First time skinny dipping

[Tomvee]

I reconnected with an old friend last week and we got to talking about all of our old stories from back in our high school days.

Jen, The friend I am referring too, brought up a story about how a group of us hopped a fence and skinny dipped at a public pool. I played cool like i had forgotten about but I remember it vividly as did she.

One evening I was sitting at home and got an IM on aol from Jen. The message literally said at my moms drinking and I want to go skinny dipping. Immediately I wanted to be there but had no car. After like an hour I convinced a friend to drive me to Jen’s house.

In typical Jen fashion it was her, one other girl, and an entourage of dudes. Jen was beautiful and I had often fantasized about seeing her naked, but up until this point I never had.

We left the house and walked to a park maybe half a mile from her house. Jen being the ring leader said “I’m going skinny dipping who’s doing this with me?” Jen conservatively hid and undressed and wrapped herself in a towel. Some of the guys went, some sat out being shy.

While climbing the fence Jen’s towel came off completely. Now standing in the pool complex she stood bare naked. Tan allover and with a giant smile. She shielded her tits and pussy playfully then ran over and dove in the pool.

I wanted to follow-suit and skinny dip with her but I got shy something about skinny dipping with mostly guys and having a massive hard-on weirded me out.

Jen’s only girl friend there sat out as she was too shy to get naked. She was enjoying all of the naked guys but too shy to join in. She looked at me smiling asking me if I’m getting naked? Giving me that look like she wanted me too.

While staring me up and down I took my clothes off revealing my massive hard on. After standing naked for a minute Jen did not like that she was not the center of attention.

Jen walked out of the pool and toward the fence giving me a close up of her tan little body. She stared back at me then asked me if I would come swim with her and that it is fun.

Minutes later I had joined in skinny dipping with Jen. We had fun and it was very thrilling. When we left Jen again dropped her towel, probably on purpose, and pleaded for someone to grab it. She got it eventually but we teased her with it and played keep away forcing her to stand in the road completely nude.

[DiegoJames]

Always love these skinny dipping 'first time' stories, as they always remind me of my first time too and the smile it puts on my face 40 years later.

I've been a naturist for 30+ years, so skinny dipping is almost 'routine' now. Indeed, I've not swum without a costume for more than a decade.

I'm going on a naturist holiday in June with a lady friend. She's now 60, looks 20 years younger. A yoga fanatic with a truly hot body! Married, divorced, a string of lovers (hopefully she divulges some of these tales on holiday) and we're co-workers. She's single, I'm not, but we're off on holiday and sharing the same bed.

She's never skinny dipped, never been on a nude beach, despite her many other 'adventures', and she's keen to 'try it all'. She's also happy to be photographed (if I blur, just a little) in various situations.

Of course there's the possibility she'll change her mind but, as much as I know her, she won't. She'll deliver. Rather hoping to create a thread, with photos, when the time comes.

She's equally determined to give her thoughts on these new experience so, as they say, watch this space from mid-June onwards!

[piecenick]

High school senior trip to Destin, FL. We were a small class from a small town, only about 50 or so, the girls outnumbered the guys by about 12. All of the girls were fairly attractive, not all models, but nice. A few teachers went along to keep an eye on us, and they were cool enough to buy the beer since we were all under-aged. In the 60's people were a lot looser about rules, lawyers were not yet ruling the world, the nanny state had not been born.

We are in the old motel on the beach, it is still May so the crowds have not descended, we had the place to ourselves. One of the last nights we decided to gather enough driftwood for a decent bonfire, so we sat around getting drunk on Dixie beer. About midnight, the teachers had all gone in and so had most of the kids, basically just a dozen of the hard core, seven were girls. One of the shy girls, the principals daughter, said she had been skinny dipping once with kids she knew. We found this incredible, she was not the type, so we all doubted her story. She stood up and said if you don't believe her than stand up too, we all stood up. Then she started walking toward the calm gulf water, from behind her top came off, and she shouted if we didn't skinny dip too we were chicken shit.

We all followed her stripping and running into the water. We stayed in the water for a while, but it was cold in the early season, everyone soon went back to the bonfire, but clothes didn't go back on until we put out the fire and went in.

[thegrayprincejt]

My first time was with the wildest of my neices and her best friend when we were in our mid-teens. She decided she wanted to swim in our creek so we were going to go get suits. But she just stripped and dove in. Told us it'd take too long to go get suits. We agreed and joined her. After an hour or so later we all piled out in the sun to dry. Her friend was semi modest but my neice lay spread eagled to "fully dry". But apparently the fact we both kept looking and my.... response to her brazen behavior kept at least one spot from drying.

[ocguy55]

The first time I went skinning dipping was with my college girlfriend at time.

It was the weekend and we were feeling very kinky and wanted to try something extreme.

There was a hotel pool nearby and we snuck into it and took off all our clothes and jumped in. It was hot outside.

I was shaking nervously, but she kissed me to make me feel more comfortable. We had to hide as a couple walked by.

We had never had sex up till that point, but when she took off her pants she revealed the most incredible dark bush which I found strange since she was a blonde.

After that night, we went back to her dorm room and we both decided that the time was right.

[stevezr1]

First time, ONLY time. Skinny dipping was always a major fantasy of mine when younger. I had always imagined a swimming hole type scenario with a girl or mixed group.

When it happened, it was nothing like I ever imagined. I posted this adventure quite a few years ago here.

This was at the Jersey shore, Wildwood to be precise. Summertime, at a nightclub I met a pair of girls from Philly area, I was hitting on one of them, she was rather cute, and somewhat responsive to my advances, but her girlfriend was a real knockout blonde.... killer body, way out of my league. I watched her blow off at least a dozen guys during the night. I spent the latter part of the evening with them, and at closing time, the girl I was hot for suddenly conked out... head on the bar. Her girlfriend was pissed at her, and kept saying, "I told you not to do the whole 'lude!!"

Gentleman that I am, I had to help the knockout blonde literally drag her girlfriend back to the motel and put her to bed! I Figured no way I was going to get laid that night. With my plan now in tatters, I suggested a walk on the beach, and she says "sure, why not". I guess she figured her night was ruined too. It's about 3 AM now, and we're walking along the surf with nobody in sight. It is a very wide beach, and can we could barely see the well lit boardwalk with a heavy mist rolling in. With nothing to lose, I sort of joking suggest skinny dipping. She says "no way, you must be nuts! Anybody could come along and see us"

I'm half heartedly trying to convince her, while scanning the boardwalk for anyone who might see us through the thick mist, and when I turn back, she was completely naked!!! "She says, well, are we going to swim, or what??" What a body! I thought I was in heaven... yep, got laid right there in the surf, and later again back in my motel room, and again when we woke up in AM!
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