21 People Share Their First “Best” Sex Stories
Forget the very first time you had sex, here are 21 stories of the first time 21 people had their “best” time.
By Ally Sabatina
Virginity stories are tired. Over. They don’t mean anything. Virginity is fake.
What we know now holds not one candle to what we thought we knew when we were young, poorly dressed, over-accessorized, lacking in social media presence and sexual experience.
Most of us don’t know anything about sex. We think everyone is having more and better sex than us. Most of the time the sex we are having is nothing to write home about—a dance routine, an activity to divert attention from the now boring television program, just something to do.
What about the times where sex was good? What about the times you wanted to organize brunch immediately just to gab (you know, brag) to your friends about the seemingly endless and electric sex you are having … because you deserve it! What about the times everything seemed to fit together just right? What about the times they nibbled on your ear and did the thing you always want them to do … just like that? What about the times everything went just the way you wanted it to and you didn’t even know you wanted it that way?
That’s what I want to know. I want to know about the shockingly good one night stands. I want to know about college partners turned life partners after some very good orgasms. I want to know about the affair that you never told anyone about. I want to know about the sad but orgasmic last time with a vivacious yet toxic partner. I want some good stories!
And I’m a Leo. So I get what I want. So here are the 21 stories of the first time, 21 people had their “best” time.
(*Some names changed at the request of the interviewed.)
With my first boyfriend, though neither of us had transitioned at the time yet. I want to mention that this was the first time after I realized I was a girl. And like, I just was so in love with him at the time, and still am. We’re still together. We met sophomore year of high school on Valentine’s Day I went up to him and gave him a valentine and told him I thought he was pretty or something. When we fucked for the third or fourth time, it was senior year so we’d been in contact for at least a few years.
We were like, “open” at the time, and he was fucking his friend on and off. Now we’re like super poly and he’s got a girlfriend besides me and she has a few partners and I have 4 besides him.
And it started in my bed we were like making out and stuff. We got like really heavy into it n clothes started coming off. I wanna mention that this was like the first time after I realized I was a girl and he really fucked me in a way that made me feel feminine and adorable.
It was the first time I made him cum? And the first time he came with someone else ever.
So like we’d been kissing and grinding and stuff and clothing was coming off. [After he came, I left the room,] I came back to see him fully naked fingering himself on my floor which I thought was like the hottest thing ever. He was like, super intrigued about my d*ck piercing I’d recently gotten. So I let him touch me there even tho I was a little dysphoric and it ended up being really affirming and hot like gender-wise.
So, we had just come back from my birthday dinner. We had been dating for about a month and a half and unfortunately still had not had sex. Once getting back to his apartment we laid on his couch to watch a mindless TV show. We took a brief shower together to close out an eventful evening. Once clean we transitioned to his bed where we began making out. Shortly after rubbing and body contact began. Eventually we reached the point of penetration where we were consumed with laughs and smiles. The whole experience was much more enjoyable with someone that I knew longer than previous hookups.
I could feel the anticipation leading up to the moment. At first I was worried and anxious about his expectation, my expectations and whether it would be good. Throughout the experience we shared laughs and feel much more comfortable as time progressed.
It was the day I got to Missouri for the first time to see my [long distance] boyfriend. We’d been together almost 3 years. Definitely a best time for the both of us. Totally a first for us both and it made a huge difference when it came to sex. We were dating for almost a year and [this experience] kinda sealed our relationship. We had tried before, and I just wasn’t “opening up” I guess. But after a shower and some foreplay together it just slid in so easily. I think that it made us connect in a whole other level for our relationship. Made it seem real and that we were actually connected in a very personal and intimate level now.
I think the need for sex was very mutual at the time. We had been trying and it never worked and oral can only be good for so long, y’know? It sounds cliché but, it was like a rollercoaster. Every move we made would just get better and better and it was almost overwhelming.
I met a guy at a party, had sex with him that night. He was charming enough to have me believe we were going to enter a long-term intimate relationship. [He] expressed genuine interest in me as a person. Going out on dates. Meeting all his friends. Inside information on his family life and personal life like how he was adopted. Stuff that you don’t tell to someone who you’re not expecting to see next week information.
While it was good, it was really good for a week.
[Following this experience] I started recognizing my own needs. Sex was more than an activity that people do, it was supposed to feel good.
I was 24, in my first committed relationship in my life, constantly being ecstatic and confused about how good a relationship could be. I was making moves in my artwork, starting to regularly perform and felt like I was being supported from so many people, but also going through a really tough friend break up.
It was with my current partner, 4 or 5 months after we had started dating. They were always silly around me, but I had just warmed up to them and let myself be stupid and silly and vulnerable around them. We were still figuring out each other’s senses of humor and so it was scary but fun to poke fun at each other in ways that were new and unsure. I’d think that my partner thought this was a “best”, but I’m not sure it would be their first “best” like it was for me.
