Prison guard spirals out of control

Correctional Officer spirals out of control

I always wanted to be a cop but I didn't have a college degree which most departments require these days. So I found a job that was as close as I could get, that was a correctional officer at the local prison. I was hoping that maybe one day that experience will help me get into a department without having to get my college degree.

I was on the job for 2 years, being a correctional officer is pretty boring, albeit, not as boring as it is for the prisoners but we are basically babysitting them which is the ass end of the legal system. Probably no surprise but the inmates lacked any respect for the officers and would routinely call us names, swear, and in some cases even spit or throw feces on us. Again, not the kind of stuff they tell you about when you are interviewing for the job. But our training required us to be professional, not to take things personal; they were simply trying to get under your skin and if they are successful they will continue to bully you, it was their version of having fun.

And it should be no surprise to anyone that you get some femboys in prison, the ones that sway their hips, that have a "daddy" within the prison walls, what most would call a prison wife. Even though it's illegal to have makeup they somehow were able to smuggle it in to try to make them look more girly (some were better than others).

I worked the midnight shift so it was typically quieter while the inmates were sleeping. Actually, it never really gets quiet in prison even at night, there always seems to be a low rumble of noise from toilets flushing, bars clanking, people yelling, etc...

I was getting to the end of my shift just before 7am (I worked 11pm - 7am) when my supervisor asked if I could work a couple hours of overtime as one of the guards called in sick. I always welcomed the extra money so I obviously agreed to work. They needed me to do a prisoner cell move, this is relatively common as there's prisoners constantly coming in and getting released.

I showed up at cell 122 and there sat Yolanda, one of our more "convincing" trans prisoners to be honest. Her actual name is Ty Williams but no one ever called her that, to everyone here she was simply Yolanda. Even in her orange prison jumpsuit she had this aura of sexuality that surrounded her. She was tall, thin, yet curvy, black woman with a sexy smile and flirtatious stare. She had become very adept at using her sexuality to get what she wanted, similar to a hot girl on the outside that never pays for a drink or when she gets pulled over can bat her eyes at the cop so he won't write her a ticket.

All the guards were well aware of Yolanda's tactics to try to flirt with them to try to get favors, it didn't often work but that never stopped her from trying. She still had her male parts because if she didn't she would have been transferred to a woman's prison but you couldn't tell at all, I guess tucking it really does work.

As I approached her cell Yolanda sat sitting with her legs crossed swinging her shoe back and forth with her belongings all bagged up laying on the floor next to her.

"Okay Yolanda, looks like you're moving today, do you have everything ready to go?"

"Oooh, Officer McCarthy, they always send me the most handsome ones. I'm ready to go anytime you want"

She makes a gesture of riding me as if she was on top getting fucked. Of course I was used to the sexual innuendos from her and simply smiled politely and shook my head no. You get desensitized to this type of tak and behavior very quickly while working in a prison so it didn't phase me one bit.

"Grab your things and let's go," I said.

"Oh honey these bags are so heavy I'll only be able to grab 1 so we'll have to make 2 trips, is that okay?"

Shit, that complicates things as I would have to call for another officer because we can't leave her belongings unattended however, we were already short-handed otherwise I wouldn't have been working overtime in the first place. I consider my options...shoot, I might as well just grab her other bag, it will save me time and a big headache.

"I'll take your bag, we can do this in 1 trip," I tell her

"You would do that for little ole' me? I'll have to find a way to thank you...I can think of a few ways...if you are interested?" She teases.

I ignored her comment and grabbed her bag and escorted her to her new cell. On the way Yolanda keeps up with the flirting...

"You must work out, you look so strong, I can see your biceps ripping through your sleeves. You must work out a lot...I like my men strong. I feel so special to have my own personal security...will you protect me from all those big bad men?" She says with pouty lips and face.

As we arrived at her new cell I step aside to let Yolanda walk in and she sits down and says to me,

"You can put my bag over there," she says as if she is a guest at a hotel and I'm her bellhop carrying her luggage to her room.

As I placed the bag down her stuff fell out of her bag and onto the floor.

"Sorry about that, let me gather that up for you," I say.

"You are so sweet, my very own maid to help clean up my room...lol," she jokes.

As I'm down on one knee putting her things back into her bag just slightly off to the side of where Yolanda was sitting. Her leg is swinging back and forth and then out of the blue her foot lightly brushes across on my dick. It was gentle and appeared to be accidental but it was just hard enough to get my dick to slightly harden.

"Mmm...looks like someone is happy to see me," Yolanda jokes.

Whether it's the fact that my girlfriend broke up with me 3 months ago or that I haven't got laid since but I didn't immediately move away from her foot brushing back and forth across my crotch. If I'm honest, it felt good and Yolanda notices I'm not making any attempt to move out of the way of her foot.

"Feels good doesn't it, officer?" She whispers sensually.

