I'm seriously NOT bragging, but my new boyfriend has the largest penis I've ever seen (both long and very, very thick). While that may sound like every girl's dream, I'm particularly small, and we're actually having trouble "fitting." We've had instances where he can't even enter me, and when he does it's almost uncomfortably tight. Mix that with a condom that's too tight (Lifestyles Large...I'm looking for Durex XXL now), and you've got sex that's fun and playful, but not satisfying. Any suggestions on getting me to "loosen up"?
The big dick beloved by XXX video directors can actually be problematic for the proud owner of such a prodigious prick. The circulatory demands of a big cock are pretty intense, making it difficult to get fully erect. I've known a couple of guys packing heavy equipment who actually get dizzy when they're hard. Then there's the problem that you and your boyfriend are facing—getting the darn thing into a normal-sized mouth, cunt, or ass. The man with the biggest cock I ever saw (in person, at least) once said to me, rather bitterly, "I feel like all I ever get is hand jobs. All this admiration is nice, but what I really want is a decent blowjob."
I have a few helpful suggestions for you and your beloved. The fact that you want him is your biggest ally. Vaginas are made out of a lovely stretchy self-lubricating material and they have been known to accommodate the human hand as well as a baby's head. But they've also been known to get bruised and sore, or even torn, and we don't want THAT at all!!
Even if you get very wet for sex, having a decent lubricant with a slightly thick texture might be a big help. The lubricant inside of your vagina might have trouble finding its way to the shaft of his dick when you are tightly plugged and he is partially outside of you. So from time to time, he can help out with a little squeeze from the lube bottle. The padding of a good lubricant can also prevent abrasion.
Don't be in a hurry to engage in intercourse. Some men (and women) think that the first appearance of wetness is the signal to start fucking. (Well, we also want to do it right now because a state of horniness makes this an urgent matter.) There's actually more room inside a woman if you continue to pet, stroke, or lick her until her sexual response cycle gets a bit further along. The uterus actually lifts and moves slightly back as a woman is stimulated. This creates an extra pocket of room in the upper third of the vagina, making deeper penetration possible. The opening also becomes more relaxed and less sensitive to pain.
How do the two of you feel about dildos? I think it would be a good idea to have a few, let's say three, of graduated sizes. The smallest one should be a dildo that you can accommodate even during the early, light phase of arousal. The largest should be close to your boyfriend's size. I suggest using these while you masturbate. You can teach your vagina to dilate as long as you open her up slowly and gradually, with positive sexual rewards along the way. Don't ignore your clitoris. Getting her all tingly and urgent and hot will also help you to expand.
This stretching process will take a while. Keep doing your Kegels in the meanwhile. You want to make the muscles that support your vaginal walls more supple and strong, to keep the whole area toned. This should increase the strength of your orgasms and set any anxiety you have about being too wide open to rest.
The graduated set of dildos can also be used during sex play. Some guys don't like them, but others are perverse enough to enjoy teasing their girlfriends with a toy, making her really hungry for dick, and at the same time helping her to relax and be ready for Superman. If he doesn't want to use the dildos, he can use his fingers and hand to gradually help your vaginal opening to acquiesce.
Since all of this feels pretty darn good, it's a wonderful way to extend the pleasure of intercourse.
By the way, I do not encourage a similar process if you're having trouble accommodating him orally. The muscle that opens and closes the jaw is very small and delicate. It is easy to give yourself a painful inflammation called TMJ that can result in severe headaches and other problems. The jaw muscle should not be stretched excessively by gags, dildos, penises, etc. (If you can think of an "etc.," please do write in and share with the rest of the class.)