This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Northeastern United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Outdoor Recreation Guide/Manager
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Still rocking a serious sex-drive, and I’m very fit for my age
How many sexual partners have you had in your life (including oral sex)? More than 10
How many hookup stories have you here posted before? First one/best one

When In Doubt…

How long ago did this hookup happen? 4 years

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 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? Lee (what we’ll call her for purposes of anonymity) was 20 yrs, about 5’4″, maybe 100 lbs soaking wet, very skinny (almost too skinny) but fit, waist length very curly dark brown hair, cute and pretty with striking facial features, easily 32B and maybe a size 2..but not quite a 4 (I raised my two daughters as a single dad years before so I know about these things). I was on a solo backpacking hike and met her during that hike (she was also backpacking). As far as how I felt?…well, I really didn’t think about her but did notice her easily among the group she was hiking and hanging out with at the time. The whole situation just happened; I wasn’t out looking to have sex with someone less than half my age…it just happened.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was backpack hiking along a long-distance trail for 10 weeks. Beginning at week 2 (maybe 10 days in), I began to leap-frog a group of young college folks for several days; 6 women and 2 guys, later joined by another guy several days on. Whenever I’d take a lunch break or stop for a rest, it seemed like we were consistently crossing each others paths, and would say hello to each other and chat about things we saw, where we were headed for the day, weather conditions, the last trail town and where we ate while there, where we were all from, and gear. Several days on, I stopped at a campsite on the trail late in the afternoon and figured I had the entire place and shelter to myself. Lo and behold, just after finishing dinner and getting ready to settle in for a quiet night, into camp walks the group. I had a small campfire going and was getting ready to open my book and read (headlamp); obvious change of plans were in order. So, I graciously moved my sleeping bag and pad over to one end of the shelter and let the youngsters set up inside; a few put up tarps outside and set up there. They were very chatty and I joined them while they ate and hung out. The skinny girl in the group introduced herself to me at one point as we hung out together and we exchanged the basic background info. Turns out Lee is also from my home-state and we both shared a love for the hometown sports teams and whatnot. I told her about what I do for a living and she told me about her time at university and what she wanted to do upon graduation. In my career I’ve worked with many college students on their internships and so I can relate pretty well to them. She and I seemed to make a good connection while talking, but we didn’t get personal beyond do you have a family (me) and how many siblings do you have (her). At the time, I wasn’t thinking about sex with this vibrant young woman, but I would be lying if I said I wasn’t checking her out either. Anyway, it also turned out that Lee had set her sleeping gear up next to mine in the shelter, which at first I was a bit uncomfortable about at the time, but I just got into my bag after a while as did everyone else. Everyone was still kind of chatting with each other as were Lee and I, and without warning the young lady looked me in the eye and whispered to me straight out of the blue “You know, you are totally hot”, then laid her head back down. I was totally stunned and could not utter another word except for a stuttering “thanks”. Fortunately it was dark enough where my look of absolute shock wasn’t evident. I laid in my bag, half expecting to be suddenly jumped by her; but fell asleep while I waited for what turned out to be nothing but words from a really pretty flirty girl. I probably slept 3 hours that night and got up while still dark, gathered my gear, ate a quick breakfast snack, and got going.

The cycle of leap-frog and chance meetings with the group went on for a couple more days. I mentioned at one point to a couple in the group (not her) that I was going to take a couple of days off, or “zero-days”, at the next town for some rest, resupply, a nice shower or two, and a nice soft bed. The couple told me they all intended to stay overnight at a local hostel in the same town, then onward the next day, and that we might run into each other. Sure as clockwork, as I was enjoying a big, greasy burger at the local diner and chatting with a couple of other familiar hikers, in walks the group! I was acknowledged by them as “that sexy man that hikes really fast”. I was a bit embarrassed by that announcement, but didn’t think too long on it. After some time, the group said they were getting some beers and invited me and another couple I was chatting with to join them at their hostel for a backyard campfire with others. I joined them and found myself hanging out with a lot of twenty-somethings, a handful of others closer to my age, drinking PBR and just enjoying the scene and banter. After about an hour or so I decided to head back to my motel room nearby and said goodnight and happy trails. As I was walking away, Lee stopped me and asked if she and a couple of friends could use the shower in my room; the shower in the hostel was too “gross”. Staying in the spirit of the hiker community, I said sure. I would be lying if I told you I didn’t begin to have an anxiety attack over coeds running about my room naked and using the shower, but I thought “be nice” and “keep it in your pants” and ” god, I hope no one hits on me”. Lee showed up with 3 of her other female friends. No orgy’s were to be had as they took their showers, used up all my towels, made a mess of my bathroom, and came out to sit on the porch outside the front door to chat about whatnot while the next was showering. Lee was in full chat with me and began to hit on me with straight lines like “You know, it’s been a while since I’ve slept in a real bed” and this zinger: “is this your own room?”. It had become clear to me what Lee was doing, and for some minutes I thought of whether or not I should allow the whole thing to continue. However, and at the same time, her hits and the idea of bedding this very sexy, cute, lively young woman made me aroused; she sensed this (she kept looking at my lap; yes, I was getting aroused). It seemed like forever until the other ladies were heading back to the hostel and Lee and I were alone, quiet. I stood up to go inside my room, my hardening penis very evident inside my shorts, and Lee stood up and without invitation followed close behind me into my room.

