Holiday Fun Turned Long Term FWB



What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? East Asian
What continent do you live on? Asia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 0

Holiday Fun Turned Long Term FWB

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Dating casually

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

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

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? While I was on a scuba diving holiday on an island in South East Asia, I met ‘Chica’ on the dive boat, over the long Christmas weekend. She was with a bunch of colleagues from her NGO, while I was with my dive buddy. My buddy and I were pretty much on the prowl, and were very flirtatious. Chica is 5’8″, 28 years old, athletic, and wore her bikini very well. She had a pretty smile, medium short brown hair, and was generally very jovial. I sat next to her on one of the long rides back and we were joking about her Euro accent while she made fun of my US accented attempt at her language. She seemed fun and chill, but you could tell she was into some fun.

We spent the next 2 days diving and drink at the bar. I already met someone before I met Chica and this girl had planned to sneak into my room from her bf, which really demands another story on CSP. I exchanged numbers with Chica, who had to go back to the big city for work, and texted her every day I was on the island. My buddy suggested I invite her to another island where we’d be on for NYE. I sent her the text and told her the diving was good there and she should go. She’d never been there before but hadn’t booked anything for NYE. She later told me she started scheming to get another set of friends to go and meet me there.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The day I arrived at the next island, Chica texted that she’d be there for the NYE weekend, for 2 nights. The problem was, my buddy had some local hookers in the night before she arrived and dragged me into his debauchery for a long night of fucking them! The next day, I was dead and still had to dive in high current, then meet Chica and her friends for dinner and drinks. Chica showed up with her friends, including a guy who was very obviously interested in her. He never took his eyes off her as she talked to me or my buddy. I asked her and she said he’d been after her for months, but she wasn’t interested. After dinner, we decided to walk the strip and find a club to go dancing. On the dance floor, Chica started grinding on me, and I was on my last legs of energy, but still dirty danced and eventually we kissed on the dance floor.

Her group wanted to leave, so I bide her goodnight, thinking I’d get some rest and see her tomorrow. No sooner had I walked into my room, did my phone buzz. Chica texted asking if she should come over. I was almost zombie-like and so I asked her, “what for?” to play coy. She sent a smiley face and “what else?” So I broke down and said sure come over. 20 minutes later, she showed up at my door, escorted by security since it was 4am. I answered the door in my bathrobe. She came in and smiled and said I was eager and I told her I was taking a bath. Her face broke out in a big smile and asked if she could join me. Apparently, NGO work doesn’t allow her to have accommodations with bathtubs, no less ones with a view of the ocean. I told her to help herself and she just jumped out of her clothes, she wasn’t wearing underwear and soaked up the bath. I poured her a drink and joined her in the tub.

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 kissed as I was playing with her feet and legs. Chica hadn’t waxed herself, but she did keep her pubes well trimmed. It was refreshingly natural to see lots of pubes. Her breasts were a firm mid C, with perky brown nipples. I really liked her athletic long legs and was stroking and touching them a lot. As great as that was, I was fading fast, so I suggested we move to the bed. I was too dead to give her head, so I fingered her until she got so aroused, she asked me to fuck her. It was then I’d realized that I hadn’t been all that hard the whole time because I was exhausted. Even with a semi in a condom, I endeavored to fuck her, but my dick, like me, was on fumes and not cooperating. I apologized and told her I was too dead to fuck and I could just finger her till orgasm. We made out and I fingered her while she came once and then I passed out exhausted! It was embarrassing for a first time but I’d stretched myself too thin. She did stay the night and I woke up to the smell of coffee and a naked woman in the bathtub! After 6 hrs of sleep, I was ready to finish what I was supposed to do last night. I showered, drank my coffee and brushed my teeth, then pulled her up from the bathtub like a man on a mission. She said she hadn’t brushed her teeth, but I didn’t care as I kissed her and caressed her with vigor. I nibbled on her pert nipples and she gasped as she reached down to see if my dick was reacting properly, and thankfully, it was!

I carried her, threw her on the bed, and gave her head as I grabbed the condom from nightstand with one hand and pinched her nipple with the other. She ground her pussy to my mouth and I quickly worked on getting the condom on without stopping cunnilingus. Once I rolled the magnum on, I said “this is to make up for last night,” and she laughed as I entered her. Her body shuddered as I slowly slid in and out of her while kissing her mouth, neck and breasts. She wrapped her legs around my waist as I fucked her, tightening her grip as she grew closer to orgasm! Seeing her arching her back, I fucked her harder, and the sweat from the fucking started pouring out from my head onto her belly. She began to moan and jerk from her orgasmic charge, and she squeezed her legs hard to keep me from fucking her as she came, but I held her arms down and positioned myself and kept fucking her! She was riding the orgasmic wave, as the tantricians would say. I was close to cumming so I just kept going. She was obviously very sensitive, so I grabbed her breasts and she moaned more as she tried to pull my hands off her sensitive nipples. I then burst my load and dove down to kiss her nipples which made her retract in post multiple orgasm catatonic shock.

I kissed her on the lips and had to pry her legs off me as she was frozen. It took her a good 15 minutes to recover in bed, while I just ordered room service and walked around naked, checking on her periodically. After food, we sat in the tub again and made out. My buddy texted and we headed out to take some sights. She had to go to meet her friends. She came back that night and we fucked again and again. She had an early morning boat to catch so we couldn’t do an all nighter.
Later at home, she texted that her friends teased that she looked “well fucked!”

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? Once she left the island, we maintained contact and met each other in various cities and continents, as her NGO work moved around. For me, I liked her quite a bit, but never really had deep feelings for her. I told her I wasn’t into anything serious. Chica told me she liked me a lot. She would drunk call me a lot, even while dating other guys. Over the last few years, even though we were both dating and fucking other people, we met up for holidays and such, for fun. I’m the only guy to fuck her ass, and she took it like a champ as I’m not small.

It was only when the guy she was dating got very serious about her did she call me up to tell me not to go see her, as she couldn’t bear to cheat on him. She loved the sex with me, my company and how I made her feel, but he was willing to make a commitment to marry etc. I told her I understood and cancelled my trip. 3 months before her wedding, she called me in a frantic state, asking if we would work and how she felt for me. I was touched and shocked, but I wasn’t about to make that step in my life.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Making new friends, Just happened, I don’t know why, just went along with it, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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? 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? My buddy knew I was seeing her a lot. Then again I was seeing other women too. He knew where I was at and never really gave me a hard time.

How would you best summarize people’s reactions about this hookup? Relatively positive

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

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I met a great girl, who was sexually confident and knew what she wanted, which isn’t common. The fact we got along very well helped the tremendous sexual compatibility, where she liked that I like to take control the majority of the time, to give her pleasure. Even after a disastrous first time.

What was the WORST thing about this hookup? I’d made and lost a friend I’d gotten to like a lot and shared great times with. I suppose everyone has to progress in their own direction.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all. I know that I can connect with women on many levels, without lying or cheating with clear communication.

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

All things considered, how NEGATIVE was this experience? A little 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? Rarely have I had ONS and hookups without talking to a woman and turning on her mind first. I’m fairly good looking and many women would say that, but somehow, I very rarely get that whole animalistic hookups until after chatting, even in Asia! Not sure if it’s racial stereotyping etc, but if OKcupid and Match data show East Asian men as least desirable, while 1 in 5 men are East Asian on the planet, and 2 in 5 are Asian. I date all races, and maybe I have a few types I like more, but I don’t adhere to it strictly, preferring to be open. It would be nice if the world would be a little less closed in that respect.

What do you think about the Casual Sex Project? It’s great! A cathartic release to tell secrets anonymously!

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