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By canepar
#66520
Back in high school I remember my best friend’s mother. She was a gorgeous brunette, tall and slim with a nice perky rack. Honestly I felt her mom was the hotter woman I have already seen because she had this incredible toned mature body and big fantastic gravity defying tits, if there was a picture in the dictionary for the word milf it would be this woman. She was also incredibly nice and friendly to boot so either were always pleasant to be around.

Senior year we were on a school trip and one night at the hotel a bunch of us went to the pool area to swim and for the guys to check out girls in bathing suits of course. Sadly they were all one pieces because of the dress code for the trip but still hot. Well eventually my friend's mom who was one of the chaperones came down to take over so some of the others could go up to their rooms and take a break or whatever, it was getting sort of late and the majority of people had already left the pool so it ended up just being the two chaperones for the 15 or so of us still down there. I was eyeing the hot tub across the courtyard now that it was empty so I asked her if I could head over to it. She said sure, she would go with me and the other chaperone would stay at the pool. So we went over and started getting in. Now my friend's mom was wearing a light jacket and some of those workout pants that zipped down the legs and looked amazing on her, I was joking with her about she should get in, the water felt great after the long day.

Then to my surprise and much delight she said sure why not and proceeded to unzip her jacket revealing her glorious rack in a bikini top and zipped down the legs of her pants so she could step out of them and reveal matching bottoms. I'm surprised I do not drowned as my jaw practically dropped to the bottom of the hot tub. My eyes were locked on this stunning milf in front of me in a bikini. Now it wasn't skimpy by any means but after only seeing the girls in one pieces to watching a beautiful woman basically strip in front of me it was a sight to behold, it wasn't revealing at all but damn did her curves fill it out right. She dropped down into the water and grinned at me saying I hope you don't report me for my dress code violation. I stammered and stuttered of course not, I wouldn't dream of it.

I'm sure this would have been quite a hilarious spectacle to an outsider with my awkward flirting and joking with her. She never seemed uncomfortable with the situation and seemed to actually enjoy the attention. We had a great time talking and hanging out for close to an hour before the pool area was finally closing about 11, it was one of the highlights from the trip. When we got out it had gotten fairly cool out with the breeze and she discovered the other chaperone had taken her towel when she left the pool earlier, leaving her without. She didn't want to get her jacket and pants wet so I, being the chivalrous gentleman that I am, quickly volunteered my towel so she wouldn't have to walk dripping wet in the cool air all the way back to her room. She readily accepted it and bundled it around her goosebump covered body. I also volunteered to "escort" her back to her room so I could get my towel back.

We made some small talk about graduation plans and what not on the 5 min walk to her room. When we got there I fully expected to get my towel and go straight to my room, despite the fantasies racing through my head. To my surprise she invited me inside, insisting that I let her get me a bath towel to dry off since I had to be freezing (I was) before walking back to my room. I dried off a bit and chatted with the other chaperone sharing her room who was watching tv while she stepped into the bathroom to finish drying off and get changed. To my surprise, 20 min later when she emerged, she had only a skimpy black set of bra and panties with her wet hair and I swear she never looked sexier to me than she did at that moment. She had not seen me there so the other chaperone warned her about my presence. She looked surprised but nor embarrassed and told us she thought I’ve already gone. The other chaperone wanted to throw me out of there but she said she didn’t care about since I had already seen enough and, after all, the bikini was more revealing. She put on sweatpants and a t-shirt, handed me my towel and said she would walk me back to my room since it was technically almost curfew so I wouldn't get in trouble because I helped her out.

On the way to my room she said she hoped I didn't mind not telling her son what I had just seen. She told me she thought that that should just be only our secret and there was no need to share it with others. I calmly told her of course not, all the while my mind was reeling with thoughts of her gorgeous body. When we got to my door she thanked me again for being sweet and letting her use my towel, right before she popped up on her tiptoes and gave me a quick kiss on the cheek and telling me to have a good night. I swear my heart almost stopped at that kiss, to this day I am amazed I kept it together and didn't pass out or say something stupid, I managed to tell her good night as I stepped into my room.
By willman
#67055
Memories are made of moments like that, they always bring a smile to your face when you remember them. Thanks for telling your story.
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