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What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Obsessed
How many sexual partners have you had in your life (including oral sex)? North of 70
How many hookup stories have you here posted before? 4 – 5

Met A Chilena In Cancun

How long ago did this hookup happen? +3 years

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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? That story happened in March 2016.

I was suffocating in the relationship I was in at the time and I decided to take a break by fleeing, alone, one week to a nice resort in Cancun. I was seriously questioning myself about the future of my relationship.

The first evening at the Cancun resort, at dinner time, I noticed three Spanish-speaking people seated at a table not too far from mine, two ladies and a man. One of the lady caught my attention. She had a very cute, although unusual, face. In the course of the dinner, she stood up to go get something at the buffet and man oh man, I had never seen a woman with such a sexy walk. The tight pants she was wearing highlighted a butt and legs to die for. I think the Pope himself would have had a boner. From my place, I could see that many men’s head were spinning in her direction as she was walking by, to the great displeasure of their female partners. On her way back to her table, I noticed that she discreetly took a peek at me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next afternoon, I was hanging at my prefered spot on the resort (the pool bar), when the Spanish-speaking trio arrived. In the context of a resort, it is relatively easy to engage a conversation with strangers and so I did. Except that the man in the trio didn’t speak a word of English, his girlfriend (I learned later about their status) could only speak a little bit of English and the cute one, with the sexiest walk of Earth, did speak English, albeit not to Oxford standards. I engaged the conversation with Louisa (the cute one, fake name) with all the known preconceived formulas and the usual jokes. They were from Santiago, Chile.

After they ordered their drinks, the man (Ramon) and the other lady (Maria, Louisa’s sister I later learned) were ready to head back to the beach. Louisa told them something in Spanish (a language I barely spoke at the time) and when Ramon and Maria left, Louisa stayed with me. Which was, obviously, a very good sign. The conversation eventually evolved to more serious topics, essentially our lives. I, of course, had to lie a little about mine, pretending that I was single. Louisa had been divorced for two years and she had a 17 year-old son. She was four years younger than me.

We eventually continued our conversation during a long walk on the beach. Her unique face, that I found intriguing the previous evening, was explained by the fact that her mother is native to an indigenous group of southern Peru (having Quechua as their native language), while her father was the son of an italian immigrant. Hence, Louisa’s blood is half european, half native which explains her quite unique face. I cannot say that she was the prettiest lady in the world, but she was definitely cute. And her walk / sexy butt and legs more than made up for her B-cup chest.

I invited her to have dinner with me that night, invitation she accepted. After dinner, we headed to the resort’s discotheque.

Everywhere she was going, Louisa always attracted the attention. She was driving the mexican guys working on the resort crazy (I later learned that one of them sneaked into the resort’s reservation system to get her phone number and contacted her on Whatsapp – she had to block him). She had a very engaging personality; she was definitely a people person. There was just something about this woman. It took me a while to realize what it was and I can now say that this Chilena was, simply stated, charismatic. We were connecting on so many levels. I could sense that the physical tension between her and I was building.

At the discotheque, it was magic. I’m not the best dancer in the world, but we danced, danced and danced. Her charisma and incredible sex-appeal was in full display on the dance floor and my genuine physical attraction to her was growing with each passing minute. My hands were all over her shoulders, her back, her hands, her hips. She never pushed back. She clearly enjoyed the attention.

Shortly after midnight, we headed back to the resort. We took a short walk on the beach. After which I invited Louisa to my room and she more than gladly accepted. There was absolutely no mystery about what was going to happen. When in the room, we started to kiss passionately (she was a good kisser) and we went under the shower (I hate having sex if I’m sweaty).

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? Once on the bed, I quickly went down on her. It took 3-4 minutes before she came. After that, I wanted to enjoy her butt the best I could, so I turned her around on her belly and started licking her anus, while caressing her clitoris with a finger. She was moaning and enjoying the moment. She came again. I didn’t ask any favor in return. I put her on her back and went into her.

Damn!

I had never fell a vagina so tight. I later learned (again) that she delivered her son through a C-section, which explains why she was still that tight. I don’t have a porno-size dick, but I can’t complain (actually, my dick – I have been told many times – is apparently larger in girth than the average dick). Well, I had to be careful at first when I penetrated her because she fell some pain. Once she got used to my size, she relaxed and she climaxed, again, in a matter of a few minutes. I had to calm down a little myself, otherwise I would have come in a few seconds given how tight her vagina was. I was able to ragdoll her for the next hour or so and, in total, she came six times. After which I came into her. That lady was a sex bomb.

The rest of the week was more of the same. We had sex over and over again, 3 to 4 times a day. During one of our sex session, I asked her to give me a blowjob. She had never done that before! So, I initiated her to that sex act. I still remember the look on her face the first time I came in her mouth. She gave me 2 other blowjobs during the week which she performed relatively well and, most importantly, she swallowed my cum like a pro. We also tried anal sex (which she had never done before either), but that didn’t work.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? The goodbyes, on the Saturday, were very emotional and tough. Our relationship had grown into something more than just sexual.

Back home, I quickly ended my six-year relationship. Louisa and I maintained a close relationship, through Skype, for the next 3-4 months. I was in love with her. I began learning Spanish online. In July of that year, I spent 10 days in Santiago which, again, was magic, on so many levels. I wanted to marry her. Her feelings were reciprocal.

Little by little, after that, Louisa became more distant. Her son (whom she adored and spoiled like crazy) was opposing our relationship. She was having lots of second thoughts about that long-distance relationship with this guy from the North. Nevertheless, after many hesitations, she came to visit me in September, for two months.

The sex with Louisa was still amazing (we even had a semi-threesome one evening with a dancer in a striptease club), but I then slowly started discovering (long story short) that this Chilena had many issues. On top of being very impulsive, she was also extremely jealous. Once, at the mall, a woman I didn’t know asked me for direction. I politely answered. That was enough for Louisa to suspect that I had had sex with her. After three weeks (she was supposed to stay with me two months), on a Saturday night, she told me that she wanted to go back to Santiago. The following Tuesday morning Louisa was in a plane heading to Panama, on her way to Santiago.

Leaving me so impulsively, three weeks in a stay that was planned for two months, was the definitive deal breaker. Back in Santiago, Louisa immediately started to implore me to forgive her and everything, but I resisted (there was many other issues to explain my decision, but her leaving me the way she did was the proverbial straw that broke the equally proverbial camel’s back).

I had enrolled in a Spanish immersion school that I was to attend in Santiago in January 2017. But I went to Lima (Peru) instead (I posted another story, here, about that stay).

Still to this day, almost two years after she left me, I know that Louisa stalks me on Facebook. I know she haven’t met another man. And I do admit that I still love her, in a certain way. Talk about an impossible love…

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To feel better about myself

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? I introduced her to my family, when she visited.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Very

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Very much

Why do you regret this hookup? I fell in love with a lady who turned out to be emotionally unstable.

What was the BEST thing about this hookup? The sex AND the love.

What was the WORST thing about this hookup? That it ended.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It has changed the way I perceive women, that’s for sure.

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

All things considered, how NEGATIVE was this experience? Very negative

Anything else you want to add about this hookup? I’m still struggling to get over it.

What do you think about the Casual Sex Project? I like it a lot, although some of the stories seem made up. Funny how the black males being described in some stories here ALWAYS have huge dick.

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