Swimming At Aunt Jill's

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

Post by NickTwisp »

This story is fictional, however, it is based upon an actual series of events. Location is Jacksonville, Florida, July, 1966.
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When I was 15-years-old my parents had to attend an out of state business conference for five days. I was an only child and they felt that I was too young to stay home that long by myself. Mom's sister, my Aunt Jill and her husband Fred lived in Jacksonville which was about a three hour drive from our home in Georgia. They had one son, age 19, who was away on a college internship that summer.

Mom drove me to their house one morning and we arrived about noon. I had packed a small suitcase for my stay there but had not bothered to put in my swim trunks, since they did not have a pool the last time I was there, about three years prior. This turned out to be a major mistake on my part, and the source of much subsequent embarrassment.

As Aunt Jill prepared lunch, I noticed out the kitchen window that there was now a fairly large above ground pool, complete with access ladder at the far end of their rather large backyard. Aunt Jill noticed me looking out the window and stated, 'Yes,we put that in last year. Tommy, you will have lots of fun swimming while you are here." Mom then chimed in, "Oh, too bad he didn't pack his bathing suit." Aunt Jill replied, "No matter, he can swim without a bathing suit. There is a privacy fence between our yard and the neighbor's house. I'll give him a beach towel to walk down to the pool area and it will be fine...no one will see him." My mother then began to giggle and said, "Oh, he won't do that. Tommy is very modest. I accidentally walked into the bathroom last week when he was exiting the shower. I saw him completely naked and he was very upset." Jill just laughed and said that it shouldn't matter if a Mom sees her teenage son naked. In actuality, I had been so stunned the prior week when Mom walked in that I had sort of frozen and just stood there for a few moments, giving Mom a prolonged look at my privates. Aunt Jil then asked Mom if she thought my development 'in that area' was normal. Mom then described what she had seen and noted that she thought 'it would be larger' at my age. At this point, I was very uncomfortable that the lunchtime conversation had somehow devolved into a discussion of my private parts.

After lunch, Mom departed and Uncle Fred left for work. Aunt Jill told me to go to the guest room (where I would be staying) and take off all my clothes. She said she would bring me a beach towel that I could wrap around me for the walk down the yard to the pool. I tried to say that I didn't really feel like swimming but Aunt Jill took on a kind of authoritarian tone and I could tell that I really had no choice. I proceeded to the bedroom and took off everything but my white briefs. Suddenly Aunt Jill opened the door and walked in. I felt very embarrassed to have my Aunt seeing me in just my underpants, however, this gave me an idea. I made the suggestion that I could just swim in my underpants instead of nude. That idea was swiftly rejected. "No one will be around, Tommy, and I will be in the kitchen baking cookies this afternoon for next week's Womans' Club Luncheon, so there is no sense in getting your underpants wet and full of chlorine," my Aunt replied.So very reluctantly, as my Aunt watched, I carefully wrapped the beach towel around me and slid my underpants down my legs and off. Wearing just the towel, I followed my Aunt back to the kitchen and then walked out the back door. It felt really strange to be out in a yard, with houses on either side, in just a towel. The so-called privacy fence between the yards on either side was only about four feet tall, so any relatively tall person could have seen over it. Moreover, the fence was not solid wood; it consisted of slats about 3 inches apart.

About 10 feet away from the pool was a large picnic table with benches. In order to get into the rather tall above ground pool it was necessary to climb an attached ladder, requiring the use of both arms and hands. So I was going to have to leave the towel on the picnic table and then do a naked dash to the pool, climb the ladder, and get in the pool. I silently prayed that no neighbor was watching or seeing through the fence, then took off the towel, and I was stark naked in my Aunt's backyard. Quickly I ran for the ladder, grabbed on with both hands, and plunged into the pool.

