Monday, March 20, 2006

I Bet She's Still a Virgin But It's Only Twenty-Five 'Til Nine

The title's a lyric from one of my favorite Tom Waits songs.

But he's right, you know. For most of us (with key exceptions, of course), after a certain amount of time, the loss of our virginity was inevitable.

The whole discussion surrounding the post last week about the term "defloration," particularly the comments about whether loss of virginity is appropriately celebrated and revered in the modern era, got me thinking more about my first time, and about others' experiences that I've heard about.

If there is no formal ritual or celebration for loss of virginity anymore, are most people substituting their own ritual and celebration? I wonder.

For myself, my entree into non-virginity was most certainly planned. But not, I suspect, the way most such planned instances probably are. Though I could be wrong. I always picture the "normal" girl planning it in a very hearts-and-flowers kind of way, like they always show on soap operas and those dreadful WB teenage dramas. Candles, rose petals, lots of declarations of love by your young boyfriend/girlfriend.

I had sex for the first time later than some people did. Strangely, none of my boyfriends in high school ever pushed even slightly to have sex, and though I liked physical contact, I didn't feel any urge at the time to have sex with any of them. As an aside: I wonder sometimes if the widely held belief of both teens and adults that most teenagers are sexually active (or want to be) is actually true. It certainly wasn't my experience. Maybe it's more of a myth than a reality.

I also had (and still have) a stubborn, independent streak. Even as a young teen, nothing disgusted me more than people who just did things because everyone else thought they should--whether those things were mainstream or counter-culture. And I was determined that before I did or tried anything, I would be certain I was doing it because I wanted to, not because someone else thought I should, or because someone else was trying to manipulate me by trying to make me feel bad, guilty, "uncool," or "slutty," or whatever their M.O. was.

Sex fell under this rule, too. I thought it was stupid how people made such a big issue about whether you were a virgin or not. I didn't think virginity OR non-virginity was such a big deal. I fully expected to enjoy sex when I wanted to have it. But I sure as hell wasn't going to do it until I was damn well ready--and no one else was going to convince me I was ready because they thought it was something that "should be done." I wanted someone else like me, for whom it was no big deal, either way.

Obviously, that left pretty much most college guys out. At that stage of the game, whether they could bed you or not was a VERY big deal to them. The vast majority of guys at that age aren't looking for anything more than the ability to improve the stats on their scorecard, so they can wave it around in front of their buddies. There were a lot of guys who wanted to sleep with me when I first started college, but it always felt too much like I was just going to be a notch on their belt. Plus, despite my own inexperience, I could tell based on the other things I was doing with them, that their technique was certainly not polished. Most of them were pretty fumbly and clueless. In short, I sensed they didn't really know what they were doing, or how to proficiently maneuver a woman's body to full arousal, and hence I felt fairly certain that a first time with any of them wouldn't be any too great. So I turned them all down.

I think most women my age didn't really think about that. And I wonder if as a result a lot of them had disappointing first times with their college boyfriends. Don't get me wrong, I understand that it's only natural most guys at that age are somewhat clueless and clumsy, and it's not their fault--they have to start learning somewhere, after all. My hat is off to all those women who were cool with assisting the boys during their practice runs and scorecard years. I just personally wasn't cool with that. (Sorry, college guys.)

Anyway, because I couldn't find my guy with the "no big deal" attitude I wanted, I set off on an alternate course. I was working in New York City in the summer, and through my job I met a now well-known journalist/writer who at that time wrote for a music magazine. He was cool. He was much older than me (12 years). He was funny and smart and smart-arse-ish and a talented writer to boot--a deadly combination for me. I liked him. I didn't ever feel for one minute that I loved him, and I knew I wouldn't ever feel that way. But I really liked him and I was highly attracted to him. We started hanging out together.

And, obviously, unlike the college and high school boys, he knew how to touch a woman. He'd done it a lot, and he made no secret of that. He was a horny bugger. And when we were seeing each other, I knew I wasn't the only woman he was seeing.

