All six witnesses, to his humiliation, stood up and clapped. He was so taken aback that his cock deflated as he watched them applauding him.
“Well done, Pete. We’ve never had such an open admission from a first-timer.” Toy spoke up. “I don’t know if you are pleased or not, but there is one more of our friends here who is blessed with a fully functioning set of male equipment under her costume. If you can guess correctly, you will be permitted to take her cock in your mouth as well.”
Pete wasn’t sure if he was pleased, shocked, excited, horrified or what. It looked like he was the centrepiece for all of the staff and each of them would provide him with something this afternoon. He studied the two remaining ladies, already rejecting Mary and Miss Marx as the third ladyboy. So, it’s the other nurse or the dominatrix, he mused.
An Indian girl, with smooth skin and sultry eyes, straight black hair and a confident mouth. He didn’t know what he was looking for, having been fooled previously by both Toy and Ming, but now he was beginning to see some slight differences. Nope, the boobs in the leather bra look too soft to be silicone and there’s even a slight impression of pussy lips pushing against the soft leather shorts. No room for a dick in there. It must be the nurse.
She stood, returning his scrutiny, puffing out her breasts within the white uniform and her hip tilted to one side. She smiled at him and swallowed. He noticed the adam’s apple bob up and down and knew the answer. He wasn’t disappointed. She was very pretty, olive skinned, around an inch taller than Pete, with shoulder length, straight dark brown hair and sparkling green eyes. She licked her lips and pouted. Pete smiled at her and raised his eyebrows. His cock, now completely flacid for a change, twitched as he remembered he was in total bondage.
“Hello Nurse.” He said.
Ming clapped her hands. “Correct, Pete. This is Nurse Ann. She has been with us for six months now and has many clients seeking her ministration and treatments. She has been good enough to keep something in store for you. Mistress Anita is the last of our sextet. She too has something for you which you will learn more about in due course.”
Anita approached Pete and reached out her hand, taking hold of his slowly thickening shaft. “Yes, Pete. I am playing the Mistress today, and I detect that although you have already been awarded one Red Stripe for your earlier hard on, you are allowing it to return. Do you wish permission for this?”
“Yes, please, Mistress Anita. Please may I be allowed to have an erection?” he implored.
“Absolutely not, slave Pete. I forbid it. A repeat offence carries double the punishment, don’t you know, so if this grows more than ninety degrees, I will award you two Red Stripes on top of the one Mary is going to give you.”
As she spoke, she was kneading Pete’s cock and it was rapidly filling. There was nothing he could do to prevent it. Within less than a minute, Anita had brought Pete back to full thumping erection.
“Oh, slave. How sad am I; now I have to give you two Red Stripes. Does that please you, slave?” she taunted him.
“Thank you, Mistress. I am glad to submit to you. Thank you for awarding me a caning. I know I deserve it.”
Pete was assessing his situation. Here he was bound naked and spreadeagled in a room with six professional dominatrices. Three of these are ladyboys and at least two of them are going to fuck him in the arse with what he already knows are pretty big cocks. He is likely going to be forced to swallow all of their cum and probably his own too, and he knows that his own one is going to be huge. Three ladies are going to cane him, one six strokes, another twelve, and the third one will add the extras.
Great! This is what I’m here for, he reminded himself.
Toy unbuckled him from the cross and he was able to stretch his arms and legs a bit as Mary and Miss Marx heaved an item of furniture into the centre of the stage.
“This is a caning bench, Pete.” Miss Marx explained. “You kneel on the leg rests here with your knees separated and lie over the padded surface bent at the waist. You will be secured by ankle, knee and thigh straps, another over your torso and your wrists will be secured beside you. Like the massage table, there is a hole for your cock so it can be available to your mistresses and a padded space for your face to look downwards at the floor. Your head will be below the level of your bottom. You will be in completely immobilising bondage and unable to escape. You will not be able to avoid your punishment in any way. You will be released only when we say so. Do you accept your fate so far?”
Pete’s cock gave the reply. It jumped and throbbed and he wished he could give it a stroke but knew he mustn’t touch it. “Yes, Mistress. Thank you. I deserve my punishment and I am willing to receive it.”
