Lesbian Sex: 24 Women Share the Their First-Time Stories 

We waited to have sex. 

"I'd never had sex with a woman before but knew it was something I wanted to try. After a particularly bad breakup with a cis man, I found myself at a lesbian bar in my town. I felt comfortable immediately and hit it off with a woman, H, who was easy to talk to, attractive, and witty. We had a few drinks and exchanged numbers, and I was eager to see her again. We had a few flirty phone calls and text messages before meeting up. Long story short, I was fully honest with her about my lack of same-sex experience and she wanted to take it slow. After a few great dates, we ended up at my apartment and kissed for the first time, which was explosive. The sex was incredibly satisfying—something I'd never really said before—and we ended up in a monogamous relationship for almost two years. We parted ways amicably and we're still good friends to this day. I'm exclusively dating women and will always credit H for help[ing me come to terms with my sexuality. —Krista, 39

We nervously explored each other’s bodies.

“Though I had flirted with women through college and my 20s, I was in a long-term monogamous relationship and never acted on my interest or desire to be with women. In our early 30s my husband and I decided to open our marriage to some sexual exploration and went on a date with a couple. We immediately hit it off. While the woman and I kissed that night, we didn't take it any further—I think that we were both too nervous. She also hadn't ever been with another woman. We decided that we didn't want the first time for both of us to be with our husbands; we wanted to concentrate on each other, so we told them we were going to get together and that they weren't invited. I sent my kids to school, and when her baby fell asleep for his daily nap, she called me. I came over, and we shyly and nervously explored each other's bodies. That was the first of many times that we did that, and it began an over-a-year-long romance between the two of us.” —Jessie, 42

It felt like some kind of rite of passage.

“I had come out as bi about a year before but still hadn’t kissed a girl. I got cast in a play where I’d have to kiss a girl onstage, and I was unhappy with the thought that this would be my first kiss with a girl, so a friend of mine offered to kiss me first. It was just a quick smooch in a hallway of a dorm building, but it felt like some kind of rite of passage as a queer woman. The first time I really hooked up with a girl, I was hooking up with a trans woman that I had hooked up with before she came out. It was sort of like I was actively reframing things through a queer lens while we were hooking up. It wound up going pretty well because we’re together now. It’s a strange experience being a queer woman who’s never slept with another cis woman because a lot of times, lesbian sex is framed solely around the presence of two vaginas. It sometimes makes me feel like I’m missing out on some big part of being a queer woman, but ultimately, I’m really happy with my girlfriend and we’re just as gay as anyone else, so I try not to worry about it.” —Julia, 21

People thought I was more experienced than I was.

“I spent my 20s in a long-term monogamous relationship with a man, and I hadn’t dated much before that, so when we decided to open up our relationship, I was excited to explore my interest in other genders. I’d already been teaching sex education for a few years and had begun cohosting sex parties with a colleague, so my run-of-the-mill nerves about having sex with a woman for the first time were multiplied by people often thinking I was more experienced than I actually was. It took me a while to feel comfortable moving past making out with women, but one night, after an event I hosted, a woman I’d been seeing decided to stay over and we had sex. I was still super nervous and struggled to get out of my head a bit, but having good communication helped, and it was a really great experience.” — Rachael, 32

I was in the bathroom in ninth grade.

“I was in the bathroom in ninth grade with my best friend and our mutual close friend. When my best friend went into the stall, the other girl pushed me against the wall and kissed me. I got butterflies so hard my stomach hurt. I knew that every kiss with any boy before that was nothing compared to what I felt in that moment.” —Danielle, 35

I stumbled through asking her to hang out.

“The spring of my senior year of college, I met my first girlfriend after coming out as queer to my close friends the summer before. We met at a meeting for an on-campus mental health organization and ran into each other at a coffee shop a few days later. At the encouragement of her roommate and our mutual friend, I stumbled through asking her to hang out. She came to my dorm room for a movie night, and we were watching a documentary before she turned to me to ask if she could kiss me. That was the first time anyone had ever asked me if they could kiss me—something I found oddly endearing. We laughed and giggled through our first of many awkward hookups before finally getting the hang of it, and a few weeks later, I asked her to be my girlfriend.” —Anisha, 25

I threw caution to the wind and said I was game.

