Sex with my best buddy.

Bluespeedoz · Nov 21, 2004

Hi,I've had very regular sex with chicks since I was 13 and until I was 22 I thought I was straight. My best buddy and I have known each other since kindergarten and have that sort of man / man relationship only guys who trust, love and respect each other can have and understand. Three years ago he told me that he is bisexual and asked me if I would consider having sex occasionally with him. I guess most guys however strong their friendship was would have responded by putting a fist in his face. After careful thought I decided I wanted to explore the "gay" side of my sexuality personality with him and so we went ahead and had protected sex together. I discovered that I enjoyed "top" sex with him while he likes to be bottom and we are both very happy with our relationship. He has now told me that he would like as part of our love making to fuck me in the ass although he is not insisting I must let him. I'm not sure I'm keen on the idea because im my mind it diminishes my masculinity and because I hope to marry one day (I'm presently enjoying very regular protected loving sex with a chick my age (25). However there is a part of me that wants to say yes to my buddy, because I'd like to know what getting fucked in the ass feels like. Has any guy been in a similar situation or able to offer me some advice please about whether I should let my best buddy fuck me?

-_-

If you would be more comfortable respnding by email my address is bluespeedoz@mac.com

woskxn · Nov 21, 2004

Well, you dont want to do anything you feel too uncomfortable with.

HOWEVER, I would not look at it as an experience where you are losing your masculinity. If you are the best of buddies, and it sounds like that, you should not look at it that way at all. Just look at it as both of you feeling so close that you can experiment that way as well.

At first, it may hurt abit, or a lot...so use lot of lube and you should be ok (if u decide to go through with it) The more you get comfortable with it though, the more it will be better and feel more more satisfying.

B_RoysToy · Nov 21, 2004

Bluespeedoz:

Congratulations for 1) being str8 and yet mature and open-minded enough to be able to recognize your curiosity and 2) having a friend with whom you are close enough to explore sexual activities. Your situation proves we are social individuals who have the capacity to have strong emotions for either sex.

Since you and your buddy have had anal sex, always with you as top and him as bottom, I can't see that changing positions would alter any classification making you less masculine. This idea totally depends on your concept and I encourage you to give it thought. The only way to learn what it would be like for him to fuck you in the ass would be for you to come to terms with your concept and have the experience. Although I'm not one of them, I know guys who have long-lasting successful marriages, love their wives and have sex with them several times a week, and permit close friends to have anal sex with them when conditions and situations present themselves.

I hope you choose what is best for you, Bluespeedoz, and you'll always feel you've made the 'right' choice.

madame_zora · Nov 21, 2004

Roystoy, that was beautiful! Ditto that.

Bluespeedoz · Nov 21, 2004

Originally posted by RoysToy@Nov 21 2004, 05:13 PM
Bluespeedoz:

Congratulations for 1) being str8 and yet mature and open-minded enough to be able to recognize your curiosity and 2) having a friend with whom you are close enough to explore sexual activities. Your situation proves we are social individuals who have the capacity to have strong emotions for either sex.

Since you and your buddy have had anal sex, always with you as top and him as bottom, I can't see that changing positions would alter any classification making you less masculine. This idea totally depends on your concept and I encourage you to give it thought. The only way to learn what it would be like for him to fuck you in the ass would be for you to come to terms with your concept and have the experience. Although I'm not one of them, I know guys who have long-lasting successful marriages, love their wives and have sex with them several times a week, and permit close friends to have anal sex with them when conditions and situations present themselves.

I hope you choose what is best for you, Bluespeedoz, and you'll always feel you've made the 'right' choice.

[post=264624]Quoted post[/post]

Hey Roystoy

Thanks for your encouraging response. You're right I've gotta feel I've made the "right" choice. He's definitely the right man for me - and maybe it would be great if I can come to terms with the idea and experience. I know I'm lucky to have such a close buddy - I love him just as much as I did my twin brother who died a few years back - and I know that regardless of what I decide our relationship will grow ever stronger.

KinkGuy · Nov 21, 2004

It takes a real strong man to address and explore their homosexual "side." Which to one degree or another, all men have. You certainly appear to be a man of substance and strength. BTW, it takes a "real man" to take it up the ass and admit that they like it!

