My first fucking

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I've grown so much more comfortable with sex, and I can thank my boyfriend for that for being kind and gentle. But the conversation was always about boys, never about being sexual with girls , so I felt completely unprepared when I went to have sex with my girlfriend for the first time.

It was the summer after I graduated from high school and I was on a date with this kid I knew since elementary school.

We had talked about it before and we got this cheap motel and we did it. I felt kinda numb until the next morning, when I got in the shower and cried for an hour.

It wasn't a big deal in my mind, as I'd lose it one day anyway, so why not then? I was talking to the boy for awhile and he made me feel like it was the right thing to do.

I imagined it'd be like in the movies — all sweet and romantic, all planned out. It wasn't! It was awkward and I didn't really know what to do.

Since then, my experiences have gotten better as I now know what I'm doing. We always joked about marriage, and he was cute, but I never felt attracted to him.

One day, we went hiking, and he kissed me at the top of the peak, and I felt excited. He was older, his arms were strong, and he wasn't aggressive like the boys I kissed in my grade.

He was my best friend and we were kissing — what!!! Anyway, that summer, we talked about having sex, but he insisted that I had to be Finally, my birthday came, and his family was home, so we snuck into his backyard and went into a children's playhouse adorned with little kitchenware and dolls.

So not sexy. It was awkward and it didn't really work. He blamed me for it. It was really immature. Also, after having sex with guys, I've realized that sex with girls is more my speed — more fun.

I had always been nervous about the idea of sex. I had so many questions about how it would feel. But we discussed it and we both agreed we trusted each other fully.

At first, it felt weird — not painful, but just a completely different feeling. My advice is to make sure you trust this person so you can enjoy it even if it is awkward at first.

I had met this guy online when I was younger and we had been talking for awhile. I had gone to see him a couple times and he said he didn't want to be my first.

But then on New Year's Eve, he invited me over and we ended up having sex. I felt super weird after, because I was like, maybe I should've waited for someone I loved.

I really think that shapes how I treat sex now. I know a lot of people whose first time was with someone they loved, and now sex is this sacred thing for them — whereas for me, sex is really just an act of pleasure.

My boyfriend was visiting and it felt right at the time. But then he had to leave to go back to school, and I was left with a lot of emotions, including regret and shame.

I missed him and I felt overwhelmed. Even though we aren't dating anymore, I really did love him and a part of me always will.

My boyfriend at the time and I had been together for about eight months and things were getting serious, so we decided to do it. I was expecting it to be so nice and amazing, but instead it was so painful.

It only lasted a couple of seconds. We had sex in a car how romantic, right? I was so nervous that he wouldn't feel that 'spark,' but he did.

At the time, I felt amazing. I thought I found the guy of my dreams and that we'd get married. We're no longer together, but I don't regret the experience.

I just wished I had known I didn't need to have sex with a guy for him to approve of me or continue dating me.

I'm on the Pill and we used condoms. It didn't hurt at all. I was so happy to be making love with him. I liked the feeling of being so close to him.

But physically I thought it felt weird — like it didn't really feel all that great and I didn't feel tons of pleasure. Afterwards, I expected to feel more mature and more confident, but I really just felt the same as I always have.

I don't really feel like losing your virginity is as big of a deal as everyone makes it out to be. I'm happy that I had my first time with someone I love , so, in that aspect, losing my virginity was really great because of how much I love my boyfriend.

If it had been with anyone other than my boyfriend it would have been sooo embarrassing. One friend asked if he could crash at my place.

I wasn't expecting it to turn into anything — I didn't even know he felt attracted to me that way. It was very spur of the moment, but we did use a condom.

He was my good friend and I trusted him, so even though we didn't talk about it beforehand, it felt right and okay and was even pretty exciting. I was obsessed with the fact that I was a virgin, sizing up my classmates, puzzling over whether any of them were virgins, too.

One of my high school crushes invited me to hang out one weekend, and according to my experienced roommate, it was apparent that he wanted to have sex.

