by

What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
What’s your current relationship status? Widowed
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Fun. Adventurous. Experienced.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 9

The Best Tip I Ever Received

How long ago did this hookup happen? Summer 1986

What was your relationship status at the time? Single

How would you best classify this hookup? First of many

How long did you know the person before this hookup? For less than a week

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 was beautiful. She had naturally blonde, wavy hair that hung nearly to her waist. Her eyes were almost the same blue as the water at a British Virgin Islands beach, and the whites were clear as the finest of pearls. She was 5’4” tall, weighed 115 lbs., had small C-cup breasts, and a waist that was obvious but not overly pronounced. She had normal sized lips that oozed sensuality without looking like she was actually inviting a come-on. She had an easy smile that seemed constant, whether talking with someone or just driving down the road by herself, or even when she read; and she had perfect teeth.

C and I were introduced by our chiropractor because she was having some problems with her car and I was a home-based mechanic. She and I just happened to have our appointments sequentially that afternoon, so it was an easy intro by the doc. There was an instant attraction between us, even before he introduced us. We exchanged numbers after she told me what problem she was having and I told her that I could fix it within the space of about an hour. She waited until the doc was done adjusting me so that we could talk some more in the parking lot.

We talked for about 20 minutes or so before each of us had to leave for other obligations. While talking we realized that we had several likes and dislikes in common, as well as similar political, financial and religious values. We were both happy to have met, and had a really nice hug before we parted ways, knowing that we would see each other the next afternoon when she would bring her car to me for repairs.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? C arrived at my house around 4:00 p.m. the next afternoon (a Wednesday), and was surprised that I had my tools and equipment ready to go to work. We chatted as I worked on her car for the next 50 minutes. Our conversation was really mostly small talk but had a flirtatious vibe that was steadily crescendoing throughout. After I finished repairing her car, she was surprised that I automatically checked the fluids and tires, so she commented that she was going to have to give me a little extra for giving her more service than she expected. I told her it wasn’t necessary because that was simply what I did for everybody, whether they were there while I worked or not. I wrote up a receipt for the work and parts, and asked her if she wanted to go inside to write a check and have an iced tea. So, we went into the house, she sat down at the kitchen table to write the check while I poured a couple large glasses of freshly brewed iced tea after washing my hands.

We sat talking over the tea for the next hour or so, simply getting to know each other a little bit more, and of course some more flirting, which elevated the sexual tension very nicely. When she asked me where the bathroom was, instead of giving her directions I led the way, telling her that, while she was using the loo I would change my clothes and meet her back in the kitchen in about five minutes or so.

I was just starting to put on an Oxford style shirt and still had the fly open on my jeans, so I could tuck it in, when she opened my bedroom door. My first reaction was to turn slightly away from being mildly surprised that she was that bold, but then I just said to her with a little snickering smile, “This is interesting. Did you forget the way to the kitchen or just want a tour of the house?”

She said something along the lines of, “I don’t think I’m lost; but I’ll take a raincheck on the tour.” She then walked over to me and said, “I think it’s time for your tip.” The she stood up on her tip toes to kiss me (I was 6’1” tall). We embraced and made out standing up for a few minutes before she reached with her left hand into my boxers and started fondling my rising penis, which took all of about 20 seconds to reach full hardness. She expertly used her hands to stroke my cock, knowing how to read the sensitive areas from even minor reactions. I unbuttoned her blouse in order to get to her beautifully mounted breasts, which had nearly flat, dime sized nipples that had a peak almost perfectly in the center of each of them, almost like a partly melted chocolate baking chip.

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? I just started to move from her lips around to her ears with my kisses, with the intention of kissing down the side of her neck to her breasts when she stopped me by pulling away, saying, “No. This is YOUR tip. I can wait for mine until another time.” She then dropped quickly to her knees as she pulled down my boxers and jeans in one motion, and took my cock into her mouth before she was even able to get her hands back up from disrobing my groin. C gave incredible head! She controlled the stimulation in order to make me last in her mouth for more than a half hour before asking me if I really wanted to cum yet.

