Jimmy Learns a Lesson About Teasing by MaxTwilight,MaxTwilight

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All characters in this story are over the age of 18, the situations in this story are entirely fictional and creations of the author, and any resemblance of characters to existing persons living or dead is purely coincidental.

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My name is Jimmy. When I was a young man of twenty-five, I lived and worked near the emerald coast of Florida. My parents lived in Ohio but owned a small beach condominium in Fort Walton they used in the winter. I could use it any other time of year and would routinely drive an hour to spend my weekends on the beach. The night life around the Fort Walton beach was great. There were a lot of nightclubs, white sands, and crystal-clear water. In the summer, there were also lots of women on the beach who were out to see and be seen. It was my paradise.

Even though I had a desk job during the week, I found time to work out. After all, if I was going to be at the beach, I had to stay in reasonable shape. I liked to walk along the shore in the mid-morning when it was not too crowded and lay out my towel somewhere meticulously while I scanned the beach for interesting women. It was always a mixture of people. Sometimes there were older couples on a weekend in the sun, sometimes families on vacation and sometimes young folks like me playing volleyball or lounging in the sun. I had some local friends, but mostly this was “me” time.

I had a special “kink” that I secretly enjoyed. If I found a nice-looking group of women lounging and looking out to the ocean, I would try to lay out my towel directly in their field of vision but closer to the shore where they could see me easily. I would arrive dressed in shorts, and a t-shirt with my swimtrunks under my shorts. I would do a little “strip” down to my trunks, being sure to flex a little and show off the nice chest and abs on my slim five-foot nine-inch frame. It was not too obvious, but I hoped to glance up and see if any of the women were checking me out. Even if I could not tell where their eyes were looking behind their sunglasses, I imagined they were staring at me.

One summer I spent a couple of weeks on vacation at the condo. On a Monday morning, I spotted a group of women, probably in their mid-thirties to forties. It was typical to see women at that age who were old friends and had moved apart, but on a “girl’s reunion” vacation. There were six of them, in a semi-circle chatting and enjoying the ocean view.

I could not resist. I laid out my towel in full view near the shore. I thought I heard them go a little quieter as I started to undo my shorts. Earlier, I purposefully left the draw string of my trunks untied so I could “accidentally” inch them lower when I pushed my shorts from my hips.

I pretended not to realize my trunks were dangerously low on my hips while I pulled my t-shirt over my head. I even pretended to get caught in the t-shirt to prolong the moment. If any of the women looked, they would have time to imagine my trunks sliding more.

When I got the t-shirt off, I looked up and down the beach as though embarrassed that someone might have seen. Then I tugged up my trunks quickly and tied the drawstring. I glanced over and saw a few of the womens’ heads turned my way. So much fun!

It turns out this group must have planned a week for their reunion, because I went out a couple more days and saw them there. I got to enjoy pretending their eyes on me each time. One time when I thought they might notice me, I went into the water and let my trunks slip again just enough to be interesting and emerged that way. Then, of course, I pulled them back up.

I hoped the women noticed me because I was taking more notice of them. Even though they were older than me, they had certainly stayed hot looking. A few of them could really rock a bikini.

When Friday came around, I noticed the same group of women, but there was another gal who had joined in. She was dazzling. I could not help noticing her and do a little gawking myself. Unlike the other women who were generally beautiful, she was, in a word, “built”. She was about five-foot-ten-inches tall, had neck length thick wavy dirty blonde hair and was unmistakably a gymnast or bodybuilder. She wore short white shorts that showed off her thick thighs and a pink bikini top showing off her firm B cup breasts, muscular back and arms. All I could think when I saw her there was “wow”. It made me feel almost intimidated to do any kind of tease routine when I saw her. On the other hand, it gave me an added thrill thinking she might look. I got semi-hard just thinking about her watching me. I turned toward the ocean, and unzipped my khakis. Then I pulled my t-shirt off while I shimmied out of of my khakis down to my swim trunks grinning to myself. Nothing too obvious.

After I laid down on my towel, I could hear the chatter of the women and a good bit of giggling. Then it went silent.

You can imagine my surprise when I looked up and saw the muscle gal standing above me! When I looked up and over my sunglasses she said, “Hi. I’m Brenda.”

After getting over a little shock, of course I said, “Hi” and stammered for what else I might say to this beauty.

She said boldly, “Hey, do you mind if I join you?”

