Dear Richard: The Spirit Is Willing, but the Butt Isn't
By: Dear Dick
2.24.2012
Dear Richard,
I'm 25, and I've had sex with some guys since coming out at 18. I've even had a couple boyfriends.
The one thing I haven't done with any of them is have anal sex. I've done other guys, but no one has successfully done me. I want to, and when I watch guys do it in porn I think it's really hot and wish I could be one of those guys. But the two times I tried it didn't go well. My first time I was stupid and used spit, so it hurt a ton and didn't work. The second time I just couldn't loosen up and the guy got discouraged and left.
Is it possible that I'm just not able to? And if I can't do it like the guys we see in a porn, will any guy want to date me?
Desperate to Do It
Dear Desperate,
In theory it's possible that you "can't" have anal sex, but unless there's some medical condition going on that's doubtful. What's more likely is that you anxious about anal-receptive sex, and that's totally normal. Even the most skilled power bottoms have admitted being somewhat nervous on their first outings. But here's the deal: You're sex life doesn't end in your 20s, it only gets better. Sexually speaking, we constantly grow and evolve so just because you aren't comfortable doing something now doesn't mean you won't become a master of it in a month, a year, two years, or a decade later. That's one of the things that makes our lives exciting.
Sure, some men consider themselves "naturals" when it comes to this subject, but don't get caught up in what you think you “should” or “shouldn’t” be able to do in the sack. That won't help things. Neither will comparing yourself to porn stars. They're professionals at what they do, so they have experience with loosening up and downing a dong. Plus, there's a lot of off-camera prep time you don't see when watching a scene, so for all you know it took that model a good hour before he could ride the baloney pony like a jockey at the Kentucky Derby.
As for the technical side of things, use lube. Lots of it. 
Don't be cheap about that detail. The more lube the easier things will be.
Use your fingers. Make sure they're well-manicured because you don't want your fingernails scratching anything down there. Play around with yourself. Get to know what one feels like inside you, then two, then offer some repeated motion. You might also consider buying a dildo of reasonable size so that you can try it on yourself, at your own speed. Practice makes perfect, and while it won't remove all the anxiety from an encounter with a real man, it will instill confidence that it is possible for you to do it.
If you're with a man, consider being on top and sitting on the schlong. That way you can better control the position, speed, and thrust. If that doesn't work, mix it up. Sometimes a man's penis shape and size can feel great going in one way and painful from another angle. Experiment to find what works.
Keep in mind that great sex starts in your imagination. When you feel intensely connected with, and aroused by, another man the experience can be mind-blowing. It can allow you to relax and enjoy yourself. So the key is finding a man who makes you feel safe, sexy, and horny for it.
That said, don't assume every top is amazing. Some guys just don't get the attention to detail that's needed when it comes to prepping another man, or how to adjust the action if things aren't going well. If you don't like something, tell him. Don't be snappy and bitchy. Offer a suggestion for how he can make things better; again, practice will help you have that knowledge. This is important because a good top will make you feel more than just comfortable—he can make your toes curl and your head spin with delight. It may be difficult for you to imagine that, but you haven’t hooked up enough to know good sex from horrible sex. If you're open to trying—and it sounds like you are—finding that deliciously perfect partner will happen.
Finally, learn from the bad experiences. Know what went wrong, and also think about the other guy's reaction and how that affected you physically and emotionally. If you can grow from those moments you'll not only learn the tricks of a bottom, but become a stronger, more satisfying top.
Dear Richard is not a medical doctor, a licensed psychiatrist, a counselor, a reverend, or a rabbi. He has not been evaluated by the FDA, the CDC, or the BBC, and his words are not intended to diagnose or treat any condition. The information is for educational purposes only and it not intended to serve as medical advice.
Dear Richard does, however, love hearing from you and answering your questions. Leave a comment or send him an e-mail.
