A Sissy Saga

As ye sow so shall ye reap

Jason was in shock and had taken another double before realising he could not drive home again, sissy had made it more like a triple hoping that Jason would do something stupid again. Jill and Sarah had made it abundantly clear that what they had would be used if he did not cooperate with them.  It was Saturday and he always watched a game with the boys in the pub on Saturday afternoons, he would have to get a taxi. He had timidly mentioned the afternoon arrangement and was relieved when they said 'no problem, come back for your car tomorrow'. As far as he was concerned the taxi could not come fast enough. He went straight to the pub and had a pub lunch while waiting for the boys. Understandably he could not get the morning out of his head, if any of that got out it would destroy his life. He would stand up to them, they were bluffing he decided, they got the better of the sissy but he was a man. Feeling more assured he tucked into his lunch, the thing with the sissy was a drunken thing and best forgotten. He felt better, finished the beer, ordered a refill and a desert. His phone beeped, he had a text from an unidentified number, might be a scam text, ignore it so he put the phone away. The beer had arrived along with the desert but the phone was nagging in his head so before he ate he accessed the text. It said 'enjoy this afternoon and return tomorrow morning at 9, remember we will destroy your life as you did to sissy if you do not cooperate'. Jason put the phone down, he really had not thought of it like that but, of course, that was exactly what he had done, it had cost Luke his job, his wife and was now a sissy maid.

Jason pushed the Lemon Meringue away, no longer hungry. He had the uncomfortable feeling that they had the upper hand. He was not going to accept that, if they thought he would crumble they had better think again. Sarah the bitch was not going to trap him like she had the sissy, he was trying to persuade himself that he only had a minor role in this and that it was her fault that things had escalated. He would never have done that, he told himself, forgetting that he had deliberately left the photo file open for everyone to see and left his phone open for Mel to hear.

Lisa again came to his mind, the recording clearly showed that he enjoyed taking her and was then alarmed to realise he had a hard on, glad he was sat at a table. 'Hey Jase you look worried', Jason's head snapped up, the four boys stood there 'nah, it's nothing' Jason answered, it was accepted because blokes in a pub do not talk about personal matters, even with long standing mates.

During the televised game the other four noticed that Jason, who normally got right into the match, seemed to have his mind elsewhere. The usual Saturday thing was the match, a few brews after and then a club as all of them were single but this time Jason decided he was tired and not feeling himself, it was no lie, and wanted to go home. The other four decided he must be coming down with something so they got him a taxi to go home. As was about to get in the taxi he said 'by the way boys, I can't do the 5-a-side tomorrow, I have to see a sick relative' and got in. As the taxi drew away the others decided between them that it there might be a death in the family coming up, they won't ask. In a way it was a death in the family but the family member was Jason's ego. He didn't sleep well, sporadic naps were interspersed with dreams, in one he was a dwarf with Sarah and Jill as 7 foot amazons, another saw him being seduced by sissy, the theme was that he was a victim in all this.

The following morning he was supposed to be there at 9 so he got there at 10. Sissy opened the door and curtseyed 'good morning Sir', Jason could not make eye contact and  just brushed past making for the lounge. He burst in 'now listen to me' he said to an empty room. Behind him  sissy said 'the ladies have gone out Sir, they said you were late and they were not waiting, you are invited to sit and have coffee until they come back Sir'. It took the wind out of his sails 'er, ok sissy, coffee it is', Lisa curtseyed and went off to get it. Jason watched as she walked from the room with a very feminine gait. Nice legs, Jason thought and took in the pristine white panties under a classic black French Maid uniform with black stockings and heels. The uniform in question was the original, slightly oversized, one that Luke had bought that had later been shortened and tailored by Helen's seamstress. Returning with the coffee sissy added 'with respect Sir there is one more thing, my Mistresses said that you are free to go but the gun is loaded'. Jason blanched 'what did they mean by that?' Lisa replied 'I have no idea Sir, I am just passing a message' but Jason did know really. Sissy sat next to Jason and rested a hand on his thigh, 'I am sure it is nothing serious Sir' then got up and walked slowly and sensually to the door, Lisa turned 'may I say something Sir?' Jason replied 'sure', Lisa chose her words for impact 'you are the first and only man I have been with Sir and the memory will stay with me'. Jason was taken aback and did not know what to say. No girl had ever said that to him or any kind of compliment after and he had not cared but this hit a spot inside somewhere. Despite himself Jason erected in his trousers, all thought of the ladies banished, they were out after all. Jason justified his thought since sissy was more girl than boy, in fact sissy was a lot sexier than many girls. 

