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Being okay with lack of sexual history
Totes an alt
Registered User regular
Registered User regular
(Alt used because my boyfriend knows about my regular account but wouldn't read a relationship thread unless he knew I created it)
This isn't about me but my boyfriend. I'm 26 and he's 23 and we've been together for a little over 2 years. Before we met, he had never had a girlfriend and is not the type to go around having random sexual experiences so I was his first pretty much everything. It bothers me how much this bothers him sometimes. I feel like I'm not enough, like he resents me for being a good fit and not giving him an excuse to break up with me and meet someone else, and for having been fairly sexually adventurous myself for a few years before I met him.
I place value on honesty over monogamy and would actually really like to have another woman join us some time, but single bi girls who are down for a three way are called unicorns for a reason, so the search is going somewhat slowly. I would even be okay with him meeting someone and being with them without me as long as everyone knew what was going on, but he's very shy so going out and meeting a girl AND explaining to her that he's in a relationship but it's cool because I know about and am okay with everything would be very difficult for him.
Part of his problem is that most of our friends have histories more similar to mine than his and aren't shy about talking about them. This leaves him feeling left out of a lot of conversations and like a kind of freak afterwards, like he's missing this essential experience the rest of us have. I've never hidden my past but I haven't thrown it in his face either. I like to think that we have a good, satisfying sex life and that we communicate well but this really hurts me sometimes and I feel like a jerk bringing it up to him because I know he's entitled to his feelings. The thing is, I think he's blowing it out of proportion - it's really no big deal, he's in a good relationship now and I'm not even demanding that he choose between being with me or exploring other sexual avenues as long as he's honest. When I try to get that across, he tells me that I don't understand what it's like to be a 21 year old virgin (true but I don't know how relevant. I did my part, I cured him of that condition...).
How do I help him to be okay with this? Everything else is great but I'm tired of feeling like an obstacle to his happiness, or the happiness he assumes he'd have if only he knew what another vagina felt like.
This isn't about me but my boyfriend. I'm 26 and he's 23 and we've been together for a little over 2 years. Before we met, he had never had a girlfriend and is not the type to go around having random sexual experiences so I was his first pretty much everything. It bothers me how much this bothers him sometimes. I feel like I'm not enough, like he resents me for being a good fit and not giving him an excuse to break up with me and meet someone else, and for having been fairly sexually adventurous myself for a few years before I met him.
I place value on honesty over monogamy and would actually really like to have another woman join us some time, but single bi girls who are down for a three way are called unicorns for a reason, so the search is going somewhat slowly. I would even be okay with him meeting someone and being with them without me as long as everyone knew what was going on, but he's very shy so going out and meeting a girl AND explaining to her that he's in a relationship but it's cool because I know about and am okay with everything would be very difficult for him.
Part of his problem is that most of our friends have histories more similar to mine than his and aren't shy about talking about them. This leaves him feeling left out of a lot of conversations and like a kind of freak afterwards, like he's missing this essential experience the rest of us have. I've never hidden my past but I haven't thrown it in his face either. I like to think that we have a good, satisfying sex life and that we communicate well but this really hurts me sometimes and I feel like a jerk bringing it up to him because I know he's entitled to his feelings. The thing is, I think he's blowing it out of proportion - it's really no big deal, he's in a good relationship now and I'm not even demanding that he choose between being with me or exploring other sexual avenues as long as he's honest. When I try to get that across, he tells me that I don't understand what it's like to be a 21 year old virgin (true but I don't know how relevant. I did my part, I cured him of that condition...).
How do I help him to be okay with this? Everything else is great but I'm tired of feeling like an obstacle to his happiness, or the happiness he assumes he'd have if only he knew what another vagina felt like.
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Honestly though it sounds like it's him. Maybe don't talk about "curing him" of his virginity when he was 21. Not having had a lot of sex with a lot of people isn't the worst thing in the world and you don't want him to feel even worse about it than he already unjustifiably does.
