And, they fired Mr. Johnstone too. Why him also? I think they felt he could have stopped it, but didn’t make any effort to do so.

So that’s it, they ran our teachers out of town.

Jay and I got together a few times. We enjoyed talking about what happened. Together we decided we weren’t traumatized, although we weren’t entirely sure about that. He and I did get naked together one more time. This time it was in private, in the treehouse in his parent’s back yard. We kissed, and kissed, then we wanted to have sex. But neither of us had a condom. It turned out weirdly, we kind of briefly gave each other oral sex. He didn’t orgasm. I didn’t orgasm, then we went our separate ways.

I liked him, he liked me, but somehow, nothing ever became of us. We went to separate colleges. We have kept in touch, maybe emailing each other once or twice a year. He became a farm-league baseball coach, and I work at the very same school as the History, Geography, and Economics teacher. I can tell you that sex education in that school these days is very profunctory, basic, and nothing like that day back in 1986.

2024 Update: Jay wasn’t making enough money as a baseball coach. He moved back to Oregon, and since he had a degree in education, took a job in our school. He teaches the sciences and, you guessed it, gym class.

Last year, my husband and I amicably divorced. We just weren’t that into each other any more. Jay and I became an item, and yes, we do fuck like rabbits, often reminiscing about our sex ed class in 1986.

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Gay Man’s First Encounter With A Woman

I made it to 34 years old without ever being sexual with a woman. I’m gay. I knew that from my early teens. I loved seeing workmen in bluejeans. Bearded was better. I like thin, tall guys. I’m a tall, thin guy. I don’t have a regular boyfriend. I just have all kinds of sex with guys when the situations come up. No strings attached.

Women are almost non-existent in my mind. They’re just there, like furniture.

Except one woman. She drives a truck for the same company I do. Every now and then, we have two drivers in one truck, usually when there’s a lot of unloading to do. We had a two-day trip through the mountains, involving twenty stops. They figured two drivers was best, and I got paired with Judy.

She’s of Japanese descent, and I actually noticed her. She is attractive. Even though she is small, she is strong and very good at unloading. I know the hetero guys just lose it in her presence. I think she is tired of their juvenile behavior around her. I think she respects me because I act normal around her. I mean, she is only slightly attractive to me. I’m gay, after all.

So, as evening approached, we pulled into a Motel 6. The company reimburses expenses on the road, but just barely. For instance, they’ll pay for one room for two drivers. I figured Judy and I would split the cost of a second room. But no, we discussed it, and decided we were adult enough to share a room. They always have two beds, so no problem.

So we got in there, Judy turned up the thermostat while I took a shower. Then it was her turn, and to my surprise, she took off all her clothes in front of me before stepping into the bathroom. I was a bit appalled to see how naked she was. Women aren’t as hairy as men, and it looks weird. Her breasts were probably average size, but they sickened me a bit. Her vaginal area was covered in black hair, so I couldn’t see anything clearly. But still, that nicely rounded small butt, and her Asian looks were somehow attractive.

While she was in the shower, I started masturbating under the covers. I guess I was actually thinking about her. Why, I don’t know. I was really starting to get into it, getting near orgasm, when she popped out of the bathroom more suddenly than I had expected. She noticed the movement under the sheets.

“Are you jerking off?”

“Well, yeah.”

“Is it because of me?”

“No…. no! – well, yes, I guess so.”

She smiled, and dropped her towel. She climbed into the bed with me. She put her hands on my shoulders, and then sort of started rubbing my neck. Then she kissed me. I lingered, and stayed with it, but didn’t really care for it. But, I didn’t want to hurt her feelings, so I let her kiss me a bit longer.

My penis stayed hard. She noticed, threw the covers off, and wrapped her fingers around it. That felt nice. She stroked it a bit, and I started to feel a bit orgasmic. She stopped suddenly, and asked whether I had a rubber. I did. I rumpled around in my pants on the floor, found it in my wallet, and opened the packet. She expertly fitted it around my hard penis. She then gently pushed me back against the bed so I was laying face up, and climbed on top. It was obvious that she was going to sit on me, and have me enter her mysterious pussy.

I wilted to about half-erect right away. She tried this way and that to get my penis in her, but it wasn’t happening. The more she tried, the softer I got.

“You’re afraid, aren’t you?” she asked.

“Something like that.”

I didn’t want to tell it was more like a mild revulsion. She then climbed off me, and started giving me a tour of her body. That was interesting. She showed me her large nipples in detail, and said she likes having them sucked. She turned around, spread her ass cheeks and showed me her asshole. I liked that. I could easily have gotten hard again (I think) if she had invited me to put it in her anus. But she didn’t. Instead, she continued the tour, showing me her clit, and pulled open her vagina a bit so I could look deep inside. To me, I have to admit, it looked more like an injury between her legs than something sexually inviting.

