Swimming At Aunt Jill's

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
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Trundle
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Re: Swimming At Aunt Jill's

Post by Trundle »

Great to see this back, I think Tommy might be the centre of attention at this beach!
Mattheus
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Re: Swimming At Aunt Jill's

Post by Mattheus »

I really like his aunt
NickTwisp
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Re: Swimming At Aunt Jill's

Post by NickTwisp »

Continuing-------

I was in the middle of a line of beachgoers ordering food, standing there in just my wet white briefs. There were two teenage girls in back of me who definitely noticed this and one of them whispered, "That cute guy in front of us is in his underwear." The other girl laughed and stated, "Perhaps he's underprivileged and can't afford a bathing suit." Then
the person in front of me, a portly middle-aged woman, turned around, stared at my crotch, and said, "Well those briefs sure don't hide much when they're wet." All this attention was starting to get to me, and my penis began pressing against the fabric of the briefs. I was able to use the money bag that Aunt Jill had given me to cover up, that is until it came time to order and pay. The attendant placed all of our food on a large tray which required use of both my hands. I could hear a bit of giggling and a few gasps as I made my way slowly back to our blanket, as I had to be careful not to spill the contents of the tray. Semi erect, my penis was mostly revealed to anyone watching as it pressed against the wet briefs. By this time our section of the beach had become more crowded, so I had quite an audience.

As I approached our blanket, Aunt Jill exclaimed, "Finally, Uncle Fred is very hungry." She seemed oblivious to the fact that I was standing there in wet briefs with a partial erection very visible to anyone looking. The hamburger/fries' lunch tasted delicious, and I was able to cover with my towel to put an end to my embarrassment.

When lunch was finished, to my great relief, Aunt Jill indicated that we were packing up to go home, as she was afraid that Uncle Fred was getting too much sun. But to my great dismay, she grabbed the towel away from me and took another look at me in just my underpants. At least by this time my partial erection had gone away. "How wet are your underpants, Tommy, I don't want you to get saltwater stains on your new Bermuda shorts?" With that she reached her hand over and began feeling around the front of my briefs. I simply could not believe this----my 48-year-old Aunt was touching my penis through my now just damp underwear. After probably a minute of touching my penis, she withdrew her hand. Then Aunt Jill ordered, "Take those off, Tommy, you can wear your Bermuda shorts and t-shirt home without your underwear." By this time, she had grabbed my towel and put it back in her beach bag. "But Aunt Jill," I whined, '"I'll be naked on the beach." In a kind of angry voice, Aunt Jill said, "Stop stalling, Tommy, just stand up and take off those underpants, and I'll hand you the shorts." When my Aunt adopted this kind of domineering tone, I found myself powerless to resist. To my complete mortification, I stood up, lowered my briefs, and thus stood completely naked on a public beach in front of numerous other people. I could hear various gasps and catcalls from others on nearby blankets. "Look, that guy is now bare ass naked," I heard the boy I had previously gone swimming with yell out. Aunt Jill took her sweet old time handing me the shorts to put on as more and more beachgoers took in my nudity. Finally, she handed me the shorts and I put them on.

As we walked back to the parking lot, Aunt Jill stated, "I hope you enjoyed seeing the ocean, Tommy." As we got into Uncle Fred's Pontiac, he laughed and asked, "Should we stop at a store on the back and get Tommy a bathing suit?" In reply, Aunt Jill said, "No, I don't think that will be necessary for the rest of his stay here. The neighbor girls are coming over at 4:00 pm for a swim, and I've also invited the woman next door over for afternoon cocktails. He won't need to wear anything in our pool as the girls saw him naked yesterday and they didn't seem to object." Uncle Fred replied, "Alright, I'll make a pitcher of Gin & Tonics and we call all sit out on the bench by the pool and watch the kids as they swim." Aunt Jill looked thoughtful for a moment, and then mused, "Perhaps I'll call that pleasant older lady from our church and invite her over for a drink. She's all alone since her husband died last year." Laughing, Uncle Fred replied, "Oh, the more the merrier." I slumped down in the back seat of the Pontiac, unhappy at the thought of more naked swimming in their backyard pool.
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Jeepman89
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Re: Swimming At Aunt Jill's

Post by Jeepman89 »

I love that the neighbour girls will be coming over for a swim and Tommy will be bare ass naked. Maybe some other girls can drop by who haven't seen a naked boy before?
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Re: Swimming At Aunt Jill's

