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What’s your gender? Man
How old are you? 65
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Chicago
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Management Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: New Age
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Raging Libido
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? none

Surprise Bang

How long ago did this hookup happen? 1 year ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short Fling

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? I met Jen (not real name) who is 38 years old through an online dating site. Her photos were very enticing. She had long dark hair. Her face was attractive in a slutty sort of way. She exuded a “just fuck” persona. We had a few phone conversations before we met in person. I loved her voice (dark, sultry, and sensuous). From our first phone chat, it was obvious she was very open-minded sexually. By our second call, we were sharing graphic stories about some of our favorite past sexual adventures. She acknowledged having had a couple of MMF three ways. We shared pics, some of which were quite naughty. During our third call, we agreed that we HAD to meet and made a date to get together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jen came to my place. I offered to cook dinner. She showed up at the door with a very tight, short skirt and a white blouse open half way and tied at the waist. Her tits were incredible! She was not wearing a bra so her nipples were showing thru the fabric and already hard when she came thru the door. Boing! Instant boner for me! She gave me a big hug and a deep wet kiss. She said, “Fuck dinner! I want your cock in my mouth right now!”

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? So right there in the foyer of my house, she undid my belt, pulled down my slacks, and began to suck my cock! What an amazing mouth! One of the best I’ve experienced. The right amount of sucking and licking with lots of saliva! She used her hands to stroke me while she sucked the head. Within a couple of minutes, I could feel the pressure building in my nuts. She did too and cupped my balls with one hand and kept stroking and sucking with the other. She looked up at me with lust in her eyes and said, “I want your cum!” Almost on cue, my cock began to spasm and throb! “OMG! I’m cumming!” My dick must have pumped a dozen times. The head was so electric that I literally shouted! I’m sure my next door neighbor heard me. Jen kept looking me in the eyes while she drained every drop of cum. She opened her mouth to show me some before she swallowed. She smiled a very nasty smile and said, “Hey! Great appetizer! Now, what’s for dinner!”

Thanks to my now empty balls, dinner was more relaxed and fun. We took our time and enjoyed nice food and a bottle of wine. We shared some naughty stories and fantasies. One of her’s was to go to a swingers club with a hot date (me) and experience random, anonymous sex with strangers. She said that she only ate pussy one time but really enjoyed the experience, so she would love to do that again at a sex club.

After dinner, we started making out at the dining room table. Clothes were abandoned on the floor. We never made it to the bedroom. The sofa was on the way, so she bent over the sofa and asked me to fuck from behind. I had a condom in my pants pocket so managed to get covered before plunging into her wet pussy from behind. She had grabbed her ass cheeks and pulled her cunt open for me as I slammed into her. Since I had such a massive orgasm before dinner, I was able to pump away for ten minutes or so without the risk of cumming again. She was moaning loudly and telling me to fuck her harder. Eventually, she screamed that she was cumming! Her cunt spasmed and clamped on my cock so tightly that she actually squeezed my dick out of her pussy. I then turned her around and put her upside down on the sofa so I could eat her out for a while. She moaned and rocked her head from side to side and had another loud O. From the sofa to the bed, pillows and blankets were ripped off! Jen dropped to her knees in front of the bed and pulled the condom off of my cock and then literally sucked me into the back of her throat. I asked if she could please get on the bed so I could fuck her some more. She shook her head with my dick still in her mouth and mumbled, “Uh uh!” And so, about five minutes later, she got dessert! At my age, it’s hard for me to work up a second load, but this girl has a magic mouth! Wham! I came again, HARD! Not as much as the first round, but enough to elicit a nasty smile from Jen with her tongue out to display the prize. We climbed into bed and snuggled for a long while and eventually fell asleep.

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? Jen woke up early and blew me AGAIN before she had to leave for work. We agreed that our time together was fucking awesome and committed to so something even hotter again soon. We texted that day and spoke on the phone a few times during the week following this first hookup. We decided our next date should be at a sex club. I’ll share that story soon! Stay tuned!

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

What were your motives for this hookup? Fun, pleasure, horniness

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? A couple of my buddies. We love to share stories about our various sexual escapades.

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

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? Receiving an amazing blowjob from an attractive, hot, nasty, younger woman in the entrance of my house!

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No…. love it! Need it!

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? More to cum about hooking up with Jen.

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? For me, it’s an essential part of life and not to be denied. Just be kind, safe, and happy!

What do you think about the Casual Sex Project? Awesome project!

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