Pleasantries

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Bringing the crop up a little harder for a few swats, Sheila managed to make Roxanne jump again from the contact. The swats were immediately followed by light patting. Her eyes roamed over Roxanne's stocking clad legs while she patted her captives belly. Roxanne whined a little in her gag from the additional pain generated from her last startled jump. Sheila's eyes slowly wondered up Roxanne's taught body and eventually stopped on her chin. Her light pats stopped as well. Standing perfectly still, except for lowering the crop down beside her leg, Sheila watched as a strand of saliva slowly stretched from Roxanne's chin. It stretched down to about waist level and then broke, falling to the carpeted floor. Roxanne's face flushed a darker shade of red. Her lover had spotted the drool, and it had embarrassed her.

Walking back to the table with the clothing heaped on top of it, Sheila pulled a hand towel out from a cabinet above it and brought it over to Roxanne. She wiped her toy's chin off and then told her to force what she could out into the cloth. Roxanne tried her best, but couldn't get it all out, but was relieved that the level was significantly lower. Sheila dropped the cloth on the floor not to far from Roxanne's anchored feet, and went to a small chest. The chest's lid opened easily and sitting in a box was what Sheila sought. She lifted it out of the chest, leaving the lid up, and opened the box. After setting the box back down, Sheila knelt down along Roxanne's backside and started running the straps around her waist and legs. She seated a vibrator in the pocket attached to all the straps, and turned it on Roxanne moaned into her gag when she heard the vibrator come to life. This promised to be painful. It would be most pleasurable, but due to her current situation, the pain was inevitable. Sheila immediately went to rubbing Roxanne's pleasure spot and Roxanne moaned immediately. The vibrator traced along her clitoris for a lap or two, then was slowly slid into place. The result was instant, with Roxanne moaning very low and drawn out. Her body began to wiggle and Sheila could see the minute struggles beginning. Roxanne bit down on her ball and closed her eyes.

Another rope was tied to the waist belt of the strappy device that held the vibrator in place, and then passed through Roxanne's legs. The rope was passed under the same belt on her backside and then run to her wrists, where it was tied to the chain in between her cuffs. The slack was pulled out before the knot was cinched down. Roxanne was already building fast and her moans were turning into whimpers. Sheila just smiled and checked the bonds.

Satisfied that her toy was truly helpless, Sheila took the crop and started striking Roxanne's body at random. Each strike had a little sting in it, making her captive flinch each time. The nipples were ablaze with pain, while her pussy shook from pleasure. The first orgasm hit so suddenly that Roxanne was not prepared for it. If it weren't for the fact that she was bound strung up, the climax would have knocked her off her feet. As it was, the orgasm caused her whole body to spasm, and Roxanne swayed in turmoil as waves of pain and pleasure crashed through her body. The resulting struggle pulled her nipples a great deal and caused her body to drive the vibrator deeper into her chasm. All the while as Roxanne struggled, spasmed, and screamed, Sheila stood back and smiled.

Finally Sheila knelt down in front of her and loosened the string from the floor anchor. Roxanne hung by her up-stretched wrists, clearly spent. Her moan contained a degree of contentment as her nipples got to relax for the first time in a long while. The clamps didn't come off however. Sheila grabbed hold of the leash, which has been hanging loose since the session began after initially arriving to this spot. She slipped it around the middle of the spreader bar, and pulled some on it. Roxanne grunted as her head was being forced down. After the body reached what she deemed was it's limit for stretching in this position, Sheila tied the leash off around the spreader bar. Sheila walked back over to the pulley and cranked it up a few more notches, taking all the bend out of Roxanne's legs. The adjustment forced the vibrator deeper into Roxanne.

Sheila walked around her playmate, and decided that she didn't need a change in wardrobe, just another addition. Selecting a blindfold off the wall hook, Sheila placed it snuggly over Roxanne's eyes and buckled it in place. The crop was placed back where it was found and Sheila replaced it with a long, stiff leather paddle about two inches wide.

"Too help you remember tonight, my sweetness." Roxanne lifted her head at that statement, but soon dismissed it as pain shot up through her body. The leather paddle had connected with the backs of her thighs, right above the tops of her stockings. She screamed into the gag, and shook all over. The ordeal was cut off by another swat connecting right under her cheeks. The impact caused the vibrator's harness to lurch up and forward, as well as rock her body with the pain. Sheila continued to unload on the backs of Roxanne's legs and on her ass. The pain was intense. Her tears had soaked the underside of the blindfold. Drool had leaked out in a steady stream from the gagged crying that resulted from the pain.

