On The Road Sex



What’s your gender? Man
How old are you? 53
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? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50
How many hookup stories have you here posted before? 0

On The Road Sex

How long ago did this hookup happen? 28 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 more than 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? K was a very attractive woman in her mid 30’s. She had a great body and wonderfully full breasts. We worked together which is how we were friends. She was also in, what vaguely seemed like an unhappy marriage from the outside. I had a huge crush on her and was very turned on in her presence. As a result, getting along with her was easy for me. There was also a significant amount of “ low grade” flirting that occurred between us, the sort of interaction that one could easily and effortlessly back away from if anyone misinterpreted.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Through work, I had been tasked with assisting an out of town branch of the company I worked for. As we were the regional headquarters, we had more resources that could be implemented for the project. They had rented me a vehicle & told me to load it with gear. I would have K as my passenger as she would be on the project too fulfilling another capacity. The drive to the other city was extremely uneventful with the two of us having a little conversation about not much of anything. In fact, K was, if anything, slightly more cold toward me then she typically was during our other interactions. As such, I assumed that my desires and fantasies about her would remain just that for the duration of this trip. We checked into a hotel with two separate rooms. The hotel, in its genius way, had given two adjoining rooms. The kind that could easily be separated into single rooms by keeping the two doors closed. This was likely the final crucial detail that allowed what was to later occur between us.

We had driven up late on a Sunday evening in anticipation of starting first thing Monday morning for a five-day stint in the branch office. As such, we both got our room keys and quietly checked into our rooms and called it a night. After work the next day on the drive back to the hotel we discussed what we would do with our evening. As I had traveled numerous times in the past for work with this company, I had learned to find ways to entertain myself in the evenings off in a strange town. As I had a decent size vehicle I was able to bring a small VHS player that I would hook up to the hotel room TV. I would rent some movies prior to leaving town so I would have something to watch in my room. There was also this trick that involved bypassing the cable box in the hotel room and running the cable feed directly into the VCR. This would allow you to get the paid channels which, crucially, involved some of the porn channels available. On the drive back to the hotel, I discussed with K what we should do that evening. I suggested going to get some beer, have pizza, and watch a movie, and that she was welcome to join me. She seemed to be enthusiastic about this idea. We basically hung out in my room, talked about nothing in particular, and drank beer. We never actually started watching one of my movies. At some point, I joked about how it was possible to watch porn on the hotel TV if one wanted, however, you had to pay for it and it would go on your bill. I then explained how Hyatt figures out a way to bypass this method using my VCR. She instantly became so intrigued with the idea that there was the possibility of watching porn, she went on to explain how she’d actually never seen it before but anytime there were sex scenes in an R rated movie she wished that things would “go further”. I was walking the tightrope between being cool about showing her a porn channel and not appearing to be a total pervert. We flipped through the channels until we arrived at the porn channel. They showed the usual acts of oral sex and various acts penetration in numerous positions. It was clear by her silence and her focus on the TV that K was clearly mesmerized by what she was watching and, as it soon appeared, is getting very turned on.

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? Having this beautiful woman in my presence and watching this scene on my TV had me really turned on. My cock was becoming extremely hard. I was working from the assumption that K would not want to “go anywhere” with me, so I was really interested in getting myself off. All of a sudden K turned and glared at me, my first response was that she was angry with me for showing her this material. That was far from the truth. She looked at me and walked over and basically started kissing me passionately. Seconds later we were tearing each other’s clothes off and rolling on one of the beds in the room. We were both naked In seconds. K went down on me and took my almost exploding cock in her mouth and began performing an amazing act of fellatio on me. There were goons of spit dripping down my shaft as she took me in her mouth and stroked me with her hand with complete enthusiasm.

I could feel myself about to cum, so I abruptly stopped the process. I didn’t want things to end there. At that point, I flipped her on her back and began performing cunnilingus upon her. She had the sweetest tasting pussy I think I had ever had. I could hear her deep moans as she squirmed on the bed in pleasure. It seemed like seconds later that she shuddered to orgasm and her pussy was drenched. I couldn’t believe how turned on I was and how ready I was to fuck her.

As I moved away from her pussy, I kept her legs spread and basically moved up her body until my cock was parallel to her soaked opening. For a few seconds, I rubbed the head of my cock against her sweet soaked pussy lips and then slowly thrust into her just an inch or two pounding in and out. After maybe 20 seconds or so, I thrust myself deep into her. I was thrilled with her tightness and wetness, and the fact that she would clench her muscles and tighten her pussy on my cock was mind-blowing. We kept fucking and I felt like I was going to shoot my load but wanted to make things last. I promptly pulled out and grabbed K by the hips. I spun her around and lifted her onto her knees ready for doggy style. I then thrust myself into her pussy and continued pounding away, all the while still hearing her moans as they got more high-pitched and more frequent. I knew that a second orgasm was soon coming from her. Once again I could feel her shuddering with pleasure and basically screaming in delight. I continued to pound away, but I wasn’t going to last long and soon exploded deep inside her, filling her with my load. We then both collapsed on the bed, drenched in our own sweat. Our friendship has certainly taken a different direction! For the rest of the week, while we were away, our evening activities became more intense. And our “recreation” continued for sometime after we returned home.

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 were both incredibly satisfied with how things had unfolded that night and reaffirmed that over the next few nights at the hotel. One thing she told me was that my erections were incredibly rigid, and as a result, I was able to pleasure her in a way she was not used to. As I understood it, her husband was unable to perform in this manner.

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)

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

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? No one, as we did not want anyone from our place of employment to find out about it for obvious office politics reasons. Also she was, by her own choice, unwilling to let her husband know. Additionally, our professional community was fairly small and if word got around it might be damaging to the both of us.

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? Not at all

What was the BEST thing about this hookup? Having amazing sex with someone I both liked as a friend and found amazingly attractive.

What was the WORST thing about this hookup? That it couldn’t last

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No, not at all.

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

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

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