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The Ultimat Cougar Expeience
As my plane touched down in Orlando, my last conversation with my best friend was still playing in my head. Sandy is 45, gorgeous, sexy and fun. She has had some very nice, classy, successful boyfriends and I have heard about all of them. What she told me at lunch yesterday was somewhat of a shocker. "Jill, have you tried a younger guy" she said? "Well, yes, I have." I am 42 and have been with a 40 year old boyfriend for about 6 months. "Jill, I'm not talking about a couple of years. I'm talking major league cougar time..like with my current. Psst..he's 25!" "Oh my god", I replied. I couldn't help but giggle a little and the look on my face must have been priceless as she started laughing at me. Well, after a couple of wines, the details poured out of her and I couldn't help but be fasinated, intrigued, and probably pretty turned on. Jill then asked "hmmm...how young would you do?" "Well, I never really thought much about that. I didn't think that a 42 year old would have that much choice"? "Jill, you're beautiful, hot, and sensual. What younger guy wouldn't want to give that a shot?". The wine flowed freely and I have to admit, it was interesting. Sandy told me all of the interesting, exciting orgasm producing craziness of fucking a 25 year old. Just recalling this conversation was creating a real wet spot in my panties.
The landing jolted me back to reality and I started thinking about my schedule over the next couple of weeks. I was in Florida for a training school at a resort and it was going to be pretty hectic. It was Friday evening and my boss encouraged me to leave right after work so I could have a relaxing weekend at the resort before work started on Monday. My boss is pretty considerate...a really great person to work for. Anyway, it was pretty nice to have some time away and although working hard, I hoped to be pampered just a little bit. I didn't know it would start so soon. As I grabbed my luggage, I had expected to grab a transport to the resort which was about 45 minutes away. I was surprised to see a young limo driver holding a sign with my name on it. He was a really cute "kid" which appeared to be about 18. Brian was a really good looking, clean cut young man that looked really great in his white uniform. He was not a muscular guy, but in really great shape and innocently shy. Although I was dressed conservativly, his 18 year old hormones certainly found enough to induce a raging hard on. As he opened the door for me and I slid into the front seat, I was right on level to see the outline of his cock in the white shorts. I just giggled and didn't think any more of it. The ride was fun, and we talked alot. I got through some of his shyness until I asked if he had a girlfriend...then I detected an uneasy, embarassed look on his face. I prodded him a little to find out the reason, and found that he was very inexperienced..probably due to the shyness. All his friends were getting women, but it was obvious he was not..poor guy! Anyway, I asked him if it was safe to walk on the beach late at night and he said to stay closer to the resort if I was alone. "Well, are you available later to be my 'beach escort'? What time do you get off of work?" "I'm done at 9", he responded. "okay, where can we meet", I asked. "Well...this totally against the resort rules", he said. "We need to be careful". "not a problem, I understand." We agreed to meet in back of the hotel next door to the resort at about 9:15. I went to my room to get freshened up after a long flight and put something on a little more 'beachish'. I decided on just a silky pair of running shorts and a pull over top..sans bra of course. I figured it was dark and not really noticiable. I met Brian and we headed down the beach. The waves were making for a very erotic atmosphere and I was just enjoying the sounds, the sand and my young escort. The breeze and the atmosphere was making my large nipples stand out noticably. The sight wasn't lost on Brian. He certainly was noticing and evidenced by the bulge in his shorts. What did I have here? I wasn't really sure how I should handle this...the conversation with Sandy came back into my head. Something Brian said snapped me out of it. "Here, let's move further up on the beach. I don't want to get you wet". "Too late I said, I already am". I didn't know what made me say that and Brian didn't catch on at first, but when he did, there was an embarassed pause. I couldn't believe I said that, but I guess I was glad that I did. I Said, "oh, I'm sorry..I didn't mean to catch you like that. I guess it's just the atmosphere and my usual playful personality". "I like it", he said. "You're so much easier to talk to then the girls I'm around". "Brian, you're adorable" I said. With that, I pivoted around and gave him a kiss. As my tongue searched out his, I could feel the shudder going through his whole body. This hormonal (very horney) young man could be a lot of fun. I had forgotten how much. I think he was totally shocked as I kissed him and when I pulled him closer to me, I could feel his raging hard on. What have I done here?
I broke off the kiss and slowly turned us back towards my hotel. It's getting late and we should head back. I could almost hear his disappointment as I knew his raging hardon was screaming for attention. more to follow