25 Women Describe Their First Time

Illustrated by Abbie Winters.
In our society, “virginity” is a loaded word, and we place a lot of emphasis — and pressure — on losing it. As a result, having sex for the first time becomes a major milestone for many women, and the memories of those often awkward, sometimes painful, occasionally funny moments tend to stay with us.
To show how diverse people’s sexual experiences can be, we asked women (names in quotation marks have been changed) of various backgrounds to tell us how old they were when they lost their V-cards — and what it was like. Some of their first times were great. Some were bad. Most, truth be told, were somewhere in the middle. And, they were all pretty different from what you’d see in the movies.
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1 of 25
"Casey"
Age then: 18
Age now: 23

"It was extremely painful and highly regretful. I did it with a boy during my school's senior week. He had a girlfriend, was sleeping with one of my friends, but also had sex with me that weekend. I was very drunk, and I hated every single second of it. I wish it never happened like that, but I guess it's a good bar story."
2 of 25
"Sally"
Age then: 17
Age now: 17

"I lost my virginity with my current boyfriend (my only other boyfriend), and I'm so happy I waited. The first time was fumbly and we struggled putting the condom on so we gave up. Tried a few more times after that, and when it eventually worked, it was nothing mind-blowing and I don't really remember it explicitly. I just remembered that it happened and I wish we'd gotten lube."
3 of 25
“Emily”
Age then: 20
Age now: 27

“I was just starting [to accept] that I was into women. At a lesbian bar after work, I met this hot butch who bought me four rounds of shots. We [ended up in] the bathroom together, and...we hooked up, hardcore. I was nervous, but overall it was pretty awesome.”
4 of 25
“Millicent”
Age then: 17
Age now: 30

“I was at this hot surfer boy’s studio apartment in Boston. He was 23 — I’d met him on a trip to Bermuda during my senior year in high school. I’d waited so long. I felt like I was in love with him.

"After it was over, I kept waiting for him to say something deep and meaningful, like, you know, ‘I love you.’ Instead he looked over and said, ‘Damn girl, your shit’s the bomb.’”
5 of 25
April
Age then: 16
Age now: 33

“I was dating a Jehovah's Witness drug dealer who would get high and then get sad that I was going to hell because I was Catholic. But, I wanted to have sex so bad that I didn't care. We got drunk and climbed onto his waterbed. It was broken, so he’d laid a twin mattress over it. I had to try very hard not to get seasick while he jammed a rather insanely large penis into my vaginal area. When it was done, he cried again because I was going to hell.”
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6 of 25
Carmen
Age then: 21
Age now: 28

“I was 21 when I [first] had consensual sex. I experienced sexual violence as a teenager and hadn’t done much beyond kissing. I was also in the early phases of figuring out I was queer.

"A good friend asked if I wanted to be in a threesome with him and his girlfriend. I was attracted to both of them, and I trusted them.

"On the scheduled night [at her apartment], I remember brushing my teeth, staring at my reflection, and thinking, this is it.

"The sex...hurt. I was turned on...but I wasn’t used to penetration. But, they were gentle and kind and wonderful. I didn’t come — it took many...years [before that happened]. Afterward, I went home and laid down with this big grin on my face.”
7 of 25
Jill
Age then: 19
Age now: 38

“Our last night on spring break in Jamaica, [my guy friend and I] stayed out really late. I was [secretly in love with him], and I made sure we got completely wasted. I was stroking his chest and he quietly said: ‘Would you like to ride me?’

"[The sex] lasted 20 seconds. Afterward, he ran to the bathroom, then immediately fell asleep — no cuddling. The next day, he barely spoke to me, but after freshmen year we actually toured Europe together and dated for several years. I still consider him my first love.”
8 of 25
“Alicia”
Age then: 16
Age now: 38

“It was with my boyfriend, in his bed, at his parents’ house. It was maybe the fourth or fifth time we had tried, because it was so physically painful, and my anxiety was high.

"I remember it as the most painful thing I’ve experienced. My boyfriend was very patient. There was a ton of blood, and a ton of tears (mine), due to the bodily trauma and a confusing set of emotions: fear, a feeling of sadness that I’d taken a step further away from my youth, and a new closeness with my boyfriend.”
9 of 25
Giulia
Age then: 19
Age now: 30

"The manager of a local band I loved [had told a friend he] thought I was cute. We ended up making out on the streets of the East Village. He hailed a cab and...was like, ‘It's now or never if you want to come home with me.’

