Is letting him cum inside me for his first sexual experience too much?

29 comments

1. I think you are asking all the right questions. The fact that you’re willing to be patent and work on his confidence is awesome.

   We can’t really say what sex acts you should do – I think you’ll have to play it by ear. But if you are protected and both of you are STD free, I don’t see why him finishing inside is a bad idea. To me, it’s easily the most intimate way for a guy to finish.

2. Defenitely the latter of the two. First off, I know with my first time, I was so excited that I busted almost instantly, and I was wearing protection. So odds are, he’ll probably find it more enjoyable if you do some other erotic things like playing with it and making him comfortable. Even tell him what you like about it, that should make him less nervous and more turned on I would think.

   If things do progress, I suggest wearing protection anyways, as those inserts aren’t 100% effective.

   On top of that, if you aren’t ready to get pregnant you should NEVER let a man finish inside, EVER. That’s literally the one thing that will get you pregnant. The risk just isn’t worth it if it is something you’re not ready for.

3. Sensation wise, it’s going to be better without a condom on.

   Intimacy wise, it’s better without a condom on.

   And enables a trick or two that condoms will complicate.

   For those reasons, it sounds fun.

   But is he ready for that? No one here will know. I think you are doing yourself a disfavour if you intend to rush things here.

   But if you head into it with the intention to have fun, instead of being goal oriented, it’ll be awesome.

   Remember, everything is new to him. It’s going to be just as new to him to have your hand in his pants as it is being in you.

   Except that the last bit is more of a desired goal, so to speak.

   But my point is that you are going to introduce him to a hundred new things. Some of them VERY exciting.

   If you focus on the one thing that is exciting, you forget that other things are important and exciting too.

   If the one exciting thing happens today, tomorrow or next week is not really important as long as meeting you is exciting.

   And from the sound of it, it most certainly is.

4. This is a good idea because you won’t have to worry that your boyfriend will lose his erection when you stop the action so he can put a condom on. He’s clearly very shy about anyone seeing his penis. A good way to address this if for both of you to undress and do something non-sexual like talking or watching Netflix. This will give him time to feel comfortable when he’s looking at your naked body and you’re looking at his naked body. It might take an hour or two before nudity becomes unremarkable.

   You could go straight to penis in vagina sex, or you could show him some sexual techniques before you have PIV sex. You could give him a blowjob and a hand job. You could teach him how to finger you and go down on you. This will help him to feel more comfortable having sex with you before you have PIV sex. The most important thing that you can do is to take your time. You could spend a weekend together so he won’t feel rushed to have his first time, and he has plenty of time to have more sex.

   You should read the r/sex FAQ section about penis size [https://www.reddit.com/r/sex/wiki/index/#wiki_penis_size](https://www.reddit.com/r/sex/wiki/index/#wiki_penis_size) It has a link to a very reassuring thread about penis size, It also has a link too a thread on what a partner can do to help. Your boyfriend should definitely read the thread discussing penis size. Your boyfriend should also read the FAQ section about having sex for the first time.

5. Are you ready for an unplanned pregnancy? Do you know how you or he would feel about an unplanned pregnancy?

   No birth control is a 100% guarantee so what you are planning is pretty risky, especially for his first time. You shouldn’t rely on him controlling his ejaculation and pulling out on the first time because you can’t know how sensitive he may or may not be.

   Legit reconsidered unless you’re both mature enough for this kind of scare.

6. Being his first time he’s most likely going to cum quickly so definitely let him finish inside.

7. 1. I would personally recommend wearing a condom always but honestly that your personal decision and of course it feels better without.
   2. Sex right away especially when he’s nervous might not be the right choice
   3. Getting him naked and just staring at him isn’t going to help lol.
   4. You want to make him comfortable with his dick out? Worship it. No sex. Maybe some light stroking, kissing, oral, licking, but be enthusiastic and don’t hold back, make him feel like you LOVE his penis so much that he can let go of his insecurities. For me personally when I know a girl loves me and my body (all of it, penis and all) it makes me a better lover, I’m more comfortable because I know she isn’t judging me, and that allows me to let go be focused on the sex instead of how I look/how I’m doing/is she happy. GIVE him a sexually safe place to make mistakes and find his groove.