So assuming you're giving us an accurate picture, I would suggest trying to stop feeling like an obstacle to his happiness because you're not an obstacle. You're like, the opposite of an obstacle. You're doing everything short of breaking up with him in terms of helping him with his "problem." If he still feels bad because he didn't sleep around enough in his youth that's not really your problem.
And he's only had one person ever give him that.
So, taken from that perspective, you can see how a strong, healthy relationship might feel like a "curse" - he's got no warrant to be further validated. While this might sound pretty juvenile (and, yeah....it really is), it can powerfully inflect self-image, and there's just not too much you can do to help him through it. It's his regret, and there's only so much you can expect to do to manage his attitude towards his past and his present self.
The other slightly more rational issue at work here could be that he is deeply uncertain whether or not what he feels is "real," by which I mean without point of contrast, he may not feel confident that his relationship really is very strong. You've had past relationships that have run their course. He doesn't have a basis on which to compare what he feels in this relationship - the only standard is itself. That, too, can be deeply unsettling. Perhaps the sexual adventure problem is really more a means of looking for an "out" of a relationship he can't fully come to terms with. And, with the issue of personal validation thrown into the mix, you can also see how the prospect of actually breaking up with you could be pretty terrifying - could he actually convince another woman to give him what you've given him? And so on. Sex notwithstanding, when you talk to him about the future, is he comfortable? Are you?
So, to sum up, it sounds like you've been immensely supportive of him, which is great, but if his perspective is anything like I suspect, you may simply not be in a position practically or emotionally to help him through this, and that isn't your fault. I hope this doesn't feel too much like non-advice, but I suspect the best thing you can do is remain supportive and as emotionally available as you can be, but do not place this on your shoulders if he is unable or unwilling to appreciate the relationship on its own terms.
Edit: and also having read the second post and subsequently Ceres' post...yeah, more detail would be helpful, so do disregard whatever of the above is patently irrelevant...I guess I assumed that this was a thing that he tends to bring up with some frequency.
I can understand feeling like he's "missed out" on certain experiences from time to time, but he's gotten to avoid the really soul-crushing negative ones, so far. It's great that you guys are in a relationship where you can talk about such things openly, but I think he needs to give his head a shake a bit, and be thankful for what he has, not pine after crappy stuff he got to avoid.
Tell him life is what he makes of it. Stuff doesn't have to happen inexplicably.
The former came up recently after we played a board game with friends called Pervert which is a never have I ever type of game. I won and he came in last. It wasn't my game or idea and he seemed to think it was really funny at the time but later it was clearly bothering him. He didn't learn anything new but having not only me but almost everyone else beat him by such a margin was kind of hard for him. Other times it will be when we're walking home from a night out. Most recently he left a gathering I missed because of work where according to him everyone was discussing their sexual histories and he felt so much like he had nothing to contribute that he just left. He said something along the lines of "I could handle it if only people would stop throwing it in my face".
Edd that wasn't non advice at all it's great thank you.
And saint2e I agree with you but saying so ends in being told I don't understand.
I'll have more to say when I'm not typing on my phone
I'm poly myself. I can tell you that unfortunately for him rampant insecurity doesn't look more attractive when you're in a relationship. Sometimes it will, but not to the right kind of people, and that's always the case. You're being very generous in allowing him to meet other people within the context of your relationship, but if he's too shy to meet anyone it's not going to help because he's never going to get to that point, and anyway I think it kind of misses the actual problem especially if he's not actually poly.
When you say you're cool with him meeting people even without you, are you talking about sex, or for a relationship? Here's the thing: you mentioned in your second post that this isn't just about sex. He's never had his heart broken, never had a failed relationship, etc. I was like this in high school. Sex is not going to give him those experiences. The only thing that will is having, for better or worse, a relationship that isn't you. In a serial monogamy context, that means breaking up with you and finding someone else. In a poly context, he could start a relationship... but if he's looking to experience pain AND keep you, he'll be setting up an entire relationship to fail. Or maybe he'll have two and be happy because keeping two is some hard work! And then he will definitely be able to say he's doing something his friends haven't. I'm not sure what he's looking for here, but I don't think sex is the end of it. Remembering back to high school, I equated the pain of a breakup and the energy of a new relationship with living. I was really dumb, but it took me a breakup or two to realize that. So I understand, but at 17 years old sleeping with another person wasn't going to help me out. It really wasn't him, it was really me.
