You Compassion Is a Weakness He Will Not Share



What’s your gender? Woman
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Fitness instructor
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? One other

You compassion is a weakness he will not share

How long ago did this hookup happen? The last hookup was a month ago

What was your relationship status at the time? Same as current status

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

How long did you know the person before this hookup? For less than 6 months

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? B. and I met through mutual friends. About a year ago, his best friend was dating my best friend; our two friends thought B. and I had a lot in common and would get along. We went on a couple dates and I instantly fell for his charm. Even though he was blunt and cocky and kind of an asshole, his physique was exactly what I wanted. Slightly taller than me, darker skin tone, VERY fit/muscular, a ton of tattoos, and a huge, gorgeous smile. He was honest with me upfront that he “dates around” and prefers casual sex to relationships/monogamy. With those first few dates, I thought I could separate the physical from the emotional attachment. I was not too disappointed that he didn’t want a relationship, as I was (and am still) terrified of commitment. Based on the first few encounters, I did not think he would be a good “relationship” fit for me anyway. I felt I needed someone deeper, who respected women more and matched my empathy/compassion for others. BUT I also knew I was very physically attracted to him. I had only had sex with one other guy in my life, but I felt when I interacted with B., and talked to him, my hormones/sex drive skyrocketed. The first date we went on ended in a hot and heavy make out session, and the second ended in oral sex (giving and receiving for both parties). He said he didn’t want to go all the way that night, but I wanted it SO bad. I hoped the next time we hung out we would be able to. However, shortly after, B. met someone he started to catch real feelings for and we were completely platonic for the next couple months- we saw each other maybe once per month, and only texted occasionally- which was torture for me because I still wanted him so badly. Initially I was more physically longing for him than emotionally; however, in the weeks we were platonic, I found that he actually was not a complete jerk and was much more sensitive than he initially led off to be. Things fizzled with the girl he had been talking to, and we started hanging out more again. We talked/texted every day, and hung out every weekend. But we still weren’t sexual. Just when I was getting to the point where I was accepting we weren’t going to be physical anymore, he texted me that he needed to “get some soon.” And he seemed realize simultaneously that it would be a great idea for me to go over to his house to watch a movie. That night ended with only him getting a BJ and us getting through half the movie. The next time we saw each other, we finished the other half of the movie, along with mutual oral. I hoped this meant we would actually get to have sex one of these days; I still felt like he was holding back on me!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? So I decided to take matters into my own hands. The next time he invited me to his house to play, I planned to wear a super sexy, laced corset with matching panties and knee-high lace stockings. I got to his house in my work clothes, said I needed to use the restroom, and changed into my sexy outfit. His reaction was priceless and I will never forget it; it made me feel like I was in complete power. I stepped out of the bathroom while he was entranced on his phone, and when he looked up his face changed completely. Like a child in a candy store. “Oh shit!” he said, “I am definitely fucking you in that.”

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 some foreplay downstairs, and after a few minutes, he suggested we go upstairs to his bedroom. He had a string of holiday lights on the wall around his bed, and turned them on along with some background music to set the mood. He went down on me stimulating my clit with his strong tongue and hitting my g-spot just right with his fingers. I came and kept moaning, “I want you to fuck me, I want that cock.” And I finally got it. That first time we had sex was especially fun because he discovered how flexible I was and the things I could do with my legs. But of course, I felt he came too soon. Fortunately, after he finished we started talking and cooled down for a bit, then started making out again. He pulled back and asked if I wanted to fuck again and I answered him by sensually sucking his dick and playing with his balls. He put on another condom and we had sex again. This was the first of many, many nights hooking up. We always did PIV with some D/S- he liked “punishing” me for being such a bad girl. We used my flogger once as well. Some sessions were longer and had more than one round, and some were just quickies when he didn’t even go down on me. We hooked up 2-3 times per week for a couple months. I almost always wore a special/ sexy outfit or lingerie. And we were both always down to try new positions or ways to fuck. I felt so desirable and confident, it was amazing. We mostly fucked at his place- either upstairs on his bed, downstairs on the sofa, or even one time on the kitchen floor! We also made a weekend road trip, got a fancy hotel room and had some awesome sex there as well. The 3rd month, however, got a little funky. We both had a lot going on in our lives… and we also had a bit of a friendship-related argument. I was afraid to lose this FWB situation that was going really well for me. The sex was great, I felt safe, and we were able to stay friends without things being weird or awkward. I truly didn’t think either of us had caught feelings. We didn’t see each other for almost 6 weeks, but just when I thought it was going to be over, we finally started hooking up again. A couple times a week for another few weeks. And it was like no time had passed. We got right back into it as if the long break didn’t even happen. However, more issues were coming up with our friends/ circles and things did not end well. I think our clashing personalities got the better of us, and he ended up texting me one day that he needed a break from our friendship and blocked me on all social media.