I told her to do what she wanted because I could cum any time but didn’t want it to end too soon. She smiled again as she looked into my eyes and took my 7½ flagpole almost to the root while giving a throaty hum. She kept going long enough that I had to sit on the edge of my bed before my knees got too weak from the beautiful blowjob she was administering to my now aching cock.

Finally, after more than an hour long blowjob she said she was ready for me to fill her mouth, and started bobbing up and down on my dick fast and deep for the next couple of minutes, all without breaking eye contact. I didn’t have to tell her that I was ready to cum because she started humming hungrily, which just shot me completely over the edge and caused me to shoot my semen into her mouth for the next 15 or 20 seconds, constantly pulsing with more semen than I expected, to the point of some of it leaking out of the corners of her mouth because she couldn’t swallow quickly enough to catch all of it, but she sure did try, and all with a hungry smile on her lips and in her eyes.

After I was finished cumming, she wiped her mouth with the back of her left hand and said, “I’ll let you do anything you want the next time I come over. But I want to know something, how was your tip?”

I stood up and told her, “There’s no charge for any of the work today.”

She said, “I’m not a prostitute, and I already have the check written out. This was just your tip.” She then pulled up my boxers and jeans as she stood up, giving my nearly flaccid cock one more kiss before putting it away in my drawers, then gave me a wet kiss, on which I could taste the salty residue of my cumload.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? C and I stood there and made out for a few more minutes before I said that I was thirsty and needed to get back to my iced tea. We sat down at the kitchen table for a few minutes and talked, setting a date for that Friday evening. She left, and I made my dinner.

After that incredible blowjob I knew that she would likely be a wildcat in bed, and having been told that I could do anything I wanted the next time she came over, I knew we would probably be naked before going to the movie. She didn’t give me her address because she still lived with her parents, so the next several times we were together she came to my house straight from work.

I hoped that we would be able to build a friendship on top of the sex, and we actually started dating pretty seriously after the first several hookups, eventually leading to propose marriage after about six months of fantastic times, in and out of the bedroom. She said yes, and we stayed together for another five months until she was killed in a car crash. I’ve often wondered how our relationship would have turned out, thinking that it would have been good because we really talked about everything, and had an understanding that we could fuck anybody we wanted as long as it was with protection, and that we would tell each other every time. We had several threesomes with other women but she was scared to have two men at the same time.

How do I feel about her today? That’s easy: I love her and miss her. We were good together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), 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? Never said anything to anybody about our first time together.

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? What an amazing oral talent C had. I couldn’t believe how she could bring me to the brink of ejaculation and then drop it back to just enjoying a nice blowjob, almost as if it was just starting again. This happened more times than I could count over the nearly 1½ hour blowjob. To this day it was the longest blowjob I’ve ever had.

What was the WORST thing about this hookup? Trying to stand up with my knees buckling from the sensations of a magnificent blowjob. But I am NOT complaining!!!

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? I can still see her smile today as I started filling her mouth with my cum.

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? I have enjoyed casual sex for over four (4) decades, except for the few times that I have been in a monogamous relationship. I feel that CS is one of the most underrated methods of social interaction, while at the same time being one of the most, if not the most, overrated ways people use to try to improve their self assessment/esteem. It is possible to go from casual hookup to serious relationship, but this is uncommon and an unrealistic expectation. That being said, for the most part I would rather have several fairly regular sex partners who are trusted, loving friends than a monogamous relationship. The reason being is that there is less emotional baggage with CS partners, even though the intensity of the relationships can potentially be as deeply intimate, so long as the ground rules are clearly understood by both/all, and an attitude of mutual respect and responsibility for each other’s safety is maintained.

What do you think about the Casual Sex Project? I enjoy it very much. I read nearly all of the new posts every couple of days. It is also a way for me to bring to memory former lovers, FBs, FWBs, etc.

I wish we could comment and read comments natively on this site. There are those of us who do not use Facebook.

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

Story Views: 4,401