It Finally Happened!

Alanna sent in this great story of her very first time, even if it didn’t exactly go according to the well-thought out plan!

So, I had wanted to go skinny dipping for a really, really long time. Reading all the stories on here and other places online really opened my eyes to how much fun it can be. So when a chance to do it came along, I decided to seize that moment! It didn’t happen the way I planned, but it happened all the same.

My friend was going to have a sleepover with me and a few other friends, and we almost always go swimming in her pool, so I was sure that this would be the perfect place to do it. Before leaving home, I intentionally took out my bikini and left it in a cabinet, so I couldn’t turn back.

We got to the house, hung out for a while, and eventually we decided to go for a swim. I started getting super excited and nervous at the same time. Is this going to work? Would they think I’m super weird for trying? The plan was: when we all split up to different bathrooms to get changed, I would just get naked and simply start walking to the pool like it was no big deal.

So I got into the bathroom, took off all my clothes, put my handle on the doorknob, and….suddenly it felt like a very big deal to me. None of my friends had ever seen me naked, what if it was too big of a shock? Or what if they got the wrong idea? Or what if my body is actually super weird and I never knew? At that point, I would have just put my swimsuit on and forgotten the whole thing, but I had left it behind on purpose, so I had few other options.

As I was about to just give up, put my clothes back on, and go watch my friends have fun in the pool without me, one of my friends, Sara, swung open the door to the bathroom, barged in, and caught me standing there in all my naked glory. I think I screamed a little bit, and she started stammering “oh my God, I’m so sorry, the door wasn’t locked, my bad” and started to leave. But, thinking fast, I blurted something like “acshlycanuhlpmeplzifrgotmysuit” and she was just like “Huh?” as she was halfway out the door. So I said, somewhat more coherently, “Just come in here” and she did.

And there it was, ice broken, first hurdle overcome, I was standing totally naked in front of somebody else. I tried to play it off like I was totally cool and comfortable, but I was super red in the face and awkward, and I’m sure she noticed. “I, uh…forgot my suit, not sure what to do” I started to say, while Sara had unbuttoned her jeans and started pulling them off. I started freaking out in my head, but I had to just keep thinking to myself “it’s okay, it’s okay, people change in front of each other all the time, it’s no big deal.”

Her shirt was coming off by the time she said “well, you could just ask around if anybody has a spare.” Such a simple solution, but the rush of being seen naked compelled me to decide that there was no turning back. I was going skinny dipping. Today. But I’m still awkward, so I meekly replied “I dunno, I don’t want to have to put all my clothes back on” which Sara must have interpreted as me asking her to go check for me, because she replied “OK, I can check.” In retrospect, I should have just clarified and said “no, it’s fine, I’ll just go naked,” but I think I was too distracted by the fact that Sara had just taken off her last bit of clothing.

I think I was just surprised, actually. Her boobs were a lot smaller than I expected, but her butt was much more shapely. I tried not to stare, still pretending to be cool with the whole thing, but I couldn’t help but try and get a good look at her.

Then she put on her swimsuit and left the bathroom, I almost forgot to say thanks for checking. Then I just waited for a little bit while Sara checked around, regretting all the decisions I had made. I easily could have just put my clothes on and went to check for myself in this amount of time, so Sara probably thinks this is super weird that she has to check for me.

After a little while, she came back with a bikini in hand. It was one of Kelly’s old ones, the girl whose house it was. She told me that it might be too small, but it was the only thing they could find, and watched me try it on to see if it fit.

I was kinda hoping it wouldn’t fit, I was getting too far from my goal, but Sara put in all the effort to find it and I felt bad, so I made it work. But it definitely was too small, I could barely get the bottoms over my butt, and the top totally pancaked my boobs, it was so tight. Sara laughed a bit and just said “good enough?” and I just said “sure,” kinda defeated.

We made our way out to the pool, everyone having a good laugh at how tight the bikini was. I felt so uncomfortable, both because of how the thing I was wearing felt and how stupid it probably made me look. We hung out in the pool for a while, and after the eighteenth time trying to adjust my top to fit correctly, I finally decided that enough was enough, back to plan A.

I started pulling it off, struggling a little, because of how tight it was, to which Kelly asked “are you trying to take that off?” and I said “yeah, I’m sorry, it’s just so uncomfortable.” She had brought attention to me. Everybody was watching me now. I managed to get it off and threw it out of the pool, which got a confident “WOOO” from everyone else, which gave me just the confidence I needed to take my bottoms off and fling them out of the pool too. This got me a bigger “WOOOOOO” and I replied with a little naked dance, haha.

I finally did it, and I couldn’t really believe it. Part of me was super embarrassed, regretting everything about it, but another part entirely was proud of myself for finally just doing it. All the other girls were being super nice and complimenting me until I pretended to be comfortable.

And then of course, after a while it felt like no big deal, I was just the naked one. Nobody else got naked, unfortunately, but a little later on when we were sunbathing, a couple girls actually tanned their butts a little bit, which they had never done before. I felt super proud for opening up that possibility.

After spending the day in the sun, everybody went inside and changed into their PJ’s for the rest of the night. I kinda wish I had “forgotten” those too, but that would probably have been pushing it.

And now I get to look forward to maybe going skinny dipping with them again! Maybe being a little bit less awkward about it next time, hahaha.

That’s great, Alanna! It really doesn’t matter how it happens, as long as it happens!

-Jen