Skinny Dipping Advice

Hi it’s Jen again. We have a story from a website viewer and she needs some advice, too. Here it is:

“I’m like a 22 year old girl and I live at home still. We have a pool in our backyard which is somewhat covered by trees. There’s one sort of open spot but it’s a pretty private area. My folks go to work all day and when I don’t work during the day, which is like 2 times a week or so since I work on weekends sometimes, I like to head out to the pool and work on my tan.

I’ll start out on my back and then flip over while wearing my bikini. When I’m on my stomach, I’ll unhook my top. After that, I’ll flip over and leave my top off since the area is really private. I hate tan lines on my big boobs that actually barely fit into my bikini top.

Then, to cool off, I’ll jump into the pool topless. Pretty soon my bottoms come off and then I skinny dip a bit before I go and float in the pool on this sort of air mattress chair thing and catch the sun like that – totally naked during the day. Once I lost my bikini bottoms somehow but that’s another story.

Well, I was doing that kind of thing one day and I looked up and around and there was this guy staring at me. He was in the one sort of area that isn’t covered up. It’s sort of facing this area with trees farther off, so it still is pretty private. I must have screamed a little or something as I tipped the chair over and got into the water so that I was more covered up by the water at least. I found my bottoms and then looked around again and he was gone.

The next day, I was out there again and there was no sign of him but I’m wondering what to do. I don’t feel as safe now as I used to. I still want to tan and skinny dip and stuff but I keep picturing him staring at me and now can’t enjoy it. Any advice?”

Thanks again for the letter and our fans thank you for describing your big boobs to us – at least Eric liked that part. He wants a picture of them, he said and wants to know if you also wear a thong. Ha!

What I would suggest is going a week or so and be covered up. Don’t go topless or anything and keep an eye on that area where he was. He’s probably not going to come back if you screamed a little (that was a good thing to do). So if he’s not back this next week then you’re probably pretty safe to try it again.

What does everyone else think?



  1. Hmmm… no date on these posts, but given this is second from the bottom on page 19 or 20 (as of 20 FEB 2021!), I suspect this has been posted for a while.

    Well, I think Jen’s suggestion is pretty good. I would encourage the reader to follow that suggestion or do whatever is necessary to NOT give up her love of skinny dipping!

    But, even more importantly – we wanna know what she decided!

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