The Complicated Story of How I Lost My Virginity



What’s your gender? Woman
How old are you? 21
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

The Complicated Story of How I Lost My Virginity

How long ago did this hookup happen? 2 months

What was your relationship status at the time? Single

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

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I have know David, the man I lost my virginity to, since I was 8. I grew up in a very small town, and his family and my family have always been intertwined in some way. David is 4 years older than me and has 2 younger siblings: Sarah, my age; and John, 1 year younger than me. I went to the same elementary, middle, and high schools as all of them. Sarah and I were close friends when we were younger, and only grew apart in high school. David has been my older brother, Paul’s, best friend as long as they have known each other, and they are still going strong. We have all moved away for college or work now, however, and see each other less often as a result. Until last summer that is. I came home from college for the summer, and ended up working for their mom, Linda, and started hanging out with their entire family again (the siblings were home intermittently for the summer as well). During this time, I began hanging out with John, the younger brother, and actually developed a fairly strong crush on him. He had a long-distance girlfriend, however, so of course I never acted on it or let him know how I felt. I saw David every once in awhile as well. He lives in a city a couple hundred miles away with his girlfriend, and would come to visit on the occasional weekend. He has been with his girlfriend at least 3 years, she is a couple years his senior (late 20s), and I know has been pushing for marriage, while David has been reluctant on that front.

This long preamble is all simply to get across the fact that I have long and somewhat-significant relationships with everyone in that family. However, my relationship with David had historically never been anything but platonic. He was/is my older brother’s best friend! To me, he was the guy who teased me and made me cry when I was little; I didn’t know him on any real level, especially since we had all grown into adults. What I knew of him was that my brother loved him, so of course he is a great guy. Besides that, David is very tall, dark, rather handsome in a slightly goofy way, has a great sense of humor, and exudes confidence. All attractive qualities to me, but I just never looked at him in that light, especially considering his girlfriend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Over winter break, just a of couple months ago now, David’s family invited my family and one other family over for a party on Christmas. Now, their family is known for throwing the best parties, always with a ton of food, beer, and laughter. My family was all very excited. I had since gotten over my crush on John, and was nursing a recent rejection wound. Fall semester I had developed feelings for a male friend, got up the nerve to tell him how I felt, and was politely and kindly rejected. It hurt a lot though, and am still struggling with it, though we are better friends than ever. That was the first (and only) time I have ever told a guy I liked him, and I am so proud that I did it, that I allowed myself to be so vulnerable. But being rejected left me back at square one. I have always been shy and hard to get to know. And I think this has contributed to my lack of experience. The farthest I had gotten with a guy was holding hands. And this is at 21 years old. Needless to say, I am a late bloomer. I wish that I was able to own it, to be fine with my lack of experience, but it has been a source of insecurity for several years now. I felt I was ready for a relationship, be it serious or casual, but I didn’t know how to find one.

Anyway, back to the Christmas party. We had a delicious dinner around 5 o’clock, followed by a few rounds of a drinking game for the younger folk. By this point I had probably had 2 drinks, and was just starting to feel buzzed. We then decided to take the party down to a cabin they built a few hundred yards from the house. While the parents talked, all us 20-somethings played King’s Cup (a fun, interactive drinking game). There was lots of dancing, laughing, and homemade moonshine involved. I ended up drinking more than I planned, and things begin to get fuzzy from this point on. People began trickling off, returning to the house one by one. Eventually only myself, David, John, Linda (their mom), and one other woman were left, all gathered around the campfire, still drinking beer. I remember David calling his girlfriend on speaker phone to check in. She told him she loved him; he said it back. Then Linda and the other woman decided to go back up to the house. Linda jokingly asked me if I felt safe being left alone with her 2 boys. Because of course nothing would happen between us! How absurd! And the idea did seem absurd, and still seems absurd to me.

This all being quite fuzzy, I don’t remember when John left, but at some point David and I started talking about relationships. It was really just him asking me questions. At the time, it felt slightly odd- mostly because I had never had a really conversation like this with David before, where we were seeing each other as people instead of as my big brother’s best friend. He asked me if I had a boyfriend, and I told him no, and about the friend who had turned me down at college. He asked me about past relationships, and I think I was just so insecure and embarrassed about my inexperience that I didn’t want to share that with him. So I made up some bogus story about how I had hooked up a couple times in college, but they weren’t great experiences. I wish I hadn’t lied to him, but I had no idea at this point that something sexual would happen between us, otherwise I would have wanted him to know the truth. I remember him telling me how guys my age often make stupid decisions, how he commiserated with my fake bad experiences with men. He asked if I had ever orgasmed, and I said no. He said the female orgasm is “very important” and recommended getting a vibrator. If I had not been totally hammered this all would have been so bizarre, but as it was, I didn’t find it weird at all. On the contrary, I found it refreshing to hear from an older, male brother-like figure about stuff I am clueless about.

