Topping my boyfriend... who's a top

[CapeAndCowl]

Hey fellers, I'm finding myself in a bit of a conundrum. I've been seeing this guy for a few months now and our relationship has been steadily becoming more and more significant.

Just recently have we had sex for the first time. He's the first guy I've let penetrate me. I've always known I'd be a versatile kinda guy- the constant role reversal is a huge turn on. Suffice to say: I wanna top him. Really bad.

Here's the issue: he's an time-tested top. He's bottomed very few times in previous relationships, described it as uncomfortable, except for one time when he said it was 'okay'. He's willing to bottom for me, but he doesn't seem enthusiastic. Suck it up and take advantage of the offer right!? well...

I'm pretty much a pleasing fiend. Part of what gets me off is getting him off. So, there's a layer of complexity to the mix-- I want this to be great for him. I want him to get his kicks from bottoming and I wanna do it right.

So guys, lay it on me: what's your best topping tips?
Tops: what could get you going to let your guy slide it in?

 

[Rolyo85]

As a versatile top in a relationship with another versatile top, all I can say is he has to want it and be excited about it. For me, a lot of foreplay and lube do the trick, usually followed by sitting on it, because then I get to control the speed, depth, everything. If you're a please fiend (so am I), you have to let it all be about him. You shouldn't even expect to get off, at least the first time. Let him go as far as he wants for as long as he likes. If you guys are serious it won't be a one time thing.

 

[CapeAndCowl]

Thank you Rolyo85. I'll definitely keep that in mind. Your description sounds like my first time... I definitely had to take it slow and deliberate. I guess that's part of both mine and his reticence to bottom... it takes so much time to get prepped.

From his recollections, he doesn't really get a lot of pleasure from his ass being played with... but I can't help to feel like his previous sexual partners, well, sucked at it.

I know this is rather personal, but is there anything in particular that is especially (perhaps, surprisingly) pleasing about anal stimulation you discovered through your own exploration?

EDIT: I might also add that, he's been very responsive to my sexual needs. I'm very aggressive, as is he. I realize that he's not necessarily turned on being submissive. Any suggestions to make him feel, for lack of better term, powerful while getting fucked?

 

[bankside]

I completely understand your interest in switching. I'm the same. I don't know if I could be with someone who only wanted it one way all the time. Actually I know I couldn't.

There is something the same about topping and bottoming. I see them as interchangeable. And there is something different about topping and bottoming. I want to share the variety of this experience with the one guy I care about. I want to experience what he does and I want him to know how he makes me feel. That idea is strongly arousing.

I also would have a hard time if I thought the guy was only tolerating it to please me. If my guy didn't get the dynamic that I find so compelling, I would find that to be disappointing and kind of a turn off. If it's a chore for him, I'd say don't bother. And then I'd probably my own desire for him would fall into chaos.

I don't understand why people don't care about one half of sex. I accept they seem happy that way, the world takes all kinds. But I can't say I get it. And especially because for so many people, it isn't just about enjoying one kind of physical act more than the other. There is a whole psychological package about "what it means to be a bottom" or "what it means to be a top" that I don't get. Or there is a whole "masculine cliché plus whoever has the biggest penis = top" and "feminine cliché plus whoever has the smallest penis = bottom." I don't get that either. It never occurred to me that anyone would think about sex that way.

In my own relationship I think I could handle it only if one of us had to give up part of sex because of a medical issue. Otherwise it would just be too weird.

My question would be, isn't he at all curious to know how you can do it? Isn't he at all curious to find the same joy in it that you do? Isn't he bored with himself for only topping while you can do both? Again, I just don't get it.

 

[Rolyo85]

Trust me, if he's on top of you and riding you, you'll feel quite powerless As for particular advices, I don't think I got any. It just becomes nice at some point, you increase the speed of friction and then stuff squirts...

 

[CapeAndCowl]

haha, thanks Rolyo85. Increasing speed. Friction. Stuff squirts. That's a hefty set of notes, but I'll do my best

Bankside, it's funny you mention the whole cliché aspect. He and I are physically fit, our dicks are identical, and our social presentations are that of your average joe. I make those points to say that, when comes to those stereotypes, they don't really apply to our relationship. However, I can definitely see the fear that such stereotypes might become relevant, especially with him. I just don't feel submissive when I'm bottoming. I'm a man, dammit, and I'll take a dick like one!

But I don't think he necessarily has the same level of self-assuredness. Which is normal, especially for guys whose 'masculine' identity is important. I understand this feeling, I had hesitation about bottoming, which is probably why I waited so long to do it. I didn't want to be anyone's bitch. But then I realized- that's not what bottoming is about (unless you want it to be). I like the feeling of my prostate getting stimulated and I enjoy the fact he is getting pleasure from fucking me. I hope to give him reason to feel the same way.

 

[Seasoned]

Welcome to JUB.

Keep in mind that sex, no matter how intense and physically pleasurable, is primarily mental. My husband and I will have our 29th anniversary in July and it took us quite some time to become versatile. Even now we have our primary likes, but we mix it up for fun. Some people develop blocks to either topping or bottoming and some even think it's "more gay" to bottom, so if there's even a hint of internalized homophobia bottoming takes on a negative connotation. I think there's less of that kind of thinking today but it was common in the back pocket, colored hanky era when I was coming out. I look at it this way. If something works well for guys' bodies it ought to work well on mine, if I want it to. And that's where the mental part plays it's role.

