If Only I Had Known!



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? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Administration
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Free
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? 0

If Only I Had Known!

How long ago did this hookup happen? April 2015

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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 was tall, fit, short brown hair, brown eyes, a little bit of stubble. Very good looking in a very rugged and casual way, just my type. I met him for the first time in a club in the town where I went to university. It was a country themed night, and the girls and I were ready for dancing and possibly scoping out guys. I had been single for about four months and had decided, (and prepared) to find someone to take home.

My friends and I enter this club, have a few drinks, dance like fools, and steal a few straw cowboy hats from abandoned tables. Then I see the guy I’ll take home. I don’t think he’s seen me yet, so I’ll have to figure out how to approach him. My usual, admittedly cowardly tactic, is just to draw my group closer to his location, dance next to him, maybe “accidentally” bump into him, or make eyes and smile, or let him catch me checking him out then smile and turn away shyly. He would be my 6th sexual partner, but I still hadn’t mastered the art of making the first move; simply lacked the courage. This unfolds for me in two ways; if he is looking for a hookup as well, he’ll notice my looks and smiles, and draw closer, maybe start dancing with me without a word, maybe shout hello in the very loud club. Or, if he isn’t interested, he’ll ignore me or wander off and I’ll find someone else. Part of why it took me so long to get used to making the first move was my concern of pressuring the guy, which often isn’t considered enough, so him making the first move lets me know it’s okay to proceed. Well, he was interested.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began at the club. We danced a little, inhibitions loosened by beer, then danced closer. We bought each other drinks, made terrible smalltalk, and began kissing. My back against a rail between the bar and dance floor, I pulled him into me and we made out for a while. Felt each other up, little stuff like neck and back at first, then graduating to me putting a hand in one of his back pockets to feel up his butt while he hooked a finger on the waistband of my shorts, dragging it across my lower belly. I pull him in and he presses himself into me, gently rubbing his newly acquired erection against me.

At this point I decided I should probably take him home, before things get too inappropriate for the public setting. Which I had planned for before even leaving my apartment earlier that evening. It was part of my process, to help keep me safe and to make sure that I wanted it. If my room is filthy and I haven’t shaved, I won’t be giving guys a chance to get very close. But when I know I want sex, I make sure I have condoms in my bedside drawer, I make the place presentable, I groom myself and wear something lacy. Then when I get to a club, I find a guy I am interested in before getting too drunk to judge well enough, and once I’ve secured the guy we let loose and just have fun. Of course if I change my mind it’s easy enough to bail out, but it hasn’t been an issue yet.

By the time we were ready to leave the club, it was actually about to close, so my friends and a few of his (some of my friends had paired up with his group) went next door to a pizza place for a sobering snack. In the bright light, quiet atmosphere, and surrounded by my protective clan of girlfriends, I could get one last good look and conversation with him to be extra sure I had made a good choice. Seating was low so I sat on his lap, and when group conversation lulled, I asked him if he’d like to spend the night at my place, a mere 15 minute walk. After a quick goodbye, and the girls all agreeing to text each other when we all got home, I towed my catch home. The walk was short (although he joked it took forever) but gave enough time to learn a bit more about him. He was a couple years older than me, taking some marketing courses at a neighbouring college. We talked a bit about our friends, joked that we hope another pair between our groups has fun tonight, and as we enter my building I let him know to be quiet as my roommate is sleeping. After food and a walk, most of the alcohol has worn off, and while we are still a bit tipsy there was no doubt as to our mutual desires and intentions.

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? After a quick trip to the washroom to freshen up and to text my friends that I’m safe at home, I meet him in my room and we kiss again. We continue the pattern of slowly feeling each other up, becoming more firm and excited as we explore each other. My hands go back into his back pockets and I pull him into me. I grind into his erection again, and when he hooks a finger down my waistband I smile under the kiss and take the shorts off. We continue undressing ourselves and each other, moving towards the bed.

He backs me into it, gently guides me down, and lays on top of me, kissing deeply. We each are down to our underwear, but I’ve removed my bra and he goes to kiss my breasts and lick/suck my nipples. I have them pierced and he comments positively as he plays with them. It feels good, so I tell him so, and raise my hips to grind on him again. We use our hands on each other over our underwear. The foreplay continues, and in a mix of conversation, experimentation, and action/reaction I learn that he is dominant and a biter and I am submissive and like it rough, so we’ll get along wonderfully. As I am on my back, he moves his kisses down my body, and removes my underwear. He begins to slow and tease the more I moan and react, a favourite of mine during oral sex, making me really want everything he gives me. He was very satisfying, taking his time to make sure I really enjoy myself, probably feeling pretty good about himself too as I try to stifle my involuntary noises and writhing in pleasure. I consider myself very easy to please, you do not have to be skilled to get me off, but he was, so I climaxed easily. Afterwards, I ask if I can return the favour, and do so eagerly, wanting to give him as much pleasure as he’s given me.

