A Long Drive For A Weekend Of Sex

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? over 10

A Long Drive For A Weekend Of Sex

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? Judy was a couple of years younger than me. We had met in a chat room just talking in a friendly manner, which later progressed to messaging each other and getting flirty and sexual as time went on. I started calling her on the phone, and we would occasionally have phone sex with her telling me how she was going to suck my cock like I had never had it sucked before. And I would tell her how I was going to eat her pussy until she couldn’t take it anymore and then fill her with my big, thick cock and cum repeatedly inside of her. Judy was about 5’7, 140 pounds, had nice B cup tits, a flat belly, fairly nice ass, big smile, and was friendly and funny. From our texts and phone calls, it was obvious that when we did get together that we were going to fuck. The only problem was I was in southern California, and she was near San Francisco.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was seeing 4 other ladies as FWB and was seeing each of them 2 or 3 days a week, and when I found someone else that I wanted to hook up with, I would make excuses to the other 4 and go off to meet my new mate. I arranged with Judy to come up to see her for the weekend. I asked her to find a motel with a jacuzzi tub for us to lounge in. She made the arrangements, and Friday after work, I climbed in my car and made the 5 hour trip toward her house. I checked into the hotel and called her to let her know I was there. She said she would be there in a few minutes.

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? Judy showed up, and we went to a local diner since I hadn’t eaten and I knew I would need my strength. We had a casual dinner and just talked, nothing sexual, and got acquainted. We went to my room. She got out the bubble bath and got the jacuzzi going as I started to get undressed. I had been thinking of nothing but fucking Judy for the last 5-6 hours, so I had a raging hard-on. Judy looked at it and said, “Wow, is that for me? It’s bigger than I thought it would be.” I helped Judy out of her clothes, sucking her nipples as her breasts became exposed. We got in the Jacuzzi, and she asked for me to sit in front of her. She played with my hard-on by reaching around me, playing with my hard cock and my balls. We got out of the tub and toweled off. I laid down, and she began sucking me for a little bit…not long enough though. She straddled me, and I watcched as my thick cock split her large inner lips. It was amazing to see her lips push inside of her as my cock penetrated her. I told her I wanted to eat her pussy first but she said, “That’s much too personal.” Can you believe that after I told her in our phone sex that that was what I was going to do? She rode me and had a massive orgasm as I sucked her nice nipples; she rode me cowgirl style. I rolled her over and pounded her pussy until I came inside of her. We fucked several times throughout the night, and she woke me with a blowjob. We spent the weekend fucking, only leaving to eat, shower, and rest.

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 met up a few more times and fucked for 2 or 3 days at a time. She eventually found another guy closer that could come and fuck her more regularly than I could. I did finally get to eat her pussy though, and it was magnifacent

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, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Power / Dominance, Making new friends, 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? no one

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? Great sex.

What was the WORST thing about this hookup? She didn’t let me eat her right away; I love oral.

All things considered, how NEGATIVE was this experience? A little negative

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