"When we got to his place, he tried to go down on me, but I felt uncomfortable. Then, he tried to go for full-on penetration and only made it about halfway in. He told me I was ‘too tight’ and then [masturbated] on me. I...was like, OK, I guess I'm officially no longer a virgin! Yay! But...UGH.

"He wanted to pay for a cab for me but didn't have any cash, so he took a jar full of COINS and told me to take what I needed.”
10 of 25
Katie
Age then: 28
Age now: 37

“[The first woman I had sex with] was a coworker-crush in San Francisco. She had been in charge of bachelor-party festivities for her friend and [later on] had the limo pick me up from the party where I’d been. After holding hands and giving each other achingly wanting glances, she bit my shoulder. I felt as though I would burst into flames.

"We got back to her house and kissed, and...there was a moment when she leaned down and rubbed her naked chest against mine, and all I kept thinking was, This is what people are talking about when they talk about sex being great.

"The next morning...she was affectionate and I was aloof, not because I regretted it or was freaked out over the looming realization of my homosexuality, but because I was falling so hard.”
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11 of 25
Sharon
Age then: 18
Age now: 39

“In [my friend’s] basement after school, we were making out, and then...all of a sudden, he was inside me. I didn't say no, and it wasn’t painful... But, I felt a lot of shame afterward that I had...just ‘let [this guy] do it’ on, like, our third date.

"About a week later, he broke up with me, [saying] we were better as friends. I didn't sleep with anyone [again] for three years.

"It wasn't until recently, when I started to really understand consent and emotional manipulation, that I felt safe saying that I was raped.”
12 of 25
Jen
Age then: 20
Age now: 34

“I had been waiting, even though I had a serious boyfriend in high school, because I never felt like I was mature enough to handle [sex]. But, I was tired of thinking about it. When I [finally felt ready], I was in Austin for a summer internship.

"A few nights before I left Austin, I decided that it was going to be a waiter who had been flirting with me all summer. I don't even remember [the guy’s] name. I picked him because I knew I wouldn’t get emotionally attached — it didn't have this significant weight.

"We went back to his place, drank some beers by his pool, and boned on the couch. I don't remember it feeling great, but I don't remember it being awful. It sort of felt like nothing.”
13 of 25
Mel
Age then: 18
Age now: 38

“It was in my dorm room, my freshman year of college. I did it with my one-year-younger, high-school skater boyfriend who also had his V-card. We’d been dating about 10 months.

"It was over in about two minutes. I was expecting as much, since I’d seen so many teen comedies at that point. I wanted to be all cool about it, so I said, ‘Don't worry, we'll try again later.’

"His eyes filled with tears, and he cried, ‘HOW COULD YOU SAY THAT TO ME?’ I guess he was offended at the implication that it wasn’t amazing.”
14 of 25
Nina
Age then: 15
Age now: Doesn’t want to reveal

“I’d wanted to have sex since I was 13, but the 19-year-old I was nuts about, Mark, wouldn’t [do it then], even though he said I was ‘tempting.’ Two years later, we did it on the living room floor. I ended up [staying] with him for a year, and he taught me a lot. It was a happy ending.”
15 of 25
Jodie
Age then: 19
Age now: 25

“He was a charming Aussie that I worked with at a ski [resort]. He had a roommate, so we [locked] ourselves in the shower. We used a red condom and the color leeched everywhere — I was terrified that I had bled too much. [The sex] was really hot — he picked me up and pushed me against the wall. I was into it. He had no idea he was the first guy [I’d been] with. I'm so glad [I was able to] be uninhibited and have the kind of sex I wanted to have.”
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16 of 25
“Christy”
Age then: 27
Age now: 28

“I lost my virginity last year, at 27. I’d...spent my adolescence as a born-again Christian. By the time I got to college and [realized] that maybe Jesus wasn’t alright with me, I felt light-years behind my peers. But I...wasn’t in a rush to [have sex].

"I met a friend-of-a-friend who was visiting from out of town. We spent a weekend making out. He didn’t make me feel stupid for asking, ‘So, uh, what do I do with my hand?’ while we were fooling around.

"When I went to visit him later, I realized I felt just as comfortable around him with my clothes off, and thought, why not?"

The next day ... I told him it had sounded squishier than I’d anticipated.”
17 of 25
“Rachel”
Age then: 21
Age now: 36

“I hadn't had a ton of physical experience, and I decided early on that I didn't want to have sex until I was in a situation that would mean something. Then, during my junior year abroad in Edinburgh, Scotland, I met a sexy 21-year-old French guy, and we quickly became a couple.

