1st time sex mishaps

[coryvale]

I have never had sex with a man--though I really want to try it one day. What were some of your mishaps, or things you wish you knew before hand? Thanks for the advice!

 

[MoaningMike]

If you're going to take it up the tailpipe, make sure your hole is clean! Use an enema and rinse well, there are plenty of tips online about proper anal douching. It's something nobody talks about, but they should. I wish I had known about it before I had anal, but it's not exactly something they teach gay teens in sexual education class!
Another mishap to avoid is using your teeth when sucking dick. Practice on a banana or carrot or dildo giving great head is a skill, and practice makes perfect! Always make sure you're clean before sex: nobody wants to endure smelly armpits or crotches.
If you're topping a guy, a mishap would be hurting him. Use lots of lube on his hole, finger him good until he tells you he's ready. If you want to, you can rim him. Unless he asks you to, don't shove your entire hard dick up his ass in one shove.
A big mishap is not having condoms and lube nearby. You don't want an STD, so play safe.

 

[desertboi]

If you're doing any ass play, make sure you use LOTS of lube.

 

[fetish]

I tried topping twice, but in both instances, my dick really can't penetrate the anus no matter how I tried, which is embarassing. How to actually do it?

 

[dd788snipe]

I tried topping twice, but in both instances, my dick really can't penetrate the anus no matter how I tried, which is embarassing. How to actually do it?

The bottom has to relax. You can start by messaging his hole then slowly sliding your middle finger in and out. Well lubed of course. Use lots of lube. Once he gets comfortable try putting in two fingers and slowly stretch the sphincter muscles out. Take it slow. You'll feel them relax. If you have a vibrating dildo handy that works also. Then slowly try to penetrate him with your cock. Communications is the key between both of you. I'm a bottom so that's where I'm coming from. Is you cock big? Good luck and welcome BTW.

 

[MoaningMike]

The bottom has to relax. You can start by messaging his hole then slowly sliding your middle finger in and out. Well lubed of course. Use lots of lube. Once he gets comfortable try putting in two fingers and slowly stretch the sphincter muscles out. Take it slow. You'll feel them relax. If you have a vibrating dildo handy that works also. Then slowly try to penetrate him with your cock. Communications is the key between both of you. I'm a bottom so that's where I'm coming from. Is you cock big? Good luck and welcome BTW.

Yes, great advice! Getting a bottoms hole primed for pounding is essential. When I top I love to drive a bottom crazy playing with his hole, you want him to be begging to get fucked! If your bottom doesn't own a dildo get him one, and tell him to practice daily. A vibrating dildo is even better, or one with a suction cup. The more a bottom gets used to an anal invasion, the easier he will be enter.

 

[jedi19]

The bottom has to relax. You can start by messaging his hole then slowly sliding your middle finger in and out. Well lubed of course. Use lots of lube. Once he gets comfortable try putting in two fingers and slowly stretch the sphincter muscles out. Take it slow. You'll feel them relax. If you have a vibrating dildo handy that works also. Then slowly try to penetrate him with your cock. Communications is the key between both of you. I'm a bottom so that's where I'm coming from. Is you cock big? Good luck and welcome BTW.

I find this info useful. I tried topping a few times myself. My main problem is the fact my cock isn't big but only avg 6 inch.

 

[flamingo]

I'd never had sex with a man until last summer. I was a bottom, and the biggest mishap I made that day was wanting it before I was really ready for it. Damn, it was painful, and my man was more assertive than I expected. My second attempt with a different man was embarrassing when he told me my hole was dirty. And my teeth have gotten in the way a couple of times when I was sucking cock. I've probably made every mistake possible, but I am getting better, and I am fortunate to have older, patient men who help me through the process. Sex can be very awkward, and not always as smooth as porn vids make it seem! One thing I've learned is the best sexual experiences don't require intercourse!

 

[MoaningMike]

I'd never had sex with a man until last summer. I was a bottom, and the biggest mishap I made that day was wanting it before I was really ready for it. Damn, it was painful, and my man was more assertive than I expected. My second attempt with a different man was embarrassing when he told me my hole was dirty. And my teeth have gotten in the way a couple of times when I was sucking cock. I've probably made every mistake possible, but I am getting better, and I am fortunate to have older, patient men who help me through the process. Sex can be very awkward, and not always as smooth as porn vids make it seem! One thing I've learned is the best sexual experiences don't require intercourse!

