Your Turn: “It’s Been Six Months and all We’ve Done is Kiss”

In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me:

I’m 28-years-old and six months ago I started dating a wonderful man. He’s 27, and treats me with more respect and kindness than all of my other exes combined. I am incredibly happy. I knew him socially before we began dating, so I was aware of his painful shyness. It took him several months to muster up the courage to ask me out, and I happily accepted. We had been dating for nearly a month, and in that time he had yet to try to kiss me, so one evening I suggested we get this over with and I planted one on him. He confessed a few days later that I was the first girl he’s ever asked on a second date. I may or may not have been his first kiss. I’m totally OK with being his first of many things, as he and I are in love and very happy together.

Here’s my predicament: we’re now six months into our relationship and we haven’t had any sexual contact beyond kissing. I would really like to move in the direction of sex, but I’m not sure how to proceed. I’m not lacking in sexual experience, but I’ve never had to make the first move. I’m 99.9% sure that he’s a virgin, and I don’t want to freak him out, but at the same time, we’re adults in a loving relationship and sex shouldn’t be a difficult topic of discussion. He’s shy and awkward, but I love him dearly, and I want to handle this in the best way possible because I hope to be with him for a very long time. — Ready for More

117 Comments

  1. It sounds like a nice relationship, and it’d be refreshing to be with someone who’s a little shy, I think. I seriously doubt that a 28-year-old man, virgin or not, is going to be freaked out because you make a move. It may be new to him and it may be awkward, but that doesn’t mean that he doesn’t want to. You know him best, so you should determine whether it would be better to talk about things first or to make a move In any relationship, though, moving past kissing usually isn’t a huge gesture — it starts little by little until you end up in bed together.

    1. Oops. 27-year-old man. Not that it changes anything.

  2. lovingmykids says:

    Just go for it!!! It’s obvious he isn’t going to make the first move, its up to you to take the bull by the horns! 😉
    On a serious note, it wouldn’t hurt to have a conversation with him about this. Is there a chance religious or personal beliefs are the reason he hasn’t made a move? It’s something you should know, and if you plan to stay with this guy you need to learn to communicate with him! My guess is he’s just shy & scared….. in that case, go get yourself some, girl!

  3. Just rip the band-aid off.

    “Hey, you want a blow job?”

    I donno, that usually works for me. But really, if he’s a shy person and treats you with a ton of respect, he probably doesn’t want to feel he’s pressuring you or disrespecting you by trying to take things further. That, and if he’s as inexperienced as you say he is, he probably just doesn’t know what he’s doing. You’re going to have to take the lead or nothing is ever going to happen.

    1. Too much, too fast! I bet that would freak him out. I’d move a little more slowly but still definitely make the first move.

      1. Actually, I think it’s a great way to bring it up. I think it would break the ice and get him to talk about things. I’m not saying she should jump on him and start blowing him, I’m saying she should just *say* it as a segway to talking about it.

        “Hey, you want a blow job?”
        “Ah, err. What? Really?”
        “I’m just messing around, relax. But really, what do you think about taking things to the next level sexually? Have you thought about it?”

        That way she’s not approaching him like he has some sort of problem and getting all ‘serious tone, your 27, is there something wrong with you’ on him. That’s all I meant by ripping the band-aid off. Just come out with it and start talking about it, rather than trying to drop subtle clues or hints or something.

      2. Alternatively, she could just start the conversation with “What do you think about taking things to the next level sexually? Have you thought about it?” and not make the conversation start out super awkwardly. These are grown ass adults, they should be able to speak to each other without the added “humor” of saying the word “blowjob.”

      3. Yeah, what B said. Jesus guys, calm down.

      4. Yeah, lighthearted might work on a guy who isn’t already uncomfortable with sex stuff, though. This would be a terrifying approach and would likely leave him super flustered.

      5. Well, the LW doesn’t claim he is uncomfortable with sex stuff, just that he is inexperienced. That inexperience could be due to many things, not just with being too uncomfortable. Just because he’s a virgin doesn’t mean he lacks a sense of humor.

      6. No, but being painfully shy means that he likely gets uncomfortable in situations that are new to him.

      7. The whole topic of sex will make him uncomfortable, breaking the ice with a half-serious joke a out a blow job will not send him running for the hills. .