The fact that I was a virgin was, of course, endlessly intriguing to him. He'd slept with a lot of women, but never with a virgin. So yes, there was a scorecard element involved with him, too. But the difference for me was, he didn't lie and pretend the scorecard motivation didn't exist. As with all the people I like most in my life, and unlike all the other guys I was dating at that time, he laid it all out on the table for me, unapologetically, and let me decide if that worked for me or not:

1) I want to sleep with you because I think you're hot.
2) I also want to sleep with you because you're virgin, and the thought of teaching you and being someone's first lover turns me on, and I want to see what that will be like.
3) If you want to have sex with me, I'm going to be right on it. But you don't have to sleep with me if you don't want to. I won't be angry at you if you don't, I won't stop talking to you if you don't. I have a lot of other people in my life I can get sex from, if I need or want it. If you don't want to, no big deal. We'll hang out, make out, whatever you want, and I can get sex somewhere else. What happens with us is totally your choice.

So there it was. No big deal. My choice.

I found the fact that he wasn't trying to hide anything from me very appealing. And though many people I've told the story to think that #3 above sounds manipulative, I can tell you it really wasn't. He wasn't threatening, "If you don't give me sex, I'll go somewhere else." I was clear he had other lovers, and I was fine with that--they weren't a threat to me. And I was clear that even if I did have sex with him, he'd still have other lovers besides me. He wasn't a monogamy guy, and I didn't want him to be. At that time and in those particular circumstances, it actually made me far more comfortable to know he could offer me the no pressure option by going elsewhere, rather than me being his only sex option and having him to be totally focused on getting me to go to bed with him. That he could say, "no big deal for me either way," was really what I needed, and knowing that there was absolutely no pressure or hidden motivations (or hidden lovers) was an incredible relief.

It may not sound romantic to many, but I recognized this was the perfect scenario I personally had been waiting for. I wasn't being pushed, it was all my decision, and there would be no whining or resentment if the decision was no. But if I said yes, I would get to have sex with an experienced man who liked women, who could really initiate me knowledgeably into things I wanted to know more about, and who I found sexually and intellectually appealing.

So I said yes. And one night while I was staying over at his place I had sex for the first time. And it was good. I don't think I came that night (I almost never do the very first time I'm with anyone), but it was very pleasurable, and I learned a lot.

There were no rose petals, or mood lighting (unless you count his cigarettes as mood lighting). There were no false (or true) declarations of love. But there was moonlight coming in through the large windows of his East Village studio, and we were surrounded on every side by books and music, and there was no pretense. And best of all, there was no fumbling.

And for me, that was perfect.

In the morning when we woke up, I don't remember much of what was said, but I do remember there was no embarrassment, shame, or immaturity, just friendly, adult affection and camaraderie. I had no regrets. I'd had a good time. But it still didn't seem like people should make such a big deal about the transition. I was perfectly happy I'd had sex, and it had been good sex. But I didn't feel any better or worse than I had the day before, when I was still a virgin.

As the more experienced person (and seeing as he was a music writer), you'd think an extensive review would have taken place. I'm sure I asked for feedback about what he'd enjoyed and any pointers he had, because I'm like that. But it's all rather hazy. My memory only clearly holds two comments of his that morning after my first time: 1) he called me a sex kitten, and 2) he remarked how incredibly pragmatic I seemed to be about the whole thing, which he hadn't expected, given it was all new to me. I remember feeling pleased with both reviews.

So, in the end, not much ritual or celebration. But in a way, there was a certain approach to the event I wanted to create, and I waited until I could make that happen. So maybe in a strange sort of way, it was a little ritualistic (in my weird mind, anyway). In any case, I felt good about the way it (and he, heh heh) went down. I think a more formalized celebration or too many flowers and hearts would have killed my enthusiasm for the event, not enhanced it.

And that, my friends, is all she wrote. For tonight.

So, how about your first time? (And by "first time," I mean the first time you had sex by your choice). Ritual? Celebration? Humiliation? Planned? Spontaneous? One of those classic rose petal moments? A bleah time in the back seat of a car? Someone you liked? Loved? Someone who "would do?" Good, mediocre, just plain awful? Were you pragmatic or romantic, or both? And if you planned/prepared it ahead of time, did it turn out as you'd imagined it would? Gimme the goods.

And as always, remember you can post anonymously if you want to.

(Photo credit: The Morning After by stepha1202.)


Anonymous Cherrie said...

Would it surprise you to know my first time was with another girl?

