by Jenelle Watson
Since around the time I turned eighteen, I’ve been crazy about two things: Pickleball and sex. I had quite a bit more experience with one than the other.
My best friend since grammar school is Cindy Montrose. She and I were introduced to pickleball in the fourth grade. We didn’t think much of it at the time. It was just another sport.
A couple of years later, I got the hots for a boy, Rudy Cordoza, who played pickleball every afternoon. He had no idea how attractive I found his tall, dark looks, and being fourteen years old, I didn’t say anything. I didn’t know how to approach him romantically. I just started playing pickleball so I could get close to him. Cindy only started playing because she and I were best friends.
My plan didn’t work because I could never get on his court. Rudy and his friends were all much better players, and they had no tolerance for people like me. I was always two or three courts away with the weaker players, admiring him from a distance.
While I was trying to get next to him, I played so much pickleball, that I accidentally started to enjoy the game. I became good at it. By the time I was sixteen, I was playing on his court, the expert court, although by then he had moved on to other sports. Along with Cindy, I won regional championships. With a couple of guys, I won mixed doubles. The guys and I didn’t hit it off except as pickleball players. They seemed immature, or maybe they thought I was. The sport was fun, though.
Nothing ever happened with Rudy. Four years later, I wondered why I had ever found him so attractive.
It’s when I turned eighteen that my world started shifting. Cindy and I became so good that our potential mixed double partners were intimidated by us, so that limited the group we got to play with.
There was this one guy, with the old-fashioned name of Albert Weissman, who was a pretty good player, but way too full of himself.
It didn’t help that Al was good-looking. I’ll have to admit, very good looking. He’s tall, blond, thin but strong, with a noticeably square jaw, a dimple, and sparkling eyes. And he knew he was good-looking, which was part of his problem.
I would have liked playing with him, but he always had advice that drove me crazy. Things like, “play forward,” when it was better to hang back, or “backspin, backspin!” when a topspin drive would have been a better choice. So, I’d do what’s right, hang back, or use topspin, win the rally, and he’d be fuming because I didn’t listen to him.
He also thought he was so hot stuff because he’d tell me in a quiet voice where he was putting the serve half the time. Like, “Right front corner.” Then, he’d serve it there, forcing the opposing player to come forward, often putting me in a smash war rather than a nice dinking rally.
The problem is that he was a good player. So, when I ended up playing with him, I’d just grit my teeth, and hope he didn’t have too much of his useless advice. It got so bad that when I’d see him approaching on the pickleball court, I’d feel my stomach falling out.
Oddly, sometimes when I’d masturbate, his stupid face would appear, and thinking about him would make me orgasm. Go figure!
Cindy was not only a great player, but my best friend, too. She’s a real knock-out with flowing but slightly wavy strawberry blond hair, big boobs, and a tall, modelesque build. In fact, she did model for a local tourist magazine one time. It was fun seeing my best friend on the cover in all the stores and tourist spots one month. The girl even smells nice. She wears something subtle. I don’t know what it is, and have never asked, but it is like a coconut soap or something.
Me, on the other hand, I’m not at all like Cindy. I’m short, too skinny, and I have ridiculously small breasts. How small, you ask? Well, they don’t even qualify as boobs. They’re just tits – little things topped with small, dark nipples. I’m three-quarters Filipino, so I’m quite brown, but I have a white grandfather. The only good thing I have going is my long, dark hair, which when I let it down, comes to the top of my butt. I know it’s kind of weird, but I do like to stand naked in front of my full-length mirror looking at my silly self. I mean, I know I’m not much, but I get all horny looking at myself. Is that weird, or what?
There’s another big difference between Cindy and myself. Her family is really wealthy, and mine is just average. She could literally buy boyfriends if that’s what she wanted. It turned out, however, that all she wanted at the time was to play pickleball. I admired her sense of focus. When she and I had sleepovers, and we got to talking about boys, we were both wistful, but she wasn’t all that interested, whereas I was absolutely boy-crazy.
Dare I say it? Yes. Virginity be damned. The fact is, I wanted to get fucked. Plain and simple. But not with someone like Al. It would have to be a nice guy.
Cindy’s family, especially her father, are rather rebellious. My family, on the other hand, are quiet, proper and conservative.
Her father, George, is an inventor. He has a most spectacular workshop on their property filled with all sorts of equipment, and a big junkyard of everything imaginable in another building next to the workshop. If you need a lawn chair hinge, a cord for your vacuum cleaner or bearings for your blender, go ask George, He’ll have it, and give it to you. What makes him happy is having what you need. And if it doesn’t exist, he’ll make it.
Whenever we go to tournaments out of town, it’s George who pays the expenses. He usually goes with us, and if the situation allows, he’ll play a bit of amateurish pickleball himself. Actually, he isn’t that bad for an older guy.
I’ve always been amazed at how well some people can play the game. I’ve even seen some folks in their eighties that can move around the court quickly and have reflexes like teenagers.
One thing I found disconcerting about George Montrose is that he doesn’t always wear clothes. I’ve seen him in the nude while working in their yard, in his workshop, or just hanging around their house. When I slept over, which I often did on the evenings before leaving for tournaments, he’d act as if everyone’s father goes around nude. No big deal.
It freaked me out at first. Especially the part about seeing his penis and testicles. I’ve only seen pictures of nude people on the Internet, so seeing him like that in person was quite a shock at first. Cindy should have warned me.
I saw her mother running around the house a couple of times totally nude, or wearing an unfastened bathrobe a few times, too.
Cindy and I talked about it later – why she didn’t warn me, and she said she ‘forgot.’ To her, it is so ordinary that it didn’t occur to her to say anything. Crazier still, after Cindy came out of the shower one time, she neglected to put anything on for a while. She just laid on her bed, while I laid on my pad on her floor, and we talked, like always, about pickleball and boys. It was weird that first time, but I got used to it. However, I never got so used to her nudity that I went without clothes except the usual stuff, like in the school showers. In fact, if anything, the Montrose family nudity caused me to wear clothes more than I might otherwise.
One time, she told me her father refers to bras as ‘cancer covers.’ I asked what that meant, and found out he thinks that women overheat their boobs by wearing bras, and that can be a factor in breast cancer. After hearing that, I did tend to wear bras less often. Funny thing about me: I can get away without wearing a bra. No one notices a flat girl like me anyway.
Well, occasionally I’ve worn a padded bra. I might look weird, but I think it would be more weird, just plain wrong, in fact, to wear padding, as if I have more ‘up there’ than I actually do. To tell you the truth, the whole thing is crazy. Why does our society teach that huge boobs and large penises are such an big deal?
So here we were eighteen years old. Cindy’s father was enjoying pickleball more and more, and I had to say, the balding old guy was getting pretty good. He was even losing weight, and attributed it to pickleball.