That's all kind of rambly and I don't know how relevant it is, but one way or another, the mood he gets into about it is selfish, and it hurts your feelings. Have you sat him down and said "look, I understand that this is a big deal for you, but when you get like this it really hurts my feelings because [reason it hurts your feelings]"? Telling him that this behavior is really upsetting you and why may do more to curb the behavior than offers of free extra-relationship sex passes.
In terms of the lack of experience part, I'm sort of in your boyfriends situation in my current relationship and to hear things like "hey I'm down to try this, I'm down to try that", when what I really needed to hear was "it's ok if you don't want to do that at all right now", can actually be really scary. Especially being in a social group where being more adventurous is the norm, it takes a while to be able to assert preferences without sounding judgmental.
(Also because I feel really ignorant now, why would someone call a single bi girl a unicorn?)
That's one of those "we should talk about it and comfort each other" sort of situations not "delete the gym, go to the facebook, and hit the lawyer" sort of situations.
I'm 25. I never experimented with drugs, and when I was still pre/early college, I sometimes felt like I missed out on something, like I was supposed to have this experience that I refused because I just didn't want it. When I think back on that, I realize how dumb that idea was. Whether it makes you a better person or a worse person, as I am sure both drug experimentation and failed relationships/sleeping with many partners can do, the idea that a person has "missed out" on something is, in and of itself, absolutely ludicrous.
The grass is always greener on the other side, which is incredible, considering that in this case right now he's on the plushest lawn most people could ask for, and didn't have to mow the crabgrass across the street to get there. But he needs to realize that life only goes one way- forward, and no matter how much you give up to go back, you're just going to end up moving forward with less than what you had before.
So uh, don't talk about sex around the dude, seems like a no brainer. I wasn't comfortable around people like that either when they start talking about drugs, or other things I don't give a rats ass about or lacked experience in. So, I usually leave, though if you (his girlfriend) are engaging in the discussion it makes it harder for him to leave or really contribute and thus he probably feels inadequate around you.
So my advice, first and foremost, probably have a discussion with the friends (without him) about no longer discussing sexual past or conquests flat out. And if it's brought up, leave and do something else. Or something. I don't know what will happen to your circle of friends.
But if I was hanging out with my girlfriend and her friends and they started talking about riding the stiff mastiff, I'd feel uncomfortable as it is, let alone having a string of conquests myself to bring into the mix.
Adding in to the fact that the girlfriend (you) is freely admitting sexual pasts and he has nothing to contribute makes him seem insignificant as a whole in comparison to you. It can probably be demoralizing if one cares about their image among friends.
Maybe you should try not playing games like this or find friends that have more diverse interests.
If it would help you to understand, in your original post instead of using sex let's use the word "money". So, you've had lots of money, all of your friends have had lots of money, you guys all talk about having lots and lots of money, and going on expensive vacations, and buying expensive things, and funny stories about spending all of this money and he's making minimum wage. Think he might be uncomfortable with that? It's easy to see how he might feel like he's missing out on something, and wishing he had the same thing you and all of the friends have had.
if it's crazysauce wild sexual experiences he's missing, why not both of you make a list of things you'd like to try in the next year or so? an ex and I used to do this on cue cards, and every few weekends we'd grab one of the cards to try out (or more, depending...). I really like Ceres' comment on poly being a potential way to address it, but you both need to be comfortable with the idea of not-monogamy for it to work. And lots and lots and lots and lots of talking along the way
secondly: my mothers boyfriend had never dated anyone before my mom. They met in their 40's. not when he was 21 like your bf, but in his 40's. And yet, he's really happy with her, they happen to be this amazingly good fit (not without their bumps of course, they wouldn't be human without a few bumps). so he's not alone at least in that setup.
