by

What’s your gender? Man
How old are you? 30
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: Post-graduate degree (currently pursuing)
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
How many sexual partners have you had in your life (including oral sex)? 11
How many hookup stories have you here posted before? 0

Caught a Cougar While Hiking on My Birthday

How long ago did this hookup happen? 8 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? About 8 years back I joined a national environmental association as a volunteer. Over the course of the year, I became friends with the other members in the local chapter, one of whom was ‘Sarah’. Sarah was an attractive blonde, probably about 5′-6″ and in good shape. At the time, though, I actually had my eyes set on someone else, so never really thought of her sexually. Besides, she was 10 years older than my inexperienced 22 years, and seemed happy in a long-term lesbian relationship.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After about a year, a bunch of us from the local chapter organized a cross-country road trip to the national convention in another province. It was fun as road trips go, and we took turns at the wheel so that we could make the 13 hour trip overnight.

At around 3am, I took over just as we started getting into the heart of the Rocky Mountains. As thick fog was rolling in and it was late at night, Sarah sat up in the front seat to keep me company while everyone else slept. To this point, I don’t think we’d really had many conversations before, even though we considered each other friends. As we got talking, she revealed that her relationship had just recently ended. We also realized that we had a lot in common and we enjoyed the conversation. With my birthday coming up the next weekend, and no plans other than to go hiking for a few days on my own, I invited her to get out of town and tag along for a weekend in the backcountry with me. With her agreeing to join me, I was excited just to have someone else on the trek.

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? The next weekend, the two of us set off with our heavy packs into the remote backcountry. With the access road being closed, our first day was spent slogging up the long forestry road under the blazing July sun, just to get to the trail head. Finding a clearing as the sun was getting low in the sky, we decided to set up camp for the night and start the trail proper at the crack of dawn. Exhausted, we skipped building a fire, and quickly made dinner before cleaning up and heading into our shared tent.

As the night grew darker, the temperature quickly dropped as well, and our summer sleeping bags grew increasingly adequate to keeping us warm. We instinctively snuggled closer together, eventually even linking our bags together so that we could properly spoon in our long johns. In such situations, my hands tend to grow a mind of their own. Slowly, they started moving over more and more of Sarah’s body, her increasingly heavy breathing and thrusting of her body back into my own only encouraging me further. Pretty soon we were both scrambling to tear each other’s layers off and things grew increasingly wet and sticky as we got each other off with our hands. After a year of being just friends, I’d quickly found out that not only was Sarah bisexual, but that we also had great sexual chemistry.

The next day was just as hot as the first: 30 degrees Celsius with not a cloud in the sky. Starting off the day by taking on the largest ascent of the route, we climbed up onto a plateau littered with small lakes and ponds. It was the perfect place to stop for lunch and a swim before continuing on for the afternoon. With the sun high in the sky, we ignored our bathing suits and went skinny dipping in one of the smaller lakes, ice cold with a few remnants of the winter snow pack still sitting comfortably in the water at the far end. After lunch and and a quick siesta, we found ourselves getting handsy again. Turned on by the bulge growing in my pants, Sarah unzipped me and took me into her mouth, showing me just how good an older, more experienced woman can suck cock. She quickly brought me to the brink, and after I told her how close I was, kept sucking until she enthusiastically swallowed every last drop I had to offer.

That night, after setting up camp and cleaning up from dinner, we were both anxious to get back into the tent. I had a few condoms in my backpack and we were desperate to fuck. Unfortunately, though, I wasn’t able to perform, and we had to resort to using hands once again. The next morning we laid our sleeping pads and bags out under the rising sun as we tried again with the last two condoms. As it turned out, in my inexperience of only having had sex a couple times before with one other partner, I simply had bought condoms that were too small, and they were quickly killing my erection after putting them on.

Aching for real sex, we both talked about our past sexual experiences as we hiked back towards the trail head, making ourselves comfortable that STIs weren’t an issue on either side. After a few more hours in the hot sun, we took a skinny dip in a creek along the way, and decided to try once again without a condom, but the cold glacial water splashing around my feet thwarted our efforts to even get started. Downstream, at some natural hotsprings, we were finally able to satisfy our desires.