I wanted to find out more about Brenda and with a smile said, “Sure thing.” She sat down lotus style in the sand next to me. I just stayed laid out squinting in the sun to see if her eyes were looking me over while we chatted.

When I craned my neck around to glance up at the other women, I saw they were all looking on curiously, but Brenda said, “oh, don’t mind my friends, they’ll get along fine without me.”

Brenda went on to tell me she was there for the weekend from South Carolina and that she and the other women were old high school friends now living various places. Brenda appeared to be in her mid-thirties. I wasn’t surprised at all when she said she worked at a gym. We spent about twenty minutes or more chatting.

At one point looking down at me, she said, “You know, you are really cute. I think the other girls think so too. They’ve been watching you”

I blushed at that, but just said, “oh, that’s ok. I come here most mornings for “me” time.”

She said, “Maybe you would like to join us later. We’re having a party at the beach house they rented. It’s the one just up there.” She pointed. I recognized the place. “You could be my plus one. The other girls have been here all week and have dates already.” She said it with such a big smile, I could not turn down the invitation. She said, “It’s casual like everything here, come just like you are, around eight.”

I said I would be there.

Later that evening…..

I wasn’t surprised when Brenda answered the door. She was dressed in a red pair of short shorts and a tight sleeveless low-cut t-shirt that really showed off her upper body strength. I was impressed. There must have been about thirty people there at the party. It was a mix of locals and fun time vacationers in their twenties to forties. Brenda led me in but didn’t introduce me around. She knew only a few of the people apart from her old school friends. That was fine with me because I really wanted to get to know Brenda better. She did introduce me to Margo, a slim dark-haired beauty who had a deep and sultry voice and was wearing a killer black dress holding C cups and was the unofficial leader of the group. I recognized her from earlier on the beach.

There was no shortage of beer, wine, and mixes. I wasn’t a big conversationalist, but the music was loud, and had a beat so there was some dancing. I liked seeing Brenda move to it, as well as the other women.

As it got late, most of the guests left, peeling off to go to the late nightclubs or whatever else they had planned. Three of Brenda’s six school friends also left. The other three, who probably had too much to drink already, were the only ones that stayed behind. Margo was one of them. Stacey and Kylie, also reunion friends, stayed behind. They were light brunettes with fuller figures but sexy all the same. They might have been into one another, but I wasn’t sure.

I was sitting on the couch with Brenda with her arm around my waist when she said to the others, “What do you think of my date ladies?” Stacey and Kylie were sitting in chairs facing us across the center table.

Margo spoke up from the kitchen behind us, “Brenda, you know we’ve had an eye on Jimmy all week.” The other girls giggled over their drinks.

Stacey, who obviously had a few un-inhibiting drinks joined in, “Yeah, we like that little dance he does every morning on the beach.” The others burst out laughing.

When my face went totally red, Brenda said softly “Don’t blush baby, we’re just having fun with you.” I could feel her firmly pull me closer on the couch.

Margo was feeling good swaying to the music in a dreamy state but called over, “I hope we see more of you on the beach Jimmy,” and added, “No need to be shy around us now.”

In defense of myself I said, “Don’t worry Margo. I’ll come join you if I see you’re out there.”

Brenda was getting a very mischievous smile and wasn’t shy at all about looking me up and down. Then she said “Honey, I think we’d all like to see more of you, don’t you think ladies?” And, to my surprise, she lifted my t-shirt playfully flashing my abs to Kylie and Stacey.

Stacey and Kylie’s eyes went wide, and they burst out laughing. Kylie blurted out “Oh yeah, Jimmy, let’s see MORE of you.”

This was getting a little strange and I thought about excusing myself politely for the night and I made a barely noticeable effort to get up. My butt was deep in the couch and without leverage it didn’t budge. Brenda’s arm around my waist held me there imperceptibly and effortlessly.

Brenda looked at me and said, “Jimmy, you know you really shouldn’t be shy. After all, Kylie and Stacy have seen your chest already when you’re sunning on the beach.” Brenda’s hands clutched the bottom of my t-shirt in front and back and tugged it out of my shorts. Before I knew it, she had it over my head with arms twisted up in it! She tugged it all the way up and off and dropped it behind the couch out of reach. I blushed a serious shade of red.

Stacey chirped, “Oooo! Nice chest Jimmy!” She and Kylie giggled in delight.