You've got the right attitude! It's important not to get discouraged by bad sexual experiences when you're starting out. Practice makes perfect, no matter what it is. It's a good thing forums like this exist, it gives men a chance to talk honestly about sex. It would be wrong to think that sexual mishaps are rare, I would bet that everyone has had something bad happen.
Your first time bottoming being very painful is likely universal. Being told that you have a dirty hole would be horrifying, and if you're human you won't naturally have a squeaky clean manhole! Learning about enemas and how to get clean is essential, its not like you're taught these things in a high school sexual education class!
The best way to learn to bottom is to practice by yourself. Buy several toys in various sizes, always use lots of lube, and start with the smallest one. One mistake lots of guys make is buying a big dildo and finding they can't handle the pain, or even get it all in. They get turned off the idea of getting fucked, when they really would've loved it if they took things in stages. Most guys who cum with something up their ass will have their mind blown by the extreme pleasure. Prostate stimulation will give you a harder and bigger boner, and make you cum much harder.
My partner now had been a total top before we got together, he had gotten fucked a few times and HATED it. It took lots of convincing, but I turned him into a power bottom. The trick was using dildos on him, taking it slow, and not shoving more in until he was begging for it. I'd make him get in various positions to see what he liked best. It would start with me working the dildo in and out, when he started thrusting his ass back and forth I knew he was liking it. The trick was to not fuck him with my dick until he had several sessions with the dildo When he would eventually lay on his back, usually with his legs on my shoulders, that was his sign he wanted to cum. By this point he was begging for it hard and fast, so I obliged. I loved watching him jerk off his big thick dick while the dildo fucked the cum out of him. The look on his face the first time he came that way was pure ecstasy. We did this maybe 8 times, and he loved it more each time. I wanted him begging for my dick, and it worked. The first time I fucked him he took it like a pro. Now he wants it all the time.

 

[dd788snipe]

Great advice MoaningMike.

 

[flamingo]

MoaningMike, thanks for sharing about you and your partner. I've been very timid about having something up my asshole. I'm not even comfortable about inserting my own finger. I've wondered if this would alienate my boyfriends, but no. One of them told me, "I didn't fall in love with your asshole, I fell in love with YOU.

 

[MoaningMike]

MoaningMike, thanks for sharing about you and your partner. I've been very timid about having something up my asshole. I'm not even comfortable about inserting my own finger. I've wondered if this would alienate my boyfriends, but no. One of them told me, "I didn't fall in love with your asshole, I fell in love with YOU.

Glad I could help! There was an article online a few months ago (I can't remember the source) about how there is a large amount of gay men who don't have anal sex. It was news to me! Their reasons were the pain, the cleanliness factor, diseases.
So you being hesitant to have even a finger up your ass isn't as uncommon as you'd think. I've never had bareback sex, and I don't feel like I'm missing out. Condoms are so thin that you don't even feel them anyhow, it's safe, and it's clean. The sight and smell of shit makes me sick, and getting it on my dick would make me puke. Some guys are unaware of how to properly clean their holes, especially guys who are new to anal. I sure wish I had been taught how to douche in sex Ed class in school when I was a teen! Teaching us gay boys how not to get girls pregnant isn't very helpful.
Before you have anal with your boyfriend, get used to playing with your ass yourself. If you're worried about pain, your finger won't hurt as long as you use lots of lube. You'll be surprised how great it feels. If you can't relax by yourself, you won't be able to relax with a partner. The best place to experiment is in a hot shower or bath. Start by washing your ass like normal, except this time insert a soapy finger and move it in and out and around. A shower or bath is relaxing to begin with, if not downright erotic. Rinse your ass of the soap, then apply some lube to your finger and go fuck yourself. I would be shocked if you didn't love it. I was having fun with my hole before I was buying dildos and vibrators, so I had to find objects from around the house, as long as it wasn't dangerous I tried it. You don't want anything that can break or cut you. My favorite toy was a the handle of an ice cream scoop. It felt so awesome, especially when it hit my prostate. An orgasm with something rubbing your prostate is way more powerful than normal. There is nothing like getting the cum fucked out of you.
Once you get used to enjoying some solo anal adventures, bring your partner in on the action. Granted, he's not dating for your asshole (that would make him an asshole!), but I'll bet he would love to use a dildo on you to while you jerk off for him.
Of course, there is always the possibility that you will hate anything anal, everyone is an individual. If that's the case you can stil have a great sex life with just oral sex. Being a skilled cocksucker is great, and what guy doesn't love to get blown?