We used protection. He was considerate and gentle and quite kind. The experience as a whole was very positive. I didn't have sex again for another two and a half years.

I was ready and glad to no longer be a virgin, but I was not ready for the risk and responsibility of being sexually active. I have no regrets — either about how I lost my virginity or how long it took me to have sex again, because both were a reflection of me being good and ready.

We decided to do it after about three months of dating, when I knew for sure I was ready. We used a condom. Honestly, I didn't feel different after than I did before.

Maybe just a little more mature. If you really think you're ready, and you and your partner protect yourselves, it can be a really cool thing.

I decided that I wanted to wait until college to lose it, but when I finally got to college, I didn't really meet anyone that I wanted to have sex with, especially not for my first time.

I ultimately decided to lose it to a guy that I really, really liked but wasn't in a relationship with. I was just so ready to 'get it over with,' and this guy was and still is a great guy.

My one regret in the entire experience is that I didn't tell him that I was a virgin. To this day he doesn't know! I was so scared that I was going to freak him out, but really, a lot of awkwardness could have been avoided if I'd just been honest.

I was 17 and I just wanted to get it over with. I asked one of the people that knew me best at the time, my sort-of boyfriend, if he would take my virginity, and he agreed.

We used condoms. At first, we couldn't find the hole, but eventually, we did. Afterwards, I didn't feel much different. He was two years older than me and not a virgin, and he had been trying to persuade me for a couple months beforehand.

When we finally did have sex, it was when I was ready. I was glad that I didn't give in until I was really ready.

It was painful and slightly awkward. I had this weird feeling of elation once it was over, though, because I had always wondered what it would be like, and it had finally happened.

I've never had any real regrets about the person I experienced it with or how it went down. Although I will say it would have been better in a bed and not in the passenger seat of a Honda Civic There wasn't one specific moment when it happened.

It was more of a progression from one stage to the next rather than 'here's the moment I lost my virginity' because we're both girls.

I was excited and nervous and happy about the whole thing. We were both virgins and just wanted to get it over with. It wasn't pleasurable or even fun, and throughout the entire process all I could think about was, when will this be over?

Moral of the story — wait until you're really ready. It was during my freshman year of college with an upperclassman frat bro.

We'd been talking for months and I was convinced he liked me, though looking back on it now, his texts of 'What are you doing tonight?

At all. What stung the most was what happened after. He didn't text me at all and when I saw him at a party the next weekend he completely avoided me.

If I walked into a room and we made eye contact he would immediately turn and walk out. It felt like a huge slap in the face. I liked him, but he had finally gotten what he wanted and that was it.

He was over me. I wanted nothing more than to go up to him and yell and ask him why he was being so mean to me when I had done nothing wrong, but every weekend he would completely avoid me or be talking with another girl when I walked by.

I knew I wanted to sleep with him. I thought about it for about a week to be sure, but I knew I was ready. I brought it up first, but quickly added that if he didn't want to yet, we could wait.

He immediately said he wanted to, but asked about five times if I was sure I was ready, making sure I knew that he wouldn't care if I changed my mind.

He made me feel safe, he made me happy, and that made me even more sure than before that I wanted to sleep with him.

It was with a guy friend that I spent a lot of time with and did physical things with, but we weren't technically in a relationship. However, we were really good friends and I felt comfortable with him.

Sex had been in the back of my mind for a while. I asked him about one month in advance if he wanted to do it with me, and he said yes.

He had never had sex before, either. We used a condom, which he more than willingly agreed to do. Before we did it, I felt extremely nervous, but a good kind of nervous — it was something I really wanted to do, I just didn't want to mess it up.

Afterward, I honestly felt closer to him emotionally and physically, and I could tell he did too. Our relationship ended up becoming more serious and eventually we started dating for real.

The guy I lost it to was my first love. When we finally tried to have sex, it hurt unusually badly. We kept trying the whole night, but it just wasn't happening.

