From the bottom up

[TruthBTold]

Hi. I know this may sound like a silly question, but I thought I would just go for it. I have been a top my whole life, about 50 years. It could have been the result of fear (the one time I tried was a long time ago and it mostly just hurt) or just because I tend to take control when I am with a versatile guy so I ended up as the top more times than not. Either way, I have started to feel lately like I would like to have some bottoming experiences. I have a few (at least for now) questions. Other than letting the top take control, how do I know if I am enjoying a bottom experience? When I top, I know because because my cock feels good and the bottom is letting me know that he is enjoying himself. But what things happen to you when you bottom successfully? Does your hole feel good? Do you feel dizzy as if your body and mind are disconnected? Also, are there things I can do which would make it more likely that I will have a better bottoming experience? Finally, I will probably be with an escort when this all happens, is there something I should look for him to do to help me out. I know this sounds stupid but I really am starting from ground zero. Thanks for any ideas you might have. If you feel more comfortable, message me.

[jjkrkwood]

Hi. I know this may sound like a silly question, but I thought I would just go for it. I have been a top my whole life, about 50 years. It could have been the result of fear (the one time I tried was a long time ago and it mostly just hurt) or just because I tend to take control when I am with a versatile guy so I ended up as the top more times than not. Either way, I have started to feel lately like I would like to have some bottoming experiences. I have a few (at least for now) questions. Other than letting the top take control, how do I know if I am enjoying a bottom experience? When I top, I know because because my cock feels good and the bottom is letting me know that he is enjoying himself. But what things happen to you when you bottom successfully? Does your hole feel good? Do you feel dizzy as if your body and mind are disconnected? Also, are there things I can do which would make it more likely that I will have a better bottoming experience? Finally, I will probably be with an escort when this all happens, is there something I should look for him to do to help me out. I know this sounds stupid but I really am starting from ground zero. Thanks for any ideas you might have. If you feel more comfortable, message me.

 

I have had this conversation with many of my contemporaries who have identified themselves as TOP for most of their adult life, but it seems as they age, problems obtaining erection or orgasm often accompany older age, and they find themselves leaning more to Bottoming as "default". Now, I am not speaking for the entire senior male gay population. I am relating what guys of mature status have told me. It kinda makes sense. Personally, I have never been a fan of anal, so I have always been, and remain just a Cocksucker......

[zeyfur]

I always use the douche before bottoming. It makes me relaxed and I stop worrying about accidents. For me I really have to be turned on by a top otherwise I don't seem to relax enough to take them without discomfort. Also I ve found if you can give the top a good blow job he will be rock hard and can direct his cock better. Use lots of lube. For me it s about trust. I am giving my ass to the top and he becomes a part of me. It s the intimacy that turns me on.

[JT Brooklyn]

You'll know within 3 minutes!

 

Hi. I know this may sound like a silly question, but I thought I would just go for it. I have been a top my whole life, about 50 years. It could have been the result of fear (the one time I tried was a long time ago and it mostly just hurt) or just because I tend to take control when I am with a versatile guy so I ended up as the top more times than not. Either way, I have started to feel lately like I would like to have some bottoming experiences. I have a few (at least for now) questions. Other than letting the top take control, how do I know if I am enjoying a bottom experience? When I top, I know because because my cock feels good and the bottom is letting me know that he is enjoying himself. But what things happen to you when you bottom successfully? Does your hole feel good? Do you feel dizzy as if your body and mind are disconnected? Also, are there things I can do which would make it more likely that I will have a better bottoming experience? Finally, I will probably be with an escort when this all happens, is there something I should look for him to do to help me out. I know this sounds stupid but I really am starting from ground zero. Thanks for any ideas you might have. If you feel more comfortable, message me.

 

The Upside it's less Work! "How do I know If I am enjoying Bottoming"? Let me put it this way... You will damn sure know IF Your Not!

[doitb4ugo]

The two major factors for me are: am I relaxed and really wanting that cock up my ass...and did the top get me physically ready to receive...

 

I need my ass played with and opened up a bit for anal not to hurt (even though sometimes I just want to be taken without foreplay, in which case I want the pain). I find that rimming helps alot in the desire department.

 

As for liking it, I melt emotionally as soon as the top runs my ass with his cock.Often I like to have the top rub me and let me push myself onto him...allowing me to be in charge of penetration...

 

Having plenty of lube makes me more comfortable about it but have had many times where almost no lube is used.

 

Best advice, wait till you want it sooo bad and make it happen....good luck, I can't imagine life without a good fuck.

 

P.S. As recent as yesterday....don;t hesitate to ask the top to "take it out" if you tighten up...it is not easy to relax after you panic. No shame in starting over...