KinkGuy · Nov 21, 2004

Yikes! flood control got away from me!

b1988 · Nov 22, 2004

Originally posted by Bluespeedoz@Nov 21 2004, 02:52 PM
Hi,I've had very regular sex with chicks since I was 13 and until I was 22 I thought I was straight. My best buddy and I have known each other since kindergarten and have that sort of man / man relationship only guys who trust, love and respect each other can have and understand. Three years ago he told me that he is bisexual and asked me if I would consider having sex occasionally with him. I guess most guys however strong their friendship was would have responded by putting a fist in his face. After careful thought I decided I wanted to explore the "gay" side of my sexuality personality with him and so we went ahead and had protected sex together. I discovered that I enjoyed "top" sex with him while he likes to be bottom and we are both very happy with our relationship. He has now told me that he would like as part of our love making to fuck me in the ass although he is not insisting I must let him. I'm not sure I'm keen on the idea because im my mind it diminishes my masculinity and because I hope to marry one day (I'm presently enjoying very regular protected loving sex with a chick my age (25). However there is a part of me that wants to say yes to my buddy, because I'd like to know what getting fucked in the ass feels like. Has any guy been in a similar situation or able to offer me some advice please about whether I should let my best buddy fuck me?
Sounds like you have the right mind set. I like being a top better myself, but have been a bottom for a few guys that I really cared about. One note, if you do, make sure that you use lots of good lubricant and try to relax. It can be challenging at first. I really like it with the right guy...sounds like he is the right kind of guy for your first experience.
As far as you masculinity goes....sounds like a bit of internalized homophobia to sort through. You're fine. You weren't less of a man after making love to your friend and I can't imagine how you will be less of a man if you allow yourself to experience with him what he has experienced with you. It's all good. peace,w

-_-

If you would be more comfortable respnding by email my address is bluespeedoz@mac.com

[post=264611]Quoted post[/post]

Mr._dB · Nov 22, 2004

My question is this -- if you feel that bottoming for your friend would somehow diminish your masculinity, do you feel that your friend's masculinity is diminished by bottoming for you?

Bluespeedoz · Nov 22, 2004

Originally posted by Mr._dB@Nov 22 2004, 08:04 AM
My question is this -- if you feel that bottoming for your friend would somehow diminish your masculinity, do you feel that your friend's masculinity is diminished by bottoming for you?

[post=264733]Quoted post[/post]

Hi there

I've asked my best buddy and hee says his masculinity isn't diminished because a. he loves to be fucked by me only and b. I always treat him with the love and respect he needs from me. But I take your point and that's a good reason for him to fuck me in the ass. -_-

Freddie53 · Nov 23, 2004

Originally posted by b1988+Nov 22 2004, 12:01 AM--><div class='quotetop'>QUOTE(b1988 @ Nov 22 2004, 12:01 AM)</div><div class='quotemain'><!--QuoteBegin-Bluespeedoz@Nov 21 2004, 02:52 PM
Hi,I've had very regular sex with chicks since I was 13 and until I was 22 I thought I was straight. My best buddy and I have known each other since kindergarten and have that sort of man / man relationship only guys who trust, love and respect each other can have and understand. Three years ago he told me that he is bisexual and asked me if I would consider having sex occasionally with him. I guess most guys however strong their friendship was would have responded by putting a fist in his face. After careful thought I decided I wanted to explore the "gay" side of my sexuality personality with him and so we went ahead and had protected sex together. I discovered that I enjoyed "top" sex with him while he likes to be bottom and we are both very happy with our relationship. He has now told me that he would like as part of our love making to fuck me in the ass although he is not insisting I must let him. I'm not sure I'm keen on the idea because im my mind it diminishes my masculinity and because I hope to marry one day (I'm presently enjoying very regular protected loving sex with a chick my age (25). However there is a part of me that wants to say yes to my buddy, because I'd like to know what getting fucked in the ass feels like. Has any guy been in a similar situation or able to offer me some advice please about whether I should let my best buddy fuck me?
Â Sounds like you have the right mind set. I like being a top better myself, but have been a bottom for a few guys that I really cared about. One note, if you do, make sure that you use lots of good lubricant and try to relax. It can be challenging at first. I really like it with the right guy...sounds like he is the right kind of guy for your first experience.
As far as you masculinity goes....sounds like a bit of internalized homophobia to sort through. You're fine. You weren't less of a man after making love to your friend and I can't imagine how you will be less of a man if you allow yourself to experience with him what he has experienced with you. It's all good.Â peace,w