He got up and after a little indecision followed Lisa to the kitchen, Lisa looked round 'can I help you Sir?' she said in a husky tone. She knew the look on his face, she had seen it a hundred times with girls that Jason fancied. Jason was breathing heavily 'would you like me to blow you Sir? Lisa asked, he shook his head 'no, but maybe like the other night, you said you liked it . That was not exactly what sissy had said but she let that slide. 'Would you like to do it here Sir?', Jason just nodded. Lisa turned and bent over the substantial kitchen table. She heard Jason unzip and the trousers fall to the floor, he pulled sissy's panties down and grabbed her hips, he was sober this time and it was not the act of rape that the first time felt like. He entered her in a more considerate manner, to encourage him she gasped. Jason was now lost in the moment and thrust in, fucking her with long and for now slow strokes. It didn't last and the pace picked up as the sex act consumed his brain. Lisa was hoping that at least he would excite her prostate, like Miss Jill did with her strap on, and she could have a sissygasm but as before he was too quick for that and soon in a long deep stroke he buried himself in her and pumped his seed.

'Well, well, fucking my sissy again?', Jason jerked upright in an instant and pulled out as if someone had touched an electric prod to his arse. He turned in shock as Jill and Sarah stood there, he had not heard them come in. He stammered but could but get a word out, Miss Jill turned her attention to Lisa 'get the cane sissy and pull your panties up' Lisa went for the cane as Jill turned to Jason 'you have lost the privilege to watch this, go to the dining room and wait, don't bother pulling up your trousers', he meekly complied and shuffled off, trousers round the ankles. A deeply worried sissy returned with the cane, Jill smiled 'get that joint of meat out of the fridge and put it on the table', a baffled sissy did just that. She wanted to protest her innocence but was halted by Jill, 'this is for your paramour's benefit sissy, I am not upset, you were just following instructions', she then struck the joint of meat with the cane while Sarah between giggles added some convincing screams, 'this needs tenderising anyway' Miss Jill joked. Jason heard the slaps of the cane, lost count at ten, heard the screams and got frightened, was he next?, all bravado consigned to the bin. 

As the meat was getting the caning Sarah applied a heavy coat of blusher to the backs of sissy's thighs 'it will wash off later', she said 'and look like you have been punished' and also round her eyes to make them look as if she had recently cried. Jason stood in the dining room, the front of his boxers soaked where he had pulled out in shock while still pumping and his penis had shrivelled inside the fly of his trunks, trousers still round his ankles. At last the ladies came in, for once he was not assessing how they were dressed, he was a rabbit caught in the headlights. Jill was dangling the cane from her hands 'you do understand that there must be retribution for raping my sissy again? Jill said with emphasis, he just nodded eyes transfixed by the cane, the last time he ever had that applied his mother had done it, a strict lady who brooked no bad behaviour, he felt like he was a child again. 'Your underwear is soaked' Sarah added 'take them off' said with an authority she had used on others at work, even her so-called boss would not deliberately upset her, Jason stepped out of the trousers and boxers. Sissy was paged 'take these away' Jill waved in disdain' and bring some replacements'. Jason looked at the reddened eyes and winced when sissy turned and he saw the backs of her legs. Jill continued 'but I am not your Mistress, Sarah is and she will exact your punishment' and handed the cane to Sarah 'agree or leave the house as you are now and suffer the consequences later', he nodded dumbly'.