Dangerousangleofadream - Femdom

You weren’t going to tell Mother about her behaviour were you? Especially as she had proof of your shameful boot fetish.

“I want a boy who sits at my feet and rests his head in my lap while I run my fingers through his hair. I want a boy who knows he doesn’t have to be in charge. He doesn’t have to be in control, even of himself. He doesn’t have to worry about a thing. He can just watch me ride him until his mind goes blissfully blank. I want to be gentle, so gentle with him. I want a boy who wants to be good for me. I want a boy who asks if he can please me. I want a boy who likes to be on his knees. I want a boy who lets me take away all his stress, all his tension, all his pressure. Shh, baby, I’ve got you. I want a boy who feels safe with me. I want a boy who falls apart for me, a boy who comes undone. I want to tell him how beautiful he looks like that. How perfect, how sweet, how good he is for me. I want a boy who gets flustered, a boy who blushes, a boy who squirms under my hands. I want a boy who moans so easily he embarrasses himself, and I want to say Shhh, baby, you look so good like this, so pretty. I want a boy who arches helplessly when I praise him. I want a boy who listens to me whisper sweet nothings in his ear with my hand wrapped around his cock. I want a boy who turns to me for comfort, and I want to be the one to comfort him, always. I want a boy who lets me take care of him.”

— /u/evoket/, Reddit user

TL;DR

pegging is so important in a long-term chastity relationship. 1, it is a regular reminder of who has the cock in this relationship; 2, it remind him you're in charge; 3, it keeps the male ego away. it's hard for him to be stubborn and argumentative when he has a recent memory of you pegging him; 4, it simultaneously teases and denies him while providing a sexual release. remember this IS his sex now PERIOD.

always remember to put a vibrating toy in for yourself to have so fun ;)

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pegging does all the things that you need to do in order to successfully pull off a chastity relationship and let's be honest... it's a little bit of pay back for all the things he used to do to you. did he use to dress you up in degrading outfits? smack your ass until it was red? pull your hair? tie you up? call you a slut or a whore? fuck you until you couldn't walk straight? whatever it was... now it is his turn. furthermore...

it enforces that you're in charge. the one with the cock is in charge and YOU have the cock in this relationship.

it gives him a sexual release without the sexual satisfaction of penetration and having a "full" orgasm.

it keeps him horny and willing to please.

it is both a punishment and a reward.

it is a form of teasing as well as a source of teasing (more on this later)

this is his sex now, so be generous with it.

in your day-to-day life he will find it hard to be argumentative and have that male ego when you had him bent over moaning into a pillow last night. tell him how cute it is that he tries to be tough and masculine considering he was moaning like a bitch last night.

teasing ideas:

have him suck your strap-on. put in a vibrating toy in yourself and do this until you cum.

take a picture or a video of you pegging him and text it to him. tell him, "this is what is waiting for you when you get home."

use some light bondage to restrain him to the bed face down with a pillow under his hips. put ear plugs in and a blind fold on him. leave him there for however long you want. go take a bath and drink a glass of wine. put a butt plug in him and have a remote controlled vibrating cock ring on his cage that you turn on occasionally. once you're ready for some fun, mount up, turn that vibrator on full blast, and give him a the ride of his life.

while pegging him don't forget to smack his ass. leave it red. remember when he used to smack your ass? it's pay back. take a picture/video.

after you're done pegging him, detach the dildo and leave it in him. make him carry it around the rest of the day or sleep with it still in.

if/when he cums from the stimulation of you pegging him (+/- the vibrating cock ring) that doesn't mean you're done. continue to peg him. use his cum as lubrication on your strap-on or make him eat it.

peg him in fun places. the garage, the shed, the car, the backyard, camping, changing room, at work, anywhere!

dress him up in some of your lingerie or a fun outfit (maid, nurse, cheerleader, etc.). you dressed up for him… it’s only fair he dresses up for you now. take pictures and send them to him later or show him them at a later date to embarrass him.

What's a good chastity period for a beginner?

I would say start off with a week long lock, just to make sure that the chastity cage is a good fit, and that it doesn't rub or cut in anywhere.