Training Officer, Part II: Work release

A BDSM Story by Harley Grant
© 2007 Harley Grant. Do not use without permission.

Chapter 1: Until we cuff again

After the amazing weekend together we had, I really would have been willing to go back immediately, but I knew it would be a bad idea for me to do so.  I had to let some time go by, had to let her know that this was too serious with too many consequences to get out of control.  But, I wanted it badly.

I saw her a few times over the next couple of weeks.  We’d exchange a wave.  She knew I was testing her resolve, and I wanted her to know that if she kept to her resolve that there would be rewards. 

It was hard on me to wait, but I had to; we had to know.

I called her up on Thursday of the third week after the end of our first session.  I know she wanted to suggest that I come over immediately, but she was as good as her word and suggested, hinted nothing.

“So,” I said, “I think it is time for a second session.  Would you agree?”

“Yes.”  Just that one word, how much it must of cost her just to say that.  But she was showing me how determined and disciplined she was.

“I’m glad.  I have a suggestion for what we could do next time.  It’s a little different than last time.”  Briefly I explained what I had in mind, it had been suggested by something I read in the newspaper.  She expressed interest, asked some questions and we negotiated the terms.

In line with the terms, I showed up at her house at 8pm on Sunday night.  I drove around to the back of her place.  I carried a little bag of clothes with me as I walked up to the house and rang the bell on the side door.  The door opened promptly and I found myself in a little ‘man-trap’, a little landing with doors ahead, behind and to the side.

I heard a voice from the door to the left, a door that led down the stairs to the basement.  “Remove your clothes and feed them through the slot.”  Indeed a slot had opened up at waist level.  In the confined space I had to work carefully, but, one article at a time, I stripped and pushed the clothes through the slot.

“Turn around, put your hands behind your back and back up to the slot.  I did, and I felt a pair of handcuffs being pushed through and secured around my wrists. 

“Hold still.”  I heard the slot closing behind me and another slot opening down at the bottom of the door.  Leg irons were secured around my ankles. 

“Remain still.”

I heard the door opening behind me.  A hood was draped over my head, so I could see nothing.

“Turn around.  There are stairs ahead of you.  Walk carefully; I will keep you from falling.”

I felt so dependent, walking blind down those stairs without arms to balance me.  And that was the point.  I went down the flight of stairs and we turned onto the floor of the basement.  I was led over to one side and she had me bend over at the waist and my neck was put into some sort of collar that prevented me from standing up.

“Stand by,” she said, unnecessarily. 

I heard her go back up stairs, get my bag, and lock the door behind her.  She returned and conducted a full cavity search, including my mouth after removing the hood.  She led me over to a low chair beside her desk.  She backed me into the chair and had me sit down.

It was one of those restraint chairs the prisons have with a recess in back so that cuffed prisoners can keep their cuffs on while sitting.  Soon a web of straps firmly locked me down into the chair so I could move almost nothing.  She sat down at her desk.

“It’s good to have you back.  I suppose a jailer should not say that, we do wish our charges to make a success of life, but still, we get attached.”

“It is good to be back, and I am really looking forward to the clarity of this week.”

She knew what I meant by ‘clarity’ and nodded.  “We shall begin.”  She stood up and, to my surprise, left the room and walked up the stairs.  She was gone for some time, leaving me strapped into the chair.

When she returned, she again sat down at her desk.  I could see she had some of my possessions with her.  She spent a little time arraigning them and putting them in plastic bags.  Finally she was ready to speak.

“So, you are on a work release program.  You will be allowed to leave the prison at 7:35am each morning.  You are required to return 5:30pm.  You must be back by 5:40 or punishment will ensue.  The only acceptable excuses for missing your return time are those beyond your control.  In other words, do not expect to go out for drinks after work or to work late.  If you will not be back by 5:40 you must call.

“I have inspected your wallet and personal effects.  Each morning you will be given your driver’s license, your medical benefits card and $20 in cash for lunch and other expenses.  All other items have been removed.  You must account for all expenses without exception.  I have placed a small tracking device in your car in a location that you will not be able to find; it allows me to monitor your movements to and from work.  You are only permitted to use the car for transportation to and from work.  Do not go home or to any other location.

“I have removed your car key from your key ring.  I will only give you your car key. You cannot access your home during your time in work release.  Do you have any questions?”

“No,” I said softly.  I was to be her prisoner even when I wasn’t physically in her control.  I began to become hard.

“Very well.  Because you will be out in the world, you will be exposed to influences that will undermine the spiritual benefits of your incarceration.  Thus, additional training must be imposed to correct that.  We will now begin the first example of this.”

She rose from her desk and placed a stool in front of me.  She sat on the stool and began to undo her belt and unzipped the top of her regulation trousers.  She stopped, fingering the black flashlight she held in one hand.

“This will be an exercise in understanding your inability to control or to dominate the situation.  Sexual symbolism will be used because of its profound impact on the male psyche.”

She shoved her free hand into her pants and began to masturbate herself in front of me.  She was, I knew, not very demonstrative when doing this, at least not initially.  I found this frustratingly erotic, which was the point, of course.  I wanted to fuck her, I wanted her to fuck me, but I was locked in the chair and could not move.  Slowly, I became rigid, but I could not masturbate myself either.  Which, I say again, was the point.

Once she loosened up and got wet, she pulled her pants and panties down and started using the butt of the flashlight against her clit.  She had a thing for police gear and a flashlight is nothing if not phallic.  As she was rising up to orgasm, she started penetrating herself with it, but clearly, the knurled surface felt good against her clit and she went back to rubbing until she spiraled up to climax.

She came down slowly and then stood and reclothed herself.  She took the end of the flashlight and gently touched my cock, causing me to groan.  She caught the tip of it between the flashlight and the chair and pushed until I started to feel pain.  Then she rubbed me again until I was groaning.  Abruptly she pulled back.

I looked up at her, I was out of control and she was in control, highly erotic to both of us.  After a charged moment of us looking into each other’s eyes, she started releasing me from the chair.

She got me stood up, hands still cuffed behind the back, and led me over to my cell.  I was put inside, the door locked, and then my hands released.

“Do not touch your cock.”  I obeyed, but it was difficult as my hands had instinctively gone towards there.

“Lie on the floor on your stomach.  Hands out above your head.”  Once I complied she ordered me to rub against the concrete floor.  I did so while she watched me and soon I came in shuddering spurts.

She silently handed me a paper towel, ordered me to clean up.  Once I had done so, she turned and walked back to her desk and I settled in on the bunk.

My cell was about seven feet deep and as wide, not a terribly confined space, although I knew she had punishment cells also.  The front of the cell was all open bars, allowing me to be monitored by her.  I noticed that a camera was hung from the ceiling with a good view of my cell.  That was new.

“You’ve noticed the camera.  It is monitored on my laptop which I will take upstairs with me.  I will be viewing you at various times during the night.  You are always under surveillance.”

With that, and a reminder that lights out was at 10pm, she went upstairs, leaving me to contemplate my cell and situation.

I guess I should wonder why I loved being in jail.  Why would anyone voluntarily agree to be confined, naked, used sexually and controlled for a week.  The key was that I trusted her and that we both knew that we were playing roles that required the best out of each of us.  So different from being abused by insecure, defensive Mistresses who cover their own weakness by a show of bravado.  Secondly, was that sense of clarity.  The bare cell, the absence of clothes, it pared things down, made them simpler.

Those thoughts took me from waking to sleep.

[ On to Chapter 2 ]