A Little Extra Insurance

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I invite my boss to spank me.
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tony090909
tony090909
1,498 Followers

The start of this story is set in the 1970s, i.e. before email etc

* * * * * * * * *

"You've got to help me Diane. You're my sister, if you won't help me no one else will."

There was a wild, desperate edge to Mark's voice and I bit my lip in concern. He was five years younger than me and I'd always kept an eye out for him. At first it had just been childish scrapes, but as a teenager he'd developed a careless and selfish streak which drove our parents mad.

There had been a steady trickle of incidents where he'd come to me for help. Usually it was for money, but this was more serious. I work at a firm of insurance brokers and had got a quote for the motorbike Mark wanted.

The purchase and all the other details were supposed to be sorted out next week, but Mark had rung me late on Friday afternoon. He'd bought the bike, taken it out for a first spin and crashed it. The police were involved and he'd lied and said he had insurance. He had to produce a cover note within the next seven days and he wanted me to back date one for him.

Of course that was illegal, but I had access to the cover note books and I could do it. Our motor insurance section was small, only two of us and I was the junior, but my senior was on holiday, so that particular problem was already taken care of.

I thought it through and the risks seemed fairly low. One of the cover note books hadn't been touched since yesterday, so I could date a cover note from this morning and it would be in sequence. I could tie the cover note in with the quote we had obtained for Mark earlier in the week and it would all look perfectly normal.

It was late in the day and some of the staff were already finishing; the weekend beckoned so everyone was keen to be off. The other girl who worked in our room was tidying her things away, so I waited until she had gone then went for the cover note book.

The building was fairly quiet so I hurriedly completed the cover note. The final item was signing and dating it and I put the cover down as starting at 9 am. I hadn't even had time to remove the top copy from the book when the director (and owner) stepped into the room.

He'd started this insurance broking firm sixteen years ago and he'd built it up into a small, but successful business. In many ways I admired him - a lot of the success was down to his hard work and forceful personality. If you were prepared to work hard and do your job, then he was a good boss, but he had no patience with time wasters.

His entry startled and confused me and he couldn't fail to notice this. He asked a couple of questions about how the work was going in the absence of the senior motor clerk. I could answer that easily enough, but then he asked about the cover note book open on my desk. I lied and said it was a late order. He moved a couple of paces closer and spun the book round so he could read it. He took his time reading the page, then fixed his gaze on me.

"This is for your brother isn't it?" I nodded dumbly. "Why is it dated from 9 o'clock this morning? He's had an accident hasn't he?"

Years of dealing with dodgy clients and dubious claims had perfected his ability to home in on the key details and unfortunately I was getting a perfect example of that. With just a couple of questions he'd got to the core of the matter and my defence was undone.

He picked up the cover note book and sheet containing the quote details, told me to wait there and left the room. I was left cursing my bad luck, my stupidity and my brother. Why had he skidded and demolished that garden wall? If only he hadn't got that cut which prompted a witness to ring for the police and an ambulance. He said it wasn't much of a cut and no one else was hurt, so if the police hadn't been called it would all have been containable.

Now I had to think about my options and they didn't look good. I would probably get sacked for this. I knew my boss liked me, in fact I suspect I was one of his favourite staff members, but that wouldn't make any difference.

To be honest a couple of the older women slightly resented me. I was young (twenty three), pretty with long blonde hair and a nice slim figure and as far as they were concerned it was clear why I got on with the boss. There was a lot of truth in that and even though I liked to think that I was good at my job, I was old enough to know that men stop using their brains when they're faced with a pretty girl.

I was trying to assess my options and my looks were about the only bargaining tool I had. That reminded me of a line in a book I'd read where one of the main female characters said a woman's main weapon was what she had between her legs and she had to learn to use it.

A wild and irresponsible idea blossomed in my head and within a few seconds became fixed certainty. I began to type and had got most of it down when the phone rang.

"Can you come through please."

