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Phone Blackmail Ch. 02

By: emma_sturton



Chapter 2 – First Day Back At Work

As the alarm clock buzzed me awake from my disturbed sleep I was tempted to roll over and spend the rest of the day in bed. It was Monday, two days after my humiliation at the hands of John and Simon. At the back of my mind I knew that they would make me pay for any attempts to escape from our deal.

I got out of bed, pulling back the duvet with reluctance. The air was cold against my naked skin, and I dashed quickly across to the bathroom to take my shower. The warm water felt good as I caressed myself to wakefulness. After, as I got dressed I deliberately chose very conservative clothing, knowing that John and Simon would probably do their best to humiliate me again. I put on a pair of thick cotton panties, long black trousers, a white bra, white vest, blouse and jacket. Hopefully all the layers would protect me against their plans. 

As I logged on to my computer at work, there were six messages in my inbox. My hands were shaking as I clicked on the one sent by Simon:

‘Emma,

Thank you for agreeing to our deal. Just to clarify – you will have all of the evidence returned to you by 24th July if you agree to both mine and John’s requests. If you break the deal I will have no option but to turn the evidence over to the police. 

My first request for today is that you must only wear two items of clothing all day (excluding socks or shoes). I will inspect you at random times during the day to check that you are fulfilling this request.

Yours, Simon.’

I quickly weighed up my options with only two items of clothing – it would have to be trousers and vest, but nothing else! There was no other combination I could try, and I knew that Simon would have already realised the outcome. I went to the bathroom, removed my panties and bra. Checking in the mirror I was relieved that I’m quite small on top, 32B, and my breasts didn’t look too out of place contained within the white cotton vest. The loss of the panties wasn’t that much of a problem – I was just pleased that I’d chosen trousers rather than a skirt that morning.

As I returned to my desk I noticed Simon watching me across the open plan office from the door of his private office in the corner. He smiled, obviously realising the contents of the brown paper bag I quickly stuffed into one of my drawers. I glanced away, blushing at his knowledge of my state of undress. 

There was a new message waiting in my inbox – this time it was from John, the original phone blackmailer from Saturday’s humiliation. The request was short: 

‘Well done Emma – now I want you to take off your trousers.’

I couldn’t believe it – how could I take them off without completely humiliating myself in front of the nine or ten staff in the office? As my panic calmed a little, I realised that as my chair was against a wall, the desk itself would provide a barrier between me and anyone else. As long as I didn’t stand up I’d be able to remain hidden quite easily. I unzipped the trousers at the side, checking carefully that no one was watching, stood up just a little so that I could pull them off and sat back down again quickly. I was now naked from the waist down.

The next couple of hours passed quite easily, I had to ring around some suppliers, check some issues with marketing and answer a couple of letters. I actually felt quite good sitting there in just my vest top, although the air-conditioning was just a little on the cold side! My first problem came just after eleven when another buyer, Keith came over to discuss his recent trip to Italy. As he approached I quickly rammed myself as close to the desk as I possibly could, trying to minimise the chance of him seeing my nakedness. For a second I thought he was going to come round to see me, but luckily he sat across the desk from me, and my humiliation could remain secret. Just as he was telling me about a new manufacturer he’d located in Milan my phone rang. 

‘Emma, it’s Simon here. Could you get rid of Keith and come into my office please.’

Trying to remain calm I replied, ‘OK, but I’ll have to, erm, reinstate the clothing.’

‘That’s fine – just get here ASAP.’

It was more difficult putting my trousers back on after Keith had left. The office was busier now, and it was hard finding a gap when no one was close enough by to see what I was doing. Mission accomplished, I went over to Simon’s office as requested. Simon was waiting behind his desk, and John was sitting on the sofa next to it.

‘Emma, do come in. John and me were just saying how fantastic you’ve been this morning. You’ve been a brilliant sport yet again! I’d just like to check the ‘two item’ thing if that’s OK with you?’

I couldn’t believe how brazen he was about the deal. I thought they’d both be much more muted with their blackmail in the work environment. I nodded, but asked, ‘Could you close the door please?’

‘I’m afraid not my dear. Now John here will just check that you’ve completed your first little task for today.’

John stood up and walked over to face me. I couldn’t look him in the eyes. He started at my feet.

‘Shoes don’t count towards the total, but your trousers do. Could you please demonstrate that you’re wearing nothing underneath them?’

I was about to protest, but knew yet again that I had to continue. I unzipped them and quickly gave them a flash of my neatly shaved pussy. They both smiled appreciatively as John continued.

