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This post is sponsored by The T Bar.

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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? Engaged/Married (monogamous)
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? 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? 7

The LONGEST …. Ever!

How long ago did this hookup happen? 1991

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? For 1 to 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? Legs was her nickname. She was about 8 years older than I at the time of our hooking up. Legs was 6’ ½” tall, very slender but not skinny, with heavy B-cup breasts; short blonde hair cut into a flat top spiked style; weighed about 145 lbs., and had the longest legs I can recall ever seeing in a normally proportioned woman, measuring 38.5 inches for her inseam. To put this into perspective, the average inseam length for men is between 32” and 34”, and the average female inseam length is 31”-32” for regular/average height, 34” for tall, and 35”-36” for X-tall. So, you can see that Legs had a very appropriate nickname. Another thing about this lady is that she almost always wore clothing that accentuated her long, slender, muscular, shapely legs. And she had the perfect ass to top off those exquisite legs. Legs always smiled and laughed easily; was gregarious, always open to conversation; nearly always accepted an invitation to dance, whether from a woman or a man; and was a very good dancer on the club floor – she really knew how to move in a way that suggested that she enjoyed sex without really making any lewd movements. She nearly always wore just a hint of a high quality perfume that stayed with her for the entire night of dancing.

I met Legs at a nightclub about a year earlier through a mutual friend, whom I had been fucking for a few months. At first, she seemed a bit aloof but warmed up after I invited her to dance with me a few times. After that we got along well and had plenty of laughs and good dances, and even some good conversations at restaurants after hours. From the first time I saw Legs, I knew I wanted to see how well she could wrap those long legs around me. I could imagine how she would clamp them tightly around my head while I ate her out, and then around my waist while we fucked. The only problem was that she always went home alone and seemed to always turn down every guy who came on to her beyond just dancing. I had to figure this one out and win her over to the idea of getting together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The mutual friend, P, whom I had been fuck buddies with for about 8 months stopped coming to the bar, seemingly just dropping off the face of the earth. She also would not answer any phone calls. One evening I was out at the bar and invited Legs to dance. We danced a couple of songs then sat down together and talked. I asked her about P, and if she’d heard anything from her. She told me that nobody was able to get her on the phone and that she had actually dropped by P’s house one day just to say hi but, even though there was someone home, nobody would answer the door. Legs and I talked for a while about this and that, and danced another song set before closing time.

After hours we went to the diner across the road and had more conversation and breakfast. At the diner we normally sat with about 6 – 10 other people from the bar and just had good laughs and food. For some strange reason nobody but another couple came to that diner that night. So, Legs and I just extended our conversation. We got to know each other quite a bit better as we talked for about the next 2½ hours. After we were done talking and drinking coffee I walked her to her car and opened her car door. To my surprise she leaned over the top of the door before sitting into the car and kissed me on the lips, then sat down, smiled at me and told me she’s see me on the weekend, closed her door and drove off.

Saturday, two nights later, we both arrived at the bar at the same time, so we walked in together. You should have seen the people look at us, as if they thought what I wanted to happen already had and they all knew it. But Legs and I had not even discussed getting together yet. However, that was about to change.

We sat at different tables, she with the women she normally sat with and I with a mixed group that I often sat with – when I sat, that is, as I was almost always dancing with somebody. On about the second song after we sat down I went over to Legs, grabbed her hand and took her onto the dance floor. She was rather surprised that I did not offer an invitation but just assumed that she would dance and didn’t give her any real chance to object. She told me after we started dancing that she wasn’t used to being dragged onto the dance floor by anybody but that she kind of liked it. We danced several songs, and even through two slow songs. I am a singer, and tend to sing along with almost any song I am familiar with, and those two slow songs were no exception. Legs said she didn’t know that I could sing and that I had a good voice. I said, “Thank you. I wish I could sing as well as you dance.” She blushed slightly and said she needed to sit down for a while. Now, to my surprise, she took my hand and led me past the table she was sitting at and to an empty table away from the dance floor. We talked about several things, danced a song or two, sat and talked, danced, etc., etc. As the night wore on we started talking about relationships. She said the reason that she always turned down men’s advances is that they all seemed too anxious to get into her pants, and didn’t seem like they cared a blink about her; just that they all just wanted to get their dicks wet between her long legs. One thing I’ve learned is that when a woman is venting, just let her vent. It’s not just so that she will open up for me, but it will always lend to some sort of more intimacy in the future, even if it is just a trusted friendship. And that’s really where I thought this one was going to.

The next time we got up to dance she surprised me again when the slow song started playing. She got real close and wrapped her arms around my waist instead of my shoulders where she normally rested them. I had my arms above hers and around her waist as we danced, looking eye to eye for most of the first song. At the beginning of the second slow song she stopped dancing, grabbed my hand and said, “Let’s get out of here.” That’s when I really suspected that she didn’t just mean to the restaurant and then split. We did go to the restaurant, but this time she rode in my car and we went to the drive-thru window to order.

