Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

Your First Time – The VERY First Time

I spend way too much time online.  Between my blog, and the private messages I get from readers here on OnSugar (always a good way to reach me, btw) and Twitter and reading and commenting on other people’s blogs, I probably spend more time online each week than I ever did reading traditional periodicals.  The majority of that time is interactive, in other words, I’m exchanging ideas with people.  I’m not just passively reading.

Anyway, sometimes I find myself thinking and writing about things that I otherwise wouldn’t.  It’s just that other people bring these topics up and then they get stuck in my mind.  Here’s one of those topics – First times.

I know exactly one person – 1, who has only ever been with one partner.  Her husband.  They didn’t wait until their wedding night.  But he was her first and they ended up marrying pretty young and now it’s nearly 20 years later and they’re still together.

I don’t know anyone who waited until their wedding night.

I know people who’ve had a couple/few partners and others who’ve had dozens.  People who first had in their early teens and others who started in their twenties.  And yet with all of this diversity I’ve never heard a single positive story about a .  Ever.

Maybe the people with the happy stories keep them to themselves?

I’d like to know.  Seriously, I’d like to know if there’s anyone out there who has fond memories of their first time.

Your First Time   The VERY First Time sex dating polls  button1 addthis

  • I’m a . Still waiting for my first time. (125 votes)
  • My first time was special and beautiful. (101 votes)
  • My first time was awful. I’d rather not think about it. (104 votes)

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57 to “Your First Time – The VERY First Time”


  1. Anonymous says:

    I picked awful because it was physically painful. We had tried to do it a couple times before but I couldn’t handle the pain, so finally I just sucked it up. Other than that it wasn’t a horrible experience though. Certainly not an “I’d rather forget about it” moment. Far from it. It was just ok – not fun but not terrible.

  2. grad student says:

    OK. First time was forgettable. In fact, I remember afterward thinking “This is it? THIS is what I have been so wanting? (I was 18, she 17) ” I mean, as a guy through HS I had practiced solo plenty :) and thought the real thing would have been so much better.
    I stayed with her for awhile after that, but eventually she had to leave me cuz her church didn’t like the kind of people who listened to the music I listened to (Guns N Roses mostly). I guess they (her Church) got over the fact that she had slept with a married Deacon (which was why she wasn’t in the church while we were together)

  3. grad student says:

    On another note. My cousin is raising her daughters to know that they can say No to people whenever they want. They don’t have to do things they don’t want to just to please someone. Friend invites you to a b-day party but you don’t want to go? That’s ok. Be honest, don’t go just to please someone. The girls are pre-teen. I hope they really get this attitude and use it in ALL decisions.
    The stories of girls that were forced or raped for their first times just disgust me. Even more, though, are the stories where she ‘gave in’ cuz he wanted it so bad. I mean, rape is a violent crime and horrible, but giving up your own power by ‘giving in’. I am not saying they deserved it or anything like that. I guess I didn’t realize this attitude of ‘pleasing everyone’ was really out there. While maybe picking up mail or checking on the dog or giving a friend a ride are nice things you can do sometimes as a sacrifice for a friend, letting someone enter your body is not. ANYONE who says “you would do it if you loved me” DOES NOT LOVE YOU. Hell, he doesn’t even respect you. You don’t have to give in. And guys; STOP IT. You can tell when she is giving in just to shut you up or to make you happy when she doesn’t want it. Ask, maybe a follow up then be done. If you are begging, wheedling, threatening and pouting to ‘get some’ then she didn’t want to.

  4. grad student says:

    Last one here for me. About the DRUNK sex. First, if you (guys) find a girl drunk/passed out and you touch her sexually, that is rape. That’s it, it’s rape. No defense
    One problem I have is the idea that is out there that every sex act with a girl who has been drinking is rape. It is out there. The argument is drunk = inability to consent. Can’t make that decision.
    Problem: Remembering college parties (and hearing the stories of the current scene) guys and girls are keg-standing, drinking, etc. If both people are drunk, who raped whom? Seriously. A drunk hook-up you regret later does not equal rape. Again, a caveat. IF you (fella) are priming the pump, really pouring drinks and trying to get her drunk to take advantage, again… rape. you are intending to sexually assault someone after incapacitating that person with booze.

  5. xothabesto says:

    alriqht soo ma 1st timee was interestinqq. i was scared 2 qive it up 2 him but gave into peer pressure & we ended up chilling at my house we had it all planed i tld him 2 pring thaa protection & watevaa sooo we have this routinee of we kiss touch finger / jerk & everythinq thenn like we did our routinee like 4 times but qot knockings at ma door thenn i was jus like okay – if we qonna do this we needa hurry up cus im gettin tired of waiting [ BLUE BALLS MUCH ] haha ima qirl thoo but yeaa thenn he put it in a felt a pinch of pain but thenn we let it all goo & stuff then he wanted me 2 get on thaa top but i was still in pain so i left it at tht & after tht we had sex one more timee & i noticed sex is not a big thingg – we needa focus on our reationship more & so noww thts wht we doinq & tryinq to refrain from sex becaue i wanna wait

  6. aliexya says:

    Oh goodness. I just joined, and I just have to comment on this one. My first time is something that used to fit in the catagory of “I don’t want to talk about it” but over the years I’ve learned to laugh about it, because it was truly a hilarious situation when you think about it.

    I was 15, and had been dating this guy for a little while. One day, we cut school early and went to my ex-boyfriend’s apartment (we were still very good friends, and it was my ex who introduced me to this guy – the irony is almost painful) with another friend of mine and her boyfriend. While my ex went out on the balcony to smoke (I know, I know), and my friend and her boyfriend were making out on the couch, my boyfriend led me into the nearest room for a makeout-session. Only, the nearest room was my ex’s and we ended up doing more than making out (he had a condom, and I was horny). On a chair, with me on top, no less, because the bed was small and the floor was messy.

    Scary thing? It’s not the worst time I’ve had :)

  7. Tsee says:

    Well, I’m arriving pretty late, but my experience wasn’t so different from everyone’s. It was his first time as well. It started on one of our weekend getaways, and as horny 20yos we made out like crazy, with all kinds of external sex. He was sweet, and waiting for me, I think he actually never brought it up. All of our advances in caresses (first boyfriend) were slow, one of us would make a small move, see how the other liked it, sometimes recede, but mostly go ahead.

    So, that night, I asked him. He was happy, I was happy, we had protection, everything seemed awesome, except that we didn’t know how to make it go in. We tried a dozen positions, we made out in between, but no. So we gave up.

    About a week later, after a few more failed attempts, I said: “ok, let’s get this over with!”. So we used some KY, we got him ready, and I focused on getting him inside. It wasn’t pleasurable (not even for him, since I asked him to take it out since it hurt a bit), but it felt like accomplishment. From then since, it’s been great.