Relevant topic analysis on Penetration:

Penetration and Flatulence
Kind of a random sex related thought.. I've also felt very, well, gassy when I had my annual pap and in the last year or so (since I got my IUD) I...

Dildo penetration before sex?
Sometimes I dont like to use our dildos for foreplay. I like to wait for penetration for my husband. Does anyone else feel like if you use a dildo...

Are flavored lubes safe for penetration?
i know that like flavored condoms arent supposed to be used for penetration. does the same go for lube?

Can you have an orgasm from penetration alone?
I find that I need clitoral stimulation to achieve orgasm. I know I can't be the only lady out there that requires clitoral stimulation to reach...

Can you orgasm from anal?
can a person orgasm from just anal sex or is there double penetration or clitoral stimulation involved as well?

buy him a strap on

There are plenty of possibilities. Several of the strapon "kits" contain a slim dildo for starters. When we started out we got the Acute dildo, which is nice because it's not too big and has a nice bend to it. Perfect for hitting the prostate. You might also consider a small butt plug. Good way to introduce some size and girth without too much length. The Njoy still plugs are good. They make a great small one. Good luck.

You could also start out with a set of plugs and work him up to one of the larger ones before you try a strap-on. It depends on how... for lack of a better word, "stretchy" you think he is. Some people can take large insertions right from the get-go, others need more extended warm-up.

Thanks for the suggestions, he has been checking out some plugs already!

Check out the gold lace glass dildo. Its only about 1" girth or the Get a grip and/or bendable you too by Evolved. They are also small girth and give excellent P spot stimulation, but can also be used for couples play in general (g spot, clit etc). There is also an anal T vibe that is nice and cheap for a first timer with wired remote.

Get a plug or a silicone dildo with a flared base. With the dildo you can start off hand-held and then buy a harness if you decide you want to try strap-on use.

For anal play a smooth surfaced, curved dildo is best. For pegging, one of 1-1/4" or bigger diameter and 5.5" or longer insertable is best.

I believe that if looking from the material point of view as well as the girth and length the Cyber Cock does the job very well on a beginner/intermediate level. It requires a little warm up, is not too hard and hits the spot quite well...

I agree with everyone above. Whatever you decide to choose, go with silicone and a smooth surface. My husband says that the dildos with hard edges are uncomfortable. Start small and work your way up. If you are looking at harnesses I suggest Aslan products such as the Cherry Jaguar. They are more expensive but they are well worth it. Not only are they comfortable but they make you feel sexy and last forever with proper care. Good luck.

A p-spot toy. Maybe something like the aneros. Or a small butt plug

Thanks for all the input. I will be checking out those suggestions!