Post by extr200 »

Aunt Jill, having raised a son, is one of those women who knows exactly what’s best for her nephew. A wonderful chapter that promises a very entertaining time (with plenty of embarrassing moments) for Tommy! We’re looking forward to it!
Thank you!
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Re: Swimming At Aunt Jill's

Post by NickTwisp »

Story Continues:
====================
Viola Lafferty, age 78, cautiously drove her baby blue 1955 Cadillac over the Mathews Bridge, heading towards the west side of Jacksonville. When she had gotten the mid-afternoon telephone call from her church friend Jill Coles, she had hesitated. Since her husband, Henry, had died suddenly last year, Viola rarely went out, generally just to church on Sundays and the supermarket. Mostly she stayed alone in her large home located in a tony area in the Mandarin section on the east side of the city. The eleven-year-old Caddy still drove along smoothy; Henry had been a stickler for automobile maintenance. The appeal of enjoying afternoon cocktails poolside was tempered by the one odd detail her friend Jill had mentioned---that their visiting teenage nephew would be swimming nude in front of everyone there, including a female neighbor and three girls who lived down the street. Viola thought this rather improper. She had raised two sons and never imagined putting them into a situation like that. True, they had swam naked at the local YMCA, as was the custom back then, but that was in a male only environment. This was acceptable in the 1930s when her sons were teenagers, but far less common now in the mid-1960s. There had been a few incidents where Viola had unintendedly wandered into the poolside area and seen her sons and some of their friends naked for a few moments, until she quickly turned around and walked back out. That had been accidental, but her sons had been very annoyed by the invasion of their privacy at the YMCA. She kind of smiled recalling her sons' naked embarrassment in front of her so many years ago. The more she thought about the past when male nudity in semi-public places was more accepted; it might be kind of entertaining to see a naked teenage boy again after all these years. Nevertheless, Viola vowed to just try her best to mostly ignore the teenage male nudity that was to take place in front of her and the others.

Tommy had laid down in the guest room to take a nap when they arrived back from Jax Beach. Aunt Jill had already described to him what would happen around 4:00 pm, and he was none too happy about it. It had been made clear that he was expected to strip off his clothing, including underpants, and once again swim naked in the backyard pool. This time, not only the three girls would be present, but the woman next door who had apparently spied on him through the fence yesterday and seen him completely bare, would be present. In addition, some older lady from Aunt Jill's church was also invited over. He wanted to refuse but his domineering Aunt was not an easy person to argue with. "Can't I just swim in my underpants like I did at the beach," he plaintively asked? But Aunt Jill had refused that suggestion, saying "Tommy, the girls have already seen you nude and the woman next door said she peeked through the fence yesterday, so all but Mrs. Lafferty have already seen you naked. And Mrs. Lafferty is real old and said she doesn't care." So naked it was going to be, whether Tommy liked it or not. They were all going to see his penis, which he began to almost involuntarily stroke as he laid on the bed. Fortunately, he had closed the bedroom door before his nap. Now he grabbed some tissue from the nightstand, lowered his shorts and underpants to his knees, and proceed to pump his now rock-hard penis. It didn't take long. He usually jacked off every day at home and had not done so since leaving their home in Georgia yesterday. Within minutes he was shooting jets of semen into the Kleenex, the orgasm seemingly more intense as he reflected on his nudity at the pool yesterday and his underwear swimming earlier that day. Somehow the embarrassing sequence of events proved stimulating in an odd sort of way he didn't fully understand. Post orgasm, Tommy quickly wiped up as best he could with even more Kleenex and pulled back up his underpants and Bermuda shorts. He threw the tissues in the wastepaper basket and then fell into a sleep. An hour later, he would be awakened by Aunt Jill entering the bedroom. In a cheery voice, she announced that "Our guests have arrived and it's time for a swim."
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Jeepman89
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Re: Swimming At Aunt Jill's

Post by Jeepman89 »

Let the naked swimming begin! I hope new girls get to see him as well.
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Re: Swimming At Aunt Jill's

Post by TeenFan »

I'm a little disappointed he's already drained the tank.
Will there be enough to allow him to become fully aroused again?
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Jeepman89
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Re: Swimming At Aunt Jill's

Post by Jeepman89 »

He's a young guy so I'm sure he will rise to the occasion again.
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