I went through into the director's office and sat in the leather chair facing him. He asked me for an explanation and I described my brother's accident and how it could have been dealt with quite easily if the police hadn't become involved. I was sat at an angle and my shortish skirt was exposing a fair bit of leg. My boss couldn't help himself and kept sneaking glances despite the very formal situation.

He wasn't distracted too easily because he told me that he was very disappointed that such a promising member of staff should act in this way and he expected my letter of resignation to be on his desk on Monday morning. He said he was working late, that I should tell him when I left the building and with that the interview was over.

I went back into my office and finished typing the letter I'd started. I sealed it in an envelope, picked up my things and went along the corridor to the director's office. I knocked, entered when he called and, slightly to his surprise, placed the envelope on his desk.

A minute later I was out of the building and my boss was shifting uncomfortably in his seat as he read my letter.

"As you know I live two minutes walk from here at Flat 317, Archer's Court. At 7 o'clock precisely you will ring the doorbell three times in quick succession. I will buzz you through and you should take the elevator to the third floor. My door will be unlocked, so you can enter, but lock it after you.

The door to the dining room will be open. A single red bulb will light the room. I will be face down across the dining room table. You will put the cover note on the table next to me. You may pull my skirt up so that it is round my waist and then smack my backside. You can pull my knickers down and smack my bare bottom, but you can only use the flat of your hand. You may not use a cane or other implement. If I cry you may ignore that and continue to spank me until you are satisfied. You may not fuck me.

When you have finished you will let yourself out and neither of us will ever refer to this episode."

I let myself into my flat, quickly tidied round and then nipped into the shower. I was out of the shower by 6.35 and that gave me time to dry my hair and get dressed. I chose a lacy black bra and pants set, black lace-topped stockings, a black suspender belt, a white blouse, a black mini-skirt and black high-heeled shoes.

As soon as I was dressed I placed the two voice recorders I had "borrowed" from the office in opposite corners of the room, but made sure they were discretely hidden. I changed the main bulb for a red one, drew the blinds and waited.

Of course the big question was whether my boss would take the bait. I was fairly confident that he would. A few months ago I had happened to see him slipping a padded envelope into his desk drawer in an oddly furtive manner. Soon afterwards I found myself alone in his office and checked to see what the secret was. The envelope contained a book and magazine. The book cover showed a young woman draped across a man's lap. Her skirt was rucked up round her waist and revealed white panties drawn tight across a shapely bottom.

The magazine contained stories illustrated by photos of young women in various stages of undress and culminating in their being spanked by older men.

My initial reaction was one of disappointment that this man I admired for his business and people skills had such a basic weakness. I had never thought of him as kinky or perverted, he had always seemed completely normal, so I suppose that made the shock even greater.

Somewhat to my surprise I was intrigued by this secret aspect of my boss's life. He was in his early forties and married with two teenage girls still at school. Was his wife aware of this kink? Perhaps she indulged him and allowed him to spank her. I felt I was glimpsing adult behaviour of a type which I hadn't really encountered before.

I should add that I wasn't a virgin. I got engaged when I was eighteen and my fiancé and I had sex many times, but the relationship came to a halt and we split up when I was twenty. Since then there hadn't been much, though I will admit to a couple of flings.

My parents had helped me buy this city centre flat eighteen months ago and I was very cautious about bringing men back to it, so in truth it had been a quiet period for me sexually.

I can honestly say that it was only for my brother's sake and with a lot of reluctance that I was willing to let my boss spank me. As far as I was concerned my boss was an old man; I'm sorry but to a twenty three year old woman, men in their forties simply aren't on the sexual radar.

Having said that my boss was reasonable looking and still fairly trim (no beer belly thank goodness). At five foot eight inches he was only a couple of inches taller than me and with these heels on I would have a height advantage.

What if he didn't appear? I shook my head and dismissed that thought from my mind. There were times when I'd intercepted his lustful glances at me; the opportunity to spank me would surely be too tempting for him to resist.

The clock seemed to move with frustrating slowness; if this was going to happen I wanted it to happen quickly. Finally it turned seven and I'd no sooner told myself that he was late, than three urgent rings of the door bell startled me. I went across and pressed the intercom button so he had access to the foyer.

