My Dream Fratguy



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)? 2
How many hookup stories have you here posted before? 0

My Dream Fratguy

How long ago did this hookup happen? More than 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? Fratguy was new in the company I was working for. He’s in his early 50’s, married, and he’s one of the best executives in the industry personally hired by the owner to help fix the mess in the company. My first meeting with him was just professional, and for at least two hours we just spoke about my opinion about the state of the company. After that conversation, there were only very few meetings and interactions — just mostly during meetings, but we never get to really talk. At that time, it was just a boss-colleague relationship, until…

One morning, Fratguy went into our usual cycle meeting with a rather different aura. His hair wasn’t tidied up, and he looks very very casual. That was the time I said, “Boss looks very handsome today!” That’s when I started really stalking him — looked at his achievements on the internet, sometimes steal glances in meetings and in the canteen. It was also when our communication started to become more regular, most of the time would revolve around work, but sometimes we would talk about some of his hobbies. I must admit, every chat, every text messages sent really made me giddy at first — like a nobody in college who was suddenly noticed by the most handsome fraternity head on campus. My giddiness quickly escalated into sexual fantasies. I would end up masturbating at night every time we had a good meeting, or in the morning in anticipation of my daily meetings with him. I, being his sounding board, also had the opportunity to meet him even after work. Though I’d say, the crush turned sexual fantasy quickly escalated into something more — I think I am falling in love with him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were already exchanging personal messages for more than a month, the exchange escalated quickly one Saturday morning. We started “sexting”, telling each other how we wished we were cuddling and feeling each others’ body that morning. I thought at that time, the feelings were mutual. I was already on cloud nine when he suddenly just burst my bubble and said, “let us not complicate each others’ lives.” I felt very angry at myself, I felt that had I known, I should not have let myself into that sexual conversation. I admit I was hurt because I thought it would be the “start of something” for the both of us. I immediately stopped replying, drove my way to a friend’s place and got myself really drunk. I said it’s part of my learning, and that I should have realized from the start that this person will never like me — as a partner, sexually. He kept messaging me that night but I wasn’t responding already – as I told myself it is done (well, it never even started anyway).

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?

The next day, when I was already sober, I received a random message from him, “I want to see you.” In my mind, I knew it was for him just to clear things out, maybe for us to have the venue to apologize to each other and that was it. I agreed and we met in a secluded chain of restaurants with a huge parking lot. For some reason, the turnout of events was not the one I imagined at all. I picked him up and we parked the car in one of the secluded space. I was not talking, so was he. Until he looked at me and said, “You’re beautiful” and gave me a super wet kiss on the lips! That was the best kiss I have ever received in my entire life! His lips were so soft and warm, and his breath was so sexually enticing. In a few minutes, we found ourselves in the backseat of his car, at first exchanging kisses, and then I felt his right hand slowly unhooking my bra. The fact that we were in a public place actually added to my excitement! He removed my bra and slowly lifted my shirt and exposed my breasts.. his eyes were gazing at it, as if trying to memorize each and every curve of my breasts.. he started caressing my nipples, while he kissed me the lips… then on the neck.. and then kissed and sucked my nipples I almost had an O! I was trying not to moan loudly but he was sucking, licking and biting it so well! Then I felt his hand slowly removing my underwear. I was hesitant at first given that it was my first time, but hell, this is my chance to actually make love with my fratguy! He removed my undies as I spread my legs wide, as if giving him permission to touch me down there. He caressed my clit (while still kissing my nipples), and then slid his finger inside me, alternating the pressure from super slow to fast. I immediately had one! But he did not stop, he lifted my lower body, raised my skirt, and kissed my then extremely wet pussy. I can feel his tongue feeling every inch, orifice of my vagina.. He kissed and sucked my clit, then he’d push his tongue inside my vagina. I had at least 4 more that night! He is indeed such a good lover!

With such enthusiasm, I said I will not let that day end without touching him. He was at first hesitant, but I insisted. My excitement went higher as I open his zipper and pull down his boxers. Oh what I beautiful sight! The smell of his penis just made me really crazy! I slowly kissed its tip, and kissed his balls and soon after sucked and ate it completely! His moan made me feel more aroused, more excited as I increased the speed and the pressure — and as he was about to come, he pushed his head deeper into my mouth and I swallowed completely. He gave me peck and said goodbye.

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? The hookup lasted for more than four years, and until now, we still do not know when it will end. Our hookup actually transformed into a “real” relationship, even if we always try to deny it. “I love you’s” were the words we always try to avoid to say, but we say nonetheless.

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 Bestfriend. She was surprised I was actually hooking up, and in fact hooking up with a guy 20 years older than 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? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? Because the hookup turned into love, I now love him very much, even though I know it will eventually end

What was the BEST thing about this hookup? Having a best friend, and a lover in one — plus the best sex!

What was the WORST thing about this hookup? Knowing that I will eventually have to let go of the person I love

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? In a way. Though I still believe ours was not at all just a hook-up. It was a deep connection, longing, and eventually.. love..

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? You cannot always predict who you would be sexually attracted to.

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? The expectations on Casual sex — or sex in general, should be clear on both parties, otherwise, one will definitely get hurt.

What do you think about the Casual Sex Project? Good place to share your experiences without being judged.

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