Race/ethnicity: Asian Australian
Current location: Melbourne, Australia
Highest education received: Post-graduate degree (currently pursuing)
Relationship status: Confused?
Religious affiliation: Christian – Anglican
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0
Scared but Willing
How long ago did this hookup happen? June 2015
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? First of more? Honestly I don’t really know.
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? He is 41, with light brown hair. He was fairly muscular and considerably taller than me (5’9″?). We work for the same company but I worked on his floor briefly and spend about three months in the team before going back to my original position. I liked him, he was friendly but we weren’t too chatty. I honestly think he wrote me off and didn’t really think he was interested in me. I liked him but I realized how unlikely it would be that we would ever get together. There’s a significant age gap and he seemed like he wanted different things than I did. I’m quite traditional and want that sort of ‘white picket fence’ life with marriage and kids but he seemed like more of an eternal bachelor type, where he never really wanted to grow up and was satisfied in the way he was living his life at that age.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? At my last week there, we ended up spending a lot of time together because he were the only two working for a client outside the office. He sent me a goodbye message as I was leaving his team and he asked me out. We went on a first date which went alright but I freaked out afterwards because I felt conflicted, I liked him but didn’t want the same things he wanted so where could it go? The second date we almost had sex but I was scared, it was going to be my first time so I was nervous because he was obviously quite experienced and I didn’t want to disappoint. I wasn’t even sure he wanted to see me a third time but he did, I went to his house so we could meet up before going to lunch but we basically went straight to the bedroom. I knew what was happening and what was going to come next but I tried to relax and convince myself that what was happening was okay.
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 started fooling around, he went down on me and I didn’t really enjoy it and felt awkward so to get it over with I said I wanted him now and that I wanted to feel him inside of me. As he was getting the condom I performed oral (also first time) and he seemed to like it but it was only brief (for maybe a minute) and then we had sex. I felt strange during it, growing up religiously plagued me more than I thought. I felt like I was doing something wrong because I didn’t really know this guy that well and there’s nothing that’s keeping us together. He was good looking enough but I always pictured my first time being with someone I was in love with and he’s not that. He seemed to move quite quickly from missionary to legs over the shoulder to knees to the chest and then he came. I was surprised about how quick that was, because it was probably only five minutes total and he saw that I was bleeding. I didn’t know what to say because I was embarrassed. He didn’t seem to mind and kept going. Afterwards he offered me a towel and told me to take a shower and then we’d go to lunch as planned. Honestly, we didn’t talk much. I was scared and he didn’t do much to make me feel better.
When we came back from lunch, we had sex three more times. He came very quickly each time and I don’t really know what to think about that. He took me from behind, the next time I was on top and the last time he was on top again. I didn’t bleed those times but when he first entered me I didn’t feel ready (I wasn’t really wet).
Did you have an orgasm? Did your partner(s)? He did (presumably), I couldn’t really see much in the condom but he said he did. I didn’t.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom that first time. After lunch we had rounds 2, 3 and 4 and for those we didn’t use any protection but he did know I was on the pill. We didn’t take any STI precautions.
What were your REASONS for having this hookup? I wanted to know what sex felt like, it happened with him because I wanted it to be someone who didn’t really have much crossover in my life so if it went badly we could make a clean break. The other reason is that for some reason I trusted him, I know I shouldn’t have and that didn’t really make sense but I’ve had quite a negative sexual experience before and he seemed like the kind of guy who wouldn’t want to hurt me.
Were alcohol or drugs involved? If so, how much? None for both of us.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I freaked out because he didn’t talk to me for the rest of that day or the majority of the next (I got a message late the next afternoon). Currently we’re still seeing each other although I’m not sure in what context. I feel guilty about it and I know I shouldn’t but there’s this lingering sense that I’m doing something wrong. On a date some time afterwards, he told me that he worries about our age difference because he thinks I don’t want the same things he does. He says that he wants to settle down and have kids and I just seem to be in it for fun/having casual sex. The funny thing was that I was the one who wrote him off as wanting to have fun. I couldn’t tell him that I wanted something different afterwards and I was sad that he wrote me off like that. I feel like it’s going to end soon because of our schedules but honestly I don’t want it to. I’m scared he’s going to leave me.
To whom did you talk about the hookup? How did they react? I told my sister I was seeing him (but not sleeping with him). She’s not really happy about it and the age difference. Because of this reaction I haven’t told her that we’ve slept together and I also haven’t told anyone else.
Was this a consensual and/or wanted experience for you? For your partner? It was consensual for both. I felt confused but I wanted to do it.
Do you regret this hookup? If so, why? Now that we’ve seen each other for a bit, part of me wishes that this never happened. I like him and I’m torn because I feel like he’s written me off. If I hadn’t had sex with him then maybe he wouldn’t feel this way about me. On the other hand, if I hadn’t I’m pretty sure he would have stopped talking to me. I’m disappointed in myself that so much of my self-esteem rests on this. We’re both going away on different vacations soon and we’ll be separated for a month. He says he’ll see me after but I have doubts about that. Where can we really go from here? We’ve got a big age difference, we’re at different stages in our careers and have very little to talk about. I’m worried.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this was that it was my choice. I’ve previously felt that I’ve been goaded into these things, to perform or to act sexually with men but this was what I chose to do and for that reason, I feel like maybe I had a little more control in my life than what has happened previously.
The worst thing is the guilt, the knowledge that this wasn’t what I imagined and that it’s probably not going to last forever. I don’t know if this is for religious reasons or whatever but I still hold on to that ideal that I was supposed to have sex with someone I loved and wanted to spend forever with. That doesn’t necessarily mean that I have to be married first but this is just not what I thought would happen. I know rationally I should be okay with this but I’m not. I can’t even share this with anyone because if I say anything it will change the way my friends see me.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? Somewhat negative
Anything else you want to add about this hookup or anything else? I didn’t realize what this meant before it happened. I know what casual sex is and I don’t judge others for it or think that it cheapens a person but I feel cheap and dirty and used. Not used by him but I feel like I shouldn’t have let this happen. I like him but I should have kept in mind that it was going to end regardless of what I really wanted. If he leaves, I feel like this will ruin me and I don’t know why. I really didn’t want to get caught up like this.
You have a hookup story to share? Submit it here!
What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!