Then I cried and stared out the window it was raining for an hour. Jesus wept. That was the night conservative right wing Buggie started to die.

Location: King suite of a fancy hotel in downtown Baltimore. How it went down: It was our wedding night, and despite having done damn near everything else, we had agreed to save the coitus, the final frontier, until we were married.

We're Orthodox Jews, and hey, this was how we justified the everything else. He wasn't a virgin, having gotten religion in college after having his share of partners.

I was, technically. After the wedding, still in our dress and suit respectively , we drove over to the fancy hotel my parents graciously paid for which is kind of weird in retrospect.

I told him I had to "slip into something more comfortable", then went into the bathroom and got into a pair of fuzzy pink footy pajamas.

I came out and did a striptease to "Natural Woman". I simply couldn't take this whole "deflowering" thing seriously. We commenced the consummation, in the bed and in the bathtub.

I remember being underwhelmed, but knowing we would get better with practice. I didn't bleed, and it didn't hurt. I didn't come until we resorted to our usual fingerbanging - the clit wants what it wants, what can I say.

Then we snuggled and watched Family Guy which totally was still funny and not lame back in , and ate leftover wedding food. It was perfect.

Partner: A guy from the periphery of our friendship group. How it went down: I was very drunk and it happened while we were watching Castle , so I stared into Nathan Fillion's eyes on the screen over his shoulder while he got off and I wondered if all sex was really this boring.

How it went down: Backstory - I'm a nerd, and was a bit of a chubster in high school, so I didn't date. After I graduated, I stopped talking to everyone but my best friend from school, got hired by the USDA after a successful apprenticeship, and went to community college.

I had a bit of a breakdown from lack of social interaction, and over the course of a year dropped out of college, did a fair amount of drugs mostly pot , lost 60 lbs, became a vegetarian, quit my science job and started working at the local co-op.

I met my first boyfriend at our weekly Dungeons and Dragons session. We'd been dating for all of two weeks, and had several awkward fumblings where he couldn't stay hard for the condom and would roll over to sulk, and I was getting fed up.

He was a virgin too, but he wasn't the only frustrated party in the bed, and I was trying to be supportive but he was having no part of it.

I was at the end of my rope, and called my friend to go hang out and bitch. I still lived at home, but she was married and lived with her husband and two kids, so I'd stay at their place frequently.

When I got over there, I was greeted with a large bottle of Boone's farm and a bong hit just for me. I griped it out, got ripped, and we started talking about solving my problem.

She and her husband had made it quite clear before that he was available if I was interested, and I'd engaged in kisses and fumbling with him but nothing more.

We had an unusual friendship, to say the least. At this point, I was super frustrated, and the alcohol was changing my attitude on the matter from "Isn't this odd?

Her husband came home from work to find a plan hatched and two tipsy girls with devious grins. He was game, so we took the party to the bedroom.

Even fortified with liquid courage, I was nervous, but I really really wanted to fuck. There was some kissing between the three of us while clothes came off.

I remember sitting on his face kissing her while she rode him for a little bit I didn't want to go first because I'm a dork. I was on my back when he entered me for the first time.

He was big, but it didn't hurt because I'd been masturbating for years. Honestly, it was a bit underwhelming at first. It totally got better though, and we went through a few positions until I ended up on top of him.

I didn't come, but I got pretty damned close. The next day I broke up with my boyfriend. I didn't tell him what had happened the night before.

I never slept with my friend or her husband again, and we drifted apart eventually. It was nearly a year before I had sex again.

My second boyfriend was awesome, and we fucked like nerdy rabbits. I wouldn't change a thing, except maybe dumping the first boyfriend sooner.

He was a tool. How it went down: I attended a small liberal arts college in the south, and I ended up pledging a fraternity my freshman year.

He was the president of that fraternity and three years older than me. Once a year the chapter would have this long, drawn out ritual that ended with the incoming pledges being assigned a "big brother," an upperclassman in the fraternity who would take the younger pledge under his wing.