People can have a lot of “best”s of something, this just happened to be my first.
This felt like the first time I didn’t take myself so seriously. It was the first time I had had fun — for years, I had been having serious sex, pseudo passionate sex, sex for other people. It had never crossed my mind that you could actually giggle and goof around and have a blast while having sex.
I don’t even remember what we had been doing that day. Before we had moved into together, we would stay over each other’s houses more than a few times per week and smoke weed before bed. M@ gets especially goofy when they smoke, sometimes speaking completely in different accents — Russian, mid-atlantic film noir newscaster, British. It was a combination of the three that night, cycling through. It would annoy me to no end but they would eventually figure out how secretly amused I was by the absurdity. I would try to get them to quit by kissing them and we would both giggle and they would break into another joke, a new accent, and new bit. It continued through having sex, laying in bed after. I let myself play along instead of holding back finally.
I was 15, and he was the first guy to not treat me shitty. We waited until his parents left the house (at a playground on the swing set, but we could see where his parents would be leaving their road) before we did it. My exposure to sex before that started with sexual abuse by a different boyfriend about a year before, and hypersexuality (but never actual sex) after that to try and prove myself in some sort of way. We had talked about it for about a week. It wasn’t super planned, I remember that he stole a condom from his father’s drawer (and I had been on birth control for health reasons).
This first time was last year, so I was 23. My partner and I were together in bed just being silly and playful. We hadn’t had sex before and I think it was kind of a surprise to both of us when we decided in that moment to have sex. It was really lovely because not only was it safe and consensual and good, which I hadn’t experienced before, but also when we stopped my partner just said “hi.” And it was the purest most adorable thing.
To be honest, before this experience I thought I hated sex. This was the first time in my life I ever truly enjoyed sex or felt sexually satisfied. At the time, I was in the process of separating from my abusive ex husband and things were very difficult. It was amazing to have my partner for support during that time and also very nice to see that there could be Good Things even if I’d experienced such terrible things from so many people before.
[My partner is] is the first person I’ve felt genuinely safe and whole with in years. Also in general they’re just the most wonderful, brilliant, kind, soft, funny, lovely person I’ve ever known. They’re very special to me in all moments but especially in that moment when I was able to trust them with something that has previously / always been so scary for me.
I think it was really just that I felt safe and it didn’t feel expected or demanded. It just felt good. My partner and I are also always extremely playful and I was surprised to see that stay the same in our sexual relationship, but I’m so appreciative of that. My partner is always very focused on meeting my needs, sexual and otherwise, and that was very clear in this best first time.
I don’t remember any one specific experience so much as I remember a period of a few months when my partner and I had more sex and better sex than what I had considered normal up to that point, marked by more excitement, better communication and better understanding of each other’s needs. Once during this phase I distinctly remember at least one time when my partner and I snuck away from a group of friends I had over to my house to have a quickie in the bathroom, not something that I would usually do, I don’t even like the word quickie, but there was a certain magnetism present then that I haven’t really experienced since. It was also during this period that I first showered with a partner, which is a kind of casual intimacy I hadn’t really experienced up until then.
She was my girlfriend but we definitely didn’t have a “good” or “healthy” relationship. I felt confident in my sexual ability, like I had done it right and I could feel that.
I was a freshman in college and had met the man I would eventually marry. Must say it was my first super orgasm. I say super because it was the intensity was just undeniably what it should be. It was just also effortless. I was with the first person I really cared about. It was actually [full] of enthusiasm that I haven’t felt in so many years. It’s just like before you know it you’re falling all over each other.
Well, having had that first “super “orgasm”opened up the door to what sex was really about. So at the time it just encouraged me to have more of it!
He randomly texted me on Valentine’s Day of all days after not speaking since Christmas, when we last hooked up. I really wanted to talk to him and cuss him out, because I really wanted to be friends. So I went over, and it basically turned into us having a bottle of tequila. I finally confronted him about [how he treated me]. He finally confessed that it was because he really liked me, and I guess in what seemed like honesty pretty much laid the groundwork for finally getting inside me.
I’ve always had a weird relationship with sex, I guess I was having it wrong all the times before by prioritizing everyone else’s pleasure instead of mine. He ate my ass for what seemed like hours, and I thought my eyes would be spinning in my head forever. Then it led into some other kinks we never had talked about before, he just knew. I was getting smacked across the face while sucking him off, and his hands around my throat while getting fucked.
I realized some things while getting my ass eaten like a mango in summer. I don’t know if it was intentional or a sign from a higher pop priestess, but One Last Time was playing and as much as I tried to take our talk seriously, I knew we weren’t going to do this again, and I was really okay with it.
