My Boss, My Frat Guy



What’s your gender? Woman
How old are you? 29
What’s your race/ethnicity? Southeast Asian
What continent do you live on? Asia
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
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

My Boss, My Frat Guy

How long ago did this hookup happen? About a Year Ago

What was your relationship status at the time? In a relationship (monogamous)

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

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? I was working in a local company for at least a year when they hired a new executive to head the manufacturing stream. He was at least 20 years older than me, very experienced – and in fact one of the known manufacturing leaders in the industry. He is, I would say, how normal executives look like – very formal, with his hair neatly brushed up and beard well shaped. Our first meeting was somewhat normal. I had to orient him with the company’s financial situation, which lasted about thirty minutes. We did not have any face-to-face meetings until I was eventually assigned to serve his department directly. The meetings were usually with the entire management committee. The other members of the management (which are my friends, too) always talk about how handsome he is – how tantalizing his eyes are, how kissable and pink his lips are. I never really noticed ‘til that one Tuesday meeting, when for the very first time – I saw him in his “rugged” look, he was in a collared blue shirt, hair not brushed up, and his smile was just…

Since that time, I knew I already had a big crush on him. I would take any chance just to have a chat with him, although usually related to work. At night, or as I wake up in the morning, I would start fantasizing how it would feel like kissing him, fucking him – I would “M” at least 2x a day, once before I go to sleep and one in the morning, either because of anticipation of my one-on-one meetings with him, or at night after a long, tiring workshop with him. He would text and consult every now and then, which makes me more and more excited and aroused. The texting and one on one meetings lasted for at least three months until I felt that I was feeling something beyond the fantasy – not only did his looks caught me – I also truly admired him because of his wit, his gentlemanly gestures, his character, and his stories. This time, I felt scared – I think I was in love.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? One Friday evening, he invited my team through me for an after work-dinner, but (un)fortunately my team are all not free. I told him it was only me who was available, and he said, okay, then maybe the two of us can have dinner instead. My heart was beating fast, I immediately re-touched, put my lipstick on, went straight to the car and drove as fast as I can to reach the meeting place, but about a kilometer before I reached the dinner place, he suddenly cancelled and gave a lame excuse – “I have to buy soft drinks for home.” I was disappointed then but did not show him. The next day, we started exchanging erotic conversations – telling how we want to kiss and fuck each other, I thought it was going to progress further until he said: “Let us not complicate each others’ lives.” I felt so down. I thought (no matter how wrong it was), I would finally be able to live my fantasies, I thought I would be able to finally kiss him and make love to him. After that message, I did not reply – went straight to a friend’s house and got drunk – I didn’t even know how I actually managed to reach home.

The next day, I received a message from him asking if we can meet – maybe this is just to clear things out, to make sure that we will not be awkward knowing that he’s my boss, and I would have to work with him every day. For me, maybe it is to say goodbye to him, to the feelings, and to the fantasies. And so I thought..

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 met at around 4 pm in DQC, a few kilometres from our homes, with several restaurants and a huge parking lot. He came a few minutes earlier than me. I picked him up at the front of one of the restaurants, and he accompanied me to the parking lot. Both of us were not talking. As soon as I parked the car, he looked at me and said, “You’re beautiful” and kissed me on the lips. IT WAS A DREAM COME TRUE! I did not hold back at all – I held his cheek and kissed him back! We were kissing for at least five minutes, not caring that my car was not very tinted and that people were passing by the parking lot.

We transferred to his car – and at that time, we did not stop kissing. He started kissing me on the neck, slowly caressing my breasts. I felt his hand unhooking my bra and he slowly lifted my blouse exposing my breasts. His look felt like he was memorizing each and every part of it – his thumb circling around my nipples. I felt my pussy starting to get wetter, and more excited! He slowly sucked and licked my breast, and his other hand caressing my pussy from over my underwear. Watching him, feeling his lips and his hands and his body all over me – I had one big orgasm! I thought it was it, when he removed my underwear, lifted my legs and my butt, and exposed my vagina! He started kissing and sucking my clitoris, and slowly inserted his finger inside me. The pressure was slow but passionate, and I can feel my fluids dripping both because of pleasure and of the excitement that finally, my fantasies with Fratguy came to life, and it was sexier and more exciting knowing that someone might actually see us! I had at least 3 big, crazy orgasms in the car – one after the other!

I didn’t let that day without giving him one – opening his zipper was like opening a gift – the clinking of the belt gave me so much excitement! His penis was one of the most beautiful ones I have ever seen – it smelled so sweet, and tasted sooo sweet too! I immediately dove into him, alternately sucked and kissed his penis, and his balls.. his moaning was music to my ears.. and as he nears his climax – he pushed HIS deeper into my mouth, and I swallowed one huge orgasm! I grinned and he gave me a peck on the lips. That night was 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? It’s about fourteen months after our first adventure, and we will continue to meet and hook up, even after we both resigned from the company. He would pick me up from the office and we would check in into different hotels and motels around the area. I’d say really have extremely exciting sexcapades, in the office, at a friend’s house, in hotels during conventions and business trips! I’ve had at least a 500 orgasms to date, and counting!

We’ve had several breakups from the last year, some longer versus the other. And we would really try our best not to see or speak to each other – but here we are, still together. At this point, I don’t know how and when it will end, at least I am hoping not in the near future. The complicated part is that – I’ve fallen madly in love with him, knowing very well that what we have is a “friends with benefits, fuck buddy” agreement. I know very well from the start that “love” is not in his equation. As crazy as it sounds, I would sometimes trend, knowing that he’s also making love with his wife. Let’s keep it at that.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Fertility awareness (days counting, temperature)

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? 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? My best friend. She was very surprised knowing that it was actually my real first time, and it was with a married man 20 years older than I was, and my boss. I would want to make her believe that it was only for fun – but knowing me very well, she knew it was something deeper, it was slowly transforming into real love, at least for me.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Feeling wanted, and falling in love.

What was the WORST thing about this hookup? Having to part before midnight because he has to go home to his wife. Knowing that eventually, it would have to end. Knowing also that the feeling of “love” may be one-sided. I don’t know. I am not sure.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don’t think so. Because at least for me, I knew from the start that the “casual” sex happened because of something deeper. As for me, I have learned to somehow deal with depression, with parting… But not sure if I can deal with it again.

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? I think it is very important to clear things out with your partner — and not get attached, maybe a piece of advice for someone who has fallen in love. You have to be on the same page — know exactly when to stop, and what to feel. Once the hookup is clouded with feelings, then it becomes complicated.

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 I think is something people do to make them feel better about themselves. However, this is still not advisable — especially if you get attached easily.

What do you think about the Casual Sex Project? Very good place to share what you feel without being known.

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