For the next half hour or so I actually enjoyed the feeling of swimming around nude in the pool. It certainly was a different sensation than wearing a bathing suit. Suddenly things took a turn for the worse as I heard my Aunt Jill approach the picnic table accompanied by three girls. Two of them appeared to be teenagers and one looked much younger. In a cheery voice, Aunt Jill stated, "Tommy, these are the neighbor girls from down the street. They've come over for an afternoon swim on this warm summer's day." Turns out they were Cindy, 16, Gail, 14, and their little sister Marci, 9. Awkwardly, I leaned over the above ground pool edge and introductions were made. At this point all anyone could see was my upper chest. In a kind of panicked voice, I said, "Aunt Jill, they can't swim with me now, I'm not wearing a bathing suit." At this the two older girls giggled and their 9-year-old sister gave a small gasp. I figured that Aunt Jill would send them away; perhaps she had forgotten that I didn't have a bathing suit on.

Instead, Aunt Jill turned to the girls and asked, "Do any of you mind if Tommy is not wearing anything in the pool?" All three rather eagerly confirmed that this situation was fine with them. Gail then remarked that she had never seen a boy near her age naked before, but felt that it would be "alright" if she now did. Cindy stated (with a kind of giggle) that she was certain their mother would not mind since "he's just the visiting nephew." The two older girls, wearing modest one piece swimsuits, approached the pool and unhesitatingly climbed the ladder. Marcie kind of hung back with Aunt Jill, who sort of had a half-grin on her face. Aunt Jill then said to Marcie, "Why don't you come back to the kitchen with me and help me finish baking cookies? You might be a bit too young to be seeing my nephew without any clothes on." Looking slightly disappointed, Marcie followed Jill back to the house. Aunt Jill briefly turned back and stated, "You all have fun now, I will bring out some lemonade and freshly baked cookies in a little while."

I was some combination of stunned and very embarrassed at this point. Just unbelievable that my Aunt would leave me naked in her pool with two girls around my age. Cindy and Gail splashed around the pool while I just stood there with my hand over my crotch. Cindy eventually said to me, "Why don't you stop worrying about your modesty and just swim with us?" I knew she was right---I couldn't just stand there all afternoon with my hands over my privates. Very reluctantly, I uncovered my crotch. In the clear pool water both girls could easily see my penis. It felt almost dreamlike to be in this situation, naked and exposed. The only saving grace would be that these weren't girls I would see in school or probably ever again once my stay at Aunt Jill's was over. So I accepted my fate and we began to swim and then toss around the rubber pool ball that was there.

About 45 minutes later Aunt Jill walked down the yard with a plate of cookies she had just baked along with some fruit punch. She placed the refreshments on the picnic table and beckoned us to exit the pool and enjoy the snack. Of course the girls had seen my full nudity in the water but it seemed much worse to have to climb out of the pool using the ladder and then get over to the picnic table where my towel was laying. In addition, my Aunt would now see her nephew full frontally nude, at least until I could reach my towel. I asked my Aunt if she could bring the towel over to the pool railing, but the response was "Don't be silly, Tommy, I'm your Aunt and there is no need to be so modest around me." Having no real choice, I climbed the ladder as the girls and Aunt Jill stared at my nude form. Now I was naked in front of my Aunt. As I approached the table, I quickly grabbed the towel and wrapped it around myself. As I sat on the bench with the towel around me, I felt a strange mixture of embarrassment and arousal at what had just happened. My penis began to become erect under the towel as we all sat there and ate the cookies and drank the punch. Soon I had a full-fledged boner. What was I going to do when it was time to go back in the pool? The only solution I could think of was to decline to swim anymore that day. But would my somewhat domineering Aunt accept that outcome? The alternative, allowing my Aunt and the two girls to see me with a fully stiff penis was not what I wanted to occur.
Last edited by NickTwisp on Tue Feb 25, 2025 1:28 am, edited 1 time in total.
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Jeepman89
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Re: Swimming At Aunt Jill's

Post by Jeepman89 »

Love this story, Nick. Let's hope Tommy is a normal 15 year old boy and is a grower with a good sized penis for the girls to ogle.
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Re: Swimming At Aunt Jill's

Post by steam train »

NickTwisp wrote: Sun Feb 23, 2025 11:39 pm ….. Aunt Jill then said to Marcie, "Why don't you come back to the kitchen with me and help me finish baking cookies? You might be a bit too young to be seeing my nephew without any clothes on." Looking slightly disappointed, Marcie followed Jill back to the house.

