Caroline was 41, 11 years older than me, recently divorced from her first and only love, and HOT. She was hot but also the type who didn’t have any self confidence – until recently. She always wore boots and skirts, and always caught me looking at them in the office. I’m pretty sure that’s how she trapped me……
Caroline always kept spare footwear under her desk in the office, usually 1 or 2 pairs of boots. Not sure why, but most women store stuff like that there. Being a self confessed boot fetishist I wanted to see them up close, smell them, maybe even try them on. Caroline wasn’t big, just curvy for 5 ft 7. One day she wore a shiny black patent knee boot with 6 inch heels, zip down the back and had a pointed toe. And she left them under her desk after work, so I decided to stay late and see what they were like.
It was 45 minutes after everyone had gone home – so I was safe in the knowledge I wouldn’t be disturbed. I searched under her desk and the patent boots were the only ones there. They weren’t expensive. They were cheap plastic boots and even after only a few times of being worn they had a certain smell to them. The salty sweaty smell that makes the underside of your balls tingle. Another deep inhale and I was dizzy with excitement.
I decided to try them on at my desk. I held them again and could see my face in the plastic they were so shiny. I slipped off my shoes and drew up my trouser legs. I pushed my left foot into the first boot and squeezed it in. I had to stand on it with all my weight to get the foot in. The boot was 2 sizes too small and pinched my toes and the sides of my feet. I loved it. I had to tease the zip all the way up my calf to the top. The boot was tight and the heel was deadly high. The next boot was just the same – I was in heaven. Then the main door opened and in walked Caroline’s team, and Caroline.
Although I was out of sight I immediately swung my legs under my desk to hide the boots and my trousers rolled down over them. Their desks were on the other side so they couldn’t see me or know I was there. Now I rolled the trouser legs up again to get the zips undone. They wouldn’t budge. I pulled until I thought I would tear the metal from the runners. They didn’t move at all. They were locked on. I panicked. Then Caroline came over alone and smiling. The legs went back under the table.
“Evening !! How are my boots then ?”
I couldn’t speak.
“Cat got your tongue?” she teased. Then she whispered, “Do as I say if you want to keep your dirty little secret.”
I couldn’t argue.
Out of her bag she whipped out a set of zip ties in the form of handcuffs. “These are going on you now, or else I’ll call the others over for a look at you.”
I was frozen to the spot. She was grinning at me and all I could think about was how much lip gloss she was wearing. She had another pair of boots on and a long leather coat that looked great with hair brown bobbed hair. It looked like that was all she was wearing from where I was sitting frozen. Then I noticed my hands were cuffed behind my back and the zip ties were pulled tight. I was her prisoner. Then she smiled again and left me. Her colleagues hung around for a few minutes more then they all left. Caroline came back on her own a few more minutes afterwards. She swaggered across the office towards me. She stood me on my feet and unbuckled my belt, then undid my trousers. As we both had heels on I was 3 inches taller than her. Then she took my trousers and boxers off over the locked on boots that were pinching nicely, not that I was noticing.
I was standing there with just my shirt on, a semi and a pair of ladies kinky boots with my hands trapped behind me. She pulled down her thong and placed it over my head so that the crotch of it covered my nose. It was warm and smelled divine. My balls tingled again and she saw my member twitch. She laughed out loud and then told me she had some work for me to do whilst she went shopping. It was near Christmas and late night shopping common.
She opened my drawer, opened my wallet and took my credit card. “Tell me the number, or live to regret it. But if you do give me the right number I guarantee you’ll be glad of it.” I gave her the number foolishly. She raised my chair as high as it could go and sat me down on it linking another zip tie from my hands to the back of the chair. The chair was so high now I couldn’t touch the floor whilst seated. She then produced some notes from her bag and told me to type these up for her before she got back from shopping. Then she put some very RED lipstick on my lips. She then opened Word on my PC but noticed I couldn’t reach the keys without some help. She spotted my large oversized metallic pen on my desk and crouched down opening her legs as she went. She then took my pen and inserted it in her anus. She pouted as it went inside her, the dirty bitch.
It came out without any trace of brown but was noticeably unclean. She placed the dirty end in my mouth and told me to type all the notes up using the pen. If I drop the pen or piss her off in any way she would blow my secret to the world and I would never EVER live it down. At this point I took stock of my situation. I was naked except for a while shirt with the sleeves rolled up, knee high patent boots that were locked on and starting to ache, zip tie hand cuffs behind my back that were locked to a chair, a thong over my head with the best part over the nostrils, very RED lipstick and a large pen that tasted of arse protruding from my mouth.
Off she went and I sat there for a while testing my bonds, but not having the nerve to drop the pen yet. I was stuck and couldn’t free myself because my feet couldn’t touch the floor. After 5 minutes I came to the conclusion that I was stuck and that I’d better start typing. It was slow going but I finished after 45 mins. I sat there still and cold with my erection long gone and a taste in my mouth I couldn’t get rid of. I tried moving the pen to a more comfortable position but ended up dropping it. I swore just as the doors opened and in strode Caroline. She had numerous bags but the bag that stood out the most was the Anne Summers bag, the local filth shop. She was beaming now, but when she saw the pen on the floor she gave me a look that worried me.