With my heart hammering away in my chest I draped myself across the table. My left cheek was resting on the cool wood with my head turned towards the window, though of course the blinds were drawn and looked an unfamiliar reddish colour because of the bulb I had fitted.

I didn't have long to wait before I heard the flat door opening. My boss was careful and quiet but I heard the reassuring click as he locked the door behind him.

I suppose there was the faint possibility that he had come to tell me that my scheme wasn't going to work, but realistically how many men would turn down an attractive young woman spread for their pleasure?

He entered the room and stood for a moment. I asked if he'd brought the cover note and he said yes and then placed it on the table next to me. I should really have checked it, but funnily enough I trusted him. I told him he could take his jacket off if he wanted to and then start whenever he was ready, but what happened today would never be referred to by either of us and we would maintain a pleasant work relationship.

He seemed slightly surprised by this rather business-like approach, but said he understood that and agreed to it, not least because it suited him. There were some sounds which were obviously him removing his jacket and hanging it over a chair back. Then he moved in behind me and with a firm, but smooth motion pulled my skirt up round my waist.

I had chosen a pair of lacy black knickers so my toned cheeks were already partly visible. There was a slight sound which I interpreted as him drawing his hand back, I tensed in readiness, then there was the first crack as his hand slapped down on my backside.

To be honest it was so cautious that it qualified as a play slap. That was a relief as the obvious worry was that he would be over-enthusiastic. It also suggested that he wasn't very experienced in the reality of chastising women. Still I had no idea how many smacks he was going to deliver and I had told him to ignore me if I started to cry.

In the event there were six smacks before he paused then grabbed hold of the side of my panties and pulled them down so they were round my knees. The sight of a trim female backside perfectly framed by black stockings and suspenders must have energized him because the next strike had the vigour of a blow, not a playful smack. I yelped slightly and twitched before regaining my composure.

Two more vigorous blows followed, the second one made me stagger slightly, so he must have been able to see everything. More smacks echoed around the room, my backside was on fire and I began to whimper and sob. The smacks were relentless and I wasn't able to hold back the tears.

I don't know if he stopped spanking me because he was satisfied or because I was sobbing uncontrollably. Either way the room fell quiet and I struggled to hold back the tears and regain my composure.

I wasn't sure what his next move was going to be. I thought he might resume spanking me and I really didn't want that, though I would have accepted it. In the event he reached out and gently caressed by bottom. That startled me and I wasn't sure what to say because although I had made it clear he couldn't fuck me, I hadn't said anything about touching.

"How does that feel?" he asked.

"Burning."

His hand drifted lower, his fingertips skimming the inside of my thighs. My insides convulsed as he made the lightest of contact with my pussy. The fiery pain of my bottom faded into the background and I realised that my sex was responding. I don't think I'd ever been so aware of my pussy. I could feel it pouting wetly. It honestly felt like it had a mind of its own and was reaching out to his cock, tempting it and seducing him to plunge his cock into my velvet slit.

Almost without thinking I parted my legs in an unspoken invitation and moaned as his finger slid into my pussy. I felt an odd mixture of embarrassment and lust. Embarrassment because he couldn't fail to notice how wet I was and lust because I was in a situation where everything seemed to be saturated with eroticism. The obvious next step was signalled when he removed his finger and unzipped his trousers.

"No, you can't do that," I groaned.

"Do you want me to stop?"

The words wouldn't come and all I could do was shake my head. Looking back that was a bit ambiguous. Did I mean he couldn't do that or was I saying that I didn't want him to stop? I knew what I wanted - I wanted him inside me.

The hard, rubbery tip of his cock pressed against my pussy and the state of my arousal meant that my cunt lips parted eagerly and he slid into me. I gasped, he groaned and then we were fucking. You've got to remember that I hadn't had sex for a while and abstinence intensifies the sensations. Despite the fact that he was a much older man who I normally wouldn't have let anywhere near my body, I couldn't help but respond to the situation.

