Cruel Daddy Weekend - part five
Sandi aka Mistress Dragonfly stood up and stretched and then went to retrieve her “Mommy” looking robe. Her face softened as she put it on thinking of the caring ritual she and Gerry had developed. After they had all become comfortable as an intimate foursome, (something that DOESN’T happen over night or even successfully very much) Gerry had confided in her that the “Mommy/naughty boy” spankings they did, made him crave the humiliating and painful training session in Mistress/slave mode and he wondered if there was a way to combine them together with the naughty boy bottom blistering happening first.
I thought about it and realized that the hairbrush spanking probably raised his endorphins to a level that made pain pleasure, I have experienced this myself, and that euphoric feeling did often indeeed demand “More and Harder”. He felt that it would make a session more pleasurable sooner as he would already be raised to that level quickly from the harsh disciplinary spanking. This would mean that warming up took less time, and he would reach the higher pain heights he sought, like I, sooner. We talked and agreed that the harsher punishment raised the anticipation and fear level higher and that it made perfect sense to start with it if that was what he wished. I had found that putting him in submissive mode before the “Mommy spanking” also forced him to focus on the slave thing, and then having to switch when he first arrived into a naughty boy churned things up and heightened his arousal so that the hairbrush cracking against his skin wasn’t quite so physically harsh, because after all this wasn’t a punishment (Mommy spankings are strictly punishments for breaking the rules established by both Mary Kate and Gerry) but fun we both enjoyed.
Once in the robe, Sandi realized how silly her shoes looked and decided to change them to comfortable ones till after she had dragged that naughty Gerry inside for his hairbrushing. Ian and Sandi lived in the country on vast acreage surrounded by very few neighbors and an outside bare bottom was NOT a risk. Once in slippers she picked up her wicked hairbrush, it was oval made out of a reddish type wood, the business part of the wood was about a 1/2 inch thich, overall it was about 10 inches long and the oval business end took up just over half that length making the smack part about 6? by 4?. It had ivordy rubbery tines for brushing hair, and was also interesting for sensation play if the brush side was used for a light spanking. She had a wicked black plastic rectangular one about the same size that worked bettter on Mary Kates bouncy cheeks but this one was Gerry’s favorite. Ready she turned and made her way to the front door.
Gerry drove down the road towards his Mistress’s house, his face flaming from the sensations he was feeling. His cock throbbed, protesting at the ring, his ass clenched and unclenched still tender from the plug fucking he was made to give it. He was embarassed and had taken the chance of someone see him with woman’s panties on and his barecheeks on display fucking himself. His bare bottom felt the warmth of soft leather beneath them. His head whirled with what he had just done and what was to come. Oh man he was gonna have so much fun, once he got past the dreaded hairbrushing. He squirmed thinking of the ten minutes he had earned with the electrical plug. It was a modified butt plug with contact points on it worked liked a cattle prod once turned on, but intensity and speed could be adjusted, it also had a pulse mode that gave variable shocks overall with a random harsh strong pulse. It was controlled by remote control but could be set, turned on and left as well.
Gerry both hated and adored it. He loved the electrical play and it aroused him immensely it made one feel so helpless and weak and at anothers mercy. It made him sob and shriek and beg but it also gave him the best and longest orgasms when he was finally allowed to cum. But while it was happening he wanted nothing more than to have it end. As he drove into Mistress’s long driveway he remembered his orders and squirmed his bottom down into the seat, sending the plug deeper and shock waves thorughout his body. Shaking his head he moaned as he saw her standing on the front porch, arms crossed in her robe and slippers, THE hairbrush in hand. “Please Mommy” came out of his mouth even though she couldn’t hear and he squirmed his bottom even more imagining how much it was gonna hurt! Pulling into his spot he gripped the wheel and watched wide eyed as she marched down the stairs that grim I am going blister your bottom look on her face! Watching her stunned it wasn’t till she reached his door that he remembered the script and he quickly reached down and began to work his jeans up frantically over his hips. Sandi flung open the door to reach in and grab him and stopped a pretended horrified expression on her face.