‘Your vest makes up the full quota. Are you wearing a bra?’

Again I was forced to demonstrate my compliance with the deal. Standing in the middle of my boss’s office I gripped the hem of the cotton top and pulled it up quickly. They were treated to the sight of my small, but pert breasts with their stiff, dark nipples. I lingered for a second before pulling my top back down, perversely enjoying their stares. Just as on Saturday I’d began to feel the stirrings of some exhibitionist feelings, I realised that I was beginning to enjoy my submissive role to these two men.

Simon spoke up, ‘Excellent Emma! Now there’s just one thing we’d like you to do now before we let you go. Pete Young and some of his team are coming across from Head Office this afternoon to view some of the new ladies wear designs. We had booked a model to show off the new outfits to them, but unfortunately her agency’s just called in to say she’s sick. Could you fill in please?’

Simon knew that I’d tried to make it as a model before I started to work for him, and he also knew that I wouldn’t be able to refuse his offer. I nodded, and the scene was set for the next stage of my humiliation.

The meeting room was to be used for the ‘fashion show’. It was quite a large room, and one row of four chairs each had been arranged either side of the ‘catwalk’. Simon explained that there were ten outfits that needed to be modelled, and that I could get changed behind the (small) screen in the corner of the room. John would be available to help out if I had any problems.

The appointed hour came and I was introduced to Pete Young, the company’s marketing director, by Simon, ‘Pete - meet Emma. She’s one of the stars of our buying department and has gamely agreed to fill in for the model who called in sick.’

Pete was handsome and in his early forties. He flashed me a lovely smile as he shook my hand, ‘Nice to meet you Emma. It’s very good of you to fill in like this – I really appreciate it. It’s important we make the right decision about these outfits. I hope you don’t mind my colleagues here as well?’ He gestured towards the two females and three men who made up the rest of his team. I shook my head and returned his smile.

The time had arrived for me to begin the show. I went behind the screen which, although it was wide, was probably just less than five feet tall. I’m tall, about 5, 10”, so I had to crouch down to avoid any chance of my breasts being visible to the audience. I knelt to pull off my vest top and my trousers. John poked his head around the screen to check on me. His eyes lit up at the sight of me kneeling naked at his feet. He selected the first outfit, a loose yellow cotton summer dress that finished just above the knee. The thin straps kept slipping off my shoulders as I walked out to show the audience. 

Luckily, having been a model for six months or so before starting in retail I was used to having strangers’ eyes burning into my skin. I paraded up and down the catwalk twice before one of the women, aged about fifty or so, called me over. ‘Could I just feel the material please?’ I nodded and she rubbed the hem of the dress expertly between her thumb and forefingers. I prayed that she wouldn’t lift the hem too high – I still wasn’t wearing any panties! She asked again, ‘I just want to check the fit of the dress. Would you mind stretching upwards please?’ She was obviously used to commanding models / clothes horses around. I did as she asked, and felt the dress rise up on my thighs until it only just covered my nakedness. She went further, ‘That’s great – how does it feel?’

I replied, ‘Fine, although these straps do seem to fall off quite a bit.’ She stood up to face me and played with the thin straps, pulling them up and down to check them out. 

‘I see what you mean. Could you just put them down please and see how the dress hangs?’

I did as she’d asked and could feel the dress starting to slip down. The square neckline came to rest on the upper slope of my breasts, only just above my nipples. The woman tugged at the front a little and the dress slipped down further, exposing the upper aureoles. Thankfully she stopped before fully showing my nipples and said, ‘That’s fine, could we have the next outfit please – the red one?’

The next outfit was a red pleated mini skirt combined with a ‘schoolgirl’ look white shirt and tie. John, peeking round the side of the screen was obviously enjoying my looks of incredulity at the skimpiness of the skirt. I took a deep breath and steeped back out onto the catwalk.

In the bright lights of the meeting room the white shirt was basically transparent and my dark nipples were clearly visible through the thin material. The skirt was extremely short and I knew if I bent over just a few degrees, it would show most of my behind. The woman called me over again. She was obviously the most critical of the assembled team. She felt the material of the skirt, lifting the hem higher this time. I knew that the two men sitting either side of her could see my pussy by the gawping expressions on their faces. The woman carried on regardless, obviously unaware of my nudity beneath the skirt. She asked me to turn around, and this time felt the back of the skirt, again, lifting it to check the hang and quality of the cotton. This time my bare bottom was exposed to the whole row. She was so obviously used to the world of fashion that she didn’t seem at all fazed by my nudity. It was just the other two men and a younger woman who appeared shocked. Their expressions were priceless, and I could feel the warmth between my legs start to burn more fiercely. I think I was getting turned on by letting these strangers watch me half-dressed!

