Is this Business or pleasure?

Is this Business or pleasure?

       

I’ve no idea why I agreed to go along with the girls in work. They got me into the mess this weekend or did they? Maybe I have only myself to blame!

To se the scene:

It was November 2004 and to celebrate one of the best years in the history of the company I worked for, we were going to have the party to end all parties. That was only half the story. The other half was that this mega party was to be a fancy-dress party and I agreed to let the girls in the office sort out my fancy dress outfit.  That was my first mistake!

It was now Friday and the day of the big party. I’d worried about what was in store for me for the past eight weeks since I’d agreed to go through with the whole dress-up thing.  I’m by nature, a very reserved, late thirties guy; heading up a team of around forty high tech call-centre staff; thirty-five of who are female and in their mid to late twenties. I think most of those girls were permanently on heat! I had gone out with them all on a few occasions but just to bars in the Glasgow area but never a company bash and never a fancy-dress.

So, back to Friday afternoon:

“So David, are you ready for the big night,” asked Kelly, one of the team leaders in my group of high-tech misfits.

“To be honest Kelly, I’m now a little worried about tonight and what you girls have in store for me but hey, I’m part of the team so I’ll go along with whatever you suggest,” I replied?

When it came down to it, I had no idea what they had in store but I agreed to their little plan and I was not one to break a promised! It was decided that Kelly and one of her team, Sonya would come around to my apartment at six-thirty and help me prepare myself for the big event. I guess they both knew that I’d probably not agree to what they had in store if I actually knew their plans but hey, I was a guy of the world so I’d take whatever they’d throw at me. As pre-arranged, we closed down early this afternoon and we all headed home at four to get ready for the big night.

My apartment was on the river, a few miles west of the city centre so I hadn’t long to wait once I got home so a few bottles of Bud and a hot bath, I was ready for whatever the girls had in store.  I half wanted Kelly to get round sooner because I have to tell you that I had a secret crush on this gorgeous blonde that had led my team of misfits for the past two years. I had my own set of rules since my divorce three years earlier that I would NEVER have a relationship or sex to that matter with any girl in the company.  Some-one once told me that, ‘you should never screw the crew.’

Anyway, I hadn’t long to wait because at six-fifteen the buzzer went and I saw Kelly and Sonya at the front door wearing what could only be described as school uniforms. As I pressed the button to let them both in, I had a lump in the pit of my stomach as I now half guessed what these two had in store for me tonight.

I opened the door to my apartment just as the two girls skipped out of the lift (elevator), with a wicked smile on their faces.

“Good evening David are you ready to join us tonight,” both girls burst out in tandem?

They dashed into my apartment and headed straight towards my kitchen and the bottle of white wine I’d promised would be waiting for them both. I think both Kelly and Sonya were in school-girl mode, never mind the school-girl dress. Sonya wore a St. Trinion’s pinafore with sheer black stockings. I could easily tell they were stockings because of the suspender belt could be seen below the hem of her pinafore, attached the tops of each stocking. Kelly wore a slightly more modern uniform with a very short skirt (black), white blouse, which was opened at the neck in a scruffy manor with a school tie loosely tied around her neck. Her black bra could easily be seen beneath the white blouse and her legs were clad in thick Black (opaque) Lycra tights (pantyhose). She also wore a wool cardigan and as she entered the kitchen she pulled it off along with the long school scarf that was previously wound around her neck.

“You two look fantastic tonight, so what am I to wear then girls,” I asked, half knowing already what they were about to say?

Kelly began as I closed the door behind them both:

“Well David, the entire team are going to the party as school-girls and so are you,” she explained!

“What Kelly, even the other five guys,” I asked?

“No David, they’re wimps and are not going tonight. When they heard what we were doing, they accepted to work the evening shift,” she replied.

As the two girls pored their glasses of wine, I opened my third Bud and told them to do their worst and while I wasn’t too enthusiastic about dressing as a girl tonight, I would go along with there plan but there was no way I was going to shave anything!

“Don’t worry David,” explained Sonya, “You’ll not to shave a thing as we’re organised tonight to transform you into a slightly plump but we’re sure, terrific school-girl.”

Anyway, my third Bud down, it was time to get dressed and Kelly started to empty the contents of the plastic bag she’d brought with her. I’d given Kelly a hundred Quid (£100 pounds) to get the attire she had in mind and I’m sure she had spent the money well.

“Okay David, go into your bedroom and slip into this panty girdle. It will be tight but I promise you, it will be worth it,” explained Kelly as she handed me what seemed like a very thick and elastic pair of BIG PANTS.

I took the package and headed for my bedroom. I undressed from my male cloths and started to step into these new pants and boy they were tight! I’d never worn female cloths before and while I understood the need for these pants to be tight, I had enormous trouble pulling them over my slightly plump stomach. Once pulled up they felt bloody uncomfortable but after quick glance in the mirror, I knew exactly why Kelly had bought them. My upper thighs and bum were now a completely different shape and my stomach was now pulled in quite a bit. It wasn’t flat but hey, the result did it for me!

Once back in the living-room, both girls cheered as I entered. Kelly then told me to approach as she held up a black padded bra.

“This should fit just fine David,” as she turned me around and slipped each arms into the straps and buckled the strap at the back.

This bra already had silicon implants built in and did a fantastic job of providing me with a ready made cleavage.

“Right David,” said Sonya. “We didn’t expect you to shave your legs so we’ve bought you a pair of the thickest black tights we could find.  They’re completely opaque and at 90-denier, they should hide your leg hairs and give you a great pair of legs. They’re also maternity tights so the top should be extra tight and help pull in you tummy even more.”

With a little instruction from both girls, who had now polished off the entire bottle of wine, I slid my legs into the very soft black clingy material. I told Kelly to go and open another bottle of wine as I helped myself to the white blouse and short PE skirt that once on, left the thick tights to hide any of my indignity. The school tie was next and once finished I guessed I looked a tad like Kelly.

“Right David, to your face now,” explained Sonya as Kelly came back into the room with two full glasses of wine and fourth Bud for me.

I then set down and let Sonya loose with her make-up. I have to say that it felt terrible! I hated the feeling of make-up as Sonya seemed to slap it on thick, very thick.  This process took the longest and once finished, Kelly produced a long blonde wig. Before she placed it on my head, Sonya placed a latex cap on my head, puling back my short hair into the tight cap that clung to my head. The wig then attached using Velcro to hold it in place and Kelly pulled the blond wig into pig-tails to match the one’s she wore in her hair. Two pink bows finished the attire and I was told to go and see myself in the mirror.  To be honest, I didn’t recognise the person that stared back at me in the mirror:

“You two have done a brilliant job, don’t recognise myself here, well done,” I applauded the team.

“Right David, call a taxi,” requested Kelly as she handed me the last three items, a pair of over-sized girls shoes, a wool school blazer and a long wool school scarf.

I sat down to strap the shoes on to my ankles. Thank goodness, they had low heels but I made my second mistake of the night by letting Sonya kneel down decide me and padlock the straps, ensuring the heels stayed on.