“I grew up playing softball, and even though I occasionally felt attracted to women, I figured that I couldn't possibly be queer since, within the context I existed, being a lesbian (no one I knew was bisexual) meant that you were butch, which I'm not. I chalked up drunk make-outs with gal pals to ‘drunken college fun’ and never really gave it much of a second thought. In my early 30s, I was single and on dating apps for the first time. I matched with a guy who later said that he and his friend with benefits were looking for a third, so I threw caution to the wind and said I was game. As the day approached, I became increasingly stressed about being awful at performing oral sex on a woman—I knew what I liked and what felt good, but I wasn't sure how to translate that knowledge to someone else. So…I googled it. I ended up having a fun first experience, which opened the door to a whole new side of my sexuality. As much as I love giving a guy head, I don't know how I lived before going down on a woman. Recommend.” —Erin, 36

She had no idea it was my first time with a woman.

“I was at a fetish play party as a single bi woman. Another woman wearing a corset told me my hair was lovely and asked if she could play with it, which progressed into a massage and her asking me if I liked women. I said yes. I started with clit-rubbing and fingering her G-spot. She really enjoyed it, and until I told her afterward, she had no idea that it was my first time ever with a woman!” —Cy, 26

Friends had told me I was “just curious.”

“I had always known I was bisexual, but my ‘gayer’ friends had repeatedly told me I was ‘just curious’ and ‘being ridiculous.’ It made me feel terrible, and I think it really diminished my confidence in that area of my life. So through high school and college, I only dated men. I was at a party in my mid-20s where the host’s roommate was in a women’s rugby league, and the whole team came. I had never felt so queer. The men’s team was there too, apparently, and I didn’t even notice. I had a few drinks for some courage and was chatting with the cutest lesbian in the world. Then the power went out very suddenly. I asked if I could kiss her then, in the dark, and we spent the rest of the party making out in what I really hoped was a dark corner, but which turned out to be where the extra beer was. Not very subtle. We went on a date, and she was totally awesome, but I didn’t have the confidence back then to navigate a relationship with a woman for the first time. I told her the time wasn’t right for me. I didn’t have ‘actual sex’ with a woman for a while after that, but I certainly have now, and I can tell you with confidence that I’m definitely bisexual.” —Rachel, 31

I told her I thought we would end up making out.

“I was studying abroad in South Africa when my roommate revealed that she was a lesbian. Having been struggling with my own sexuality, I boldly told her that I thought we would end up making out. One night we were hanging together on her bed listening to ‘Something Beautiful’ by Needtobreathe when I kissed her. It instantly clicked at that moment why things had never worked out with guys. This make-out session led to four months of sneaking off to have sex in corners of our apartment where our other roommates wouldn't see and hooking up in public restrooms. Nothing ever came of us besides a friendship, but I've never turned back.’ —Tayla, 23

I took a chance and kissed her.

“I'd never really thought of myself as anything other than straight until a friend of mine said she liked me and it was too bad I didn't like girls. I laughed it off, but something in my head went, ‘It is too bad I'm straight!’ Later that evening I took a chance and kissed her while we were watching a movie. Then one thing led to another, which led to our dating for a year and a half. I had always assumed I had to be straight because I like men. Now I happily identify as bisexual, and a lot of feelings and a few dreams from high school make a lot more sense.” —Cathy, 35

I wasn’t sure about my own identity.

“This girl and I had been hanging out for a while. I knew she was gay, and I wasn't sure about my own identity. We were having a sleepover one day—as we did most weekends—and she kissed me. We made out, and then we started having sex on a regular basis as friends with benefits. Since her, I've only been with women.” —Lauren, 23

It was my first time having a threesome.