8. Both of you can get naked. Tell him to lie on the bed. Then give him a blowjob and tell him he’s free to cum if he can and wants to. That should take all the pressure off him. If he can’t cum that’s okay too, but you gotta let him know that. He will probably cum quickly though. Then you can teach him how to go down on you. Guide him and tell him what you like. This should help him feel pretty comfortable. Tell him if he’s hard he can stick it in. If not y’all can try having sex after. I’m sure you guys are gonna have a ton of sex and it’s awesome you wanna guide him through his first time!

9. yeah. I think you have the right motive but a little off in some places. It maybe a bit ambitious. Understand the risks in going condomless even with a pill.

   Just make out and see where it goes. You can’t change body confidence over night which doesn’t work with the exposure therapy. Relax him. Give him compliments. Maybe let him explore you. He’s never seen a woman so maybe guide him. Don’t force his pants off but sort of ease him into it. Let him drive what he is comfortable with and it may not be PIV. If you are down to your underwear, maybe he is down to his. Slow it down.

   Teach him how to physically play and get loosened up. He’s going to have his learning curve and you have to opportunity to teach him how to be generous. Foreplay for right now and maybe after a few times he may say, I want to do that.

10. I did this with my boyfriend, who was also a virgin. It took a few tries for us to actually have sex because he’d get nervous and be unable to get hard. It took a few weeks for him to get comfortable being naked around each other, then more times after that before he could actually finish inside me when we had sex. I have an iud and we’ve never used condoms or had a pregnancy scare. Even now he doesn’t usually finish inside me, says it’s because he’s stressed about work and school and that’s a mental block that keep him from finishing from sex.

    Spend a few nights sleeping naked in the same bed and get comfortable with that level of intimacy, then move on to oral and sex.

11. Sounds like this will be a lot of fun! I think your “exposure therapy” is a good idea. Maybe wait a bit on full PiV sex for a while until you both have gotten used to each other’s bodies and he’s comfortable with it.

    Back when we were virgins, my partner and I started with over-the-clothes touching and grinding, then moved onto under the clothes touching, then naked, then oral, then sex. That progression may not be what you need, but it allowed us a long time to get used to sexual activities.

12. Why

13. Spend some time working with it. Get it in your hands with it right in your face and spend some time just rubbing his cock. Spend some time licking it, sucking it, let him know you like it. Build up his ego. If he cums quick, who cares??? He’s young… give him 5 minutes of pleasuring you and he should be right back up… butvyeah just take your time with him and make sure he understands that you really like.his dick and that there is nothing wrong with it. And when you are ready, climb on board or go for whatever position you feel most comfortable. If you are ok with his load.in you, that is completely up to you. Just be aware there is a risk to everything. Nothing is 100%. But I’m damn sure he would never.forget it

14. Well…ok. Actually I think I understand why your asking for advice, these are legit topics I think. Also I read some of the other responses and can’t say that I disagree with those either! Lol. Look… humans have been figuring out how to have sex since pretty much like 30mins after the beginning of time! Lol. Ya know? I’m sure you guys are going to be fine. The one thing that gives me pause is the shame of showing his penis for the first time… he’s got possibly a hangup from his past that still bothers him maybe. If so don’t try to pry it out of him, he will let you know in his own time. Reason I say that is surcumsized (misspelled I know, had to otherwise might be body shaming! Ugh) or not, why would he be ashamed of his penis unless it’s itsy bitsy teeny weenie, and by his measurement, it’s definitely not. Idk why, but not many guys are going to be even barely nervous about pulling that out, ya know? So I’m wondering if there’s anything else there… Everything else is really you guys decision not ours. Also your bodies, so if either one of you wants, or doesn’t want a condom or where you want him to finish is completely up to you two. I’ll say he’s very lucky to finish inside the first time, I had been having sex little over a year before I was allowed too! Condoms for us mostly ugh we both hated them, and pulling out sometimes. But we could both tell how much better it was bare that we didn’t want to spoil ourselves and we just only went bare when it was a situation that I just had to, or she just had to have me inside like NOW and didn’t have time for condoms lol. Those were the days…lol. Relax, I think everything is going to be great, and if you’re relaxed it’s going to definitely make him more relaxed. Be gentle with him first few times and then I bet your gonna have a tiger on your hands. Good luck! Not that your bf needs it!!! Lol

15. I think your best option would be asking him what he wants and agree to what you are comfortable with. He might prefer a condom for various reasons, who knows. Same about getting comfortable about his penis.