I was 16 and a junior in an all-girl Catholic high school. Contact with boys was limited to the occasional arranged dance with the all-boys school across the athletic fields. The boys were pimply and dorky and frankly aroused nothing in me. But A did.

A was a curvy, happy girl whom I first met in one of my freshman classes. We slowly became friends, hanging out occasionally at each other's houses or the mall, just watching TV, talking, laughing and becoming more comfortable with each other.

One warm afternoon we were alone at her house, listening to records and talking about people we knew. The subject turned to a teacher who was widely suspected (in those less-enlightened times) of being a "dyke," a lesbian. I said I didn't understand what the problem was with that. Why couldn't she live her life as she chose, with other consenting adults?

Just then the record ended. We stared at each other in the suddenly awkward silence, and I felt an unfamiliar but irresistable urge to touch her, to hold her. I reached out to her. We embraced. We kissed.

What happened next was a blur, but we ended up nude on her bed, exhilarated and exhausted. Neither of us really knew what we were doing, but even though I don't think my hymen was ruptured A managed to hit enough of my high points for me to have several fledgling orgasms, and I think I got her off too.

We stayed friends for a while after that, but never got it on again, alas. Perhaps we were too embarrassed--not because we were girls who made love, but because the sensation of lovemaking was too new and strange to assimilate just yet. In time A drifted away, and I have no idea where she is now.

In time I began to find men who interested me sexually, but I have always had room in my life for female sexual companions, and about half of my lovers over the years have been women.

3/21/2006 12:00 AM  
Blogger Miss Syl said...

Cherrie: Wouldn't surprise me at all. Does it surprise you that my first time was with a man? ;-)

That sounds like a perfectly lovely intiation into sexuality. And completely spontaneous, too. The complete opposite of my situation. I always did think too much...

3/21/2006 12:07 AM  
Anonymous Hiromi said...

I'm a born contrarian. I never thought virginity or its opposite was a big deal, and I resented how much importance was placed on it. My first time was with a guy who I liked but was just all right. Why him? I finally got horny enough, that's all. I also just shrugged when I first got my period.

We have so many other rituals that mark our progression through life - graduations for example - that I think are more significant.

3/21/2006 1:46 AM  
Anonymous Tory said...

I had no idea what was in store for me. I think the girl kinda had it planned. I was hanging out at a friends house one night during the summer right before my freshmen year. This girl who was a friend of my friend's family and was living there cuz she was having problems at her home. After fooling around with her for a couple weeks, one night I was fingering her on my friends couch. Out of no where she unzips my shorts and pulls out my dick while profoundly stating that she wants to fuck. I was dumbfounded and couldnt pass up the opportunity. The sex was horrible in comparison to what is happening now a days. I can remember being so scared I never even got my nut. I had started my first friends with benefits at 13 1/2 with a 16yr old. That was a bitch'n summer.

Celebration? I can remember walking home that night at 3 in the morning pumping my fist in the air hooting and hollering. laughing with myself thinking I totally just banged some chick. Of course i was a punk ass kid and told everybody what happened. I was the youngest in my group of friends but the first to have sex. All my friends wanted to know everything. I got the congratulatory high fives and all that from friends.

3/21/2006 3:20 AM  
Anonymous Cherrie said...

Ah, the teenage equivalent of the Erica Jong "zipless fuck."

So, Tory: Did she get off? Was it weird when you stopped? Did you ever get it on with her again? Did the encounter give you more confidence for the next time?


3/21/2006 8:13 AM  
Anonymous Darkhawk said...

To understand my first time, I need to share some context.

I was sexually assaulted when I was fourteen, by my first boyfriend. He pushed at me hard enough to break me, but recognised what he was doing before pushing through to rape. This was the culmination of a pattern of interactions -- I wasn't sure what I wanted with him, because he didn't give me time to think about what he was doing before going to something more intense. (I don't think well on my feet, especially under pressure.)

This left me with some lasting damage that I haven't managed to entirely deal with even these years later. One is that I am stressed by displays of interest, especially outside an established relationship; the other is that I have a lingering terror of initiating sexual relationships. (A fear that I have only faced honestly twice, and only actually addressed once. Who knows whether, in the event that I ever take a new lover, it'll still be there? It's not a frequent event.)

