This post is sponsored by Trust Massage Oil.


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? 6

Intense Relaxation

How long ago did this hookup happen? 1989

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 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? Dee, as I’ll call her, was a 22 year old single mother of a four year old son when we met. I hadn’t seen her standing up because the only times I saw her was when she passed through the security gate to visit a friend of hers in the mobile home community where I was working security on weekend evenings, but we would have brief, flirtatious chats if there was nobody else behind her. She had dishwater blonde, longish, full bodied hair; dreamy green, inviting eyes; and perfectly formed full (but not big), soft looking lips; an inviting smile; and smaller, well-placed breasts. Her voice was mid-range in tone and was smooth as a mourning dove’s coo, especially when aroused. She had probably the most relaxed temperament of any woman I’ve known, to the point of being intensely relaxed, even in the face of troubling circumstances. Hence the title of this post.

Being naturally and perpetually horny, I was always on the lookout for new sex partners, and when I saw Dee for the first time I knew I had to get to know her.

After flirting with her several times over the course of a few weeks I told her I wanted to get to know her better, and got her phone number. She said to call when I got off work. I reminded her that I clocked out at 4:00 a.m. but she said that she looked forward to my call and that we could talk then.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After finishing up my reports and opening the gates for the rest of the night, I called her from the guard booth phone (this was before cellphones became the norm) and she quickly invited me to come over for a visit. I could tell from the tone of her voice that she was probably having similar thoughts as I, and wrote down directions (she was not very good at giving directions but that did not deter me one bit. LOL)

When I got to Dee’s place she greeted me at the door wearing yellow sweats with lavender trim. I wondered if she had anything besides her birthday suit beneath her outfit because she looked amazing. Remember, this was the first time I saw her outside of her car, and I was slightly surprised at how tall she was. I had imagined that she would be around 5’3” but in reality she was closer to 5’9” tall, and weighed in at around 135 lbs., which to me was exactly perfect for her face and shoulders now that I saw her upright. She had nearly perfect posture without appearing at all pretentious. She invited me in and asked how I like my coffee. While she got our coffees she asked me a couple of opening questions that required only short answers. I complimented her on her outfit and her home, then asked her some questions about herself. She was warm and inviting yet seemed to have a little bit of guard up but her body language and eyes suggested that she was ready to find a reason to drop her guard if I could help her feel that I was not a threat. This seemed odd to me that she would invite me over at such a late hour while still being guarded in this way, but I wasn’t going to demonstrate anything but safety for her and her son, who woke up, came to the table and climbed onto her lap without saying anything. After he climbed onto her lap he looked at me, then back at her as if to ask, “Who is this strange policeman (I was still in uniform), and what is he doing here so late?” She introduced me and said that I had just stopped by for coffee. He sat up, stuck out his hand and gave me a surprisingly firm handshake for a boy his age, and said, “Hello Mr. M., it is nice to meet you.” Then gave his mom a kiss and told her good night, looked me in the eye and said firmly but not unpleasantly, “I don’t want another daddy; mine is the best. Good night, Mr. M. See you next time.”

Dee did not try to correct him in the slightest, which was very encouraging because a kid needs to know that his mother encourages him to express his feelings without fear of being told how to feel, and he was very respectful in his demeanor. This suggested to me that Dee was a good mother.

Anyway, I digress. After her son went back to bed she and I talked over a couple cups of coffee for probably about an hour or so before she stopped, looked me square in the eye and said, “You look very tired. You should sleep here.” I said that I lived only a few miles away and that I should get going. To which she said, “M., will you please sleep here? I have a king size bed and the sheets are clean and warm. And besides, I’d like you to hold me while you fall asleep.” Well, what’s a man supposed to do with an invitation like that besides ask about her son. She said that she would deal with that later but that she still wanted to fall asleep in my arms.

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? And so we did just that; we went into her bedroom where she promptly began to remove my tie and shirt, then knelt down and undid my belt and zipper, pulled down my pants and underwear at the same time, and took my already stiffening phallus with both of her soft, warm hands and started very softly, almost worshipfully stroking me before commencing to kiss the head of my cock, licking the precum with just the tip of her extended tongue, and finally after a couple of minutes taking the full length of my cock into her mouth before wrapping her lips around the base of my 7½” long and thicker than average cock, and just holding it in her mouth with her eyes closed as if she was enjoying a delicacy that she had been craving for a very long time. She just stayed there on her knees, holding my cock in her mouth without anything but small movements of her tongue for what seemed like at least a minute before starting to slowly bob her head back and forth, using just the perfect amount of suction and tongue work to nearly put me over the edge within about five minutes, stopping just before my point of no return and saying, “I want you inside me before you cum.” We then laid down next to each other, kissing slowly and deeply until she draped her leg over mine, and reached down to pull me into her very hot and firm vagina for the first time. She had a few very nice, relaxed orgasms while we slow fucked in a few different positions starting, as I said, side by side, then onto my back for cowgirl while I fondled her breasts, then I sat up without stopping the intercourse and sucked on them for a while, then into the missionary position before she asked me, “Please cum inside me. I’ve been on the pill for the past 3 years, so I can’t get pregnant. I want to feel you shoot inside me.” I then had one of the most intense orgasms I had ever had at that point, all without ever once fucking hard or fast, and she followed up with another slightly more animated orgasm while I released my load deep inside her body.

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? After cumming deep inside Dee’s pussy, we fell asleep with me on top of and still inside her, holding each other as if this were the last time either one of us would breathe. We slept until her son came into her room to wake her up at about 9:00 a.m. so she could make him their traditional Saturday morning waffles with strawberries, honey and cinnamon. She insisted that I stay for breakfast, to which her son gave his hearty agreement. We talked while I made coffee and she made breakfast, with her son interjecting his thoughts into the conversation on occasion.

(Sidebar) She taught her son to speak very plainly and with good grammar, so much so that I would have thought he was about ten years old rather than four.

Dee and I dated a few times, but mostly she would invite me to spend the night with her nearly every week for more than a year, even after I left the security company. We parted friends after about 17 months, but hooked up on occasion, usually about once every three or four months for the next several years. We had several noteworthy hookups, some of which I will share in later posts. Suffice to say for now, though, that Dee was a classy, relaxed lady with whom I enjoyed a really good fuckbuddy/FWB relationship for several years.

She contacted me a few years ago through FB, and we talked a few times but decided that it was best to simply keep our memories instead of trying to create new ones. Sometimes I miss her.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Making new friends, 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? I didn’t tell anyone about her.

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? There were several things that were remarkable about this hookup with Dee. Probably the best thing about this hookup, however, was the incredibly slow manner in which she took my entire cock into her mouth before even slightly touching it with her lips. I’ve enjoyed a great many fantastic blowjobs but, to this day, I’ve never known another woman who has taken it all the way into her throat without touching it with her lips on the way down. And her supremely velvety pussy was simply divine, and perfect for slow fucking, generating mind-blowing orgasms.

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? Dee’s eyes were absolutely mesmerizing to gaze into while I came inside her.

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, 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 enjoy reading stories of other people, especially women who have written about first experiences of any kind.

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