“What the fuck Sonya,” I demanded?

“Well David, these ensure that you can’t take the shoes off until we say so. We’re expected to wear painful shoes so tonight you’re going to understand what girls have to go through,” responded Sonya.

I guess I had no option as I stood up, gained my balance on the low heels and slipped into the wool blazer. To finish my outfit off, I wrapped the long school scarf around my neck, leaving the two ends draped across my over-sized chest, bulging through the tight blazer.

“Right, we’re off,” explained Kelly as she threw a hand-bag to me and told me to put my house-keys into it!

By the time we got to the taxi, accepted the whistles and abuse from the driver, my feet were killing me already. How was I going to get through the night?

The whistles and abuse from the taxi driver was only the first of the night as we walked from the car all of 100 meters to the hotel and the venue for our company party. The whistles continued as we went inside and I joined the rest of the school-girls, sorry the rest of my team of misfits, all wearing various versions of girls school-uniforms.

The Party itself:

The evening was a success, a massive success! There must have been over three hundred people in the grand ball-room of the Glasgow Hilton. Everyone, both staff and special customers had all made a massive effort this evening and no-one had wimped out of the fancy-dress theme.

As the meal finished, the dancing began and I joined both my team and several customers on the dance floor for the many hits of the 80’s that set the tone for this evening. After-all, the 1980’s was the era for most of us, except a select few of the younger members of my team would remember. Hits from Howard Jones, The Thomson Twins, Ultravox, Human League or Erasure, that brought back many memories of an easier time of life. The drink (alcohol) also made us all a little more receptive to the dancing and approaches from many of the guys from the office. Everyone was impressed at my nerve of going as I was but everyone complemented me also. In fact, I even won the best-dressed guy award. The best-dressed girl award went to Jennifer Owens; a senior director in a fairly boring government department who came tonight as a police woman but no ordinarily police woman! She wore a very revealing short skirt and white shirt with various badges alluding to some made up American police department. The police uniform came complete with a thick leather belt holding fast the implements of her work like the genuine American S&W police handcuffs that took my fancy (mistake number 3).

As the winners of the best-dressed male and female of the evening, both Jennifer and I had the pleasure of a slow dance, in front of al our colleagues and clients. As we paraded around the dance floor, Jennifer whispered into my ear:

“I was hoping to bump into you tonight David,” she explained.

The alcohol was certainly taking over as I made my response:

“I’m also glad to bump into you tonight Jennifer. You look fantastic in that uniform and those handcuffs look so inviting,” I blurted.

I would have never let down my guard without alcohol tonight and certainly got given one of my best clients the idea that I was into bondage, which of course, I was.

“So David would you like me to arrest you,” asked Jennifer in an extremely alluring voice?

“Not quite yet Jennifer but defiantly later,” I replied as Culture Club finished another one of the mid eighties hits.

That was only the beginning of my third mistake to lead Jennifer on. For the rest of the evening we seemed joined at the hip, we sat on one of the comfy settees in the corner of the grand ball-room and chatted as long lost friends and not as the typical supplier / client relationship we’d had for the past five to six years. Yes, Jennifer was an extremely attractive lady. In her very early forties, she had looked after herself. She still had a great figure but then tonight she was looking particularly good in her police uniform. This was a pleasant change from the formal power-dressing business suits she normally wore when we met once a month in her government department. Her long auburn hair cascaded across her shoulders and rested just below the collar of her white police shirt. It was clear we had rather a lot in common.  Like me, Jennifer was divorced or should I say, waiting on the paperwork from the local sheriff court that would dissolve a tiresome and lacklustre marriage that started in her early twenties. She was certainly a beautiful woman and we certainly got on very well this evening but maybe that was the alcohol talking. This growing friendship was getting off to such a great start, I forgot that I was dressed in the girls school uniform and looking very out of place from my normal grey business suit worn during our monthly account management meetings.

As the night ran on into the early hours of Saturday morning both Kelly and Sonya joined us. Both had worked this account very well over the past year and Jennifer complemented us all on how good a team we were in managing her account way beyond anything that our competition were capable of.

Kelly then produced the keys that kept my feet firmly locked in the leather strapped shoes that had torn my poor feet to shreds for the past five-and-a0half hours.

“You deserve these back David. You’ve handled tonight very well and the rest of the team are so happy to have a boss as daring and cheerful as you,” She complemented as popped the keys into my handbag and kissed me on the lips.

“So David,” asked Jennifer, “are you ready for another dance?

“No problem Jennifer but first, can I have the next dance with Kelly,” I asked in the manor I would have asked a school teacher.

Kelly and I then danced a slow number from Dire Straights and towards the end, Jennifer and Sonya joined in. Little did I know they had a devious plan, which meant they both grabbed my arms and in only a few seconds had both wrists locked into Jennifer’s handcuffs behind my back. I did my best to ignore the fact I was now restrained and tried to act as cool as possible as both Kelly and Sonya both kissed me on the face, remarking on their lip-stick marks being left behind. It was then Jennifer’s turn but the kiss on the face ended up as a kiss on the lips and there was no doubt that her tongue was in my mouth. I had no control and funny enough both Kelly and Sonya didn’t seem that surprised by Jennifer’s advance. We al continued to dance, which was not too easy for me in these bloody shoes and my arms secured behind my back in Jennifer’s handcuffs. Soon the set ended and we headed back to our settee. Once there I ask Jennifer to remove the handcuffs but Kelly thought they should stay on and she produced a straw to ensure I was able to drink my G&T. We sat on until the crowd started to leave and the room began to look rather empty.

“David, should I call a taxi,” asked Kelly?

“No problem Kelly. I would do it for you but I’m a little tied up right now,” I responded.

Kelly then asked Jennifer where she lived and I said we should all get a cab together and I would get out last and pay. The taxi now booked and on its way, the girls all started to put on their coats and wrapped their school scarves around their necks, in anticipation of going out into the cold November air.

“Okay Jennifer, you’ve had your fun. Can I please have my hands back so that I can put on my blazer,” I asked in a slightly frustrated voice?

Before Jennifer even had time to answer, Kelly cut me off and suggested that it would fun to keep me cuffed for a little longer. Slightly pissed off, I stood up and allowed Jennifer to drape the blazer over my shoulders and wrapped the long wool school scarf around my neck. She tied it off a wee bit too tight but as I said earlier, I love bondage and to be honest, I was enjoying the attention of the girls.

The Journey Home:

Sonya was first to be dropped off and then next to Kelly’s apartment on the south-side. I was disappointed when she got out oft the taxi and kissed me good-night. I had hoped that Kelly would have advanced more but then I had my rules and she probably had hers, which didn’t involve sleeping with as colleague.

It was then back towards Dunbreck and the expensive part of the south-side where Jennifer lived. The taxi pulled up outside a large stone house and Jennifer said, “We’re here.”

“Okay Jennifer, can you release my arms now, please,” I begged.

