(copied from Fetlife)
NOTE 1
Have you tried one of these? http://www.amazon.com/SURGIMED-3-Prong-Anal-Speculu…
They can be really fun and hot if used with a sense of adventure, and they'll help open you up. Especially if there's a nurse costume involved!
I have one for myself because I have a nervous rear. It's pretty normal. I learned to stop fighting it and enjoy the process of opening up without being disappointed. It turns into a game.
Do you two ever do prostate play? That might help as well. Re-condition your body that your ass is a pleasure center, not something to be afraid of. I have this, which is amazing:http://www.amazon.com/PURE-Njoy-Metal-Polished-Stee…
Hope you find your butt happy place soon. It's a bummer when part of your body gets nervous, but it's fun bringing it back.
NOTE 2
Pegging is really, really special to me, and I'm grateful when my partners are open to and excited about it. One of the hottest things on the planet when a guy says he's into pegging. It shows a real sense of ease and sexual awareness - orgasmic dynamite!
The speculum is a great, affordable tool. As in all things anal, my recommendation is to go slow, use lots of lube, talk through stretches, and enjoy. Don't make it work -- this is play. If it becomes work, take a break, bake some cookies, and come back to it. With the speculum, you should start closed and stretch very gradually -- opening it a little, waiting until you're settled in and completely relaxed, opening a little more, settling in again... Take your time. It helps to think of the rectum as a particularly strong muscle that needs to be coaxed -- just like stretching quads after not running for a while, it takes patience and a sense of ease and "We'll get there when we get there." You can't rush a butt.
I go up and down with anal sex performed on me. Sometimes it is easy breezy and other times I need half and hour of stimulation and stretching before I'm ready. I love it, but I have a fussy rear. For me, genital stimulation while stretching is a sure fire way to make things easier -- I often stimulate myself while my partner works on the back end and talks dirty to me. Every little bit helps! My ass is more telling of my emotional state than any other part of my body -- when I'm stressed or upset it's a no go. I have to be in a playful, sexy state of mind to really enjoy anal bottoming.
Here is a nice little primer to prostate play: http://goaskalice.columbia.edu/male-hot-spot-massag…
Here's my nutshell version of "How To Make Friends With A Prostate":
Pee first and evacuate your bowels if you can to make things more comfortable (excuse me if this is too graphic -- I'm a details girl). The prostate is about 3/4" to 1.5" inside a man's rear. When you're laying on your back, she can (slowly) insert a (well lubed) finger palm up and reach up toward your pelvic bone. She should feel a lump, anywhere from the size of a macadamia nut to the size of a walnut. Most are shelled pecan size. :) That's your prostate!
She can massage with a back and forth motion and then begin to massage by bending a finger up further toward your pelvis, bending her finger back toward her palm in a "come here" motion. It does not need to be rigorous -- people have varying degrees of prostate sensitivity. You may not feel much at first, but if she continues to massage it you should begin to get stimulated and may feel a little bit like you have to pee (a lot of women have the same sensation when their g-spot is directly stimulated). That's one way to know you're doing it right. You don't actually need to pee, so don't worry.
She can keep going with one finger or slowly insert more -- whatever the two of you are comfortable with. If she's right handed, I would recommend her using her left hand for the prostate so her right hand is free to play with the rest of you. Unless she's ambidextrous, in which case you are both lucky. A lot of partners enjoy the stimulation of a little bit of "in and out" motion along withe the prostate massage -- you may find your rectum gets happily sensitive as the play goes on. You may also find that you want more stimulation as the play goes on -- just listen to your body and tell her what's going on, and all will be well.
I've been able to make partners come just from prostate "milking" (which is what this play is called). It's a weird orgasm, because they don't necessarily get more than half hard. Still, reports are that it's very intense. In my experience, coming from prostate play alone is not necessarily the norm -- it's more about the extra sensation. It's fun to try, but don't get overly focused on coming from prostate play by itself, especially not at first. You will get more attuned to the sensations and become more sensitive to them over time, and you'll be able to communicate what you want and how you want it.
You can also get strap-ons that are meant to stimulate the prostate (after a thorough washing, most of them can also be used for g-spot play). I have this one: http://www.amazon.com/Tantus-P-Spot-Dildo-Black-Toy…
Don't worry about a harness -- that is a fancy dog and pony show that can come later. Holding it in her hand gives her more control, and using a harness takes some practice. I like the Tantus company a lot -- some of the most high quality, durable silicone on the market. I have a few of their toys, and they're my favorite for insertion along with glass and metal. The trick with this one is keeping the curved part pointed upwards toward the prostate -- I cut a little notch in the "up" side of the flange so I always know where the curve is.
More than anything, the fact that you two are committed to seeing each other sexually happy and healthy is the most important thing -- everything else is just about learning new tips as you go along. Whatever you do, be patient with your body and listen to it. I'm really happy you two are walking the road together.
NOTE 3
Again, for me, it is really sexy when a man is into pegging. It tells me he's sexually open, and also that he's taken the time to learn what he likes. It is a HUGE turn on for me when partners tell me what they want -- it is my most common sexual request. "Tell me what you don't want me to know you want..." drool
Some people are turned off by butts in general, so there's that. I just happen to not be one of them. I remember I was with a boyfriend who had never been rimmed. We made a whole evening out of it. You would've thought I'd bought the guy a Porsche, he was so delighted. There's a taboo around straight boy butts, which makes it difficult for some people. I, however, am all about it. I think the taboo itself is part of the fun!
More than anything, be aware of your emotional state with your rear. I'm serious that the rectum is like a portal to the emotions. I think that's one of the reasons it's so satisfying when things go well. Be patient, gentle with yourself, and congratulatory of your partner -- she cares about you, so she might be nervous about screwing up. You can both reassure each other and build one another up -- always a good way to connect.
If you have fun with one finger the first go 'round, call it a success and be done. The next time, maybe two fingers or a small-medium butt plug. Save the strap on and speculum for down the road. She needs to re-establish a positive, happy relationship with your rear. It'll take time. Don't rush it. If you got food poisoning from a peach, it would take you a while to eat peach pie again. One nibble, see how it goes down, another nibble, and so on. If you build slowly you're much more likely to enjoy yourself without getting the jitters.
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