Out of the bag she produced a paddle, a riding crop, a long cat of nine tails, a dog collar and chain, a double ended strap on (oh yeah), a butt plug and some minty lube. She also had a bag from the local costume shop that I was intrigued/concerned about. Without words she cut my shirt from me with some office scissors and cut the zip tie connecting my hands to the chair. I asked for a drink because of the strange taste in my mouth.
She replied “Thirsty? I can solve that for you”
The collar went round my neck and she locked it with a padlock and the chain hung from the collar, the cold steel brushing my chest. At this point she sat on my desk and undid her coat revealing nothing but boots, bra and flesh. She then pulled my chain until I stood up and she pulled again until I started to bend towards her. I couldn’t move my legs closer as they were blocked by the edge of the desk. I just kept bending. She then hooked her booted legs round my neck and drew me towards her gleaming moist clit. It was clean shaven and my tongue rolled out in anticipation. I drank from her with all my might. I was so horny at this point, from fear and restraints that I blanked everything out except the focus of pleasuring my new mistress. I pleasured her for about 5 to 10 minutes whilst she moaned and groaned and thrust her thighs into my face. I felt her shudder and heard a gasp, and then she relaxed slightly. I teased her with my tongue and she moaned again.
Her heels moved onto my shoulder and she forced me up with the point of the heel. It hurt more than it should but I wanted it to. She laughed when she saw my face. It looked like I had an accident with the lip gloss my face and chin were so shiny. I was smiling though, and she had an evil look in her eye again. I found out why sooner than I hoped.
She moved the bags around out of my view until finally she produced a maid’s costume. She opened it out and told me to step in. I wasn’t really in the mood or position for a fight so I obliged her. She lifted it to my waist and then I heard the sound of Velcro. It was a theatre’s maid’s costume that sealed at the top of the dress by Velcro. I was now in a maids costume with boots, thong on my head, collar and chain, and zip tie cuffs behind me feeling rather vulnerable. She was in boots, bra and a leather coat that fell to just above her knees.
She bent me over a small round conference table and gave my arse a thwack with the paddle. I yelped and begged her not so hard. She stroked my cheeks with her hand and then scratched them with her purple painted nails. That was heaven so I moaned to show my appreciation. I hear some shuffling about which resulted in her moving towards my head which was hanging over the edge of the table. She was wearing the strap on.
“Give me a blow job you slut” she taunted, and shoved the cock in my face.
I did what I thought was a good job, sucking the rubber cock like I would want it my self. She wasn’t impressed and used the riding crop on my cheeks from the angle that she was. It hurt, and got worse.
“Please” I begged
“Do it like you mean it. I want to believe it !!”
After some more whipping I started to go nuts on it in the hope it would stop the strokes. It worked as they got fewer and further between. I was exhausted and she moved away. We looked at the cock which was now dripping with saliva.
“Perhaps we don’t need lube after all” she announced.
She pressed the cock hard against my anus and it hurt as it wasn’t properly lubricated. I squirmed and struggled and she finally conceded that lube was needed. A few seconds later my hands were hoisted high in the air and held there by her left hand. Her right hand grabbed my right cheek and then she lined the cock against my anus and pushed slightly, almost teasing the cock home. It still hurt slightly and I pushed back on her arms but she was strong and then thwack again, she had paddled me. I jumped from the surprise and the cock crept further in. The minty lube gave me a cold burn inside. Now the girth had stretched me it was easer getting the length inside. Once in I felt violated and giddy again from the excitement. I groaned pleasure again and she paddled me once more, and started thrusting in and out. I was totally powerless which made it feel even better. I was being fucked like the slut I always wanted to be by the woman I had always wanted. It was heaven and hell, and would be for quite some time yet.
She stopped thrusting and commanded me to do the thrusting. I pushed back and forth but was encouraged by her paddle and nails on my cheeks.
“Tell me you love being fucked in the arse. Tell me you are a slut for cock” she said.
I started saying her words, but the pain kept coming and it was getting worse. So I got louder and faster, and she was moaning her delight too. The minty lube was giving me cold heat on my ring and was starting to feel sore. Some last encouragement from her, some violent thrusting from me and she came again !! I was dripping with sweat and needed some rest. I wasn’t going to get any.
She sat me on my chair again, then sat on my knees with her clit facing my cock. The strap on had been discarded. She placed her arms around my neck and placed her mouth close to mine, imitating that she wanted to give me a sexy snog. I held me tongue out wanting hers but she hovered just out of reach teasing me. I so wanted to kiss her. I wanted her to know I would love and worship her, and not let her down like her husband before. She lingered longer and then her fingers crept into my mouth,
She moved them in and out and I sucked them and loved them. She moved herself next to my throbbing cock and started rubbing her clit with it. She perched herself up and her vagina lingered over my cock, teasing me again.
“Please” I begged again.
“Are you worthy?” she asked
“I am yours forever” I tried
“You will be” she stated.