      8. I sincerely doubt you’ve dealt with someone who is so uncomfortable and shy with sex that they are in their late 20s and have spent six months ONLY kissing.

        If they can’t get past kissing, I think opening with “So, do you want a blowjob?” would make him clam up so fast it’d make the LW’s head spin.

      9. light-hearted humor makes the world a better place.

  4. You could have a discussion about where you want this relationship to go – ask him if he’d like to get your relationship into physical territory. You could also, in the midst of your private kissing, take his hand and place it somewhere on your body you would like him to touch – under your bra, between your legs, whatever and where ever. When I took the viriginity of one of my boyfriends, we talked about it beforehand before I became the teacher and he was the hands-on student. I personally don’t want to participate in experiences that I’m not willing to talk about with a worthy partner, and if you have the same philosophy, then get talking.

    BTW, your guy sounds like a sweetheart! I’m sure he’ll be more than open to discussion. Good luck!

    1. Or, instead of taking his hand and putting it there, why not use your hands? If he’s that shy I wouldn’t start with anything too sexual… you could just put one of your hands on his chest, and start rubbing it. Then slowly move lower and see how he reacts.

  5. Talk first. Are you sure he’s shy, and that there’s no other reason he’s not making a move? Also, if he’s still afraid to approach you physically after six months (assuming the only reason he hasn’t done so is anxiety), I’d be a little concerned his shyness would stand in the way of honest communication on other matters, too. Is he anxious in other areas? Does he have a history of not speaking up when he should? Is there anything in his past, culture or upbringing that would make sex taboo, difficult, immoral, whatever? When you’re kissing, is he eager or reticent?

    If this is the one area he’s not so deft in, and if that’s solely a matter of lack of experience, then ask if he’d mind if you, ah, took the reins until nature took it’s course. But if he’s this shy, expect he will need practice and maybe a little extra guidance.

  6. I think you need to talk to him before you just start making a ton of moves on him. He might enjoy having the pressure off him by you taking control, but he might not. Do you know if he’s planning on waiting until marraige to have sex? If you aren’t sure, you might want to find this out before you try moving forward with him.

    If he’s open to moving forward physically, but is just scared/nervous, then I say, sure, take control and move things along, but do it sloooooowly. You don’t want to freak him out!

  7. My cranky morning advice is to grow up and talk to him about this. You’re an adult in a “loving relationship”. Part of a loving relationship is to be able to communicate about the basics.

    1. lexington says:

      Seconded! Why would you want to be in a relationship where you couldn’t talk honestly?

  8. AliceInDairyland says:

    I kind of had a boyfriend like that… although we were 17 not 27, so a bit of a different context but same situation. He was painfully shy, and almost painfully respectful of my boundaries (something I really appreciate now in retrospect). I have a few suggestions, but really open conversation in general cannot hurt and can only help the situation.

    1) Sometime when you are kissing, say something like… “I think it would be really sexy if you X” X could be… kissed my neck, and/or kissed my chest, and/or took my shirt off…. You can kind of build off of this. That way, he has a clear idea of what you want (and won’t be afraid of doing something you don’t want, and his shyness can be somewhat helped along by straight up (but sexy!) instructions)

    2) Another time when you are kissing, say something like… “Would you like it if I Y?” Again, Y could be… kissed your neck, kissed your chest, went down on you, put my hand here…. And again, start simple and build up. That way he knows YOU are interested in doing more, but he can still be in the lead because you are suggesting and asking a question. All he has to do is nod or say Yes, but then you know he feels comfortable and consent always gets 2 thumbs up from me.

    And although the first time you say this… it might seem awkward and not super sexy. But I PROMISE you, the right eye contact and tone of voice can really turn it into something sweet and steamy. This slow building up would also let you see if maybe there is some physical problem that has caused him to not more forward (not getting aroused, etc). Not saying it is at all, but it would be a good way to bridge the gap between where you are and where you want to be, and gather lots of clues about what your guy likes. And let him know what you like! That way, when you get “all the way” (whatever that really means) you will both have a toolbox full of tricks to pull out.

    GOOD LUCK. Send us an update!

    1. sweetleaf says:

      Woo! Your response just totally turned me on so it’s definitely gonna work for him!

      1. AliceInDairyland says:

        …And I didn’t even include the suggestive eyebrow-raising that can be added in 😉 And wear your sexiest bra when you decide to go for it! Nothing makes me feel more confident then wearing my favorite bra.