A couple of times he’d come out to the courts, dressed of course, playing on the same side as Cindy, with me playing with some random pickup guy, and sometimes they won.
The problem with the public courts is they are so crowded. One thing I hate is waiting between games while other people use the court. We usually have around eight players per court, meaning we get to play only half the time. In a recent report on CBS television, it was said that there are two million pickleball players in America, and within two years, there are supposed to be eight million. It’s the fastest growing sport in America. I’m glad, but also concerned that all the courts will be overrun.
One thing about Cindy’s dad: He doesn’t just sit around hoping things will get better. George takes action. Not only has he invented a boatload of gadgets to make home life better, he even does things like speaking at city council meetings.
George’s response to the pickleball problem was to build his own court. He had some construction guys make a large concrete pad, put a fence around it, had the surface painted, and then had a net installed. He even had night lighting put in. It must have cost him a fortune! But, that’s something he has, a fortune.
I was delighted. I was getting pretty tired of the public courts, always jammed with beginning players, and all the waiting around.
The moment it was finished, Cindy and George invited me to come play. I was wondering who the fourth was going to be. Fuck, it was my good old nemesis, Al Weissman. As soon as I saw him, my stomach dropped out, again, just like it did every time he showed up.
It was a hot August day, and we played a few rounds. Al and I beat Cindy and George easily for two games. Then Al started in on his usual routine. He critiqued pretty much everything I did. We lost the third game. Not because of skill, but because I was getting mad as a hornet, and that caused me to play badly. I think it was pretty obvious to the Montroses that I was losing it.
Another thing about George is he loves unconventional solutions. Being an inventor and all, he is an experimenter. He experiments with people, relationships, and human interaction just like he does with metal, plastics, and electronics. So right then and there, to rescue the bad vibe that Al and I were giving off, he tried another experiment. I hated it immediately.
“It’s hot out here. Let’s play nude.”
“Oh, Dad,” Cindy moaned.
“George, you’re kidding, right?” was Al’s response.
For once, Al and I were singing the same song.
“Not kidding. Let’s play nude, or this is my last game.”
That would have been a waste. We had just got started, and I’m never satisfied with just a little bit of pickleball. It isn’t a session unless it goes two hours. Besides, if we pissed George off, it would be back to the public courts for us.
Even though George had built the court under shade trees, it was still a terribly hot day.
Cindy, with a twinkle in her eye, said “I’m game.” She had been working pretty hard lately to get me to be more clothes-free. I didn’t know if it was because she really believed in nudity, like a religion or something, or maybe she had slight lesbian tendencies.
Maybe I shouldn’t say this, but if she was lesbian, that would be OK with me. More than once, I masturbated with her vaguely in mind.
Without warning, Cindy stepped out of her bikini, becoming totally nude except for her socks and shoes. For me, no big deal, but Al was shocked. He didn’t know anything about the Montrose family nudity, and suddenly he was seeing this gorgeous, strawberry blond girl as naked as the day she was born.
I should point out, that for her, nudity doesn’t stop at being clothes-free. Her pussy is nude too. She removes the hair from her crotch region. I have to admit that I admire her boldness. I could never do that.
Wordlessly, and as casual as a cucumber, following his daughter’s lead, George stepped out of his shorts, carefully removing them from around his tennis shoe-clad feet.
Looking at Al, I was somehow delighted to see he was red in the face. The Montroses were naked, but it was Al who was embarrassed.
As if it wasn’t weird enough for him already, along came Mrs. Montrose, pleasantly plump, and also totally nude, even barefoot, with a tray of lemonade.
Normally, I would have been the prude I normally am. I don’t know what I might have done. Walk off in a huff and drive home? Lecture the Montroses on proper behavior? None of that would do. Maybe I could have continued playing pickleball, in my T-shirt and shorts, as if nothing was different, if George would have it. But no, that wasn’t right either. Plus, George was threatening to quit if we didn’t go along with his plan.
I think the deciding factor was to further shock and embarrass good ol’ Al. That would be worth it’s weight in gold. Besides, Cindy had been pressing me forever about ‘getting more sun,’ ‘losing the cancer cover’ and all that. Maybe this was a good time.
So, I, Jenelle Watson, the quiet, demure girl, pulled up her T-shirt, took off her bra, then in a single swoop, stepped out of her panties and shorts together. I’d like to say I was completely casual about it, but no, I was shaking like a leaf. At the same time, I felt it was a bold move, and somehow it made me feel powerfully free.
Jugding by the look on his face, it was all Al could do to keep from drooling. Or, maybe I was imagining it. It seemed my nudity had an effect on him. He seemed hypnotized, or maybe even paralyzed. As he was staring at me, I really wanted to cover my little tits and my crotch region with my hands. It was all I could do to keep from folding my arms in front of myself, but if I did, I think George and Cindy would have laughed at me or something.
After maybe a whole minute, Al broke his trance, quietly, and somewhat resignedly saying, “When in Rome…” He then stepped out of all of his clothing except his socks and shoes.
That was not what I was expecting. Not by a long shot. I thought he’d be indignant, or dumbstruck, or something like that, and go home.
He was also not what I expected to see. The guy was actually better looking without clothes. I have to say, as obnoxious as he was, he still happened to be a good-looker.
He was a bit thinner than I expected, especially his hips, and his ass was downright little, much like George. I was starting to understand that men are typically smaller around the hips and ass than women. Al made up for it with a large chest, wide arms, and surprisingly huge leg muscles. I was immediately drawn to his well-defined six-pack.
Totally unlike hairy old George, Al was very smooth. He had a slight covering of hair on his lower legs, a nest of darker blond hair around his genitals, and nothing more but what was on his head. I noticed that even the genital hair was trimmed, being only around a half-inch long.
Something else I noticed, which I accidentally stared at, until I caught myself, was his penis. It wasn’t very big, but it was very exciting. Just seeing that, I felt a twinge between my own legs.
‘Geez, Jenelle,’ I was thinking. ‘It’s only bothersome Al,’ as I made a point of looking away.
“Well, come on,” Al announced just a bit too loud.
Our pickleball resumed. It didn’t take long for the situation to normalize. George was playing well, Cindy was playing very well, but of course with Al on my side, we won every game handily.
Unfortunately, within a half-hour, fucking Al was up to his old tricks. Telling me that I should have dropped shots into the kitchen that I successfully drove down the sidelines, and so on. For once, I decided to ignore him. Not so much ignore his instruction, because I always did that, but to ignore the effect it had on me. ‘Water off a duck’s back…’ I was telling myself. And it was working.
I don’t know if it was the nakedness, or what, but I was starting to be OK with Al carrying on the way he does.
A few more games, and it really was too warm, even with us being naked. We went into the Montrose’s air conditioned house, a very large home, and hung out in the kitchen along with Mrs. Montrose, and Cindy’s older brother, Jason. He didn’t say much, stayed for a few minutes, then drove off somewhere in his vintage Volkswagen van. While he was there, he was naked, we were all naked, and it didn’t seem like anything to me. It was amazing how fast I had acclimated.