She teased some more and I stretched myself to get my cock closer or actually inside her. She had all the power and I couldn’t satisfy myself. I was powerless and I never did get inside her then. I would have sold my soul to be inside her. She stood me up for the next part of her game.
She hooked the chain of my collar on to a coat hook which was attached to a pillar in the office. I couldn’t bend my knees without choking now so I was forced to stand up straight. There was only 1 garment hanging from the coat hooks. My bosses raincoat. My boss is an ugly fat bitch who hates men. Caroline shoved me close against the pillar, and with 2 bulldog clips fastened my dress up at the front and the back so my cock and arse were showing. Next she placed my cock in my bosses raincoat and sandwiched the cocked between myself and the pillar. Then she told me to masturbate myself until I come. This was difficult with my hands tied behind my back.
I started rubbing slowly. I couldn’t bend my knees, so my tip toes were the only things I could use to get the motion going. My feet were hurting now but it’s the kind of discomfort you long for. She applied some more lipstick on me and told me I was going to serve her for a long time. It sounded like a great idea as she inserted the minty butt plug in my arse. It was a big one and stayed firm as my arse closed around it.
She picked up the cat of nine tails and swung it at my cheeks. It stung and I shuddered, but I kept going and it spurred me on. Every 10 or 15 seconds she whipped me and I yelped with pain every time. She made me talk dirty again, claiming my love for cock and looking like a slut. I was to continue this until I came, which seemed like a life time away at that moment. Still the whip stung my cheeks and still I talked like a slut until finally I started coming inside my bosses pocket. At this point Caroline takes the butt plug from my arse which aides my coming further. Thwack. Thwack and another 2 strokes finish me off. I’m spent and my knees and legs are trembling with exhaustion and cramp. I’m a mess.
Caroline unhooks me from the coat rack and I sit myself down on my chair. I can hardly breath let alone stand. Caroline is holding the butt plug which wasn’t as clean as the pen she used earlier. She moves closer and holds my balls in her right hand and offers the dirty butt plug to my mouth with her other hand.
“Open wide and clean it!” she commanded
My mouth stays firmly shut. She squeezes my balls with ever increasing pressure until finally it’s too much and I open my mouth. In it goes and all I can taste is foul minty mess.
“It has to be spotless, so you better do a proper job of cleaning it.” She warns me.
I have to suck it as she slowly pulls it from my mouth. When it came out it’s clean but the inside of my mouth isn’t, and I want to be sick. She understood and offered me some of the water on my desk. I swilled it about my mouth and spat it into an empty cup stack on my desk. I thanked her for that, as it was disgusting.
“That was fantastic!” I blurted out, and was about to tell her which bits I enjoyed and which bits I didn’t when she shut me up by slapping my limp cock with the riding crop. It was enough to shut me up.
“I’m not really interested that you enjoyed it or hated it. I’m only looking out for me”. Thinking about what she said back then makes perfect sense now, but at the time it just shut me up and made me feel self conscious.
She got down on her knees and took my boots off. This was done with a small pin inserted into the side of the zip. It must’ve been a trick zip, and I’d fallen for it. The boots were off and my feet tingled as the blood came back into them. She scooped up all the toys that we played with and put them in the Anne Summers bag. Next she took off the maid’s outfit and put it back in its bag. The collar was unlocked and also went in the bags. She took the thong off my head and stuffed it into my mouth, then stuffed my ripped up shirt in her bags. Now I couldn’t talk if I wanted to and I was naked apart from the zip tie handcuffs.
“I’m keeping your credit card for the weekend. I deserve a treat for putting up with your disobedience. Now come with me. We are nearly finished for tonight”, she says as she scoops up her bags, my clothes too and my bosses coat.
I followed her into the landing area where the lifts are situated. She stops me and zip ties my legs together at the ankles. She enters the lift and orders me to remain where I am.
“These scissors will be downstairs by reception. Your exit badge, wallet and car keys will be there too. Your clothes I’m keeping for now. If you need something to wear home then this coat should do you. I’ll leave it in the bin OUTSIDE the office.” She then pulled the thong from my mouth.
With that done the lift door closed and I knew I had to go outside naked if I wanted to get the coat. I waited until the lift returned and hopped in. Pressed the “G” with my hands behind me and hopped out when it reached the ground. I hopped over to the scissors and my possessions and managed to snip myself free of the bonds. Now naked I peeked outside. Nobody was within 50 ft of the doors and Caroline had vanished. I chanced it outside naked and heard a wolf whistle on the other side of the large courtyard. I ignored it and grabbed the coat from the bin, put in on and ran to my car in the multi-storey car park.
The drive home was uneventful if you discount me screaming out loud in utter disbelief at what just happened. I got home and sneaked into the house. It was dark outside so it aided my escape. My girlfriend and I weren’t serious so I was living on my own at that time. I drew a hot bath, had a soak and a play, then took myself to bed and slept soundly dreaming of my new mistress the entire night. It was heaven, but also one of the last ever nights I would sleep in a house alone.
I would love to get feedback from you as I hope continue the story, please give me your thoughts and suggestions - iamacdtom@googlemail.com
05.03.10
story continues in Sweet Caroline 2: More Caroline
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