After the ceremony it was tradition for the big brothers to take their "little brother" back to the fraternity house to drink and whatnot.

At one point in the night, we ended up going to his room to get some ice, which somehow turned into a slightly drunken awkward kiss that transitioned into slightly drunken awkward man-on-man action.

Now she's my wife. I didn't discover this till later, but she's three years older than me. How it went down: She joined the company about a year after I did, I was in and out of the office a lot, because my job was mobile, so I'd stop and chat with her whenever I went by.

She was fucking gorgeous, huge tits and whip-smart and funny. Me, being at the time, a fat, bespectacled nerd with a serious self-confidence problem, immediately thought "She's too good for me" and masturbated furiously to her image from afar but never made any moves on her for months.

But we talked, laughed and, when my job gave me long breaks, I would keep her company while she wrangled the phones. Conversations soon led us to discover that we had the same career plans we both wanted to be cops and just when I had barely wrangled up the gusto to ask "maybe we should train together some time?

The run was scheduled for friday night, at the university campus next to her house. I got lost. Like, really lost. We were supposed to meet at 9pm we both got off work late and I didn't get there till closer to She was good-natured about it, and off we went, running around the track at the university.

At this point, I really didn't notice that her eyes were pretty much boring a hole into the crotch of my running shorts. And I really didn't pick up on the three times, she got super close to me and asked me whether I'd had any girlfriends no , or had anybody kissed me no or whether I had anyone I had a crush on at the office her, but I wasn't going to admit that straight out, so no.

To say I was an oblivious sap would be an understatement. After the run, she brought be back to her place, which was really a basement room she was renting, and fed me pie pumpkin, this was Thanksgiving weekend , and basically, now that I have the benefit of hindsight , chatted me up for two hours straight, inching closer and closer to me as the minutes passed she had started out on the opposite couch, but then by the time things came to a head, she was sitting at my feet with her head in my lap.

It wasn't until this point that I realized what she was after, and to say I had no idea what to do would be an understatement. I remember staring awkwardly away, trying not to burn holes in her cleavage, making vague "I'm not sure about this Thankfully, I was in the hands of somebody on a mission, who was not even going to let the vague discomforted of a horny, unsophisticated year-old virgin stand in her way.

I later found out that this mission was due to the fact that she and the other receptionists had been speculating on the size of my penis for months.

This is when I discovered, low and behold, I was good at touching. Watch lesbian porn, everyone, they are good teachers.

Either way, she initiated everything, from pulling my clothes off to climbing on top of me. I was too lost in a state of delighted misbelief to do anything useful.

I seriously thought I was dreaming. Up until, mid-act, my brother calls - and me, making dumb virgin moves - actually picked up. Hot beautiful girl raises eyebrows.

I drove home shortly after, wondering if she had slipped something into my pie. How it went down: For the longest time I couldn't figure out how to use a tampon so I went to the school nurse and had her show me how.

Then I got overzealous and decided to start using a Diva cup. My boyfriend was hanging out with me while I was trying to work it in.

I couldn't get it in and was frustrated and on the verge of tears when I decided to have him help me stretch out.

It was completely unromantic but he was totally into it and then neither of us orgasmed because I didn't need us to orgasm in order to get the Diva cup in.

Poor guy. Things got better later of course. Location: Air. I couldn't afford anything else and was already in a shitty apartment in a shitty neighborhood after being told I could not stay with my parents for a summer between college semesters.

The room was incredibly tiny. It was also in a hot city in the South in the dead of summer, and we did not have air conditioning.

All of this will play into the saga. How it went down: He was my boyfriend I'm a girl , and also a virgin. Having sex on an air bed is at best a calculated risk, and at worst a complete and utter shitshow.

This was the latter. Both of us were virgins, and he got a little Because of the previously mentioned heat, we were both gruesomely sweaty this will come into play later.

