The Cancún Cougar

by Lingual Larry

What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Phoenix, AZ
Highest education received: Some college (currently in college)
What’s your occupation? Costco
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? No
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 0

The Cancún Cougar

How long ago did this hookup happen? 3.5 months

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? While in Cancún on vacation at an all inclusive resort, I met a 40 year old latina. After me and my brother had worked we took the elevator down to the lobby for breakfast and that’s when I saw her for the first time. She was in some tight purple spandex shorts and a tank top that showed off her body nicely. As I was checking out her camel toe I glanced up and felt like she was checking me out as well, but I didn’t think anything of it at the time. She was also with a white child who was probably 6 years old, with whom she had breakfast with. (I was checking her out from across the lobby). After me and my brother got off the elevator I asked him if he saw that, and he agreed she was good looking.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I didn’t see her after the elevator until the second to last day of our trip. It was about 3pm and I had been drinking since 11am so I was felling myself and was close to heading back up to the room to transition from day drinking at the pool to drinking at dinner. Before I headed back to the room me and my brother hit up the hot tub that’s by the bar. After we get situated in the hot tub I notice its the 40 year old latina sitting right across from me but this time she with a man with a beer belly and that same child from breakfast. As I’m sitting across from her I am blatantly checking her out and she is doing the same to me. It was so obvious and sensual I was almost fully erect..not quite though. We didn’t say anything as 4 min pass, my brother tells me he’s going up to get food then he’s headed back to the room. I tell him I’m going to stay and try and talk to this milf. Shortly after I watch the latina walk with her two guests to the other side of the pool area to some pool chairs and they leave, but M(the cougar) comes back to the bar to smoke a cigarette. At that point I had no anxiety or second guesses about what I had to do as I approached her at the bar, she was standing lighting a cigarette. I asked her if she wanted to get in the hot tub and she told me she just got out, I turned back and got In the hot tub and she joined quickly by dipping her feet in. I asked her about her guests and she referred to the beer belly man as her boyfriend. I asked her when she had some time to herself and she said right now. I said let’s go up to my room, and she smiled and agreed.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? As we made it to the elevator she went to put out her cigarette and I took her hand to stop her and took the cigarette for a quick drag. She told me I needed another one so I took a bigger puff as we made our way on to the elevator. I went in for the kiss as the doors closed and grabbed her hand and put it on my cock. She pulled down my swim trunks and said “nice” as she started jerking me off. When we got to my floor I lead her to the room and briskly opened the door and instantly started taking off clothes. She had some amazing fake titties with nipples that were made for my mouth. I always have enjoyed pleasing a woman through oral so I wasn’t shy about going down on her nicely shaved, tan pussy. I had no problem finding her clit and quickly found out she was a squirter! When I put my dick in I started off fast and she told me there was no rush and that we had all day which I though was something an experienced woman would say. I could tell I was in good hands. I sometimes would lose my erection which isn’t a new problem for me but I was my hardest when I was kissing her. She also said I love the way you kiss me in her sexy accent. I put my tongue in her ass and shortly after she told me to put my dick in which I’ve never done but I didn’t think twice and jammed my cock no lube into her ass. She told me slow but she didn’t seem to be in too much pain. During the sex I asked to get some photos and she said okay so I got some snapchat videos of the hookup which was awesome. At the end I was dripping sweat and my bed was soaked and crooked. When she got up and saw the aftermath she chuckled and smiled liked it was a job well done. She left and my brother came back saying that he was waiting out in the hallway and could hear her moaning. He said it took forever. Probably 10 min later I hear a knock and it’s her at the door and she’s looking for her phone. She is all cleaned up in a dress that is making her ass look amazing. She kisses me in front of my brother as I tell her we haven’t seen it. She takes me out in the halway and gets on her knees and is sucking my dick in the halway. I could hear voices down the hall and that had me the hardest during the hookup. At that point she said youre so big so I took my fully flexed cock and stretched out her cheek with it and seeing her with a mouthful of cock on her knees was amazing.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I felt like the man of the hour and was treated as such. The next day I saw her and she asked about her phone but I didn’t see it. No hugs or anything but I almost wish I got to kiss her goodbye. I have no bad feelings about her now, and she still crosses my mind now and then.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol, Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My family’s friends on the trip. Showed them a still frame of one of the videos. Even showed my step dad.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Getting head in the hallway with other people down the hall.

What was the WORST thing about this hookup? Leaving my bed soaking wet.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Casual sex can be a fun experience

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Rolled the dice on going in no condom

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? It hasn’t played a big role as I’m somewhat inexperienced but it is a fun time and a good memory if the sex is good.

What do you think about the Casual Sex Project? Don’t know what it is but I like the platform to share my story

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