Out of the corner of my eye, I caught Al staring at me several times. It was good for him, I thought, to see something he can’t have. I don’t know why that notion came to me, but it almost made me laugh out loud.
The next morning, I had a client at 7:45 am at the public courts. That’s the only time you can be assured of having uninterrupted court time. I had started taking on the occasional pickleball coaching job. This client was very typical of my small clientele, a sixty-something woman who wanted to improve her game. I ran her through some drills – drop shots, air rallies to help her pick up her speed, and cross-court dinking. At 9am, most of the regulars started arriving.
Al showed up early, at 8:45, uncharacteristic for him. He came over to me, and it was quickly obvious he wanted to talk.
“Hey, Jen.”
“Hi, Al.”
“Um…, so what did you think about yesterday?”
“Oh you mean with George and Cindy?”
Somehow, I didn’t want to discuss the nudity aspect.
“Right.”
“It was nice. George is coming along amazingly well for his age, don’t you think?”
“Uh, yes, he is. Hey Jen, I had a good time.”
What the fuck was he trying to say?
“Yeah, it was OK.”
I wasn’t about to reveal how fantastic it really had been. I found myself really enjoying the slight breeze on my tits, ass and vagina. Having never been nude outdoors before, that was an unexpected treat. It had also made me terribly horny, and I had rubbed one out as soon as I got home.
“Do you think they’re going to invite us back, make it a regular thing?”
“Al, I certainly hope so. These public courts are becoming much too crowded, don’t you think?”
I was also feeling this was the perfect time for a teaching moment for the annoying prick.
“Al, I’m not sure whether George will invite us back or not. I think he has a little trouble with our bickering. You know, you and me.”
“Funny thing, Jen, I was thinking along the same lines. Let’s try being more civil from now on.”
“Woah, big guy! How about you try being more civil.”
“But you can act any fucking way you want?” he said, his voice several decibels louder.
“I’m always civil, and you know it.”
Mocking me in a syrupy high voice, he said, “Oh, lobbing is stupid except as a defensive move.”
I had to admit to myself, I have told him that several times.
“Fuck off.”
“You fuck off.” At which point he walked away to one of the lower courts, and got in a game with some intermediate players.
That didn’t go the way I wanted. His offer of reconciliation, or at least his idea of trying to act better around each other wasn’t half-bad. We might make some progress, if we could actually do that. More important, we might be able to stay on George’s good side so we could keep getting invited back to Cindy’s place for private pickleball.
Internally, I was telling myself that the reason for going back would be entirely about having uninterrupted court time with good players. The real reason, which I wasn’t ready to consciously admit, was that I really, really enjoyed the nudity! Weird, eh?
George did invite us back. It was an unseasonably cool day, so everyone remained clothed. Good quality pickleball to be sure, but I was disappointed. Even Cindy, who usually wore bikinis all summer, was wearing a T and shorts.
I remember asking her about the bikini situation once. Most pickleballers dress more modestly. She told me that her bikinis were consciously considered for two reasons: One, she could play better if she wasn’t as hot. Now, I’ve always thought a loose T-shirt keeps one cooler in the hot sun, but I understood her point. The second reason, she said, is that it threw the guys off a bit. It probably did. She was a beautiful girl, unlike me.
The next time, it was warm again, and sure enough, everyone, with Cindy taking the lead, played naked. I was overjoyed. If that’s all I did for the rest of my life, playing naked pickleball, I’d be happy.
That couldn’t be, of course. I was headed to college in six more weeks. So was Cindy. So was Al, for that matter. I didn’t know Al’s plans, but I knew that while I was going to study right here at the community college, Cindy was headed to a fancy university three hundred miles away. Bummer.
I got a text from Cindy. George wanted to make it a regular thing. Yeah! Three days a week, at 9 am, for the rest of the summer, the four of us were going to play at the Montrose’s court. Furthermore, he said we could bring friends, and play anytime on his property, even after dark with the lights on, up to 10pm.
We took him up on the first part of his offer. The four of us played three times a week. We didn’t take him up on the second part. I believe that was because we all, secretly, enjoyed playing naked, and didn’t want to mess that up by inviting what George called ‘textile’ people.
After only two more sessions, George announced that he was dropping out. Starting with some sort of marketing convention he was attending next week, he’d be tied up in various projects for the rest of the summer. You’d think I’d be happy to be getting rid of adult ‘supervision.’ You’d think we’d feel restricted by having a guy nearly three times our age hanging out. But the fact is, I liked George. He was certainly young at heart. He was funny, and he didn’t seem like a father. He seemed more like one of us. Plus, he wasn’t half bad as a naked guy. I liked how he shaved his chest and genitals, and although he had a belly, he was really quite fit. He was also, like Cindy, tanned all over, and that was somehow appealing.
Cindy, Al, and I were faced with a dilemma. Who would replace George?
There was a guy we all considered. It was Kelly Simpson. He was kind of a computer geek-like guy, but he played pickleball extraordinarily well. At our level, spins aren’t used much, but he was a spin genius, flummoxing us frequently, yet able to do all the other things that make good pickleball also. We didn’t know much about him. He seemed to keep pretty much to himself. He wore thick-framed glasses that he held on with an elastic band around his head. That didn’t help his appearance in my opinion. Come to think of it, if he’d lose those glasses, he would actually look pretty good. Tall, with short-cut curly black hair, a matching beard, and a thin, athletic build, he wasn’t really all that bad.
But how do you ask a guy like that to play naked pickleball? And naked it would be. There’s no way that Cindy or I, and probably Al, too, would want to go back to textile pickleball, except on the public courts, of course.
We decided we had to invite him. It was either that, or no pickleball at the Montrose’s. I was chosen as our emessary, since I knew him best, which truthfully, was hardly at all. I had won a tournament with him once.
A day later, I was on the public courts around 6pm, and I caught up with Kelly.
“Hey, Kelly!”
“Yah, hey Jen!” he responded in his somewhat quiet way.
“I’d like to invite you to join a foursome.”
“Really? I’m honored. When?”
He was assuming I meant on the public courts. “It’s really more a question of where.”
“Oh, I don’t really want to drive to Eastport.”
That was the closest place to play pickleball besides our courts, but it was a half-hour away.
“No, not there. You know Cindy Montrose?”
“Yeah, a little bit. We’ve played together a few times.”
“Well, her dad built a private court at her place. It’s only like five minutes from here.”
“Cool!”
“We’ve been playing everyday at 9am. We want to get good. I think Cindy has a chance at winning Nationals in a year or two.”
“So do you.”
“Thank you, Kelly.”
“Anyway, you’d make a good fourth.”
“Really?”