We struggled a little bit with the condom and subsequent insertion, as novices are wont to do, and he started going to town. He must have thought that the more athletic the thrust and the wider its range of motion, the better the sex.

So the air bed was rockin and rollin, when suddenly he thought it was a good idea to try to put his hands under me during a particularly hearty thrust.

We lost our balance a bit and shifted to the edge of the bed, which as any experienced air bed user will know, caused it to tip over completely, ejecting us from the bed.

I heard his cries of anguish and stood to help him, but because his body had tracked sweat across the floor, I slipped, fell back on top of the air bed, and popped it completely.

It didn't hurt for me at all, and we went on to have a pretty fulfilling sexual experience together. At his place. On a real bed. Anyway, I love trotting out this story when sharing worst experiences with sex.

Age: I was 16, he was 17, and I felt like a goddamn badass. Location: Rural Pennsyltucky, against the upstairs wall on his divorced mother's condo's hallway, and because she wasn't really a person, it was lined with white shag carpet, and why this matters will soon be clear.

How it went down: I was an emerging poet who loved and dated a boy for over a year just because he was the lead singer in a band and this is what's more important wrote the lyrics to all their songs.

His mom—a local public high school English teacher who wanted desperately to be a writer, and with whom I hoped to connect so sweetly with that we'd go see Charles Dickens' plays together at Christmas, both of us wrapped up in scarves she'd knitted, or else we'd take bus trips to New York City just to smell the public libraries—hated me.

Luckily, she hated Pennsylvania more, but before leaving for a week-long vacation in the Florida Keys with her overweight Match. To this day, I've never been able to find these condoms in a store again, which means that obviously way back in , his mother must've ordered them specially from an online porn shop, which is great fun to think about!

Chris and I were, as you might well guess, completely disgusted and freaked out, but we were also seventeen, so after striping one another bare, we began to have sex the only way we knew how: the way they do it in porn, with my back pushed against a wall, my legs wrapped around his waist, and Chris thrusting anxiously into me with unparalleled awkwardness and noise.

I began to bleed—just a little at first, and "Keep going," he said, "don't worry! We stopped having sex to try and clean the carpet, but the wet paper towel only smeared it and made it worse, and then we decided, Well, fuck it then, and resumed our former position, except now Chris' hands were bloody and wet from all the failed cleaning and we smeared it all over the wall.

I came, which is perhaps what's most surprising here, but we spent the whole rest of the week repainting the hall, scrubbing the carpet with every kind of "sit and wait" foaming cleanser available from our small-town hardware store, and every time I was over, we'd return to the hallway to neurotically examine the spot from different angles and in different light.

We didn't date a whole lot longer—that kinda push the kibosh on sexiness—and his mother has since moved, but I can't help but think about that hallway whenever I visit home.

Snuck out of parents house a week before my 15th birthday. Walked to the party in the surfer-laden suburbs of Lake Forest yep, the OC baby!

Was wearing thin peach top with black bra underneath, and short black 80s skirt that had those 3 ruffles tiered down it. Was blonde.

Was very blonde due to Sun-In. Was tan. Was pretty fucking cute. Was being very brave because I hung out with punks, losers, dorks and retards but I really wanted to lose my virginity to a boy based solely on his looks, since I couldn't find one who was worth my time, and I was fucking horny living among all those pliable sun-bleached-brained boys.

Sauntered around surfer boy party looking for boy to fuck. Wanted sex unbelievably badly would possibly explode upon contact. Girls looked at me knowing that I'd come alone, I didn't like any of them, it wasn't my scene, and I was invading their boy cliques.

Held beer in keg cup and eyed up every last one of them fearlessly, I respected none of them and I walked as if in a force field, eyes roving like the Terminator's.

There were 4 boys that all girls wanted. They were the shining stars of El Toro High School. They were known as the Grommets, like the fish that played in the ocean in the day and fucked on the beach at night.

They were golden.

