My First Time Was Really Awkward. Now What?

Dear Heather,

My boyfriend and I attempted to lose our virginity today… and it was a little rockier a process than we had initially anticipated! When he tried to go in, it wouldn’t go in past the tip and even then it’d keep slipping out. In addition to not getting to really feel it that much, I became distracted by trying to help him get it in that I couldn’t enjoy it much.

I felt really embarrassed about this and although he reassured me that he loved it anyway, and the reason for the difficulties was probably due to the lubrication on the condom and the cramped position the couch put us in — I’m not really convinced. I was also confused because I was super wet when we did it and the condom was lubricated… yet that only seemed to worsen the slipping.

I can’t help but feel like I screwed up our first time somehow and it’s made me kinda depressed. Also I’m not even sure to consider myself a virgin or not cause it didn’t go in all the way…

It sounds like your first time was really, really — normal! Even though sex looks easy and awesome in the movies and on TV, in real life, it can be awkward, confusing, and pretty messy. It’s all part of the fun, and it’s totally okay.

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You should really accept and believe that not having the “perfect” first time is not at all your fault. I’d actually say this was a much better experience than a lot of gURLs have. Think about it: you wanted to do it; you used a condom and were safe about it (yay!); you were with a person you felt comfortable with who didn’t make you feel pressured, and who later reassured you that everything was fine (he sounds like a great guy, by the way); and it didn’t hurt. Be proud of yourself, not depressed, about what happened!

For more success next time around, try relaxing yourself as best you can, especially your pelvic muscles. A cramped couch might not be the best place if you require a some space to get cozy — find someplace private and comfortable for the both of you. This will help him get inside of you easier, and will allow you to enjoy the experience. Even though the lubrication can make things slip and slide, it’ll make things feel great once he’s inside of you. You could also use a non-lubricated condom — it just might make things a little painful if you’re not wet enough. Go slowly, communicate before and during the sex, try out different positions, don’t just focus on “getting there” and instead keep your energy and thoughts on how amazing it feels to be intimate with your partner.

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Feel free to giggle and laugh at the situation — it’s totally allowed during sex. If you find that you’re still not ready when you try again, take some time off to build up your confidence. This won’t be the last time you get to have sex in your life. The more pressure you put on the situation, the more likely you’ll let yourself down.

And as I’ve said before: Virginity is a state of mind. There’s no real definition of it. If you still feel like you haven’t officially done it, then sure, consider yourself a virgin. Totally up to you.

Let me know how it goes, okay?

WDYT gURLs? Was your first time anything like this? How did you make it feel better the next time? Share your stories and advice below!

take care,

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Posted in: Help Me Heather, Love Advice, Sex, Sex, Virginity
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  • tonya leevy

    Well am 15 my bf is 20 he want to have sex with me but am afraid it will not go well any advice pleaseeeeeeeeee help

  • Mandy braid

    Oh my god, just reading through some of these comments makes me weep for the future! Firstly, if you’re so dumb that you can’t even SPELL sex, you shouldn’t be having it. Secondly, a lot of people on this forum are saying they’re only 14. Now I don’t give a shit what other people do usually, but I feel obligated to remind you that at 14 you are still A CHILD! You are not in love at 14 after being in a relationship for 6 months, and even if you were, you are too young for sex! I lost mine at 17 after being in a relationship with a wonderful guy for 2 years, when we were both ready and committed to each other and emotionally evolved enough to have sex. Sex will always be there, don’t fool yourself into thinking that “ur in luv wif him” and just wait until you’re old enough!

  • christa

    Iam a virgen and realy shy 2 do it because aim not sure what he likes (on me) I realy whant 2 do this but aim realy waried of he would think of me naked aim 15 and he is 18 I realy do love him and whant him 2 see me love him in a sexual way but what do I shave my self or what. And what about my strech marks how do you please him in bed. Any ansers plz plz HELP realy whant 2 do this

  • Lukman

    Me nd my girlfriend are 17,we want to try having sex bcox we olways have sexual excitement wen we r chattng in a social chat.plz we nid hlp!

    • Demi


      If you want to have sex, have it somewhere you feel comfortable, you’re bedroom, hotel etc.
      But you shouldn’t just say ‘hey, lets have sex now’ be spontaneous, it will happen, just kiss her normally then get to feeling, slide down her knickers, then take her trousers off, then….

      But try to make her feel comfortable, most girls bleed when they are loosing their virginity, so just keep going, its normal 🙂

      Hope this has helped.

  • Chloe

    Hello my name is chloe & I am 16 and still a virgin . Im very curious and oi want to know what,t feels like to have sex . But I am also affaird that he will not be satisfied or maybe even what he will say afterwards . What if I bleed ? Idk … But I really want to try it

    • Chloe

      Also ive never been fingered before but I have used tampons . Does that mean I have a loose, vagina ¿

  • Chaido

    I’m fourteen and I had sex with a guy. Worst mistake ever. Sure it was great the time, but afterwards, he was so clingy and ended up wanting it all the time.
    Just be aware of that.

