In Need, Indeed



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (currently in college)
What’s your occupation? Writer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 35
How many hookup stories have you here posted before? 3

In Need, Indeed

How long ago did this hookup happen? Last summer

What was your relationship status at the time? Single

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? Mid-fifties woman, average body type, hair dyed the color of autumn red. We met through Craigslist; I was feeling frisky and had posted an ad looking to provide oral sex to a woman. She told me she was in need: her husband hadn’t given her oral attention in a year, and she had no sex in over 6 months.

No sex in six months? No oral in a year? Oh, honey, we have to fix that. We settled on her coming over the following Tuesday, as she had some free time and he wouldn’t suspect anything.

Honestly, I wasn’t that attracted to her, and she certainly gave off a decidedly lower-socioeconomic vibe (which honestly was one of her more noticeable traits). But, I wanted to help her out after hearing her tragically sexless story.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She was a little nervous when she came over, but that was understandable. She wore a fake-looking leather jacket, which I thought was odd given the July heat. She slipped it off after ten minutes of talking on the sectional, leaving her in jeans and a t-shirt.

I don’t remember much of the small talk, but I do remember her making a comment, “I don’t know if I’m more nervous or excited, we just met but it’s been so long…” and there was almost pain in her voice.

“Let’s go get you taken care of,” I suggested. She stood up quickly like she had sat down on something sharp. I began to lead her back to the bedroom; she asked for directions to a bathroom to freshen up, so I pointed the way. While she was away, I stripped down to my boxers and sat on the bed to wait.

She emerged from the bathroom still wearing her shirt but had stripped down to a plain white cotton pair of panties. She sat down beside me. We continued chatting, and I started idly stroking her leg. I bravely started working my way up her leg, and she told me how nice it felt. When my fingers found the fabric, she moaned a little and leaned in to kiss me.

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? We made out for a minute or so. We weren’t very kissing-compatible and I could tell she was a smoker, so I began kissing my way down her neck while rubbing her leg. When my fingers found her moistness, she almost jumped off the bed.

I got the hint: I slid her panties off and was face to face with a neatly-manicured natural red patch of hair, and smooth labia with tiny yet angry clitoris peeping out.

Did I mention I love to lick pussy? Seriously, it’s one of my favorite things on earth, and knowing she was as in need gave me added incentive to really go for it. I took my time, building her up and then letting her come back down before finally I had her grabbing the sheets and my hair as she powered through a deep orgasm.

I let her gather herself slightly, but then I was right back to work, and she quickly reached her second orgasm. Then, I suggested she ride my face for a bit, and she could watch me jerk off.

It took a minute to establish a rhythm and proper positioning, but she was quick to find her third orgasm. As she began nearing her fourth, I let her know I was about to shoot a geyser of cum and asked if she wanted to see.

“Give me all that cum,” she begged, quickly sliding her way down my body and swiftly putting me inside her. She was so wet and I went right in with one stroke and didn’t stop until I hit her cervix. She started riding the hell out of me, and seconds later I told her I was about to cum. She gave a loud moan, and I dumped what felt like gallons of cum into her tightness.

That was one of the most intense orgasms I had ever experienced. I wasn’t anticipating having sex, much less unprotected sex, much less cumming inside a stranger, but holy shit it was so hot.

Eventually, she collapsed satisfied on the bed next to me, legs slightly spread and her knees up. A giant gurgle of semen appeared, and slowly started trickling down her asshole. “So much cum,” she said and started fingering herself, index then index and middle. Then she slowly removed her middle finger from her pussy and slid it into her ass, using my cum as lube.

Even though that gigantic orgasm was still washing over me, seeing her finger herself got me rock-hard. We started to fuck in missionary; she started sliding both fingers into her asshole. Five minutes of hard pounding, and another orgasm for her, and I left another load as deep as I could inside her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? “Don’t worry, I’m clean and fixed, ” she told me after the second round. Probably something we should have led with, but I wasn’t that upset.

Then there’s the kicker: “He wants me to fix dinner by six tonight. I’ll be full of your cum while I’m cooking. Maybe I should give him some…”

We met up a few more times. I’d lick her to as many orgasms as she needed until she’d beg for my cum and I’d stick my rock-hard dick inside her and fill her the rest of the way up. Sex itself was never that important; she wanted to get licked to orgasm, then she wanted my cum inside of her. That was all it ever was.

Visits became far between, and we lost touch when I got a new phone.

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, Thought it was an important experience to have, I was feeling lonely, Revenge / Getting even, 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? Somewhat

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 Y’all!

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Knowing I made her a happy woman, after months of neglect. Also, duh, that unexpected gigantic orgasm I had.

What was the WORST thing about this hookup? The initial shock of unprotected sex.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope, I’m all for an understood agreement between consenting adults.

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

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

What do you think about the Casual Sex Project? I’m a huge fan! It’s inspiring as it is educational. Ever wonder if anybody’s made a connection through the site and written about it?

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