For much of my adult life, my attitude towards my own sexuality has been one that involved pushing my own boundaries faster and harder than I was comfortable with, just so nobody else would do it for me, because I could handle it when I pushed me, and I couldn't handle it from the outside.

Some of this was healthy assertiveness -- I've been fairly clear on when I'm interested in people, and I tell them rather than doing the girly-wait-and-drop-hints-to-see-if-he-wants-me thing. I never crossed over into stuff that was unhealthy for me, but I sometimes ran the ragged edge of pushing too hard too fast, because the fear drove me.

So anyway. There was this fellow. I was sixteen; he was a year and a half older. He knew I fancied him, because I'd flipped a note containing that information into his lap and run like hell. (Growing into confident assertiveness took longer than the clearish communication.) He took to flirting with me, bits of physical affection, and eventually I asked him straight out what his interest was.

So we wound up involved. He was safe and secure, damn pretty, a genuinely good person. I liked him a lot; I soon grew to love him. And fairly soon after we officially initiated our relationship, I propositioned him.

Confused the hell out of him, too, that I was that blunt and interested in him that way.

We were both virgins; he was a freshman in college. He was more coherent and responsible than I was; he had also spent between the ages of fourteen and sixteen working in his town's public library and read the entire science fiction section and all the books on human sexuality. So as first times involving virgins go, ours -- a scheduled time alone in his dorm room when his roommate was out -- was not bad at all. He knew the theory. We got better rapidly, learning how the sex thing worked, making dates for weekends or sneaking time in his room in his parents' house.

And Syl, six years later I married him.

3/21/2006 4:31 PM  
Anonymous Anonymous said...

My first time, I was 17 and it as with my boyfriend at the time, who I'd been dating for well over a year at that point.
We were both virgins, both totally inexperienced before we started dating. So we took things at our own pace.
by the time we actually had sex we had done pretty much everything else, were comfortable with eachother's naked bodies, and were pretty good at getting each other off.

I was the one who wanted to have sex. i went out and got myself on the pill before we ever started having sex, and had to spend some time convincing him that it was a good idea.

The sex was clumsy & fun. We were giggling the whole time, and I don't think we stopped laughing for about 15 minutes afterwards; it just felt so weird!
I didn't get much out of the sex that time (oh how things have changed!), but he got me off beforehand.

It was an excelent intro to sex overall. I didn't have any ridiculous expectations, and by doing everything else first, I learned that there's far more to sex than just intercourse.

I dated this guy for 3 years, then a year after we broke up we started having sex again, as friends, and that's still going strong.
The sex is much better than it was that first time!


3/21/2006 6:04 PM  
Blogger Miss Syl said...

Hiromi: "I'm a born contrarian. I never thought virginity or its opposite was a big deal, and I resented how much importance was placed on it."

Same here. Do it, don't do it...whatever. When you're ready, you're ready, and that's that.

Tory: Look at you, romancin' the older women's pants off at 13 (and a half, but of course!). Not an unlucky number for you, I'd say. Thanks for sharing the story. Oh, and what Cherrie said.

Darkhawk: Aw, that's so sweet! Are you still together? I'm glad you found somone good and kind who treated you with the respect you deserved after your early more negative experiences. Assault changes you in so many ways that you may not realize at first, and makes relationships so much more difficult to navigate sometimes. I'm very happy you were able to find a good one.

vistana: There seems to be a theme in a lot of these stories--the girl is the one propositioning the guy. Interesting. Not the way they'd lead you to believe it usually happens. I'm glad the ladies are stepping up. Thanks for the good story. I've often wondered what it would be like for two virgins to have sex together--if it would be good or just plain awful. I'm glad your experience was good.

And yes, it's been my experience that the sex gets better and better the older you get, so you've got a lot to look forward to (as do we all).

3/21/2006 10:30 PM  
Anonymous Darkhawk said...

We are, indeed, still together. And he is still a good one. :)

3/22/2006 12:43 AM  
Anonymous Tory said...

I highly doubt that she got off. I only went for 10 minutes or so. If she did props to her for making it happen because it was surely more her doing than mine. It was a tad bit wierd once the sex stopped and I had to pull up my shorts but then again I was still in shock from everything. I was pretty fixiated on what just happened. My senses were dull.

