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First time about him, then train him up

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ORIGINAL: Arpig

Introduce him to the joys of touching and tasting, do a lot of that before you get down to the nitty-gritty and do a lot of it in between (at 22 there should be ample opportunity for several encores ).

Ah yes, the joys of younger men.  Schwing! Insta-boner-when-the-wind-
blows-the-right-way. 

And finally...yes use a condom, if he hasn't fucked he won't realise there is any loss of sensation, so get him used to using them (start good habits early, and all that ). And just imagine how wonderful it will be for him a few years down the road when he finally does go bareback....it will be like his first time all over again

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ORIGINAL: GreySaber

I have a few suggestions.    

First, Don't make it a one-time thing. Tell him in advance he gets a certain number, or whatever. It's a learning experience, and he's undoubtedly nervous about performance, etc. Tell him he gets to come back a few times for 'improvement.' It’s his first time, so make sure he doesn’t feel like he has to get it ALL right on the first time, and that you’ll build him to at least a basic experience level. Trust me, this will releive a huge amount of performance anxiety in him.

Second, don't just leap into bed. Go out, have a light meal (not heavy candles or anything, Chinese takeout and a skimpy outfit would be fine.) Play footsie under the table, build anticipation.

Third, be on top the first time. This way he doesn't have to learn mechanics of movement on the first go. 

Fourth, Make him go down on you, and when you do use very clear verbal directions. Explain in advance how going down works on a mechanical level, and think about what sort of movements you like in advance so you have the explainations of techniques planned out. Many people don’t pay attention to what is actually being done when they get good oral, and as a result only know when it’s good rather then how to teach what they like, sinc they don't know what they like, they only know when they like it..

Other little things…   If you are willing, you might want to give him a try at all the basics. Obviously vaginal, but also oral and anal. You could teach him to how to do anal without pain, teaching him to apply lube and whatnot. Some men like the idea of having tried each one at least once, and would leave him feeling well rounded.   On say, the third try, you might try some odd stuff, if he’s willing. Say, the finger in the ass trick. 
I’d recommend against condoms with him, if you feel safe doing that. Condoms have a very, VERY, VERY important place in the world, but they do reduce sensation, and it's his first damn time!

Making the first day be mostly about him trying things, and the second day be all about doing them right. (And tell him that in advance, it’ll make him less nervous.)

Do you think that will help?

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ORIGINAL: merrymasochist

Just to add a small p.s. -

Saturday was scrubbed. We've rescheduled for this coming Friday. Another week to dither and worry.
Drat............

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a very, VERY, VERY important place in the world, but they do reduce sensation, and it's his first damn time!

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ORIGINAL: GreySaber

Don't do the syrup! First, the real taste is the good one. Second, sugar on the vagina can stimulate a yeast infection.

As to his hands, First let him explore, then move his hands to the right places and TALK abotu the right motions. As a man, I can attest that we tend to like direct instructions, and communication with words rather then physical hints. But let the exploring come first.

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ORIGINAL: FelinePersuasion
oral sex has nothing to do with being good with your dick. or a good lover. I've had many plenty good lovers and we never did oral sex.