Before Jeff and I had started this adventure, we both knew, even if we hadn’t said it out loud, that sooner or later, there would almost certainly be some breaking of character.  At day and at night, for the majority of the time, we could fantasize and pretend all we wanted that I was really in jail, and I might even be able to convince myself of it in my own mind.  But sooner or later, when we had sex, we were going to be boyfriend and girlfriend.

All the same, I wanted the first time we fucked here to be jailer and prisoner.

The more creative ways we could find to build or sexual encounters into our roles, the better and more fun it would be, and I’m sure we would.  But we weren’t professional actors and sooner or later, when we had sex, we were going to be boyfriend and girlfriend.

All the same, I wanted the first time we fucked here to be jailer and prisoner.

And I hoped, and really assumed, that Jeff felt the same way.

The previous day, when I had blown Jeff, he had promised that the next day he was going to fuck me.  I had nodded in agreement, excited, but part of me was wondering if that was Jeff my boyfriend talking or Jeff the police officer responsible for my incarceration.  Not that I was going to complain either way, but I was still left wondering what creative way he would find for our characters to fuck.

Then again, at this point, I was so fucking horny and just wanted him inside me so bad, I just wanted it to happen however he would make it happen.

At eight in the morning, he delivered me my breakfast, the same breakfast as the day before, without saying a word.  At lunchtime, he delivered my lunch in much the same way, this time stopping only long enough to tell me that he had reviewed my letter and that he found the content acceptable and he had mailed it out.

At this point, I figured out that he was using this as his last chance to truly make the anticipation build and he wanted to push me to my breaking point of desire.

Dinner came and again, he communicated very little.

Finally, at around eight-thirty, he stood outside of my cell door.

“On your feet, Inmate,” he said.  “Stand back from the bars.”

I did as I was told.  This was it.

He unlocked and entered the cell.

“I’ve been watching you, Brennan,” he said.  “And I was quite impressed with that blowjob you gave me, yesterday.”

I nodded, both excited but also somewhat nervous.  So much had built up to this.

“Perhaps you’d like to do a bit more.  Earn yourself some extra privileges around here.  Maybe a little extra exercise time.  Some cigarettes more regularly, get you some good magazines.”

“I’d…I’d like that, Officer Cooper,” I said.

He eyed me up and down.

“Of course, like I told you, nothing comes free here.  You’d…need to have some means of payment.”

“I…I think I understand,” I replied.  He backed me up against the wall and I smiled at him.  He smiled back and leaned in and kissed my lips with both passion and force.  I kissed back, putting my hands onto his shoulders.  His hands pressed to my chest and then he pulled my shirt up off over my head.

“Do…do I have permission to undo your shirt, Sir?” I asked.

He nodded and I unbuttoned his blue shirt.  He was still regularly wearing a police officer uniform for me and I ran my hand over the metal badge he had put on.  I let the shirt fall to the floor and ran my hands over his bare chest.

He pulled off my white undershirt, leaving me topless, exposing my breasts which he cupped in his strong hands.  His hands slid down my torso and tugged the waistband of the orange pants away from my waist which fell to my ankles leaving me in only my plain white panties.  I let my hands run over his waist.  My left hand found the handcuffs on his belt.

“You going to use these, again,” I asked him flirtatiously.

“I might,” he said simply, letting me know he was in control and the decision would be his and his alone.  His finger traced the outside of my pussy through the panties.  I was wet with over a week’s worth of anticipation having built up and we could both feel the moistness through my panties.  He grinned as he felt it and he tugged the panties away from my waist as well.  He led me over to the cot and in the process, I stepped out of the pants and panties which had fallen to my ankles and I was completely naked.

He laid me down on the cot and I looked up at him in anticipation, my breaths heavy, my chest rising and falling.  I spread my legs wide, inviting him.  I watched as he undid his belt and dropped his pants to the floor and then removed his briefs, letting out the cock which had been deepthroating me just the day before.

He knelt down on the cot, over me, his knees on either side of my waist.  Still waiting with anticipation, wanting him to make the first move, I kept my arms up on the pillow, my eyes unblinking, watching him.

“I’ve been wanting to fuck you ever since I brought you here, Inmate,” he said, lust in his voice.

“Y…yes, sir,” I replied.

He continued to look at my naked body, taking it in.  With one finger, he began tracing one of my breasts, making small circles, moving from the outer edge of my breast towards the inside.