Walking in to the hotsprings recreational area, we saw no sign of any other recent hikers just as had been the case all weekend. Having the place all to ourselves, we decided to enjoy the pools in our naked glory. Before long, we were all over each other again, this time warmed up and making a go of it on the nearby picnic table. Finally rock hard, I slid my seven and a half thick inches deep inside her wet pussy and our anticipation was finally replaced with pure pleasure. Within a few minutes, I brought her to orgasm before pulling out and releasing all of my pent up sexual energy over her flat stomach before just collapsing into her arms. It was at that moment, when she asked if I wanted to spend the night back at her place to properly celebrate my birthday, that several months of incredible sex and a great deal of learning on my part began.

Back in civilization, we had incredible condom-free sex all night long before she took Plan B the next day. Having worked out some rules for our casual relationship, and finally finally buying the large condoms I needed, our sex only continued to improve over the course the next several months. I stayed at her place most nights, having incredible sex before bed, waking up around in the middle of the night for a second round, and finishing off with a morning pick-me-up before heading to work each morning. On the rare occasions a condom broke, incredible condom free sex resumed until we could get Plan B the following day. In bed, on the couch, in chairs, on the floor, in the kitchen, we quickly invented a million new positions as we learned how to best please each other.

On one memorable day, Sarah woke up not feeling particularly enthusiastic. Working magic with my fingers, however, she quickly became insatiably horny for the rest of the day. Having told a mutual friend we would come visit though, and needing to run some errands, we set out walking across town on what was a beautiful summer day. By the afternoon, having barely made it halfway across the city, Sarah could no longer contain her desire, and we found a quiet park bench in a community garden. Wearing a skirt, she pulled off her panties and straddled me as I pulled my hard cock out through my fly, attempting to remain inconspicuous as we fucked in broad daylight in a busy neighbourhood. When at one point a gardener came to water his plants in the plot next to us, we grew rapidly impatient as we pretended to be just making out, my hard cock still firmly inside of her but unable to thrust in and out.

Closer to our friend’s place, both desire and the intrigue from having sex in public struck again as we passed by an empty children’s playground. Hidden inside a fibreglass tunnel, we slowly fucked again. In that moment we both looked at eachother, knowing we weren’t going to see our friend that day. Instead, we were heading straight back to her place for a long night of uninterrupted sex.

While this kept up for several months, eventually we both decided it was time to return to being just friends. Surprisingly, we both came to this thought around the same time, and came to a mutual agreement. We remained friends for a couple years, although we eventually lost touch after she moved out of town. Despite having many more partners and many more experiences since, some of our experiences that summer are among my favourite. Certainly that summer played a huge role in my sexual education, and helped make me a giving lover in both my long-term and casual relationships since. Altogether, it was one summer to remember!

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? As I mentioned, Sarah was just out of a long-term relationship when this first started. I wasn’t particularly looking for a relationship at the time either, and so we naturally fell into a friends with benefits situation that really just worked from the beginning. We talked about what we both wanted, and worked out some rules based on mutual respect, which I think helped a lot. We’re still on good terms today, even though we haven’t really kept in touch since she moved away.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history, Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, To feel more confident, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

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 told some friends about my situation at the time, and they were enthusiastically supportive. I’ve also told most if not all of my lovers since about it, with varying degrees of detail. I try to encourage open disclosure of sexual history and desires because it makes current sex and relationships so much better. Recently I had another friends with benefits situation that started from tinder, and we talked in depth about all of our past experiences, as well as other people we were seeing at the time.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I learned an incredible amount about myself as well as about pleasing women. Overall it was a great experience.

What was the WORST thing about this hookup? There were only so many hours in a day we could have sex. Seriously, we would’ve gone more if we could have.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m not sure it did. I was taught about sexuality at a young age, with my parents enrolling me in a sex-ed class for young kids when I was only about 6 at the earliest. From that point on I think I’ve always been fairly open and curious. I’m not sure if I ever held sex up as this magical thing only for marriage or those in committed relationships. It definitely did make me more confident in myself though, both in my abilities as well as my body.

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

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

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? I think sex is an important part of a healthy lifestyle. If you’re in a monogamous committed relationship, that’s great, but I don’t have any opposition to casual sex, open relationships, or any other arrangement. If it works for you, and your partner if you have one, then that’s great. Keep the communication flowing and keep exploring what you like.

What do you think about the Casual Sex Project? It’s interesting. Sort of a cross between erotic literature and scientific research.

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

Comments