The Prison Volunteer

“Rachel Andrews,” the guard called my name from behind the security desk.

I stood and glanced at the large mirror in front of me. Pulling my white long-sleeved shirt taut and adjusting my beige skirt, I walked around the other men and women sitting in the waiting area for their turn. I didn’t know if they were all applying to be volunteer teachers at this maximum security prison like I was, but I hoped at least a few of them were. I was nervous and didn’t want to be the only one going through this process. I had never been in trouble once in my life–not even a parking ticket–so stepping inside a prison was a terrifying experience for a private school teacher such as myself.

“Rachel Andrews?” the guard repeated when I stepped forward.

“Yes, um, hi. That’s me,” I smiled and waved awkwardly.

The guard’s eyes looked me up and down, which I thought was rude, but then used the butt of his pen to point over his shoulder, “Go ahead.”

I followed directions andstepped around the security desk, following the hallway to the metal detector. I was supposed to have an informal interview with one of the supervisors there and then receive a brief tour. I figured once I was familiar with the prison, my nerves would dampen. All the bad men were locked up, after all. Nothing could happen to me while I had all the correction guards at my side.

I brushed my long blonde hair over one shoulder and nervously ran my fingers through it. As I approached the short line of people queuing for the metal detector, I read the rules in bold black print on a white sign:

‘Rule 1: No guns, knives, pepper-spray, or any other weapons on prison grounds.

Rule 2: No alcohol, tobacco, marijuana, or any other drugs on prison grounds.

Rule 3: All volunteers must produce a valid state-issued photo ID upon entering the building.

Rule 4: All volunteers must register at the front desk.

Rule 5: All volunteers must produce a signed copy of the prison-volunteer form.

Rule 6: All volunteers are issued a prison-volunteer pass that must be displayed at all times.”

Rule 7: All volunteers must pass through a metal detector. Women are advised to not wear bras with underwire as this may set off the detector and result in a strip search.’

Shit! Rachel… Panic flooded my body as I realized I wore a bra with an underwire. How could I be so dumb, of course I’m going to go through a metal detector!

Those in front of me went through the machine without issue, and then my turn came. I approached the scanner and turned as I walked through. Sure enough…

Beep! Beep!

The guard eyed me sternly. “Do you have any metal on your person?”

I made a face begging for sympathy as I leaned forward to whisper, “I think my bra has an underwire–I’m so so sorry.”

The guard looked down at my large breasts that were hugged tightly by my sweater, then looked back at me.

“Derek,” the guard called over his shoulder.

“Yeah?” a man replied from a back office.

“We got another one,” the guard said and looked on to the next person approaching the metal detectors.

A few seconds later, a young man came to the office entrance. Derek was tall with short brown hair, a well-groomed five o’clock shadow, and broad shoulders that filled out his correction officer uniform. He smiled approvedly at the sight of me, and I couldn’t help but blush. The young man was easily fifteen years my junior as I was pushing forty years old, and yet I could tell the handsome boy was ogling my body. A middle-aged woman had to take her compliments where she could.

“Right this way,” Derek said, nodding me back into his office. I followed him, and he closed the office door behind me. “My name’s Officer Cross, and you?”

“Um, Rachel Andrews,” I spoke nervously. To my surprise, the office was large, more like a conference room and dimly lit. In fact no lights wereon in the room. The ambient light came from a one-way mirror that viewed the waiting room I was just in.

He was watching us the whole time through the mirror.

“Right, Ms. Andrews–“

“Mrs. Andrews, sorry,” I smiled, apologizing after correcting the young man. It was about this time I realized the guard’s pants were unzipped and straightened a little.

“Of course, Mrs. Andrews.” Derek flashed a bright smile and gestured to the large diamond ring on her left hand. You told my colleague you’re wearing a bra with an underwire. Is that correct?”

“Yes, I’m so sorry. I didn’t realize–“

Derek held up a hand as half sat on the edge of the desk, smiling at me. “No worries, but we do have to do a pat down, search, potentially a strip search, and perhaps more.”

“Is that really necessary? I mean, I’m a high school teacher with a Master’s degree in English, and I teach at a prestigious private school. I’d never do anything illegal or bring anythingin.”

“We’ve had a huge problem of unlikely people bringing in paraphernalia as of late, so yes, it is necessary. Unfortunately, we do not have a female guard working so if you wish to enter today, you’ll have to be okay with me performing this search.”

Shock surely covered my face as I felt my heart clnch in my chest with disbelief.