Images: Photos.com
Comments
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When I was about 18 the first guy that I had anal sex used Vaseline and he slowly inserted the head of the penis. Then he slowly inserted the penis up my ass and then let it stay there so I could get use to the feel of the penis. And he would ask me if I was ready to let him pull it slowly out and slowly back in. He would stop every once in awhile with his had penis till I got use to the feel of it. Then he asked later to see if I wanted him to go a little faster. After awhile I was now getting use to a slow fuck. It took me some time to get use to the penis going back and forth in my butt. Then the guy asked me if I would like for him to go faster. He only would go faster only after I've gotten use to the feel of his penis. When I was ready he went as fast as he wanted and then he came. I learned different sex positions that I liked. This way it would be easier for me to have sex. I didn't care for lying on my stomach. We changed to spooning and then later I would learn to ride him like a cowboy. Then I learned to do it doggy style. I eventually found my last position was on my back with my legs spread open. He cradled himself in between my legs with my heels of my feet on his bare ass. He rocked me slowly and then he got a little faster and then faster till he came. Tell the guy that you want to go slowly. Don't let a guy rush you into having sex by shoving a hard penis up your ass. You want to enjoy it. You don't want to have a painful experience in having sex. Take your time and enjoy each other.
You said that you tried it with some guy who got frustrated and just left. Bottoming for the first time is NOT something you should do with a one-time trick because they don't give a shit about you and they will not be patient with you. You said you've had boyfriends before, and they are the ones you should be trying this with. You need someone who will be patient and responsive to your needs. It takes a lot of trial and error the first time for some guys. It did for me, and my boyfriend was okay with that, and he got the pay off in the end (lol, pun intended.) Also, Dear Richard is right. Sitting on it instead of allowing him to be on top of you makes a HUGE DIFFERENCE! This is another aspect that a one-time trick may not be happy or flexible about. Going at your own pace is key, and sitting on it allows you to do that. It hurts like a mother fucker at first, and you need to be moving at a pace that is comfortable for you to manage that pain. Only you can do that, and a boyfriend will be sensitive to that. I hope this helps.
This really has not much to do with the subject, however to be the bottem takes talent... u must be clean and making some noise helps the pain.... Im in love with someone I work with not sure how he feels about me alot of mixed signals, he is openly gay any advice would be helpful cause im goin crazy.
Is so interesting to find out about what bottoms goes thru,WOW! so much work. and to find out too that Tops believe they are powerful , Dalings, just enjoy the passion-sensual-erotic kissing touching, the foreplay the discovers of each body and it all fall into place. must say breathing is very important (inhale when his cock goes in, and exhale when he is on place) after that is heaven.
Kiss
well, mt first time was when I was a teen ager. A friend down the street was tell me abot some frienda that he had. we were in the woods and he was talkingabout puting a dick in some ons ass. we did the just rubing in the ass, so I was not u[set about going further. Well, hern he put in in, it hurt like hell. an I made him take it out. He thought that he hurt me which he did, but I wanted to have him put his dick im my but. Well it hurt aging, and we only used spit, but once he was in, it started to feel good. he fucked me and I came by being fucked, so I was sold. I am a top but is still love being fucked it is so special.........
As a young teenager, I just loved the feel of having something in my butt. I'd use anything that looked like it would go in. Continuous play allowed some really large items to gain entry. To this day I am able to take up to a 10" circumference.
Lubrication is key. I've never used nose candy, just have that insatiable desire to be filled to the max... and then some every once in awhile.
-I pan gay.com articles fairly often for being shallow, silly, and non-informative. This is one of the best I have read. Congratulations Richard! Very good useful advice--including from many who replied. Cheers, JD.
Never had any kind of anal sex that wasn't intensely painful. Including dildos, fingers, etc. Didn't matter how much lube was used. After 25 years of trying, I've just given up on sex. It's not very much fun anyway.
I was lucky that I found a considerate top. He eased me into it.
I am a total bottom and I have had a few guys 8 to 9 inches .Foreplay foreplay and lube lots of lube , And poppers, Poppers. With poppers you can take any size and love it.
am new here,and am 21, how can i get someone that will take me as his bf, any country pls i really need it.
What do you need. I will try to help you in anyway I can.
conntect me.
mitchellcheek@live.com
Follow all the advise above (practice by yourself, buy a dildo, use plenty of lube, sit on top of your fucker's penis, etc.) The one thing nobody mention is that when you sit on top make sure that your shoulders are kept down since tensing them will keep you tense all over, including your ass; try this little trick, it really works.
Dinner with a nice bottle of wine (to relax you) share before sex does help a lot too.