Brenda’s arm quickly snaked back around my bare waist. She completed the move with a playful pinch of my bare abs implying a message of control. (Who was I kidding, of course she was in control!)

Margo could tell something was up and came sauntering over still swaying to the music, holding her drink and making the observation, “Oh, looks like we’re getting comfortable,” and she giggle too.

I laughed with them not wanting to look frazzled. I figured they’d think they had their fun if I didn’t make a big deal of just being top stripped! Brenda kept that strong grip around my waist. I think she sensed I almost tried to get up before.

Brenda wasn’t done goading her friends on and said to me, “Jimmy, Margo was telling me that you make it a habit of teasing them on the beach, is that true?” She bit her lip like she had caught me in something naughty.

The girls gleefully joined in, “Oh yes. Yes, he does!”

Margo added, “Yeah. It’s quite annoying, hmmm sexy, but annoying. Don’t you think girls?”

Stacey agreed chiming in, “Oh, I’ll say. Sometimes I think he should just take it ALL off and give us a real show!”

This was getting out of hand, but realizing how I had caught their attention on the beach excited me and started to give me an erection. I tried to get up this time for real, but Brenda tugged me back quickly saying, “Oh baby, don’t go. This is just getting fun!”

I stammered something about “What’s fun is fun.” Again, I tried to laugh it off with them.

But Stacey pushed it further and said in a matter-of-fact tone, “I really think Jimmy should be punished for all that teasing.” She made a gesture to Brenda, slapping the bottom of her beer bottle with her bare hand and smiling wickedly.

Brenda caught on immediately. “Oh, you are so right Stacey!”

Before I knew it, Brenda had pulled me over her lap with my face over the end of the couch! “Hey! I called out. “What the…..”

Brenda shot back, “Jimmy, you really need to make it up to them. I think five whacks should do it.” And she proceeded to administer five quick smacks on my bottom! They stung!

I exclaimed, “Owwww! Hey!!!”

Margo almost doubled over laughing but straightened up enough to say mercifully “Jimmy are you ok?” I could see her snickering even as she said it. The other girls looked beyond gleeful at my predicament.

Brenda had easily pulled me over with one hand, the same one she used to swat me. Her other hand was underneath me right at my crotch where, to my embarrassment, she learned my secret desire for exposure because she could feel my erection starting. I didn’t want it to happen, but I couldn’t help it!

Brenda leaned over to my ear, pinning me with her upper body and whispered, “Baby, I think you like this.” Her hand gently gripped at the swelling in my trunks a couple times to let me know she knew. She added “I think somebody likes giving a little sexy show. Hmmm?” I was blushing so badly, and the blood was rushing to both heads!

Brenda then wiggled the hand she had under me to the unsnap the top of my shorts! With the other hand on my lower back, she kept me pinned down to her lap. She had strength.

All I could do was feign an objection, “Brenda! Let me up!” But my erection betrayed me. The thought of Brenda exposing me to these girls was arousing. Kylie rushed over to where my legs were almost off the couch grabbed my ankles and pulled my legs firmly up on the couch and sat on the back of them! I was now hopelessly pinned!

Margo perked up again, “Jimmy, you look so cute with your tushy up like that. But you know we’ve enjoyed seeing you show it off in your swim trunks.”

It didn’t take Kylie any time to get the hint and she reached over and started to tug my shorts off and down to my thighs. I still had my swim trunks on under my shorts and she exclaimed, “There they are! Those are the trunks!”

Stacey was now blushing behind her beer but looked on intently, while Kylie wrestled my shorts down to my feet and off! She threw them over her shoulder, and I could hear them hit the wall.

I thought to myself… (There, they’ve had their fun. I’m sure Brenda will let me up and we’ll all have a good laugh and another beer.) I was hoping my erection tenting my boxer briefs between Brenda’s legs would subside.

Then I heard Stacey start to hum something behind her beer glass, “Da da da… da da da da,” sounding like a lounge strip song. All the girls burst out laughing.

Brenda leaned over again to my ear. “Don’t you think you can give us all a real show baby, hmmm?”

Margo was totally enthralled as she stood there looking on thinking…. (Oh my, Brenda has him just where she wants him. It’s where we all want him! I hope she does it. I hope she pulls those little trunks right down so we can see his cute little ass!)

As I laid there trapped, I thought maybe if I got a little more insistent, I could get out of this and said, “Brenda, Let me up! I think you girls have had enough fun!”