  9. I think you are putting the cart before the horse, dear LW. Emotional intimacy and the honest communication needed to be open and vulnerable with each other are still lacking in your 6-month relationship. If the two of you were really talking, you would know whether or not you were his first kiss or if he’s a virgin or what his thoughts are on taking the next physical step. And he would know your thoughts, wishes, and desires. Maybe both of you are a bit shy and awkward, yes?
    Consider that sex often doesn’t clarify things, rather makes them a lot more complicated, so before you put your sex-action-plan into motion do some work on the communication. Investing a little more time to get that right would be well worth it to achieve the long, loving relationship you’re hoping for.

  10. Ask him about it – a “pre-game” discussion may help make him feel comfortable and I bet after you do your thing one or a few times he will start to get the hang of it. Reassurance / positive reinforcement should help him come out of his shell a lot faster. As you begin to trust each other more you can start showing him more advanced techniques.

    1. TheOtherMe says:

      Is it wrong that I read “thrust” each other & got turned on ? Oups !

  11. Step one: make-out for a little bit to get him riled up
    Step two: ask him if he wants to stop or continue further

    Note: A glass of wine before hand may help ease nerves

    1. TheOtherMe says:

      1) Agree.
      2) No asking… go with your instinct

      Note: Agreeeeee !!

    2. I disagree with this tactic…he probably needs to know where to put it…and he has a 50% chance of getting it wrong.

      1. Also…wine, if he has anxiety, might make his boner a no-show.

      2. TheOtherMe says:

        1) Wrong ? well… that’s debatable
        2) After one glass only ? remind me to stock up on non-alcoholic wine

      3. haha true….but for most women that is a forbidden orifice…and I just thought I’d teasingly try and help the LW avoid an uncomfortable situation.

      4. silver_dragon_girl says:

        Just wanted to point out that it’s REALLY difficult to “get it wrong” without someone noticing and, um, helping to adjust.

      5. TheOtherMe says:

        Unless someone “pretends” to not notice 😉

      6. silver_dragon_girl says:

        Lol. Well, then it wouldn’t be a problem, would it?
        Just saying that, as a girl, if a guy gets near the wrong area without explicit permission, he’s going to be quickly corrected 😛

      7. TheOtherMe says:

        Haha @ SDG, When you say: “explicit permission” do you sign some sort of waiver ?

      8. silver_dragon_girl says:

        Yes. Notarized.

      9. You guys got me…I will attempt a more fool proof joke next time 😛

  12. I have a cousin like him. He is too painfully shy to make the first move about everything, and totally feels more comfortable with the girl doing it. Obviously my cousin and I talk about everything, so I told him let her know that you are just not comfortable doing this and when she is ready, to have her make the first move. And his current GF is just fine and happy with that. They have been together for 8 months, known each other most of their lives, and it is working out great for them. Truth is, NOT all guys are that straight foward…. make the first move and see what happens!

  13. TheOtherMe says:

    Well, I think that you just have to not “expect” it and just let it happen. I’ve had first times where there was hours of kissing before anything went further… and then it went further, naturally, and it was spectacular. Not sure if they need to actually agree on “ok, let’s have sex now” because it kind of kills the moment. Consider it like 6 months of foreplay. yum !

    1. I agree that she should let it progress naturally. A discussion about sex is going to cause anxiety in a painfully shy and inexperienced guy, plus it ruins the momentum and intensity of the moment.

      She should have condoms available, because he likely won’t have any.

      1. TheOtherMe says:

        Yes. But no Magnums, the guy’s already going to have performance anxiety !

      2. Well, she doesn’t know – maybe he does need Magnums! Just in case he doesn’t, she should have some rubber bands handy.

      3. TheOtherMe says:

        Maybe. But just in case, she should have the regular ones available too !

      4. I took a guy’s v-card once and I WISH we had magnums. He had no idea about size (he was comparing himself to porn stars – which is never a fair comparison) and couldn’t get the regular one he had on without it cutting off his circulation. We had to stop and try again another time… so, ‘moral’ of the story is to have a variety available! Just don’t show him the magnums until after you’ve seen the goods…

      5. silver_dragon_girl says:

        I feel like keeping Magnums on hand would be tempting fate to ensure that I am never, EVER with a guy who needs Magnums. 😛

      6. I thought those ones were only made to put over the top of your head and blow up like a balloon?

  14. Being one that doesn’t usually ever make the first move in initiating sex (in a 2 year relationship now) my boyfriend said that he would like it if I would initiate every now and then. When my coy ways weren’t cluing him in, I finally asked, “What could I do so that you would know that I’m initiating? You don’t pick up on my signals!”