She started to rummage through her hand-bag but after what seemed like ages but only a few minutes I’m sure, she announced that she couldn’t find the keys. I wasn’t happy as my third big mistake of the night now meant I had to go into a client’s house. Come to think about it, I had no rules bout clients, only colleagues. Jennifer was a great looking girl and I was currently handcuffed with no keys.  What choice did I have?

Jennifer then paid the taxi driver, he said, “Good luck” to me as we got out of the cab and headed towards Jennifer’s large stone built house in this very exclusive part of Glasgow.

The Weekend Starts

“I’m so sorry about the keys David, I was sure I’d put them into this hand-bag,” explained Jennifer as she unlocked the front door and I followed her in.

Her house was lovely and while still her marital home, her husband had left her for another woman so currently she still had access to this wonderful and very large house.

“Go into the living-room David while I go and find the keys,” asked Jennifer as she directed me into the living-room and help me down onto the large leather couch.

It was difficult sitting down with my hands cuffed behind my back but Jennifer helped me until she lost her balance and collapsed on top of me. I’m not sure this was planned but very quickly our lips locked again but this time the kiss was much more passionate than the last on back in the Hilton. Jennifer then regained some composure and removed the heavy wool blazer, which had practically fallen off my shoulders, trapping my poor cuffed hands even more.

Jennifer then straddled me sitting on the couch and we kissed for the next twenty minutes or so.

“Do you want to take this further David,” asked Jennifer?

“Do I have a choice Jennifer,” I responded?

“Well you do David but I think you quite like me being in control,” purred Jennifer in an extremely sexy voice, teasing me even more.

She was right and told me that she was about to try something I might enjoy.  I’ll not say that this was now another mistake of mine tonight since my third big mistake and the handcuffs started the slippery slope that I now found my self in.

Still straddling me, Jennifer untied the scarf that was around my neck and folded the soft wool into a thick band, before winding it twice around my face, cutting off all light.  The scarf was now an externally effective blindfold that covered both my eyes and nose. It still allowed Jennifer to kiss me again before helping me on to my feet. Holding on to my arm, she led me totally blind through her house.  I heard the key unlock another door and I followed her downstairs. We walked across a carpeted area before stopping on what felt like a tiled floor.

“Hold on a second David, I’m going to unlock your hands now,” explained Jennifer in a business like voice.

As the handcuffs came off both wrists, Jennifer told me that I could remove the scarf myself.  As I did this, I heard a loud CLUNK of a heavy door closing and as soon as I blinked to regain some focus, I realised that I was now in a small jail-cell looking back out at Jennifer through bars of thick steel.

“What the fuck is this all about Jennifer,” I demanded?

“Well David, this is my play-room and I would like you to stay here for the rest of the weekend and enjoy it with me,” she explained.

Again I asked Jennifer if I had a choice and she once explained that I could leave if I really wanted but why not explore her fantasy world. I stood there for a few minutes, staring through the cell bars at this beautiful woman who until only an hour ago was a client of mine. I’ve idea if this weekend was now going to be business or pleasure?

“Well okay Jennifer,” I responded. “I can handle this situation but I have to say that I am not into pain, is that clear?

Jennifer just looked back at me and promised that this would be a weekend to remember and one that I wouldn’t want to forget. I was then told to get some sleep and she would be back in the morning when the fun would begin.

“You’re not going to leave me in here all night Jennifer,” I shouted as she left the downstairs basement, on route for the stairs leading back up to the house.

“David, you love it, I know. Just enjoy yourself in there and I’ll be back in the morning,” she replied.

I then settled down for the night in this prison cell.  It was warm and I had a wash-hand-basin, toilet and a bed, which felt fairly comfortable. I then began to remove the school uniform and clean my face from the horrible make-up that had been stuck to me for the past seven hours. I had nothing else to wear in bed so I climbed into the bunk after taking a well earned piss. There was no light switch in the cell but it was only another ten minute until it went out anyway and I was left to myself, locked in this cell in Jennifer’s basement.

As I said, it was warm and comfortable in Jennifer’s basement prison cell. After I got over the initial shock that I was locked in a tiny prison cell, under the house of one of my best clients. This was probably a sick fantasy of mine built how did Jennifer actually know. Soon after several hard-on’s, which I resisted to take through to conclusion, I finally fell asleep. Unfortunately, morning came far too fast and I was awoken by a rattle on the bars of my jail cell.

“Good morning sleepy head, its gone half-past-ten and it’s time to get up,” explained this incredibly sexy voice, which I failed to focus on as my eyes strained to get into the correct gear.

Finally the vision of beauty came into focus as my eyes finally cleared themselves and standing just the other side of the cell bars was Jennifer, dressed in a bright red leather catsuit covering her entire body except for her head.

“Do you like what you see this morning David,” asked Jennifer but even before I got a chance to answer: “I can see you do,” she responded on my behalf.

I had forgotten that I’d jumped into bed with nothing on last night and what Jennifer could see now, couldn’t hide my reaction to her awesome choice of attire this morning.

“Okay David, I’ll unlock the cell door and let you go and take a hot shower. The basement has its own bathroom and I’ve also left you some Gillette and a razor, not to mention a toothbrush, toothpaste and some deodorant,” explained this red godess standing just outside my jail cell.

She unlocked the cell and let me slip out into the basement. I stopped and touched the luxurious leather that encased her body.

“You look gorgeous this morning Jennifer,” I complemented before we kissed for the first time this morning.

Jennifer then pointed me towards the basement bathroom and I left her to prepare myself for the day ahead, whatever it had in store. As I exited the bathroom after about twenty minutes of washing, shaving and some other stuff, Jennifer stood waiting, with a pair of handcuffs in her right hand. These were probably the same handcuffs that allowed mistake number three last night and what got me into this unbelievable situation. Without any prompting, I turned around but Jennifer explained that she was going to cuff my hands in-front this morning. Surprised as I was, I lifted both hands in-front of me and allowed Jennifer to cuff them. What I hadn’t notice before in the middle of the basement was a chain handing from the ceiling, which the end was soon padlocked to the chain connecting my two cuffs. Using a remote control the chain retracted slowly into the ceiling taking my arms with it. I was soon standing high, with my arms stretched out above me, well and truly trapped, enabling Jennifer to do whatever she wanted.

“Right David, I loved you in the school uniform last night but I’ve got some other ideas for today so please allow me to get you dressed. Please don’t resist because even though you might not like pain, I will not hesitate to  whip your ass. Just enjoy the experience because I know you like wearing girl’s cloths from your reaction to the fancy-dress part night.”

With that I stood there and allowed Jennifer to first take out a wet sponge and wipe it all around my budging man-hood, causing my best friend to retreat immediately, which enabled her to grab and lump of steel and start placing it around my groin. I knew exactly what this was but my protests fell on death ears and she slid my dick into the sheave that forced him now between my legs. As Jennifer pulled the rest of the belt around my hips, I could see the full horror of the steel chastity belt that now meant pissing standing up would be impossible but more importantly, sex and masturbation would also now be impossible.

“Now David, if you serve me well this weekend, I will reward you by allowing you to cum on Sunday night but only if you’re a good boy and do exactly what I say,” explained Jennifer as she pushed home the two ends of my steel penis prison with an mind deafening sound, “CLICK!”

