I'm a strap-on "virgin" (m) with some questions...help?

[Skoti]

It strikes me as funny, but maybe it's inexperience...I read several (though admittedly not all) of the posts on this site, and I noticed that none of the men really talked about what a heavy gift it is to give themselves to a woman in this manner. I've never done it, but my future wife is moving here from Australia before too much longer, and that's something we both are keen on.
I most look forward to having this woman have me the way I would never let anyone else have me, to giving myself in such a way that makes me, as a man, vulnerable in every way imaginable. She could hurt me physically. She could denounce me as a man. She could attack my heterosexuality. She holds something in her hands that I didn't even know was so fragile...my masculinity, my comfort, my sexuality, my trust, my confidence. Maybe this sounds weak, I don't know. I was looking and I saw a few pictures of some of these women that enjoy pegging, and I was physically appreciative, for sure, but not knowing them, and not TRUSTING them, and not being compelled to give such a huge part of myself to them...am I just a naive "virgin", or is this, ideally, really an incredible gift to give to a woman (and yourself), or is it just something to give to the first hot chick with a strap on?

To me, it's frightening in its implications. I love her so much, and look forward to it to the point that I've dreamed about it. I'm frightened of it to an amazing degree. I'm not trying to talk myself up or anything, or redeem my masculinity (fact is, I want her to fuck my ass with a strap-on), but I'm the guy that has scars on his hands, is a man's man, went to prison and fought GUARDS and won, and slept with an unsafe number of women at a younger age. I'm the guy that fears nothing (except sharks, for some reason ), and I WANT to give her that strength and have her be the other half of an act that rips walls and defenses and toughness APART in a dizzying give-and-take scenario.

I have some questions about cleanliness, especially.

Also what should we get? It's very important to me that the very act be sexually stimulating for her...

Sorry if this post is sort of jumbled. It's still sorta confusing in my head, in a lot of ways. Any comments, advice, and questions would be greatly appreciated.

Any comments are most welcome.

 

[Vixandra]

I cannot speak to the strap on part but I can add insight in the anal side. The top two things needed for anal sex (beside the penetrating object) are
1. Communication
2. Lube

I cannot stress the importance of either of those. When in doubt, add more lube. Anal sex is, at least for me, a huge trust issue because it can go so painfully wrong. If you cannot communicate what is going on and have that heeded by your partner, it becomes a breeding ground for disappointment, the bad kind of pain and resentment. But if done with a partner that listens and wants the experience to be amazing, than its good for everyone.

You might consider cross posting this on the How To board or the BDSM board asking for strap on recommendations for her. Best of good luck to you both.

 

[LindsayRae]

Hi. Welcome to Lit. You may want to try the How To board for some Q & A. Good luck in your search.

 

[greenjacobin]

Please feel free to PM me or contact me by email (my preference). I can answer many of your questions and prepare you for some things you have probably not considered.

If you would prefer to discuss it "out here," that is fine by me, but most men prefer private discussion of topics that might be considered "unmanly."

 

[Bbb13]

I am interested also, have u tried yet? Only have used small vib in past, will need to talk wife into more however. Lol

 

[Nasty_Deeds]

It strikes me as funny, but maybe it's inexperience...I read several (though admittedly not all) of the posts on this site, and I noticed that none of the men really talked about what a heavy gift it is to give themselves to a woman in this manner. I've never done it, but my future wife is moving here from Australia before too much longer, and that's something we both are keen on.
I most look forward to having this woman have me the way I would never let anyone else have me, to giving myself in such a way that makes me, as a man, vulnerable in every way imaginable. She could hurt me physically. She could denounce me as a man. She could attack my heterosexuality. She holds something in her hands that I didn't even know was so fragile...my masculinity, my comfort, my sexuality, my trust, my confidence. Maybe this sounds weak, I don't know. I was looking and I saw a few pictures of some of these women that enjoy pegging, and I was physically appreciative, for sure, but not knowing them, and not TRUSTING them, and not being compelled to give such a huge part of myself to them...am I just a naive "virgin", or is this, ideally, really an incredible gift to give to a woman (and yourself), or is it just something to give to the first hot chick with a strap on?

To me, it's frightening in its implications. I love her so much, and look forward to it to the point that I've dreamed about it. I'm frightened of it to an amazing degree. I'm not trying to talk myself up or anything, or redeem my masculinity (fact is, I want her to fuck my ass with a strap-on), but I'm the guy that has scars on his hands, is a man's man, went to prison and fought GUARDS and won, and slept with an unsafe number of women at a younger age. I'm the guy that fears nothing (except sharks, for some reason ), and I WANT to give her that strength and have her be the other half of an act that rips walls and defenses and toughness APART in a dizzying give-and-take scenario.

I have some questions about cleanliness, especially.

Also what should we get? It's very important to me that the very act be sexually stimulating for her...

Sorry if this post is sort of jumbled. It's still sorta confusing in my head, in a lot of ways. Any comments, advice, and questions would be greatly appreciated.