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I was so happy to be making love with him. I liked the feeling of being so close to him. But physically I thought it felt weird — like it didn't really feel all that great and I didn't feel tons of pleasure.

Afterwards, I expected to feel more mature and more confident, but I really just felt the same as I always have. I don't really feel like losing your virginity is as big of a deal as everyone makes it out to be.

I'm happy that I had my first time with someone I love , so, in that aspect, losing my virginity was really great because of how much I love my boyfriend.

If it had been with anyone other than my boyfriend it would have been sooo embarrassing. One friend asked if he could crash at my place.

I wasn't expecting it to turn into anything — I didn't even know he felt attracted to me that way. It was very spur of the moment, but we did use a condom.

He was my good friend and I trusted him, so even though we didn't talk about it beforehand, it felt right and okay and was even pretty exciting.

I was obsessed with the fact that I was a virgin, sizing up my classmates, puzzling over whether any of them were virgins, too. One of my high school crushes invited me to hang out one weekend, and according to my experienced roommate, it was apparent that he wanted to have sex.

We used protection. He was considerate and gentle and quite kind. The experience as a whole was very positive.

I didn't have sex again for another two and a half years. I was ready and glad to no longer be a virgin, but I was not ready for the risk and responsibility of being sexually active.

I have no regrets — either about how I lost my virginity or how long it took me to have sex again, because both were a reflection of me being good and ready.

We decided to do it after about three months of dating, when I knew for sure I was ready. We used a condom. Honestly, I didn't feel different after than I did before.

Maybe just a little more mature. If you really think you're ready, and you and your partner protect yourselves, it can be a really cool thing.

I decided that I wanted to wait until college to lose it, but when I finally got to college, I didn't really meet anyone that I wanted to have sex with, especially not for my first time.

I ultimately decided to lose it to a guy that I really, really liked but wasn't in a relationship with. I was just so ready to 'get it over with,' and this guy was and still is a great guy.

My one regret in the entire experience is that I didn't tell him that I was a virgin. To this day he doesn't know! I was so scared that I was going to freak him out, but really, a lot of awkwardness could have been avoided if I'd just been honest.

I was 17 and I just wanted to get it over with. I asked one of the people that knew me best at the time, my sort-of boyfriend, if he would take my virginity, and he agreed.

We used condoms. At first, we couldn't find the hole, but eventually, we did. Afterwards, I didn't feel much different.

He was two years older than me and not a virgin, and he had been trying to persuade me for a couple months beforehand. When we finally did have sex, it was when I was ready.

I was glad that I didn't give in until I was really ready. It was painful and slightly awkward. I had this weird feeling of elation once it was over, though, because I had always wondered what it would be like, and it had finally happened.

I've never had any real regrets about the person I experienced it with or how it went down. Although I will say it would have been better in a bed and not in the passenger seat of a Honda Civic There wasn't one specific moment when it happened.

It was more of a progression from one stage to the next rather than 'here's the moment I lost my virginity' because we're both girls.

I was excited and nervous and happy about the whole thing. We were both virgins and just wanted to get it over with.

It wasn't pleasurable or even fun, and throughout the entire process all I could think about was, when will this be over? Moral of the story — wait until you're really ready.

It was during my freshman year of college with an upperclassman frat bro. We'd been talking for months and I was convinced he liked me, though looking back on it now, his texts of 'What are you doing tonight?

At all. What stung the most was what happened after. He didn't text me at all and when I saw him at a party the next weekend he completely avoided me.

If I walked into a room and we made eye contact he would immediately turn and walk out. It felt like a huge slap in the face.

I liked him, but he had finally gotten what he wanted and that was it. He was over me. I wanted nothing more than to go up to him and yell and ask him why he was being so mean to me when I had done nothing wrong, but every weekend he would completely avoid me or be talking with another girl when I walked by.

I knew I wanted to sleep with him. I thought about it for about a week to be sure, but I knew I was ready. I brought it up first, but quickly added that if he didn't want to yet, we could wait.

