Sissy Training
Double Trouble
Andrew was a little pantie pervert but his wife had the measure of him.
A typical evening would see them both enjoy his humiliation as he abandoned his manhood to his peculiar fetish.
The last night was no exception to the almost daily routine. Andrew had finished tidying up the kitchen and had gone upstairs to meet his wife, Katie.
Katie sat on the bed, waiting patiently for him to finish the chores he had been set.
She opened the bedside drawer, “Pick a pair of panties,” she said.
He wasted no time in rummaging through her delicate, intimate apparel. Fingering the lace and silk, he found himself becoming aroused.
“Oh you like those!” She said as he pulled out a pink lace and silk thong.
“Yes, yes, I do,” he replied.
“You had better get them on then,” she teased.
He lowered his jeans and stepped out of them before taking off his boy pants. Sitting on the edge of the bed, he stretched his legs out straight and tugged the tiny panties upwards. Standing up, he pulled them up over his cock and bottom.
“Oh there’s a pretty boy,” she giggled.
Andrew had enjoyed wearing panties since he was a teenager and now, at the age of 42, he was with Katie, someone who encouraged him to enjoy his ‘little kink’. Not that it was his only one!
Andrew blushed a little as he took in a view of himself in the bedroom mirror. He was naked except for the panties that were tenting around his hardening cock.
On the other side of the room, Katie perched on the edge of the bed. Dressed in black PVC skirt and a corset, she looked every inch the Dominatrix.
“Over here,” Katie demanded.
Andrew scuttled around the bed to stand in-front of her. Head bowed, he stood with his hands beside his legs.
Katie patted her lap and then curled a beckoning finger at Andrew. He knew what was expected and set about positioning himself over her lap. In anticipation, his little cock had begun to leak. Katie’s stockinged leg wrapped around the back of his legs to hold him firmly in place while his oozing cock pressed against Katie’s other leg.
Andrew’s pert bottom looked so sweet in her panties and Katie would enjoy spanking it soundly. Wasting no time, she began to spank him. Absorbing the energy of her swats, Andrews bottom bucked with each blow.
“Stay still,” Katie demanded. “And don’t think I haven’t noticed the mess you have made on my stockings!”
“Yes Mistress,” Andrew replied. “I’m sorry Mistress.”
“You will be!”
Katie tugged the hem of the little panties down to expose his reddening cheeks and then resumed the punishment. Her spanks rained down faster and harder.
“Ouch, ouch, ouch,” cried Andrew.
Suddenly, out of the corner of his eye, Andrew caught sight of someone in the doorway. It was Katie’s Sister, Helen. Grinning, her arms folded with satisfaction, she stood there, watching.
“Hello Andrew, how’s your bottom?” She laughed.
Squirming, Andrew wriggled and Katie had to tighten her grip on his legs. He couldn’t believe the predicament he was now in.
Katie looked across at Helen.
“Would you have a look in the wardrobe? There’s a cane in there.”
“Ok Sis,” Helen giggled. “I have a little something in my pocket too.”
Helen grabbed the cane and then stood beside Katie. From her pocket, Helen pulled out a butt plug.
“That’s not so little!” Laughed Katie.
“Have you got some lube?” Asked Helen.
Katie pointed to the bedside cabinet and Helen found the bottle.
“Hold his arse cheeks open,” she said.
Katie sank her polished red nails into Andrew’s cheeks and pulled them apart. Helen held the bottle over his little hole and squirted the gloopy lube out onto his rim. Andrew felt the cool liquid puddle around his arsehole. Without hesitation, Katie plunged in the plug.
Andrew gasped as the cold metal was forced into his tight hole. Suddenly, he felt full. Katie pushed Andrew off her lap and stood up. Andrew was on all fours on the floor as Katie tiptoed around him.
“Helen, as you have the cane, I think you should use it!” Katie suggested.
Andrew’s head was swimming. Having had a sound spanking already, now he was to receive a caning from someone who had never seen him naked or touched his body. Between his legs, that cock of his was hard and twitching.
Across the floor, the lovely Helen began flexing the cane between her hands.
“Right Andrew, I’m going to give you sixty strokes in batches of six. Do you understand?”
“Yes Helen,” Andrew Meekly replied.
“On the bed on all fours,” Helen ordered.
Cane in hand, Helen prepared herself to beat poor Andrew’s ruddy cheeks. Helen raised the cane over her shoulder and brought it down across the centre of Andrew’s bottom.
“Oww!” Yelled Andrew.
Delighted that Andrew was being humiliated, Katie watched her sister continue the caning.
Each stroke was expertly delivered. Helen had done this before and she had no difficulty in targeting each stroke evenly across his bottom. Andrew hadn’t a clue about Helen’s own experiences with BDSM, but now he was receiving an education.
With ferocious force, Helen landed the 6th stroke of the cane and Andrew buckled under its impact.
Could he take all sixty strokes?
Laughing, Helen and Katie enjoyed watching. Andrew recover his posture.
The caning continued. Andrew was taking each stroke in his stride. Chemicals in his body were beginning to dull the pain and make his head fly away into sub space.
As the last stroke landed, Helen laughed.
“There’s a pretty boy,” she cooed.