“Yes. But there’s one thing.”
“What’s that?”
I believe he was thinking I was going to critique his extreme use of spins or something. Actually, at that very moment, I was at a total loss for words because I had to tell him about the nudity thing. If he wasn’t into it, it would be a deal-breaker. We were really cherishing our nudity. Worse, it would be totally embarrassing if I said we play without clothes, and he reacted badly. He might laugh. He might get disgusted or all religious or something. He might blab it to the other pickleball players. I hesitated for a very long time.
His face scrunched up as I hesitated. I can only imagine what he might be thinking. What, exactly, was I going to say? I was thinking furiously, but nothing was coming up.
“Well, look. give me your phone number, and I’ll text you.”
That was stupid, but that’s what I said.
“Now, you’ve got my curiosity up Jenelle. What’s the deal?”
“Look Kelly, I really can’t tell you right now,” I said, feeling completely ineffective and frustrated.
“OK, whatever,” he said, looking a bit put out with me.
All evening, I was trying to figure out what to tell him. By bedtime, I still hadn’t figured it out. I didn’t sleep well, and by the next morning, I still had no idea.
I texted Cindy, explaining the whole situation.
“Send him this,” she texted back, and attached a picture Mrs. Montrose had taken of the four of us playing naked pickleball. It was blurry and distant, so you couldn’t quite tell if we had clothes on or not.
“No fucking way!”
I phoned her and we discussed it. Finally, we had a plan.
Late in the morning, we texted him that the two of us wanted to meet up on the public courts. After a bit of going back and fourth, it was decided we’d meet at two o’clock.
We met him there, then pulled him over near the parking lot, out of earshot of everyone else.
Cindy and I looked at each other. She’s normally the bold one, but she remained silent. It seemed to fall to me, so finally, as he was looking quizically back and forth at one, then the other of us, I just blurted it out, “Sometimes we don’t wear very much clothing.”
“Well, it’s hot these days. That’s sensible,” he replied thoughtfully.
“No, she means we wear literally nothing,” Cindy chimed in.
“Oh… Oh! That’s weird.”
Our ship was sunk. I could sense it. He was going to react badly.
“Let me think about it,” was his reply.
And that was that. He walked back to the courts, and we played some pickleball. It turned out that Al was there, and the four of us got a court together. We managed to play one game before we got mixed up with other players in other games.
I was kind of freaking out, imagining all sorts of bad outcomes, and I’ll bet Cindy was too. What was Kelly going to do?
That evening my phone went ching, and I had a text. It was from Kelly. “It’s weird, but I’m in, if it’s for real. Not some kind of prank or something.”
I texted, “No prank.”
He texted back, “Because there’s no way you’re going to get me in some kind of trap, take pictures, or something.”
“No trap. For real. Here’s the deal. The three of us will be nude first. If you’re uncomfortable, just go home, No problem.”
“OK.”
“Cool. Meet us at 9am, here’s the address: 1624 Porter Road. Turn right just past the green mailbox. Drive in. Go left at the fork. You’ll see the pickleball court. Have any trouble, phone me.”
We decided to put him at ease right away. George was still here, so he, Cindy, I, and Al arrived early, stripped, and started playing.
A couple minutes before 9am, Kelly pulled in, sitting in his car a good few minutes before getting out. That concerned us. I was wondering if he’d turn around and head home without even stepping out. From where he was sitting, he could see the court, and see that we were all naked.
He did get out of his car, carrying his pickleball paddle and a water bottle. He was dressed in a safari hat, shorts and an alligator shirt. I had forgotten that he likes that full-coverage hat. He was one of those guys who worries about getting too much sun. Probably sensible. It was a good thing George built the court under shade trees. Kelly threw the hat back in the car before closing the door. He then walked slowly, very slowly, toward the court, as if he was on a death march, or a trip to the dentist or something.
We said, “Hi.”
He said, “Hi.” You could see that he was trying to act as if everything was normal. For us it was normal, but for him, he must have been fighting his way through a storm of emotions. I mean, being a typical red-blooded American boy, he’d love to hang out with nude girls. On the other hand, getting naked among people for the first time is a very scary experience, as I recently learned myself.
“Kelly, you’ll take over for me, won’t you?” George asked. “I’m headed back to my workshop.”
“Um, sure, Mr. Montrose.”
“Oh, George, please.”
Kelly walked through the fence and onto the court fully clothed. Was he planning to stay clothed while we were naked? That would certainly be awkward.
“Are you going to play like that?” Cindy asked, seemingly a bit unsure of herself.
“Well…”
“Well what?” Al asked.
“Um, well…, well what if I get an erection?” he finally blurted out.
Al laughed good naturedly. “Dude, it’s natural. I get them all the time.”
The funny thing was, Al never did get an erection. We had yet to see Al or George with erections. I suddenly wondered why that was. I think if I were a guy, I’d have gotten a boner seeing Cindy like that, all nude, with her beautiful boobs flopping around and all.
“Well, OK,” Kelly answered tentatively, then started slowly pulling his alligator shirt over his head, then removing his shorts and briefs.
“Not bad,” I was thinking. He was still wearing his glasses, but the guy looked pretty good. He was much hairier than Al, with a light coating of curly hair on his legs almost all the way to his hips, hair on his chest, and even on his shoulders. He crotch was a literal carpet of curly black hair with a thin trail leading up to his belly button. You could barely make out his genitals.
My reaction was all too typical for me. Seeing Kelly all naked, gave me a feeling of excitement in the pit of my stomach as well as a good jolt in the vagina. I guess I’m a sex freak. What can I say?
The four of us just started playing pickleball, and everyone had a good time.
Mrs. Montrose came out after an hour with refreshments. She, too, was naked.
Here’s where the story gets weird, but it’s absolutely true. Now, Mrs. Montrose is a plump lady. Not horribly fat or anything, but she has some weight on her. She’s also old, like 45 or something with graying hair. She set the tray down on a little table surrounded by lawn chairs just outside the court, and waited for our current game to end. We came out, and all sat down with her, thanking her for the drinks and making small talk.
I happened to glance over at Kelly who seemed to be staring at Mrs. Montrose on and off, and he was trying to hide an erection by holding his glass of Coke in front of it. It was all he had, and wasn’t doing a very good job of hiding anything. He would have been better of not trying to hide, because that actually brought our attention to the matter.
To everyone’s credit, no one said anything.
I can imagine that if I were a guy, I’d be terribly embarrassed.
Soon, Mrs. Montrose left, and we went back into the court. By then, his erection had subsided. That was the first time I had ever seen a real, live human being with an erection. It had a funny effect on me. I couldn’t wait to get home and frig myself silly.
I guess he got over it, because after we were done, Kelly went home all smiles, and it was obvious he was going to become our fourth. The remaining three of us gravitated toward the table and chairs. It was a hot, humid day, so the natural thing to do was to just sit lazily around, talking.
