Cuddling Friends



What’s your gender? Man
How old are you? Mid 50’s
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

Cuddling Friends

How long ago did this hookup happen? Over two years ago…

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

How would you best classify this hookup? Super SPecial FWB… and more!

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

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? CS is a young and bright lady in her late 20’s. She is of Asian decent. Petite, pretty, very well proportioned body – with beautiful curves in the right places in the right proportions. She has beautiful and contagious smile She comes across as sweet and of simple beauty – but oozes with certain mysterious sex appeal. She comes across like a Polynesian Princess… sweet and beautiful, but looking very firm and independent; unassuming and simple, but warm and disarmingly sexy. She’s very smart and intelligent. Self-confident. Professional. She was single.

I, on the other hand, am at least 25 years older, married with a son her age. I had been married for 25 years, pretty much in a lukewarm state – the background of which is a whole different story. In spite of this, I have always been faithful and been a good husband and father to my son. I met her in the office, I had joined in. She had joined the company 6-8 months earlier. I was an executive, she was “upcoming” senior manager working for a support group. She would be assigned to support my organization.

I actually thought that CS was a perfect person to train and mentor for bigger and better things in the organization. She was a quick learner and very professional. She took constructive criticism well and heeded advise after processing herself. She considered me – as her mentor, while I took her under my wing to develop. I admired her ambition, but also found her unassuming and humble disposition quite impressive.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I did not realize that the “mentor-student” relationship, to her, was developing into a deep crush. A crush so deep, I later found out that she had been fantasizing about me, someone old enough to be her father. She later confessed to having masturbated fantasizing about “us”… every night.

How did the hook-up happen? It all started with a series of mostly work related but harmless text messages one Friday evening after a Board Meeting. Work matters, became “mutual admiration” messages, which quickly evolving into flirtatious messages, subtle sexual suggestions…. There were also messages suggesting to get together that evening or during the weekend – initially with a work context, then later with a “let off steam and stress of work” context. I was surprised that I would sometimes try to end the exchange, in the spirit of mischievous fun – by sending an unintended “shock” text… which CS only took it to the next level – almost always with relationship and sexual innuendoes.

How simple text messages between a aging mid-50’s man and a beautiful late 20’s lady – would lead to an agreement to meet in a well known make out place that Sunday evening is just ridiculously bizarre. We parked our cars beside oe another. And as nightfall came – the parking lot became the ideal place for make-out sessions. It was dark and very difficult to distinguish whether any of the cars hand anyone in it.

I transferred to her car and we initially sat together with the air conditioner on listening to music. And at one point, she looked at me – very intently into my eyes, with her lips half parted. I looked at her and we stared for a few moments before I placed her chin on my hand – and brought her closer to me for a kiss!

I am a mid-50’s person who, though I did not sleep around, had kissed a few girls – and had been married 25 years… but her KISS – that particular KISS (and she does not know this is how I felt about that kiss – and all the kisses that evening) – is the most memorable, most warm, most sexy, most awesome kiss I have ever had! Ever!

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 were in the parking lot before 5pm. We started kissing and caressing with our clothes on before 6pm, and in 5 minutes we were in the back seat both half naked.

How wonderful were our kisses – it seems liked we kissed and hugged and caressed one another forever – but only felt like a fleeting moment… we kept begging for more. I sometimes felt – we could have just kissed and kissed for 24 hours – without getting naked let alone having sex – and the night would have still been awesome!