A strip search done by a man? Surely, he can’t be serious. This is outrageous!

“Um, I-I don’t know…” I stammered.

Derek shrugged, “You can always reschedule your appointment.”

I nodded in thought and glanced twice more at his unzipped pants. To my surprise, once the shock of the proposition wore off, something of a thrill sparked inside me. My marriage’s sex life had been a timing thing for the first five years and next to non-existent for the last seven. I swear if it wasn’t for wands and batteries, I wouldn’t have survived to middle age. But the thought of having this young man put his hands on me… Not onlywas kinda hot, but it also felt like a loophole.

It’s not cheating, right? It’s just the law.

“Uh, okay. Sure,” I finally replied.

Derek smiled and guided me over to the one-way mirror. On the floor in front of the mirror were four Xs taped to the floor in red electric tape. Derek pointed to the two in the center and said to stand on the while putting my hands on the glass. I Followed instructions and felt strange seeing the dozens of people sat in the waiting area staring at me. Of course, they all couldn’t see me but it still felt odd.

Derek’s pat down began professionally enough. He put on two black gloves and rubbed over my shoulders and down my right arm to my wrist and then my left. His hand was strong and firm but his grip didn’t hurt. When his hands went down my back, I couldn’t help but pop my round ass a little bit–kinda like I was showing off I guess, but he stopped just shy of my butt cheats. I felt his fingers rub around my waistline tothe front and began to rub up my taut belly. Rising up higher and higher until he cupped my breasts.

“Ohmm…” I gasped and quickly forced my lips closed to avoid any further embarrassment. His hands squeezed both of my breasts, then lifted and fingered in between them for several seconds.

Satisfied with what he felt, his hands came back around and continued their way down my ass. My head was levitating as he rubbed down my thighs and then back up. I had a slight panic as he rubbed back up my inner thigh–worried he wouldn’t stop, but at the last second, he pulled away.

Releasing the breath I held in, I stood straight and turned around. Trying to get the pink out of my cheeses, I smiled sheepishly at Derek. “All set?” I asked.

Derek made a face and shook his head. “I don’t think so. The problem with underwires is that it’s easy to conceal things in them. I’m afraid we’ll have to continue to the strip search.”

“What?” the color finally left my face as I wondered if I should text my husband first to ask for permission.

“Is that a problem?” Derek asked. The boyish niceness in his voice was gone, and an announcement became more prevalent.

“N-No, um, okay. W-What do I do then?” I mumbled, losing my self-assurance.

“Stand here again,” he ordered and pointed to the Xs on the floor.

“Okay, do you want me to take my clothes off or–“

“Did I tell you take your clothes off?” he asked in a stern tone.

“No, I’m sorry, I just thought–“

“Okay, I need you to just do what you said during this security search. I’ve found knives and guns before. This can be very dangerous, do you understand?” he barked, shrinking me into a cowering ball.

“I’m sorry,” I whimpered.

“Stand here.”

I moved to the same Xs and felt Officer Cross step behind me. His hand grabbed at the bottom of my sweater and roughly pulled it off of me, and suddenly I stood before the one-way mirror with dozens of people staring in my direaction, and I was not wearing any top except my bra with an underwire. For a brief moment, my arms were crossed over my chest protectedly, but Officer Cross pulled them away.

“Put your hands on your head and don’t move them, do you understand?” he ordered into my ear.

“Y-Yes, yes,” I shuttered as he roughly forced my hands on my head. My large breasts bounced with every movement.

Officer Cross’ hands grope my chest again, but this time it was rougher. My nipples were hard, and when he gripped my breasts through my bra, I gasped and bit my lip as he rubbed rough circles into my fat tits.

“What are you hiding?” Officer Cross grew into my ear.

“Ooo. N-Nothing. Nothing. I swear,” I yelped.

“We’ll see about that,” Officer Cross said. Gripping the lip of my bra, he yanked them down so they slid to my belly, making my boobs jiggle and bounce free. Just when the guard did this, a man and his wife seated in the waiting area laughed and looked right at me in the mirror. It was as if they could see right through and were staring at my enormous tits as they bounced around. Biting my lip and furrowing my browser, I squeezed my tights together as I felt a squirt of moisture form in my panties.

I couldn’t help it. I had never been watched before. I didn’t know. I never knew how… how hot it could be to be… seen…

After Officer Cross unclipped my bra and let it fall to the floor, I felt his hands pull and stretch my skirt over my bulbous ass cheats and pull them down until it fall to my high heels. Now I was just down to my pink panties. I had been panting in a stare at the different faces watching me, I had forgotten completely about Officer Cross until he spoke.