I was still all horny, which I think is behind what I did next. I turned to Al, right there in front of Cindy, and said, “How come you guys don’t get erections all the time, around us naked girls?”
He thought about it for a minute. I thought he might just say “Fuck off” or something, but he gave us a serious answer.
“When I first started playing with you and Cindy, I was worried like crazy about that very thing. Like, you’d get upset, or mad at me, or think I was a perv or something. But it just didn’t happen. I’ve thought about it, and I think it’s because the potential embarrassment trumps the horniness. To tell you the truth, I’d be horrified to get a boner in front of you.”
Cindy, probably without thinking it through said, “We wouldn’t mind!”
I thought it through, and decided I’d get a real kick out of seeing Al with an erection. So I said, “Dude, if you ever happen to get erect around me, I’d be honored. There’d be nothing to be embarrassed about.”
“I wish you girls had the same problem.”
“Huh?” Cindy and I said in unison.
“I mean, you don’t have anything that gets erect. You could be all horny and us guys would never know.”
“Why is being horny a bad thing?” Cindy wanted to know.
No one had a direct answer, but Al did say, “Well, we can’t keep it a secret. There’s no lying or deception. If I find you attractive, I’ll bone up, and there’s nothing I can do about it.”
“Oh, so you don’t find us attractive?” I impulsively asked.
“Quite the contrary, Jen. I’ve been working very hard not to show it.”
“Why on Earth?” Cindy asked.
He was turning red in the face. I think I was too. “I don’t think the feeling is mutual. In fact Jenelle hates me, or at least, she doesn’t like me.”
I don’t know why I said what I said next. It didn’t make any sense, but I felt really strange. I was chagrined that I had acted so badly with him up until a couple of weeks ago. It just then occurred to me that I rather liked Albert Weissman. “What makes you think I don’t like you, Al?”
“Well you don’t, do you? I mean we always argue.”
“Used to argue,” I corrected.
“So you think I’m alright now?”
I felt my cheeks burning. “Well, dude, you’re OK.”
For some reason, Cindy thought this was hilarious, and started laughing. Al and I started laughing also.
“So, you’ve been hiding your erections from me?”
“It doesn’t exactly work like that.”
“What do you mean?”
“Us guys don’t have as much control over that as you might think.”
“But we’ve been playing pickleball all this time, and you’ve been staying, um… soft.”
He thought for a minute, then gave up. “I guess you’re right. The whole thing, you know, human nature and all, is pretty weird, isn’t it?”
Sometimes Cindy can be a jerk. “Al, do you ever, you know, get yourself off, thinking of Jen?”
Oh my fucking god, she didn’t just say that, did she?
He didn’t answer for quite a long time. Then he said, “I take the fifth.”
It just kept getting weirder! His cheeks were red again. I’m sure mine were too.
Sometimes I can be incredibly stupid. I suppose horniness can drive me to temporary insanity. Because what I said next was insane. “It’s OK, Al. Sometimes, visions of you come to me when I masturbate.”
“Really Jen? I had no idea. I thought you hated me!”
“Oh, I did, a while ago. Not so much now.”
“Cool!” was all he said.
Cindy snickered. I barely noticed. She had receded into the background, and Al filled my vision entirely. I had this weird urge to put my arms around him, and what? I wasn’t sure, but it felt like I wanted to kiss him.
Cindy wasn’t done being weird. She must have become horny, too. “Al, what’s it like when a guy masturbates?”
After another long hesitation, he answered, again seriously, “I suppose it feels the same as when you do. You do do it, don’t you Cindy?”
Touche. He got her back. Now, Cindy was blushing. “Yup. Doesn’t everyone?”
‘Smart response, Cindy,’ I was thinking.
No one said anything for a very long time. We started looking over at our clothes, as if we were ready to put them on and go home.
Suddenly, Cindy, asked, “Al, will you show us?”
That brought the attention of both of us girls to his penis. We somehow both started staring at it.
“No! That’s crazy!” As he said it, I saw something magical. His penis was becoming a bit larger. I was pretty sure it was becoming erect. Was it the fact that we were staring at him? Was that taking him over some sort of edge?
Cindy said, “I’d show you, if you asked.”
I just couldn’t believe where she was taking this conversation. As horny as I was, she must have been over the top. I was becoming very excited, and felt the blood rushing to my head.
Then, I came to realize Al must have been as horny as us, because he said, “Well, if both you and Jen did it, I’d. well… I’d probably go ahead and do it, too.”
By now, his penis was erect for sure. No doubt about it. It was sticking straight up. I had a surprisingly strong urge to reach out and touch it, but of course I didn’t.
I looked over at Cindy. She had one hand laying loosely against her pussy, and to my shock, I realized she was just gently running her finger along the slit, right here in front of us!
“Hmm, Al. You know when you said that us girls don’t show it when we get excited? We do have little erections. Our clits get bigger. Look.” And with that, she spread her inner labia with her fingers, showing her little pink bud.
Perhaps even more shocking is what happened to me when I saw that. I felt a huge turn in my lower stomach and vagina. It was like an electric shock.
If I had the freedom to just do what I really wanted to do at that moment, I would have started masturbating like crazy. But I was too reserved. Or shy, or something. I just couldn’t.
George Montrose popped out the front door of his house, fully clothed, at that moment, jingling his car keys on one hand, and walking briskly to his Range Rover.
“I’m off to get some clamps.”
He paused for the briefest moment, seeing what his daughter was doing, and seeing Al sitting there with a big, obvious erection.
Al had a look of horror on his face. He had been caught naked and red handed with a woodie by Cindy’s father. Glancing at Cindy, I saw something else. It was pretty obviously that her dad had seen her showing us her clit. But she seemed alright with it.
Smiling in a way I’d call ‘sweetly,’ George simply said, “Hey kids, you know how to play safely, right?”
“Oh, Dad!” Cindy replied, sounding exasperated.
“No penetration, OK?” George replied.
From Cindy, “Geez! Of course we’re not going to do anything like that.”
“Well, I’m not saying you can’t play. Just play safe, alright?” And with that, he climbed into his car and drove away.
There’s absolutely no way on Earth my dad would have reacted like that. It would be yelling, a lecture, and I’d be grounded for a week. And there’s no telling what he’d have done to Al.
Al must have thought something similar, because when I looked back at him a minute later, there was no erection left in him. He was soft and small again.
The mood had been wrecked, and we all went home. I had a lot to think about. It seemed that obnoxious old Al pretty much said he liked me. And then, I took that erection as proof. Of course it might have been Cindy that caused the boner. Hmmm…
The next thing I knew, I was rubbing myself to two orgasms in a row, a fairly rare thing for me.