Am a total bttm and my BF wants me to deep throat his dick which is like 9.5" but its very hard to do without me gagging/vomit is there a method of being able to without gagging , I have seen vid with guys doing it so well but no matter how I try can't seem to not gag any advise ?
dude am 19 and i have done a 9 inch and what i can tell you is it takes practice giving a good blow regardless of size takes lots of practice so don't worry about it just give it some time and your body will learn to override the gag reflex ok.
and breath through your nose. It's physically impossible to gag if you breath through your nose becasue your airway is not being blacked that way. Its hard to master but it helps alot! GO SLOW
Donsternny, I totally agree that douching first not only cleans you out, but several douches in a row really loosens your sphincter up. There is an enema bag which holds the equivalent of about 6 douches and has a clip to control flow of water. You just let it flow until you are full. For the first few years I bottomed it hurt like hell, but over time I have become a SIZE QUEEN and the bigger the better. I have had several FB's with 9' and over, and quite thicker and they put me into nirvanna. I do prefer starting out sitting on the top and you can control the action much better. And yes, plenty of lube makes it so much better.
I even got to the point of sitting on my 12" dildo rather proficiently and could take it all the way to the rubber balls. And of course a little nose candy goes a long way in loosening you up!!! And makes me HORNY as hell. LOL
Everything you had to say was great except the "nose candy". I don't care how relaxed or horny it makes you feel. The whole point of the article was to realize how anal sex and what positions feel good. If you are all doped up how will you ever know what truly works for you.
I started having anal (bottom) sex when I was in my early teens (normal boy-boy experimentation) When I was young and in the Air Force I had a partner who was very small, and we had flip sex almost every day. After we parted, I met a man who to my eyes at the time was huge (he was at least 9" but we never measured) He was an extremely skilled top, and he drove me wild with passion. Lube was always used, and poppers back then too (1976) Ever since then, I have preferred bottoming, but will top in certain cases.
The moral of the story is that it is on the top, not the bottom, to have the skill to be a good lover. FOREPLAY, FOREPLAY, FOREPLAY... lube, and yes, unless you have positive proof of your sexual partners HIV status, a condom (lubricated) is a must.
Good Luck, have fun and play safe I am poz now by the way... didn't start playing safe soon enough.
Scott
good advice guys. yeah just buy ya a dildo and enjoy. it will cum to ya. hang in there and be patient have fun and enjoy!!!
WOW.....nobody here talks about graduated dildo/butt plug sets? I used to seldom be a bottom... but then I bought a set of 3 graduated dildos/butt plugs. I would douche and then slowly work the smallest size in.....then sit on it for about then 30 minutes while working on the computer. Then I would do the same with the medium. Finally the large. I could only go so far the first time. Next night I repeated the process.......I got farther with #3 but still not all the way. Finally on night 3 I was successful.
Now I am able to start with the medium and then take the large.....I do this about once every 2 weeks......guess what? Being a bottom is nothing for me now and my lover loves the fact that I went to the trouble just so he could enjoy my clean tight ass.
The asshole is a muscle boys.......you have to exercise it to keep it limber and toned. Use it or lose it.......but don't abuse it!
Buy some Analeze and you'll be fine.
LOL lots of comments on this one already but yes, Richard has it right. My boyfriends penis is actually just the right size. Big but not to big. I think he's like.. hmmmm... 6 inches and when he takes Viagra (he's 40 and I'm 18) since of my smaller body stature it starts to get to big but I will have to say that it took me about hmmm... 3-4 months to be able to take him in successfully and that's without a condom. If he even wears a condom its a little bit more harder to take him but yes, to anyone who shall ask and criticize me, we both got tested at the same place at almost the exact same time (he went to get tested first) and we had the same person to test us and she told us both of our test turned negative like the second it hit it. She also knew I think that were were a couple since she then handed me a small baggie of condoms LOL. She was a very cool-cat doctor I think. :)
well i was with 2 lovers for a total of 24 yrs. i reserve anal sex for a very serious commited relationship & that only. i do this out of respect for myself and him. my rule is this, if u can out last my throat, then u can have it simple. i deep throat very well, most guys r happy with that. the ones that r not r just jerks anyway & not worth my time. their do have to be a 2 way street tho. it does take 2 to make anything work. it is not that i don't want to. but i like to have respect for myself and my mate. people want to much to fast. whatever happened to stop and smell the roses anyway. my men have always benn very happy and well taken care of. i do not feel the need to conform to whatever. also it does make anal lots more romantic and very very special.