"That's it, let Yolanda take care of that little problem between your legs...no one has to know"

Now I could get in real trouble for having any sexual activity with an inmate...not only getting written up but most likely fired. I couldn't afford to lose this job but my cock was rock hard now and I closed my eyes and let you a soft moan.

"You like when I take care of you?" She teases.

Surprisingly I start to feel myself involuntarily moving my hips to the rhythm of her bouncing leg, basically thrusting up against her leg like a dog in heat. I continue to hump faster and harder...I'm getting super horney and need that release...at this point, I could care less about being written up or even losing my job, it just feels sooo good.

I start to lose my balance on the 1 knee and grab ahold of the bench Yolanda is sitting on, I drop to 2 knees as I shift slightly to keep my dick rubbing up against her foot, by now I have my hands on the bench with my arms pressing up against her hips as I straddle her leg some more.

Yolanda starts to run her fingers through my hair and down my face. Then she rubs her thumb across my lips where I instinctively pucker my lips to kiss. She continues rubbing her thumb on my lips similar to how a guy would rub his dick across the girl's lips during a blowjob. Then she applied a little force onto my lips with her thumb and in it went, I started sucking on it feverishly while still humping her leg with my cock on the verge of exploding. I must have looked like some prevert the way I was kneeling, humping, and sucking all at once, but at the time I didn't care. I have one thing on my mind and that's to cum.

Unbenoticed to me Yolanda pulled out her cock with her other hand and started jacking off..

She starts saying, "Yeah baby, suck that thumb like it's a fat cock...that's it, keep going like a good girl"

Her calling me a girl didn't go unnoticed by me, why would she call me a girl...and then it kind of made sense, I was sucking her thumb like a girl sucks a cock. It was so gay but my mind wasn't thinking straight and no one would know anyway.

"Maybe you'd exchange the favor and give my dick a kiss so I can feel good too," Yolanda asks.

As she is saying that she removes her thumb from my mouth, my tongue stretches out to find it...I feel her hand now on the back of my head forcing it down...and then something much bigger slides in. OMG, I'm sucking an actual dick, what am I thinking...I need to stop, but it feels so good and I need to cum bad...just a couple more thrusts and I'll cum and then I can get out of there.

"You look so hot sucking my dick...officer timmy" she knew my first name was Tim and now she is calling me timmy in a teasing way, almost baby talk..."that's right, my little timmy likes his treat...and if you do a good job you'll get a desert soon," she coos.

I've lost it as I start cumming in my pants from the constant friction of her leg and foot swinging and rubbing up against me.

"ugh...ugh"...I grunt as my cock spasms with each thrust of my hips

But as I start to come down off my high I feel her strong hands on head guiding me into her dick. I don't want to stop, not sure why but I feel my dick stir

"Don't you stop until I'm done"

I grunt and shake my head up and down as best I can but it was clear that I'm acknowledging her request. Suddenly she pulls her cock out of my mouth...I'm panting from the lack of oxygen and my excitement...I dart my tongue out of my mouth like a snake searching for its prey...

"Are you my good girl? She asks.

I nod affirmative

"I want to hear you say it, are you my good girl?" she asks again

"Yes, I'll be your good girl"

I hear myself say but it was like an out of body experience, there's no way I think of myself as a girl and I'm definitely not gay. I was caught up in the moment and it was as simple as that.

"And if I want you to suck my dick again you will do it?

"Yes, anytime," I pant not knowing why these words are coming out of my mouth.

Then Yolanda shoves the cock down my throat, almost causing me to throw up from gag reflex. She isn't going gentle as she was doing before, she was skull fucking me and I simply let it happen. Then I hear a loud groan, as cum starts shooting out of her dick into my mouth, it's so much that it drips off my lips down on my chin.

Yolanda says "you're a natural cock sucker, I wouldn't have guessed"

Reality quickly set in, I was on my knees in a cell with a trans prisoner with cum dripping out of my mouth and off my chin. I hastily get to my feet, wipe my chin and straighten out my uniform. I didn't know what to say so I quickly ducked out of the cell and looked around to see if anyone heard or saw us. Looks like this wing is empty, which is why we started moving inmates like Yolanda over here, whew!

It had been a week since my encounter with Yolanda, luckily I have been in a different cell block but now I was covering another officer while he is on dinner break over in C block, where Yolanda's cell was.

As I walk by her cell Yolanda is laying in her bed, once she sees me she sits up and says,"Oooh honey, I missed you"

In a whisper, "Hi Yolanda, you should keep your voice down as it's after lights out"

But what I was really saying is I didn't want anyone to hear her and I talking, she gets out of bed and quickly is at the cell door,

"We wouldn't want anyone to know about our activity would we?" she whispers back. Maybe if you come tuck me in I'll forget about what happened between us last week"

Tuck you in? Clearly a ploy to get me to come into her cell, but that was a 1 time thing and I'm not repeating that again.