We played pickleball on the public courts on Tuesday. At one point, all four of us were there, but we never got into a game with all of us on the same court. Being another sweltering day, we didn’t play very long, and the four of us met up at a picnic table in the early afternoon. We were out of earshot of the other players, and I was sure someone would say something to someone. But no, everyone was too reserved, and all we talked about was pickleball. When Cindy mentioned meeting up tomorrow at her place, I believe we all smiled big-time and showed positive reactions.
As we broke up, Al did something weird. He walked up to me looking all strange and hesitant. Then he leaned forward and gave me a quick little kiss on the cheek, saying “See you tomorrow,” as he walked away.
I was at a loss for words. I placed my hand against my cheek, as if I could feel some sort of change there. Trying to sort out what I felt from that quick little action, I came to the conclusion I kind of liked it. I felt honored. I was also amazed that he was showing some sort of affection to me. If he had kissed Cindy, that would have made more sense.
Back in my bedroom, casually masturbating again, I suddenly had a vision of having sex with Al. Then I tried to imagine what it would feel like to have that penis of his inside me. I walked over to my dresser and picked up my hairbrush. The handle was penis-like in it’s general shape and hardness, but shorter and smaller in diameter. Never-the-less, I put some of my girl juice on it, and drove it and out of my love hole, imagining it was Al’s penis. That resulted in a crashing orgasm. How crazy is that?
The next morning, for the first time, I felt hesitant about showing up at Cindy’s. I think I was actually afraid of something, although I couldn’t verbalize just what.
Dragging my feet, I arrived a few minutes late, to see that Cindy, Al and Kelly were already there. All were naked. Kelly seemed to be half-erect. He was paying no attention to it, as they were warming up with dropshots and fast air rallies. Interesting.
We played our pickleball. It was always Al and I against Cindy and Kelly. I noticed that Al kept looking at me. It made me feel shy, but also kind of special. I noticed that Cindy was looking at Kelly the same way, and if I’m not mistaken, he was looking longingly at her also. Kelly’s erection had gone down naturally about ten minutes after we started, but it came back a couple of times for a minute or two. He ignored it. We ignored it also. That seemed like the right thing to do. I didn’t know much about men’s erections, but I guessed that maybe Kelly is more prone to boners than other guys like George or Al.
About an hour in, Cindy was drawn out way sideways trying an around-the-post shot, and she just collapsed, falling hard, laying there, and holding her ankle while moaning. I was horrified. I’m sure we all were.
Al came over to her right away, was talking quietly, and then put both hands around her ankle. Continuing to talk quietly with her, so quietly I couldn’t hear the words, he very gently removed her shoe, and massaged her foot.
Meanwhile, Kelly and I just stood there, not knowing what to do. After a few more minutes, Cindy put her sock and shoe back on, got up, took a couple tentative steps, and announced, “I’m OK.”
I was glad that Cindy wasn’t seriously hurt. I felt something else, too. Something I wouldn’t have expected. I felt proud of the way Al handled that.
Being yet another hot day, we gravitated to the chairs under the shade tree after another half-hour or so. No erections this time, just two naked girls and two naked boys hanging out. Literally.
Cindy and Kelly were kind of joking with each other. At one point, she tilted sideways in her chair nudging him in the side with her shoulder. He was smiling ridiculously.
A dynamic was developing which was becoming unmistakable. It was two couples, Kelly and Cindy, Al and I. Oddly, I was feeling pretty good about that. A person could do worse than Albert Weissman. Oh, he wasn’t the big football star in school, but he was quite a looker. He was a thin-neck athlete, not a thick-neck jock. And more than that, he was turning out to be a nice guy.
While Kelly and Cindy were getting all personal, and more into each other, ignoring Al and I, he grabbed my hand, and suggested we go for a little walk. There were trails into the thick woods right behind the Montrose’s property, so we set out on a brief walk, still clothes-free, other than our shoes and socks.
As we walked, we talked about this and that, nothing special. Then, at the side of a small creek, we both stopped, and as natural as you can imagine, we turned to each other, and just started kissing. It was time. It was right, and we knew it. We continued kissing, and I was feeling minor shockwaves running throughout my body including the top of my head. I felt something pressing against my lips, and realized it was Al’s tongue. I let him in, experiencing the first real kissing in my life. Oh, it was something! During that, once again my mind flashed to the thought of his penis in my vagina. I was momentarily light-headed, and weak-kneed.
And speaking of penis, I felt it. His penis was pressed against my lower belly, and it had become hard! My knees almost buckled. I tried to stand up a bit better, and then they did buckle. Al caught me as I was starting to collapse, and putting a hand down to support us on the soft, leaf-covered ground, he gently let us collapse. We resumed kissing.
I couldn’t resist. I placed my fingers around his stiff rod. Oh my, what a feeling! It was soft and hard at the same time. Silky soft on the outside, and hard like a bone on the inside. I never realized why they call them “boners” until that moment. I felt such a longing in my pussy. It was very specific. My body wanted that inside me!
At just about the same time I had grabbed his penis, he had placed his hand on my left breast, and was kneeding it gently. I almost didn’t notice with all the other sensations, but suddenly, aware of that, I was just beside myself with… I don’t even know how to describe it. Horniness, happiness, fear, longing, just a whole mix of emotions.
Voices. We heard talking. I had forgotten that land we were walking on was a seldom-used section of a public park. People were coming right toward us. We sprang up, and went very quickly back to the Montrose property. If we had stayed in the woods any longer, we might have been discovered. I felt uncovered, foolish, and a very long way from my clothes until we got back to the pickleball court.
Nothing more happened that day. The next day, Cindy texted everyone, saying that for the rest of the summer, we’d play at her house not every other day, but every day. I was all for that!
9am found us all there again. as usual, Kelly started out with an erection. It was becoming normal for us. Although, it still seemed awkward to me. How can a guy run around with that thing waving in front of him like that? Kelly’s stiff rod reminded me of a vacuum cleaner attachment, something just stuck onto his body. Come to think of it, Cindy’s big boobs seemed kind of surreal to me as well. I’d see them swing back and forth in unison whenever she made a sudden sideways move. I guess, to her, it was normal. I suppose I’ll always be a small-titted girl. Might as well get used to it.
At one point, I noticed my partner, Al, was sporting a full erection for the first time during pickleball. My belly did a lurch. Suddenly, where a moment before our nakedness had seemed normal, and innocent in a way, it all changed. I wanted to fuck that guy. Al became a conquest to me.
Not thinking clearly, right in front of everyone after we finished playing for the morning, I invited Al over for dinner. Since my parents were going to be out, that was the perfect opportunity.
What I didn’t count on was Cindy saying, “I’ll bring some homemade pizza.” How could I tell her I was planning a party for two? I couldn’t.
That evening, it was me, Cindy, Kelly and Al at my place. We were clothed, of course. It felt strangely odd having clothes on with these three, but that’s what we did.