[vabballfan]

A lot of it is mental

 

If the top knows what he is doing and his cock works your prostate you'll know when it feels good.

 

I was top only for the first couple of years of having sex with men. Partly because the third time I was with another guy he just shoved his cock in when he told me he wanted to fuck me. No real preparation and he wasnt' particularly big - 7" medium thick. It hurt so much that I made him stop. I didn't try bottoming again for almost 5 years.

 

And it was the person that I was with at the time that made me want to bottom. He was a total top - he had tried bottoming about a half dozen times and he never liked it - he was evidently not built to bottom. And we fooled around with just oral, touching and kissing for about a month. He was actually very well endowed - 9 inches long, 6 inches around and uncut. When I finally told him I wanted to try bottoming for him, he took about 20 minutes to get into me that first time. And after about 5 minutes of very slow fucking, I started to really enjoy it and basically egged him on even backing onto his cock. Then I got a big surprise and came without touching myself. Then I got on my back and told him to keep fucking me until I came a second time. He knew it was my first time bottoming so he was truly amazed I was so into getting fucked by him. I guess he's the one that made me into a size queen. But it was really mental - I wanted him to fuck me so much that I made it happen.

 

And to be honest with you ask the escort you end up wanting to pop your anal cherry if he has experience with first time bottoms.

 

But one thing for sure, a thick cock (not megathick, but thick) is a lot more comfortable to take than a skinny one...

[leigh.bess.toad]

A lot of good comments from people. For me, how do I know. I guess the surest way to know is after I get started and that wonderful first feeling of having the cock in my ass and after a bit of just getting started I'm screaming at him to fuck me for all he's worth. When it feel so good that I keep trying to get it in deeper and deeper. Of course the ultimate to know if you are having a good time is by cumming while he's fucking you, especially if you get that rare occurrence where it's hands free.

 

Prep is, as others have mentioned, important. Not worrying about making a mess can certainly take things off your mind and you can focus on the event. It does also open you up a bit to get started.

 

Playing with toys is also a good place to start. I also use toys as a way to make certain that I'm clean before hand. If after you clean yourself and then play with a toy, and it comes out clean, you can be pretty sure you are ready.

 

But relaxing and enjoying the experience is the biggest key. If you go in terrified, your butt will clamp up and be difficult to enjoy. At least that's been my experience.

[nycfan2003]

Usually I am not interested, because of the pain. But I met a regular in DC and I trusted him. It's the first time I felt absolute pleasure. I think it's part trust and part preparation, both on your part (douching) and the escort's part - taking his time, lubing up, and starting slowly.

[OneFinger]

http://www.companyofmen.org/images/icons/icon12.png You'll know within 3 minutes!

Actually, it's more like you'll know with 3 INCHES!!

 

I've never had a bottom experience where I've enjoyed it. Just not something I'll ever try again.

[JT Brooklyn]

Actually, it's more like you'll know with 3 INCHES!!

 

I've never had a bottom experience where I've enjoyed it. Just not something I'll ever try again.

 

Your defintely right about the 3 Inch Rule!

[nycguy]

I have been fucked four times in my life and not since I was 30 years old. Each time I shot without touching myself within 4 or 5 minutes. Each orgasm was the most powerful (distance and volume), intense and pleasurable orgasm I have ever had. I don't emotionally connect with being fucked. As I have gotten older, I have occasionally thought about wanting to repeat those memorable orgasms but I still don't want to get fucked.

[jgoo]

The advice given here of prepping the hole, use of plenty of lube, etc. are all useful to help make the experience enjoyable. While I do not bottom that frequently, when I do I find it also helpful to start off by sitting on the guy's cock rather than letting him take control. That way I am able to go as slow as I feel is necessary to get used to it and to have control over things. After that, we can move on to other positions and he can take over the "hard work".

[mistrmikey]

when u guys are getting "loosened" up - if the top is rimming you...dont you worry about health concerns? I just met up recently with a guy who LOVES rimming - total top- (and he's HOTTT as Hell!)- he went to town, rimming me (i didnt LOVE it, but its something maybe i would).... however, my mind took over with worry about disease and prevented me from enjoying the experience. Ultimately he got in, topping me(this only has happened 2 times prior) - but he realized the pressure was preventing me from enjoying it - really bummed me out. We ended up just playing afterwards - but i really want to please him too, and i know he likes topping.

 

Also - i asked if he likes the favor to be returned (on the rimming side) and he said "yea.." He doesnt normally bottom..but maybe i get him all horned up, he may give it up for me. Again, rimming an asshole i dont REALLY know, concerns me. He makes alot of "safe" comments - but given this dude's HOT body - i cant believe he isnt tappin alot of tail...