The next few outfits were pretty conservative and I was able to wear them without any problems about showing myself. The final one was different though, a nightdress – pale blue lace, very thin straps and finishing only barely below my pussy. I wanted to take it off and refuse to go out, but John reminded me about our ‘deal’. I took a deep breath and stepped out from behind the screen.

This time the woman sitting between Pete and Simon called me over. I recognised her as Carole, manager of the firm’s flagship Oxford Street store. She had a fearsome reputation in the business, but I’d always found that I got on well with her on the few times we’d met. She smiled up at me, ‘Thanks again Emma – you’ve done a great job here today. It’s beyond the call of duty to help out like this – thanks for being such a sport!’ As she spoke she held my gaze and continued talking about the nightdress, rubbing the material and lifting the hem just as the other woman had done. She seemed to be daring me to object as she kept slowly lifting the flimsy material. Pete and Simon were treated to a fine view of my shaven pussy as she talked - their eyes never leaving my nakedness for a second. Carole stopped eventually, smiling at me, almost seeming to commend me on my bravery. 

Simon followed me back to the changing screen as the others huddled together at the far end of the room to discuss the outfits, gross profit margins and supply chains. He whispered, ‘Emma, yet again you’ve been a true sport today. I almost think you’re beginning to enjoy our little tasks!’ I blushed at his suggestion. ‘Emma, we’ve finished with you today, provided you…’ Carole interrupted him as she walked over to our corner.

She asked, ‘Emma, would you like to go out for a drink after work tonight? There’s a couple of things I’d like to discuss with you.’ I agreed and she waited while I slipped off the nightdress and put on my vest. She seemed a little taken aback by my lack of bra, but kept smiling and looking at me while we continued chatting. Simon kept his position as well, facing into the room, away from where I was changing. 

I’m not sure what happened next, but somehow the screen fell forward into the room, collapsing in on itself. I guess Simon must have tipped it over ‘accidentally’ somehow. Instinctively I covered my naked pussy with my hands, but not before everyone in the room had looked over and viewed me wearing just my vest and nothing else, my pussy exposed to the world! Carole kindly picked up the screen to re-cover me, but not before my humiliation at the hands of Simon was complete. What would everyone in the firm think of me now? In a few seconds I’d been humiliated, and would be forever known as the ‘girl from buying who flashed her bosses.’

To be continued… 

Phone Blackmail Ch. 03



I thought I’d survived Tuesday without being humiliated. Simon and John were both away on a course and I had spent the day free from their blackmailing commands. The only problem I seemed to have was the constant smirking and lewd comments from some of the other staff in the office. They’d obviously heard about yesterday’s modelling disaster through the grapevine. I tried to brush off their jibes with a smile and a laugh, but by the end of the day it was beginning to get a little tiring. I almost snapped at them, but tried to restrain myself from sinking to their level. 

I was pulling on my jacket to set off home when my mobile phone rang. My heart sank when I realised it was Simon. ‘Emma, I’m having a little get together with some friends tonight at my house. I’d love it if you could come and help with the drinks and food.’

I protested, ‘But I was going out to the pictures tonight… ‘

‘I’m very sorry dear, but I need your help. You’ve had a day free from our contract today, and so I think you owe me some of your time. Remember what’s at stake – your career is on the line if you don’t keep your side of the bargain.’

‘OK, please stop reminding me – what time do you want me there?’

‘Come straight round now. You don’t need to get changed, I’ve got the perfect outfit for you!’

Worried, I asked, ‘What is… ‘ Simon ended the call before I could finish my question.

It was just after seven o’clock when I knocked at the door to Simon’s house in north London. Within seconds he appeared and ushered me in to the hall. He was acting friendly, obviously excited about his plans for the evening. I must admit I was excited as well – I knew I should be fearful of what could happen, but I had perversely enjoyed the previous episodes where I had been exposed. 

He waved me through to the kitchen and asked me to open the large white bag on the table. My hands fumbled with the zip before I managed to get it open. I took out the contents – it was my outfit for the evening. The silky black material was obviously expensive and felt nice to the touch. I finally separated the cloth into two garments – a pair of cami-knickers and a lacy vest top. Simon smiled at the obviously shocked look on my face, ‘I hope they’re your size. You can put them on now if you want. I’ve told my guests that I’ve hired an ‘escort’ for the evening – they don’t know that you work with me, so you can be assured that your identity will remain a secret.’