Twice from the long drawn out ordeal Roxanne orgasmed, but she never had the time to relish them from the continuous spanking she took. Sheila didn't notice the orgasms either, so concentrated she was on turning Roxanne's backside red. Figuring that Roxanne had endured enough, Sheila stopped the spanking onslaught and put down the paddle. Using the paddle handle as a prod, she placed it next to the base that held the vibrator in Roxanne and started pushing it deeper. Roxanne had been on the verge of another orgasm through the drawn out ordeal, and the pleasure returned with the end of the paddling. Sheila watched as Roxanne neared another orgasm. When she saw Roxanne tense up, Sheila tossed the paddle off to the side and reached up to the nipple clamps. When she thought Roxanne was at the peak of her climax, Sheila released the nipple clamps, retuning life, and blood to the nipples. This sudden release sent pain through her body and Roxanne thrashed for a while, biting the ball gag hard and whining as loud as she could. Once Roxanne's orgasm and struggling subsided, Sheila removed the vibrator and the harness. Roxanne looked completely worn, only her bindings were keeping her on her feet.

Looking at the wall clock, Sheila noticed that is was closing in on 11:00. She knelt down and unhooked the spreader bar from the floor and freed Roxanne's ankles. After making sure that Roxanne wasn't going to tip forward and hurt herself while still strung up, Sheila went to the pulley and slowly lowered her tired toy to the floor. The metal cuffs were replaced with leather ones, after seeing how much they rubbed Roxanne's wrists red. The blindfold was removed and hung back on its hook. The collar and elbow bindings were still left on, as well as the harness gag. Sheila picked up a few lengths of rope and walked over to Roxanne.

Kneeling down to pick up the leash, Sheila coaxed Roxanne up to her feet with soft words and stern jerks from the leash. With some assistance from Sheila for balance, Roxanne finally managed to get up into a standing position. Her nipples and backside were still throbbing with pain. Her pussy still tingled from the pleasure. Her head was swimming with mixed signals. On one hand she wanted to collapse and sleep off the pain, while on the other, she wanted a little more pleasure out of the evening.

Roxanne was guided back up the stairs to her bedroom. It was a large room with a king sized four poster bed in the middle. The frame of the bed was brass, with vertical rails at the head and foot of the bed. At the top of the posts were brass rods connecting them, made for hanging curtains or a canopy. Sheila really admired the bed. Roxanne had purchased it thinking of all the possibilities it could provide. It has been well used, and she was proud of the purchase. Sheila walked her over to the bed and helped her sit down on it. The leash was disconnected and dropped on the floor. The rope was tossed onto the mattress and Sheila walked around to the other side and got on the bed. She moved up behind Roxanne and half drug, half guided the woman into the position she wanted.

Before laying Roxanne down on her back, Sheila tied off a length of rope to the link that connected the leather cuffs on her wrists. Then she laid the captive down. Roxanne's body was moved around a bit more, allowing her legs to hang over the brass frame of the footboard. Sheila tied the other end of the rope fastened to the cuffs to the middle vertical bar on the footboard. She then pulled the heels off Roxanne's feet and brought each leg up onto the mattress. Roxanne's body was so close to the footboard that her legs were bent in order to keep her feet on the mattress. Sheila spread those legs to the sides and then tied the ankles to the corner posts, and to a vertical bar near the ankles. Sheila took the last two lengths of rope and repeated the process to Roxanne's knees, securing them wide apart.

Leaving her toy to catch her breath, Sheila went back down into the basement for a few extra pieces of equipment. Roxanne, worn to a point of passing out, tried adjusting her body to alleviate some of the pain on her ass. She finally found a position were the pain was lesser than before and settled in the spot. When Sheila returned, Roxanne had just drifted off to sleep. Tossing the articles up by Roxanne's head, Sheila slid the latex thong off her hips and down her legs. The thong was placed on a chair back. She crawled onto the bed and sat on her side by Roxanne's head. The straps that connected the rubber ball to the rings off to each side were undone and the ball was pulled out of Roxanne's mouth. Sheila picked up the first of her two items, a penis gag built for the head harness, and placed it in Roxanne's mouth. Roxanne stirred and closed her lips over the shaft of the new gag.