"Come on honey, just come in for a second, I promise I won't do anything, plus I have a secret to share with you. But if you rather I tell your fellow guards about us then that's okay too."

Was she blackmailing me? Threatening to out me if I didn't comply? I look down up and down the wing, no one around, lights are on dim and it's relatively quiet as the inmates are sleeping. Fuck it, I need to keep her quiet while I figure out how to cover my tracks.

I slowly reach for my keys to open her cell but before I do I say,

"Now Yolanda, just going to come in for a second and nothing more, understand?"

"Oooh" she quietly squeals, "I promise," as she jumps back into bed.

I quietly open the cell door (it's never really quiet) and dip inside hoping no other inmates or guards notice. I approach her bed and ask,

"What did you want to tell me?"

I knew it was bullshit but I have to play this game while I'm figuring out how to silence her.

"Well my friend really missed you and they asked if I could pass along a message"

"What friend? What are you talking about?"

She pulls back the blanket and it's then I notice that she has her dick out...my heart starts racing and my cock starts to stiffen...what is going on with me, I'm not gay. I've never even thought about being with a guy before, I guess I still haven't, as I think of my indiscretion last week I considered it being with a woman not a man. I guess that's how I was justifying it in my head but how do I explain sucking her cock part? That's definitely gay no matter what way you spin it. But her cock has me hypnotized, I can't take my eyes off of it as I freeze in place while trying to pull her blanket back up to cover it.

Yolanda whispers, "Does my good little girl like what she sees?"

I could only nod as my eyes were still locked on her cock. I feel my mouth start to water as my cock is now fully hard and my mind goes blank (all logic and reason is now gone, replaced with lust).

"Go ahead, get a closer look, it's okay your secret is safe with me," she says softly as she winks at me.

I still stay frozen, both in fear and in lust, I can't think of anything else but there's a small part of my brain that is trying to bring me to my senses...it's telling me to get out of there but my feet feel like they are in cement.

"Doesn't my little timmy want to play with me? Maybe I should call you Tracey instead? Isn't that right...Tracey?"

"I told you, we aren't doing anything, that was a mistake the other day"

"But Tracey, you got me all worked up, are you a cock tease? You know what happens to cock teases don't you?"

"No," I said quietly.

"Cock teases like you deserve a good spanking for being bad. Do you need a little spanking Tracey??"

My cock grows harder, if that's possible, at the thought of getting a spanking from this woman. Yolanda looks down at my crotch and can see my dick is hard, she knows she has me and all she has to do is give me a little push so I go right back over the edge.

"Seems Tracey likes the idea of getting spanked, is that right? You've been a bad girl and need to be punished?

I slowly nod in agreement and then I feel my knees give way and I slowly descend to the floor at the side of her bed. Not knowing what is coming over me I reach out to grab ahold of her cock but Yolanda quickly smacks my hand away.

"Did you get permission to touch my cock?

Permission? What kind of game is she playing? But my dick is running my brain and I slowly shake my head no, still unable to speak. Then my voice crackles as I try to talk, I asked

"Please Yolanda, can I touch your beautiful cock?"

Beautiful? Where was this coming from? I was straight, I had a girlfriend, at least I did up to 3 months ago. I was usually the one getting my dick sucked, not the other way around.

"You may stroke my cock but you are not allowed to suck it, understand?"

This was my way out, if I could just break free from this trance then I can stand up and walk out of the cell. But now I wanted to know what I needed to do to have that lovely cock in my mouth again...it was the classic example of only wanting something because someone is depriving you of it.

"Why not?"

"Because you are a cock tease and you haven't earned the right to have my cock in your mouth."

"What do I need to do to earn the privilege to have your cock in my mouth?" I ask.

"First, you need to promise you will stop by every night...and secondly, the next time I see you I want you wearing panties under your uniform...PINK panties to be exact"

I gulp hard, as much as I know this is wrong and I have no desire to wear women's panties, I could only agree with a head nod.

"Oh no, you know the rules, I want to hear you say it"

I whisper, "Yolanda, I promise to come visit you every night and to wear panties under my uniform"

"What was that? I can't hear you?"

"I promise to visit every night and wear panties," I say a little louder

"What color panties?

"Pink"

"Good girl, you may stroke my cock and maybe tomorrow I'll let you taste it...if you behave"

I immediately grab her cock and start stroking. It feels so good in my hand, it's warm, heavier than mine and probably an inch bigger. Yolanda quickly shoots her cums all over my hand and some even land on my arm. Yolanda takes her finger and rubs it on my hand where the cum landed, then brings the finger up to my mouth and without thinking I open my mouth and start sucking on her cum laced finger.

As I headed back to D block I thought about how I got into this mess...what is happening to me...and why can't I just say no to her? And where am I gonna find pink panties in my size? Wait, what...I can't really wear panties to work, what if someone finds out?