Strict But Classy

Sexy Assertive Ladies

[robert-otk]

Sure, I can be strict

[emwe5775]

[assertivemilfs]

You have a lot of experience with my hairbrush and paddle, but in this setting that heavy ruler on my credenza seems particularly appropriate. Maybe, a hundred strokes on your bare rump would be a good starting point?

[emwe5775]

[assertivemilfs]

Yes, I may be old, but you are the one that is busted! Drop your jeans and jockeys and fetch the hairbrush.

[sexy-older-women]

[assertivemilfs]

I know it isn’t maintenance day and you have been nothing but well behaved, but we are still going upstairs for a spanking.

Why? Because it excites me and my guess is it excites the hell out of you too!

No this isn’t going to just be a playful couple of swats over your slacks, it is going to be just like a full-on punishment spanking. You will be over my lap, bare below the waist, count every stroke, I will use the hairbrush, paddle, and maybe the strap, and there will likely be extras for any wiggling, failure to count, or the slightest breach of decorum. When we are done you will undoubtedly be marked and sore, but we will also have some of the best sex you can remember!

While I know you are worried, the flush in your face and the bulge in your khakis betrays the extent of your arousal.

[emwe5775]

[assertivemilfs]

Yes, right here on the couch. Drop the jeans and briefs and fetch the ping pong paddle from the rec room. I think a hundred is about right, at least for starters. Do I need to send you upstairs for the hairbrush, too?

[sexy-older-women]

[queen-di-mari]

[stilettoheeladmirer]

[thegentlemantcollectsmore]

[assertivemilfs]

I thought I would text you a quick pic of what I will be wearing tonight. Meet me in our bedroom EXACTLY at six cell phone time. Don’t be late as the timer starts on the hour!

I have a challenge for you. If you can make me cum in two minutes, or less, I will let you enjoy taking me from behind like you always ask me to do. If you take under three minutes, I will give you a blow job and even swallow. If it is five minutes, or less, we can make love in the position of your choice. Under ten minutes and I will give you a hand job, but you will lick up and swallow every drop afterwards. If it takes more than ten minutes, you will have a vigorous spanking with the ping pong paddle equal to the time it takes beyond ten minutes before you get your hand job. If it takes over fifteen, the hairbrush will replace the ping pong paddle, and you will get an orgasm from a hand job, but it will be BEFORE your lengthy appointment with the hairbrush. God help you if you have not completed your task in twenty minutes because you will get the hand job, a harsh ten-minute hair brushing, and we will repeat the process tomorrow night.

[emwe5775]

[mk1fed]

[assertivemilfs]

I always thought the punishment should fit the crime! For unauthorized masturbation I want you to strip from the waist down and put your hard little friend between my nylon covered thighs. You are then going to pump away between my thighs while I spank you briskly with my hand. You will keep that up until you spurt all over my legs and shoes. At that point, you will lick everything clean and your real punishment will begin with a hundred hard post-orgasm strokes with my heaviest hairbrush. I doubt you will be pleasuring yourself without my permission again any time soon!

[beautiful-when-she-s-angry-too]

Loving Wives #25-33-2

[beautiful-when-she-s-angry-too]

Assistants and Audience #25-11-1

[beautiful-when-she-s-angry-too]

Scantily-Clad and Sexy Spankers #24-12-2

[assertivemilfs]

I was thinking about a nice sexy spanking for you before we make love tonight just to get you appropriately focused to please me. I will just use my hand and let you rub your little friend between my stockinged thighs as I turn your bare cheeks to just the right shade of red. If you are then able to satisfy me during our lovemaking, that will be all. If not, I will have you fetch the hairbrush and will then give you a blistering disciplinary spanking to remind you to do better next time. Ready?

[leggyangels]

[assertivemilfs]

You remember that the first and third Mondays of each month are your maintenance spanking night? Since you have made so much progress, I have reduced the frequency of your reminders from weekly to just twice a month. However, I have upped the intensity a bit. You will get three timed spankings of equal duration with the ruler, ping pong paddle, and the hairbrush. If you are really good, each spanking will only be three minutes. If you are anything less, each will be four minutes. If you are backsliding at all, each will be five. If that does not work, we will return to the weekly sessions but keep the three, five-minute cycles until I am convinced you are back on track.

You really think that I am being too harsh? I was planning on this being a three-minute day, but since you are arguing it will be four! Do you want to try for five? No? Then drop you slacks and boxers and get across my lap!

[rebeltels]

[assertivemilfs]

Just making sure that I appropriately address all of the issues from the past week. Please stay with your pants and briefs at your ankles and your nose in the corner while I double check before we get going with your spanking.