He immediately said he wanted to, but asked about five times if I was sure I was ready, making sure I knew that he wouldn't care if I changed my mind.

He made me feel safe, he made me happy, and that made me even more sure than before that I wanted to sleep with him.

It was with a guy friend that I spent a lot of time with and did physical things with, but we weren't technically in a relationship.

However, we were really good friends and I felt comfortable with him. Sex had been in the back of my mind for a while. I asked him about one month in advance if he wanted to do it with me, and he said yes.

He had never had sex before, either. We used a condom, which he more than willingly agreed to do. Before we did it, I felt extremely nervous, but a good kind of nervous — it was something I really wanted to do, I just didn't want to mess it up.

Afterward, I honestly felt closer to him emotionally and physically, and I could tell he did too. Our relationship ended up becoming more serious and eventually we started dating for real.

The guy I lost it to was my first love. When we finally tried to have sex, it hurt unusually badly. We kept trying the whole night, but it just wasn't happening.

I eventually found out I had cysts on my ovaries. We broke up about five months later. Afterwards, I thought I had wasted that special moment on someone who didn't deserve it.

But now, I'm grateful because that experience probably saved my life. We are on good terms now, so I'm glad to say it wasn't a mistake.

It happened during a Netflix and chill situation and things were escalating pretty quickly. The guy I had been talking to didn't know I was a virgin, and I didn't tell him because I was afraid it would scare him off.

Losing my virginity was quick and for the most part painless. It was no worse than period cramps. Once I got home, I felt guilty because it wasn't how I imagined losing my virginity , and not something you get back.

I cried for a little bit and then decided there wasn't anything more I could do about it. I couldn't change what had already happened.

All in all it wasn't terrible, and I'm not sure I would change it. I had wanted to wait until we had reached the six-month mark of our relationship, but it was about four and a half months into our relationship.

It was on my bed in my dorm on a Sunday which I remember because his dad is a pastor! I had no pain, and it just felt right. He was gentle and it was loving.

I knew I was ready because I just looked at him and wanted to be with him. The fact that he hadn't pressured me before helped, too.

I remember whispering that I was ready, and he asked me twice before we actually did it if I was sure. We spent time after just cuddling and I felt so happy.

Before then, I hadn't gone very far past first base. I don't necessarily know if I felt ready or if I just felt like it was about time I got this over with, but I was doing everything I could to find the right guy.

After many, many failed dates, I met my first boyfriend at a film festival. He was cute, European, and really into me. Within a week, he was asking me to be his girlfriend.

I didn't know how I felt about him, so I kept putting off becoming official. One day, we were fooling around and he asked to put on a condom.

I was definitely into it, so I said, 'OK, I want to be your girlfriend now. Put on the condom. I had just started the Pill and I was really afraid of getting pregnant and 'ruining my life,' which was the message I'd received growing up.

I put a towel down. I wasn't afraid of what it would feel like; mostly I was just afraid I wouldn't be good at it. Despite his efforts to the contrary, it hurt a lot.

I just pushed through, thinking that eventually it would get better. The problem was, it never got better. Three years went by and sex still hurt.

Several doctors later, I learned the culprit was a condition called endometriosis. With endo, the lining of your uterus grows in places it shouldn't, like your fallopian tubes, ovaries and sometimes elsewhere in your body.

There's no cure for endo and treatments are limited, but there are more ways to enjoy sex than just intercourse alone.

We made out after an orientation party, then kept in touch through thousands of flirty texts all summer long.

When we finally got to college, we spent hours hooking up every day. I kept hoping he'd take me out on a date — I wanted him to be my boyfriend — but that never happened.

After three weeks of him pressuring me to have sex, I finally felt ready. Thirty seconds after it was over, he got up, got dressed, and left.

He ignored my texts, never spoke to me again, and avoided eye contact every time we ran into each other for the next four years.

I was furious at him for being such a jerk, but at least I knew that any sexual encounter I had after that would be lightyears better by comparison.

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