“You got a boyfriend on the outside you’re missing,” he asked, seemingly trying to keep us both in character, in our roles, and I couldn’t love him more for it.  “Maybe a girlfriend?”

“I’ve got a boyfriend,” I said.  “He’s a wonderful man.  Waiting patiently for me to serve my time and get out.”  My breath was breaking and my voice was cracking as his finger continued to trace my breast, inching closer and closer to my nipple.

“I’ll bet he can’t wait,” he said.  “I’ll bet he jacks off every night thinking of you.  Especially with how good you look in that orange uniform.”

I grinned.

“If you continue to behave yourself,” he said, “maybe he can come and have a conjugal visit with you.”

My heart raced faster.  Always thinking, Jeff was already thinking of other ways to keep up our roles and keep it interesting for us.

“I’m sure he’d enjoy that,” I said.  “I know I would.”

“You don’t seem to have any qualms about fucking me, though,” he said.  His finger reached my tit but didn’t touch it.  He stopped short and began the process on the other breast.  My legs were wriggling, dying for his dick to slide into my cunt.

“You know,” he said, “this may be only a small city jail, but I still think you are a dangerous prisoner.”

“Oh, really,” I asked flirtatiously.

He reached down to his pants and then held up his handcuffs, dangling them off of one finger.  He took my hands and locked the cuffs around one wrist and then linked the chain around the bar of the bedframe above my head and then attached the other cuff to my other wrist, pinning my hands in place above me.

“Much better,” he said.  “Much safer.  For both of us.”

My eyes were begging him to fuck me.  I was on the verge of breaking character and begging him with words to just have his way with me.

As if reading my mind, he the head of his cock just inside of me.  I gasped, trying to catch my breath.  He slid it out, then slid it in, slightly deeper, the out again.  Behaving much the same as I had when I’d slid his cock into my mouth the day before, little by little, he increased how deep he went inside of me.

Then, without warning, he slid it all the way in, deep and hard and began thrusting himself against me.  My eyes wide, my mouth gaping open, my body in complete ecstasy and my hands unable to even grab him, my legs were like jelly, quivering.  My clit was white hot, every single nerve ending on fire.  It was almost like I was losing my virginity again.  I’d never experienced anything like this, never experienced any sexual encounter so intense and pleasuring.

My pussy was clenching around him and I wrapped my legs around his waist.  He was sweating, grunting, enjoying this every bit as much as I was.  He pressed his lips to mine and I felt one of his hands between our legs rubbing my clit.  I was moaning in absolute ecstasy.

I’d waited so long for this: avoided self-gratification and my body couldn’t hold it in any longer.  I screamed in complete bliss as I orgasmed squirting out from under his dick, soaking the sheets underneath us.

He wasn’t finished, though.  He’d practically told me he’d been jacking off thinking about me so he wasn’t as sex-deprived as I was so he still had some stamina left before he was going to fill me up with his seed.

“Oh, fuck!” I moaned loudly as he continued to thrust himself down on me.  “OH, FUCK!”

I was tugging at my wrists, wanting to wrap my arms around him, but he had applied the cuffs tightly so I simply kept tugging, rattling the metal cuffs against the metal bar of the bedframe.

“Fuck, that sound turns me on,” he grunted in my ear.

“Oh fuck, Je….Officer,” I said, catching myself from calling him by his first name.  “Please…don’t stop!”

I climaxed again and it was almost as large and as intense as the first one, again, squirting out.  I could feel my juices soaking the sheets, my ass pressed up against them.

Jeff let out an intense grunt as I felt him climax and I felt a river of his cum rush into me.  His thrusts slowed and when his orgasm had finished, he stopped and I felt him pull out and lay next to me on the bed while both of our breathings levelled off.

He looked over at me with a satisfied smile on his face.  His hand moved between my legs and with two fingers he penetrated my still-wet pussy and then brought his fingers to my lips which I suckled gratefully.

He stood up and pulled on his pants and then reached down and unlocked the cuffs from my wrists.

“Do you need a shower, Inmate?” he said.

Still numb and trying to process the intense pleasure I’d just experienced, I shook my head.

“Ummm…maybe later, Sir?” I mumbled.

He nodded.  He put his shirt on and buttoned it and exited the cell and I heard the door clang shut.