    To which he replied, “Just grab my penis. That always works.”

    So, start with a rub while kissing.. see how he reacts.

    1. @Va
      Maybe it’s just because this is a sex-related topic, but I read your screen name as “va-ji-na.”

      >__<

      1. TheOtherMe says:

        Best.Thread.Ever. I’m not going anywhere else today =)

      2. me too, don’t worry

    2. I said this in another thread recently…that’s really all it takes – even if you make a joke out of it.

  15. I say ask him if this is what he wants to do, make sure you’re both on the same page, and then show him how it’s done. Be kind and loving, which I’m sure you are, and “rip the band aid off” as the commenter above said. He’s probably SO nervous to make the first move since he’s probably a bit inexperienced, and having you take that pressure off might be just what he needs to gain a bit of confidence. Either way, sounds like you found a great guy, and I hope everything works out for you!

  16. You can definitely ramp up the intimacy slowly with the moves others have suggested. You may not need a deep conversation before you try something just a little more than what you’ve been doing–that’s up to you. But when you actually get to the sex-level stuff, you do need to talk beforehand. At the very least, your conversation needs to cover protection and contraception. If he’s not very experienced, he may or may not be knowledgeable about and comfortable discussing these issues. He may make assumptions that shouldn’t be made. So take charge of the conversation to make sure your sexy time is safe for everyone.

    By the way, kudos on taking the time to develop what sounds like a fulfilling and healthy relationship. Your care for him really shows. I’m sure he’s been thinking about, and maybe even stressing about, moving to the next level and what your expectations are. You get huge props in my book for respecting his pace and showing that your relationship is about so much more than sex. I’m sure that will ease his anxiety a lot because he knows you care about him and are with him for so many more reasons.

  17. As someone who has dealt with an extremely shy and inexperienced guy before, you’re likely going to have to be the one to initiate each new “step”. I think it’ll make him more uncomfortable to talk about it beforehand, so just make it a natural progression of what you’re doing. As you move forward with new things, he’ll get more comfortable with the sexual acts, and he’ll start to initiate on his own up to the point that you’ve taken it thus far. But again, you’ll need to initiate each new “step” to take it further. 

  18. I’m in the camp that she should discuss it with him first. If they’ve been dating for six months and he has yet to make a move, that could mean a lot of things, so taking the bull by the horns (which is normally a great way to go about getting you want, and I don’t mean that sarcastically) might not be the best way to go about it.

    LW, just have a discussion with him about it like adults. He might be shy, but if the relationship is as loving as you say, then he will open up. Healthy dialogue. 🙂

    1. I agree completely. My bf and I have had a few discussions about sex and how we’re not having just it yet but are getting pretty close. Those conversations are always a little awkward as neither of us has much experience- (I’ve never, he has but isn’t super experienced) but we’re adults, and we get through it. And you know what? It helps a lot knowing how he’s feeling about it and all, and getting what I’m feeling out in the open. Awkward schmawkward, the peace of mind after the conversation is well worth the red face and stammering during it. (Maybe that just happens to me…dunno.)

  19. He sounds like a very sweet guy. You should def. talk to him, he´s probably insecure bout the fact that he´s a virgin. Just reassure him a lot when you´re cuddling or kissing. Also, a tickle fight does wonders for going further. It takes his mind of the whole, OMG, where do I put my hands thing, and can easily turn into something more steamy. Basically, make him feel comfortable with touching you and be intimate even in a nonsexual way. Also, if he does tell you that he´s a virgin, the best answer would be; so what? and then kiss him. Worked wonders for my ex, who was very grateful I didn´t make a big deal out of him being a virgin.

  20. To those females in the thread who want the LW to talk it out with shy-a labeouf here, let me suggest that 80-90% of communication is non-verbal and when it comes to getting it on, actions and tone matter far more. For the love of gawd woman, don’t talk about it!

    Now, if he re-beouf’s your completely unambiguous advances (see advice from va-in-ny’s bf), you’ll have something different ‘on your hands’ that your mouth can only solve by Talking. Then, you need to be very persistent, but real gentle like in your drawing him out. You know what I mean. If he won’t probe you, you have to probe him, with questions basically. Until then, jump up on it, grab it like you want it… Be aggressive, B-e A-g-g-r-e-s-s-i-v-e.

    I agree with the comment from Budg about wine hurting performance in general, but if this guy’s never been effed, it’s gonna take an oil tanker of alcohol to hold that woody down. No, in this case, a moderate dose (2 drinks) of alcohol is just the right prescription for these love birds. Plus then he might last more than a nano-second. :-/

    1. Yup. I completely agree. Guys are pretty straightforward about that stuff. Just start rubbing him down while you’re making out and head south. He’ll let you know if you’re going too far just by moving your hand. If he moves your hand after six months of dating, well, then you need to have a talk.

    2. Idk…if he hasn’t done it before and is the nervous type his weiner may be like one of those car sale inflatable banners on a still day if she doesn’t do it right. haha.

      1. If she goes straight from “just kissing” to intercourse, I think he’ll be extremely anxious. If she gives him a hand job, he’ll likely reciprocate shortly thereafter with manually stimulating her. Same with oral sex.

        She should take it a bit slow to make sure that he’s comfortable before moving to the next sex act. I realize it’s frustratingly slow, but if they’ve only kissed for five months, she’s obviously shown she has some patience.

      2. Of course PFG (what’s that stand for?). You’ve got it perfect in your other comment. I’m talking about the big picture. When I say aggressive I don’t mean to skip acts I through IV of the play and just go to the climax. Just to be goal-oriented and undeterred. Step-wise, by all means. Even if it takes several sessions. You’re totally right.

        And Budg good point. I was being a wee bit overt to make a point. That if he’s tentative, alcohol does magic to inhibitions that no words can do. Not everyone reacts to it that way. Heh, inflatatable.

      3. Haha I get your point…I’m sure if he steers clear of vodka redbulls then he should be fine.

      4. TheOtherMe says:

        I don’t know if she should let him reciprocate or guide him otherwise she might wind up with the George Costanza knuckle move !

      5. TheOtherMe says:

        Oups, reply meant for PGF

      6. All women are different – the knuckle move is quite effective on me! 😉

      7. TheOtherMe says:

        I prefer the octopus.

      8. It’s not really an “either/or”, is it? 😉

  21. I still like Dennis’ advice from an old “His Take” column:

    It may be geared towards a woman seducing another woman, but I think it still applies!

  22. Obviously, I don’t know this guy or what’s going through his head, but if I had to guess at what’s holding him back from putting the moves on you it’s fear of offending you or doing the wrong thing.

    You don’t say if your “kissing” is chaste kisses on the lips or full-on, hot-and-heavy make-out sessions, but it seems like the latter is a great place to start. French kiss him! Climb onto his lap (clothes still on)! Rub your hands over his chest! And if he doesn’t take the hint and do the same, GRAB HIS HANDS AND PUT THEM ON YOU! My guess is that once you show him exactly what you want him to do, he won’t have any trouble doing it. Don’t forget to be encouraging! In the moment, tell him “that feels good” or “I like that”, and afterwards you can check in with him to see how he felt about that and let him know that that behavior is now on the table and you encourage him to initiate it.

    Another thing to consider is the fact that you may have never made the first move before, but you’ve had first moves made on you. It might feel odd at first, but you might have to “be the guy” here. It sounds like this guy is worth it! And once you do get comfortable physically and can talk about sex together, things will get a lot easier.

  23. Can I just say that I’m very proud that we’ve made it this far in comments without one “Maybe he’s gay!!!” comment.

    I feel like we’re really maturing as a site.

    1. Britannia says:

      I’ve been scrolling down waiting for BGM to mention the possibility.

      1. I just clicked on your name – what is that awesome statue on the water?

      2. I just clicked on your name – are you a fan or in the band?

      3. TheOtherMe says:

        Mine is only clickable when I am logged in to “Musings on Life and Love” ??

      4. in the band…almost done recording our album – should be done this fall!

      5. TheOtherMe says:

        What kind of music ???????????????

