He said he'd wait, but he won't stop asking.
Heather Corinna replies:
I'm a 17 year old girl and have been dating this guy for a year and a half. I love him and know he loves me. For about the past six months I've been giving him handjobs. We started out slowly. (Through his pants, though his boxers, and then of course through nothing.) Well, recently he has been trying to convince me to let him fingering me. I told him "no" and he was pretty respectful of that. Each time we do something though, he asks for it. When I say no, he keeps saying 'okay, I'll wait for you" When he kept asking, I said wait till I'm in college and we'll see. Then, he said okay again. Once he asked me why I wasn't ready and I said because I was scared. When I couldn't explain why I was scared he got a little frustrated. He still keeps asking me for fingering and as I say no, he says "It's okay I'll wait for you." I just want to know though, how I can get him to stop asking, it kind of feels like he is pressuring me. I've tried to find a reason for my fears, but I can't place my finger on it other than I'm not ready. (It doesn't help that an old of crush of his- who is both of our friend- is telling him about how her boyfriend gave her first orgasm through fingering.)
No one ever needs a reason to say no to anything, just like you don't need a reason to say yes to something.
It sounds to me like you have been very clear when it comes to what you do not want to do. You even put a very clear date on it, so since you said that it won't happen until you're at least in college, unless you have started college, he shouldn't be asking.
He keeps telling you he'll wait for you, but he's not really waiting for you at all since he keeps on pushing this.
However, it also sounds to me like either he figures if he just keeps asking, you'll eventually cave in, or -- more optimistically -- like he doesn't understand how to respond when someone says no. It's understandable you feel pressured, because whether he intends it or not, you've been pressured.
When someone really wants something -- sexual or otherwise -- they will tend to pipe up, not tend to just eventually say yes because the other person keeps asking. Consent is sometimes about someone asking for something, and the other person clearly saying yes in response, but when it's really wanted by both, it's also often not just about one person being the constant initiator. Rather, people's shared want of the same thing, while it should still be verified, is often self-evident. Even without words, if you haven't made any motions yourself like, say, moving his hand further into your pants when he has had it there, or haven't asked for that yourself, he should be aware already it's probably not something you want.
Ideally, the way a partner should respond to a no is by completely accepting a no.
If they knew it was something they really wanted, and it was only about you not wanting it, they could also respectfully say, "I respect that and want to respect that, but I am interested myself, so if you change your mind, could you just let me know?" In other words, he can voice his wants, but since you have said no, he needs to leave the ball (as it were) in your court, without revisiting the subject unless you put it on the table. After all, you're both aware of what he wants, obviously: it's not like he was unclear, either. Plus, were he to change his mind and decide he doesn't want that either, he can always fill you in on that change.
Like I said, you don't need a reason to say no, and he shouldn't need a reason to accept it. Whatever your reason is should be reason enough. Now, if he's just curious and wants to know, or wants to know to better understand you, it's okay to ask, though that's a conversation for out of bed, not in it or while making out. Having those kinds of conversations in the midst of any kind of sex, or what might be leading up to any kind of sex, is not the best environment when it comes to everyone really feeling emotionally safe, calm and level-headed. If we have those kinds of questions in bed, what tends to work best is to make a mental note of them, then a day or so later, ask a partner if we can talk to them about those questions when we're just hanging out, having lunch or coffee or taking a walk.
He also needs to accept that if you know what you do and don't want, but just can't articulate clearly why, that's out of your control. It might be helpful if he's frustrated by that to remind him that it's just as frustrating -- if not more so -- to be the person who can't fully understand something about themselves as it is to be the person who can't fully understand someone else.
How do you get him to stop asking? You tell him very clearly that he needs to stop asking. Like, yesterday. And again, this is a conversation best to have before you two get intimate again, not when your hand is in his pants.
You might say something like, "I need you to stop asking about the kinds of sex I have made clear I am not okay with doing now. To be clear again, those are [whatever those are], and I have made clear I do not currently feel I will be ready for those until I'm at least in college. If and when those are things I want and feel ready for, or if I happen to change my mind, I will absolutely let you know. But until then, you need to stop bringing it up, because I am feeling very pressured by you, and that isn't okay."
You might also want to add something like, "By the way, I hope that what you want in any kind of sex we do or ever have together is sex where both of us really want it to happen, not sex where one of us wants it and the other caves in to something we don't want because of pressure or because we feel obligated. In order to avoid that, it's really important you stop asking me about this, okay?"