-_-

If you would be more comfortable respnding by email my address is bluespeedoz@mac.com

[post=264611]Quoted post[/post]

[post=264723]Quoted post[/post]

[/b][/quote]

I have never tried anal sex. The first questions are for quys only.It is talked about on this site. I know what blow job feels like though. I understand what the guy doing the fucking gets out of it. But does the guy being fucked in the ass also have an orgasm. If so, how is it different from orgams form Jerking off and having sex with a woman. Also those who have experienced it say it is painful at first. Why does it quit being painful? I am looking for answers other than oh it feels good or it doesn't hurt. I would like some specific answers. I know that the prostate exam does't usually do anything for me. I have had the prostate "milked" for some tests. It wasn't cum, it was a very clear liquid and needed to be tested for infection.

Ladies, how is being fucked in the ass different from being fucked in the vagina? Is the orgasm different? How is it different?

I have heard such different things and I am curious. I figured that people on this site would be honest and tell me. Right now I am not in a position to try this. never mind the reasons. I just can't try this right now. But I don't know about the future.

Thanks for replies.

B_DoubleMeatWhopper · Nov 25, 2004

First of all, congratulations, Blue. I'm not congratulating you for having sex with your friend, but for coming to a realisation about yourself that some never reach or others try to deny. You've tried it, you liked it: that's great. Now comes the next big question: are you a top, a bottom, or versatile? All three are, of course, viable options. I am a top. I have never bottomed, nor have I ever desired to, but I would not hesitate to do so if I met the right guy and he wanted me to. It sounds like you've met the right guy, and though he doesn't insist on it, it's pretty plain that he would like it if you offered his ass up to him. Some dudes never meet the right partner. Are you prepared to pass up this opportunity to share yourself with someone you genuinely care about? Bottoming might not be for you, but then again, you might surprise yourself. Besides, isn't it worth some discomfort to let him know that you respect him? You equate being a top with masculinity ... well, your friend is a man, too. Give him the opportunity to experience with you what you have experienced with him. You've entered a period of self-discovery, dude. If you have even idle curiosities about things like bottoming, now is the time to explore them. That's my take on the situation. Then again, I might be full of shit. Ultimately, the decision is yours. Make a decision that you can live with.

13788 · Nov 28, 2004

dayne: I am a top and enjoy being a top in sex with a guy. About every five or sex years, I get the desire to bottom. It might take a couple of years to decide who I will bottom with. When I do, does this affect my feelings about my masculinity? Not at all. If I want a woman, I'll have a woman. I am in bed with a man because I want to be a man. When I take a cock up my ass, it is because I am with a man and he is doing something only a man can do for me. I let myself enjoy the moment for what it is and don't compare it with anything else.

D_Barbi_Queue · Nov 29, 2004

Blue - do you find that it has affected your relationship in any adverse ways? I was wondering b/c I have been bi-curious for quite a while but have yet to have an experience with another girl. My lifelong best friend stepped up and said she had no problem fooling around with me, but i'm afraid that it might hurt our relationship. We got way back though - I literally can remember her being potty trained (she's a few years younger than me).

madame_zora · Nov 29, 2004

Blue, being a bottom, even for experimentation, could and should be a lot of fun for you. While I am not a man, I have experimented extensively with anal play with my lovers. The only men who don't absolutely LOVE this are just too scared to try. The prostate, when massaged properly, will produc massive orgasms, very different feeling than from traditional sex or jacking. Since women don't have them, out experience in anal sex isn't very relevant to what you'll feel. I can tell you because I've seen firsthand the effect of this kind of stimulation on a man, and it's pretty incredible. Most men will quickly get to a point where they prefer this to sex the "old way" which is bad news for me! I think if you are fortunate enough to have someone with whom you are already so intimate, this one more thing could turn out to be less trauma and more fun than you're expecting. I hope so.

Texass, as women we usually don't have sex separate from emotion. I would take things very slowly with your friend. Sex will definitely change your relationship in a profound way, of course the two of you get to decide how, but that will take a lot of open communication. Oh, and your husband will be affected too, and HIS relationship to her. Are they friends now? How will you feel if you come home one day and she's there? Is it weird now? Would it be weird then? These are just some things to think about, I had a couple three-way situations years ago when I was in a relationship and they always seemed like more trouble than they were worth, but I know plenty of people feel differently, so I'd just suggest thinking it through carefully to make sure you get what you actually want out of it.