That job done, Jennifer began placing an evil looking black leather corset around my torso and begin lacing it up. Fuck it as tight but everytime I told Jennifer, she pulled even harder on the laces until I stood there, hardly being able to breathe but as I looked at myself in the mirror six feet away on the far wall, my figure was looking even better than last night.  The body shaper had done a good job but this thick leather and boned corset had reduced my slightly over-weight mans physique into a slightly over-weight hour-glass woman’s figure. The corset had built in boobs and boy they were large, much larger than the implants within the bra I wore last night. Next, Jennifer produced a pair of black stockings. These were nearly opaque and black to match the corset. Jennifer explained that they should hide my leg-hairs and while she would have shaved my legs, she did respect my wishes and these opaque stockings would just have to do. I lifted each leg under direction from Jennifer and she slowly pulled up each stocking and attached them to the suspended belt, hanging free from the leather corset. Next came a pair of very high-healed boots, leather boots. Jennifer slid my stocking’d feet into each boot, zipped them up and them padlocked the zip closed, ensuring these boots were staying on my legs until Jennifer decided they were coming off.

“Jennifer, I’m not sure I’ll be much use to you in these heels,” I remarked.

“Don’t worry David, you’ll be an expert by the end of the day,” replied Jennifer as she collected her next item, a strange looking plastic head.

“What the fuck is that,” I asked?

“Don’t be so rood David,” replied Jennifer. “This is a very expensive female mask made from the finest Latex. You should be able to wear this all day. It will allow you to eat, drink, kiss but most importantly serve my needs this weekend when I require those services from you.”

With that I was instructed to lower my head to enable Jennifer to slip the rubber mask over my head. It was tight, very tight and with some tugging and pulling, vision finally returned to me via the two eye holes. My mouth fitted around the moulded mouth built into the mask and holes were even provided where my nostrils were so I guess Jennifer was right, I could wear this mask for ages, without too much stress. As I watched the goings-on in the far mirror, Jennifer came round behind me and started closing the mask using the built in zipped on the back of the mask. My facial transformation was nearly complete now Jennifer picked up the long blonde wig that was held tight on my head via the Velcro strips that covered the zip.

“Nearly done David, only one more item before I release you,” explained Jennifer as she returned with a band of thick steel.

“This will ensure the mask stays on David,” explained Jennifer as she held the thick steel collar in front of my eyes. On it was inscribed, ‘property of Mistress Jennifer.’

A chill ran down my spine as Jennifer closed the tight band of steel around my new neck and once again the CLICK told me that this fucking mask was staying on as long as Jennifer wanted it to.

True to Jennifer’s word, she then picked up her remote control and lowered the pulley from the ceiling, which meant my hands lowed too. Soon I was free of the chain and then the handcuffs.

“I’ll go and prepare breakfast David,” explained Jennifer. “I’ve left a dress for you to wear in cell, go in and put it on please?”

I did as I was told but as soon as I walked into the cell, Jennifer slammed the barred door behind me, locking me in once more.

“I’ll be back in fifteen minutes to get you David, I can’t wait to see you in the dress,” said Jennifer as she left the basement on her way back upstairs.

I forgot for a few minutes that I was once again locked in the jail cell in Jennifer’s basement, the same jail cell I spent all of last night. The dress was my next objective but first I couldn’t help staring at the refection in the mirror on the cell wall above the sink. Yes, I looked a little like a slightly over-weight Barbie doll but I was certainly not David anymore. The Latex mask removed David’s face and replaced it with a stranger’s face, a mask that took away any sign of my male inside. The tight leather corset and attached stockings were also not the type of underwear that a guy would wear so any sign of the real David had gone. I liked what Jennifer had turned me into but could I really handle what she had in store for me today?

So to the dress: -

It was a simple dress, a jumper dress as we call them in the UK or maybe a jersey dress or sweater dress. Whatever you want to call it, the dress was a long, black and white striped, long sleeved pullover with a thick roll down neck that would cover me in warm wool or wool like material. I’ve no idea if it was wool or not? Not the most sexy dress, baring in mind what I was now wearing under it but certainly the only dress that Jennifer had left me to put on. I picked up the bundle of wool and slipped it over my head and pulled the dress down over my body and smoothed it out. The dress came to just below my knees, which meant that all I could see was the leather boots sticking out below the wool. When I looked in the mirror, I’d no idea who was looking back at me! I knew it was me but it wasn’t as this female face was staring back with a very expressionless, plastic looking face with a long head of blonde hair cascading down to just below my shoulders.

Just at that point, Jennifer returned to the basement and stood in front on my cell bars:

“Fuck me David, you look great. Much better than I’d expected you’d turn out!”

I guess this was the only complement I was going to get this morning but I’d no idea how to take it. How did I get myself into this situation?

In Jennifer’s right hand was a thick black leather belt:

“David, can you buckle this around your wait please and slide the D-Ring to the front and the buckle to the back,” asked Jennifer as she handed the leather belt through the bars of my cell?

I immediately knew that this would now mean the dress was staying on, just like the mask and the chastity belt that meant no fun until Jennifer said so! Once the belt was on, Jennifer handed me a pair of handcuffs and asked me to lock one wrist into a cuff, then pass the free cuff through the D-ring on the belt and then lock the free cuff around my other wrist. The only good thing at this new round of restraint was that these handcuffs had a longer chain than normal between the cuffs. At least two feet of chain would allow some freedom but not nearly as much as I wanted.

Once I was secured to Jennifer’s satisfaction, she opened the cell door and approached taking hold of my waist and landing her lips on my plastic face. While I couldn’t really feel a lot, I returned her passion and our tongues soon met. Pushing me back towards the bunk, I fell without too much effort from Jennifer and soon she was on top of me and we kissed for quite some time. She felt good on top of me. Even though my wrists were trapped in the handcuffs, attached to the thick leather belt, I was able to give Jennifer some reassurance that I was enjoying myself, even if I was now this freak in a dress.

I soon realised that I could gain more reach but only with one hand by sacrificing the reach of the other hand. I was therefore able to grab the crotch zip on Jennifer leather cat suit and quickly found that she had no knickers on as I trust my fingers into her wet crack. She moaned as the pleasure built and soon she was on her side kissing me more vigorously as I used my cuffed hands to deliver pleasure to my leather clad captor. She was very horny this morning and it didn’t take long to make her explode! We continued kissing for a few more minutes and she thanked me for satisfying her already and told me that so far as I being a good boy and exceeding her expectations for me today. It was now time for breakfast and once we straightened each other up, we headed upstairs to the main house and the kitchen where Jennifer had already set the table in preparation. It was only as I started to walk out of the cell and up the stairs that I realised the true picture of my situation. I’d no experience of wearing high heels and these boots meant progress was going to be painfully slow today. I couldn’t really use my arms as balance due to the simple fact they were attached the leather belt and movement wasn’t going to be easy. This was also the same situation at breakfast. I could use one hand to eat with but it was a painfully slow process and one that Jennifer enjoyed watching.