I am versatile, generally a top, though to be able to throw your sweet legs up into the air and be on the receiving end of anal intercourse is one of the best feelings that can be. To elaborate on what some fo the other guys here said, there is no rush. Play with his little hole, use finger, fingers and tongue. Massage his hole for him. Take your time. He'll be asking for your largess before you even know it !
I first enjoyed anal sex with a man whose penis was less than 6" and uncut. What a smooth ride, though I think he used only saliva fop lube. We weren't loverss but repeated from time to time. My only passive orgasm was with a lover who was HIV+ and we had never done anything but masturbate together. His penis was the same size as mine, 17 cm. (about 6.75") and cut, and he used a lubricated condom, which was just right. He never would do it again, saying he felt like he had taken advantage of me. I kept telling him I didn't feel that way at all. Now he has been dead for 17 years and I am still negative and virtually celibate: I am very particular about who gets in.
I find that being on top and taking it at my own speed in the beginning is very helpful. ONce in and going in and out smoothly, let your guy take over and go for it :) It should always be exciting and a great experience for both not just one. I'm the type that has very intense orgasms, so if the guy is in me and I'm comming, he's going to get the squeeing of his life :) Good luck to everyone out there!
I have a tight ass and require a lot of time and lube before getting fucked. The problem is most potential partners will not spend the time needed to make sure that am ready. They try to ram it in, it hurts like hell and is a real turn off. What is the big hurry anyway? Instead of douching I try to have a good dump before I have sex. As part of foreplay my partner and I shower together using soap to open up and make sure each others ass is clean. If anal sex is out of the question I find that massaging the prostate works just as well. Not everyone can be a bottom. Spend the time to find out what else turns on your partner.
Robert.... I am the same way very tight ass and even with a bf for more than 4 yrs its still takes time for him to get in at 1st , 90% of top belive that because we're bttm is ok for them to just jump on and jam it in like we have no feelings as for me its take lots of lube and sweet talking for my BF before he's can even get the head in and sometimes I belive he gets upset that its so hard for his dick to get in but thats just the way it is .
Being a bttm isn't as easy as most guys think we have to be able to stand the pain which turns into pleasure but for me I like being submissive bttm for my BF because we have alot of foreplay and dress up which makes it not just about sex but love/romance .
I'm 99% of the time a bottom. Usually, I don't use lub, just spit and i love it!
I am 43 and have been fucked a lot in my life, but it still always hurts at first. I enjoy myself much more if the guy is no more than 6.5", but most guys are much larger than that. Prep is so annoying - the douching, the relaxation techniques, ugh. I am so envious if guys who can bottom easily at a moment's notice. Some don't even douche and never have an issue. If I didn't douche, it would be a disaster. :(
lmao, you guys are doing something very wrong, my bf and i have been doin the nasty for 3+ years now, hes 9.5 x 8ish uncut, and i am 8.5 x 7 cut, we are bother versatile, we use lube, but not in the amounts you guys are referring to, and we enjoy ourselves, and i know firmness is not a problem ,because we both work out 2 to 3x a day, so we are both in tip top, excuse the pun shape, wish i could tell you whats wrong, but i cannot.
You have got to be kidding about 9.5 x 8 and 8.5 x 7. Really? 8 inches wide?! I'm questioning the length, but if your cock was 8 inches across, it would be a giant square, not a cock. I think you need to go back and remeasure, honey.
I meant to say I'm NOT questioning the length.
maybe he means length by circumference.
All you need to do is google and you will find that the vast percentage of men have penises that are between 5 and 6 inches long. Only 5% of men have penises longer than 7 inches. Maybe you guys are using a centimeter ruler...
Many guys measure wrong (measuring from the underside, or measuring on top and shoving the ruler into their abdomen, and in both cases generously rounding up)... unfortunately, this only leads to many normal men thinking that they are undersized.
I never understood why people exaggerate... people you aren't sleeping with don't care, and people you are sleeping with will find out the truth anyway right?
I must be one of the five percent then !
Getting into anal play takes practice and lots of lube , I just can never understand why men want to use spit that will only make penetration hard and cause soreness after if not done with careful , my advice to any man who is getting penetrated for the 1st time is relax,breath and make sure that you use lube to enhance the process .