Then I heard all the girls almost in unison chant, “Oh boooooo! Booooo!”

Kylie stoked the fire, “No way Jimmy. We deserve a show. We want a show.”

All the girls started to chant “We want a show! We want a show! We want a show!”

Brenda somehow found the drawstring of my swimtrunks. As she pulled on the end, the knot untied. Seconds later, everyone could see the drawstring in the grasp of her fist pulling it out from under me.

Stacy screamed, “Whoah! Go Brenda!”

Brenda kept pulling it slowly until it came completely out! She said so calmly, “Oh this is so untidy.” Flicking the string away. Then she leaned over again to my ear giggling, “Jimmy, I think that was all that was holding up your little trunks.”

Kylie reached forward again and started to tug on the bottom of my trunks!! I looked back at her and shouted, “No way!!! Don’t you dare!!!” But I could feel my trunks inch down my hips. I tried to reach back to grab them.

Brenda had anticipated my move and stretched her arm under my right arm, and over my neck and gripped my left arm in a wrestling hold.

Margo looked on thinking to herself, “omg, Kylie is doing it!” Then without realizing it she let out a sultry, “oh yeah baby show us some skiiiiiin,” singing the last word.

Kylie made a series of little tugs I was helpless to stop and then gave a firm tug to exposed my butt completely.

The girls roared, “Whoah! Yessss!!!!”

Brenda leaned over while knowlingly clutching my erection underneath. “Oh yes honey, you like to show off. Yes. Oh yes you do! Now, turn over for the girls.”

At this point, I was so turned on and there was no getting out of this anyway. I couldn’t believe I was about to be naked in front of these four cheering women. I turned over willingly in Brenda’s lap and exposed my totally tented trunks which were only pulled down in front to my shaft. Stacey let out a gasp seeing the obvious.

Brenda put her hand to my waist grasping the top of my trunks and playfully pulled them away from my abdomen so she could peek inside stating the fact, “Oh Yes. You want this, Jimmy.” She pulled my trunks up and over my rigid member and pushed them to my thighs. Then she returned to grasp my throbbing shaft commandingly letting her thumb press into the swollen slit. I couldn’t help but let out a grown of ecstasy. Kylie pulled my trunks down and off, throwing them aside.

Margo did a twirl to the music and exclaimed “Whooo hooo!!

I was helpless but loving it all. Brenda held me close to her with her arms around me and her breasts pressed to my back on the sofa as she started to stroke my shaft in full view of everyone.

Kylie got off my legs and revisited Stacey to put her arms around her as they contentedly watch the show.

Margo looked on still standing and swaying to the music with her drink and her eyes dazzlingly fixed on the action.

Brenda softly spoke in my ear so the others wouldn’t hear as she stroked for all to see. “Now baby, just how many other women have you been teasing on that beach down there?” She went on, “I bet it’s been a lot. Don’t you think they all deserve a show, Jimmy? What do you say? Should I lock you out naked on the balcony with the lights on?”

My body betrayed my excitement. I couldn’t hold on any longer and she knew it. I came forcefully with my cum spurting a few feet in the air! Kylie and Stacey were kissing, laughing, and watching it all.

Margo started to applaud. “Way to go Brenda!!”

After Brenda emptied me stroking sensually. Kylie and Stacey got a towel and cleaned up my splattered legs, but not without massaging them in appreciation. Margo meanwhile picked up my swimtrunks and twirled them around on her finger like a trophy.

After a moment, Brenda said for all to hear, “Now baby, just remember what could happen to a little tease like you when a real woman gets hold of you. I’ll let you walk home with your trunks this time but don’t let us catch you prancing around on the beach again in front of other women or you’ll really pay the price.” She motioned to Margo who dropped the trunks into her hand. Brenda dangled them up above my face with the hand that wasn’t still grabbing my shaft.

I was totally drained. Brenda pulled me up announcing it was time for me to go. Margo, Kylie, and Stacey all applauded the performance. I was still in a daze.

Brenda then said softly, “I’ll bring your clothes to the beach tomorrow. But have a nice walk back to your condo.” She escorted me to the door held my naked body close to her. She handed me my stringless swimtrunks and gave me a powerful kiss saying softly, “See you on the beach tomorrow.” She gave me a knowing wink and with that she gently placed two fingers on my chest, prodded me out and closed the door.

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