16. Don’t overthink this. Just go with the flow with him. The important thing is comfort for both of you. Focus on foreplay and get him used to that. It’s actually more rewarding than sex and he needs to learn the skills of pleasuring you as well. That way, you both find the experience wonderous.

17. Firstly I wouldn’t just sit there and stare at his member, that will make him feel awkward and might make his anxiety worse (may even have trouble keeping an erection at that point). Look at it by all means, maybe give him a couple compliments on his cock to ease his mind and boost the ego.

    As far as going condomless and cuming inside, that would be fantastic, but he needs to be on board with that, so maybe ask him before just expecting that to be ok in the moment.

18. You have a golden opportunity.

19. I think you’re thinking in the right direction! However I’d say that a stare down would be *terrifying* to me. I also think jumping to oral is a lot, too. I’d suggest starting with your hands. Get hotter with the making out, and do things like touch him *over* his pants. Then you can work up to sliding your hand into his pants, then taking off his pants but leaving his underwear on. He’s nervous about you *seeing* him, so I think starting with sight-unseen touch will feel more comfortable. You can guide him to do the same to you. Then take it from there if he’s comfortable!

20. There is no reason to rush things. Why jump straight to the finish line when you can take your time with other stuff and still her there eventually?

    You’ve never even seen his penis. He’s never had someone look at it before. Wjy not start with awesome handjobs? Or blow jobs? Spend a week on just blow jobs! Really revel in the good stuff along the way to PIV.

    There’s so much for both of you to experience. Is there something he can do that would be your “first”? You can learn together. Holding out on sex at first can ramp up the desire!

21. If he’s worried about being seen naked the last thing you want to do is look at it at all. Make sure he’s hard before you even touch it. Give him a hand job while your kissing him and make him cum. Tell him you want him to cum. Wherever his cum goes he won’t want to touch so make him cum without it interfering with what’s going to happen next. Make sure he knows that it’s ok if it’s quick. Have him finger you so he gets to know his way around he will think that he’s just giving you what you gave him. After you cum he should be hard again and ready for another round. Why is everyone worried about a condom? He’s a virgin you don’t have to worry about diseases. Keep us updated

22. Oh man, he might be more head over heels then ever if you let him fill you up. Be prepared to have this guy attached to you for a while. 5 min later … “can we do that again?” 🙂

23. I say stare at it then play with it and then suck on it and then have him cum in you.

24. If you want him to never want to wear a condom again in his life, then yes, it’s a fine idea

25. As long as youre both clean and free form STDs absolutely. Let him blow!

26. The one problem I see with letting him go raw the first time is that he’ll never want to use a condom. That’s what happened to me. I (64m) have been having sex for 49 years, with about a dozen different women all told, and never wore a condom, and apparently just got lucky, no STDs or pregnancies. I suppose I would use a condom if I were single again, but it would be difficult.

    I’m sure you don’t mean it literally, but giving his penis a “stare down” should be done tactfully and appreciatively. Make it clear to him that you love seeing it and think it’s good looking, soft or hard. He’s exactly average sized, so he may or may not be self conscious about size. Be very careful about that. But yes, it is a good idea to get him really comfortable with you seeing him naked.

    Yes, spend some time just gently touching it, and letting him touch you too. Don’t be in a hurry to do anything in particular, just enjoy one another. If it does end up in PIV (which seems pretty likely), great! He might only last three strokes, and that’s great too, let him know you’re there for him to try again (and again) later. Or he may not be able to get hard this time, and that’s fine too. This may be the most important point: whatever happens this first time, let him know that it’s only the beginning of something wonderful that will continue over time and get even better.

27. This is one of the sweetest posts I’ve seen on reddit. You’re a gem of a person I hope everything went well

28. Start by letting him do what his fantasy is. Don’t worry too much about where he wants to finish unless it’s something that you don’t want. But I think it’s a good opportunity to see what he’s into by letting him take the reins

29. Get naked and then do something like play ping pong for 20 minutes so he gets into a different, more relaxed, frame of mind.