Sex With A Trail Buddy



What’s your gender? Woman
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Environmental Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

Sex With A Trail Buddy

How long ago did this hookup happen? 3 months ago

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

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? Jack is 44 years old, blonde hair, blue eyes, over 6ft tall, and easy on the eyes. I met him and his wife last year at a local trail maintenance event and we became friends. Jack and his wife are originally from SoCal and have been married for 20 years and I’ve been married for 7. Jack’s wife loves the outdoors and my husband does not.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At our May meeting, a group decided to plan a three-day hike. We would hike to a destination then rent a car and drive back. Jack & his wife already reserved the back country sites along the way so the group would not have to share the shelters. I’ve only done ‘day hikes’ so I signed up. A week later Jack’s wife tore her ACL and had surgery. The hike was in three weeks and she wasn’t given clearance by her Dr. to hike. She was nice and offered to let me borrow her lightweight backpack and a few other items so I wouldn’t have to purchase them.

At the follow-up meetings Jack’s wife stayed home. She wasn’t going so she had no interest in the planning. The group was dwindling and Jack and I had begun to flirt with each other. At the last meeting, one week before the hike, it was just me and Jack so we met at his house. We discussed the situation. I told him I still wanted to go but I planned to let my husband think I was going with a group. I told him, “My husband doesn’t care anymore and will never follow-up with what I do.” Then I got a big surprise out of Jack and his wife. His wife tells me she’s fine with me going alone with Jack because their marriage is open and they’re also swingers. She told me that’s why she let me borrow her pack and supplies. Jack always carries the tent and large sleeping back and she carried most of the dehydrated food. She just assumed we would be having sex on the trip and didn’t mind at all. I’ve always been faithful and until that moment, I hadn’t thought of having sex with Jack. Now it sounds like it will be expected. His wife went to bed and we made the final plans. She would drive us to the trailhead and we would call her after 3 days and she would drive up and pick us up. As I was leaving, Jack squeezed my butt, gave me a deep kiss and said, “I can’t wait.” I left horny.

The next few days were exciting. What started out as planning an innocent hike turned out to be planning my first affair. I’d never done anything like this before. My mind was spinning and I was a little nervous because my husband is the only man I’ve ever been with. Thoughts of backing out never crossed my mind.

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? It was Day 1 and we arrived at the first campsite earlier than expected. I helped Jack with the tent then we went to the creek to get water to filter. We took our boots off and put our feet in the cold water. Jack leaned in and kissed me and began rubbing by breasts. He took off his shirt and I admired his ripped stomach. My husband had slowly grown a beer gut. I worked on his shorts to get his penis out. He was bigger than my husband and I made sure to tell him too. I knelt down and sucked him for a while before I stood up and took off my shorts. We found a large rock and folded our clothes so I could have something to sit on and had amazing outdoor sex.

Now that the sexual tension was gone, we had a wonderful time on the rest of the trip. Anytime we found a nice private look-out we had sex. Each night at the campsite we had sex many times. I had more sex on that trip than I had in the past couple of years with my husband.

His wife picked us up and drove us back. I was obviously glowing and she could tell by my smile, I’d had a good time.

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? Three months had passed and I had been arguing with my husband because he stays out drinking. We haven’t had sex in a couple of months either. Out of the blue, Jack sent me a message that his wife was away and asked me to come over. He knew we both agreed we wouldn’t meet up anymore after the hike but his timing was right and he said we can have much more fun on a bed than the hard ground. My husband was with his friends so I went to Jack’s. This time Jack was able to spend a long time giving me oral. He kept swirling his tongue on my clit till I came. I was so horny, I started out cowgirl and rode him hard. I was trying to make him cum first but I actually had another orgasm in the process. We switched to missionary for a long time then he bent me over doggy. He pounded me deep and hard till he finished. It’s nice that he can last for a long time. I left his house sore, exhausted, and VERY satisfied. I plan to continue having a casual relationship with Jack in the future.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? A little bit

Why do you regret this hookup? Until I had sex with Jack, I’d only been with my husband and I felt a little guilty at first. I know my husband will never find out I’m cheating because he doesn’t seem to care anymore. It also helps to know that Jack’s wife is OK with him having casual sex. I take responsibility for my marriage and the damage but I would feel bad breaking up someone else’s marriage.

What was the BEST thing about this hookup? Jack’s big penis and his ability to last a long time!

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m open to having a friend to have casual sex with. Jack is someone I’m comfortable being with. For now, I don’t see myself having sex with anyone else but him.

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

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

What do you think about the Casual Sex Project? It’s nice to read about similar situations.

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