“Hey Jen?” Cindy asked. “Are your parents going to be out for a while?”
“Yeah, they’re playing bridge. They won’t be back until after 11. Guaranteed.”
“Cool!”
I could tell Cindy had something more on her mind.
“What, Cindy?”
“Well, we could be naked, right?”
“Way to go, Cindy!” Kelly exclaimed.
I don’t think anyone wanted to stay clothed. Before you could say “Kalamazoo, Michigan,” we were all naked. Both Kelly and Al were sporting erections right away.
“Look, I’m erect too, Cindy added, pushing her lower body forward, and holding her inner labia apart with her fingertips. How about you Jen?”
The next thing I knew, my good friend Cindy took everything to a whole new level by letting go of her own labia, and coming toward me. She knelt down, and somewhat awkwardly, placed her fingers against my vagina and attempted to spread my inner labia. It was difficult because of my hair down there. My body reacted before my brain could argue. I reclined on the sofa in such a way that Cindy had better access.
I may have surprised her with my wetness. Whenever I’m sexually excited, I get really wet. As I understand it, that’s not common. Most women get only a little wet, but I can literally make puddles.
Now it was Al’s turn to be weirdly forward. “How about your nipples, Jen? They seem to be erect also.” Coming toward me and kneeling next to the sofa right next to Cindy, he just started running his fingers over my nipples, and then started lightly pinching them while rolling the back and forth slightly.
Oh my god, that was just amazing! I wouldn’t have thought having a man touch my nipples could do that to me. I became wetter, and I felt something like an electric shock run through my body. To make matters worse, his long, thin penis was right near my eyes, giving me a great view. I even noticed his slotted peehole. Until that moment, I didn’t know they were slots. I thought a guy’s peehole was round, like mine.
Under the circumstances, what I did next probably wasn’t so crazy. I had been feeling perhaps a bit prudish, in that I wasn’t fully participating. So I said exactly what I was thinking.
“I didn’t know guys’ peeholes were slots.” I reached out, and started touching the end of Al’s penis, running my finger lightly over his peehole.
After a minute, I stopped.
“Oh, keep going, that feels great!”
I reached out again and started slightly spreading it open with my fingertips. I found out it is round after all.
“Let me see yours, Kelly.” Woah, did I just say that?
It took no convincing. Kelly stepped right over to me, and I examined his peehole the same way. His penis was a bit larger than Al’s, and his foreskin came over the end, so I had to push it back first to see the tip of his penis. Oh, it felt amazing to touch his super-soft foreskin.
As if I hadn’t acted strangely enough already, I then said, “See, here’s what mine looks like,” and I then spread my labia open so the boys could look inside and see my peehole. They both came close and stared like their lives depended on it. Cindy came closer too. My fingers slipped off my labia because they were so wet with girl juice. I started to spread them again, but Al gently pushed my hands aside, and took care of that chore himself. Ever so gently, he placed his thumbs and first fingers on my inner labia, and then stretched them out.
Bang! I orgasmed, moaning and arching my back and the whole works. I don’t think Al quite understood what was happening, because he backed away.
“Oh, ke-ee-ep going,” I semi-yelled, through my shivering, ongoing orgasm. He went right back at it. He must have learned something about girls, because he rubbed my clit with a fingertip, which extended the orgasm even more. I must have been in a continuous orgasm for a minute straight.
The next few minutes are a blank to me. The next thing I know, Cindy and Kelly had moved a coffee table and were laying on a throw rug next to the sofa, They were hugging, kissing, and rolling all around.
Al had produced a rubber and handed the packet to Kelly, who then handed it to Cindy. She was struggling to learn how to put it on Kelly.
I kind of knew where they were going, and seeing them get started was fun to watch. But I wasn’t done yet. I still hadn’t really experienced that penis of Al’s and this seemed like the perfect opportunity. I had him take my place on the sofa, so I was kneeling on the floor. I wrapped my hand around that gorgeous hard penis of his, and then instinct took over. I had to put my tongue on it. Then I sucked the tip and then a couple inches into my mouth, while Al moaned, letting me know how happy he was with the way things were going.
At one point I scraped the side of his penis with my teeth.
“Ouch.”
More carefully, I sucked a bit more of his penis into my mouth. I noticed something. A salty fluid was filling my mouth, and I felt a slight pulsation. Putting two and two together, I realized he had ejaculated.
Al and I collapsed in a heap on the sofa, while Kelly and Cindy collapsed in their own way on the rug. It took us a good half-hour to recover enough to want to start doing something. What I wanted to do was bring the four of us together. I don’t know why, but it seemed right. So, dragging my man by the hand, Al and I joined Kelly and Cindy on the floor. For another half-hour, we hugged in a big, happy group. Nothing sexual, just enjoying being all clumped together. It was true bliss.
“Yikes!” I looked at the clock, and it was quarter after eleven. My parents might come home at any moment. I got us all moving and dressing, and hustled my three best friends out of the house. I watched Al’s taillights turning the corner, just as I saw my parents’ headlights coming in. Close call!
I don’t know if was an unconscious caution, or fear, or something else, but I was still a virgin.
We continued to play pickleball. About a week later, we had a rainy day. I was so disappointed. Summer was almost over, and I didn’t really think life would be nearly as nice without our naked pickleball. We couldn’t waste a single day. I tried to get the others to play out in the rain, but it was just too cold.
Since Cindy’s mom and dad were out of town at some sort of science conference, we had the house to ourselves. We got naked in Cindy’s room, on her big king bed, and had a wonderful time.
It started with show and tell. I had yet to see a guy actually cum. Al had ejaculated in my mouth, and it was wonderful, but I wanted to see a guy masturbate and ejaculate. Don’t ask me why, but it seemed so important I was willing to see Al cum and I knew that meant we probably still wouldn’t have intercourse. He wasn’t so sure, but since he loved me – as he had been saying off and on the past few days, he was willing to fill any request.
He listened to my plea for him to wank in front of us, seemed a bit embarrassed, but at the urging of Cindy and Kelly, he was willing to comply. I figured we would sit around and simply watch Al masturbate. Weird, I know, but that’s what I wanted.
He sat on the edge of the bed. The three of us found random chairs and sat around him in a small semi-circle. He started rubbing his dick, but it wasn’t getting hard. He said it was because he was embarrassed to be seen jerking off. He said it was like what he called ‘bashful kidney.’
“What’s that?” Cindy asked.
Kelly answered, “Sometimes, when a guy has to pee, but other guys, or girls, for that matter, are watching, it is hard to get started.”
“Right.” Al added.
I could relate. Naughtily, I thought of peeing in the school shower. Not in the toilet, but right in the shower, in front of the other girls, as they watched. While the thought made me horny, I thought I might have a little trouble peeing like that.