Have you ever watched a drunk at a party throw up? You know how it makes you feel nauseous too? That’s what I felt when I saw that, and my penis lost any remaining erection it might have had. With the tour over, she suggested we lay side by side and masturbate ourselves. And that’s what we did.

I enjoyed the adventure, and I enjoyed her company. She laid right next to me, with our shoulders touching, and she rubbed herself to an orgasm within a few minutes. Almost as if I wasn’t there, although she later told me that by me being next to her, it made her very, very horny. While she was doing that, I rubbed my penis, and it eventually became hard, and I finally ejaculated. That was it.

She climbed into the other bed, and after an hour of television, we went to sleep. I like Judy, and we have driven together a couple more times, but a situation in which we need to share a room has not come up again. I don’t know what will happen if it does. I’d kind of like a do-over. I think I could get hard and fuck her. I’d like to try and see what it’s like. My buddies tell me it is like butt-fucking, but looser, and that in some cases, you can feel the girls grip you with their inner muscles when they orgasm. I’d like to at least experience that, but don’t know if I could actually manage to get hard, or not. Maybe, we’d just masturbate side by side again. In retrospect, that was fun.

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Anal Acuity Among Coworkers

Here’s another story told to me by a friend. I actually recorded his whole story on my iPhone and have transcribed it for you here. I edited it a bit here and there so it would make sense to you, since you haven’t met my friend, but as to the details, it is 100% accurate. My friend is 24 years old, white, average height, a touch pudgy, has no suntan at all, long musician’s dark brown hair, and a ruffly beard. Here you go:

I own a small musical instrument store and have two employees. When there are no customers in the store, the conversation can get quite, well, explicit. I think all three of us have been somewhat attracted to each other, or at least we are very good friends, and we do communicate well.

The other two are Amanda, age 24, and Jerome, 22. One day, as had happened a few times before, our discussion turned to masturbation. But this time…

I admitted that I like anal stimulation. Jerome, said he likes it too, and has a pretty good sense of touch there. Amanda asked what he means by that. He said that he figured if someone had an assortment of items, such as a wooden spoon, hairbrush, paintbrush, and other instruments with various handles, he could tell which is which by the feel of it in his anus.

I didn’t think that would be likely. Both Amanda and Jerome thought so, and the next thing you know, a challenge was on. Initially, Amanda and I decided we were going to test Jerome’s ‘ability’ but he wasn’t ready for us to see his ass. He was understandably embarrassed.

To my remarkable surprise, Amanda said, “Hey, we’re all friends here, let’s all do it.”

I was shocked, surprised, delighted, and a little scared all at the same time. First of all, I would just love to see Amanda naked, and Jerome too, for that matter.

Amanda is all Irish, with red hair, freckles, a fairly tall build, and large breasts.

Jerome is the classic black guy. Very dark skin, short curly hair, a wide nose, and a large body. He is probably like 6′ 2″ tall, and built strong, without an ounce of fat. For the longest time, I have wanted to see his dick.

I’m one of those white guys who believes that many black men have bigger cocks. I know intellectually that that’s just an urban legend, but still, I was expecting something large from Jerome. I was thinking if we actually went through with this, we’d just pull our pants down a bit, bend over, and wouldn’t really get to see that much. On the other hand, just seeing my friends’ assholes would be an extraordinary turn on.

After considerable balking, embarrassed laughter, and so on, we went over to my apartment, gathered our equipment, which included just about everything with a handle in my kitchen, and the headpieces of a few woodwind instruments, drumsticks, and other gadgets from the store. We figured out some rudimentary rules to our game, and we began.

I won’t bore you with the details of how we became entirely naked. I’ll just say that I turned up the heat so everyone felt uncomfortable in their clothes, and we played strip poker until we were all brilliantly naked in front of each other.

Both Jerome and I had huge erections right from before our clothes came off. I was the first to lose my underwear, and was sort of concerned for my two best friends and fellow workers to see my wood, but at the same time very, very excited. Precum was drooling out the tip of my tool, and that’s unusual for me.

Jerome’s cock was indeed huge, and I commented on that. But it wasn’t really. He pointed out that it was an illusion because black objects generally look larger than white ones. Plus he was uncircumcized, while I was cut.

We found a measuring tape, and it turns out, he was 1/4-inch (6mm) longer than me. So then of course Amanda had to know about girth. She wrapped the tape around my dick and then Jerome’s, and found I was 2 mm larger in diameter. It really didn’t look that way.

By the way, it was the most exquisite thing in the world when she casually grabbed my dick to wrap the tape around it. My dick jumped involuntarily at her touch, and if she had simply held it for another minute, I probably would have spurted cum right then and there. From the looks of things, that was the case with Jerome as well.

So, back to the competition. The idea is that one person would be on hands and knees with his or her head buried in a pillow on my bed, while the other two took turns gently putting things in the person’s anus. We used some coconut oil I had in the kitchen as lubricant, and we’d slowly push the item in a couple of inches and then stroke it in and out a few times, plus twist it from side to side. Then the person had to guess which item it was.