“Your enjoying watching my misery this morning Jennifer, aren’t you,” I asked her across the breakfast table?

“Are you really that miserable this morning David,” asked Jennifer?

“I think frustrated is more the correct feeling Jennifer,” I responded. “While these cuffs are driving me nuts, the chastity belt is more an annoying because while satisfying you this morning was enjoyed, I’m desperate for release myself.

Jennifer went on to tell me how much she was enjoying me struggling to do the simplest things like eat with my hands restrained but the fact that I was dressed the way I was, with the female face mask made her so horny.

“Would you like me to relieve you again Jennifer,” I asked?

“You are keen to please me

David, much more than I expected you would behave,” she responded.

Jennifer then instructed me to go back downstairs and wait in the cell for her, which I did immediately. Like walking upstairs to the kitchen was difficult, the return to the basement was equally difficult wearing these fucking high-heel boots.

As instructed, I sat on my bunk in the tiny cell. I guess I was fairly fee because the barred door was still open but not for long as Jennifer returned to the basement and the first thing she did was slam the door closed, locking it as well. Jennifer had taken the opportunity to change while she was upstairs. She was now wearing a black leather teddy, attached to black sheer stockings, which disappeared into long black leather boots. I was then instructed to lift my hands to the bars to enable Jennifer to unlock the cuffs, followed by the leather belt that was buckled so tightly around my waist. Next she asked me to remove the black and white striped dress, leaving me in the black leather corset, stockings and long high-heeled leather boots myself. I still think Jennifer was a much better looking female than I could ever be, even with the tight corset and female mask! Next she held up a pair of standard handcuffs and asked me to turn around so she could lock my arms behind my back. As soon as she was satisfied that I secure again, the cell was unlocked and she entered.

“You look great David, really good in that outfit. I want to take you up to my bedroom but before I do, I want to get this gag on you,” explained Jennifer as she held up another leather strap with a rubber / plastic attachment in the middle.

Without any argument, I allowed Jennifer to place the gag into my mouth and strap up the leather buckle at the back of my head. A quiet CLICK meant that it was now not coming off until Jennifer used a key. I then followed her upstairs to the main part of the house and then up some more stairs to the first floor and into her bedroom. There was nothing that special about her bedroom except the bed was clearly a supper-king-size with steel frame foot and headboard.

“Lie down please David,” instructed Jennifer.

I tried to mouth how difficult it was with my hands cuffed behind my back but Jennifer didn’t listen as she climbed on to the bed beside me. The next thing she produced was a massive black dildo, which slotted into the mouth piece locked around my head. I now had an enormous cock sticking out from my female face mask and Jennifer soon held me down and positioned herself over the humongous penis. It took a few seconds but soon she was sliding herself up and down on my face. I could smell her juices as they began to flow around the plastic cock sliding in and out, faster and faster! Jennifer began moaning more and more, louder and louder until she exploded and then calmed down immediately as she lifted herself off the dildo attached to my gag.

“That was fucking wonderful David, thanks,” said Jennifer as she removed the dildo from my gag but leaving me lying on my back, hands cuffed behind and wondering what was going one!

Fuck did I want release but I couldn’t help even myself for the two simple facts that my hands were cuffed behind my back and the steel chastity belt was still lucked around waist, cutting off any access to my man-hood.

Before long, Jennifer returned from the bathroom after cleaning herself up and led me back down to the basement cell. I struggled as Jennifer led me by the arm and pushed me back into the tiny room, closing and locking the barred door before I’d time to recover and make any escape attempt.

“Thank you David, that’s was wonderful but I have to go out now for a while. I’ll be back in a wee while so don’t go away,” explained Jennifer as she left the basement and me, locked in the cell still handcuffed and gagged.

I tried to scream at her but the gag allowed very little sound to leave my mouth and it was in0vain as the gorgeous girl that invited me back to her house last night and who now was my jailor, was now in complete control of my weekend.

I was so horny as I sat on the bunk, locked in the tiny cell with my hands cuffed behind my back and my mouth packed full with the gag and still wearing the same leather corset, stockings, leather boots and latex female mask that I’d been wearing from before breakfast. Even if I could reach my cock, I had no access to him through the layer of steel that allowed no access. It was therefore like being locked in two prisons. The large prison for myself and the smaller prison built especially for my penis!

Saturday therefore wasn’t turning into a good day! I had nothing to do but sit there and await Jennifer’s return. On a normal Saturday I would have spent the day catching up of TV programmes that I’d recorded on Sky+ from the previous week or caught up on my personal e-mails, not to mention surf the world-wide-web. Instead, I was locked is this tiny cell in Jennifer’s basement. Oh, why, why, why hadn’t I ignored her last night and not gone back to her place? On a similar note, why had I let the girls con me into dressing up as that slutty school-girl? If I had not let them do that to me, I probably wouldn’t be in the situation right now. Don’t get me wrong, it was a fantasy of mine to be imprisoned by a beautiful girl and here I was, locked in Jennifer’s basement cell. But where was she? I’m here alone and badly needing to take a piss, not to mention my jaw was beginning to hurt from several hours of being packed full of the leather gag. Certainly there was a toilet in the cell and I was no longer wearing the sweater-dress. I would probably have to get used to pissing with the chastity belt on so what was different except my hands were cuffed behind my back. I therefore went over to the toilet, sat down and let the pressure take its course, pushing my piss out under enormous pressure. Sure I was relieved but how would I clean the residual mess that had now built up around the chastity belt?

AS I struggled with the toilet-roll using my cuffed hands I finally heard the sound of Jennifer returning to the basement. She stood in front of the barred door and laughed at my disposition:

“So you little slut; you needed to take a piss and now you can’t clean yourself,” she taunted.

All I could do was mumph from behind the gag that packed my mouth. Jennifer then suggested I go over to her and turn around so that she could unlock the handcuffs. That achieve I was then able to clean as best I could around the steel belt that imprisoned my man-hood.

Jennifer was gone again but now I had a chance to explore the belt that imprisoned what I so much wanted to play with! The chastity belt gave me a smooth groin and hid the budge that would normally give away any idea of my man-hood.  Fuck this was frustrating and was turning me on so, so much. I could gain no access to relieve my urge and every way I tried, made me even hornier! To be honest, I’d nearly forgotten about the gag that kept me quiet but like everything else, it was firmly locked in place and even with the use of my hands, I had no access to remove it. Now my hands were free, I could cover myself again. Yes, I’m sure I looked okay in the tight langrage but the black and white, stripped sweaterdress lay in a bundle at the foot of the bunk. I therefore slid it over my head and smoothed the soft wool over my new silky smooth curves. Just as I admired my self in the mirror, Jennifer returned wearing a black leather min-dress and knee high leather boots.

“So you thought you could dress yourself,” she taunted again.

She also laughed at my attempts to respond through the tight leather gag. I grabbed at it but it wouldn’t budge, which caused Jennifer great delight at my misery.

“Okay David, take the sweaterdress off and slip this on instead,” demanded Jennifer as she passed a bundle of black satin material through the bars!  “If you do as I ask David, then I’ll remove your gag but if you mess me around, then you can keep it on until bedtime!”