He approached the device and placed himself as instructed, kneeling on the padded leg rests and bending down to place his face in the padded holder. He felt the straps being buckled into place, rendering him at the mercy of these six ladies. His knees were well separated, and he realised just how vulnerable he was when fingers trailed over his bottom cheeks and down the divide. His anus reacted to a fingertip playing with it. He was on full display. His wrists were secured down by his hips and his buttocks were raised and in the perfect position to be struck by the cane.
Pete now realised that he could see nothing of the proceedings. No mirror this time to afford him some idea of what or who, nor even to anticipate when. He could raise his head but all of his mistresses were behind him.
“That’s right, Pete. You can’t see much. I hope you are comfortable. In this position we can all see your anus. And Toy is going to fuck it before you take your first Red Stripe punishment. Would you like that?”
What choice do I have? Pete wondered to himself. I came here wanting this to happen. I stripped naked for them and let them tie me down in such a position that they can fuck me in the ass and whip my buttocks as much as they want. I didn’t know there would be a crowd of them but that’s quite exciting, especially as three of them are actually girls, so I’m getting the best of everything. The more I think on it, the more I like this.
“Yes, please Mistress. I would be honoured if Mistress Toy would take my anal virginity. Please, Mistress Toy, fuck my ass while your colleagues watch me submit.”
Toy wasted no time in satisfying his request. She stripped herself naked within moments. All the staff here were accustomed to nudity and they had all seen each other performing naked with their clients, satisfying not only the client’s desires but also their own. Toy asked Ann to smack her cock into life. Ann took Toy’s cock in one hand, rubbed and stroked it for a moment, and then gave it a smack with her other hand. Releasing it, everyone other than Pete watched as it pulsed into arousal, growing larger at every heartbeat. Within a minute, she was fully aroused and her cock bobbed as she approached Pete’s head.
“Look at it, Pete, and give it a kiss. This will soon be inside you. Lick it, slave.” She pressed it towards his mouth and Pete opened up his lips to accept the pounding cock, rolling his tongue over the purple head and giving a gentle suck. Already he could taste the pre-cum.
Reluctantly, yet in anticipation of what was to come, Toy withdrew her erection and walked around to view Pete from behind. Buttocks spread, legs strapped into bondage, tight scrotum containing Pete’s balls, she slipped on a ribbed condom. Applying liberal amounts of lube to her now very eager dick she positioned it at Pete’s secret entrance, not so secret right now with six pairs of eyes focusing on it, and pressed against his anus.
Pete felt the object probing and testing the resistance of his butthole and did not fight back. The head of Toy’s cock slipped in, stretching his anus, but with all the practice he had given it over the past weeks, not uncomfortably so. She pressed again and another inch slid past the asshole and deeper into his rectum. Pete pressed back and relaxed his sphincter, encouraging a deeper invasion and with a final push, Toy was balls-deep into Pete’s ass. Pete gasped in pleasure as he felt the thing fill him and Toy began to thrust slowly in and out, retreating almost the full length of her cock and then gliding it back in as far as she could go. Pete could feel the ribbing on the condom and his cock leaked pre-cum as he remained bound tightly in position and Toy slid in and out of him a couple of dozen times before withdrawing completely.
“There will be more of that later, Pete,” she informed him, “but first we want to see you caned.”
Pete was glad he had had the foresight to cleanse himself by self-administered enema before his visit today. He had even slid his largest dildo up into his ass with liberal use of lube to be prepared for the fucking he knew he was going to take that afternoon. These precautions were paying off now, as he considered how easily he had accommodated Toy’s cock. He hadn’t anticipated his audience though, nor his reaction now to having been watched by all these beautiful young people as he had submitted to a ladyboy ass-fucking. The little blue pill wasn’t really necessary after all – he was massively turned on at his humiliation, the sensations he had just experienced in his ass and the concept of ‘more of that later’. But now he was to be caned, another thrill that he looked forward to.
“Thank you, Mistress Toy, for fucking my ass. May I now please submit to a caning?” he whispered, but loudly enough for everyone to hear him.
Mary, the tall girl in the nurse’s costume stepped forward. She had enjoyed the show so far and was looking forward to her part in Pete’s afternoon.
“You may request your caning from me, young man. I awarded you one Red Stripe.” She said, adding “Do you remember what it is for?”
“Yes, miss. I remember. I allowed myself to get an erection in front of all you ladies and I failed to hide it from you. You all saw my shameless display and I deserve to be punished for it. Please give me the caning you promised me.”
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