Cudding Mentor-Student



What’s your gender? Man
How old are you? 56
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? North America
What country and/or city do you live in? N/A
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? N/A
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Cudding Mentor-Student

How long ago did this hookup happen? Approximately 3 Years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than 6 months

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? Let me call her CS. CS is a very charming, sweet and beautiful young woman in her late 20’s when I met her. She’s of Asian descent and single. She is petite, about a little over 5 feet – but has a very well proportioned body – beautiful curves in the right places. Her beauty was simple, shy, and unassuming. She carries herself with a lot of self-confidence, firmness and independence, but does not come across as strong, aggressive and never overbearing. She is always smiling – but I find her half smiles or “almost smiling, but not quite”… her most sexy and alluring look. She was very pleasant and quite fun to be with – specially in groups outside of work. I would say, she looks like a young Polynesian Princes who was cool!

She was bright and young manager for one of the support groups that I handled when I first joined the organization. She was assigned to support me and my group. She had already been with the org for almost a year, when I first joined. Professionally, she was very good, sharp, and thorough. She was open to new learning, but was never afraid to share what she knows. She managed her team very well – and what I would consider a very “high-potential” employee who really could rise up the ranks of corporate leadership.

CS was at least 25 years younger than I, the same age as my daughter, who was also already a professional. I had been married for almost 30 years when we met – and I had never cheated on my wife. At best, our marriage is one which I would consider one-sided coasting along. Let us say, only one of us was still looking for intimacy, the other just wanted to “coast”…. which often makes me suspect that my wife has been or may even be still unfaithful to our marriage. But that’s a different story for a different site! At least, at that point in time, I had my equilibrium and balance. I accepted life as it was and I was happy working with organizations and helping young people meet their potential.

In the process of our work, she supporting my organization – we ended up with quite a very professional mentor-student relationship. She was very curious about my past experiences. I would give her advice on how to lead people and manage teams. Sometimes she would share personal situations – and I would give her personal advise, too. I talked mostly about work, and seldom touched on my family – other than answer some questions she would ask, which she did. It was a very professional arrangement, with an evolving appropriate “mentor-student” personal relationship on the side. It was all clean.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? If I would fast forward a little bit, after the hook-up, CS admitted to me that she quickly developed a “hero-worship crush” when we started together. And this quickly evolved and transformed into a romantic crush… that led to 24-hour bouts of fantasizing and day-dream. It came to a point, she later admitted, that she would masturbate in the evening before sleeping after fantasizing all day, and even do it again – in the morning in anticipation of our meetings.

After about 6-8 months after I joined the company, and about 6 months working with CS we became more comfortable with one another. I had a certain personal fondness for CS, more like a daughter, maybe a niece – who was talented and showed a lot of promise. So, as she became more familiar, sometimes teasing and sending what I considered “harmlessly flirtatious text messages” regularly – which I often times would brush aside, but sometimes occasionally go on for a ride. In one of her text message, she admitted her crush to me – which flattered the mid-50’s aging dinosaur, which I even teased as seeing me as a surrogate father or fun uncle or teenage puppy love. Her text became serious, she relented, that she believes it is a real crush and that she believes she is falling. So, I got worried, though still flattered. Through that weekend, the text messages continued… and the exchange somehow got more and more flirtatious…. later becoming mischievous… to naughty…. to sexy…. really sexy. I have to admit that I participated in the exchange, but at a point one- it made me very uncomfortable. One Saturday early morning, I finally text, “Let us stop this crazy text exchange. Let us not complicate our lives.”…. Then, our communication lines went silent throughout the day that Saturday. Worried I may have upset her, I sent her a text asking if everything is okay. She answered by saying – “Please do not text. I am getting drunk.” And then she would not answer again.