I know at some point during or after this conversation John left, and David and I were alone down at the cabin. We tried to go on a hike, but the snow was so deep and we were so drunk that we failed miserably after walking probably 50 feet. So we headed back to the cabin, came inside, and hung up our coats.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The next thing I remember is being kissed. It’s like I just woke up in the middle of it, totally disoriented. I knew where I was, but looking back, I don’t remember how it was initiated, if I was sitting or standing, nothing. I remember being confused about who I was kissing, thinking it was John at first (the manifestation of the remnants of my old crush I suppose), almost saying John’s name, and then thinking, “Oh! No, this must be David.” I immediately thought of David’s girlfriend, remember saying that we should stop kissing several times, asking him “What about [his girlfriend]?” and him not responding. I felt so bad about the cheating, but being as drunk as I was, I didn’t know how to make it stop. And it felt good. I was into it. It was new and exciting. And pretty soon, his girlfriend just slipped my mind. I remember being on a reclining chair, the only semi-comfortable place in the cabin, with David on top, making out. I loved the feeling of his scruff against my hand when holding his face. He began rubbing against me. At some point, he stripped off my tights, and it was only then, in my drunken, inexperienced state, that I realized that the grinding had not actually been sex. He went down on me, but I was too drunk and self-conscious to enjoy it. Eventually he stopped, to my relief. He kissed me again, and I felt slightly odd tasting myself on his lips. I was nervous he would ask me to go down on him, and I had no idea how to do that, was slightly nervous about handling a penis, and was hence very relieved when he didn’t. I guided his penis into me, (it was much softer than I imagined!), and it was slightly painful, an uncomfortable stretching. He was very slow and caring, checking in with me often. I don’t know why, maybe because he was drunk, or maybe it was my fault, but he slipped out every once in awhile, which was too bad as it disrupted the rhythm of things. After maybe 10 minutes he asked me to try being on top. I told him yes, but that I had no idea what I was doing, but he was reassuring. He said I looked great up there, which made me feel much more confident. I liked being on top, but doing it on a recliner made getting into a position that worked rather difficult. It was also way more tiring than I expected. After a little while we switched again. He was so tall that, whenever I wanted to kiss him, I would have to crane my neck way up to reach his mouth. He moved his hands up and down my body, feeling my legs, butt, and back. At one point near the end, we finally got into a good rhythm, and he began breathing heavy, increasing my arousal in turn. I thought he was going to cum, but then he slipped out again. At this point we were both getting cold in that poorly insulated cabin, so decided to call it quits. The sex, though not the most successful physically, was fun throughout. He was so communicative, and we laughed when awkward things happened. It just felt like an intimate, fun, new experience to share with someone.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We ended up falling asleep for a few hours, cuddling, and then walked back to the house in the very early morning. I was still drunk at this point, and not cognizant of the implications of what we had done, but I think it was beginning to dawn on him. He was frazzled when collecting his clothes, and nearly silent on the short walk back to the house. We fell asleep on the floor of the living room where everyone else was crashing. The next morning, I felt so horribly. I tried not to act weird or avoid eye contact with him, but it was so obvious what a terrible thing we had done. Everyone knew we had come back late together, and asked what we were doing there alone for so long. We made up some excuse, and no one suspected anything. My brother even made a joke that we were doing the nasty, again because that was such an absurd thought. David had to drive back to his home that day, so we didn’t get a chance to see each other in private. I was freaking out inside. I hated that I had been party to cheating, and I was basically having an identity crisis: I thought I was a good person, but now how could I say that? This was worse than anything I had ever done or suspected that I would ever do. On top of that, we hadn’t used protection: how irresponsible of me! I was not on birth control, and did not know if he had any STIs. The following day, I drove to a neighboring city to buy Plan B (I didn’t want to risk running into someone I knew). And I have since gotten tested.

David emailed me 3 days after the fact. He basically wanted to make sure I was okay, apologize, and ask me to keep what happened to myself. I told him that I was fine, and that I would not interfere in his relationship anymore than I already had.

I wish that he would have told his girlfriend. I know that the fallout of doing so would likely be horrible, considering the small town we are from, but I hate that she doesn’t know. I wish they would break up, or he would tell her and they would work through it. But getting married while holding that big of a secret would be so unhealthy for him and unfair to her. It’s just an awful situation.

I am also not thrilled about the fact that I was so drunk. I did not envision being wasted during my first sexual encounter. I don’t even remember how my first kiss happened, and that almost bothers me more than the sex.

I was never planning on saving myself for marriage, but there was also always the possibility of loosing my virginity to the love of my life, and spending the rest of my life with that person. Now that possibility is gone, which just feels weird.

I have mostly gotten over any guilt or bad feelings regarding his girlfriend, the unsafe sex, and the being super drunk, but the one thing that really weighs on my heart still is that I had sex with my brother’s best friend. I know my brother would feel so betrayed by both of us if he knew. I share everything with him, but this is something I will always have to keep hidden. And I absolute hate myself for that.

However, forgetting all the circumstances surrounding it, the sexual experience itself was fun, and David was the best first partner I could hope for. I just wish that it didn’t have to be a one time thing. I’ve gotten a taste of it now, and don’t want to stop. I wish David and I were in positions to be friends with benefits.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Plan B / Emergency contraception

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told my best friend. She was very supportive. She talked me through a lot of the guilt I was placing on myself, and made me realize that I don’t have to feel like a horrible person after doing this. She was also very excited for me once we shoved aside all of the circumstances that made the hookup so complicated.

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

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? -He had a girlfriend
-I was wasted
-We did not use protection
-He is my brother’s best friend

What was the BEST thing about this hookup? He was super sweet and communicative and attentive, and made loosing my virginity a fun experience.

What was the WORST thing about this hookup? The guilt and circumstances surrounding it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It made me realize that sex is not that big of a deal. I did not catch feelings for David, even though he was my first, but still had a fun time despite having no romantic connection. I don’t know if I want to have more casual sex in the future, but it helped me realize that sex is not as big of a deal as it was made out to be in my mind. I realized that even though I thought being a virgin was a huge deal, now that I have had sex, I realize that whether or not I am sexual active, that carries no weight on who I am as a human being.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Get rid of the stigma. Remove some of the importance placed on sex. There is this idea that our value as humans is tied to sex, and that is just an unproductive and destructive misconception.

What do you think about the Casual Sex Project? What a great idea!

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