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? Flint
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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? 1

Tall, Dark, & Lovely

How long ago did this hookup happen? early summer 2004

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 less than a month

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? She was rather tall at 5’11.5″, which was just a little more than an inch shorter than me. She was a 39 year old beautiful medium-dark black woman, with a classic “international” beauty, and had some of the longest legs I’ve known; slim, well-built with heavy C-cup breasts that were still firm and had a healthy, firm appearance. She told me they were all natural, which really surprised me, especially after her having 4 kids. Her hair was a little past her shoulders and just a bit wavy.

When I first saw her from across the office I thought she was very nicely put together – she was well dressed without being showy; just a little bit of makeup to highlight her naturally beautiful and well-chiseled facial features; and had nearly perfect posture yet not at all prideful in bearing – and that was before I saw her from the chest down.

We met at work, initially when she came in for an interview. I was a loan officer in a mortgage office, she was interviewing for the receptionist/secretary position for the entire office, and had been recommended by a friend who worked in the same office with me. When the broker/owner introduced us I naturally looked her up and down to which she quite indignantly said something along the lines of, “Don’t be thinking about my legs like that.” To which I replied with a slightly sheepish smile, “I’m sorry but I really didn’t mean anything by it. It’s just hard not to notice your height. Besides, I wanted to see if you were wearing heels.” She seemed to cautiously accept my reply and made it clear with a look that I was not going to get anywhere with her. Which kind of surprised me because every person in the office looked her up and down in the same way, especially the men, but she didn’t say anything to anyone else, which seemed to almost be a safe way to tell me she just might be open to possibilities, without giving anything away to her potentially new boss. Of course, I imagined what she would look and feel like without clothing.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had been working in the office for a week and a day when I complimented her clothes ~ she had on a pair of nice maroon summer-weight slacks with a light pink sheer top, which was thin enough to show her maroon spaghetti strap tee that matched her slacks. We had talked briefly a few times when she brought files to me at my desk, and once while on the way to the elevator on our way to lunch separately. I am very outgoing and enjoy telling jokes and making people laugh, which proved very easy to accomplish with her. We worked on the 9th floor and were leaving a little earlier than normal for lunch, which meant we would probably have the elevator to ourselves for the ride down. As we waited for the the elevator I told her a brief story about the elevator in the apartment building my brother and I lived in while going to college together. We used to stop the elevator between floors by pulling the doors slightly apart in the middle. She didn’t believe me, so when we got into the elevator I pushed the button for the 1st floor, waited until we got just below the 8th floor and pulled the doors apart a little until the elevator stopped. She almost fell because she wasn’t expecting the sudden stop. She laughed and said with a chuckle, “I guess you were telling me the truth. (pregnant pause as I let the doors close and the elevator continue downward) You know, that could put ideas into someone’s head.” To which I replied with a smirk and giggle, “I’m glad the alarm didn’t sound off.” We rode the rest of the way down in contemplative silence.

About an hour after lunch she brought a stack of files to me, sat down at my desk and started asking me questions about myself. I answered a few and then, as I picked up the phone, told her that she would have to come back later and answer some questions for me. She agreed.

I was somewhat surprised the next day when she told me she was married because she didn’t have any rings on her left hand. And when she told me that she had 4 grown children I about fell off my chair and honestly told her she didn’t look like she could have any more than one junior high schooler, if any children. She smiled, got up and said we’d talk more later.

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? Our first time together was in the file storage room. We were working on putting several boxes of files into the archives, chatting and flirting a bit when she said that her friend had suggested that we get alone together for a while and see what could happen. At that point we sat down and started talking a bit more directly, telling what we liked about each other. Then she said that we could probably have a little bit of fun while there because there were only two keys – the one she had and the owner’s, and the boss was gone for the day. So I leaned forward, looked her in the eyes and told her to kiss me. She leaned in and we started kissing, slowly and cautiously at first, then opening our mouths and letting our tongues start to dance. She was a very good kisser with a nice, long tongue with which she could easily reach the back of my mouth while I did the same in her mouth as our tongues explored each others mouth. We kissed for probably 5 minutes or so when the alarm on my watch went off, telling me that I had a meeting with a client in 10 minutes, so I had to get back to the office. She said I wasn’t getting out of there until she had me in her mouth, and grabbed my belt with one hand while she unzipped my fly with the other. My thought was, “Well, who am I to refuse a beautiful lady who wants to suck my cock?” She took my already hardening cock out of my boxers and greedily started sucking on it like it was filled with water and she’d spent the last 3 days in the desert without any. I normally last for at least 20 minutes for a blowjob but I was shooting down her throat within 2 minutes! I couldn’t believe it! I don’t recall ever cumming that quickly. EVER! Not even to this day.