Sunday morning, I dropped off my wife at the airport – for a one week business trip. As I drove back, I thought I would meet with CS – just to redefine our working relationship and get things out in the open. Our working tandem had been working so well, I could not afford to let this “juvenile puppy love exchange” affect our work. So, I text her – and asked – if we could meet at DQC, a place just outside of the city, quaint, with many small restaurants and a large parking lot. It was located between maybe midpoint between our residence – closer to mine. It was about 4 pm in the afternoon when I arrived at DQC and I parked my car – listening to the radio. Then soon after her car arrived parking right beside mine. I got out of my car and knocked on her passenger window, She slowly opened the window and I saw she had been crying. I opened her car door and sat in the passenger side. The motor was running, the radio was playing but in a low volume, her air conditioner on. We talked about her “getting drunk” and why. Our chat would go from serious to playful… from sad, to happy. Personal to work… but seeming to go nowhere. It was getting dark and we were still chatting. It was about 6pm. Then we had a moment of silence… looking at one another. She gave me the closed lip, half smile… then looked down. I took her chin and looked at her… and for some reason, I kissed her. You could see that she was surprised by the kiss, but she quickly embraced me and pulled me in. And we had a long passionate kiss in her car.

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? That Sunday evening in the car, we quickly found ourselves in the backseat – kissing. And I would have to say – I have never ever been kissed nor have I ever kissed the way we kissed that night. It was the most awesome, most passionate, hottest kiss I ever experienced then. After an hour of kissing, we were both half naked – kissing and fondling each other everywhere. I massaged her pussy from over her panties, she was so wet, her wetness dribbled across both her inner thighs to her ankles. By simply massaging her, while french kissing one another, I gave her her first two orgasms for the night. She was moaning load – which I found so sexy. I then took off her panties and fingered her while kissing her breasts and all over her – with my right middle finger giving her her third orgasm. I never stopped kissing her breasts and her body – giving her one hickey after another all around. After more foreplay and never taking away my finger, I slid in my forefinger – to have two fingers in her pussy and her pussy cuddled those fingers and she had her fourth and fifth orgasm. We were drenching wet from both her wetness and sweat by then. After recovering from five straight Orgasms, she pulled me up and quickly unbuckled my belt, unzipped my pants, I was naked in 10 seconds. She kneeled between my thighs and gave me the best head I ever had. She licked my penis all over, my balls, my inner thighs, – she licked, she sucked, she played with her lips, with her tongue… she blew on it… all around. I would not describe what she did as “skills or techniques”…. it felt like she was really adoring and loving my penis… and I was absolutely putty in her hands… at her mercy. She would look at me as she kissed me as if she was controlling me and my whole body- my entire emotions… by the joy stick she was playing with. She was awesome. I would have to say – that night -then – I had the best blowjob… in my life. For some reason, in spite being blown I way – I had the stamina to stay and enjoy her loving blowjob and when I blew… I loaded her with weeks celibacy… and it seemed my coming would never end – and she swallowed and she moaned as she swallowed like she, too, was coming as I came.

We cuddled for another 20 minutes exhausted, but continuing to kiss and fondle. When we looked at our watch, it was 11:30pm. We had been inside the car for over 6 hours – making out! We had work the next day.

We parted ways that night to go home – and, except for our knowing glances and smiles, we continued work like nothing happened…. and returned to DQC after work, and the day after that…. etc….

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 continued for a whole year – being an “US”… for weeks to months at a time, then trying to “break-up” for 1 to 2 weeks, then getting back together…. often times have the most awesome and most intimate sexual encounters after the break-up. I hope she does not read this – but I experienced during that one year – the best sex… in every aspect I have ever experienced. She was awesome! We have now been separated for over a year now, going on two.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Fertility awareness (days counting, temperature)

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Just happened, I don’t know why, just went along with it

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? 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? I don’t know / I’m not sure

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? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? The need to part ways, but not wanting to let go.

What was the BEST thing about this hookup? Meeting someone… who I sometimes wished I met in another time, place and universe.

What was the WORST thing about this hookup? Parting.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes.

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

All things considered, how NEGATIVE was this experience? Very negative

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 am still very confused with my situation. In general, I do not believe sex should be “casual”…

What do you think about the Casual Sex Project? Very interesting. Still on the fence…but curious.

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