Preeeeetty much this. And there are definitely those that are just sexually open, people who have multiple committed partners and are STILL sexually open, then you have your swingers, etc... but they don't usually do it to work out the kinks (as it were) and then settle down forever with one person in the end. I kind of went on a bit about it without knowing what both of you are looking for, Totes, but if this is really a case of him saying "I just want you but I'm bitter" then that's its own thing you need to work out. Communication is the only way to do that; you need to be able to vocalize to him what you need from him, which sounds like it's for him to stop saying things that hurt you.
And for your part, I think you should recognize your own insecurity: you don't want him to leave you, and you feel like if he feels this way now it will end up with him either cheating or leaving, so you're offering him this "do whatever you want, just tell me about it and don't leave me" kind of deal. He may well feel in part like he isn't enough for you OR his friends, that he's boring by comparison and that everyone has moved on and had all this experience and he never did, but it sounds like you also worry that you may not be enough experience for him, and that he may at some point need to sow wild oats in a way that involves dishonesty or breaking up. These are both feelings of inadequacy, and it IS taking two: he feels it and voices it, and then you feel it in response. You really need to talk to each other about all of these things.
Because they're bloody impossible to find.
This is specifically refers to single bi girls who want to have three-ways with a previously existing couple.
The fact that he's looking to bring another girl into the mix indicates that he's interested in having sex with another woman but isn't willing to break up with you in order to do it. That tells me that in general he likes the relationship and wants to be with you, but it may also mean that he's afraid of being single again in case he goes from a good, happy relationship to no sex at all and no girlfriend for a long time. People who are insecure about their sexual experiences generally do not have a lot of sex once they're fully single again.
Maybe instead of trying to fix his insecurity by bringing other people into the bedroom, perhaps you should look into changing some element of your current sexlife. Ask what he wants to do with this supposed other woman, and maybe ask him to make a list that you can both go over. Perhaps it'll involve some dressup, or other positions, or only oral sex for a week/month, or otherwise changing things so that he gets what seems like more experience but with the same person.
I think you can also use your experience to tell him that, for the most part, sex is sex. It isn't really different with different people, and it's best when you're comfortable and with someone you love.
Your physical age difference is only three years but your mental ages, based on the personal experiences you've had, is vastly different.
I think you've been very considerate and are trying very hard to accomodate him, but if his immaturity keeps him from appreciating what he has there isn't much you can do to help him other than wait for him to grow up. Whether you're willing to do that or not is up to you.
This. 100x this. The two examples you use are from situations that he experienced, not conversations that he initiated. I also think the wealth analogy is very appropriate. Obviously, a big part of a relationship is understanding your partner's insecurities, anticipating them, and reacting appropriately. This is a major issue for him and my advice would be for you to adapt the relationship around it. The fact that you are trying to solve this problem and are considering his outlook is a really healthy place to be, but I don't think trying to push him into sexual situations with a third person is the way to go. Nor are playing games like "I Never" and hanging out with friends that revel in this kind of discussion. My current GF does not appreciate gaming the way some of my previous partners have. It doesn't mean I'm actively trying to entice her, to change her, to "catch her up" in the gaming world. We share a TON of other interests so ignoring one of mine is not a big deal at all. Would it be great if she could sit down and play some Xcom with me? Hell yeah it would, but I'm not going to sacrifice her and the relationship with all of its other amazing things because we don't. Hope that makes sense.
My honest advice is try to find things he wants to do and do them. Or come up with something you've never done before and do it with him. And make sure he knows it.
The problem is that he feels like an outsider. And he lacks the skills to cope with that. Plus there could be a lot of unchecked condescending attitudes towards him, possibly even coming from you yourself, that you aren't picking up on.
A big part of it was actually having some of the experiences I craved, and having partners who were cool with open relationships (I also identify as poly, BTW) was a huge help. Sometimes you just have to go out and do the things you want to do.
But a lot of it required internal work on my self-image, too. A certain amount of this involves learning how to go easy with comparing yourself to other people. (I'm not gonna lie; it was easier for me to do that introspective work once I'd gotten a few tastes of what I craved.)