      6. I would say you just got a girl boner, but I’d probably get a million thumbs down for that! 😉

      7. TheOtherMe says:

        ME ???

      8. You like music, and he’s a musician!

      9. TheOtherMe says:

        I am in fact musically obsessed, you know me too well PFG

      10. TheOtherMe says:

        My weekly musical obsession is The XX, just sayin’

      11. Actually, happy _very_ belated birthday. 🙂

      12. TheOtherMe says:

        Who, moi ?????

      13. Oui!

      14. TheOtherMe says:

        Grazie cara ! I think we have close B-days if I remember correctly … so HB to you too !!!!

        PS sorry to the LW for going off on a separate conversation, I tend to do that often

      15. Well, I’d thank you, but I stopped having birthdays a few years ago. 😉

      16. TheOtherMe says:

        We just took over the whole thread !

      17. alternative-ish rock

      18. Also…we are on facebook…I have both links on my name…I have like 3 computers at work which is how I can post often so I’m not sure which comment has what, but facebook.com/underwatertigermusic if you are interested.

      19. And…which one is you?

      20. Anthony – long haired one in the video gray shirt…I got quite the farmers sun burn just in time for the vid.

      21. If on the indiegogo page.

      22. Oh man, now I have an e-crush on you!! I can’t tell if you’re on the far right or far left in black and white picture (on FB and in the video).

      23. TheOtherMe says:

        I think you scared Budjer away with your e-crush and girl-boner comments PFG 😀

      24. Ha! I was just thinking that, too!!!

        Don’t worry, Budjer!

      25. No, Haha. I think I got spammed out…but far left.

      26. Britannia says:

        The statue of “Appennino” (1579-1580), a colossal sculpture by Giambologna. At Villa Pratolino, Tuscany, Italy.

      27. bittergaymark says:

        Well, there was a time when I used to date women and never made the first move either. Heck, I never made ANY move whatsoever… Go on and see it you can all connect the dots here…

      28. bittergaymark says:

        Actually, it’s a valid possibility. I can’t tell you how many times in LA I predicted a girlfriend’s new guy was actually gay and was right. No, wait, come to think of it, I can… Five times. It happened FIVE times!

  24. LW, in reading your letter, I feel like I’m reading about myself. I was in a relationship with a 26 year old virgin who had trouble initiating physical intimacy. In our case, we never got beyond kissing as well. We too had started out as friends, seeing each other in social situations, and then started dating. He was the most thoughtful, sweet, respectful guy. He was upfront with me about his lack of experience, but it was killing me inside that we never went beyond kissing. I felt like we were in high school, not adults in our mid twenties. I would sleep over in his bed and he wouldn’t try anything.
    So I talked to him about it. We had several talks about it. He would always say he wanted to “take it to the next level.” But he never did.
    I realize I could have been the one to take the bull by the horns and initiate sex with him, but I never did because I knew that if we did have sex and we broke up it would really hurt him. I put pressure on myself being his “first” because I knew it was something he’d never forget and find very important. I couldn’t live with the guilt of taking his virginity and not being the woman he ultimately ended up with.
    But your situation is slightly different. You say you are really in love with this guy. You want a long future with him. I assume you’re physically attracted. So take the bull by the horns with him. Next time you’re making out, guide his hands certain places, let it progress. If he doesn’t take a the hint, you’ll really have to talk to him about it. And if he doesn’t respond after you make physical advances and you talk about, there’s not much more you can do.

  25. silver_dragon_girl says:

    Can I just say that this whole thread reminds me of the episode of Friends where Rachel can’t stop laughing while kissing Ross, and then he says he’s not in the mood, so she tries to get him to put his hands on her butt by saying, “Well, you just stand there and I’ll back into you?”

    Also the one with Monica and the high school boy (only due to the “taking” his virginity aspect).

  26. GenaBoBena says:

    If you can’t talk about sex with him, then you probably shouldn’t be having sex with him.

  27. ReginaRey says:

    I’m so torn on this one. He’s obviously waiting for you to do something – whether that’s talk about it first or just jumping right in. I’d recommend talking to him first, but in context. Don’t just ask him over dinner, “So, do you want to have sex with me in the near future?” I say – slowly build up to traveling to the nether regions during a makeout session. You can ask him seductively “is this ok?” and if he doesn’t protest, go for it! Maybe a few of these sessions before the main event. Of course, if he protests or looks extremely panicked, set aside the penis and have a discussion. Test the waters slowly and see where this goes!