D_Barbi_Queue · Dec 2, 2004

Originally posted by madame_zora@Nov 29 2004, 08:37 PM
Texass, as women we usually don't have sex separate from emotion. I would take things very slowly with your friend. Sex will definitely change your relationship in a profound way, of course the two of you get to decide how, but that will take a lot of open communication. Oh, and your husband will be affected too, and HIS relationship to her. Are they friends now? How will you feel if you come home one day and she's there? Is it weird now? Would it be weird then? These are just some things to think about, I had a couple three-way situations years ago when I was in a relationship and they always seemed like more trouble than they were worth, but I know plenty of people feel differently, so I'd just suggest thinking it through carefully to make sure you get what you actually want out of it.

[post=265278]Quoted post[/post]

As always MZ, you bring up a lot of good points. In our particular relationship, a lot of those complications wouldn't apply. I currently live in New England and she lives back in Tx. We only get to see each other about once a year when I can make it back home to Texas, and it's been that way ever since I got married so no relationship has ever really developed between my friend and my husband, except an occasional "Hello" on the phone before he tosse it over to me. She is also happily married with 2 boys so this experience would really only be just "and experience" for the 2 of us and not something that would continue.

Her husband would be totally fine with it and in fact encouraged it when I was there visiting last May. Had I not been fat and pregnant (the mentality of all pregnant women ^_^ ), I might have even taken him up on the offer of surprising her in the shower (which was the first time that I felt sexually attracted to her - otherwise I've always thought of her as a sister). It would only be a "she and I" thing and neither husband would be involved in any way whatsoever except the knowledge of it. Sometimes I think it would be weird or awkward, other times I think it would be great. That is my impasse.

madame_zora · Dec 2, 2004

Ahh, well that does shed some new light on things, if she's not regularly in your life. I guess I'm a bit of a humbug about it all because I did a somewhat similar thing, having a 3way with a b/f and a very dear old friend. It turned out awful, she and I ended up not liking it, she ended up hitting on my b/f and none of us are now on speaking terms (not just because of that, but it played it's part).

If you and your friend are both enamored of the idea and it's just between the two of you, I can't see where the harm would be there, might make for a nice yearly visit home! I wish you the best in your self -discovery, and hope you'll feel okay to share your results if you decide to go through with it. Luv, Jana

13788 · Dec 2, 2004

dijstra:

Originally posted by TexAssgirl@Nov 29 2004, 10:10 AM
Blue - do you find that it has affected your relationship in any adverse ways? I was wondering b/c I have been bi-curious for quite a while but have yet to have an experience with another girl. My lifelong best friend stepped up and said she had no problem fooling around with me, but i'm afraid that it might hurt our relationship. We got way back though - I literally can remember her being potty trained (she's a few years younger than me).

[post=265209]Quoted post[/post]

Tex...I fucked my twin brother and we're just stronger for it...we did it cos we wanted to find out what it was like and cos we trusted each other to say fuck off if it wasn't OK...it was and though i don;t think we'll do anal sex again it was worth the experience...we trust each other implicitly so I suppose thats the key.

Dij

Bluespeedoz · Dec 2, 2004

dijstra said:
TexAssgirl said:

Blue - do you find that it has affected your relationship in any adverse ways?Â I was wondering b/c I have been bi-curious for quite a while but have yet to have an experience with another girl.Â My lifelong best friend stepped up and said she had no problem fooling around with me, but i'm afraid that it might hurt our relationship.Â We got way back though - I literally can remember her being potty trained (she's a few years younger than me).

[post=265209]Quoted post[/post]

Click to expand...

Hey there,

No our relationship is real strong and not adversely affected by reluctance to be fucked by him in any way. But that's our situation and not yours and so I imagine your relationbship could be hurt if you go ahead. I think you should talk things through before deciding whether or not to fool around with your best friend. And by the way my best buddy seduced me last night and I let him fuck me first before I fucked him. The sex and orgasms were fantastic and I feel absolutely great. I just didn't realise what I was missing out on.

D_Barbi_Queue · Dec 2, 2004

Originally posted by Bluespeedoz@Dec 2 2004, 02:56 PM
But that's our situation and not yours and so I imagine your relationbship could be hurt if you go ahead.
[post=265675]Quoted post[/post]

Is there anything specifically that made you say that?

oh, and congrats! glad you enjoyed it. ^_^

Sex with my best buddy.

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