Now, as far as getting him ready, realize it could take a long, long time. He needs to be physically and mentally ready. So... Be extremely playful for short, teasing bursts. Get his body in various bottom position for just seconds, even with clothes on. Give him a kiss on the ear and whisper someone sexy and provocative. In the shower tell him, as he goes to wash his butt, "let me get that for you." Compliment his ass, both in private and, discreetly, in public. Go shopping with him and tell him which jeans or pants flatter his ass. Do all of this from time to time with being obnoxious. When you stand and kiss grab his cheeks. Since your dicks match up let him know if you can take it so can he.

His hole is sensitive. Why wouldn't it be? He has to learn to accept pleasure there. Did you ever clench up not knowing how fresh you were? Well, I think there can be a mental clenching even if we don't want to admit it. What I'm saying here is that patience is the key, but it's playful patience and it shouldn't be gamey. You can tell him exactly what you're up to. "I'm going to make this pretty tight hole as hungry for my dick as mine is for yours," or anything else that's more natural sounding for the two of you.

Whatever you try don't expect it to work over a weekend. It's going to take time unless he changes his thinking and then all it takes is a slippery minute! Good luck.

 

[CapeAndCowl]

Seasoned, thank you for the sound advice. The dirty talk is a good idea. I especially like the "I'm going to make this pretty tight hole as hungry for my dick as mine is for yours" line. I'm totally using that.

I do butter him up verbally and physically all the time. I tell him he has a cute butt, that it looks great in the underwear he's in. I grab his ass, grind and dry-hump it. He goes with it and enjoys the attention. This goes back and forth, as he will do the same to me.

Sometimes I feel like this is a power struggle to secure supremacy. Since he's aware that I enjoy anal stimulation, it seems acceptable for him to allude to fucking/fingering/playing with my ass. But when I allude to doing the same to him, he acknowledges me with a positive, but reticent air. I feel like I'm nagging or being pushy.

He and I are going camping this weekend, I'll be sure to post back with any results of my further explorations.

 

[Charmander]

Have you tried rimming, tongue fucking?

 

[CapeAndCowl]

I've brought it up and willing. He hasn't had his hep A & B boosters, so he was concerned about it. If we're in the shower after suddzing up, I might try to talk him into it.

 

[Darted]

In my relationship, there's no top or bottom. If one of us wants to get fucked it happens, if not it's no big deal.

 

[TX-Beau]

Alright. I don't like to bottom. I don't have any hangups about bottoming, I'm quite happy to do it if that what my guy wants, but I don't get any pleasure from it beyond pleasing him.

It's uncomfortable, and awkward and no matter who promised what miracles or what preparation they did - with my enthusiastic participation, I've never gotten off on it, ever. Period. It's not something he has to "get over."

So yeah, some of the guys I've dated had huge issues about this, because if I wasn't getting anything out of it, they felt diffident about asking for it.

I suppose what I'm saying here is, just because it's not doing a hell of a lot for me, I WANT to make sure the guy I'm with gets what he needs, I'm not going to say no - and it's OK for him to take his pleasure which I will enthusiastically provide, even though it's not doing anything for me but making him happy.

If your guy is like me, and willing to do that for you - don't over-think it, if he's willing to do it for you, he's trying to make you happy, and take him at his word about that, you need what you need, there's nothing wrong with that. You can always roll him over after and swallow his cock.

You are pleasing him, by letting him please you.

 

[TX-Beau]

You're not nagging or being pushy by discussing your sexual needs with the guy you're fucking. i'd say that's a requirement for a decent relationship.

 

[CapeAndCowl]

TX-Beau, thanks for your input. I think I'm finding myself a situation similar to what you describe. I am diffident about actually topping him because I do know that he hasn't enjoyed it in the past. The main difference here is that, from what he describes, he does get off every time. In fact, he made that an explicit point- "If you're getting fucked, you should be getting off" (I'm paraphrasing). I think that's an absolutely fair trade. It makes me think he might actually enjoy himself, albeit in the right circumstances.

Do you have any insight on what makes the experience easier overall? Or is just a 'suck it up and wait it out' kind of approach?

 

[Rolyo85]

It definitely isn't. Just try out different positions until one fits. For example, regular boring missionary with my legs around his waist is literally my favorite position while bottoming, yet if he lifts my legs over his shoulders it becomes almost painful. A small change and a world of difference.

 

[AlmondMilk]

Making out, licking all over may help I know that gets me horny and ready. Does he need help loosening up? Perhaps if he takes a warm/hot bath/shower he can loosen up some. And what about massages during foreplay?

 

[csm123]

Just wondered if you ever thought about introducing a few toys into the bedroom.A set of buttplugs that start small and work upwards in size could help him/both of you get used to having something up there without feeling pain or having the feeling you need to take a dump.

If you could get him interested in toys,after a while you could get him to top you while wearing a buttplug and this could soon change his mindset about bottoming!

 

[Lube]

A lot of good advice here.

Some guys are natural bottoms and others really have to work at it to open up their holes. With the latter, you have to work slowly and methodically. Get them to relax and enjoy stimulation without penetration. Then slowly work toward penetration.

By slowly I mean both over time (working for weeks or months over many different sex sessions) and also long times for each sex session. Dan Savage had a column last month talking about fucking a guy for the first time, and talks about taking at least half an hour warming the guy up, playing with his ass with toys and/or tongue and/or fingers and lube.

Guys who aren't natural bottoms need this long workup.

 

[Lube]

Here's the article I was talking about: Savage Love by Dan Savage - Seattle Columns - Savage Love - Dan Savage - The Stranger, Seattle's Only Newspaper

 

[fluxflux]

I'm a top. I've been fucked more than enough times to know i don't like it. The idea of getting fucked does turn me on though and I must say I am jealous of guys who love a cock up the ass. I dated a guy who used to cum just from being fucked, he didn't have to touch his cock at all. That was hot.