Cindy offered to help, and Al accepted. I wasn’t so sure I wanted her masturbating my guy, but then, we were, all four of us, the best friends in the world. I decided that jealousy would be ridiculous. She looked at me, asking for permission. I nodded.
She sat next to him on the bed, and placed her hand around his soft penis. She started manipulating the soft puddle up and down, and kept at it a good two minutes, but still, nothing.
Without asking, Kelly stood up, crossed over to the bed, knelt in front of them, and then placed his fingers on Al’s scrotum. He seemed to be gently massaging Al’s balls. I wasn’t sure how Al would take that.
I needn’t have worried. Al went “hmmm” in an appreciative moan, so Kelly continued. Pretty soon, Al was hard as a rock and sticking up within Cindy’s hand, which had taken on a steady up and down rhythm.
Kelly motioned me over, and I took over the ball massaging business. How interesting to feel those soft little eggs in a man’s scrotum. I understand they are sensitive, so I was very gentle. I continued massaging his balls, while Kelly urged him to lean back. Kelly then lifted Al’s legs over his head, which made Cindy’s job difficult. She was a trooper, just leaning back on the bed, and continuing in the new position.
This was very interesting to me. In all our time being nude, I had never really seen anyone’s asshole, or at least not up close. I took a good close look, and loved what I saw. I almost orgasmed even without touching myself seeing Al’s lovely hole. It wasn’t quite what I thought. It was mostly hairless, pink, and had wrinkly radial lines running about an inch from the opening in all directions.
I was curious about Kelly’s plan. It took me only a moment to find out. Kelly spit on his own finger, and then pressed it against Al’s asshole. Suddenly, Al went crazy, squirming all over the place, and had a powerful orgasm.
I missed it! I wanted to see the cum flow out, but I was hypnotized by Kelly’s finger.
Now, I had something new to think about. Fingers in the ass. I wanted that! Kelly hadn’t even placed his finger in Al’s ass. Just on it, but I knew one could go farther than that, and I wanted it!
In the old days – like five weeks ago – I would have been too shy to ask for what I wanted. Hell, I would have been horrified to think of what was happening right here and now. But there’s something about being nude with all your friends day after day that brings out a new kind of power. A boldness.
So, I just came right out and asked. “That finger on the ass business looks delightful. Would someone…”
“Yes!” answered three voices at once.
Somehow it worked out that the first ever finger in my butt was Kelly’s. He had me get on my hands and knees on the bed, so my ass was perfectly exposed up in the air. First, he placed his finger part-way into my vagina, which in itself was really something. He coated it with my copious girl-juice, then placed it against my asshole. I instantly knew why Al orgasmed right away. That’s a most remarkable feeling. Then, he started pressing his finger in a short way. It felt a bit wrong. Almost painful. Then he pulled it out, got more juice on it, and started pressing again.
The pain was gone, and it was just wonderful. As I was enjoying that, Cindy came up behind me and pressed a finger into my vagina. I was about to orgasm, and then she pulled it out, replacing it with two fingers. She curled them forward, so they were massaging what I now know was my G-spot. I started shaking or shivering, almost like as if I was cold. But I was perfectly warm. My knees felt weak, and my head was swimming.
Suddenly an orgasm came upon me like none I’ve ever had before. It came in three waves. It was three nearly continuous orgasms and they just seemed to last for minutes. My knees were so week, it was all I could do to not collapse on the bed. But with Cindy’s two fingers in my puss, and Kelly’s in my butt, I didn’t think I ought to. Soon enough, Cindy pulled out, and I lost it, falling down to the bed, while Kelly stayed with me, keeping his finger well embedded in my anus.
I really noticed that finger in my ass at that point, and lo and behold, I had yet another orgasm. Then, he pulled out. Oddly, he didn’t pull it out suddenly, but instead, very, very slowly, which made it feel like his finger was a foot long.
After a minute I turned around to see my friends, noticing that Kelly’s penis was as hard as I had ever seen it. Then I looked at Al, and he was back in action too, with his penis fully erect again. Neither of the boys were doing anything about it, however.
Now, I’m not great at math, but it seemed to me that neither Cindy nor Kelly had had orgasms yet. So that left two to be satisfied. I felt it was up to me to take care of that.
I decided to start with Cindy, instructing her to take up the same hands and knees position on the bed I had been in.
It was the first time I had really noticed her ass. What a lovely asshole! And it smelled nice too. You’d think that part of anatomy might not smell nice, but evidently it secretes something that smells sweet. Very nice.
I tried pushing my finger into her vagina, but she doesn’t get very wet, so I then stuck it in my own vagina, and got it wet. I then pressed it gently against her ass.
He hadn’t cum yet, and I had the impression boys aren’t satisfied until they ejaculate. Looking at Al to be sure it was OK, I then approached Kelly who was now standing on the floor next to the bed, ungracefully removed his condom, and placed his penis in my mouth. It certainly felt big, but good, and I gave him a blowjob that quickly ended in a strong ejaculation.
Afterward, Al, with his penis as hard as if he hadn’t orgasmed twenty minutes ago, looked at me, and I looked at him, but somehow, we didn’t do anything more. It seemed that Cindy and Kelly were done. We retired to the kitchen where we ate a truckload of snacks, then went outside. The weather had cleared, so we did what we do, we played pickleball!
A few more days passed. It was now a week since my friend had lost her virginity, and yet I was still a virgin. Pretty strange, right? There was also only one week left until college.
Al had remarkably good news. Helped by Cindy’s father, with whom he had been texting for days, he bought a local organic clothing company. So, he was going to be staying in town, not going to away to college and leaving me!
After pickleball that morning, he pulled me aside and asked me whether I’d be willing to go on an official date with him.
“Hell, yes!”
That evening, he pulled up in his beat up old Toyota, said “Hi” to my mom and dad, handed me a bunch of lovely roses, and off we went in his car.
He took me to a semi-fancy restaurant, and we had a nice meal and talked about his new business, my upcoming college, pickleball, and everything but sex. Then, he wanted me to go with him to Cindy’s house. I didn’t know what he was planning, but when we got there, Cindy met us at the door, took us around to the backyard, where near the pickleball court, she had set up a big tent with lots of padding on the ground, and candles burning inside. I considered it very romantic!
Cindy went back inside. Al and I stripped, naturally, and went into the tent. We zipped it shut quickly to avoid mosquitoes. We hugged. We kissed. He pulled out a packet. I knew what it was, and what was expected. I carefully and happily tore it open, pulled out the condom, and unrolled it on Al’s already rock-hard penis. I was a bit slow and clumsy, but got it unrolled on him.
Al didn’t hurry. We kissed and kissed, and hugged together for quite a while. At one point, we were pressed belly to belly, and I felt his penis between us. He shifted downward, and then I felt the tip of his penis against my vagina. How exciting! I was so ready. I had a fleeting thought that I hoped this was going to be as good as I expected.
It was!
Hot!