Giving oral turns me on, so by the time he is close to orgasming and stops me so he can continue with sex we are both very eager. He lays me on my back again, and after a quick pause to put on a condom from the drawer, we have some incredible sex, full of kissing and biting and squeezing and nails down the back, one of the most delightful experiences I have ever had and by far the best one-night-stand of my life. By the time we are finished, panting and sweating, collapsed on the bed side-by-side, we are both very tired and ready to pass out. I make one more trip to the washroom, and get us some water, and after a few lighter kisses, giggles, and praising each other for the experience, we fall asleep.

We wake up early to the sound of his phone, and he says he’s received a text from his friend. He says his friend’s mom is in the hospital, and he should go. He, unnecessarily, shows me the text to prove it, lamenting that it sounds like a very corny day-after excuse to ditch me. I tell him it’s fine, I believe him (I did about 70%, I know some people can be very awkward about things the next day and I figure I’ll just play along to make it easy on him) and I ask him if he wants me to call a cab. He says he can take a bus and I direct him to the nearest stop a block away. He dresses himself and thanks me for the night, kissing me goodbye. I give him a playful smack on the butt as he goes out the door, then I return happily to bed, knowing I’ll probably never see him again, but not really caring.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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? When I woke up later that morning, I felt satisfied and happy. I then thought it would have been smart to have asked for his number, or even last name to find him on Facebook, because he would make an absolutely fine friend-with-benefits with such perfect sexual chemistry. As I had no way to contact him, I decided to put out a meagre “missed connection” post on craigslist but didn’t expect (nor really cared) to get a reply. By the time the next weekend rolled around he was simply a happy memory.

It wasn’t until a year later when I discovered that Facebook messenger had a hidden “other” folder where messages sent by people not on your friend’s list went, did I see that he had attempted to contact me the day after the hookup. He had said he hoped I had a good night and would like to get a coffee. I laughed, and lamented, because a year had gone by, and I never saw the message. By then I moved back to my hometown, I had a big summer backpacking trip planned which I had just broken up with another guy for, so it was most certainly too late to take him up on the coffee. I didn’t mind that so much, but I have always felt a bit bad that I never got the message, because he may have felt bad or rejected when I simply didn’t know the messages were ever there. If only I had known! It is my favourite story to tell my friends when we talk about “the ones that got away,” because I am known for being technologically challenged and it makes for a pretty good joke among us.

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, I was feeling lonely, Power / Dominance, Submission / Relinquishing power

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? I told the friends I went out with, it’s always a burning question when one of us takes a guy home if it went well. Later on, after I found the messages I told a few more friends and we all laughed at my folly.

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

Did you get emotionally hurt as a result of this hookup? Not at all

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? I discovered how much I enjoyed pushing the pleasure/pain boundary which has positively affected my sexual exploration with new partners since the interaction. It has led to increasingly satisfying sex and a heightened openness for trying new things that partners have wanted to explore and introduce me to.

What was the WORST thing about this hookup? I feel terrible that he may have thought I was ignoring his messages instead of the fact that I simply didn’t know I had any for so long. He was a very sweet guy and I hate to think that he may have felt bad or embarrassed if he perceived it as rejection, because I probably would have accepted his invitation.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It reinforced my ideas that casual hookups can be pleasurable, safe, satisfying, and enriching. I learned new things that I have used in new relationship, both casual and serious, and it has had a positive effect. I also try not to use alcohol as a way to lower my inhibitions as much. While it makes it easier somehow, the culture of a drinking/sex culture isn’t a safe one and while I have never had a regrettable instance, it is always best to be cautious.

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? Sometimes, even two years later, I use the memory as inspiration when I want to masturbate. It was just that good.

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? I think if casual sex is done safely, respectfully, and within one’s comfort zone, it can be a fun and rewarding experience. I think some people have a negative view on casual sex, and while it has been better in recent years, there are still negative attitudes that I believe to be misguided. I also notice that it is still disproportionately seen as more negative for women than for men, but this too has been changing and I believe that with time and education, stigmas will become a minority focus.

Alcohol is also a common crutch for people who are shy or awkward about making sexual advances in a casual setting, which can often lead to unsafe situations. While it is much easier to ask someone for sex when you have been “letting loose” with them than it is to soberly walk up to someone to do the same thing, I hope that dismantling the stigma around casual sex will improve this situation. Substances should not be used as an excuse to have sex, if you already know you want sex. It will also help eliminate the use of alcohol as a coercive substance if the connection between sex and alcohol is broken.

What do you think about the Casual Sex Project? I think it is a great idea to hear first-hand stories from all sides. It can be difficult to understand casual sex, especially when we still perpetuate so much shame and so many unfounded myths about sex in western culture. By opening up the conversation and allowing anecdotes from all kind of people with all kinds of experiences, we can begin to dispel these myths and better understand how to promote safe and healthy sexual relationships.

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