Yeah I messed around with her the whole summer. I had the perfect situation. After my parents split my mom started working nights and slept all day. My best friend's mom was the same working nights too and was a detention officer for the local jail. That girl was living at my best friend's house. It was quite convenient. No supervision what so ever, plenty of alcohol and drugs. I ran a muck for the summer doing as I pleased. Having that girl to take me and my friends around in her car was almost a better perk than the sex.

Then right as school started she moved back home. Never to speak with her again. I was in high school with her for 2 yrs and might have said 2 words to her.

Oh yeah I had way more confidence after having sex the first time. I still really had no idea how to fuck but my thinking was "it couldnt have been to bad cuz she is coming back for more." It is like anything else, once you accomplish the goal the first time you have the courage to do it.

Yea Miss Syl, the majority of my relationships are with older women. Things tend to work out a lot better with older women. They are usually more mature, chances are they know who they are already and they are a lot less inhibited when it comes to sex. Good times

3/22/2006 3:26 AM  
Anonymous Cherrie said...

Thanks for the added details, Tory!

I should throw in my story about my first time with my current man. Like Vistana, I knew I wanted him, we had explored each other's anatomies at length in the back seat of his car, and we were ready for the next step. I was on the pill, and I was hot and horny!

I arranged to get the keys to a friend's condo for the weekend while she was out of town. We arrived late at night with a takeout pizza and wine, stripped seductively for each other and, in between kissing, licking and biting each other, ate and drank in the nude. Then we went to my friend's bed to get it on.

Only problem was, my friend had cats! The cats apparently slept on or around the bed, and left their hair and dander all over. As we entered the bed, my man's eyes began welling up with tears, he began to cough, and eventually his skin began roiling up in welts. As luck would have it, he was allergic to the cats! He tried to get it up and do me, but just couldn't hold an erection, and eventually he went home. I was so frustrated!

But I still wanted him, and we fucked for the first time in a hotel room a few days later--successfully, too. That was 29 years ago and I've been with him ever since. But we've never owned a cat!

3/22/2006 8:30 AM  
Blogger Miss Syl said...

Tory: Older women everywhere stand up and applaud you for your intelligence and good taste. :-)

Yeah, for the life of me, I'm never understood why so many older men lust for very young women. In terms of sexual satisfaction, they'd be getting a much more satisfying experience with an older woman.

While the thought of seducing an innocent young thing is a nice fantasy, in my reality I'd much rather have an older, more experienced man who knows what the hell he's doing. And then some.

3/22/2006 9:33 AM  
Blogger Miss Syl said...


Aw, another sweet story (except for the welts part). You know, I think that's why I never *really* got the whole focus on the "first time" thing. For me, every first time with a new person is like a new initiation into sex and all its possibilities. No two people are the same in bed. And no two people together perform the same together in bed. It's pretty cool.

I've never yet had a boyfriend allergic to my cat. I wonder what I'd do if that happened...

3/22/2006 9:36 AM  
Blogger Anastasia said...

I put sex up on this huge pedestal and I didn't really consider other factors, as to whether the other person was, indeed, a considerate person in general (consideration being proportional to sexual consideration). In short, women, even now, are bombarded with how they should 'be' or how 'sexy' they should be, regardless of the other person, just as long as they're 'attractive' and available (magazines, film, television). I thought the first time would mean seeing stars, only because my then girlfriends (who lost theirs before me) elevated it (the female equivalent of machismo) and was somewhat disappointed afterward (whereas I romanticised it during, and a little after), but that didn't last long. I didn't mull over it. It was more a case of 'next' for me rather than dissect the experience.

3/24/2006 2:55 AM  
Blogger Miss Syl said...

Ana: You know, just realizing after reading your post that I didn't experience a lot of that female machisma romantacizing. A lot of my girlfriends were virgins through high school (at least, as far as I know--they didn't say if they weren't). I can only think of one who I know for sure was sexually active, and though she seemed fairly proud of the fact, she didn't romantacize it. She was more into just bragging about how knowledgeable she was, and that, combined with the fact that I thought her boyfriend was the LEAST likely person ANYONE would want to sleep with, served to just annoy me more than make me think first sex was going to be some mystical event.

3/26/2006 11:24 AM  

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