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? After everything has been said and done, I feel like I definitely gave too much. I would typically drop whatever I was doing to go have sex with him, but it was not mutual. He wouldn’t typically go out of his way when I booty called him. After each individual hookup I felt great, but when it all ended, I was crushed. After he blocked me, I realized I had caught some feelings, but I was more disappointed in losing his friendship /the decline in the friendship over the months. I hope that somewhere down the road we will meet again and at least be on good terms. As of now, I have no idea what’s next. I have spent so much of the last year with B. that it will take a bit for me to bounce back/ trust someone like that again. Even though I hooked up with other people while still seeing B. on and off, he was the only one I had a bit of a soft spot for.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting

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? 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? I talked to a few of my friends during and after, they did feel like the friendship was becoming more and more one-sided the longer we were hooking up. Being hard-headed, I didn’t listen to anyone and kept doing what I wanted to do.

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? Very

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? Somewhat

Why do you regret this hookup? Only certain aspects.Towards the end of it, I felt like I had gone from his very close friend to his FWB to this random/worthless chick that he was hooking up with. I am not sure how much it has to do with the sex, but during the year I felt he gradually lost respect for me, and by the end of it was being flat out mean any time we weren’t fucking. I wish I had more closure and I am still really sad about how it had to end, but I definitely don’t regret the actual sex.

What was the BEST thing about this hookup? We definitely had a lot of fun together. I loved seeing how excited he would get at my sexy outfits/ lingerie and the dirty things we said and did to each other in the bedroom We were always open to trying new things/experiment and the actual sex act (wants/needs/adjustments) was pretty communicative. I also loved how playful he was. I would go over to his house, knowing eventually we would always end up having sex, but he would first want to sit down and talk about how my day was, before ever-so-smoothly finding a way to transition to getting into my pants. Before things started going downhill, I felt it was the perfect balance of sex and friendship.

What was the WORST thing about this hookup? We never discussed expectations/boundaries after we started having sex. Yes, at the very beginning dating phase he was honest about who he was, but I think after making each other come so many times, we should have had some face-to-face talks about our feelings, other people we are seeing, etc. It kind of became a “don’t ask, don’t tell;” I honestly have no idea how many other girls he was dating or sleeping with. Which can be potentially dangerous in terms of STIs (though we always used condoms). I am also very sad to think that our FWB may have sabotaged the friendship we had built.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? During the months I was on and off hooking up with B., I slept with 4 other guys- partly because I wanted to convince myself that I hadn’t developed feelings for B., and also prove to myself that I don’t catch feelings by sleeping with someone. I was correct that I don’t catch feelings for someone by having sex with them, but I also discovered that I can have great casual sex with other people WHILE still having feelings for someone else. As I said, at the beginning of this, I had minimal sexual experience/ history. I have gained so much skill/confidence in bed in a very short period. Which slightly eases the pain of losing my FWB, because I know I will be able to get my nasty on when I’m ready.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? I think there is a very fine line between a close FWB and actually being in a relationship with someone. I felt B. was the one who controlled everything. He was the one who initially wanted to keep everything casual/non-monogamous. But there are some things you do together (that is NOT sex) that can exacerbate that closeness/feelings– like our talks about our hopes/dreams/fears, and going on long trips together– which makes that person a better partner as well. The more you know someone and the more comfortable you are with them, the better you can please them sexually. And I think there was a point that things just got too fuzzy and we had different expectations.

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? “Kiss your friends’ faces more. Destroy the belief that intimacy must be reserved for monogamous relationships. Be more loving. Embrace platonic intimacy. Embrace vulnerability. Use emotionality as a radical tactic against a society which teaches you that emotions are a sign of weakness. Tell more people you care about them. Hold their hands. Tell others you are proud of them. Offer support readily. Take care of the people around you.”
I found this quote and I thought it embraced my entire being; however, I found in my FWB with B., he needed that separation that sex is not the same as intimacy. Everyone is different and I believe casual sex can be very good, if done properly. And even if it doesn’t end well, don’t wish it didn’t happen. This was a very good experience for me that will help me grow into a better, stronger person.

What do you think about the Casual Sex Project? Writing all this out has been an amazing release for me. I tend to keep my truest, darkest feelings bottled-up, and I think although I still do not have closure, it helps to know a community of like-minded individuals may be reading/ commenting on my experience.

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