Any comments are most welcome.

I can just give my opinion, but you need to get past the feeling of this being a gift to her, or this somehow making you less of a man. If you are heterosexual, you will be heterosexual as long as you feel heterosexual. If you are a man’s man, you will always be a man’s man; no one else has a right to label you, me or anyone else. You are who you are and taking a strap-on from your wife or girlfriend isn’t going to change that. I think we put too much emphasis on labels. If you are really concerned about it, just keep it private between you and your lady. A lot of couples do. As far as it being a “gift” to her? Anal play for a man is about stimulating his prostate, and if your lady enjoys stimulating you, that’s even better.

As far as cleanliness, it is wise to be concerned. I am a stickler about cleanliness during anal play myself, (perhaps more than I should be), but I hate to come across shit during sex. Humans have bacteria in their intestines that can make you sick if you carelessly contaminate something you eat or drink during anal play session.

The best way to get yourself clean is with an enema; in fact, an enema can be pretty refreshing in its self when done right. If you do decide to take an enema first, DO NOT put a wine, beer, (or any kind of alcohol), herbs, coffee or drugs in the enema. Your colon will absorb these items more efficiently than your stomach and you can over dose real quick. Until you get experience with giving yourself an enema, follow the manufactures instructions that come with the enema bag. A person can actually die from alcohol poisoning or drug over dose this way

One suggestion I would recommend is to clean yourself, lube up your finger, and explore a little before your fiance arrives. Find your prostate and learn how to stimulate it. It’s within the reach of your finger, and about the size of a walnut. If it’s the size of a lemon, go see a doctor; however, at 27, I doubt you will have a problem. You can actually make yourself cum by massaging your prostate, and it feels quite good.

Avoiding pain. The first time may hurt a little; however, it doesn’t have to. It hurts because you tense up; the key is learning to relax when she enters you. I will give you an example: you can crap a turd the size of a cock, and it doesn’t hurt, but let someone shove a dildo up your ass, and it hurts. When you are taking a crap, you are relaxed, but when you are being fucked for the first time, you tense up. You can buy different sizes of butt-plugs to help you learn to relax and stretch you out a little so it won’t hurt, or you wait until she gets here and work it out together. When she gets here, start with a smaller dildo on the strap-on and use plenty of lube. Let her slide it in slow and easy, and focus on relaxing your anus as she enters you.

It is commendable that you want to please her by doing this; however, to please a woman in this way, you first have to understand how a woman receives pleasure. A woman receives pleasure by pleasing her man. When she is fucking you with a strap-on, she isn’t going to feel a thing from that plastic dildo, but when you start moaning from being pleasured, she is going to feel really good. If you want it to be good for her, make it good for you. Her pleasure will come from giving you pleasure.

 

[bad_dave]

This attitude makes me bang me head on the desk, being fucked in the ass by a WOMEN does not effect your sexuality if your heterosexual because its a WOMEN.

 

[Skoti]

I am interested also, have u tried yet? Only have used small vib in past, will need to talk wife into more however. Lol

No, she doesn't come back to the States until September. I'm excited, and not just cuz of this.

 

[Skoti]

I can just give my opinion, but you need to get past the feeling of this being a gift to her, or this somehow making you less of a man. If you are heterosexual, you will be heterosexual as long as you feel heterosexual. If you are a man’s man, you will always be a man’s man; no one else has a right to label you, me or anyone else. You are who you are and taking a strap-on from your wife or girlfriend isn’t going to change that. I think we put too much emphasis on labels. If you are really concerned about it, just keep it private between you and your lady. A lot of couples do. As far as it being a “gift” to her? Anal play for a man is about stimulating his prostate, and if your lady enjoys stimulating you, that’s even better.

Heterosexuality: I guess that's something that's still a little confused in my mind. Still some things to get over, I suppose, but I will.

Gift: It's a physical gift to me, obviously, but for me to open up to her and trust her like this, well, to me it DOES feel like a gift because it's not something that I'd probably open up to anyone else about, at least not anyone in my past. Make sense that way?

Your information on the cleanliness thing is much appreciated...there is definitely nothing sexy (to me or her) about shit. I actually appreciate all the information you gave...it's pretty much exactly what I was looking for and wasn't getting.

Thanks!

 

[Skoti]

This attitude makes me bang me head on the desk, being fucked in the ass by a WOMEN does not effect your sexuality if your heterosexual because its a WOMEN.

Well, it's easy to be confused about it, at least initially. The fact that men don't turn me on in any way conflicts with the fact that it'll be a COCK (or reasonable substitute). It's just hard to get used to, I guess, in my mind. Although the mental image of that petite, sexy little body with a strap-on jutting out is crazy hot. I think part of it is the fact that it IS a woman, THIS woman in particular. It's still hard to adjust to. I mean, would a chick with a real dick turn me on? It just takes some acclimating, I guess. I'm not trying to label anyone, really. Just trying to make my peace with it, if that makes any sense.