“What do we have here?” he asked as his hand traversed around my Waist.

I looked down and, to my horror, saw the front of my panties were absolutely drenched. They looked as though I had just stepped out of the pool.

Oh my God, Rachel! This is soembarrassing!

“Oh, I’m sorry, I-I–“

Officer Cross glared at me as he stood to my side. “It is a federal crime to bring any unauthorized liquids into a prison.”

“No, No, I’m sorry, it’s not. I’m not–No. I’m–I’m just a little, um, excited…”

“Are you lying to me?” Officer Cross asked.

“No, I–Oh my God–this is Just so embarrassing,” I whispered as I began to remember my husband, my private school teaching career, and my elegant life outside of this room.

God, what am I doing in here? This is so wrong!

“I have to check to confirm,” Officer Cross said, but before I could respond, his fingers were already rubbing over the surface of my panties.

There was no hiding the wave of pleasure that crashed over me as I felt his finger circle my clip several times. My browser furrowed and my breath became labored while my hands still hung from my head.

“So you’re saying all this liquid substance is coming from you?” he said as herubbed faster and pressed harder.

“Oh, yes, I… I… Oh my God…” I gasped as my knees began to buckle. “I’m sorry–I can’t, um, I can’t–“

Leaning forward, I scratched a hand against the one-way mirror to prevent myself from falling over and garnered everyone’s attention in the waiting room, but I was quickly corrected by the guard.

“Hands remain on your head unless instructed otherwise, understand woman?” Officer Cross ordered.

“Oh God–yes. Yes…” I gasped as I put my hands back on my head. My knees buckled, and I nearly fell into a squat as his fingers molested my pussy so good–God. He was playing me like a fucking piano. “Oh my God…”

I while in a high-pitched squeal as the orgasm built in a hurry and emptied in a sudden rush. My thick thighs quivered, and my breasts shook as I came. The squirt of juices made a wet sound against my soaked panties and rained a few drops down on the floor and my high heels.

Officer Cross removed his hands fromme and began removing his gloves as he shook his head in dismay. He spoke to me but my head was swimming and the disorientation was so strong I was surprised I remained standing. The guard was upset and yelling at me, but I forgot what I did wrong. I remember hearing the words ‘cavity search’ and agreeing to it, but I didn’t understand them.

Hands pulled my panties off, and I awkwardly stepped out of my skirt and panties. I started to take off my high heels, but Officer Cross told me to stop. That he wanted me to keep them on. When I finally got my wits about me, the corrections officer was pointing at the floor and barking orders at me.

“Stand on the Xs, Woman. No, not those. The wide ones. The farthest apart.”

I looked down as I stood uncomfortable wide in front of the one-way mirror, completely naked.

“Wha… what’s happ–“

“Quiet. I’ll ask the questions,” Officer Cross ordered. With his bare hand, he circled my clip several times, making my eyes go wide, and my hands grabbed at his shoulders to brace myself. “No, put your hands on the glass, now. Assume the position!”

My palms pressed on the cold glass just as his two middle fingers slide deep inside me while his thumb rubbed over my clip.

“Oh my God… Oh my God…” I panted as my hips swayed. “Jesus Christ…”

“You’re so wet, is this what you’re doing here? Sneaking contrast in your wet cunt?” he grew and sounded angle.

“What? No. I-I no…” The correction officers’ fingers pumped in and out of my pussy harder and deeper my making me throw my head back as I moaned. “Oh shiiiit. God. Oh my God.”

Officer Cross’ other hand groped at my breasts. Pinching my nipples and plucking at them, causing sharp spikes of pain. The pain was nothing compared to when he began smacking my tits, alternative back and forth. Whatever illusion there was of a friendly search by this guard was gone as his hand left red marks on my breasts, and his fingers ravaged my dripping pussy.

“Listen to yourself?” Officer Cross scoffed incredulously. “You even sound like a mewing whore. I bet you didn’t even come here with a purpose. You just wanted your slut pussy to be used by big bad men, didn’t you? Didn’t you!”

