A Cut Above the Rest
I'm a nineteen year old gay guy. I'm heading to university this fall and have found a great guy who's also going. We live several provinces apart and we're going to be dating once we're in the same city. I've had two boyfriends in the past but I'll be his first. We're also both virgins. He told me that he has an uncircumcised penis and I'm wondering how do I go about with oral and anal sex with him? Are there any differences or things that make sex harder or easier with an uncut dick? Or do I just go about with it as I have done with cut ones in the past?
Also, I have an above average sized dick, I have concern about hurting him the first time but he doesn't seem to be worried. He said "We'll just use more lube," Is that all I need to do, besides taking it slow?
Hmmmm. Why do you say you are a virgin if you have experience handling other men's erections? I am guessing you might mean that you haven't been penetrated. If that guess is correct, I'd recommend that you start playing with your own butt as part of your masturbation. Put on a glove, squeeze some lube onto your fingers, and see how it feels to touch the outside of the orifice. Make sure you have completely explored how simple pressure and stroking feels before going inside. Working on opening yourself up, relaxing to accept a finger or a toy, is good training for being able to open your boyfriend that extra bit so he can enjoy your very nice gentleman's equipment.
If he has never been fucked, it would be a good idea for him to start exploring as well. I think it's important for partners to agree that they won't do anything to hurt the asshole. This useful part of the body already carries a lot of tension and shame. It shouldn't be punished by bad sex. Some of us believe that we have to get fucked really quickly, or we will bore our partners. But the truth is that exploration outside is just as much fun as sliding in and out. The point is to feel good, not to produce any specific behavior.
I am a big fan of the concept of anal training. Having a series of butt plugs in different sizes is essential. Put a butt plug in and let him go about his daily activities in the nude. If it falls out while he is doing the dishes, he needs to be taken into the bedroom and have a slightly larger one put in. If there is some ancillary fooling around, that's all good. Our nonsexual reflexes tell us that if there is pressure in the bowel, we need to push down to expel waste. The long-term butt plug teaches him to tolerate that feeling, eroticize it, and relax just enough to provide some resistance for the plug (or your dick). I'm not sure if you are a top, bottom, or switch. But if you want him to fuck you, try switching so that one day is his turn to play hide the butt plug, and next day it is yours.
To avoid exposure to the questionable microbes that party in the bowel, make sure you disinfect your butt plugs with a 10% solution of bleach and water, or use a disinfectant recommended by the manufacturer. There's a good article about cleaning toys at http://brown.edu/Student_Services/Health_Services/Health_Education/sexual_health/sexuality/sex_toys.php. Use a condom on the toy to keep miniscule villains out of its pores and nooks and crannies. (To a germ, virtually any surface that seems flat or smooth to us looks like an English muffin.) Some people are so concerned about not being exposed to a partner's internal biology, they have their own set of sex toys. But buying two of everything can get pretty expensive, and it's hard to be meticulous about keeping them separate in toy storage. When things get hot and heavy, there are more important things to do than remember whose dildo is under the pillow and whose is where the moon would love to shine.
Extra lube is helpful, but mutual trust and taking it slow and easy are also important. I like to keep an assortment of ass toys on hand to start the process of anal discovery if a partner is a novice. Use smaller toys first, then increase the size until you think your cock might be a good fit too.
Regarding foreskin, it's usually just a lot of extra lovely sensitive skin to play with. I don't think it will interfere with oral sex. But it might make it more difficult for him to keep a condom in place. Some guys with foreskins will buy an extra large condom, then pull it back over their balls, to anchor it When it comes to wearing a condom, with your extra-big cock, you may need that extra latex just to cover your dick. Experiment with some condoms while you are jerking off to make sure you won't break them by putting too much stress on them. Basically, you want to put the condom through hell so you can tell what it takes to make it rip. When you are fucking him, you may have to resort to holding the condom with one hand while you hang on to him with the other or give him a loud but nice little slap on the ass.
As long as he washes under his foreskin so that his equipment doesn't smell like expensive cheese, you will probably enjoy the difference between his cock and your own, and find a lot of different ways to tease him by manipulating the extra skin. Uncut cocks are as yummy as the tidy ones that have been trimmed, so consider it his dowry.