“It was my first time with a woman and my first time participating in a threesome—so I was doubly nervous. My ex-boyfriend arranged it, and I trusted him and his taste in women. The woman was very sweet, curvy, and had amazing lips. We sat around watching silly porn for a while, no one making any moves, and then eventually she just attacked me. She straddled me, and I was shocked at how soft she was everywhere. The threesome didn't really end up being very threesome-ish, as we kind of just took turns in the end—but it was pretty exciting to experience a woman's body for the first time. Neither of us had the guts to go south of each other's waists, though. We stuck to kissing and breast play. Since I consider myself pretty much straight but fascinated by the female body, I was happy with that. I had a second threesome a few years later, with different people, and I went down on the woman. It didn't really do anything for me.” —Portia, 36

I wanted to sleep with other women.

“I had a crush on this girl, and she knew it. We were very good friends, and her boyfriend was my close friend. One night we all kind of made out, and I thought, Girls are good kissers. I've identified as bi since I was 16, so it reinforced that. I wanted to sleep with other women, but it just didn't happen.” —Jen, 39

I don’t need to question my sexuality anymore.

“I was trying to plan a threesome with this guy I was seeing. He ended up matching with this girl on Tinder who agreed to a threesome after they got to know each other a little better. We friended each other on social media and found out that we had a ton of interests in common. After a few weeks, she decided she wasn't into this guy anymore, but she still wanted to hang out with me. I was so nervous because I had never been with a woman before. I planned on this guy being my buffer. I'm bisexual, but I didn't come out until my early 20s. I voiced this to her, thinking it would be a turnoff that she would be my first sexual encounter with a woman. She was more than understanding. A few weeks later I was at a bar with some friends and called her to see if she would want to see me that night. I took a Lyft to her apartment about an hour later. We sat on her couch drinking wine, I pretended to like her cat, we flirted for a while, I was nervous. We took it to the bedroom, and I had one of the most awkward, thrilling, skin-tingling sexual experiences of my life. It's still hard for me to date women, as I feel like I'm so new and clueless. But now I know I don't need to question my sexuality anymore.” —Sarah, 25

I had considered myself mostly straight.

“I had gone on a few dates with an interesting late-30s couple and went over one day for a planned threesome. We drank nice cider and they gave me greens from their co-op before we even moved to the bedroom. I’d had only one crush on a girl and considered myself mostly straight before then, but a few hours later, I fully came to terms with being attracted to men and women after an incredible night focusing on the dude’s female partner.” —Shannon, 24

Every woman to me is an untouchable goddess.

“I had come out as bisexual my senior year of college and was (still am, actually) clueless on how to pursue relationships with women. The fall after graduation, a woman and I matched on Tinder. We really clicked over the chat, so she decided to come with some friends to the coffee shop where I worked and meet face to face. I was terrified but also really attracted to her. She was like a tiny Jodie Foster. We made plans, but they fell through. She had never seen Spirited Away, so I invited her to come over and watch it with me. We were spooning, and with my position as the big spoon, I was too terrified to make a move. Then we switched positions, and I love to say that’s when she spirited me away. (It’s okay to roll your eyes at all that corn.) I had never felt that way before. She was so soft and gentle. It felt right, and I felt like a teenager again. I fell hard, but although she liked me, she wasn’t feeling as intensely as I was. It makes sense, though—I was going through a sexual awakening that she had experienced years before. We ended up having a dramatic breakup of sorts, where I stormed out of a coffee shop with her calling after me to come back. Years later I still struggle with dating women. I think my issue is I put them all on pedestals: Every woman to me is an untouchable goddess. In reality, they’re human just like me. I need to get over that hurdle sooner or later because I’m so over navigating the toxicity of men.” —Maddie, 26

I must have gone down on her at least three times.

“I was on a cross-country road trip, found myself in Texas, and was frustrated by how many men admitted to never having been tested for STIs before. Unwilling to negotiate my hard boundary (I don't hook up with anyone who hasn't been tested within the last six months) but still wanting to scratch a sexual itch, I decided to try having sex with women. I made a very honest Tinder profile stating that I was inexperienced but a very enthusiastic and reliable hookup. It didn't take long until I matched with a very beautiful lesbian who had a thing for 'newbies.' I was so excited to try something new but still a little nervous, so we got stoned and I asked her if it would be okay if I just explored her body. I ended up giving her a full-body massage with oil to see what she liked, and I've must've gone down on her at least three times. I totally get why men love giving head now. It's addictive!” —Dana, 31

It felt totally natural and right.