“N-No, No–Oh fuck! Ahhhh! I’m c-cumming, I’m cumming!” I gasped as my thighs chattered together around the man’s hand as he continued to finger fuck me as the pulses of orgasms hummed through my body. “Oh my–Jesus Christ…”

Every muscle in my body went tense, and I held my breath as a splash of juices emptied from my pussy as I came. Men and women stood and looked in my direction as I stood naked before an audience. My body trembled and twitched for several seconds before I replaced control of my breathing, and my muscles stopped spasming.

Officer Cross grabbed a lock of my hair and pulled my head back so our eyes could meet. His square jaw hovered inches from mine.

“Did you like that?” he asked while his finger circleed my throbbing clip.

I tried to find my voice, but between my excessive panting and the roller coaster of pleasure rising and falling inside me, I could barely concentrate. “Oh God… Oh my God… Yes… I love it… Oh my God…”

I couldn’t focus. This wasn’t me. I had never been touched like that before in my life. I never had orgasmed like that before. It had been fifteen years since another man had made me cum and here I was now, naked, prostrate, and dripping wet in front of strangers while being fingered fucked. I knew this was wrong. I knew I was a bad girl for enjoying this treatment so much…

But why did it feel so Goddamn good?

Officer Cross moved behind me, and I heard the fumbling of a belt and the heavy clack as his duty belt fell to the ground. Realizing what was about to happen, my mind flashed to thinks about my husband, my career, my coworkers, brunch with my friends… God, they can never know I did this…

Officer Cross’ rough palm slid up my lower back to past my shoulders, grabbing the back of my neck roughly.

“Ahmmmm!” I winced at his tight grip and still felt a thrill of excitement in anticipation.

The tip of Officer Cross’ cock rubbed against my pussy lips briefly before I felt the building pressure grow as he entered me. The girth of his bulbous head filled me up and then began to stretch my pussy beyond its capacity.

“Oh, shit–fuck, fuck, fuck, fuck–Ow! Goddd…” I rambled as the guard’s huge cock split my pussy open. “I can’t–I can’t–I ca–Ughh fuck!”

Without warning, Officer Cross bucked his hips and speared his hard cock deep inside me. I throw my head back and screamed as the pain, pressure, and pleasure mixed together into something I didn’t know if I liked. The prison guard held me in place like I was one of his prisoners. A tight grip was on the back of my neck, and his other hand gripped a fistful of my love handle on my hip. Within seconds his cock was pumping in and out of pussy with an intensity I had only seen in porn but had never felt until now.

“Oh, fuck! Jesus Christ–Ugh, shit! Fuck, yes! Yes, fuck me!” I screamed as my mind warped, and I lost my place in the world.

“That’s right, ugh, take that fucking cock,” Officer Cross grunted between hard thrusts. “Fuck! Your cunt is tighter than any slut I ever fucked. Christ! I’m going to have to break you in.”

Both of the prison guard’s hands fell to my hips. His fingers dug into my thighs and ass painfully as he jerked me back with every hard thrust forward he made. The clapping sound grow louder as his body thumbed against mine.

“Yes! Yes! Yes!” I cried with every impact. “Fuck me! Fuck your slut! I’m–oh shit–I’m your filthy fucking slut!”

The words that I moaned with every thrust inside me sounded like they came from someone else’s mouth. Words that I would have never whispered before, I now screamed. Acts I couldn’t even fathom before, I nowretired in. My vision went in and out of focus as my world spun with growing pleasure, but I noticed more eyes watching me through the one-way mirror. Several people narrowed their vision at the glass as they grew suspicious.

“That’s it, stick that ass out like the whore that you are!” Officer Cross grunted. His fat cock slide more easily now in and out of my sopping wet cunt as I grew used to his enormous size, though I doubted I would be able to walk for the rest of the day.

Pleasure overtook pain as my screams crescendo. My pleasures were high pitch and desperate, filling the office and beckoning more people in the waiting room to look. They turned around in their seats to stare at the mirror–to stare at me–as I was fucked.

“Ohmygod-yeah! Yeah!” I cried as I felt something immense building inside me. My heavy tits clapped together and bounced back and forth with every rough buck of his hips. “Fuck me! Fuck your fucking whore–ugh god! I’m so fucking close–mmmm!”

The prison guard snatched a lock of my long blonde hair and wronged it back, briefly using it as a point of leverage as he thrusted inside me. With my head yanked back and my body assigned in a ‘U’ shape, my arms suddenly gave out, and I stumbled forward. The one-way mirror wobbled and bowed as my breasts were smoked against the cool glass. Officer Cross pressed the chef of my face into the glass as the wet thumbs of his cock penetrating me grow louder and the impacts harder.