Deep breath. And... relax. Here goes

Just paddle him until your butterflies are worked out.

 

You continue to amaze us with your journey, @longtallsally. What's really special to me is how thoughtful and engaged you are. Kudos!

Pegging: I enjoy this a *lot*. Seems that most men who don't have a negative psychological hang up about it do enjoy it, if there's proper care taken (the prostate is wonderfully sensitive). For me, two critical things: lots of lube, and slow, patient entry at first. Getting the first sphincter to relax is the trick. If it isn't and entry is fast, it burns like hell and very unpleasantly. But, with very slow initial penetration, it relaxes, and after that, there's no need to hold back. It's surprising, I think,until you've both had some experience: seriously painful if you're not very slow (even stopping and resting a bit) on first entry, but then completely accommodating and pleasurable with even aggressive pounding once in (if there's plenty of lube). Of course, everyone is different, but my wife doesn't have to worry or be the least bit nervous about hurting me after she has entered fully once -- she can have as much abandoned fun as she wants.

I also think you probably don't have to worry about length hurting him unless you go wacko long (say, 10" or longer). The first, vertical segment is quite long and capacious (and not a lot of nerve endings past the sphincter and prostate) -- the pain risk is just at the entrance (and with certain toys or fingers banging the prostate too roughly, but generally a dildo won't do that because it's sliding past, not poking the prostate).

 

You could always use your hand to work it in at first so you have better control and feel for it it that would make you feel better. Then use the harness when you are ready

 

Go loving, slow and sensual remembering he is a virgin, and that you are "taking his virginity". He might experience a little pain, pause, wait for him to relax pushing a little deeper as he relaxes. It will hopefully be transcendent for him. Wear white. Maybe make him wear white too.

 

@longtallsally Hope you’re feeling better. It’s great to hear Pete took his assignment seriously. Are you planning to have him caged when you peg him?

 

I think that I would keep him caged

 

You don’t want something to get in the wrong hands

 

@longtallsally I assume you’ll keep him caged until Friday. That will give him some time to “practice” with a butt plug and/or the toy he selected while caged. At that point you can decide which way you want to try it. You also might ask Laura for her suggestion.

 

Uncaged might send the wrong message

 

I don’t think there is a right or wrong answer on whether he should be caged or not.

Personally I enjoy being pegged while caged as there’s no distraction from what I’m feeling in other areas. I do feel more submissive this way. Only recently did I learn I could orgasm through this alone. Initially I would think pete would find it really frustrating as he’ll really need to play in the front to get the desired response… so it would be more domineering if you kept him locked up.

However, as this is a new experience you also want to be able to gather an opinion to how he really feels about it. So if you removed the cage the size of his erect penis would show his true colours. You could throw in a few “oh looks like someone’s excited” etc as a little form of embarrassment.
It may be that he isn’t erect at all and the whole situation makes him more nervous, in that case you’d be able to adapt your approach accordingly.

Maybe it won’t be so bad to let him fully enjoy it and want to come back for more, in which case you can then disappoint him by keeping him caged next time.

 

@longtallsally You could always let your Pete make the choice. After all he did the research, obtained the toy, and even gave you reading material on the topic. If he chooses to be uncaged, you could have him leave the base ring on (it’ll make it easier to relock him afterward but he’ll be able to enjoy the dual sensations of being pegged and played with). If he chooses to be caged he’ll be better able to focus on the new sensations he’ll experience and if the stars align perfectly, may reach the elusive anal orgasm.

Either way can be fun. He’ll also require a lot of cuddling afterwards because it’s a new experience that redefines your roles.

 

Good points. Well made. Think I've changed my mind from what I said before.

 

Cage him but let him use vibrator on cage while you peg him.

 

Sounds like you're well past the "it's just our kink" phase and well into "it's now our lifestyle".

 

you can also apply a condom on him with numbing spray/gel underneath. That way, he can stroke himself silly but not orgasm from it. If he complains, tell him that you want him to be focused on the stimulation of everything except his penis. An angle toward the inside of the pubic bone will be the most pleasurable as it stimulates the prostate gland so figure out the proper rhythm and angle and stay focused on that.

You are going to find out that all that thrusting is more work than you imagine so make sure that you are ready to break a sweat! Adding some stimulation, like a bullet vibe, for yourself is a good motivator to keep going is always a good thing. You can add intensity by being vocal and letting him know how much it turns you on so plan ahead and think of the things you want to say that will maximize the experience!

And HAVE FUN!

 

Since you both enjoy nipple play, try some of the nipple cups for inverted nipples. It uses a light vacuum to temporarily enlarge the nipple and also makes them far more sensitive. Amazon.com : Nipple Corrector for Inverted, Flat and Shy Nipple, Can be Used for Breastfeeding or Women, Softly Wear Day and Night(1 Pair with Travel Case) : Health & Household

 

Here is another product I found mentioned on another thread on this site that I'm finding very effective.

 

As usual, @Jessica Alexander offers some lovely suggestions and observations.

I really like the idea of using numbing cream and condom for this. My wife has me "suit up" like this for PIV much of the time -- she wants the penetration but doesn't want me coming. It is ... exquisitely frustrating. But she's never had me jerk it like this when she's pegging me (or otherwise) ... I'm going to try to find a way to gently suggest that!

And Jessica has a good point about the thrusting: depending on what exercising you do, or whether you happen to be an active cowgirl rider, you are likely to find that thrusting uses muscles and stamina that aren't well developed. When my wife started pegging me, she was quite surprised to find out how how I'd been working all these years when I was doing all the thrusting. (I say "working hard", but of course, once the muscles are developed no big deal, and I certainly don't think of it as work!)

 

@longtallsally Real life always comes first and it sounds like you’ve been making the best of it by using the additional time to practice wielding the device. Edging to the point of making you both TFD should make it totally erotic when it happens - especially if you use it to show him what it’s like to give head prior to taking him.

Stainless steel adds weight and is a constant reminder of being caged for you. Plus it looks and feels sexier.

 

Irrespective of any posts to the contrary, I will operate under the assumption you were talking dirty to the pile of pillows the whole time.

 

Those little cups are a game changer! Keep using them to keep his nipples sensitive. Then you can tease & edge him easily without ever removing his cage. He will get TFD in the moment, but he'll be able to go longer between rewards / releases. Eventually he'll start to crave nipple play. And it's so much fun for you. My wife gets very aroused just from teasing me.

 

The advantage of adopting a chastity lifestyle is that it opens you to so many other avenues of erotic play. It allows both partners to enjoy the journey without simply rushing into the end game. Being TFD (as @longtallsally said) and unable to do anything about it really helps to explore the overlooked opportunities for closeness and pleasure.