Thanks for the advice. I printed the page but am not giving up my cherry-O until am married....#thuglife...ha
"Can we talk", to borrow a phrase from Joan...
Richard made an interesting comment in mentioning that a lot goes on "behind" the scenes in porno movies. I've often thought that and would like to know exactly what prep routine those guys go through! Please be specific; don't worry, none of us will blush beet red!!!
When I started having man-sex, I too had a difficult time with this issue. In fact, my first experience was a total disaster. I felt that I had hit rock bottom in more ways than one...
Some time after I met a man (Canadian, and they are sooo affectionate) and he started to stimulate me with his finger and progressed to finger-fucking. This used to drive me crazy and still does! The sensation of prostate stimulation is incredible and I recommend that this is how you start...
After a number of "work-outs" with him, he suggested that we try fucking. Naturally, my perception had been clouded by my initial experience and was hesitant to even try, butt with patience the mission was accomplished! I might add, this was before the advent of AIDS and the need to use condoms. He was uncircumcised, so the combination of thrusts and the sensation of his foreskin moving back and forth while fucking was absolutely incredible!
Let us know how it works out for you! Remember to provide a detailed description, written in such a way as to appeal to our prurient, lustful and envious interest...! Good luck, bro!
.
just want to say the only real thing I know of as far as porn prep, is that they do a lot of the get him right to the edge and then back off, let him soften and start over, so the final "shot" is worth it. Also, Anal Douching. Ever watch porn and wonder how they can pound and pound the lil bottoms, and still end up clean as all hell, even in some porn going straight from Ass to Mouth? well in these cases anal douching was smartly used...it cleans everything out and makes it so you don't ever have to worry about "messiness"
A sensitive matter to be sure, butt nuttin´like gettin´to da butt of the issue... Yes, you are correct: no signs of "messiness" and ass squeaky clean ass can be -- all from a bottle of "Summer's Eve"! hehe!
Dear richard I prefer u go ur way and buy lubricant whenever u ar going to av sex with ur boyfriend use
# 1 rule, slow down. And lots of lube. Douche sure helps. If the dick ain't hard its not going to work. I have found that for everyone laying down on your stomach with one leg ahead of the other so there is a leg split is the easiest for everyone, really lets you adjust inch by inch easily, its also the easiest for going deep later on. But the biggest thing I have found through the ages is that a good top makes a great bottom and a good bottom makes a great top.
Desperate, I sometimes have the same problem. It's not that I don't want it and want it bad but sometimes the top just isn't hitting me at the correct angle and he kind of runs a ground to borrow a nautical term. I think it's because I have a kind of bubble butt with a lot of curve in my lower back which causes the entry to be at a different angle than guys often anticipate. Getting on top as Richard suggested is a great idea for you. That way you control the angle, pressure and speed.
Desparate: One trick that really works for me is to get my ass really relaxed before I even let my top touch me down there. The method I use also takes care of the douche part. They sell hoses made specifically for this--it has the correct tip and everything. (Google 'The Shur Shot' or 'Travel Shur Shot') It attaches to your sink or tub plumbing. Turn on the water and and adjust it so that it is warm (I find the warmer the water, the better, but not like real hot). While sitting on the toilet, insert the tip, let in about as much water as a full douche bottle and then remove the tip, but squeeze so the water doesn't run out. After a few seconds, relax and evacuate. Repeat this a couple of times until you're clean. Then place the tip against your hole without pushing it in and let the water run against the muscles. After a minute or so, your hole should relax to the point that it will open up with no effort when you insert the tip once again, but this time stay completely relaxed and let the water run out around the tip. Just sit and enjoy the great feeling of the warm water rushing over muscles of your hole. In no time those muscles will be so warmed up and relaxed you'll believe you can take anything your top has to offer and it won't take much time at all for a caring top to get you completely opened up and ready for his tool.
Ps. I agree with Steve; when you're ready, sitting down on your top's tool is a great way to not only get him into you, but it will let you get him deep inside you on your terms, not his. Take your time and don't forget the lube! Once he's in deep and you're comfortable working it, then the sky's the limit--enjoy and lose yourself in the moment. The more you lose conscientiousness of the world around you and zone into the sex you're having, the more excitement you'll generate between the two of you and that will make the whole experience a really good one.
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