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? We agreed that we were going to have to finish this up another time, which we did, several times. She surprised me when she came up to the office one evening when I was manning the late phones alone, so I ate her pussy while she sat on my desk (she had a very sweet pussy that didn’t quite squirt but simply gushed when eaten, especially when she had an orgasm, and the more orgasms she had the heavier she gushed). She gave me several blowjobs in the elevator over the next few weeks, and one in the men’s bathroom down the hall from our office, and we were not in the stall (that one almost got us caught). I went over to her house one evening after work and we fucked like there was no tomorrow. That’s when she told me that I was the first man she had ever let eat her pussy, and the first to fuck her in the ass, and she said she wishes she had done both of those many years ago. We set it up one afternoon to have anal sex in the elevator during business hours, which was fantastic. We even fucked between cars in the parking lot on lunch break once, and on the boss’s desk after hours (The boss wondered what in the world caused that odd stain on her desk blotter. We just shot a smile across the office to each other because of the secret that only we were privy to.)

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, Making new friends, Exciting risks.

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? Nobody. (I normally don’t discuss my sexual escapades with anybody because I have seen the damage/embarrassment that can cause if my partner were to hear that I had when she didn’t want anybody else to know.)

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 “chess game” style flirtations seemed to be natural and flowing, with some sort of mental/psychological dance moves on both our parts before realizing that we would wind up enjoying each other’s bodies. And that first blowjob! WOW! To this day it was the best time this man’s cock has ever had in a woman’s mouth! And even with the boss gone for the day, there was some risk to our first hookup, even with it being in the locked file room. And the fact that I knew she was going to tell her friend, with whom I had been working for quite a while, all about our first hookup that she helped setup. The look she gave me when I came back into the office was priceless! She already knew what we did by the look on my face.

What was the WORST thing about this hookup? I had to leave the firm only about a month and a half after we started hooking up. She came up to my place for a visit once the following week but we didn’t hookup, which we both said on a later phone call that we regretted not doing again when we had the chance. After that we fell out of touch. It would have been nice to keep it going for a few more months, but life is life – enjoy and then move on.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, except that I don’t think I would risk a lady’s job again just to have sex. As for my job, I always have work to do and can adapt very quickly.

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? Of my many casual sex experiences, this one definitely ranks in the top 5 when considering that first blowjob and the many subsequent uninhibited hookups with this beautiful lady, especially since I was fortunate to be the first person to ever get to eat her pussy or finger or fuck her anally.

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 truly enjoy casual sex. There is something to be said for the intimacy of sex within a committed relationship, but the risks and mysteries involved in casual sex experiences are and forever will be extremely exciting, even intoxicating in a sense. I have enjoyed sex with more than 350 women since I was very young; and there was one 11 month period (1981-82) in which I hooked up with more than 100 women, mostly one-on-one but several FMF threesomes, and a MFM threesome (straight males).

I think casual sex can be positive or negative, depending upon one’s attitude and reasons for indulging. Culturally, I’d like to see the stigmas and condescending attitudes toward those who enjoy it, especially toward women, fade into oblivion. Also, if we simply take care to keep ourselves clean and disease free, then there will be less of a health risk for everybody.

Wouldn’t it be cool if we could be walking down the street, meet someone with whom we have a mutual attraction, and be able to have sex right there on the sidewalk or in the local cafe or restaurant, or maybe just have public “hookup booths” where we didn’t have to hide unless we wanted to pull the shades.

What do you think about the Casual Sex Project? I am really enjoying CSP. The forum format is liberating, and I feel that I finally have a place that I can share some of my experiences without worrying about who might find out or what someone might think. I’ve had my fair share of Internet hookups, but I am glad that CSP is not a hookup site – at least not yet. LOL.

In my business life I must be careful to not allow my propensity for casual sex to put anyone at risk of being found out by other business associates or partners, especially if she happens to be married. Here I can, as the old saying goes, “Let it all hang out.”

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