Chapter 8

One morning Jeff woke Susan from a deep sleep, quickly had sex with her, then told her to get dressed in her prison officer uniform, she was going to observe a punishment. She asked which uniform, because she had several versions, mostly with very short skirts or tight tops that showed her breasts. She was surprised when he told her to wear the new official regulation one, which she hadn't even worn before other than in her room for showings to kinky customers. Jeff even gave her what looked like a proper prison officer pass, with her photograph on it, and told her to pin it to her jacket pocket. The name said "Susan Spencer".

As she walked with him down the corridor between the cells she felt quite pleased, finally allowed to look like a proper guard in front of the other women inmates. Jeff took her out to the yard, and had her sit in a prison van, and drove out of the female prison. This had happened a couple of times before when she was sent to entertain wealthy local residents, but normally for those visits she would wear a skirt so short her bare thighs could be seen above the stocking welts as she sat in the passenger seat. Now she tugged the hem of her skirt down almost to her knees, and smiled confidently at the guards on the gate as she was driven away.

"Where are we going, Jeff?" She knew better than to ask why! She just assumed some wealthy local wanted to play discipline games with her. Perhaps she would have to give the client another over-the-knee spanking! She quite enjoyed those games.

"You will see, it's not far." And sure enough after just a few minutes they turned into the male prison that she had heard about but never previously visited. These guards hadn't seen her before and just assumed she was a real prison officer.

Jeff parked the van and they walked to the main entrance, showing their passes several times as they walked through the building. "It seems that some men have been fighting, and the Warden has ordered that they all get flogged. They are a bit short staffed here so the warden asked if we could help out, and I told him about you and suggested you could help." Susan's heart skipped a beat at this, what role would she be playing in the group flogging?

"Help, how?"she asked nervously.

"Don't worry, you will do fine. Let's go see the warden first. Don't worry, he knows you aren't really a prison officer, and he wants to meet you before you go into the punishment room."

Inevitably the warden, who indeed knew all about Susan's real status, took pleasure in fucking her bent forward over the desk in his office while he chatted with Jeff about the forthcoming group caning. After the warden had cum in her pussy, she was allowed to pull her panties up but not to wipe herself or mop away his semen! She felt really slutty as she walked beside Jeff through the men's prison, going along corridors and down stairs. They passed cells with male prisoners in, who whistled and yelled when they saw her. Susan tried to ignore them but was flushing scarlet and trembling when they finally entered an area labelled 'punishment wing'.

Jeff opened the door and ushered Susan inside. The room was large, and four men were standing naked in a circle, one facing each of the four corners, all with hands tied above their heads to rings in the ceiling, and with ankles secured to rings in the floor so their legs were wide apart! Those who could easily do so looked around to see who had come in, and there was a collective gasp when they saw a lady prison officer.

Susan was glad to see that they all seemed to be very effectively restrained. Because of the way they were standing, she could only see a couple of their cocks, but both of them were semi-hard. Looking across the room, she could see the testicles of the man opposite, hanging between his wide spread thighs.

Jeff told her to walk with him around the room, meet the prisoners. As she did so, all four cocks grew hard. The men were in their twenties or thirties, good looking with fit bodies and, she could now see, very fine cocks! In her role in the solitary cell in the womens prison, Susan often got fucked by the male guards, but mostly they were in their forties or older. She was quite excited to be so close to these four fine cocks!

As they walked around, Jeff casually told the prisoners, "This is Officer Spencer, she's new on staff, this will be a good learning experience for her. She will be doing the preliminaries. I will return later for the floggings, although I might let Officer Spencer perform some of them also."

When she realised Jeff was about to leave the room, she rushed to him and hissed, "What do you mean, I will be doing the preliminaries? What does that involve?"

"It's conventional here that prisoners about to be flogged all have to be figged. They have to be given ginger suppositories to relax their buttock muscles before the caning. The suppositories burn for about fifteen minutes, after which the prisoner is much more responsive to the cane."

Susan couldn't believe what she was hearing! "I have to put ginger suppositories in their bums?"

"I'm sure the men would prefer that you do it, Susan, and it isn't something I want to do. The suppositories are in that box, they are all freshly carved, just take out one for each man."

He pointed to a box on a shelf, and when she looked in it she saw that it was labelled 'Ginger Suppositories' and contained half a dozen ginger clove roots carved to the shape of small butt plugs but without any wide base to stop them going all the way in! There was a box of disposable rubber gloves there too. As he turned to leave, she stopped him, and begged him not to make her do this. He grinned at her, and just said, "Don't worry, they are all firmly secured, they might squirm a bit but they can't hurt you. Use a rubber glove so you don't get your finger burnt as you shove the ginger in."

"I've never done this, please how do I do it? I mean, how far in do I put them?"

"As far up as you can get it. Get the man to lick your index finger first to lubricate it, then push one of the suppositories in his ass and use your gloved finger to shove it as far up inside the man's rectum as you can get it. Each clove has a string attached, make sure you leave that hanging out so you can pull it out just before the flogging."

She looked around at the four men who were now all twisted round and watching her intently. "Please stay while I do the first one," she begged, and Jeff chuckled but said no, she would cope. He even suggested, if she couldn't work out how to do it, she should ask the men, they had all experienced it before. And with that he left the room.

She turned to look at the men, who were now all grinning! "Oh god," she sobbed. Flushing scarlet, she pulled the rubber glove onto her right hand and lifted one of the ginger roots out of the box, then looked round helplessly, trying to decide who to do first. Then one of the men chuckled and said, "Why don't you start with me, Officer Spencer. My name is Jim." The other men all laughed! She went to stand behind him, looking at his firm buttock cheeks and wondering how on earth she was going to force the root into him. His ass cheeks were so tightly clenched she could barely even see his ass.

"Just slip it in, Miss Spencer."

As she pushed it between his ass cheeks, up against his sphincter, he tightened his buttock muscles so she couldn't even see his anus! "Sorry Miss, but it's an automatic response, my body knows it's going to hurt, you need to use your other hand to help me relax." She put her hand on his tummy, very aware that his erect cock was now rubbing against the back of her hand. "No, Miss Spencer, not like that. Just hold my cock, stroke it, and my bum cheeks will soon relax." She thought she should refuse, but the man had asked so nicely that she felt she had no choice but to do as he suggested. So she put her left hand on the man's rigid cock, wrapping her fingers around it, and after stroking him a few times, sure enough she felt his ass cheeks relax and the clove slipped easily inside his sphincter, which then closed to hold it firmly inside him.

But now she had to push it all the way up inside him. She tried to do that with her gloved finger, but Jim asked her politely, "Please Miss, you can't just shove your finger in me there. Let me suck your finger first, to get it lubricated so it will slip in easily. Don't worry, the ginger won't fall out."

She was sure the other men were laughing at her, but Jeff had said she was to do it, so she did, and the man took what seemed to be an excessive amount of time sucking and licking her finger while she continued to hold his cock with her other hand. Finally, when she realised he wasn't going to stop, she pulled her finger out and glared at him. "Now just go round behind me, put your finger inside my ass, find the clove which is in there, and shove it all the way in with your finger."

Flushing scarlet, she did as he suggested, no longer holding his cock with her other hand, and finally asking, "Is that in far enough?"

"Oh no, Miss, it should be much further in. I suggest you kneel down, and really push your finger up in there, as far as you can. But keep holding my cock with your other hand, otherwise I won't be able to relax my buttocks and you won't be able to push it in far enough." Susan was totally confused but couldn't think of any way to refuse, so she did as the man suggested, then when she couldn't push it up any further she drew her finger out, released his cock, and stepped back.

Who next, she thought, looking up at the other three men. She just chose the next man in the circle, walked across to him, knelt behind him, and reached around to take a firm grip of his cock with her left hand before pushing the clove into the man's anus with the finger of her right hand. Then she paused, thinking, did the finger need to be lubricated again? Could she ask this guy to lick it, after he had seen where it had just been? No, that wouldn't be very nice. So she went back to the first man and asked him if he would please clean her finger.

"Yes Miss, I will, for you, of course, but please while I am doing it could you just jerk me off with your other hand?"

Jerk him off? My god, she thought, was that what she should be doing? She looked across at the man waiting with the ginger clove poised just inside his ass. Would he be able to wait, like that, while the first man cleaned her finger? That man smiled at her, and she thought he had such a nice smile that he surely deserved to have her finger lubricated before she shoved it up his ass, so she held it up for the first man, and with her other hand took a hold of his cock. "Is that what you wanted?" she asked, and the man's voice sounded quite strained as he said that, yes, it was just what he wanted. His breathing sounded quite stressed now, he was jerking his hips, and she suddenly wondered if it was the effect of the ginger clove in his ass. "Is that ginger thing starting to affect you?"

"Yes Miss it is. It's starting burning! Please stroke my cock as I suck your finger, it really does help."

Well, that solved the problem of how to deal with the man waiting to be figged, so she was soon able to go to him with a nice clean lubricated finger, which she used to implant the fig right up inside him, while stroking his cock with her free hand. As she drew her finger out, the man spunked! She was a bit shocked by the strength of his orgasm, semen seemed to go everywhere, even on her nice new uniform! Still, too late now. She insisted that he clean her finger even though his cock was in no state to be masturbated, then moved on to the next man.

Showing him her nice clean finger, she gently and smoothly shoved the clove up as far as she could get it. Before moving on to the last man, she offered her finger to the freshly figged man, and he took it in his mouth and started sucking it. Soon he also was jerking his hips and she guessed that the fig was starting to have its effect, so to take his mind off that she knelt and took his cock in her mouth! "Oh FUCK," the man howled as he spunked in her mouth. She stood up, got up on tiptoe, and kissed the man on the lips.