Back in high school I was friends with this gorgeous brunette, tall and slim with a nice perky rack. Pretty much every guy (including me) would have given their left nut to fuck her but to my knowledge nobody ever got any action from her. She happened to be a spitting image of her mom, so all the guys also lusted after her mom as well. Honestly I felt her mom was the hotter of the two 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. Both mom and daughter were 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 two chaperones for the 15 or so of us still down there, another friend's dad and the hot milf. A couple of us were eyeing the hot tub across the courtyard now that it was empty so we asked her if we could head over to it. She said sure, she would go with us and the other chaperone would stay at the pool. So me and my hot friend and her mom and a handful others, mostly guys, 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, a couple of us were joking with her about she should get in, the water felt great after the long day.
Then to our 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 none of us guys drowned as our jaws practically dropped to the bottom of the hot tub. I'm sure the other girls were rolling their eyes at us but mine 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 us 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 us saying I hope you don't report me for my dress code violation. All of us guys stammered and stuttered of course not, we wouldn't dream of it to what I'm sure were more eye rolls from the girls. Just a few minutes later, the girls announced they were going back to the pool, undoubtedly so they could get away from our clumsily veiled flirting with a woman 20+ years our age.
This left a milf alone in a hot tub with almost 10 horny 17-18 year old guys, I'm sure this would have been quite a hilarious spectacle to an outsider with our awkward flirting and joking with her. She never seemed uncomfortable with the situation and seemed to actually enjoy the attention. We all 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 her daughter had taken her towel when she left 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 to the jealous glares of the rest of the guys.
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. Now I wish I could tell about how she peeled her suit off in front of me and we spent the whole night fucking, but sadly that did not happen because this was real life. Instead I dried off a bit and chatted with the other chaperone sharing her room while she stepped into the bathroom to finish drying off and get changed. When she emerged she had on sweatpants and a t-shirt with her wet hair and I swear she never looked sexier to me than she did at that moment. She 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 she used my towel to dry off so she could save a room towel for her shower. I calmly told her of course not, all the while my mind was reeling with thoughts of her naked and rubbing my towel all over 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.
Looking back, I can read all sorts of motives into her actions and words other than what was almost certainly complete innocence on her part, or at the most a little bit of harmless flirting... but then again who knows and that has fueled all sorts of fantasies for me over the years. Knowing what I do now I find it hard to believe she didn't have any idea of the effect she had on me and the images in my head and actions her words could and did provoke. Of course I jacked off that night in the bathroom holding my towel that was still damp from her and thinking how I was touching something that had touched places on her that every guy could only dream about, it was amazing. I also found out later my friend's dad who was the other chaperone was very jealous of not being over at the hot tub to see her in her bikini, so of course we teased and messed with him about how awesome it was.
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12-27-2015, 09:21 PM