The special thing about the new gag was the six inch dildo that was mounted on the opposite side of the penis gag. The padded base to which both sides were attached was shoved all the way to Roxanne's lips, and then the side straps were attached to the rings where the ball gag was originally attached. Once secure, Sheila hiked up her skirt until the hemline was at crotch level. She positioned her pussy over Roxanne's head, and guided the dildo sticking out from her captive's mouth into her wet pussy. The fit was easy and she slid it all the way in, coming to rest on Roxanne's face. It was time to wake the sleeping beauty up, Sheila thought.

Reaching down to Roxanne's nipples, Sheila placed her fingers around the swollen and abused stubs, and pinched tightly. The immediate pain shot through Roxanne's body and she started awake with a flash. Instinctively she tried to bring her hands around to remove the pain, and when that didn't work she tried to sit up. The force jolted Sheila, and she allowed a pleasurable gasp to escape her lips. She forced her hips down and Roxanne became aware of what was going on.

"That's right, Roxy, my turn," breathed Sheila. "And I brought a little inspiration." With that said, Sheila reached back for the last item that rolled up to rest against her foot. She picked up the vibrator and turned it on. The vibrator was rubbed along Roxanne's neck and then moved up to her breasts. Each breast was circled a few times and then the vibrator slowly worked it was to the very sensitive area between her spread legs. Roxanne had already begun to struggle, which in turn was driving the dildo into her captor's pussy. Small moans escaped Sheila's mouth as she leaned forward, resting on her right elbow as her left hand traced circles around Roxanne's exposed opening.

Crossing her ankles to help keep her knees steady, Sheila finally plunged the vibrator into Roxanne's pussy. The instant sensation caused Roxanne to buck a few times, sending jolts of pleasure through both women. Sheila dipped the vibrator in and out of the squirming woman pinned under her, keeping the stimulation and torment at a high level, producing a stronger response and a more active struggle. Roxanne, still sensitive from the earlier action, was bucking her hips at random to keep the vibrator out, but all she accomplished was placing her sore cheeks and backside on her bound arms, sending waves of pain through her body. Sheila had her tied well, and manipulated the vibrator with ease. Roxanne grunted and whined in her gag as Sheila's moans got louder and louder.

Pretty soon Sheila shoved the vibrator into Roxanne's pussy, all the way to the hilt. She had lost track of tormenting her toy as the pleasure took over her own body and she rode Roxanne's face like an animal possessed. Roxanne tried to hold her head rigid, but Sheila's own bucking pounded her head into the mattress. It wasn't much later then the same effect took hold of Roxanne from the vibrator planted in her, and soon both women were thrashing on the bed. Sheila's orgasm exploded over Roxanne's face, with her captor's legs clamped to the sides of her head. Loud moans filled the room as the climax shook Sheila. Pulling herself off Roxanne's head, Sheila fell to her right side to allow her sub to breath. Roxanne needed the air, for she was bucking from the orgasm that finally smashed through her body. Sheila held the vibrator in until the last wave of the orgasm washed through Roxanne.

After recovering a bit of her strength, Sheila pulled out the vibrator and got up. She stripped out of the latex dress and put the thong back on. She untied Roxanne's legs from the bed and dropped the ropes on the floor by the footboard. The head harness was removed and placed on the night stand. Roxanne was drug up onto the bed, with her head placed on a pillow, and turned onto her side. The elbow cuffs were loosened and then taken off. Sheila placed them on the stand, next to the harness and then climbed back up on the bed. She slid her body up to Roxanne's, laying against her toy's backside, and pulled a light blanket up over them both. She leaned over Roxanne and kissed her on the cheek.

"It's a quarter past twelve, sweetness, happy birthday." Sheila whispered into her sub's ear before reaching up and turning off the light. Still collared and hands cuffed behind her back, wearing a garter and stockings, Roxanne smiled as she drifted off into a much deserved sleep. Beside her lay her lover, wearing only a thong and thigh high leather boots. The next day promised to be a good one since Sheila was with her. She was curious as to what little pleasantries Sheila had planned, then a series of erotic dreams took over.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Bound to the Turnings of the Wheel F/f, sci-fi. Erstwhile D/s lovers' reconnection escalates.in BDSM
Caught in selfbondage at College Sissy crossdresser gets caught tied up in friends room.in Transgender & Crossdressers
Portal Gag A thieving secretary gets a fitting punishment.in NonConsent/Reluctance
The Campus My Introduction To The Campus.in Transgender & Crossdressers
The Only Girl at the Party Pt. 01 Mistress forces me to go out, fully dressed, by remote.in Transgender & Crossdressers
More Stories