Making Francesca Ch. 05

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy.

As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chair and table in it, instructed Frank to sit down and enjoy the meal. "Mistress Celia will be down in about 30 minutes to inspect your cleaning, and then continue your training, so eat up," Justin said as he set out Frank's supper on the table. He had just finished eating when Mistress Celia and Justin came back downstairs. Mistress Celia instructed Justin to fetch Frannie from her cell so she could watch the inspection of her work. As Justin opened the cell, Frank rose from the chair and waited patiently for Justin to clip the leash to his collar and lead him out of the cell. Once in the bathroom, Mistress Celia had Frank kneel in the doorway with his hands demurely folded in his lap as she proceeded to conduct her inspection.

When she finished, she turned to Frank and said, "Overall, not a bad job, but you missed a spot of soap scum on the shower doors, a water spot on the sink faucet, forgot to clean the hair out of the shower drain and there is smudge on the corner of the mirror. I had already decided to switch from the paddle to the riding crop during tonight's bondage session, but was going to start you out with a mere ten strokes. In light of these deficiencies, I think I shall increase that number by two strokes per, so when we add in the dropped crouton at lunch, that makes twenty stokes with the riding crop tonight. Do you have anything to say for yourself Frannie before I turn you over to Justin to dress you for tonight's training?"

"Yes, Mistress Celia, I do. I want you to know that even though I dread the riding crop, I willingly accept the punishment because I failed you and deserve it," Frank told her, staring at the floor with an ashamed look on his face, tears rising unbidden to his eyes.

"Oh, Frannie dear, you didn't fail me. You just simply didn't complete the task as well as I know you can. Remember the first day of your training when I told you that I don't expect perfection on the first try? I'm using the punishment to reinforce the lesson, and motivate you to try harder. Had you actually failed me, the punishment would be much worse than ten extra lashes with a riding crop, as a few of your predecessors learned the hard way. No Frannie, you haven't failed me yet, and nothing so far in your training indicates that you ever will so keep up the good work and I'm sure you will avoid seeing my darker side," Mistress Celia said in a soothing voice that stopped the tears in Frank's eyes and brought a self depreciating smile to his face. She then walked past Frank, patting him on the head like a puppy, and told Justin to come get her once Frannie was ready for the evening's training.

Justin dressed Frank in his standard bondage lingerie ensemble, but he replaced the shoes with a pair that had slightly higher heels. Justin told him it was all part of the training since most Masters wanted their shemale sex toys in very high heels. Justin then led Frank over to a set of stocks, placed Frank's arms and head inside and locked them shut. The stocks were a bit low so Frank's ass stuck up about a foot above his head. Justin explained that during the initial session with the crop, Mistress Celia liked to have her girls in the stocks since it helped prevent them from trying to pull away, and it enhanced the effect of the lashing by preventing them from seeing when the next stroke was coming. Justin then turned around and went to get Mistress Celia, allowing Frank a very enjoyable view of his ass in the tight leather pants he wore.

With his head facing away from the stairs and stocks preventing any attempt to turn his head around anyway, the only way Frank knew that Mistress Celia had arrived to conduct his bondage session was the clicking of her heels as she walked across the floor to where he was constrained with his ass sticking up, exposed for whatever she wanted to do to it. As her leather-gloved hand gently caressed his trembling, panty covered ass, she leaned forward and whispered in his ear, "Don't worry Frannie, this will be over before you know it, and then we can get on with improving your endurance for bondage sessions."

With a little slap on the ass, Mistress Celia stopped caressing Frank, and suddenly Frank heard a swishing sound followed by a sharp crack and felt an explosion of pain surge through his right butt cheek. The pain took his breath away, and he very nearly forgot to count out the stroke. Just in time he remembered, and shouted out "One." He was barely done speaking when he heard the swishing sound again that was once again followed by a sharp crack and an explosion of pain in his left cheek. This time he was expecting the pain and was able to quickly call out "Two." By the fourth stroke, tears where rolling freely down his cheeks, and after the tenth he felt as if he might pass out from the pain. The rest of the strokes when pretty much the same, swish, crack, pain, and somehow he was able remain conscious through all twenty lashes Mistress Celia applied to his backside. By the time she was finished, Frank was thinking fondly of the seventy paddle swats he had received the night before. His ass was on fire like it had never been before, and he was certain that he would have bruises the next morning. Mistress Celia came around to the front of the stocks and gently patted his head telling him what a good girl he had been to take the lashing so well. At the same time Justin began applying the balm to Frank's tortured ass cheeks. At first the pressure of Justin's hands rubbing the balm in only made the pain worse, but soon the balm took over and the stinging pain started to subside.

Would you like to see what you ass looks like after a good lashing with a riding crop, Frannie?" Mistress Celia asked.

"Yes, Mistress Celia," Frank replied, not really wanting to, but knowing Mistress Celia wanted him to see his whipped ass.

"Justin, hold up the mirror so Frannie can see what her ass looks like right now," Mistress Celia instructed as she too held up a mirror.