I was some combination of stunned and very embarrassed at this point. Just unbelievable that my Aunt would leave me naked in her pool with two girls around my age. Cindy and Gail splashed around the pool while I just stood there with my hand over my crotch. Marcie eventually said to me, "Why don't you stop worrying about your modesty and just swim with us?" I knew she was right---I couldn't just stand there all afternoon with my hands over my privates. Very reluctantly, I uncovered my crotch. In the clear pool water both girls could easily see my penis.
Is Marcie in the 2nd quote above meant to be one of the two older sisters as Marcie went inside with the aunt.

Enjoyable read, thank you for taking the time to write and post.
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Re: Swimming At Aunt Jill's

Post by Pluto2025 »

Thanks for this enjoyable story.
Who wants to see the boy naked more, the girls or his aunt? I think the aunt is even more curious, no matter how hard she tries to hide it.
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Re: Swimming At Aunt Jill's

Post by Jeepman89 »

Steam Train, Marcie is the little sister, aged 9, actually according to the story.
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Re: Swimming At Aunt Jill's

Post by IdentityUnknown »

Jeepman89 wrote: Mon Feb 24, 2025 1:04 pm Steam Train, Marcie is the little sister, aged 9, actually according to the story.
I believe steam train was asking if that second line was said by someone else and mislabeled as being said by Marcie since Marcie had gone inside with Aunt Jill.
My True Story: viewtopic.php?t=4978

The Fictionalized Version: viewtopic.php?t=5014
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Re: Swimming At Aunt Jill's

Post by docknumber »

NickTwisp wrote: Sun Feb 23, 2025 11:39 pm.

As Aunt Jill prepared lunch, I noticed out the kitchen window that there was now a fairly large above ground pool, complete with access ladder at the far end of their rather large backyard. Aunt Jill noticed me looking out the window and stated, 'Yes,we put that in last year. Tommy, you will have lots of fun swimming while you are here." Mom then chimed in, "Oh, too bad he didn't pack his bathing suit." Aunt Jill replied, "No matter, he can swim without a bathing suit. There is a privacy fence between our yard and the neighbor's house. I'll give him a beach towel to walk down to the pool area and it will be fine...no one will see him." My mother then began to giggle and said, "Oh, he won't do that. Tommy is very modest. I accidentally walked into the bathroom last week when he was exiting the shower. I saw him completely naked and he was very upset." Jill just laughed and said that it shouldn't matter if a Mom sees her teenage son naked.
I have a feeling that Tommy’s mom and Aunt Jill planned everything so that Tommy has to swim nude. Tom’s mom might have known her sister has a pool now and didn’t let Tom knew this so that he will not pack his swim shorts.


Or it might be pure coincidence ;)
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Re: Swimming At Aunt Jill's

Post by NudeBaG »

Another amazing story in the works!
Can’t wait for the girls to see that boner😈
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Re: Swimming At Aunt Jill's

Post by steam train »

IdentityUnknown wrote: Mon Feb 24, 2025 3:11 pm
Jeepman89 wrote: Mon Feb 24, 2025 1:04 pm Steam Train, Marcie is the little sister, aged 9, actually according to the story.
I believe steam train was asking if that second line was said by someone else and mislabeled as being said by Marcie since Marcie had gone inside with Aunt Jill.
Correct 👍
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Re: Swimming At Aunt Jill's

Post by steam train »

Jeepman89 wrote: Mon Feb 24, 2025 1:04 pm Steam Train, Marcie is the little sister, aged 9, actually according to the story.
What I was asking is if that second line was said by someone else and mislabeled in the story as being said by Marcie since Marcie had gone inside with Aunt Jill.
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