“Were you playing with yourself young man?” she said her voice angry and sharp. “As well as skipping school? WELL well you have certainly sealed your bare bottom’s fate this day, naughty boy!”
"Nnnnnoooo Mommy” he whined ,his mind delighting in this.
“Now you have added a lie to your tally and it’s the belt first!”
Sandi smiled inwardly and decided to add a twist he wasn’t expecting. “Get your naughty butt out here!” Reaching in and grabbing an ear painfully she hauled him out and slapped his hands still trying to pull up his jeans. “Nevermind with that dirty little boy, they can stay down for now!” Pushing him over the hood of his car she slid his own belt out of his pants and stepped back, watching as he lay there shivering his humiliating panties bunched up in crack of his cheeks, his jeans now just below his bottom. Folding the belt she gripped it then leaned over and yanked his jeans down farther to his knees wanted soft thighs to feel this too. Then she stepped back again and ordered, “Pull your shirt up out of the way and hold it there and push yourself a little farther forward over that hot hood!” Reaching under him she helped him move forward until she felt that the heat would be felt intimately and painfully if he move too much more forward. Grasping his cock she pulled it forward under his belly and yanked it till it touched the hood. He shrieked and immediately stuck his behind up and back to move it away from the hot metal. She smiled at the sight and gave the belt a few swings eyeing his nicely presented bottom while she did. Keep that bottom up dirty little boy!”
“Yes Mommy”
THWACK! THWACK! THWACK THWACK! THACK! The belt landed hard and fast in sets of five then she would pause and move to his other side and give him the next with a back hand or would switch to her left. He begged and pleaded and yelped and shrieked almost from the start, but he was cruelly ignored and the belt continued it’s work. Mistress watched gleefully as the belt drove his bottom down and forward, forcing his tender cock against the hot hood, then he would howl and thrust it back and up, his bottom meeting the belt as he did.
Finally after twenty five she stopped and ordered him into the house and into his corner.
He made his way as fast as he could with his jeans at half mast, trying not to stumble and at the same time trying to keep ahead of his belt, which she used to encourage him along his way frequently. Once in the corner with his hands on his head properly she pulled his pink panties down to just below his bottom and left him there while she took a breather from his belting. The plug was ignored as were the now very painful clips on his nipples like they did not exist. No mention was made of the one Mistress wore but it was definitely felt in her exertions!
“Come HERE!”
He turned slowly keeping his hands on his head and shuffled to her until he was at her side.
“I am really, really sorry Mommy, please,please don’t spank me please?” he pleaded with her despite knowing it was no use. Why are you being spanked naughty dirty boy?”
“Because I ssssskipped sssschooool and…” he hung his head his cheeks flaming, ” cccause I errr, umm played with myself Mommy”
“I’m waiting naughty one”
He sighed and sobbed and his shoulders slumped resigned to the hell of the next few minutes.
“Please spank my naughty bare bottom with the hairbrush Mommy, blister my bare bottom to teach me to behave” , he waited for her reply anxiously, if it was not convincing enough he had to do it again and again and got the cane after in the corner for how ever many times it took him to do it right times three.
“Too soft I can barely hear you, again”, she made no mention of the cane it was a given at this point.
He repeated it firmly and in a tone easily heard.
‘Yes better, now over my lap instantly!”
Quickly Gerry draped himself over her long shapely thighs, gasping as his cock was grasped and placed firmly between her thighs. Mommy didn’t do this in punishment spankings no pleasure was allowed and if you tried you were in for it. Settling in he clenched his bottom cheeks and Sandi smiled at the sight then tapped those surprisingly plump in this position mounds. He immediately relaxed at her unspoken command and then shivered as he felt her grasp the hairbrush firmly and lift it over her head….
end of V