"One afternoon, as we were making out, he pulled out a condom. I told him I had never done it before. He...said he would wait until I was ready, then he gave me the condom so I could pull it out whenever I felt it was time.

"It [happened] in my room in my apartment, and it was somewhat painful, but also enjoyable. He was very attentive and gentle.”
18 of 25
Nancy
Age then: 20
Age now: 50

“When my boyfriend of eight months and I were ready to be intimate for the first time, he [took me to] a sleazy motel, complete with red lights and beer cans discarded in the parking lot. His first words afterward? ‘We shouldn't have done this.’”
19 of 25
Elisabeth
Age then: 17
Age now: 39

“We did not ‘date.’ [The guy I liked] simply came over one night when my parents were attending family therapy, [which] was a mandatory part of the outpatient rehab I was being forced to do. It wasn't good sex. It wasn't painful, but it wasn't enjoyable. I felt relief that I was no longer a virgin, but I do regret becoming involved with that boy, because he turned out to be a complete asshole. I did get very attached to him after the sex, but I don't know if it was because it was my first time or just [because I was] so hungry for attention.”
20 of 25
“Danielle”
Age then: 21
Age now: 28

“I was flipping through TV channels when I landed on a pop culture game show. I sent [a contestant] a MySpace message saying that I thought he was funny. For almost a year, we had a long-distance courtship filled with snail-mailed mix CDs, Valentine’s Day cards, and phone calls. There were even sexts, except there wasn’t a word for them yet (my roommate and I just called them “sex texts”).

"He was...surprised when I told him I was a virgin. I felt woefully inexperienced for [my age]. He was 27. When he came to visit and we had sex, it was really short and really painful.”
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21 of 25
Alison
Age then: 18
Age now: 29

“I was in the dorm room of my first-ever boyfriend. Sock on the door, lofted bed, The Doors on vinyl. It didn't actually...work...the first time. He was a big guy; I'd never even used tampons and hadn't really spent much time with myself down there. It was like trying to push a boxing glove through a button hole.

"We finally got things working on our third try.”
22 of 25
“Kyra”
Age then: 24
Age now: 38

“I went to the African island of Madagascar as a Peace Corps volunteer. I lived in a tiny, rural village (no electricity, no running water). The city was my escape from village life. I would hang out with a group of young, hot women at this tiny basement dance club.

"There was one woman, Annika, who I...became friends [with], and eventually she started spending time in my village. It was fun having her around...and she was one of the most beautiful women I had ever seen. After about a year, [we had sex]. [Our relationship had] evolved. She represented everything to me...and the way to elevate it was to share my body with her.

"I [didn’t] think of myself as a lesbian at the time, [though] I am pretty sure I am now. I do not think Annika [was] gay. She had such an impact on who I am and how I love.”
23 of 25
“Beth”
Age then: 17
Age now: 30

“It was the summer before college, and I’d been dating a friend of a friend for four or five months. I liked him, but didn’t love him, and looking back, I think I was mainly using him for sexual experience; I’d gotten pretty much zero action throughout high school.

"I went over to his parents’ house one night when they were out, and we drank some of their wine, ate some food, and then went out on the big wooden deck. It was almost summer, so it was warm and there were crickets chirping. I knew we were going to do it.

"We started fooling around, lying on the floor of the deck, which wasn’t exactly comfortable. When we tried to [have sex], it hurt too much. I had to stop him. We tried again, and it was okay that time. I didn’t bleed, but I didn’t really [enjoy it], either.”
24 of 25
“Mary”
Age then: 16
Age now: 31

“Dave and I met at a sports camp. He was my first kiss. We didn’t live [in the same state], but we stayed in touch [after camp]. Later, when I learned he would be visiting [nearby], we made a plan to lose our virginities to each other. I wanted to [do it with him] because I felt like we were on the same page about our feelings and expectations.

"[At] his hotel, we stayed in the room for five hours having sex, napping, watching My Cousin Vinny, and being nervous and awkward. We had sex seven times that day, but only a couple to completion (his completion, never mine).

"It wasn't a physically pleasant experience, overall. I bled. But it wasn't terrible, either. If anything felt wrong, we just stopped and watched TV. We never saw each other again, but...I still think of it, and him, really positively.”
25 of 25
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