Let's say you guys actually did find a unicorn and had a hot threesome with another girl. Somebody who is prone to self-criticism will still find reasons why that wasn't good enough. The specific content of those self-deprecating thoughts might be anything: "I still haven't had as many partners as my girlfriend" or "I wasn't man enough to find another partner on my own, I had to get my girlfriend to help me" or "Oh man, is my girlfriend unsatisfied with just me now?" Sometimes the self-critical brain starts with an emotion ("I don't like myself") and just fills in whatever crappy reasons it can find.
You mentioned opening your relationship or being poly; but the thing about being poly is that you meet people with a wide spectrum of sexual experiences. There are the poly people who are in the 40s and opening up a marriage for the first time; there are people who started having sex in their early teens and have had sexual partners in the double or even triple digits. If he focuses on comparing himself to the latter, he's going to feel even more inadequate.
He has to choose to change his attitude - he has to consciously remind himself that scorecards are bullshit, the number of sexual experiences a person has does not make them a better or worse person. What makes one a better person is being able to treat people with compassion and respect - and that includes treating oneself that way.
Unfortunately, you can't really force him to see himself in a more positive light. You can (and should!) tell him the reasons you care for him and admire him and hope that he accepts those reasons. I think it's a good call to avoid games like Pervert in the future, but there will be other times this insecurity will bubble up unless he deals with it internally.
the "no true scotch man" fallacy.
This created 2 problems in my mind. If I got married to this person would I ever know if this was a great relationship or merely a decent one? Obviously I know it's not bad, because I am happy, but how will I know if it's totes awesome or just meh, without having some previous examples to compare to?
The other problem was that in a very abstract sense, dating seems like a lot of fun, and I would never get to experience it. This is why I would feel uncomfortable when people would share there awesome dating stories; because it was another reminder that I would never have similar experiences. It's easy for anybody who's actually been in several relationships to say it's not that big of a deal, and that they would prefer to find one person to be with. I'll never know for sure if that's true for me too, because I'll never be in another relationship.
That's my story, and the best advice I can give is this. Regardless of what the two of you would like to try sexually, the boyfriend has to make a decision. It will always suck to never have gotten the chance to date multiple people, and grow as a person through those experiences. Either the relationship you're in now is worth giving that up for, or it isn't. I would have an honest conversation with him and try and convey that message to him. For me, I don't think it would be possible to have those experiences and still be in a relationship. You can do some things, and maybe those things would be helpful, but in the end the decision will still be there.
Edit - I just wanted to try and clarify problem 2 a little bit more, because a lot of people are assuming the OP's boyfriend feels inadequate because of his lack of sexual experience. From the OP's description, I felt much the same way, and I could give two shits about whether or not I had slept with as many girls as most people. Or had as many crazy experiences. For me, it was all about settling down before I had explored.
It's hard to explain but in the end it doesn't matter to me what anyone else thinks about how many people you should date before settling down, or how many people my friends have dated, I just wish I could have dated because it sounds fun. And when people mention their awesome stories, it reminds me that I still wish I could have dated. In the end, getting to be with my awesome wife was more important to me than getting the chance to date.
** I also want to clarify that I use date, instead of sleep around, because I think there is more involved in dating, that I would have liked to experience, than just having sex with different people.
Okay. This I follow.
How do you know? Has he communicated that this bothers him?
Are you not presuming a bit too much at this point already? Again, have you actually communicated about this?
Hold the horses. So YOU want to add another woman, not him? This is where I'm getting lost.
Again, are you forcing him to do something he does not want to, or has never thought of?
So it's not you. It's your friends he has issues with?
But... how do you know what he feels? Have you communicated about this issue specifically?
I don't quite follow whether your conversation about what's bothering him ever took place.
Again, it's probably all the wine I had, but there are so many issues and assumptions going on here that I can't quite follow who wants what, who's doing what, etc...
Next you need to be honest with yourself. Do you wish that your sex life with him was more adventurous? I'm getting the feeling that you do and your using the idea of helping him get experience as cover for your own desire. If you want more then tell him. Keep it simple "I would like to do this with you what to you think?"