I didn’t wait to find out what Jennifer had given me to wear this time as I was keen to impress and get rid of the fucking gag! Soon I was standing in front of Jennifer wearing my underwear again. I handed the sweaterdress through the bars to Jennifer and then started to prepare to slip on whatever it was she had passed through the bars this time.

It was clear on further investigation that Jennifer had handed me a black satin maid’s uniform. It was made of very thick black, shiny material but as I was about to slip it over my head Jennifer said no and pointed to the zip at the back. How weird I thought but I soon realised that the neck was a tight frilly affair and I’d never have gotten over my head if it hadn’t been for the zip. It was only then that I noticed that I would have to step into this dress. While it had a medium length skirt, the dress had a built in bodice that meant it wasn’t coming off without the use of the zip. I could see Jennifer was tiring quickly so I stepped into the maid’s dress, pulled it over my corseted figure. It was only as I slipped my arms into the sleeves did I notice the major difference in this dress. Put simply, my arms didn’t appear out of the sleeves! Instead I stood looking at two leather straps hanging down where my hands should have been and it was then I realised this was a weird fucking straightjacket. A straightjacket made to look like an English Maid’s Dress.

I knew that I had no other option but to turn with my back to the bars so that Jennifer could pull up the zip, which see did immediately. She then started to button up the dress at the back before handing me a set of leg-irons to me and ordering me to lock one around an ankle and the other end around a leg of the cell bunk. She was certainly taking no chances in me escaping. Jennifer needed into the cell to finish strapping me into the straightjacket/dress.

As soon as me arms were folded in front and strapped from behind, Jennifer stood back and took a good look at me:

“You look great David but I’ve one thing to change before I unlock your gag,” she explained as she fiddled at the back of my neck until the steel collar was uncloaked and pulled from the mass of satin that covered my neck. I thought that I was about to be rid of the tight collar but not for long as Jennifer secured it even more tightly around the high neck of the maid’s dress.

“Ah that looks better,” said Jennifer as she stood back to admire the new me, this time wearing a black maid’s dress.

All I could do was mumph in reply until Jennifer took pity on me and asked me to turn around so that she could unlock the gag. It was such a relief as she pulled it from me mouth.

“Ah, that’s so much better, thanks Jennifer,” I said as I tried to get used to the feeling of freedom around my mouth.

It was only after Jennifer replied, “You’re welcome,” did she approach and lock her lips on to my female masked lips and our tongues entwined themselves passionately for at least a few minutes.

“David, you have no idea how fantastic this weekend has been for me so far and I hope you will be my guest until tomorrow,” asked Jennifer?

“I feel that I’ve no option but to stay Jennifer,” I replied. “I’ve been locked up, handcuffed, gagged and wearing these female cloths all day, not to mention the frustration of having my man-hood imprisoned in the steel belt. What choice do I really have Jennifer but to stay with you, especially as you now have me locked into this ridiculous maids dress or straight jack?”

“I guess you’re right David but if you are that unhappy, I’ll release you right now and you can go home,” she responded.

“Jennifer,” I started a response in a low voice. “I’m actually enjoying myself except I have to say that the gag was really sore. I’d be happy to stay here with you but I’m bored of being locked up in this cell all day. I’ve satisfied you several times today so how about us going upstairs and you satisfying me?

Jennifer just smiled and explained that if I stayed until tomorrow (Sunday), then she would release me from all my bondage at lunch time and we could spend the afternoon in bed before going out for a meal in the evening. I agreed and she kissed me again.

“How about we go up to the living-room David and watch a movie,” asked Jennifer.

I thought that was a great idea so she unlocked the leg-cuff currently attached the cell bunk and attached it around my free ankle, now hobbling me with a 19” chain between the leg-irons. That complete I followed her upstairs and we sat together on the couch and watched a film. Yes, I still restrained in this dress and wearing female underwear, not forgetting the bloody steel chastity belt that refused to allow my man-hood to rise to anything like the size he was attempting to every few minutes. I was as horny as hell and I loved what Jennifer was doing to me but fuck did I just want to take her upstairs and give her, a good seeing to!

“Jennifer, I’m hungry sweetheart, how about some dinner,” I asked?

“Sure thing David,” responded Jennifer. “How about I order in some Indian food?”

I was happy with Jennifer’s suggestion as I loved Indian food but I had the nagging questions about how I was going to eat with my arms strapped in the straightjacket/dress. There was no doubt that Jennifer would come up with a solution. She then picked up a menu from the kitchen before I agreed what I wanted and then Jennifer made here selection. She then called the local take-away and placed our order. The food should then be here in an hour.

“Jennifer, how am I going to eat with my arms straight in this way,” I asked turning to Jennifer and demonstrating the tightness of the straightjacket/dress.

“I’ll agree to releasing you from the dress and allowing you some lose bondage by simply cuffing your hands in front of you if you promise to be good,” outlined Jennifer.

I agreed to Jennifer’s terms but taking no changes she led me back down to the cell and soon as the barred door was locked, she released the straps and unbuttoned all the buttons. Before pulling down the zip, she unlocked my steel collar and removed the leg-irons. As you can imagine, this was quite a long process with Jennifer having to stretch her arms through the bars to undo all the various restraints, which finally allowed me to step out oft the straightjacket/dress and hand it back through the bars to Jennifer.

“I’ll be back in a minute David,” explained Jennifer. “I have the perfect dress for you to swear this evening,” and she headed over to the basement wardrobe and return with a leather dress.

I was handed the dress through the bars and told to simply pull down the zip and put the dress on like a shirt before pulling the zip back up. The front zip started at the base of the lined leather skirt and ended just above my chest. The neck was therefore open and showed off the steel slave collar that held the female mask firmly in place. I was then instructed to put the leg-irons around both my ankles again and put my hands through the bars to enable Jennifer to lock the handcuffs in place. That job completed the cell door was once again unlocked and I was fairly free to hobble back upstairs behind Jennifer.

“Have you ever spent time in the cell Jennifer,” I questioned?

“Not in a very long time David,” she replied. “My ex-husband would sometimes lock me in there but I’ve always tended to be the dominant one and therefore I love having a man locked in there, at my beck-and-call.”

She then told me that she’d had several boyfriends since her divorce three years ago but she had never found them to be made of the right stuff (her words), to introduce them to her playroom.

“So what made me, the right stuff,” I asked?

“I had always thought you had potential David, when we met for business meetings but any guy that let’s his staff dress him in a girls school uniform, makes them more interesting and therefore the potential I look for in a guy,” she replied.

“I guess that I have always had a kinky steak in me Jennifer,” I explained. “I’ve always loved bondage but I fall in neither the top or the bottom camp. Don’t get me wrong, I love what we’ve done this weekend but I’d love to return the fun to you one day and make you my slave for the weekend.”