Sex is (almost) always fun. This time wasn’t even particularly wild and fun, just like good connection/passion/hard orgasm. Part of me feels like it will never be that good again. Also makes me less inclined to sleep with someone who I
am not strongly attracted to/have some sort of connection with. I have only had sex a few times since. All times very sub par. Honestly don’t have any desire to sleep with anybody right now.
It was just before my 18th birthday. I was a first year nursing student and me and my best friend were at his older sister’s apartment alone reading Joy of Sex and laughing. We split a quaalude and a joint and were fooling around. It was the first time a man had gone down on me. I also had a boyfriend who would go golfing with [my best friend]. We vowed never to tell him and we never did.
Very recently on a trip to Arizona to visit my boyfriend, we had been dating for a month. Only time someone has gotten me off and I didn’t feel nearly as dysphoric as other times.
It was my fourth time seeing this person. Early winter. Last year I’d say. It started we were gonna go in my car but
we ended up in my bedroom. I guess going in the car … we got stopped by the cops *laughs* so we went back to my house.
She seemed to be really interested … so I was like “okay (:”
It was only my second, I guess, partner. Just the way she touched me differently. It was more tender if you will. But seeing as though I wasn’t like regularly having sex, I could count on two hands the number of times I had sex. I thought I had enjoyed it my first time, even though I hadn’t cum. I thought it was good but like it was pleasurable … it was a night and day difference.
[At the time, I was] 24, I was working full-time as a manager at a restaurant and I was pregnant with my second child. I shared this experience with a co-worker, not my spouse and I hope it would be a “best” [for them] because it still occasionally happens to this day.
It was the first time in my entire life that I honestly felt free during sex. He was so into me, I had never experienced someone wanting [me] that bad before. I felt like a fucking goddess the entire time, even though it was in aforementioned restaurant’s dining room.
It made me happier all around, I craved sex with this person instead of my spouse though, putting a damper on our already failing relationship.
I’m not sure how it came to be because I thought I was never really physically attracted to him, we got close because I let my guard down for that reason. He was so sweet and caring towards me in my heightened emotional state. My relationship was dwindling at home and being pregnant, I was full of hormones and hate for my significant other. I didn’t want to be pregnant again.
Anyway, my coworker had become my rock. I was working 60+ hours a week and he seemed to always be there. I truly believe I fell in love with him because still, to this day, I think about him regularly. We see each other and have mind numbing sex every couple months but it’s few and far between because I’m still married.
I was 20, studying abroad in my junior year, and was at the end of an abusive friendship. This was a full year after my first relationship ended, which had also been abusive. I was raped by a halls corrector* shortly after arriving at my host university.
The person I shared this experience with was a student and secretary who had helped me move in. I met him when a bus dropped me off at the residence hall I was supposed to stay at. The rest of the students on that bus were let off at all the previous halls, and the student-secretary was the first person I met. I was shy. Not just because, I tend to be quiet and distrusting of stranger, but I thought he was handsome and was being very forward and friendly. He carried my luggage up to my room and gave me everything I needed for moving in.
He showed interest in me and took me out to a club with his friend and got me VIP. I actually rejected him that night and sought him out on another evening. It was a one-night stand.
It was the “best” because it was my choice, unlike the sexual abuse and expectations I had faced prior. I hadn’t had sex since [my assault] other than masturbating. I was terrified beforehand and felt nervous and scared afterwards but I don’t regret having done it.
[Following this experience,] I was more open to being comfortable with my sexuality. I’ve become less sex-repulsed, but I still feel nervous or scared at physical contact that seems sexual. Sex was fun, but I decided to wait for a partner I can take the time to get comfortable with, so that I can [share my trauma] in case I do start panicking.
We dated from my age 17-19, his 19-21. Even though I had slept with 2 other people before him, and having [not great] sex for a year or two, he was a virgin for even oral sex when we started dating. So we did a lot of exploration together. We had been dating for near 3 months at the time of this experience. It definitely brought us closer together and we fell super hard in love.
As teens in Marin, we didn’t have a lot of places to have sex. We would often try to find outside places or cars to hook up in. This time we were up on a secluded part of a hill hanging out on a blanket. We have a lot of open space in Marin and it’s pretty. He laid out a blanket and started going down on me. I was still wearing my spaghetti strap tank top, pants off. Something about the way he was licking my clit and the love energy he was transmitting to me felt fantastic and I had my first orgasm. It felt so good and that experience definitely made me slut.
I don’t think we had intercourse that day or I did anything in reciprocation. It was all about me and him pleasuring me. That’s the way I like it. Pussy oriented sex is far superior to boner oriented sex.
After two partners who left me feeling dissatisfied, this was a breath of fresh air. It was starting to feel like [sex] wasn’t even worth the risk of pregnancy and STIs, and then meeting G changed all that. I was super open to sexual stuff after that.
