OK, my friend (we both shall remain nameless for obvious reasons!) and I are both teenage guys, and as such, we both get very horny at times. A lot of the times if we are spending the night at one another's house, we will give eachother oral sex, just to get us off so we can sleep.

One time we tried anal sex, but it didn't work: My penis was too big to even go close to his anus, and when he tried to put his into me he got it about an inch in before I had to have it taken out. It was incredibly painful! We used condoms we bought at 7-11, and lube (moisterizing cream, maybe the wrong lube, or what?). It didn't work.

So neither of us have ever taken the other ones ejaculate in the mouth, we always pull out right before and the one recieving the oral sex will have toilet paper at the ready to cover himself as he ejaculates.

We usually wait until there is some sort of porn on TV before we start blowing eachother, so we pretty much pretend it is a woman doing it. Kind of like masturbating, I guess.

Or, if we aren't at a TV, my friend has a deck of cards (nudey cards, actually!) that we play strip poker (or any other strip game, for that matter) with, and then once we are both naked, we play a round to see who blows who first.

Now, I don't like his body, his face, and all that. But for some reason I like his penis. Secretly I want to take his load in my mouth, but I've never done it. I really wanted to have anal sex with his penis inside me (it hurt a LOT!), and I wish he would take mine in the mouth, too.

I don't have any desire to kiss him or anything like that. I would NEVER be seen holding hands with him in public or anything like that, I am NOT a homosexual that way. But for some reason I still want to have every intercourse I can imagine with him. What is up with that??
I've even masturbating thinking of it sometimes. But I never masturbate thinking of his face or things like that, just his man-parts.

Whats the diagnosis, then?

And if possible: What are household items (or REALLY cheap and REALLY easy to find) lubes that make a fully erect penis fit into an anus better? Is there any way for it to be completely terrible feeling on my part? I want him to do me really fast, but somehow I think that would be really hard to do, anally, am I right? ?????
I've used things like vaseline and moisterizing cream to put small things andd sometimes fingers in my rectum before, it felt alright, but never ever anything penis-sized. I tried one time something that was maybe an inch in width, and could barely put it in! Even with a TON of vaseline! I could barely fit something that small inside, let alone pump it back and forth really fast, how could a penis possibly fit?!?

You are a classic bisexual. Your friend might be too. A bisexual can be sexually attracted to men, but have absolutely no romantic interest in men. They can get off on gay sex, but never ever consider kissing, hand holding or anything else.

The anus does not lubricate. So you need to use a good quality lubricant ALOT. Hand moisturizer is not a lubricant - in fact it is the opposite. It is designed to be absorbed into the skin. Vaseline isn't great either and downright dangerous if you are using a condom as you should. Vaseline eats condoms. The best lube is a silcone lube designed for gay sex. Check out http://www.sesupport.org/toys.html> and look at the Eros lube - it is the best on the market and I use it myself.

I wouldnt Consider You Gay, I consider myself STr8 altho i think im probably Bi, I Love everything on a woman but the thought of touchin a man and another guys penis is a turn off but some Reason I GEt off over Males havin intercourse with Transexuals , i find them attractive cause its the thought of a FEmale and the look just with a penis instead So i wouldnt Say Your Gay unless You Find females totaly un attractive and males better

I think that you guys are either bisexuals or gay. No straight guy would ever have sex with his buddy, whether oral or anal. It also takes time and patience before your ass can stretch enough to take a penis. I masterbate with a very large dildo and it feels great. Be sure you don't rip your sphincter muscles, that is very painful.

what would you suggest to help my anus stretch enough to (comfortably) fit an erect penis?

Masturbate with a sex toy - a butt plug or a vibrator, but only ones that have a flange at the end. The end needs to be bigger as the anus sucks in when you orgasm and it can suck it in it the end of it is not bigger.

You can see two butt plugs I recommend at http://www.sexsupport.org/toys.html

I can handle a dildo that is 9 inches around now.

Clay,

I don't think that this anything to brag about. When you are older and are using an adult diaper you are going to be regretting you have gotten into making your sex toys this big. 5 inches around is considered extra large. You need to seriously reconsider what you are doing.

To quote from a gay friendly website: People who enjoy fisting and large toys are in danger of having bowel control problems in later years. The large diameter of a fist or toy can cause injury to the sphincter muscles, which control bowel movements.

Susan

And the bad news is the average person with probably have SOME degree of difficulty, as time goes on, with those sphincter muscles anyway even without trying any stretching exercises. These muscles tend to go South with advancing age. So, do not make it any worse....my suggestion....try other methods to masturbate that are less harmful.

I guess I should re-consider buying the big red vibrating dildo then. It looks like it would be a lot of fun to use, but I don't want to damage my sphincter muscles and have to wear diapers (that wouldn't be any fun). I find that my sphincter muscles are quite stretchy though. I'll be careful though.