I was relieved about Simon’s assurance and asked, ‘Where should I get changed?’

‘Right there will be fine. I’ve just got a few things to finish off with the food while you change. The guests should be arriving in five minutes or so.’ 

Once again any pretence of privacy that I’d had was shattered. I turned with my back to Simon and took off my jacket. My blouse came next and I placed it carefully on the back of one of the kitchen chairs. Simon stopped me as I was about to unhook my bra and offered, ‘Here, I’ll help you with that!’ His fingers expertly unclasped the small hooks and he gently slipped the bra straps off my shoulders. I tensed, expecting him to try and grab at my breasts. I almost wanted him to take me, to turn me round and kiss me hard on the lips, to suck my stiff nipples, but he just went back to the fridge, continuing with his preparations.

I slipped on the black top that Simon had chosen for me. The thin straps led to the lacy neck-line which barely covered my breasts. The top was quite loose, probably a size too large. I’d have to be careful bending forward, otherwise my breasts would be on show. I unzipped my skirt, letting it fall to the floor, and pulled down my panties. Just as I was about to step into the cami-knickers Simon called over, ‘Emma could you just give me a hand with these canapés please?’ I went over, still naked from the waist down. I could have pulled on the knickers, but I somehow wanted to show myself to him. 

Simon was nonchalant about my state of undress, and didn’t even comment on my bare pussy. He showed me what to do with the tiger prawns and stood next to me, watching what I was doing over my shoulder. His hand rested against my bare bottom. I wanted him to stroke it, to let his fingers slip between my legs and feel my pussy, but once again he seemed almost oblivious to the opportunity.

It was half an hour after the guests had arrived that I finally began to relax a little. Along with Simon, there were four other men, friends of his from the Tennis Club. I was apprehensive about how they would treat me, but they were all acting very gentlemanly. I’d expected to be groped and felt-up but they all kept their hands to themselves. I helped to serve the drinks and canapés, all the while aware of my state of undress in the loose top and lacy knickers. As I bent forward to offer the platters of prawns and other nibbles to the seated guests I could feel the front of my top gape open. With my hands holding the heavy plates I was unable to prevent them from seeing my naked breasts and erect nipples. They all looked without any sense of shame, but no-one commented on my slip.

Simon called me into the kitchen just before we went through to the dining room for the main course. With just the two of us there he commented, ‘Emma, can I just say you’re being the perfect hostess. I can tell my guests are obviously enjoying having such a pretty waitress tonight. Now, we’re onto the main meal now, so would you please put on this apron and help to serve it out?’ He offered the apron to me; it was one of those that you tie around your waist, leaving your top half uncovered. I was fumbling with the ties, trying to make a knot when Simon laughed, ‘Emma, you don’t want to be putting it on over that nice lingerie. Please take your top and knickers off!’ I couldn’t believe what he was asking me to do, but knew that I had to do as he commanded.

I took a deep breath as I entered the dining room, carrying a bowl of roasted vegetables in my outstretched hands. The conversation stopped immediately as I went in and the men turned round to stare at my exposed breasts. The attention of all the strangers in the room made my nipples become more erect, they felt as if they were about to burst. I placed the bowl in the centre of the table, squeezing between two of the seated guests. One of them lightly stroked my bare bottom which was only inches from his face. I tensed a little at his touch, one side of me wanting to protest, the other side wanting him to carry on. I smiled down at him, hoping to allay any nervousness he may have been feeling. He continued with his gentle massage and I pushed my bottom back into his touch, encouraging him to continue. His hand moved slowly to between my legs and I adjusted my stance to let him feel my pussy more easily. While he touched me I checked out the reactions of the other guests, gazing into their staring, almost greedy, faces. Being watched like this made me very wet, and I could hear the slurping sound of the guest’s fingers as he rubbed between my throbbing pussy lips. I wanted him to slide one of his fingers inside me, but his touching stopped immediately as Simon came back into the room carrying the rest of the dinner. Simon laughed, ‘Hey, there’ll be plenty of time for that later! I’ve spent all afternoon cooking this food, so don’t let it go to waste – dig in!’

Simon forced me to dispense even with the skimpy apron as I served dessert. I was becoming almost used to being naked in front of strangers by now, and I met his request with silent resignation. As I poured the cream over each of the guest’s Pavlova I had to stand next to them, leaning over to make sure there were no spills. Each of the men touched me, hugging my waist or stroking my bare bottom. I didn’t protest at their gentle fondling, instead I encouraged it, continuing to smile and wiggle my behind as they touched me.