After we broke up, I ended up dating a girl and having a triad relationship for the summer. It definitely opened my eyes to just how diverse and interesting sex can be with the right people.
At the time my marriage had ending and I had reconnected a few years prior with one of my best friends. We met when I was 14. He was my first crush and kiss. We had lost contact in 1998 and in 2007 I ran into him. We had been just casually talking and hanging out for a few years but one day he kissed me and this led to the most amazing sex in the park. I don’t know if it was the park, or the sneaking/potentially getting caught or the fact that I hadn’t had sex in 17 months but it was amazing, and 9 years later he continues to rock my world.
He was into me, I have never felt to sexually attractive, so desired, and so wanted in my life. It was very intense and passionate, and I am sure the fact that we were both married played a large part., at the time I was overweight and not feeling good about myself. I had always had a crush on him and wanted to be with him so I think this 20-year fantasy I had about him just all rushed in on me.
I had gotten married very young so had only been with one man other than my husband, I didn’t have a lot of sexual experience, and my values, and upbringing blocked a lot. To this day, he still stretches me sexually.
The first sexual experience I ever had was emotionally very positive. It was with my best friend at the time, whom I’d known and been very close to for two years beforehand. Physically it was a little uncomfortable and awkward, because we didn’t know what to do, but we laughed through all of it, breaking into hysterical giggles at each other and the situation. It also moved very slowly, and we didn’t do anything that a cis het couple would be likely to define as sex. And we’d been talking about it for a few months before acting on it or even seeing each other (we lived in different states).
The other person was expressively queer, and I didn’t really yet know that I was too. I was incredibly depressed, and this person was one of very few I talked to often, at the time.
It took me a long time to love my body just as it is. I’ve always had a lot of medical problems, specifically autoimmune diseases. In autoimmune disease, your own immune system is destroying parts of your body. My body is hurting itself, and for a long time I felt like my body was hurting *me*. I’ve always also been a big girl and when you are, you’re often expected to apologize for or explain your body, or acknowledge its flaws before you are allowed to celebrates its assets.
It was the best because it wasn’t about someone’s boner. It was about me. And her. My body was celebrated and central, not a weakness to be used for someone else’s pleasure and then harnessed later for their revenge. It was because she thought I was hot (and I her). It was also because of the insane amount of sexual tension we had built up while I figured out of this was something I really wanted (even though I already knew I did.)
Besides the obvious part of it being my first time with a girl, it was also possibly the first experience I had where the majority of the activity wasn’t spent doing something for the other person. It was with a person I felt I could trust. Someone not wrapped up in the toxic, misogynistic culture that was pervasive at my school. It was with someone who also didn’t like how boys treated girls. It was with someone who would never say anything mean about my vagina because she had one too. It was with someone who could not hold my female-ness — something that, at my school implied inferiority, weakness, vulnerability to cruel criticisms, and value derived or degraded only by sex — against me. Because all of those values had been unfairly placed on her too, so she could, and would, never use them against me.
We were just getting to know each other. I had just broken up with my boyfriend so that I could hook up with her and see where things went without feeling super guilty, I was 16 or 17 at the time.
I’ve been exploring tantra and maintaining sexual energy post-orgasm rather than releasing it and getting over it. Prior to this, sex wasn’t an activity for me… it was for them.
I’m in a new relationship with a new man. This was the first time, outside of my first husband, someone who feels equally invested in how I feel before, during and after. We are different in that we have conversation and that brings about a healthy sexual relationship (a first for me).
My perspective has definitely changed. Growing up and as young women, we think that it is a way to keep a man. And really it’s more of a disadvantage to me–to undervalue myself to the point of pleasing a man. I did more damage than good in my time. I understand the importance of waiting to have sex now.
Granted one night stands can be great and they can be fucking awesome. Unfortunately for me, no one night stand has stayed that way. I feel better with my partner being satisfied. It’s been ingrained in me that way … as a black woman. I’ve talked to my doctor, in the past few years since having my youngest … I can’t get there. If he shifts or moves in such a way, my moments gone.
For the first time ever, I feel I’ve found someone who’s vested and cares. That makes it easier for me to achieve what they want me to achieve (and that’s an orgasm). I’ve never worked on a relationship before so ultimately this has been a huge moment of “best” “firsts” for me.When we have that … it is magical. There’s something in the connection that I have with this person, while the sex might not be “there” yet, it’s still the best sex I’ve had because it’s with someone who sees me, not an object.
Author Bio: Ally Sabatina is watching Barefoot Contessa rather than writing her author bios. In 2015, she replaced Xanax with cooking shows as a salve for panic in an unfair world. She knows the dogs on her block better than she knows her human neighbors. She works, freelances, lives and shares unsolicited opinions in Philly and on the internet.
Featured Image: Photo by Gabriel Matula on Unsplash
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