“I'd always had a sneaking suspicion that I might be queer. When I was 21, I went to see the movie Chocolat in a park with one of my fellow teammates from my swim team. I knew she was gay; I definitely had a crush on her. We both have type 1 diabetes, and that made me feel an instant bond with her—we could check our blood sugars together! We made out in the middle of the movie, right there in a huge public park. It felt totally natural and right. I drove her home and nothing happened from there. Still she and I are still friends, and I officially came out as queer at 27.” —Bonnie, 29

I was exploring some platonic kink.

“My first hookup with a woman was with my housemate during college (cue college try jokes). I was exploring some platonic kink with some housemates—asking them to spank me with a sex toy I recently acquired—she told me she could spank me...platonically. After getting drunk together one night at a party our house was hosting, I asked her if she wanted to spank me...not platonically? She was surprised but said yes, and kinky sex ensued! All the time our phones were buzzing with our friends asking where we had disappeared to! The next day I sent her a message saying what a good time I'd had, and she replied that she was getting back together with her ex-boyfriend. I’m hella queer now, though, so not all is lost from that experience!” —Eva, 23

I assumed you just “knew” if you were gay.

“I had always been with men in the past but never in much of a relationship—I can’t say I was ever really into it or enjoyed it. In fact, at times, it distressed me. However, it never occurred to me that I might fancy women because I assumed you just ‘knew’ if you were gay. However, about five years ago, I went on lesbian dating apps and had a few dates. I found them attractive but didn’t feel any kind of spark. Something, though, made me keep dating. Then I got a ‘like’ from one woman whose picture really piqued my interest. We started talking online and messaged each other constantly for two days before meeting, even though we lived over 100 miles apart. There was instant chemistry. We’ve now been together for nine months, and I feel like I’ve finally found who I am and who I am meant to be with. I am definitely gay. I guess it’s just not as straightforward for everyone figuring out their sexuality.” —Eleanor, 39

We both orgasmed several times.

“My first time with a woman, I was 20 years old and she was 31 years old. We met through a mutual friend. Our first time was very nerve-wracking for me, but since she’d had plenty of past experiences, she led the way. I'm usually quite submissive, regardless of my partner's gender, so it worked out great for me! We both orgasmed several times. She topped and I bottomed. We went to her apartment because her shower was huge, and that's where we started our little ‘session.’ We saw each other again a several more times after, twice with an additional partner (a cis-gendered man). 10/10 women make amazing sexual partners, IMO.” —Sam, 22

She felt like someone I’d known forever.

“We met at this communal art project, and there was this instant connection. We later matched on Tinder. I had just kind of come out to friends and family that I was bi, so she had me over and cooked for me, and the connection and fireworks were so, so strong. It wasn’t long before we started making out, and we couldn’t keep our hands off each other. This led to the bedroom. The experience felt natural—she felt like someone I’d known forever. She was the most beautiful, kind soul I’ve ever met. She was a lesbian since she could remember, and I was just coming out. I wasn’t sure if I was ready to even be in a relationship. It was bad timing. I wish I had more courage or just more experience. At that point I felt super intimidated, but not by her, just with all the thoughts and things. I never really spoke to her about it. She is a ball of sunshine who is an amazing cook. She most definitely stole my heart. The experience was so natural it still boggles my mind. It’s something I think about often.” —Andrea, 31

I had this shattering realization that I had to be queer.

“My first memory of knowing that for sure I was queer: A (male) friend took some of our friends to a birthday party for a lady he had a crush on. She was a professional ballerina. She and I ended up really hitting it off, and then she followed me into the stall when I went to the restroom. What happened was definitely not PG-13. It was the first time I’d had full-on oral sex with a female. It happened so naturally and I was so good at it! I had this sort of shattering realization that I had to be queer. At that time gay marriage was not legal, and it was not as accepted as it is today, so it was a very complex and difficult moment for me.” —Carrie, 39