[+ sam.fitzpatrick]

Finally, I will probably be with an escort when this all happens, is there something I should look for him to do to help me out.

 

I'm sure this goes without saying, but be up front when hiring the escort that this will be your first time bottoming. My first two times bottoming were with escorts over 30 and they made sure to take things at my pace and they were great. The third time was with an inexperienced 20-year old (and six months later) and I learned that I should have been more up front with my inexperience level.

[Gar1eth]

The two major factors for me are: am I relaxed and really wanting that cock up my ass...and did the top get me physically ready to receive...

 

I need my ass played with and opened up a bit for anal not to hurt (even though sometimes I just want to be taken without foreplay, in which case I want the pain). I find that rimming helps

 

I guess that was what was wrong at the doctor's office when he performed the digital exam. I didn't enjoy it at all. But maybe I would have if he had relaxed me 1st and then done a little rimming before the exam.

 

Gman

[leigh.bess.toad]

I guess that was what was wrong at the doctor's office when he performed the digital exam. I didn't enjoy it at all. But maybe I would have if he had relaxed me 1st and then done a little rimming before the exam.

 

Gman

 

I guess that's how you can tell a bottom. When after the digital exam, you point out he missed a spot and ask him to do it again. With a couple more fingers this time. It was hard not moaning while he was doing it. And thrusting my ass back on his fingers.

[Lohengrin1979]

I guess that's how you can tell a bottom. When after the digital exam, you point out he missed a spot and ask him to do it again. With a couple more fingers this time. It was hard not moaning while he was doing it. And thrusting my ass back on his fingers.

 

And I thought I was the only one. Thanks for letting me know I'm not alone there, LBT. Mild und Leise indeed.

 

Regards,

Lohengrin1979

[Gar1eth]

I guess that's how you can tell a bottom. When after the digital exam, you point out he missed a spot and ask him to do it again. With a couple more fingers this time. It was hard not moaning while he was doing it. And thrusting my ass back on his fingers.

 

In all honesty, I've had a problem with well--hard to know what to call it--maybe chronic/recurrrent prostatitis--I've also heard it called prostatosis by one urologist or chronic pelvic pain syndrome--or while it's more common in females--interstitial cystitis--I frequently get soreness, often pain in the pelvic region right over the pubic area above the base of the penis. Many things can trigger it like ejaculating to frequently--but often it's the digital prostate exam. Last time I went to the urologist, I was already having a flare up--well after the exam it was worse the following day--and the soreness lasted 2 to 3 months--the pain waxed and waned during that period.

 

When I 1st learned about gay sex as an adolescent or young adult (ok I admit I was sheltered), the thought of bottoming "freaked me out". But I suppose in normal circumstances, I might have grown curious over the years as to what bottoming feels like and might have tried it. But if the urologist doing a gentle exam can put me in pain for several months, I figuratively shudder at the thought of the pain I would most likely go through if someone were intentionally trying to hit it/massage it by topping me.

 

Gman

[+ Shoreboy]

I was one of those people that was 100% top. I never even imagined myself bottoming....until one escort I was with in DC of all places, started with a very oily massage and kept tweaking my ass.

 

I loved it and found myself raising my ass to his finger and finally his tongue. He was patient, teasing and highly erotic and giving my virginal ass attention it had never experienced.

 

I was so turned on that I wanted to try bottoming right there....but he kept teasing me and working me into an anal fenzy.

 

He had slipped on a condom without me knowing it and then began his patient topping. Once his head was in I surprised myself and was the one who thurst my ass right onto his dick...and it was bliss.

 

I think it takes someone time, patience and a lot of teasing and any top can turn into a glorious bottom....I know...it happened to me

[Indigo]

Up until recently I would have never have considered bottoming but all that changed when I met a certain escort in London. The escort advertises as a versatile top and he had agreed that he would bottom with me. The day that we met met I found that he was so dominant in a hot and sexy way that I found myself turned on in a very new and unexpected way. Along with an overpowering and exciting demeanor ,he started giving my ass attention with his fingers and tongue, and before I knew it I had agreed for him to top me (safely of course.) He obviously knew what he was doing and suggested that I try to sit on him and slowly get used to the feeling. Surprisingly, I was quickly able to get used to him and eventually had the most powerful orgasm ever.

 

A few months later, I tried to bottom with someone else but I could just not go through with it. It was uncomfortable and painful. The person I was with was clearly not experienced enough to guide someone like me through another bottoming adventure. It just goes to show how important it is for the top to be patient with someone who is not necessarily used to bottoming. Since he was versatile I ended up topping him instead.

 

I will always hope for another bottoming experience like that unforgettable one in London.