One of my missed opportunities was a friend's sister and one of her girlfriends. I was around 20 at the time, and my friend's sister was 18. My buddy and I hung out a lot during high school, so I knew his sister since she was 14, and I never thought of her as anything as my friend's little sister.
Anyway, I had a nice apartment with a pool and token-operated tanning bed. Both girls bugged me about using the tanning bed, and I told them I'd pick up tokens, and they could swing by to get them whenever they wanted to go. My apartment complex was gated, and the tanning bed was available 24/7 to residents.
This was in the early 90s, and while cell phones were certainly available, most didn't have them. I was not totally surprised that they showed up without a call, but I wasn't expecting them to knock on my door at 10 PM in the middle of the week, either. My friend's sister told me the reason for their visit, and I went to get the tokens, but they both sat down in no hurry go. I liked them well enough, so I wasn't trying to rush them out the door, but at the same time, I was not fawning over them, either. We essentially made small talk and watched whatever program was on the TV.
The sister's girlfriend wasn't overly attractive (not ugly by any means, though), and she was definitely the bolder of the two. I don't recall exactly how she brought the subject up but somehow mentioned that they would be tanning in the nude and something to the effect of being naked together while the other was in the tanning bed/waiting for their turn. Clearly, the idea being that they would both go into the tanning bed room together. My current 40ish self would have been all over that comment, but my 20-year-old self didn't take the bait. I said something along the lines of one of them could stay with me until the other was done, and the bolder friend countered with the idea that I could come along and keep the other person company until it was their turn. So the stupid 20 year old me immediately jumped to the conclusion that meant both of sitting on the floor in the hallway outside the tanning bed room. All I could think of was that I didn't want to get dressed ( I was in boxers and a t-shirt) and go sit in the hallway, making small talk for 30-45 minutes for both of them to get done.
My reply was something along the lines of that is ok, I'll just hang out here. Bold friend again tried to convince me to come along, and my friend's sister just kind of nervously smiled. Not a I don't want this to happen kind of awkward smile, but more of a partially embarrassed and partially excited smile. Stupidly, I stuck to my no answer.
Thinking about it now, it is a little funny that the idea of being alone with me made them a little nervous, but doing it together was ok. Who knows what would have happened if I went along, but I'm guessing I would have been in the tanning room with two naked 18-year-olds and with a little leadership on my part, a lot more fun. At the time, I was getting laid as much as I wanted (20-year-old logic), but the 40-year-old me knows you never pass up a chance like that haha.
A bit of a side note, my friend's sister would pop over to visit from time to time by herself, and she got a bit bolder changing clothes in front of me (another story). I'm sure she wanted me to make a move, but at the time, she was still in my mind, my friend's little sister. Now, the idea of it being my friend's little sister would have made it even better :-)
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