It was clear Jennifer wasn’t making any promises to enable me to tie her up in a hurray so I accepted my current position as her slave and waited with her in the kitchen until the Chinese food arrived. During dinner we discussed my previous attempts at mixing cross-dressing with bondage and how I really quite enjoyed wearing the various female attire that had been forced upon me this weekend. Jennifer told me that she had new ideas for tomorrow morning and I reiterated my wish to be free no later than lunch time!

“While I think about it Jennifer, do I have to spend tonight in the cell,” I asked?

“David, I’ve already told you,” replied Jennifer. “You will be free tomorrow but until then, you will remain in my personal custody and therefore until tomorrow, you will spend time in the cell! How else do you think I can keep you under my control?

“Am I not in your control now,” I asked Jennifer, holding up my cuffed wrists in her direction?

“To be honest David, the fact that I can’t be bothered to feed you myself, I would have either cuffed those hands behind your back or simply left you in the straightjacket/dress. You’ve been extremely compliant so far and I trust you to not take advantage of your relative freedom,” she replied.

We continued to chat in the living-room over coffee and we also kissed many times through Saturday evening. By now, I’d nearly forgotten about the female mask that had hidden my male identity since early this morning. At around 11 o’clock, Jennifer suggested it was bed time and led me back downstairs. Before I was pushed into the cell, Jennifer unlocked the slave collar and removed the wig, followed by the female mask, what a relief! The salve collar was then place around my bare neck and locked once more. I was then directed into the cell where Jennifer handed me keys to unlock my own handcuffs and leg-irons. She then left me to undress myself.

I have to say undressing myself was easier said than done! I had to remove the leather dress, followed by the boots, stockings and finally the most difficult part, the corset. After what seemed like some time, I was as bare as the day I was born, except for the steel chastity belt. After washing, I climbed into my small prison cell bunk. After half-an-hour or so, Jennifer returned, wearing only a night shirt.

Standing in front of the bars, “David, cuff your hands to the bar on the bunk above your head please, I’m coming in,” instructed Jennifer!

Doing exactly as I was told, I picked up the handcuffs, which were lying on the neat pile of cloths and cuffed them above my head to the bar that made up the head of the tiny prison bunk.

Unlocking the cell door, Jennifer entered and we kissed for the next ten or fifteen minutes. Jennifer rubbed her hands all over my body and kept pushing hard against the steel belt that trapped m aching dick! Suddenly and without any reason, she got up, left the cell and locked the barred door behind her.

“Good night sweetheart, see you in the morning,” and with than she was gone!

I was so stunned; I forgot that she had left me there, still handcuffed to the bunk. ‘Fuck,’ I thought to my self! I way going to have to spend the night cuffed to the bed, unless I could reach the keys, which were also lying on the pile of cloths, or so I thought. In Jennifer’s sudden exit, I hadn’t noticed her taking the cloths with her, leaving me locked in the cell and handcuffed to the bunk. It was therefore going to be a long night. I must have been tired because I didn’t lie there very long until sleep finally over-took my consciousness.

Morning therefore came with daylight coming through the slatted windows on the basement. A need to take a piss soon followed but no way for me to even leave my bunk. I had no option but to lie there and accept my fate. The more I lay there, the hornier I got and therefore the more I needed to take a piss! A circle of need with no means of escape until Jennifer arrived to unlock me.

I guess I lay there in desperation for over and hour until finally Jennifer arrived in the basement, still wearing her nightshirt.

“Jennifer, I badly need to take a piss, can you please unlock these cuffs,” I pleaded?

She just laughed at me but thank God, she entered the cell and unlocked my hands.

“I’m going to leave the cell door open David. Have a piss and take a shower. I’ll be back down in twenty minutes to see you,” she explained.

Doing as I was told, I was washed and ready for Jennifer by the time she retuned to the basement with an evil looking suit in her arms.

“David, until lunchtime, I want you to wear this suit,” explained Jennifer as she handed me the evil looking heavy rubber.

Fuck was this bad!

Jennifer had handed me an extremely heavy rubber suit that would cover my entire body from head to foot. The legs had built in high heels and the head was really a built-in gas mask with two thick, opaque lenses with a muzzle filter covering the nose and mouth. The hands didn’t seem to have any fingers, instead simple round balls, where four fingers and a thumb should have been.

As soon as I had pulled both my legs into the legs of the rubber suit, I needed help from Jennifer. My arms slid into the very tight rubber arms but once my hands made it into the tight balls at the end of each arm, I had lost the use of my fingers. Jennifer then helped my remaining arm into the suit and started to pull the body up and over my torso. She then removed the steel collar telling me that she had no use for it now before pulling my head into the built-in gas mask. I started to breathe heavily as she started puling up the zip, which finished at the top of my head. I didn’t hear any CLICK but certainly felt Jennifer locking the zip. I felt the lock was pointless now that I had no use of my hands anyway.

Just as I thought she had finished, she produced a set of medieval manacles on some extremely heavy chain. I was ordered to kneel as she locked my wrists into the heavy irons behind my back, followed by my ankles, which were attached to my wrists with not nearly enough chain to allow me to stand up. Jennifer then ordered me to follow her out of the cell and into the open basement. This movement could only be described as a shuffle on my knees, which was not a quick comfortable never mind quick way to move around. Never-the-less I did mange to follow Jennifer around the corner to where she had a sofa and a table covered by a white table-cloth. By now, I was beginning to sweat! The rubber was thick and heavy and had no way to enable my skin to breathe at all! The gas-mask did enable to breathe but I must have sounded strange from the outside as it certainly did from inside the suit. Only then did I realise that my morning was about to get much worse!

Jennifer removed the white table-cloth from what I though was a table. In front of me was now a small cage and it was obvious I was about to spend some time inside it!

I shuck my head and called out through the gas mask:

“No Jennifer, please not in there!”

It was no use as this gorgeous girl with an evil streak just grabbed my rubber body and pushed me down to the ground, forcing me forward and into the tiny cage. The cage door then slammed closed with a bang and I had no option but to lie on my side in the loose hogtie caused by the manacle set that attached my wrist to my ankles behind my back.

“See you later darling, enjoy your morning,” shouted Jennifer as she left the basement.

I don’t think I would have heard her unless she shouted at me. The rubber suit was very thick and I think the hood had padding around the ears. All I could here was my own breathing through the regulator of the built in gasmask. I had only been wearing the suit for 15 or 20 minutes and already I was far too hot. I could feel my skin starting to perspire so god knows how I was going to survive the rest of the morning in this fucking thing?

I was also so hungry! I hadn’t eaten since last night’s Indian and you know how long it is before you’re starving after a Chinese meal? My arms were beginning to get sore in their position attached to my ankles, behind my back. I did try to get comfortable in the tiny cage but to be honest; there wasn’t space to reposition my restrained rubber body. I lay there what seemed like hours and probably was hours. Jennifer never returned once to check on me and the heat was unbearable! The thick runner suit caused my whole body to perspire all morning so I’ve no idea how I could possible stay hydrated until lunch time. My arms were killing me! Even though the hogtie was fairly loose, I struggle against the strain of the lack of distance between my wrists and ankles and trying to reposition my rubber clad body caused even more energy, which just seemed to be converted into more sweat.  Finally after a long time I saw the faint glimmer of hope as Jennifer came through the basement door. She was dress in her gym gear. A tight red leotard, over tight butt hugging Lycra shorts.