We kissed, we tongued, we sucked we lick. I then removed her bra and opened her dress – and fondled, kissed, sucked and just adored her beautiful beautiful breasts…. I loved kissing and playing with her breasts. They were firm, soft, and just beautiful! her nipples were just right – and they were so soft to suck, I just loved them! in the beginning – I did most of the fondling. I played with her cuddling pussy over her panties – massaging her pussy – which was so wet her wetness were dripping on her inner thigh. I gave her one orgasm just massaging her pussy over her panties. I then removed her panties (which was so wet, you could hear it flop on the floor at the weight of her juices!) and fingered her – while I kissed her breasts… and not before long – as I kissed her breasts while finger her – she gets another orgasm. We rest a little bit while we continue kissing her on her lips – while keeping my middle finger stationary…. then as our kisses get hotter – I slowly slid my fore finger to join my middle finger – and started caressing her pussy with both my fingers… doing all kinds of motions – “walking motion” up and down motion, twisting motion – and CS’s moan just increases and increases… and as I increase the intensity of my finger movements – I shift my kisses from her lips to her nipples and breasts – and start to bite her…. and she orgasms a third time! I slowly remove my two fingers – while continuing to give her face soft kisses all over… then I continue my soft kisses from her face, going down to her chin, her neck, her breasts, her tummy, her naval…. as I make love to her naval with my tongue and lips – I stick out my tongue – and slowly slide it down… to her pubic region – and I play with her pubic hair with my tongue… before I finally kiss her pussy… cuddled her pussy with my mouth… and kissed, licked and sucked it in every way possible… every part – her labia, her clitoris, her vagina… sticking my tongue in her moving it out – I could have stayed down in her pussy for the next 6 months and I would not even go up for air! I loved the smell of her pussy, I loved the taste of her pussy, I loved the feel of her pussy… I moved my face around her pussy as if diving in… and before I knew it – she had one orgasm after another…. by the time she had her 3rd cunnulingus orgasm, her sixth for the night – she pushed my head away. Pulled me up to sit on the backseat.

As she sat beside me, she unbuckled my belt… and unzipped my zipper – while saying, “I have had 6 – and I have not even touched this frat-guy over here!” as she stroked by penis while she gently and LOVINGLY pulled it out. She pulled my boxers along with my jeans completely down my ankles and made me take the off completely. She then quickly slid between legs and said, “It is my turn!” She gently fondled and played with my slowly hardenling penis as she looked at it – at every angle… slowly, gently, and going closer to smell… while gently massaging and feeling my organ. And when it became rock hard – she slowly put it in her mouth and played with it. All I can say, she was very very good at giving head…. and when she gave me head – I would not use the word “skill or technique” tht drove me crazy – it was the way she handled and looked and touched me… it was like she had fallen in love with my penis… it was just mind boggling awesome! She gave me the best head,,, the best blowjob… the most wonderful blowjob – I ever ever ever had till then! She would tease me… to the point of my blowing – and then stop and start all over again… and when I came…. she put my entire penis and deep throated me and swallowed every drop…. and even when I had shot my entire load – she would keep my penis in her mouth and slowly bring it out while sucking every single drop she could in the most gentle and loving way.

By the time I had my orgasm, we cuddle in the backseat…. looked at our watches – and realized it was already half past 11pm. We had been making out for 5 1/2 hours straight – she had 6 orgasms and I had 1. How awesome was that! We even had not had dinner…. and when we reminded ourselves about dinner – we both laughed!

I got out of her car, gave her one last long kiss… and as we kissed – we knew – that had it not been that late into the night – and the risk we were in being in public parking spot just before midnight… IF IT WERE NOT THAT LATE – we would have gone back and probably fucked our brains out for another 5 hours! But we reluctantly parted ways…. and still texting one another even as we drove.

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? Although both of us know that we could not continue indefinitely as many others will get hurt – and it may cause too much of a scandal at work, we just could not get over that Sunday evening.

Suffice to stay – we continued with our hook-ups… many times in that same parking lot… and after a few weeks, we ended up going to hotels and motels – initially for half a day… later there would be occasions of overnight encounters… all under the cover of work. We would have “US”…. for months at a time, then break-up for 2-3 weeks… then get together again. Every time we were “US”…. we would have wild, awesome, romantic, mind-boggling sex almost every other day. It is most intense after break-ups! This continued for a year! In one year, I believe I have had the most sex and the most orgasms… than my entire past 50-odd some years! Crazy!

How do I feel about CS? A real and best friend. Awesome partner. A good person!

After a year, we parted ways out of respect for one another’s status. The parting was difficult…. very… for both of us. We have since – left the organization we were both employed… but separate times. I left first. After almost a year – she, too, left the organization.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

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

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? I don’t know / I’m not sure

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? 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? Very

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

Do you regret this hookup? Somewhat

Why do you regret this hookup? Because from the beginning – even for CS or myself – we both knew that what we had to end and could not continue indefinitely. We both accepted this fact.

What was the BEST thing about this hookup? Friendship

What was the WORST thing about this hookup? Goodbye, ending it. We both knew what we were doing is wrong.

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

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

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

Anything else you want to add about this hookup? I hope she reads this…. I doubt…

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