Tentatively Frank looked up at the mirror, fearful of what he might see. What he did see though was not nearly as bad as he had expected. On each cheek, he saw a set of red swathes fanning out from the middle with thin white lines between. In a few of the red patches, he saw darker red lines that he assumed were a few broken capillaries that resembled long straight hickies. From the pain he had felt, he expected his ass to look like a pile of raw hamburger and was much relieved to see that he was wrong. He also noticed that his makeup was ruined thanks the tears that had recently flowed down his face. His mascara had run terribly, leaving long dark purple trails down his cheeks, and his eyelids where a purple mess. Seeing himself looking so ridiculous in the mirror brought a wry smile to Frank's face.

"What's so funny Frannie dear? I know that most people don't enjoy a whipping like you just got, at least not at first," Mistress Celia inquired of him.

"Mistress Celia I can assure you that although it was a necessary part of my training, I did not enjoy the whipping. I just realized that I look absurd with my makeup like this," Frank replied, feeling somewhat silly to make a fuss over makeup.

"My, my but you do look absurd with those raccoon eyes Frannie. Justin come over here and fix Frannie's makeup so she looks the proper little sissy slut and not like some lace enshrouded scavenging little animal," Mistress Celia said.

Justin hurried over to the cabinet that held Frank's makeup kit and upon returning to the stocks, crouched down and proceeded to clean off the mascara that had run all over Frank's face before applying a fresh coat of makeup. When Justin held the mirror so Frank could see the finished look, Frank smiled at his reflection. The female voice in his head opined, 'Now we look like a proper girl, don't you think Frannie?' Thing was Frank did agree.

"Ok now that you've got a fresh face on Frannie, I want to start getting you ready for the next phase of your sexual training. I'm sure you understand that the next lesson is going to be on anal sex. But before we go plowing away at that sweet little ass of yours, we need to stretch and relax your sphincter muscles, so over the next few days, you will be wearing a progressively larger one of these," Mistress Celia said as she held up a small butt plug, "Now tell the truth Frannie, have you ever had anything up you ass before?"

"Mistress Celia, I have only had a finger up there once. Back in college some of use got arrested for underage drinking and had to spend the night in jail. Before we were put in the cell, the guards performed a full body cavity search, and one of them stuck his finger up my butt. To be honest, I really did not enjoy at all," Frank told her.

"Well I can see why didn't enjoy that Frannie. A body cavity at the jail is no place to be introduced to the pleasures of anal play. By the time we are done with this portion of your training, I am confident you will enjoy having a cock in your man pussy as much as you enjoyed having Justin's cock in your mouth this morning," Mistress Celia replied.

With that she walked behind Frank and he heard her pull on a latex glove. She pulled his panties down his legs, and suddenly he felt a glob of what have been lubricant land squarely on his tight little rosebud. Next he felt Mistress Celia's finger begin to massage his rear entrance, and start to try to gain entry. He wanted to relax for her, but reflexively clenched up. This earned him a sharp slap on his sore ass, and an admonishment to relax. He forced himself to relax, and soon felt Mistress Celia's lubed finger slide inside his asshole. This was much different than the time the jail guard probed his ass. Instead of just rooting around looking for contraband, Mistress Celia gently worked her finger in and out of his hole, loosening him up. When Mistress Celia worked in a second finger, she brushed his prostrate, which caused a little jump in his cock. He suddenly realized that it had not been hard in days, and that thought concerned him until he remembered reading somewhere that female hormones can make a man impotent and figured that the ones at work giving him breasts must be the cause. His thoughts about hormones and limp dicks were interrupted when he felt the tip of the butt plug against his hole. Mistress Celia slowly pushed it in, slightly stretching him out as the thickest part entered. Soon the whole thing was in and his ass muscles clenched down on the slender neck, effectively locking it in place. It was not a very big one, maybe an inch wide at its thickest, but never the less, Frank's ass felt stuffed full. Pulling his panties back up, Mistress Celia said, "Okay now let's get on the bondage training.

Frank spent the next three hours in various, mostly uncomfortable positions, but one in particular stood out from the rest. Mistress Celia had him lying face down on the hard floor with his wrists and ankles all cuffed and linked together above his lower back. It might not have been too bad, but for the spreader bar opening his knees as far as they would go. Luckily, she only kept him that was for about 15 minutes before moving on to something else. To make matters worse, every time he moved, Frank could feel the butt plug shift around in his ass. The effect was making him very horny, and he was certain that if not for the hormones, he would have been sporting a rock hard boner. As it was he could feel pre-come moistening the front of his panties. At one point he looked down and saw a dark spot growing in his panties and was embarrassed, hoping that Mistress Celia had not noticed. She had noticed however and knew that when it was time for her Frannie to get fucked in the ass, she would be ready and willing.

Soon the bondage session was over, but before turning Frank over to Justin to get ready for bed, she told him that she would be going out of town for a few days and that while she was gone, Justin was in charge of his training, and that she expected him to obey Justin as if he were her. Besides she told him, his next set of lessons would revolve around improving his domestic skills, so there would not be much for her do anyway. She also told him that Justin would continue the bondage session, but he would be spared the spankings and whippings until she returned. With that she leaned over, since he was kneeling with his wrists bound to his ankles behind him and kissed him lightly on the forehead, saying, "See you in few days Frannie." She then turned and walked up the stairs.