Falling in Love with my FWB



What’s your gender? Man
How old are you? Less than 60 years old….
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? 1

Falling in Love with my FWB

How long ago did this hookup happen? Less than a year ago

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

How would you best classify this hookup? Started as FWB… with an agreement of ending within a fixed time. Both sides fell in love… and struggled letting go.

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? Let us call her FanGirl. She is a petite, dark haired, and very charming girl. She has very beautiful – “right-size” and firm breasts and a sexy figure. She is single. At that time, she had a boyfriend, who she was seriously and exclusively going out with. FanGirl is about 30 years younger than me, and is a colleague at work. I, on the other hand, on the surface am a happily married middle aged man, married for over 30 years, whose 3 children are already all grown up and on their own.

We started working together over two years ago, and because of work conditions, we developed initially a close friendship. At some point, she admitted to me accompanied by non-stop flirting that she was my “fangirl.” Then one weekend, during an unintended impromptu meeting one afternoon to discuss work, surprised ourselves – one moment as professionals – ended up making out in a car for over 6 hours inside the car – never reaching the agreed upon cafe where we were supposed to meet. We had quickly transformed our relationship from colleagues into a very hot, steamy, sexual… FWB relationship. REALLY HOT! The single encounter was so intense, that we both got scared (by the implications at work and our personal lives) that we both agreed to end the relationship…. after a week. Which meant – we continued our en-car-ters…for another 4 days – which meant whenever we can – sometimes my car, sometimes her… in every possible and conceivable opportunity – for the next 4 consecutive days to hot steamy petting and making out. And to withhold actual REAL-DEAL-SEX for the finale – when we “end” the FWB relationship by checking into a hotel, overnight. I had to make an excuse at home to do this. We were in the hotel for 36 hours – during which I had 5 orgasms and she had 18 BIG O’s…. we perhaps each slept a total of 4 hours during the 36 hour period. We returned to work still “Sex-Lagged” not knowing what “hit us” that weekend.

After that weekend, tryst, as agreed upon – we broke up. And for a week after – then, but upon realizing that the sex was just too awesome – decided to get extend the FWB relationship (still with the intent to end) and got back together again. And so we continued… but this time checking into hotels and motels – after work, weekends, extended lunch hours…. whenever, and wherever, we would be at it! We did this, while still maintaining and going through the motions of normalcy with our respective partners. We openly talked about our “other lives”… in between and during non-sex-sessions and during non-work time. But those times are very far and few in between, because if we were not working… the chances are – we were having sex somewhere… and going to our respective homes to sleep and eat.

But, somehow, we agreed, we felt, we knew… we had to end it. We did, we agreed for good. Not long after ending – I left the company about a year ago to set-up my own business. FanGirl resigned 2 months after I did – and we tried our best not to get in touch with one another.

Or so we thought.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Then, about 6 months ago, about a month after she left the company – I contacted her – in the guise of turning over some files and books that she had left with me. It was a funny phone call, because we had not talked to one another for over 3 months – let alone seen one another – and yet, during the phone conversation – let us say, that by that time ended the call – we had already planned to book a hotel close to her work (since I was starting my own business – my time was more flexible) – where I would rendezvous to meet with her after work – and we would have another 18 hours together.

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 Rendezvous we did! I was in the hotel room by 4pm, and she quickly arrived after her work – at about 6pm. I know we ate dinner and breakfast during that 18 hour period, but frankly – I cannot remember what and how it was we ate. All I know – is that as soon as she arrived in the room – we were at each other’s arms – giving one another long passionate wet kisses and groping one another everywhere and anywhere. What was new this time – and we both know this was “another CHEAT- LAST DAY EXTENSION” to our agreed ending of the FWB relationship. So EVERY SECOND of our encounter that day felt like 100x more intense! What was different – without discussing it – we both felt the urge to video tape as much as we could our encounters. I remember – still fully clothed – I sat on a chair facing the mirror of the masters bedroom of the suite – and had set the iPhone for the video – and she just straddled on my lap and we kissed… and based on the video clip length – we were at it for over 30 minutes – and much longer – kissing and groping – without even undressing – because the video ended when we had accidentally tipped it over! It was HOT!!! We took a video when we went to the bathroom – and we had over 60 minutes…. and could not even count the orgasms… and when we left the video of our bedroom encounter… drives me crazy just thinking about it! She rode me cowgirl, and sat on my face, we did 69, I took her missionary with her legs on my shoulders – and I licked her toes as I fucked her… we rolled around – I gave her head, then she gave me…. it went on and on and on – all night till the morning. In 18 hours – I had 3 orgasms – and she had 9 really – BIG MOANING LIKE CRAZY ORGASMS!

On a number of occasions – even throughout the year or so as FWB, during our “afterglow” period after hours of sex, FanGirl would be tempted to ask me how our sex was compared to my sex with my wife. She would even ask- if and when…. but all these in a very shy and almost teasing way. I never directly answered her in our almost one year of FWB Relationship. However, allow me to do so now – FanGirl gave me the best mind-blowing, most romantic, most intimate, most orgasmic….. gave the BEST Kiss, the BEST Blowjob – I have ever ever experienced. She has, at least for me – BEST looking, tasting, feeling Pussy – for me I experienced the Best SEX… I have ever had… compared to anything and anyone during my single or married life time! Together, we were just awesome!

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? Then, in the morning, almost lunch – just before it was time to check out, she gave me several “goodbye” gifts.. Already dressed in our street clothes – we hugged and cuddled for the last time for another 30 minutes before finally leaving the room. There were a lot of tears, and “I love you.”…. words we were afraid to say, but that morning exchanged generously and continuously as we embraced.

We said our goodbyes.

It has been over 4 months since we last seen each other. We are now both, I guess, leading our own respective lives. And I sometimes wonder….

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, I was feeling lonely, Just happened, I don’t know why, just went along with it, I didn’t want it but was unable to stop 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? Somewhat

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? Somewhat

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I think I fell in love…

What was the WORST thing about this hookup? Falling in love…

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Gave me a lot to think about.

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 know I would very much want to keep the friendship and stay in touch, but there will always be the “risk” or the “opportunity” to continue hooking up… very likely. Let us see what happens.

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 still do not know. Because, though we “choose” to classify the sex we had as “casual”…. I know our sex – at least for me- was definitely anything – BUT NOT casual.

What do you think about the Casual Sex Project? Informative…. a good venue to vent…

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