“How are feeling David,” she asked?

“How the fuck, do you think I feel Jenn? I’ve been imprisoned in this fucking cage for hours. My arms are killing me! I can hardly breathe through this fucking gasmask and I’m sweating like a pig in this suit. You’ve had your fun so please let me out of here,” I ranted!

“You don’t have to be so rood David,” replied Jennifer in a very stern voice. “I will not tolerate such ignorance so enjoy the rest of your Sunday afternoon and with that she left.

Oh fuck, what had I done? I suppose I did deserve what had just happened but there was no way I could take another ten minutes in this suit, never mind another couple of hours. I had therefore received my first real punishment at the hands of Jennifer. I had no option but to continue my Sunday afternoon in pain and even discomfort. I was hungry, tired and felt absolutely miserable by the time Jennifer returned.

This time she was wearing a tight pair of blue jeans, black polar neck sweater and black leather boots. Fuck did she look good!

“How are you feeling now, my dear,” Jennifer asked as she knelt down in-front of the cage where I lay on my side.

“I feel terrible thanks Jennifer,” I responded in a low voice from behind the gasmask. “I’m really sorry for being so rood to you early, please forgive m, I asked in my pleading voice?

“That’s better David, time to let you out.”

Thank God, I thought to my self as Jennifer unlocked the cage door and hauled my restrained rubber body out an onto the basement carpet.

My ankles cuffs were first, followed by my wrist cuffs. At least some freedom from hours locked in the same position. Finally I felt some cool air from behind as Jennifer unzipped the rubber suit from the top of the built-in gasmask, to the base of my spine. For the next five or ten minutes we struggled to remove my sweating body from the tight mass of rubber. Once complete, Jennifer offered me a glass of water before suggesting I take a hot shower.

The shower was excellent! I used the jet of hot water to caress my aching limbs from hours of torture in the heavy rubber suit. My dick was still locked in the steel chastity belt but I knew for not much longer. Jennifer returned to the basement as I was drying myself off. With the towel tied around my waist, she handcuffed my wrist in-front and asked me to follow her up to her bedroom. This had been the first time she had taken me to her bedroom. It was large modern looking room with a king-size bed with chrome head and foot board. Soon I was lying on my back with the gorgeous Jennifer on top. It didn’t take her very long to secure my already cuffed wrists to the head-board, using another pair of handcuffs.  Using another two sets of leg-irons, my ankles were now spread eagle to opposite sides of the foot board, leaving me in a very vulnerable position. Next Jennifer approached with a key and after removing the towel that was still tied around my waist; she had full and uninterrupted access to the chastity belt that had imprisoned my cock since yesterday morning. Fuck, it felt god to be free of the belt. Jennifer now removed her boots, jeans and sweater revealing a black silk bra, suspender belt and silk stockings but no knickers. My cock jumper to life and she slid on top.

We made love for the next hour or so. It was the best sex I’d had in years! Jennifer was obviously an excellent lover or the simple fact of having me locked up at her beck-and-call all weekend was a frustrating for her as it was for me locked up and under her control. After Jennifer returned from cleaning my juices from her sex, we talked for a while. I had no option but to lie there with Jennifer on her side next to me. We talked about he weekend and how much she enjoyed having me.

I was keen to understand was this a one off weekend or was there a longer term offer on the table? Jennifer assured me that she had no intention of this been a one-off fling.

“Okay David, I guess it is time to go over to your place and get you some cloths so we can go out tonight,” explained Jennifer.

I had forgotten that I’d arrived at Jennifer’s in the school uniform on Friday night.

“Jennifer, do I have to put that uniform on again,” I asked?

“Yes, dummy, if you want to get home, she replied!

Before Jennifer started to pick up the school uniform I wore to her place on Friday, she started fashioning the chastity belt around my waist.

“No fucking way Jennifer,” I shouted. “I’ve been in that fucking thing all weekend and there is no way I’m wearing it again!”

“Relax David,” replied Jennifer. “If you’re a good boy tonight, I’ll give you the key later.

Some how I didn’t believe her so I bucked against my bonds with no success. The handcuffs and leg-irons kept me tight against the bed in a very vulnerable spread-eagle position. It therefore didn’t take Jennifer long to have my man-hood tucked away and secure in his own private prison once again.

“There you go David, not a lot you can do about it now,” explained Jennifer in an evil voice. “Calm down and I’ll release you. Continue like that and I’ll be forced to take action!

I suppose I knew by then that I’d no option but to relax and accept what Jennifer had just done. Within minutes, I was free of all bonds and getting dressed again in the school uniform that had got me into all this trouble in the first place. The body-shaper slipped on easily over the chastity belt. With some help from Jennifer, I was into the bra followed by the laborious job of sliding into the thick black opaque Lycra tights. Not long after, I was finished but slightly apprehensive about leaving Jennifer’s place wearing this get-up. On Friday, I was drunk so it was easy to persuade me to appear in the uniform.

Jennifer then came up with an excellent idea:

“David, why don’t you wear the female mask and that will hide your face completely. I’m sure you’ll feel much more comfortable going out with the mask on.”

Even with the female mask in place, along with the long blonde wig, I wrapped the scarf around my neck, pulled on the blazer and followed Jennifer out to her Mercedes, parked in the driveway.

It only took ten minutes to arrive in the parking area adjacent to my apartment block. This was the most worrying bit of the journey. The walk from Jennifer’s car to the apartment building, followed by the lift to the top floor and my apartment. It was November and dark outside so with a brisk pace, I was into the building and awaiting the arrival of the elevator. Great, no one in the lift so Jennifer and I got in and selected the sixth floor. The lift seemed slower than usual but soon the doors slid open and we exited. Even better, no-one up here either so I took my keys out of the handbag and entered the apartment. I breathed in relief as I’d made it unseen by any of my neighbours.

I headed for the bedroom to chance into some male cloths for dinner. I thought about asking for the keys to the belt again but I thought better of it, hoping that Jennifer would honour her deal later.

Dinner was a very civilised affair. Two normal people out on a Sunday evening in Glasgow, enjoying each others company.  Nothing exciting to report! Jennifer drove back to my apartment and came up for a coffee. We kissed more but hoping for some more relief from a mad weekend of passion didn’t materialise. At around ten-thirty Jennifer handed me a key to the chastity belt and left. We agreed to see each other again next weekend.

As soon as she had gone, I headed straight for the bedroom and removed my cloths. Taking the key, I slid it into the tiny lock on the belt. I slid in so far but wouldn’t fit properly. I was in despair trying to release the fucking belt but it wouldn’t budge. I called Jennifer’s mobile (cell-phone) but continued to get her voice-mail. I had no home phone number for her so I’d no option but to wait until tomorrow and call her at work. Yet again, she had one over on me and I was in effect, still Jennifer’s prisoner.

The End.

Ed Kilpatrick

EdKBound@GMail.com