To my surprise and somewhat to my shame we hadn't been fucking long before I began to shudder and shake with a very intense orgasm. My boss obviously realised what was happening because he urged me to cum. He got very excited because he started talking dirty to me. My boyfriend had never done that, but although it shocked and surprised me I can't deny that I got a thrill from my boss telling me what a lovely tight pussy I had.

"In fact it's so tight it's going to make me cum. I'm going to fill your pussy with sperm - are you safe?"

"Yes."

"Do you want it?"

"Yes, yes," I babbled.

"What do you want?"

"I want you to do it, cum in my pussy."

That obviously got to my boss because he gripped my hips as though his life depended on it and I felt his prick his stiffen and swell. Then it was jerking inside me and there was that lovely warm, wet feeling when a man fills your pussy with sperm.

My boss collapsed on top of me and I lay there with him covering me. I was wondering how I was going to bring this to a conclusion, but then felt his prick starting its inevitable retreat. I didn't want the embarrassment of sperm dripping out of me and onto the floor, so I asked him if I could get dressed. He moved away and began to adjust his clothing. I pulled my panties back into place and tugged my skirt hem; that was all it took and I was properly dressed again.

There was an awkward atmosphere; I suppose it's not surprising that neither of us knew what to say. For a couple of years we'd had a formal employer/employee relationship, but suddenly here I was with his sperm in my pussy. I moved towards the door, my boss took the hint and a few seconds later I was closing the door behind him.

I wandered through into the bedroom and changed my clothes. My knickers were stained and wet so they went straight in the wash and I used a tissue to wipe the excess sperm leaking out of me. It was clear that my boss had pumped a full load into me.

After that I got a bite to eat and settled down to watch the TV. Or rather I tried to watch; I must admit I was worried that this wasn't going to be the end of it, but I tried to put that thought from my mind.

Inevitably those thoughts returned when I went to bed. I also found myself thinking about the moment when my boss mounted me and his cock slid between my cunt lips. My hand strayed downwards and I replayed what had happened as though it was some sort of personal blue movie. I experienced another shuddering and very satisfactory orgasm and must has drifted off to sleep soon afterwards.

I was a bit apprehensive when I went into work the next day, but it was just another working day. There was no comment or even hint about last night from my boss and it was as though it had never happened.

My brother got his cover note, but I made it absolutely clear that if there were any similar problems in the future then he was on his own. Of course I didn't tell him what I'd had to do to retrieve the cover note.

In the event I moved to another firm about eight months later. It was a more senior position with a higher salary, but I did wonder if subconsciously I did it to get away from my boss.

That was fifteen years ago and I'm married now with two young children. I've never mentioned that incident to my husband and in some ways I'd almost forgotten about it. Then one night recently I'd forgotten to do something and my husband Mike gave my backside a playful slap and said I'd been a bad girl.

The circumstances were very different but it all came flooding back. I went upstairs and checked that our daughters were asleep, then slipped into our bedroom and changed. Coming downstairs in high heels, a silk blouse, a short skirt and my sexiest underwear I felt very nervous and excited.

I opened the lounge door and flicked the main light off. Mike stared at me in astonishment.

"You're right I have been a bad girl and bad girls have to be punished. Would you like to smack my bottom?"

Mike continued to stare at me and eventually I had to repeat the question. He just nodded dumbly and I draped myself across his lap. The first couple of slaps were pretty lame, so I told him that he should pull my skirt up. I hoped the sight of my lacy Brazilian knickers would inflame him. They certainly exposed quite a bit of my backside, but fortunately I've kept in good shape and still have a nice trim behind.

"Bloody hell Julie," he whispered. "Your arse looks perfect."

"Then give it a good spanking!"

His hand clattered down with extra vigour. A few more blows and without any prompting from me he pulled my knickers down and began to chastise my bare bottom. I gave an occasional yelp, hoping that I wouldn't wake our daughters, but finally cracked and asked him to stop.

tony090909
tony090909
1,498 Followers
12