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? Now, you also have to understand that I hadn’t had any kind of sex for at least 3 or 4 months to that point. I was not seeing anyone regularly, but did have my “friends” with benefits. And, there was this very pretty young woman standing in front of me, looking at me, licking her lips, and obviously looking for a hookup with me. I’m 6’2″ and weigh 205 lbs. on a bad day, so that being said I’m also a monster next to Lee. But she had me falling to my knees without saying a word; I felt powerless, but I was extremely nervous about the next move. I froze.

Lee came up to me, put one hand on my now very hard cock through my pants, reached up with the other hand to the back of my head, and pulled my face into hers for what was one of the longest open-mouthed kisses I’d ever experienced. During a moment of catching our breath, she said “I’ve been hoping to corner you since I first saw you, but I’m not a slut.” I told her in the most sincere way I could muster that the thought hadn’t crossed my mind. I knew at that moment that I would have to be leading the action. We kept our lips locked and just felt each other up for a while. I’ll never forget how smooth and soft that skinny, bony body was. We eventually had our clothes off.

I began by kissing her shoulders and neck, then down onto her small chest; played there for a while, then down to her inside thighs. At some point I chewed a viagra chewable (hey look, I’m always prepared!). Then I laid her on the bed and began licking and sucking on her little pussy and ass with her legs all the way back. She looked like she normally shaved everything, but had grown some stubble while hiking; I remember that she tasted sweet, salty, and just a tiny bit funky, but very much like a woman should. I made her get on her hands and knees and licked and sucked her pussy, asshole, and sweet little buns for what seemed like a very long time, just having fun making her totally freak out. I remember her being so wet, and so horny, and grabbing my head and pushing it into her crotch. At one point I had her on her back again and I put my penis inside of her with very little trouble because of her lubrication, and from there I just remember having a fuck-marathon until sunlight the next morning. At some point she learned that I had been “fixed” (vasectomy) and that seemed to really rev her up. I know I came buckets inside of her beautiful body a few times, given that at some point we covered the sheets with an extra blanket to lay on later. I know this might sound fucked up, but the best part of the session was the several times I held her against me with her legs over my shoulders, her arms around my neck, me inside of her and standing up holding her little ass while fucking and watching myself in front of a mirror. Very hot indeed!

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? We did fall asleep, at sunrise. We slept for a bit then got up to join the day. She confided that the 3 girls she was with earlier knew that she wanted to hookup with me somehow, and that the guys had no idea what was going on. She then got up, went to the room door naked, opened it and dragged in her pack and gear which one of her girlfriends had left next to the door earlier. I asked her what was next, and she said that the others think that her brother and sister were coming in to town to visit her for a couple of days, and that she would catch up to them on the trail. Long story short, we spent two more entire days and nights together, mostly exploring each other, fucking, running resupply errands together, eating some good food, and fucking some more.

The third morning we both got up and got moving on the trail again. We hiked together for three days, stopping to fuck at least a few random times, sleeping and fucking in the woods at night, and working to catch up to her group, which we did. I almost couldn’t contain myself when we finally came upon them at a campsite, she yells out “Hey guys! Look who I ran into while chasing you down!”

We bivied separately that evening, but we promised each other we’d hook up again after we exchanged contact info. The next morning I got up very early in the dark, packed up, and moved on as hard as I could for 5 straight days before stopping in a town for rest, trying to put distance between me and the group, and Lee. It took me that long for everything to marinate into my brain, what I had just been through, and what Lee had been through with me. I convinced myself that love was not an option as our age gap was too much, but Lee was on my mind nearly every minute of those 5 days. I did not see her again during my hike, but did chat with her on our phones about a week later, finding myself about 4 days hiking distance in front of the group before they finally got off trail and went back to their normal lives. About 3 months later, we did hookup one more time as I was in her school’s city and just called to say hey; she immediately wanted to get together and we did for the 5 days that I was in town. The sex was just as hot. We’ve stayed in touch since; she now has a steady boyfriend (whom I’ve met!) and I a girlfriend that I live with (my own age, whom Lee has met!)

I enjoyed my time with Lee as a sex partner. She has since graduated from university and has a great career started. We’re glad we met each other, and neither will ever forget what we had/have together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Sterilization, We bathed!

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, I was feeling lonely, Submission / Relinquishing power, Making new friends

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? Somewhat

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 actually told my best friend about it, and my current girlfriend. My buddy was more concerned about what I might have done to this young woman. My girlfriend (we live together now) was not concerned; she knows I’m not looking for a third helping in that relationship.

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

Did you get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? One of the best lovemaking experiences of my life! And I made a very unlikely but very loyal friend to boot.

What was the WORST thing about this hookup? Getting over Lee. That was very tough. She is/was a very beautiful young lover, and thoughts of her got into my head for a long time. I knew I had to get over it, and for the most part I guess I did. But I still think about her, and those times, often.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am more careful about getting hit on (I still do), and put it all into the perspective that we’re all just human, and the instinct for sex is human nature.

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

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

Anything else you want to add about this hookup? It was just another of the hundreds of experiences I’ve been very fortunate to have had in my life. No regrets!

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? Be Careful!

What do you think about the Casual Sex Project? I had to get this off of my chest. Very therapeutic. Thanks!

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