Cross CUNTry Roadtrip

by Tommber

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? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Retiring Executive
What’s your current relationship status? Widowed
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Adventurous. Exciting.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? Several

Cross CUNTry Roadtrip

How long ago did this hookup happen? early August 2016

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? M is 5’8” tall, brunette with natural reddish highlights and just the slightest hint of graying; her hair hanging to her mid back, mostly straight with just a bit of natural wave. She is slender but not skinny (just the perfect amount of softness without being even slightly overweight); has full but not large lips; a sweet, alluring smile; very clear and smooth complexion; and the darkest green eyes I think I’ve ever seen, with supremely clear whites, and she sports heavy but firm B-cup breasts. She was dressed in a pale pink sundress with pastel green flower print, and comfortable looking flat sandals. And, since she wore a rather nice wedding set on her left hand, I assumed she was married, so I kept my part of the conversation on the conservative side to begin with.

We met while waiting in the bus station in Vegas. We had both been there for the weekend on business with our respective companies, and were looking forward to getting some shuteye on the ride across country. She was going home to Ohio, me to Michigan, so we had a long ride to our last mutual stop in Chicago, and decided that we would travel together and enjoy each others’ company and, she said, it would afford her some protection from any “undesirables.” And it would not look the least bit suspicious because I still wear my wedding band after my wife died earlier this year.

We departed Vegas about 1:30 a.m., with the initial leg of the trip lasting just over four hours. As we slept, we both seemed to lean toward each other, and I awoke some time later with M’s left hand on the inside of my knee. I thought I would take the liberty to place my hand on hers as I went back to sleep. We both woke up when the bus came to an abnormally quick stop, and realized that we were now fully and comfortably holding hands. We got going again pretty quickly, so she asked if I was okay with her leaning on me while she continued sleeping. I answered by letting go of her hand and putting my arm around her shoulders, gently pulling her into my side. She looked up, said, “Thank you” with a smile, grabbed my hand that was on her right arm, kissed it softly, then went back to sleep. We both slept for the next 1½ hours to our first scheduled stop, which was at 5:45 a.m. in the same time zone, where we got off the bus and stretched out a little and got some yogurt with fruit for a quick breakfast.

Back on the bus, we chatted a little bit more, and I learned that she has been happily married to a good man for more than 20 years, but that she was somewhat sexually frustrated as he had become impotent after being sick a few years earlier. She said that he would often go down on her of his own volition, and that she enjoys and appreciates it, but she loves him and wishes they could have regular intercourse, and that it had been more than 16 months since the last time he was able to have an erection. (It’s interesting how someone who would normally never talk about stuff like this with anyone opens up to one who was a complete stranger until just 7 hours earlier. I find it especially peculiar because I never asked about her love life, or even about her relationship with her husband, just general family oriented questions.)

The 2nd leg of the trip was just over a ½ hour long, and we chatted the whole time, with her doing almost all of the talking (I enjoy listening to other people’s stories.) Our next layover was just over 1 hour long, so we walked, talked, ate brunch, while waiting to get back to the ride.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next leg of the trip was over 4 hours again, which got us to Denver at 5:45 p.m. We had a little more than 1½ hours for the layover, so we walked to a local restaurant and had dinner and, of course, more conversation. M and her husband have six children, with two in college. She and her family enjoy real camping with tents and sleeping bags, which is one of my favorite activities, too. So we exchanged stories of some of our excursions through the years.

When we got on the bus this time we decided to sit all the way in the back (I felt like I was in high school again.) Then, after a few “normal” camping stories, she started telling me about how one of her daughters was conceived in the family tent while the three oldest kids were sleeping. We had some laughs, and she asked me to share some of my camping sex stories. So, the next two hours were filled with sharing sex stories. She said that she was a little bit jealous of me because she had only been with one other guy besides her husband, and that was her first boyfriend in high school. So, she kept asking me to tell her about some of my more sordid stories, which she obviously took great delight in, and would occasionally indicate that she was getting quite aroused.

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? After another 10 minute stop, we had another good 3½ hours before the next one at 3:35 a.m. Since it was late and most other passengers were beginning to dose off, we figured it was probably a good idea to cut the conversational volume down, even though it was obviously already pretty hushed. So, while we talked more we put our faces closer together, often whispering into each others’ ears. While I was telling her yet another story of a camping escapade while whispering it into her left ear, she turned and lightly bit my right ear, and told me that was enough talking, that she wanted to feel like a slut. I pulled back, looked her in the eyes, and asked her if she knew what she was saying and if she really wanted to go outside her marriage for sex. She assured me that she most definitely did by turning and reaching into my crotch, where she found my already puffy member. Then she kissed me with impudent lips, moaning softly and wantonly into my mouth. It didn’t take us long to get inside each others’ clothing. When she pulled my cock out of my pants she looked me in the eye and said that she has wanted to have a hard cock in her mouth for a very long time, and adjusted herself in the seat to go down on me. She pulled my pants down to my ankles, and commenced to giving me a terrific blowjob, and refused to come up until I shot my load, which she swallowed greedily while another man was walking back to the lavatory. She finished up just in time for him to see her sit back straight into her seat. She asked how long it would be before I could get hard again. I said I wasn’t sure but that it would be in time to fuck before our next stop. So, she went back down on me and sucked, stroked, and licked my softened prick for more than a ½ hour before it started coming back to life again.

Once I was stiff enough to call it an erection, she lifted her dress to her waist, and straddled me, and with a quick adjustment slid my cock into her nearly sloppy wet pussy. Once she was fully impaled on my spear, she asked about birth control. I told her that I had a vasectomy before my late wife and I got married, so she said, “I want you to fill my cunt up until it drips out.” While we tried to keep quiet, it was pretty obvious to the other passengers what we were doing. A young couple sitting across the aisle turned around and watched us. I just smiled back to them. I told M that we were being watched, but she said it would be okay with her if they took pictures, then chuckled quietly while kissing my mouth. We fucked for probably 30 minutes or so, she having several convulsing orgasms, before I blew my load inside her.

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 took two other opportunities to fuck on the bus, and once at the depot before parting ways in Chicago. She asked about keeping in touch, so I gave her my business card and told her that I would welcome her calls and be willing to connect when either one of us was in the others area but that I would leave it up to her. She said she couldn’t make any promises but that she might contact me. I really didn’t expect to hear from her again but she called me a couple weeks later and said she would be within 50 miles of me. We agreed to meet at her hotel, and spent two more exquisite nights together.

Who knows if I’ll ever hear from her again but I really hope I do. I told her that I will not contact her because I don’t want to risk her marriage, which she appreciates, but that I would answer any messages she leaves me if I can’t answer.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, Making new friends, Didn’t want to disappoint my partner

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? Just with her. We agreed that, while it was quite risky, neither one of us believed that it was too far out of the normal for cross country bus trips to really worry about. We also agreed that, while it was very sexually gratifying, we both would have preferred it to be with our spouses. We both know, however, that is not possible.

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? The chance hookup with a beautiful, mature lady. Who knew that the only time either of us decided to take a bus across country rather than flying, that we would have this experience? Also, being watched by a hot young couple, who later had sex in their seats while we watched and groped each other quietly.

What was the WORST thing about this hookup? It wasn’t with our respective spouses.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all.

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? We had both decided at the last minute to take the bus rather than fly, which was surprising to us both. I was surprised that a beautiful, married, middle-aged woman was on the bus, though, and that she would actually be open to a hookup with a stranger. But, at least we also became “friends”.

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? See my previous posts.

What do you think about the Casual Sex Project? I enjoy it very much.

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