It turns out we were all about equal in our ability to identify objects. For instance, the flute headjoint was easy, because it was cold, and had a protrusion on one side. The wooden spoon’s rough handle was easy to identify. The back of the whisk was very similar to the hair brush, and so everyone mixed those two up – and so on.

We played this game longer than we needed, because there was some ice to be broken, and we didn’t really quite know how to take it to the next step.

It was Amanda to the rescue. She just came right out and asked Jerome whether he’d like a handjob.

“Hell yes!” was his answer.

He laid on his back on the bed, and she went to work.

For a few minutes, I felt something unexpected. I felt left out. Kind of slighted in a way. But as Jerome was getting close to cumming, she stopped, and told me it was my turn. She gave me a gentle handjob that slowly became less and less gentle. She also fondled my balls lightly with her other hand, which I instantly discovered was one of the seven wonders of the tactile world. I started to buck and moan, and she stopped. Dang! I was so close. That must have been the way it was for Jerome, too, just a few minutes ago.

So then Jerome and I went to work on Amanda. I sucked and fondled the nipples on her wonderful freckled breasts, while he massaged her lower body, finally settling on very gentle stimulation of her inner labia and clit.

With her large breasts, you’d expect large nipples, but no, she had little tiny pink things. Of course that didn’t bother me a bit. In fact, it was all the more of a turn-on. Well, we spent the rest of the afternoon trading off.

Amanda came several times, leaving wet spots on the sheet.

Jerome and I decided we’d try to hold out as long as we could, but eventually, both of us went over the edge in Amanda’s hands or each other’s hands and ejaculated quite nicely. That pretty much ended the afternoon. Jerome came first when Amanda was absent-mindedly stroking him, and forgot to notice his physiology as he was getting closer and closer to the brink. So over the top he went.

Fortunately, Jerome is one of those guys who doesn’t melt into a puddle after orgasm. He reached over, and massaged my balls quite nicely before finishing me off with an amazing handjob. We both turned to Amanda, but she was already satisfied.

We’ve discussed it, and all three have decided that it was a great afternoon. We wondered if there was anything wrong with what we did, and unanimously concluded, that no, everything was perfect and correct.

Since that afternoon about a month ago, we’ve been better friends than ever as we work in our little music store. I’ve been less like a boss, and more like a co-worker, which they have commented positively on. But I’ve always been a good boss, at least in my opinion.

We’re planning to get together again next Friday. We’re going to play extended strip poker. The way it will work is that after someone has lost all their clothing, when that person loses again, he or she will have to do something – anything of that person’s choice, of a masturbatory nature for sixty seconds. I’m already busy thinking up things I can do in my sixty-second intervals. I hope I lose a lot!

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About the Picture on the Internet

You know about my crazy mother. She’s the cause of the picture on the internet. I was telling you about the one gay relationship I had. His name is Gary. Mom invited Gary and I to the nude beach, and he was all up for it, as was I, even though we just thought it would be a fun time on the beach in which we’d happen to be clothes free, nothing more. I should have known that with my mother, it’s never as simple as that.

So we get there, and it’s a warm but breezy day. We get our clothes off. Gary can’t stop complimenting my mom on how she looks. I have to admit, she is a hot chick. She started her usual talking all sexy bit. She wanted to know how big Gary was when erect. She finally talked him into showing her, right there on the beach in front of everyone. You have to know, it isn’t that kind of nude beach!

He started to wank himself to become erect. My mother, in the meantime, is lightly running a finger over one of her nipples, and moving her other hand around on her shaved pussy. Gary being erect, and my mom doing that was too much for me, and I became erect also.

There were like twenty people watching us at this point, some discretely from a distance, but about six came right up close, watching, smiling. One guy held up a phone and asked if he could take our picture. I was about to say “No way!” but Mom shushed me with a look, and said “Of course.” I felt like I was in a trap.

Mom instructed us to stand up, one guy on each side of her. She put one hand around each hard penis, and said “Smile.”

We smiled, and in that moment, history was made. Mom asked the guy to email her the photo.

The next thing I know, it’s on Mom posted it on her account. Me! Standing there next to Mom and Gary, with an erection, and my mother holding my dick. Now, I like porn as much the next guy, and browsing the web, I’ve stumbled across that picture a half-dozen times. Evidently it’s gone slightly viral. Every time it practically gives me a heart attack. I mean, I feel a shot of adrenaline every time I come across myself with a boner on my computer, just knowing that thousands of people have seen me like that.

I don’t know what to think. It scares me that anyone can see me all nude and erect. It also makes me proud. I’m not a half-bad looking guy, and that picture is rather bold. I mean, I’m there with my erection, and all is well with the world in that photo. I’m kind of OK with that.

But some day, one of my coworkers, someone from church, or someone I know is going to say, “Hey, I saw you on the Internet.” How am I going to feel, how am I going to react when that happens?