Satiating Send-Off Sex

by Travelling Man

What’s your gender? Man
How old are you? 48
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Management
What’s your current relationship status? Single
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)? Dozens
How many hookup stories have you here posted before? 1

Satiating Send-Off Sex

How long ago did this hookup happen? About 15 years ago

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

How would you best classify this hookup? One-night stand

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? Else (pseudonym) was a German – American who worked for me in our US and then London office. She was more American than German but had that highly educated straightforward German mentality. Wicked smart, very high drive, ambitious as hell.

Physically, she is about 5’8”, and had been a competitive D1 volleyball player in college. She was about 28 at the time and hours on planes and in front of computers had softened her a bit but she was still “quite fit” or “easy on the eye” depending on whether you were a Brit or Yankee. She also was/is always impeccably dressed and brings a strong shoe game.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had worked for me for several years and, as I noted above, she was an attractive woman both physically and intellectually. I had never detected anything between us as she was very professional. Her Leaving-Do, to celebrate her leaving the firm and taking a job in Berlin, was winding down from its raucous heights.

Else, another young woman, and I started walking home as we all lived in the same direction. We dropped off our third wheel and continued on. My place was next and Else’s about four blocks on. It was late and I offered to walk her to her place and she thanked me but asked to use my restroom first (the after dinner pub restrooms were nasty and I am sure she skipped them).

We were still enjoying the night and it was ‘young’ so I poured myself a scotch while she used the loo. When she came out she claimed “no fair” and demanded a nightcap as well. We sat and drank – one became two which became…

At some point, she was rubbing my back and I was massaging her feet. It was now incredibly late and I finally stood up and told her she had three choices, that “I can walk you home, you can use the guest room, or you can join me in bed”.

She looked at me, smiled, and asked: “is there really a choice?” I told her there is always a choice. She started walking down the hall to my room while shedding clothes.

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? The sex was a drunken, sloppy, carnal buffet. And a delicious one at that. By the time we got to the bed, she was naked but I was not. She sat down and we kissed for a minute as I shed my clothes.

Then, I pushed her gently back onto the bed and, grasping her calves, began to open up her body to me. I dropped down and started nibbling her, flicking her clitoris, and tonguing her vagina. Every time my fingers touched her vagina, she tried to push herself down on me so it was clear she was craving penetration. Feeling contrary and a bit mean, I teased her by not fingering her and backing my tongue off every time she was close to orgasm.

At one point, when she was particularly on the edge, I stood up and jammed all of my cock straight into her. I have an average length penis but it is very thick and oddly thick at the base. I sank all the way into her and she just shuddered and came. It was pretty erotic to see her stomach convulsing in orgasm from my sudden penetration.

She wrapped her legs around me and started rocking on me and pulling on my ass in a universal sign to fuck her harder. I grabbed her behind the knees and spread her out in an obscene display of sexuality. She was a very sexy woman with nice firm breasts that were rocking back and forth and a shaved vagina that allowed me to watch my cock letting loose a salvo of full withdrawal thrusts. She was really giving positive feedback so I decided to tease again and fully withdrew. As she started to protest I dropped down and began my tongue lashing again. I alternated this for some time as she had several orgasms. I was pretty drunk so cumming was going to require a focus on my needs but in the meantime, we were both having incredible fun.

At some point, I introduced ass play and she was very verbally into it, as in “god yes, fuck my ass!” into it. So, the next time I stood up to fuck her I started easing into her ass. We did not have lube and I am very thick so I thought it would be difficult. No such issues, as I slid right in. By now I was pretty worked up, balls deep in her sphincter, and she was getting more specific about how I should fuck her. She clamped her muscles down on my cock and I just exploded.

I was incredibly drained and went to clean up (anal requires hygiene). I crawled into bed next to her expecting her to be asleep but she pulled the covers back and scooched down and began to fellate me. She sucked me for a while in a gaudy vulgar manner – loud sucking, humming, stroking, slapping her face with my phallus, and dirty talk. It was spectacular.

Eventually, she climbed atop me reverse cowgirl. She had an incredibly sexy ass. It was the only big part about her – NCAA D1 jumping muscles as the base and a few scant pounds since then to give it a little shimmer and shake. She was pulling up and crashing down on my cock, literally grunting each time our bodies collided and my semen was leaking out of her ass.

I wasn’t going to come again so she rode me to her satisfaction, turned around to remount me, and promptly fell asleep atop me. I let her lay there as I softened and also fell asleep. I woke up about 45 minutes later still inside her but now hard as a rock and oddly close to coming. I tensed my muscles, thrust a few times, and ejaculated in her. Then went back to sleep.

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 completely overslept. I was late to the office and she was late for a coffee.

We have stayed in touch and hooked up once in NYC and for an incredible weekend in Berlin but that was years ago. She is now the CEO of a major German company and prominent in the business media and conference speaker circuit. Married with a child now. We remain professionally friendly.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

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? She is a dynamite person. Neither of us ever had a thing for each other but we are both fine with casual sex. I think the shared experience gives our professional relationship an extra facet.

What was the WORST thing about this hookup? None!

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I definitely perfected my teasing methods that night. I still use them.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? Oddly compelling site

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