Cougar in Capri

by ha39727
Gender: Female

Age: 37
Race/ethnicity: Anglo
Location: Texas
Highest education received: College degree (eg., BA, BS)
Occupation: Legal Secretary
Religious affiliation: Protestant
How religious are you? Somewhat
What best describes your sexual orientation? Mostly heterosexual
How many hookup stories have you here posted before? None


Cougar in Capri

How long ago did this hookup happen? 10 months ago

How would you best classify this hookup? One-night stand/vacation hook-up

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? He was a sexy young American guy in his early 20’s. He had a beard and was wearing nice, but casual summer clothes and a fedora. I met him while I was on vacation in Italy last July. I was spending the night on the island of Capri with a couple of girlfriends. One of my girlfriends was taking pictures of me standing in front of the bougainvillea plants. Two young guys walked between us. One said they were sorry to interrupt, explaining “we aren’t from around here”. I asked where they were from. When they said Texas my friend and I laughed. We were from Texas too! We all couldn’t believe the coincidence. My girlfriend and I offered to smoke them out to celebrate the happy coincidence of meeting fellow Texans so far from home. While we were smoking I learned that they were cousins. One was nineteen, the other was twenty-three. They were from an old-money neighborhood in Dallas. Trust fund babies I deduced. We parted ways after smoking, agreeing to meet-up later at a dance club. We ran into them a couple hours later at the club and then strolled around for a bit. I was chatting up the nineteen year old the whole time, but I had my eye on his older cousin. I was trying to play it cool and not be too obvious. I found out later from my friends he was asking them about me at the club while I danced with his cousin. He asked them how old I was. They just vaguely answered that I was “in my early 30’s”. (I was 37.) So great when your girls got your back!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Eventually he’d had enough of his younger cousin’s drunken ranting and decided to ditch him. We were standing there with my girlfriends outside a pub discussing where to go next. He looked me right in the eye and said “so what are you gonna do?” I smiled and said, “I’m going wherever you’re going cowboy!” He just smiled and told me to c’mon. It happened so fast my girlfriends didn’t realize what was happening until we started walking away. I was laughing hysterically at the “WTF?” looks on their faces as we walked away! We decided to go back to the tiny hotel room I was sharing with my friends. At first, the inn-keeper in the lobby didn’t want to let him into my room. After much begging and pleading in broken Italian, he gave me the key and we proceeded down the hall to my tiny cheap hotel room.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The moment we closed the door, he kissed me urgently and shoved his hand up the crotch of my board shorts. I wasn’t wearing any panties. I mentally congratulated myself on making the wise decision to spring for a fresh Brazilian wax before leaving Houston for vacation a few days earlier. Best decision ever! We quickly moved to the bed. I insisted we keep completely on one side of the bed, out of respect for my girlfriend who would be sharing the bed with me later. He was obliging in a very gentlemanly way. Gotta love a true Southern gentleman! I went down on him and I could tell he was appreciative of my years of experience and expertise. He had a beautiful dick. He almost came, but asked me to stop. I got on top of him and rode him like a cowgirl! I kept saying “It feels good! I want you to fuck me all night!” I could tell he was making a real effort at pleasing me. Southern men are wonderful that way, it’s a kind of chivalrous thing they do, even when it’s just a hook-up. But alas, I was overwhelmed and a bit nervous. I hadn’t been with a man his age since college. So I faked an orgasm. It’s not like me to fake it, but we were under a time crunch. So I decided to give him an A for effort and fake it. And I’m glad I did, because the next part was the best.

He got me up on all fours and gave me oral sex like that. Ass up! He was shameless about it, licking me in places that only my ex-husband had before. (Yes, THAT place!) Then we did it doggie style. It was very good. He had a lot of energy. He told me to play with his balls. I was only too happy to lick the palm of my hand and then oblige him. He came and then we laid down for a few moments, exhausted. I knew he was in a hurry to get out of there, but I asked that he give me a moment to recover before we got up. He was polite about it. We got dressed as he mumbled something about having to go find his cousin before their rented yacht left the island in the morning. I walked him to the lobby, crossing paths with the inn keeper and one of my girlfriends. They both looked at me with big knowing smiles!

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Thankfully, he was prepared. He had a condom and did not make a big fuss about using it. For a second he thought it had broken in the middle of doggie style. Afterwards he mentioned that he almost thought it broke, but said he checked and it didn’t break. Then he asked if I was on the pill. I laughed and said, “The Pill? Oh no honey, I’ve already had all my babies. My tubes were tied last year.” He gave me a blank look, like he wasn’t expecting that response.

What were your REASONS for having this hookup? At the time, it seemed romantic. Meeting a handsome stranger from back home in a glamorous and exotic place. On another level, it was a conquest of sorts. It felt affirming to show myself and my friends that I still had “it”.

Were alcohol or drugs involved? If so, how much? I had quite a bit of champagne over the course of the evening leading up to it. And we smoked a spliff together with his cousin and my girlfriend a few hours before. He had been drinking all night and my girlfriend gave him a painkiller pill before we met at the club.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Afterwards, we did the “walk of shame” through the lobby and he left. I was glowing with satisfaction. Like a cat that had just caught a mouse! We didn’t exchange contact info. I unsuccessfully tried looking him up on Facebook afterwards using his university and his first name, which was unusual. I just wanted to say hello and ask if he ever found his cousin that night. Even though we never spoke again I was really glad we met and hooked-up. I hope he remembers it as fondly as I do. I think it was probably a learning experience for him to be with someone a little older.

To whom did you talk about the hookup? How did they react? My girlfriend that I was visiting sat out on the balcony of the hotel into the wee hours of the morning with me smoking and talking about it. She had been happily married for over 20 years. This was the first time she had seen me since my divorce. She kept saying how she was in awe of me. We were still talking about it the next morning with my other girlfriend who went to Capri with us. I was saying how I enjoyed it, but I didn’t remember sex being over so quickly when I was in my 20’s. She said “Well of course it’s that way when it’s with someone who doesn’t care about you!” That really hurt my feelings a lot. My married friend spent the ferry ride back to Naples consoling me.

Was this a consensual and/or wanted experience for you? For your partner? Yes. I let him know I wanted to be with him. But he took it from there.

Do you regret this hookup? If so, why? I don’t believe in regrets. Ever.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about it was the actual sex. And that moment outside the pub when he looked at me and asked what I was going to do next. That’s when I knew it was on and I seized the moment! It was an important event in terms of how I see myself sexually. It was less than a year after my divorce was final. I had been through ten years of marriage, two pregnancies, births, diapers, and military deployments. Two months after we broke-up my “soulmate” took up with a younger, skinny, blonde girlfriend, like it was nothing. I couldn’t just move on like that. Hooking-up randomly in a beautiful exotic place with someone younger showed me that I was still a sexy, confident, and bold woman. I hadn’t changed. I hadn’t lost anything. Now I’m free to enjoy sex whenever and with whomever without worrying about what it says about who I am or who I will be. I can just enjoy it and go back to my “regular” life when it’s over.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup or anything else? If someone had told me in college that I’d still be hooking up in my late 30’s I never would have believed it. Thank you for allowing me to share and for taking the time to read it.

You have a hookup story to share? Submit it here!