Be honest with yourself and figure out what you want and then sit down and talk with him.
So I haven't always communicated totally clearly in this thread. There are a few comments I would like to address in no particular order, and thank you so much everyone for your advice.
1. It's not that he was against non-relationship sex before hand, more that he was all shy and unworthy feeling. That has improved a lot and although I was the first to bring it up a few months in, he was enthusiastically interested and still is. It has been a no pressure thing, I was approaching it more as "if it happens awesome, if not I can survive" but he's been more interested in trying to make this a reality lately, though placing it mostly on my shoulders because he's a lot shyer than I am and he feels like I'm more suited to the task. I was trying to get across in my original post that this isn't something I'm having pushed on me, but it's certainly an interest of his as well as mine.
2. @ceres I had been hoping that you would respond to this and if you're interested would love to continue a conversation about poly-related topics either in thread or PM's because that is a question I've been asking myself for years, where exactly I fit on the scale in regards to how my ideal relationship would work between totally monogamous and totally open, and I really like talking to people who have been there. One thing that I do know is that I was never proposing a "don't ask, don't tell" scenario. I want to know and I have been in scenarios in my past where such things were handled honestly and it was more than okay, kind of awesome actually. I'm not a jealous person in the least, I just hate being lied to. And you're right, there in insecurity on my part. This is the best relationship I've ever been in and I don't want to lose it over something like this. Sex with him is better than good - there are advantages to his inexperience in that he's excited to learn and try new things. He doesn't have any built up "repertoire" of things that worked with other girls but won't on me, instead he likes to hear from me what I like and is open to trying just about anything. He's wonderful with that though a little unsure of anything he'd like to try because he's never had anyone to try with before.
3. About the friend group, that's a tricky thing because he hasn't exactly told a lot of them about his lack of experience, so to ask them to shut up about theirs would raise obvious questions as to why. The Pervert game was started at a party before I showed up, they just placed a piece for me around the average position for everyone when I showed up. It may not have been the best judgement, but he was already playing when I got there so I figured why not. The game gets old fast though, I doubt it'll be played again for a while and if it is I think I'll opt out. I'm not the type to start the sexual history discussions, but I will admit I can get swept into them sometimes because I find the whole subject of sexuality very interesting beyond just the titillating aspects. Sex is neat! We do have other common interests though, it's not like this comes up every time we get together.
4. @esh with all respect, I'm going to have to disagree with you. I see this as something worth working through because of the myriad of extremely wonderful aspects of my relationship I haven't written about. This is 2 years of more happiness than I ever expected and I'm not interested in calling it quits.
5. The gist of what I've been getting here, and correct me if I'm wrong, is that my initial thought was right and that this is above all something we'll just have to communicate about. I've been holding back on talking about being hurt by his comments because I don't want to seem like I'm dismissing them. I remember being 18 and utterly inexperienced while all my friends had these scandalous things to talk about and feeling left out and somewhat mystified. It's the closest I have to similar experience and I'll try to be more sensitive about it in the future.
Thanks again so much everyone. I may have more to respond to tomorrow but I think I touched on all the major points I wanted to make.
A couple years later I realized I'm just not the type of person that enjoys a lot of sexual partners in a short amount of time. Even if given the opportunity to have random hook-ups all the time, I wouldn't take them. Once I realized what kind of person I am the rest kind of fell into place.
So, I think this guy will either grow out of it if given time, or will end up sabotaging the relationship and figure it out afterwards. The best thing for you to do is just keep reminding him that you like him for who he is, and that includes his lack of sexual experience. Reinforce to him that the sex is good... I would probably give it a little time before exploring a more open situation, but I'm pretty conservative about those things. Maybe mention every once and a while how much happier you are with him than you've been with other relationships.
You are welcome to PM me any time! I can't claim to be an expert and I'm only just starting to do my own research (finally, like a year and a half into seriously exploring things) as more than "it's a thing I've heard people do" and looking into terms and whatnot, but I can tell you what I have in my relationship(s) at the moment, and what's worked for me and for us.