  • Nelly

    Two days ago, my boyfriend and I finally decided to lose our virginity to each other. I’m 16 and he’s 18. Although it wasn’t completely planned, he was excited and he managed to get it in all the way. My problem was that we kept changing positions and no matter what, I just wasn’t feeling anything great. In the end, he had an orgasm and I didn’t. I’m hoping our second time goes better :/

  • Tori

    My boyfriend and I just tried to have sex today. We’ve been together for a long time and we both decided to try. But the problem was that we couldn’t even find the right place to put it in. I’m not even sure where it goes and when I thought we had it he couldn’t get anything in past the tip. I was plenty wet and we also had a lubricated condom. We tried several positions and still couldn’t do it. Help!!

  • allan

    hi my name me is allan and im in my late 30s and tomorrow i am having my first time if all goes well. i am nervous anxious and when im like that i tend to poo my pants and im worried that when my partner rips my pants down there will be poo in my pants.
    i dont know what to do, help me A.S.A.P ?!

    • Bobby

      Me too. I was so scared it was only me that this happens to.

  • Aly


  • Lena Duchanes

    , I am 16, and me and my boyfriend tried, we tried for an amazing three hours and got no where. I’ve been with him for a bout two years and he’s amazing, but when it came down to it he just couldn’t get a hard on. I have no idea how to fix that. We tried, but to no avail. My friend suggested Viagra, but he’s so young to have that problem. Does any one have any advice ? I am pretty sure we started off o.k, and he said it was amazing, but I still feel terrible I couldn’t make it happen.

    • Sugar-foot

      You should try sucking him off or some foreplay.Maybe you should try playing with his penis and kissing him down.

  • Jade

    I will be 14 next year and I really eant to no what it feels like my bro wuz 14 when he lost his but idk what to do I am single and idk what to say to my oarents after its done I need help please?

    • Lena Duchanes

      well, you don’t necessarily have to tell your parents. They honestly can’t tell. If you feel more comfortable telling them though, you should. Just be sure that they aren’t mad before you tell them.

  • abiola

    Am 17 and my boyfriend is 18 we tried hving sex 2day and I tink I lost my viginity although everything dint go in he was scared 2 continue bcos I started bleeding
    I was bleeding 4 four hours 🙁 twasnt painful tho’, am just scared if we try again d same thing would happen? Pls help

  • catherine Smith

    We have the perfect e-boo for newbies it will help you both emotionally and physically.

  • Annie

    The first time I had sex was last year. It didn’t hurt at all for me, and there was little blood. Honestly, I think it went quite well, although neither of us reached orgasm, it was still pretty good. I’ve had sex many times since then and I think it helps the first time if you’re comfortable where you’re doing it, and you’re with someone you trust. Be prepared and smart; use a condom! Talk about it with your partner. And don’t do it unless you are ready.

  • Jordan

    Me and my boyfriend have tried orale sex a few time but never really got it in, we are very comfortale around eachother we just dont really know what to do we are both virgins btw.. any help?

  • Tallie

    My boyfriend and I had a very similar experience today.
    I am 17, he is 18, and it was the first time for both of us. Neither of us really knew what we were doing, and we were both very nervous, so it turned out to be a bit of a shambles and needless to say, nothing really happened. He had a bit of a difficult time actually getting in to begin with, and then we just found it awkward to move and it was very painful for me – we were able to have a laugh about it though, and afterwards we did some research and found out a more efficient way of doing it, which we will try next time. I think we just rushed into it, and we were both so overcome by nerves we didn’t focus on making it feel good like we were supposed to. 😛

  • aydee

    ok honey if u r not realy dnt do it. If he loves u he will wait for u.

  • Brooklyn

    Ok so I’m a virgin & my boyfriend wants 2 have sex. We’ve been together 7 months & our anniversary is coming up. I’m afraid I’ll disappoint him because he’s had sex with another girl. I’m willing to have sex but I don’t wanna make a fool out of my self! What do I do? Any advice?

    • aydee

      honey if u r not ready dnt do it. If he loves u he will wait. 🙂

  • Alexis

    hey there,um well im still a vergin but i am scared to lose it because im scared im going to make a fool of myself. and im a very cllosed quite kind of person so i think t would be a bit awkward if i like, do somthing weird (lol) but i am 14 and have an amazing boyfriend and we are both vergins. But i can’t really find a guy that i am confertably around (as in friend wise) and i scared that even if i was confertable with the guy, that i would just make a total fool of myself and i hate being imbarest but i am confertable around my boyfriend and everything but i wouldnt be if we tryed lol oh and i have to mention that iv never madeout before, what should i doo!?!?!?! pleaseeeee help!

    • neha

      Dont do control ur feeling and be vergin. U wil feel great when u wil say 2 others that u r vergin….