After the fourth or fifth time, today, with no lube…probably.

After the fourth or fifth time, today, with no lube…probably.

I Would Have Been A Willing Pupil If My Mother-In-Law Had Looked Like That.

So That&Amp;Rsquo;S The Plan.

Chastebob

And You Thought These Stories Were For Kids.

Ain&Amp;Rsquo;T It Always Like That? We Tend To Blow It When We Were On The Verge Of Getting The Best Of Both. She Must Have Read Woman&Amp;Rsquo;S Guide To Chastity Security.

There Is Something Delightfully Cruel About Using Male Ego And Shame To Make Him Try To Withstand Punishment Without Reaction, Knowing All Along That In The End It Will Be Futile.

Lucky.

I Do Love This Turnabout Idea. I Captioned These Months Apart, Wasn&Amp;Rsquo;T Really Aware I Was Almost Repeating Myself.

Chastebob

Anonymous Submitted This

Back To That Be Careful What You Wish For&Amp;Hellip;Or At Least How Much Detail You (Forgot) To Include. As Always, Chastity Device Added In Photoshop

Isn&Amp;Rsquo;T It Always The Case, The Biggest Changes In Life Just Seem To Hit Us From No Where, Completely By Surprise. But When We Look Back, There Were Little Hints It Was Coming, But We Missed Them All.

tights tightsqueeze