As I pulled out of the restaurant parking lot I asked her who’s place she wanted to go to. She said we should go to mine because her 15 year old daughter was going to be coming home late that night and she didn’t want her to walk in hearing us “doing the wild thing.”

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 ate the food during the 20 minute trek to my house. When we got into the house I took her jacket (it was early springtime), hung both hers and mine in the closet, then offered her a coffee. Her response to that was, “Make it after we get up in the morning.” Then she kissed me softly but with a fire that she made obvious she wanted me to put out. We made out standing up for probably 8 – 10 minutes before I suggested that we go to the bedroom. She didn’t say anything but took my hand and motioned for me to lead the way.

I had seen Legs’ legs many times at the bar, so I knew that she was fit and well-toned, and that she always had very silky smooth legs. But when I gently laid her down on the bed and started making out with her, and feeling her legs for the first time, I knew this was going to be a night to remember, especially because when I started rubbing her thighs she wrapped her right leg over mine, drew me in closer to her and squeezed me very firmly – not quite like a boa constrictor but I knew I didn’t dare try to pull away (not that I really wanted to anyway.)

We made out while laying next to each other for probably 15 minutes or so, slowly loosening and removing articles of clothing, and getting ever closer to each other’s pleasant parts. Her breasts were just slightly droopy from having 3 kids and nursing each of them, but they were far from sagging and still had a great deal of firmness to them. And her nipples were unbelievable! She always wore a full bra, so nobody at the bar ever had any idea that her nipples were about ¾” in diameter, and protruded more than an inch, and were nearly as hard as a dried bean when aroused. They were amazingly sensitive to boot, and she nearly had an orgasm just from me rubbing and pinching them between my fingers, let alone when I kissed and sucked on them. As I kissed my way down her slender body I didn’t even have to slide my hand between her legs to know that she was already wet, as she actually gave an orgasmic squirt as I got closer to her neatly trimmed triangle.

I was eating her sweet snatch for probably 20 minutes or so, and received several squirts to my face, getting it in an eye once, and catching it and swallowing it many more times as she orgasmed too many times to count. At one point she turned into the 69 position, which was heaven! She was definitely comfortable using her mouth to pleasure me while I kept my face in her crotch for quite a while.

We moved around on the bed until we spooned and I entered her pussy from behind, because she said she liked it better than missionary because “it is still intimate enough to feel like there’s a connection but still have a similar penetration to doggy.”

We fucked bareback for probably 1½ hours before falling asleep face to face after a little more making out and talking.

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 slept until around 10:30 a.m., when we got up and took a shower together. We had some good conversation, including complimenting each other on some great sex, then I made breakfast, we had another fuck on the table right after we got done eating, and I ate her to orgasm again before taking her to her car at the bar.

We hooked up a total of 4 times over the next couple months. We didn’t tell anybody but a bunch of people seriously suspected because there was something different about how we related to each other after that night. Oddly nobody was bold enough to ask me if we had, but she indicated a few weeks later that one of her lady friends said something about us.

We parted friends after the 4 hookups mentioned above because her daughter didn’t like her having me around. She said that her daughter was scared that I might try to take her father’s place.

Of course, we enjoyed several positions but the building of a friendship prior to the hookup lended a considerable amount of intensity to the actual sex. Even though we stopped enjoying sex with each other we remained friends until I moved out of the area a few years later, which always makes things better for all involved.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

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

How intoxicated were you? Not at all (no alcohol or drugs)

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? Nobody

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? The longest female legs I have ever encountered sexually, and all her squirting orgasms, especially the first one before I had even touched her pussy.

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

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? It was really nice to be friends with Legs before hooking up. I think it made the “sparks” more intense, especially on our first hookup.

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 has been a big part of my life since I was about 14 years old. I have enjoyed CS many thousands of times with several hundred partners, some as one night stands, some FWB or fuck-buddies, and even within committed relationships. CS can be a negative when it is either coerced or to try to improve one’s self image/self respect. If one party is coerced, then that can be considered a form of rape both legally and morally. In order to safely enjoy casual sex one should not expect it to be a cure or a tool to improve one’s self image or social standing, but instead it should be viewed as recreation and relaxation, as it can definitely fulfill both of those needs, but ONLY when all parties are willingly consenting.

I think that CS is practiced by more people than would admit it even in a completely anonymous survey. That being said, there are not as many who enjoy it regularly as many of us would like to imagine.

I would like to see the social stigma erased for both men and women who choose to enjoy casual sex, whether on a rather regular basis or simply as an occasional diversion.

What do you think about the Casual Sex Project? I’m enjoying it. I think it is at once entertaining and enlightening.

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