I'm glad you don't want to give up on the whole relationship. It may or may not work out in the end, but that's every relationship, and it's just as good to be able to pick out a problem and say "this is something we can work around or through" as it is to be able to pick out those dealbreakers, and so, so important to know the difference. This one sounds entirely like a matter of communication and security with each other, which WILL involve you being able to talk about what this all means to you in terms of how things he says make you feel. Why would that be any less important than knowing that rubbing your experience in his face would make him feel terrible? Hint: it's not. If you are feeling something bad related to his words and actions, it's important to be able to vocalize that. It's not the same as whining or dismissing his problem, I promise you.
Of course, it's harder to realize that when you've never had sex with anyone but 1 person.
When you do things in the bedroom, are you generally the person who decides how things take place? Maybe you're unconsciously driving the action; things like not proposing a position or a toy or something because you've already been there, done that for example. Maybe doggy style doesn't do anything for you, for example, so you've never even brought it up (or when it did come up, you maybe said "oh that doesn't do anything for me"). So, maybe try doing things you've never done with him but that you've done before. I'd also tell him not in a sense of "I did these things before, but not with you," but rather in a "you know, I don't think we've ever done [thing], let's try that out." It will give him the sense that you're exploring too, which will make him feel less of an outsider.
If he's intimidated by your previous sexual prowess (or perhaps your openness to non-monogamous relations) there may be a deeper issue at hand. Either way, talking is the best way to work out issues, I feel.
Insecurity is clearly an issue. Insecurity is also something I'm intimately familiar with, as it nearly lost me my current relationship a few months ago. I ended up in therapy and it's worked WONDERS.
Anyway, I can actually kind of relate to your boyfriend - not so much on a sexual level, but on a 'lack of a certain kind of experience' level. My current girlfriend is really well-traveled, and has done a lot of really interesting things, as are a number of my friends. Me? I spend most of my time in front of a computer or television screen, and the last adventure I had was when I was maybe 13, climbing a dead tree to try and get to a jury-rigged zipline that a friend had put up (and ended up falling from that tree). So, anytime people end up discussing things like that, I usually only have the same one or two stories, all of them either really old, or not really related (I try to work in my medical history, to mixed results). For a long time, this bothered the fuck out of me. I had wasted my life on fictional adventures while all of the people around me were out having real ones. I wanted to think of myself as the "hero", but I had turned out not even as the "sidekick". I was just the "citizen". When these things came up, I felt really, really worthless.
After a month or so of weekly therapy, it came down to a number of personal insecurity issues that I've started to work through. I still have time to forge new adventures, and that's great. This, however, is where the two stories digress.
I don't think the solution lies in bringing in another woman to sex your boyfriend. It's treating a symptom, rather than a cause. It might work for a little while, like aspirin for a broken leg, but eventually that leg is gonna get worse and worse until it completely breaks down on you. He needs to focus on what he's got, not what he could have had, or what he might have one day if things would only work out the way I want them to. My therapist would probably tell him to avoid the word "should", as in "I should have had sex with more people" and "I should have more to contribute during sexy story time", and the phrase "what if", as in "What if we can't find another girl within x amount of time?" and "what if my lack of experience actually bothers her more than she says?" I'm not a liscensed therapist, but I would bet every dollar I have that those things are going through his mind.
Insecurity is a parasite. It will turn even the most reasonable person into a shivering ball of doubt. I HAVE sexual experience, and for a long time I doubted my performance, my size, everything about my sex life, no matter how much my girlfriend told me different. I couldn't trust anyone, because I didn't believe in myself at all.
I say this a lot, but therapy really might be a good decision in this case. It's not magic - psychologists aren't wizards - but if he's open to the idea, or hell, you could both go in for sessions together to aid your communication, then it really might start to heal the real issue. Might be that he's like me - I need fairly constant therapy (at least right now), or I start to go a little nutty again - or it might be that he has some kind of breakthrough and the world's his damn oyster. Either way, best to get at the root of this weed before it wrecks the whole garden.