Something else to consider, especially if you say things like that and he still keeps pushing, is if it's a good idea for you right now to be engaging in any sexual activities with this person.
It's absolutely okay for you to feel okay about giving him handjobs, but not having him do the same for you: doing what you're doing with him certainly doesn't mean you're somehow obligated to be on the receiving end yourself or that you must feel ready for that. But not everyone understands that, especially people who are new to sexual partnership and sexual relationships. You can certainly ask if he understands that, but if he says he does but still behaves the same way, it may be that he doesn't, even if he says he does.
As well, it's often tougher to stick to your guns in terms of firm sexual limits and boundaries if you are engaging in some kinds of sex with someone. For some people, or in some relationships, when there are strong limits on what's okay to do and what isn't, it can work better to simply step away from intimate contact altogether, or at least from anything besides kissing and hugging, or activities where everyone's clothes stay on and everyone's pants stay buttoned.
When you're in the thick of something sexual, saying no can be harder to do, and for some people, especially for anyone who still has some maturity to gain, hearing no can be harder, too. In a best-case scenario, that's something that person having a tough time hearing no would recognize about themselves, and choose to step back from sex knowing they need to work on that first, but that's another issue of maturity. Not everyone is at a point in their personal development where they're good at seeing where they need to do some work and seeing where they need to be setting limits.
Whether or not stepping back to a less sexual relationship altogether is what is right for the two of you, and makes all of this work better, is something you can talk about and work through together. You can even just try that and see how you feel about it, checking in with each other as you go.
One other thing you might want to talk about, when it comes to what his old crush told him, is that experiencing sexual pleasure from something doesn't necessarily (or often) change a person's values or what someone feels is best for them sexually. In other words, if he has the idea that fingering might result in orgasm for you, so you'd be okay with it, he's probably incorrect in that assumption. Not only is you reaching orgasm from that the first time out unlikely, you having an orgasm then somehow turning into a totally different person who feels differently about all of this is not at all likely.
It may also be that you two need to talk about what he actually wants in being so eager to do this. It may be that he, as many people are, is turned on by his sexual partner being turned on, so however good what you have been doing for him feels, he may feel he's missing out on a pretty major part of any sexual activity, which is your enjoyment, especially if what you've been doing for him isn't something you appear to be that into. While there's often a lot of talk out there about how all men want out of sex is their own pleasure, that tends to be more stereotype than it is fact. Many men, just like many women and people of all genders, are very invested in their partner's pleasure. So, if what's been going on is really all about him and his body, that may emotionally and sexually feel halfway there for him.
It may be that he feels like you've been doing what you are for him to try and mollify him, too: to try and keep him satisfied enough to stick around, or to try and give him something so he won't ask for more. If he feels that way, that often really doesn't feel very good for people. There are other possibilities, but those are two biggies that come to mind.
That doesn't mean you need to change your mind about what you want and what is best for you: you don't, and you should still choose what it is that you are comfortable with and feel best about. But it may mean that a sexual relationship of any kind right now isn't such a great fit for you right now, or it may mean that you two want different things in this kind of relationship. So, these are all things to sit down and talk about together, to ask each other about, and to make some decisions around.
For the record, sometimes our readers in this kind of position feel very reluctant to say the kinds of things I'm suggesting you say, draw a firmer boundary, or take any kind of sex off the table wen it's not working for everyone for fear it'll mean their partner may then not want to stay with them anymore.
If you feel that way, I certainly understand being afraid of that, but at the same time, for a relationship to be a good one that works well, people need to want similar things. If you find out through your talks that you two really don't -- he wants a relationship that has a faster sexual pace than you do, or wants to do things badly you don't -- I'm of the mind that extending a relationship that's probably incompatible in any given way doesn't do anyone any favors. Instead, it can just tend to prolong the agony and leave one or both people feeling like they spent too much time in something when they could have moved forward and potentially found relationship that really did fit everyone's needs better.
If you two love each other, I can only assume what you both want most is for both of you to be happy. If being together is making, or in time does make, either or both of you very unhappy in a way you can't (or one of you doesn't want to) work out, you will want to consider if this relationship is still a good fit. Not all relationships endure well over the years, after all, especially romantic relationships when we're younger: they can often tend to change or get outgrown pretty fast sometimes, especially if the people involved are really different in some ways.
But do start by talking, and it sounds like you two probably need to have a few talks about all of these things. I'll leave you with both my best wishes and a few extra links that might help in your discussions and decision-making: