Prison Payment Ch. 02: The Guards

A week had passed since my trip to the prison where my husband was incrassated and where sent an evening as a plaything for some inmates to save my husband from a beating. I must admit that I had a few long evening playing with the vibrators that I had purchased for a kinky weekend away with my husband before he got arrested. In fact the longer time went on the more I remembered and the more turned on I got, even the thought of the rough fucking I got at the hands of the two guards made me wet and I had some of my best orgasms with my vibrator pushed deep in my pussy and the image of them taking over that cold steal table

However, what interested me more was the mention of Anal, I have never had anal sex before the thought somewhat scared me, also in none of my past relationships has any guy mentioned that he wanted to "fuck my butt". So I started to do some research online, you would not believe what websites pop-up when you type in "anal sex". So after watching a few young ladies take a good butt fucking, I was amazed at how clean it was and how easy they seem to accommodate a dick in their butt. Then I eventually found an informative website the explained the pros and cons of Anal sex, the site hinted that it could be painful at the start but using a lot of lubricants greatly reduced the first few inches and it is advisable to take an Enema before to make sure that all is clean down there. My curiosity got the better of me, being left alone in the evenings there are only so many Rom-Com's a girl can watch, so dressed in only my bathrobe I decided to give it a go. First I visited the bathroom to empty my bowels, back in the bedroom I took hold of my trusty vibrator and gave it a liberal coating of Vaseline that I found in the bathroom cabinet, scooped a big dollop on my index finger and began to apply Vaseline around my asshole, gently rubbing my asshole felt surprisingly good and I could feel my pussy getting wet, I resisted the temptation to stop and play with my pussy, I grabbed the vibrator lift one leg high and slowly started to insert the vibe in, now this vibe is about 7 inches long and about 1 and half in in diameter, it slid in easy, felt a little uncomfortable at first but the further it went the better it felt and now my pussy was really humming, I couldn't resist my other hand went straight to my clit and began fiercely rubbing as my orgasm was building I accidentally knocked the vibrator's on switch. WOW, my mind exploded with one of the biggest orgasms.

I had spoken to Bill a twice on the phone since my visit to the prison and he seemed more relaxed and happier, my session with his fellow inmates must have done the trick. He did mention something strange that I might be getting a visit from a couple of the guards.

"We need to keep them on our side," Bill said

Not sure what he meant, and a little apprehensive after my last experience with the guards I just acknowledged the request without realising the implications.

The next day, early evening I had just kicked off my shoes poured a large glass of wine and curled up on the sofa to watch the next episode of some boring soap. There was a loud knock on the door, not expecting anyone, and thinking that it was just some Jehovah Whiteness I opened the door. There stood a man mid-thirties, tall dark hair, not unattractive carrying a small Nike sports bag.

He looked me up and down then said "Rosie?"

Using my first name seemed a bit too familiar but I replied "yes how may I help you?"

"May I come in?" and with that brushed past and walked into my lounge.

When I caught up with him he had already made himself comfortable on the sofa, standing in front of him hands on hips I demanded "Who are you and what do you think you are doing?"

"Rosie, I thought that you knew, I am Adam, a guard from the prison, I am here to prepare you for tonight's activities."

My face must have been a picture, I just stood there with my mouth open not sure what to say, then I said "activities?"

"Yes," he said

"Now you know the arrangement that your husband has at the prison, now it's up to you to keep the guards on your side and not make it difficult for him and the other inmates. I'm sure that if the other inmates were to find out that it was Bill's wife that let the side down and we stopped certain visits they wouldn't look kindly on him." He informed me.

My first reaction was Fuck Bill, but there was a knot in my stomach is and my pussy was starting to tingle my mind racing with images of what could happen to me at the hands of one or two of the guards.

I still hadn't said anything when Adam said: "come on let's get started we've only got a couple of hours to get acquainted and get you prepared."

And with that Nike bag in one hand, he took my hand and started to lead me up the stairs towards the bedrooms.

After passing the two spare room he led me into the master bedroom, the room where Bill and I used to spend our nights of passion before he was incarcerated. Adam sat on our bed while I just stood aimlessly in front of him.

"Ok strip" Adam commanded

With my mind still trying to process the events so far I just stood there.

"Come on, come on let's get those clothes off," Adam said

That seemed to snap me out of my trance, "What? No" was all that I could say.

"Now come on Rosie, don't just do it for the sake of Bill do it because if you don't you'll most likely be an overnight porn star when we release the video we have of your last performance" he calmly told me.

Video, Bill told me that the session was filmed but it didn't twig that it might be used to blackmail me. Anyway secretly my body was starting to betray me, nipples getting hard, pussy getting damp mind playing images of what might happen, but morally I must put up some resistance otherwise I must expect that I'm becoming a cock hungry slut.

'Ok Ok" I said

I started to undress while Adam just sat there on my marital bed, once naked he indicated that I turn around and face the wall.

"Very nice Rosie, now let's put these on, I find that it helps move things along quicker," Adam said as pulled my hands behind my back and he snapped a pair of handcuffs on my wrists.

Now naked, handcuffed, feeling vulnerable and turned on I was led into the ensuite bathroom, he put the Nike bag down unzipped it and pulled what seemed like a hot water bottle and a long plastic tube. Adam could see the puzzled look on my face,

"Not seen an enema kit before?" he asked as he pulled out a cone-shaped rubber thing.

I just stood there shaking my head mesmerised by the phallic thing he was holding up.

"Ok let's get you on to your knees" and with that Adam helped me on to my knees.

"Tits on the floor, ass in the air" was his next instruction.

So I leant forward placed my breasts on the cold tiles, which only made my nipples go harder, out of the corner of my eye I could see Adam rubbing so sort of gel over the cone-shaped thing, then I jumped as I felt his hands spreading my buttocks and a finger slowly bring inserted in my butt hole. After I found out that he was just lubricating my hole.

"Now just relax and let it happen, it'll be much better if you do," Adam said

The next thing I felt was pressure being applied to my butt, I'm not sure if Adam did it to relax me or just took advantage of my upturned pussy but he slid two fingers into my pussy which was getting quite wet, he continued to finger me as he applied pressure on the butt plug occasionally tweaking my clit with his thumb, this was driving me wild I could feel my orgasm growing. Suddenly the butt plug popped in and my little butt closed around the slim neck of the plug holding it in place and Adam stopped pleasuring my pussy.

"Now stay there" Adam instructed me while he attached the long rubber tube to the back of the butt plug.

I couldn't see from the position that I was in what was going on but suddenly I felt warm fluid filling my lower tummy, after a few minutes, Adam helped me to stand.

"Stay there for a minute or two," Adam told me.

What else could I do, naked, handcuffed, tummy distended and a plug up my butt. After 20 minutes Adam told me to hover my ass over the toilet while he removes the butt plug.

"Keep them cheeks clenched we don't want to spray shit everywhere," Adam says as he slowly removes the plug.

After I expel the hot shitty water Adam leads me back into the bedroom and sits me down on the edge of the bed.

"Now let's check how clean you are up your arse," Adam says as he pushes me back and lifts my legs on to my chest, my arse slightly off the bed allowing his now fully erect member to point at my virgin hole, having never taken it up the arse before I always wonder what it was like, I was just about to find out, I did think that the first time I surrendered my virgin butt it would have been in a more romantic setting with a guy of my choosing, not being anally raped by a guy I had only know for a couple of hours.

"Wow you're a tight one," Adam said as his cock pushes against my little butt hole. "Seeing I'm your first I'll be gentle this time" as the head of his cock penetrate my arse, then starts to go deeper and deeper, I look down between my tits to see my pussy gaping open and three-quarters of this guy's cock up my arse, then suddenly with one extra thrust he's all the way in. Adam then slowly starts to fuck my arse, the pain I felt at the start the stretching of my little hole and the feeling that someone was trying to push a baseball bat up my bum subsided and then he reached down and gently rubs my clit, which instantly becomes hard, while slowly sliding in and out of my arse he alternates between rubbing my clit and slipping two fingers in my pussy. I strangely get used to this object pounding my arse and with the stimulation of my pussy, I can feel an orgasm building. Then just as I'm getting close I hear a voice.

"Adam, how's it going up there?" a shout from downstairs

"We'll be ready on time" Adam shouts back while still fucking my arse.

"Who's that?" I ask.

"Nothing for you to worry about it just one of the lads that you'll be entertaining this evening" Adam informs me. And with that, he pumps faster and his cock explodes deep in my bum filling my rectum with a load of his cum.

He pulls out of me with a pop and leaves me half on the bed my feet on the floor while he moves over to my dressing table and starts going through the draws. He starts sifting through my lingerie most bought from Agent Provocateur, he throws certain items on the bed next to me, then he starts rummaging in my wardrobe.

"What do we have here," he says holding up the bag of items I bought for a sexy weekend before my husband got arrested, maids outfit, dildo, and nipple-clamps.

"I bought them to please my husband, but he was arrested before he got to use them," I said

"Well shame to waste them, we might as well use them" Adam informs me.

"What? Please," is all I could pant out.

He sorts out my quarter-cup bra, garter belt, seamed stocking, French-maids outfit, 5 inch black stiletto shoes and I notice no knickers.

I hear the doorbell in the distance and voices, I can't make out what is going on or how many people there are downstairs when Adam speaks.

"Come on turn around here get you unlocked and dressed," he says nodding towards the selection of clothing on the bed was next to me.

Without thinking I roll over and offer my hands to be unlocked, he releases me and helps me to my feet. I start to get dressed in the selected attire while Adam sits on the chair in the corner twirling the chain with the nipple clamps attached to each end. I start with the quarter-cup bra, now with the expensive boob-job I had done a few years ago my boobs stay quite pert so the lacy bra is purely for effect. Next I roll the stockings slowly up my legs making sure to keep the seams straight, these are hold-ups so again the garter belt is there for effect. Then I wiggle into the maids outfit pulling it up from my ankles, this is a one-piece small black skirt that doesn't cover the bottom of my arse cheeks and a small see-through lace piny that barely covers my boobs and then ties around the back of my neck. Finally I buckle myself into the stilettos, once dressed I start towards the ensuite.

"Where you going?" Adam asks.

"Bathroom, to do my hair" I say.

"Don't worry it'll be a waste time" he says getting and still swinging the nipple-clamps.

"Now come here let's have a good look at you," he commands

I walk towards him, he indicates that I should turn around, I slowly start to do a twirl and when my back is to him he deftly slips the cuffs back on to my wrists.

"SHOWTIME" he announced.

And with that like the prison officer that he is he leads by my arm out of my room across the landing, as I get to the top of the stairs I can hear what is best described as a bar atmosphere in my lounge, laughing, talking, glasses chinking, it sounded like more than a couple of guy, my heart started beating faster, funny I noticed that my nipples growing hard and a dampness between my legs, was I getting turned on? Adam nudged me on, when I got down stairs and I was lead into the lounge there was about 7 to 9 guys sitting or standing around and in the corner I noticed a woman about the same age as me on her knees hands behind her back wearing only stocking and a garter. Surreal no one was really paying any attention to the naked women in the corner, but when I was lead in the room exploded with comments and wolf whistles.

Here I was standing in front of a room full of strange men wearing a skimpy cheap maids outfit, push-me-up shelf bra, stockings and suspenders clearly showing, handcuffed and no knickers. What a normal good girl would do is turn and run screaming rape, but maybe secretly under everything I am a slut because what I thought was going to be fucking a couple of guys now looks like a full blown gangbang and I'm not running. I must admit that like most women I have fantasized about being taken by two guys at the same time and even the pirate rape fantasy, now I'm facing a gangbang and I am so turned on that I could explode.

"Fucking looks great," on guy said

"Wow what we got here Adam?" another asked

"Quiet, Quiet!" Adam shouts "This is Rosie, she's new on our list so let's make sure she has the full works tonight"

Adam guides me across the room where a big guy with a beard attaches a collar around my neck, then I am pushed towards the back of the sofa, out the corner of my eye I see the almost naked women in the background on her knees sucking a cock of a young man. Then I feel a hand in the middle of my pushing me forward so I have to lean over the back of the sofa, the guy with the beard clicks and a lead to my collar stopping me from standing upright, then I feel my legs being spread and cuffs clicking on my ankles which they must have attached to the legs of the sofa stopping me from closing my legs. I know the short maids outfit skirt would have ridden up exposing my very damp pussy and that in this position my boobs would be dangling down.

"Ok let's start with pussy and mouth" Adam announces.

"Try not to cum in the pussy to much early on, mouth, face or arse if poss. Otherwise, we'll have to get Lesley here to clean her out which will detract her from her other services, keeping us hard." Adam informs the room.

Then it began, I felt a cock nudge against my pussy opening, it slides in so easily.

"Wow she's really ready, so tight and wet" said the stranger fucking me, I couldn't see who it is because a pair of big hands had gripped my head and a cock was being butted against my lips.

"Come on bitch sucky time" I was told

I opened my mouth and let the member slide in, now I was being fucked both ends, my body was building to a slow orgasm until someone lay back on the sofa parted the bib covering my boobs and stated to lick and nibble my nipples, my body and mind exploded, I squealed around the cock in my mouth as I, came long and I'm sure the cock pounding my pussy felt my orgasm too. Then the cock in my mouth came, cum hitting the back of throat, I tried swallowing as much as I could but some escaped and landed on the floor as he withdrew. The cock fucking my pussy pulled out and sprayed cum over my arse, both were replaced quickly, this carried on for a couple of hours, occasionally some guy would be fucking my pussy and notice that my mouth was free and would pull out, rush around me and cum in my mouth on my face or in my hair. Some guys were gentle, some weren't, some came quickly and the rushed to the waiting Lesley to get them hard again, some took their time maybe because it was their second or third time, anyway by the time it was nearly over I was pretty exhausted both from the fucking and the orgasms that rocked my body.

As time went on the room thinned a bit as the guys drifted to the kitchen, I noticed that Lesley in the corner was sucking some guy hard again, he had his fingers wrapped through her hair moving her up and down his semi-erect cock.

"Come on bitch more spit, get me hard" he said

After a few minutes his cock was back to the right stiffness, he push her off his cock and came towards me cock swaying as he walked, he walked round the back of me, now I had been fucked by 6 or 8 guys a couple had lost control and pumped cum in pussy which I could now feel dribbling out and down my slit, being cuffed and tied down there was nothing I could do about it.

"You bitch, get over here" he said looking at Lesley kneeling in head bowed.

Lesley looked up and started to crawl towards him.

"Faster bitch" he said, "or you're going to have to suck me hard again" as he walked up to the poor woman, grabbed her by the hair and pulled her round the back of me.

"Get your face in there and clean this slut out" I heard him say before he thrust Lesley's mouth on to my pussy. She quickly start licking my slit and pushing her tongue inside me.

He let her do her work and then the licking stopped and my pussy was once again filled with cock. Now I had been a bit fucked out and hoped that this guy would finish quickly, I hadn't taken into account that this guy was a real asshole.

"Adam what's up with this bitch? It ain't moving" he shouts

"Here, she's nearly done for this session so let me attach some reins," Adam says.

And with that Adam attaches one of the nipple clamps to my dangling left boob passes the chain around the back of my neck then clips the second clamp to my right nipple.

"Here pull on this" he say to the guy now fucking pussy while I'm still tied, spread and bent over the back of my sofa.

"Thanks" the guy says as he grips the chain in one hand, thrusts cock deeper as says "giddy up".

He pulled the chain so hard that my nipples were pulled near my shoulders, along with the fact that I mistakenly bought the nipple clamps that press harder when they're pulled my nipples felt like they were being slammed in the car door. I let out a loud scream and unknowingly thrust my hips back on to the guy cock. My scream must have attracted some attention because a couple of guys filtered back to the lounge from the kitchen.

"Ride her Ted," one guy shouted as he entered the room.

Ted was definitely riding me, tugging regularly on the chain attached to the clamps on my nipples to keep my enthusiasm up.

"Tell me when you want cum Ted I got a little tick that you might enjoy" Adam said to the bull fucking my pussy.

Adam then lies back on the sofa looking up at my extended boobs.

"Nearly there Ad" Ted grunts.

Without warning Adam unattached both nipple clamps, sparks fly in front of my eyes, my nipples explode in pain as the blood rushes back to them, but what was really unexpected was that my pussy responded too, the screams I made we half the pain and half the orgasm ripping through my body.