 

[palemale]

Everyone is different. The first time I bottomed, the top told me to be sure to douche first, so I did. He rimmed the hell out of me and used his finger to get me ready to fuck. It was great, not particularly painful, and I had never used a dildo on myself before. His cock was the first large object up my butt, and it was 9". A good top will know how to get a bottom guy relaxed and ready. I think it's as simple as that.

 

[sweet_taboo]

True. If a guy really knows what he's doing, then he'll be able to fuck you with very little discomfort...and it will eventually feel really great. The only danger might be that it'll feel so good, you'll become adDICKed and want it (him) all the time.

Everyone is different. The first time I bottomed, the top told me to be sure to douche first, so I did. He rimmed the hell out of me and used his finger to get me ready to fuck. It was great, not particularly painful, and I had never used a dildo on myself before. His cock was the first large object up my butt, and it was 9". A good top will know how to get a bottom guy relaxed and ready. I think it's as simple as that.

 

[Kamikaze]

I think that MoaningMike gives great advice. However, just some comments on my end. If you are planning on bottoming, douching or an enema is not always required at all. If you know your diet, you can kinda plan ahead. Just google like bottom diets etc., but generally if you have a lot of good fiber in your diet, and this isn't talked about enough either, your goal in general is to have nice solid poops. After you've had a nice bowel movement is typically when I know that I'm ready for sex, and it's a good habit to check with your fingers just in case. If you do douche, which I don't do often because I had a mishap with I guess using too much water... and you can have an unexpected water(etc) come out after a lot of friction from sex... It may not be pretty depending on your diet. It's a good rule of thumb, if you recently did not have a good experience pooping (not solid or spicy, etc), then I know that bottoming definitely is not happening that day, unless you douche but again this was the one time where I had the mishap because I just didn't eat healthy the day before I guess.. Either way, condoms are a great way not only to keep clean STD wise but if you do have an unexpected small amount of poop come out. lol i think it's funny but I mean shit happens. It's your ass.

Also, always communicate before, during and after sex with your partner. Don't be afraid to speak up. slow is always best at first whether you're topping or bottoming, always start slow.

 

[Kamikaze]

Also while I agree with mike that you wanna be clean before sex you gotta communicate with your partner. I don’t mind a sweaty ass or armpit or junk but some do. As long as you shower at least 3 times a week, but I like the smell of men after a long day of work I usually hate it when I am rimming someone or sucking dick and it literally tastes like body wash. Meh to each his own.

 

[sweet_taboo]

Definitely agree. For years, when I first began getting fucked, I never knew what douching was in terms of sex and neither did any of my buddies. We just made sure we were clean from a shower most times. Natural sweaty man smells were cool, but never funky and dirty. I was fucked hundreds of times and never recall any mishaps -- I guess my diet was on point. I didn't discover douching until I was in college when the guys were different, older, and in some cases more experienced. I wasn't always sure it was really necessary being that I'd never needed to do it before, but I learned to do it if required. I figured sooner or later a mishap was bound to happen and I wanted to avoid that if possible.

Communication is key. I believe that's why I've never allowed random guys to fuck me - I've gotta know you before I let you put your dick inside me.

If you are planning on bottoming, douching or an enema is not always required at all...

Also, always communicate before, during and after sex with your partner. Don't be afraid to speak up. slow is always best at first whether you're topping or bottoming, always start slow.

 

[flamingo]

Great input, guys. Since I'm only 19, I have plenty of time to discover and explore and figure out what is right for me. I want to pleasure my men, but if they don't respect my feelings, they'll get nothing from me. Communication, experience, and respect go a long way to keeping those mishaps to a minimum.