A Sissy Saga

A bit like training a dog

Before they entered the dining room Jill had a few words for Sarah, 'you are in a position of authority at work so I think you should cane him', Jill went a little further 'Jason thinks with his penis and we can use that, the caning must sting but must be light enough to be sensual', we want him to come back willingly until he is properly trapped'. Sarah appreciated Jill's point. One more thing added Jill 'my plan is for him to be your submissive', Sarah smiled broadly 'my very own sissy'.

Jason was bent over the dining room table, gripping the edges and feeling very out of his depth. He wanted to run but was rooted to the spot. All he was wearing were his socks and a t-shirt. The caning made him squeal but to his alarm also turned him on as intended. Ordered to stand up and turn around he did so sporting a full erection, Jill and Sarah smiled 'half way there' whispered Jill. Sarah ran a fingernail along the underside of the shaft making it twitch, Jason gasped as the thrill ran through him 'who is in charge?' Sarah asked as if she were talking to a child, 'you are' Jason replied with a quavering voice, Jason had crumbled and would later realise there was no going back. 'If you gave me oral, Jason, you would expect me to return the favour wouldn't you?' Jason had to admit he would. Sissy had been paged and was standing watching the interchange. 'Do you consider yourself a man of honour?' Sarah asked while gently stroking his cock 'yes' Jason gasped 'since, as you admit, I am in charge will you do as I wish' she smiled. he confirmed he would. 'If you are a good boy there will be rewards', Jason blinked, now close to the edge, 'sissy was fucked twice by you and sissy gave you a blow job', Jason nodded and wanted to cum. Sarah sensed this and let go. 'I want you to give sissy a blow job, to show your gratitude', Jason was about to refuse when Sarah's warm hand wrapped round his cock again, he nodded. This was a surprise to Jill, she kept a straight face but inwardly was laughing her head off.

Jill removed the cage from sissy as Sarah had Jason kneel. With quite a lot of prompting Jason eventually took sissy's flaccid member in his mouth, it was not flaccid for long. Jason suppressed the urge to vomit, it was not supposed to be like this, it was supposed to be sissy sucking him. Sarah was behind him pressing Jason's head in, he could not back off, she whispered in his ear 'do this for me and I will let you cum', Jason tried to think of anything else but sissy had started to fuck his mouth. Jason was crying like a child when sissy ejaculated into his throat. Jill stood behind sissy to prevent him pulling out until Jason had received all of sissy's seed as Sarah stood behind Jason to prevent him pulling back, he had no option but swallow or choke. Sissy eventually went limp and slipped out of her own accord. Jason was left traumatised with shame and just knew there would be more photo's. 'Dry your tears babykins, all done now' cooed Sarah 'you will remember your first cock' she added but Jason did not take in the full implication of that. Sissy had wiped off with a damp cloth and pulled her panties up after Miss Jill had refitted the cage. Sissy was really happy and beamed at Jill, she smiled back and patted sissy's rear. 'Did you bring clean items down?', sissy nodded and handed lime green frilly knickers to Jason who looked at them blankly so Sarah told him 'you cannot drive home just in a t-shirt', Jason looked with horror at the frillies 'but but' Sarah held up a hand to stop him and reached her hand down to resuscitate his erection 'you did agree that I am in charge didn't you?', Jason 'yes'. Sarah smiled 'good girl and it is Miss Sarah, now take off your t-shirt' he took it off. Sarah took it off him, wrapped it round his penis and proceeded to masturbate him, he gasped, Sarah said 'good girl' which seemed to be a trigger and he ejaculated into his own t-shirt. He gave out a low moan as he experienced one of the biggest climaxes he had ever had, he was mentally and sexually exhausted. 'wipe yourself off with a dry part of your t-shirt', Jason wiped himself, 'on with your panties' he was told, Jason pulled them on. being a bit bigger than sissy on the waist they were a snug fit. 'um, my trousers?' Jason timidly enquired, Sarah looked at sissy 'they and the trunks are in the wash Miss Sarah', curtsey, 'oh what a shame, it looks like you will have to drive home in your panties' said Sarah flatly. Jason was mortified but before he could protest Sarah added 'you will have to be careful not to be seen, won't you'. Jill was impressed, Sarah was a natural. 

Sissy retrieved Jason's wallet, mobile car keys and shoes but before he left Sarah told him 'as long as you do as you are told I will not embarrass you at work, come and see me when you get in tomorrow' she let that sink in 'one last thing, kneel before sissy and apologise for your appalling behaviour toward her'. Jason knelt and apologised profusely. 'Sissy see Jason to his car and you do not have to curtsey to him anymore'.  A drained and confused Jason got in his car in just shoes, socks, frilly knickers and the t-shirt wet with his cum that Sarah insisted he wore home. Jason would drive away then hide somewhere until dark when he could sneak into his flat, sissy watched him drive away with some satisfaction.

Sarah and Jill watched him drive away from a window 'I think we have him' observed Sarah, 'a bit like training a dog' agreed Jill as she turned and kissed Sarah.

Jason had driven home along side roads and parked in a secluded lane he had often taken girls to and hoped there would be no courting couples there at that time, he did not want to be accused of dogging and exposed as a pervert wearing frilly knickers and a spunk stained t-shirt. Jason would stay there until dark when he could slip unseen into his flat which fortunately was accessed from the rear of the block. It was an irony that he had chosen the ground floor flat because he could come and go unseen with his own parking space right outside the door.

At last he was in and safe, he threw off what he was wearing and headed for a much needed shower. He was sweaty not because it was hot but through fear of discovery as he was parked. The shower soothed him and his conflicting emotions. The caning had turned him on, no question and the subsequent climax was explosive and, damn, looking at her in a different light Sarah was actually sexy. At work she was all business and in a business suit, out of work she was something else. At work severely efficient, out of work with her hair down extremely attractive. He thought of seeing her panties and stocking tops but it was when his thoughts turned to sissy that he really got hard and began stroking. 

After drying off he picked up the washing, the t-shirt was in a disgusting state, dried and crusted as it was but the frilly knickers were satin and he had to admit nice to the touch, who would know if he wore them to bed. He lay in bed with all kinds of thought running through his head, he decided that, for now, he would go along with Miss Sarah, he could always bail out later. Having fucked sissy twice the idea no longer repelled him and felt his recently satisfied penis stirring. He had not even found giving sissy head as repulsive as he imagined, it was a new experience for sure and lets be honest, he told himself, Miss Sarah ordered it so it had not been his idea. It had been an exhausting day and he slipped into sleep.