  28. I think you need to have a conversation with him before putting your hands on him or placing his hands on you. Don’t assume that the reason he isn’t going to the next level is because he is shy. Consider what his beliefs and values might be. He might be religious or just plain old fashioned. Also consider if you would be okay with this as well. You need to be open, kind, loving and understanding when you have this conversation with him. Realize that even if he does want to have sex, he will have a lot of anxiety. Maybe you won’t be able to complete the act the first time. Be aware of his feelings. Communication is the key. I agree with the above posters that if you can’t even talk about it, you shouldn’t be doing it. Don’t ever assume anything. He may not want to have sex yet or at any time until he’s married. You don’t know until you talk about it.

  29. Letter Writer says:

    I wrote this letter, so I want to clarify a few things-
    1. I really like the wine suggestion. I’m a boozer myself, but my boyfriend doesn’t drink at all. And I don’t want to be the drunk woman with the merlot mustache sticking my hand down my sober man’s pants. le sigh.
    2. I’m a little shy myself, so I’m having some trepidations about making a brazen move, or saying “hey, want a blowjob?”. I think having a talk about it may be the way to go.
    3. We do a lot of super hot making out, how this doesn’t progress to my top coming off, I’m not sure.
    Either way, I have a rare kind of guy on my hands, and I don’t want to let him get away. I really think he doesn’t want to disrespect me, offend me, or appear crass. You guys are right, I need to have a talk with him, get over my own anxieties, and be an adult about this.

    1. Thanks for the comment, LW! I wish you luck, and as I mentioned above, I’ve been in your situation before, and being too forward with him (“Hey, do you want a blow job?”) is going to overwhelm him. I’d do what you know you’d both be comfortable with, and I think it’ll all turn out wonderfully! 🙂

      Please update us later!

    2. Betty Boop says:

      Having deflowered a 27 year old virgin myself, you need do need to just talk to him. Easy time brooch the subject when you’ve been smooching it up and just say something about how much you want to do more. I just told my boy that I really wanted to sleep with him and how did he feel about that. It proceeded with a little bit of conversation and a whole lot of action. Your guy probably hasn’t made a move because has no idea how things naturally progress seeing as he’d never had a second date before. He’s never going to learn if you don’t take the situation in hand by (wait for it)….talking to him!

    3. Britannia says:

      Perhaps you could this:

      During one of those makeout sessions, start pulling your shirt off. If he allows it to happen, you’ll have progressed to a new level without forcing him to do anything, and if he asks you to keep your shirt on, at least you haven’t made it super embarrassing for both of you by trying to take HIS shirt off.

    4. your making out doesn’t go into anything else most likely because he either doesnt know that he should be doing that, or he is very afraid to try to take YOUR top off. i think you just need to nudge him a little bit in the right direction… i mean he is human, he will understand, he will get it… we all have the instinct to have sex, he just needs little nudges and hints that this is an OK situation to do it in.

    5. Hmmm….

      Is there any chance his beliefs might be getting in the way? Did you ever talk about sex before marriage with him?

  30. I’d also like to say, YOU’VE BEEN DATING HIM SIX MONTHS AND YOU DON’T KNOW IF HE’S A VIRGIN!?!

    You two seriously need to have this conversation ASAP!! Maybe you’ll be shocked to find out he’s not a virgin, because it’s never the ones you expect. But then again I’ll assume you’re right and that he is still a virgin. Which I imagine makes you think he’s to awkward to have this conversation, or maybe the idea of having this conversation is awkward you. I dont blame you, because once you know for sure he is a virgin, there’s no way to unknow. And yeah, honestly, as an experienced sexual woman, getting it on with a virgin probably isnt your cup of tea, but hey it’s not most peoples either. Regardless, I understand why him being a virgin also sums t be an issue, hello to getting to set the bar. Hopefully, even if you two so break-up, he’ll forever remember you as the best lay he ever had, or maybe his only lay he’ll ever had, and that’s not a bad hung either!

    Regardless! Regardless! You seriously need to talk to him if any of those scenerious are to happen. And if you think that’s awkward, wait till you have to discuss birth-control…

    1. Wrote that on my iPod, hello typos!

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