Road Trip With FWB

by ssksubby

What’s your gender? Man
How old are you? 45
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 occupation? Government
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Road Trip With FWB

How long ago did this hookup happen? 2 months

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 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? C and I have known each other for 14 years and have hooked up numerous times in the past, but not for a couple of years. C is 48 with large 38DD natural tits and an amazing ass with a tattoo on her lower back. We met at a work party and consider each other great friends.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? C was at an out of town work event where I just happened to be for my work. We made previous plans to meet for dinner and drinks after her event. We hadn’t hooked up in a few years and we flirted with each other while talking about our past sex sessions. C was wearing a short skirt and knee high boots. During dinner, I placed my hand on her thigh and slowly moved it under her skirt to find out that she wasn’t wearing panties. I slowly caressed her shaved pussy, inserting two fingers in her wet pussy. I brought her to an explosive orgasm after which she sucked her cum off my fingers.

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 dinner, we went back to her room. Once the door closed, she led me to the bed and sat me down. She then slowly removed her clothes and got down on her knees, unbuckling my belt and removing my pants. She then took a bottle of lube out of her purse and squeezed some onto her hand. She took my head into her mouth and slowly sucked on my cock as she stroked it up and down. She did this for about ten minutes. Then we climb onto the bed where I slid two fingers into her wet pussy and my thumb into her ass. She was squirting everywhere, soaking my face and chest. I kept up the rhythm, making her collapse and scream at me to give her a break. I straddled her chest and wrapped her big tits around my cock I slowly tit fucked her. After five minutes of this, I was ready to explode. I shoved my cock as deep as it would go down her throat and squirted a good load of my cum into her mouth. She swallowed it all. C kept sucking my cock and kept me hard. She then straddled me, slamming her pussy up and down until she came 3-4 more times. I flipped her over and started fucking her doggy style. She begged me to fuck her ass hard. I lasted a couple of minutes before cumming in her ass. We were both spent and lay side by side, cuddling and slowly stroking each other. We ended up have sex 3 more times that night along with shower sex in the morning .

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 exhausted from our night together. We both we glowing and flushed. We both decided to plan another adventure in the near future and not wait a few years. C will always be a dear friend.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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

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? Our close sexual connection to each other. No inhibitions between us. We feel safe with each other

What was the WORST thing about this hookup? Only one night

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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? No

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? Casual sex is fine if no one gets emotionally hurt.

What do you think about the Casual Sex Project? It is a pretty cool project.

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