A Sissy Saga

Pain and Pleasure

Lisa had decided not to witness Jackie's punishment, she didn't need to, from her kitchen lair she could hear the slash of the cane on bare flesh, the pleadings, the crying. Lisa counted the strokes, 24, that was a severe beating, Miss Sarah must be really pissed off. The strokes were spaced out, not rapid, that way each stroke is an individual torment not just one prolonged sensation, Lisa could tell from the sound that they were heavy strokes. Lisa felt that it was a make or break, Jackie had only had one or two relatively light canings, this was serious punishment that Jackie could either accept or walk away from. Lisa knew that afterwards Jackie would either walk out of the door or would come to the kitchen for some consolation, Lisa placed a cushion on a chair in case it was the second. Lisa was impressed, Sarah had carried out her punishment calmly, without a raised voice, no personal insults but delivered a punishing retribution, Mistress Jill had schooled her well. After the caning ended she heard Miss Sarah giving a measured and firm lecture to the sobbing Jackie on obedience and loyalty. Jill had sat and witnessed this and was herself impressed. 

Jackie slunk out of the room when dismissed and stood uncertainly in the hall holding her rump with one hand and her skirt in the other. 'Come and have a cup of tea' said Lisa quietly, a teary Jackie, clearly traumatised almost stumbled into the kitchen. 'Let me see' Lisa said gently and pulled down the back of Jackie's panties, the welts were severe but no skin had been broken, even so they would take a little while to heal. 'Wait there honey' and Lisa went to the drawer where all things medical were kept and retrieved a jar of cream that had a cocktail of natural remedies such as Arnica to sooth bruising and sore spots. Lisa smoothed the some of this into Jackie's tortured buttocks, 'this will take a little while to take effect but it will soothe and speed up recovery'. Jackie stood quietly and let Lisa work her magic then gently put Jackie's panties back in place and had to suppress a giggle, Jackie had an erection. Lisa pretended not to notice and guided her to the chair with the cushion and then poured her a cup of tea. She made a decision to further alleviate Jackie's distress, she sat her sideways on the chair and went to her knees. Lisa freed Jackie's erection and took it in her mouth, Jackie gasped at this mixture of pain and pleasure and quickly ejaculated, Lisa sucked it all into her mouth but did not swallow. Instead she stood over Jackie and deliver the semen via a kiss to Jackie's mouth, Jackie took it. Lisa swallowed what was left and looked down at a shining Jackie face, for Jackie, now, pain and pleasure would have a link.

The intercom buzzed into life 'Lisa, a bottle of white and two glasses please', it would be the favourite dry white. Retrieving a bottle from the cooler that always had two ready she took the wine and glasses in. 'Is Jackie recovering?' Lisa was asked and confirmed that she seemed to be feeling a little better and then decided to tell what she had done, the soothing balm, the erect Jackie and the blow job. There were camera's all over the place and while the ladies didn't usually watch live they could see it eventually and questions would be asked. After Lisa had departed Jill and Sarah smiled at each other, Lisa was a very caring girl they decided.

Jackie's head was clearing, but she was confused, the pain in her buttocks seemed to amplify the pleasure of the blow job, which she appreciated as it made her feel more human and less a lump of tenderised steak. In a day or so she would discover that the pain had lessened to become quite a pleasant and erotic sensation that would manifest itself when she sat and moved about. 'Mistress was right to cane me' she suddenly said to Lisa who arched a questioning eyebrow. Before she could comment Mistress Jill came on the intercom 'we are going out for dinner, get something for you and Jackie and show her the flat'. Jackie said she was not hungry so Lisa left her with a fresh tea and went to get a pair of panties for her, can't walk around with that wet spot. She grabbed some clean from the laundry room, Jackie always had spare here. Lisa also grabbed a long tee shirt that on a herself would be a short dress but on Jackie rested on her hips but then who is to see.

Giving Jackie the consolation blow job made her think of Ted, lovely Ted, gentle, patient and with a huge cock. Sadly he has beginning to show his age and his family are pressuring him into moving closer to them to a sheltered retirement establishment. Lisa knew it was coming but perhaps not this quickly but thinking of Ted made her horny. Maybe Jackie could be of some use today after all. 

Lisa showed Jackie into the annex flat that she had recently vacated, Mistress had bought new of almost everything to furnish the basement apartment. The flat was still fully furnished just devoid of anything personal. Jackie was quite impressed, it was actually bigger than the flat she rented. Jackie had seen the sitting room already but not the bathroom, bedroom or small kitchen. This was much better appointed than Jackie's current flat and, wow, that bed looks so comfortable and commented that it was a lot better than she had in her flat and was surprised when Lisa said 'don't quote me but the Mistresses discussed changing it for a new one, this being 5 years old'. Jackie was stunned, she didn't know how old the one was in her flat, she bought the base second hand and paired it with a budget mattress and that was 8 years ago when she moved into the flat.

Lisa jumped on to the mattress, skirts flying, panties flashing. Jackie temporarily forgot the throbbing but subsiding pain in her butt and began to erect in her panties, Lisa smiled and patted the bed, Jackie needed no second invitation. When Jackie had fucked Lisa before it was at the direction of the Mistresses, this time was different and having cum in Lisa's mouth not long ago it was slow sensual and considerate. For Lisa it was not as good as Ted but it was a vast improvement on the last time when Jackie was still Jason. Lisa reached behind and put her hand on Jackie's rump who gasped at the touch on her welts and thrust deeper. The touch did not feel like anything she had felt before, it made her jump and thrust deeper into Lisa but it was sensual in an odd way. Jackie reached round and cupped Lisa, a simultaneous prostate and penis climax hit Lisa and Jackie released at the same time. Jackie thought about what had happened but foremost in her mind was Lisa feeding her own cum back to her. When Mistress has fed her own cum back to her Jackie felt it was quite disgusting but Lisa feeding it mouth to mouth was something else. They had time to freshen up and dress before the Mistresses got back.