If he's experiencing pain you guys are taking things too fast. He needs a proper warm up which includes getting him aroused, relaxed, oral (totally optional haha, but my husband loves it), fingering, and a lot of lube before even touching the toy since he's a beginner. Work your way up to it; don't scare him off before he can even experience anal pleasure.

Are you doing some warm up with fingers first and using plenty of good thick lube? The size 'should' be small enough so I think you may be all right there, although th bulge could be a bit much with out some warm up.

Where is he feeling the pain? Is it at the anus or is it poking him inside? If the anus, go slower and do some warm up with fingers or something smaller. There is a good curve on the Naughty Boy and that may be the case if it's pokey. If so, try something with less of a curve. Something like your Sphere may work good.

Lastly, he needs to be able to relax and clinch up. That may be one of the biggest keys to pain free butt play. Start with some other stimulation, like some oral, and ease into the butt play.

Hope that helps a bit.

The Naughty boy was my first toy and look at all the toys I have tried. it is a good beginner toy, not too big and frankly, it hits the sport well.

A few suggestions.....

1. He needs to mentally want to use it, if not he wont enjoy it regardless adn eh wont be relaxed.
2. He should be relaxed!!
3. warm him up, if he feel sits too big, use a finger first, then when hes relaxed use 2... but remember always use lube... preferably something thick
4. Don't go too fast, go at his pace, he should enjoy it if its on his terms and he says ok i want it now...
5. use lube, lots of it, always.. I suggest the "anal Lube" which can be found on here.. its water based and thick. A great lube!
6. listen to him. If he is giving pushback or isn't liking it, take it a step backwards until he is relaxed and enjoying it. Go slow and eventually he will be in total bliss.

he may not like the Naughty boy to go in all the way because it might put too much pressure, but if it isnt a problem get it in all the way because thats how it was designed. it wasnt made to be thrusted, but rather to kind of rock on it for a slow in and out feeling.

Enjoy!

If you say he's "never allowed anything near his rear," you've got a little bit of work to do before you bring in toys. Let him have a few orgasms with his anal tissues engaged so that he warms up to the idea mentally and physically. If he's very averse, start off by

~giving him a few blow jobs and pressing your finger to his anus- don't try to work it in, just let your finger apply pressure to the outside. After he's had a few orgasms this way,

~make sure your nails are well-trimmed, add some lube or saliva to your finger, and work your finger inside his anus. Make sure to keep him well-relaxed with blow jobs, and always listen to his feedback. If it hurts, stop moving and let him guide you out. If it doesn't hurt, see if you can find his prostate. Explore plenty, hopefully it's pleasurable for both of you.

~If he's open to it, warm up his anus with your tongue. In my experience, guys who are squeamish about receiving anal stimulation are more likely to let you use a finger than your tongue.

~After he really enjoys anal play in these forms, and he's had a good many orgasms to solidly establish in his brain that prostrates are fun, let him insert your Naughty Boy himself a few times. Once he feels comfortable,

~then it's your turn.



Always, always listen to his cues and don't let anything hurt him. Taking it too fast can result in a lot of pain.

#2 thing - prostate play (not just anal play) can be odd and unusual at first, so you'll have to get him "into" it as well. One big thing to keep in mind is that the prostate becomes more sensitive and is more likely to give "pleasure responses" to stimulation when the guy is sexually excited. It's also easier to find the prostate then. Once you've done the "anal intro" then work in the prostate play.

Fingers are a good start, as you can feel for the prostate and figure out where it is. Once you've done that you can work out how best you use your Naughty Boy.