After dinner the men went back to Simon’s sitting room to have their coffees. I was waiting, hands clasped behind my back near the door to the hall when Simon announced, ‘I’m sure we’d all like to thank Emma here for her attentiveness this evening. I’ve certainly enjoyed the way she’s brightened up our meal with her gorgeous young body. Now Emma has sportingly agreed to finish off our evening with a bang.’ I tensed noticeably, worried at what he was about to suggest. He continued, ‘Emma has agreed to give just one of us a blowjob this evening. We’ve all got to put £50 into the pot, and the winner of the raffle gets to have this young girl’s soft lips wrapped around their cock!’ I gasped at the forthrightness of his proposal – he hadn’t even bothered to warn me! The men all smiled in anticipation and fumbled around in their wallets for the money. The pot of £250 was placed on the coffee table. Simon asked each of the guests to write their names on a scrap of paper. The scrunched up names were placed in a large brandy glass, and I was asked to pick. I closed my eyes, rummaged around for one of the tiny balls of paper and pulled one out. My hands were shaking as I nervously unwrapped the paper. My voice was very quiet as I announced the winner, ‘It’s Nigel.’

Nigel was the oldest of the assembled guests, probably in his mid-sixties. From their conversations over dinner I’d found out that he used to be Simon’s boss before taking early retirement. He had a nice smile, and had been very courteous and friendly towards me all evening. After he’d won the ‘raffle’, he joked, ‘Let’s see if I’m not too old enough to remember what to do!’ He stood up, and without any trepidation he unzipped his fly and let his trousers fall down to his ankles. His erect penis was straining at the front of his dark blue briefs. Simon nudged my elbow, and I woke from my daze.

I walked nervously into the centre of the room, surrounded by the other guests sitting in their armchairs. Nigel smiled warmly at me as I approached, which helped relax me a little. I knelt on the soft rug in front of him – my face opposite his obvious erection. I reached to grip the side of his briefs and pulled them down with a sharp tug. His cock sprang free, almost hitting me in the face. I knew I should have been repulsed by being made to perform oral sex on an old man in front of a room of strangers, but I wanted nothing more than to take his cock into my mouth. 

Nigel sighed as I gripped the shaft of his penis in my right hand. I slowly massaged it to its full size before closing my eyes and leaning forward to lick its tip. I pulled back the folds of skin and lightly licked his glans. His breathing began to quicken and I took the head of his cock into my mouth, continuing to flick my tongue over his tip. I knew that he was going to cum quickly and eased off a little, letting him relax his breathing. I cupped his sagging, hairy balls in my hand, rolling them around and massaging them. He gasped, ‘That’s fantastic – keep doing it!’. I went in for the kill now, taking almost all of his cock in my mouth and maintaining my gentle grip on his balls. His knees sagged a little before he came in my mouth. As he caressed my upturned face in his hands he kept repeating the mantra, ‘Oh my god! Oh my god!’ I swallowed his cum, licking my lips for effect as he gazed down at me.

A round of applause broke out from the ‘audience’ as I finished the blowjob. I smiled at the circle of men, almost wanting to ask, ‘Who’s next?’ Simon walked over to help me up from the floor. He gave me the money from the table and put his arm around my shoulders as he took me back to the privacy of the kitchen. ‘Emma, that was fantastic – you’re made for this kind of thing. I can’t tell you how much I appreciate what you’ve done. It’ll be a shame when our deal has finished’. The harsh reality of his blackmail began to invade my thoughts again, and I was pulled back into the real world. I felt vulnerable again and reached out to put on my clothes. He seemed disappointed by my actions, his face almost sulking. I had enjoyed the evening, but now wanted to leave as quickly as possible. I choked back the tears as I got dressed, the events of the evening replaying through my mind. I felt shame at what I had done, and almost panicked at the thought of what might happen at work tomorrow…



Phone Blackmail Ch. 04



Simon was the perfect gentleman towards me the day after my humiliation at the party. I'd dreaded going into work, worried about what he might say to me, and how he would treat me. I still couldn't believe what I'd done – performing an intimate sex act on his friend Nigel in front of a room full of strangers. I tried to rationalise my feelings of excitement at being made to perform the act with my deeper feelings of shame. Since my blackmail had begun I'd alternated between thoughts of revulsion and genuine sexual excitement. 

It wasn't until just after three in the afternoon that Simon approached me with his next ordeal for me. 'Emma, how would you like to come and play some tennis at my club tonight? Carole from the Oxford Street store will be there – it might give you a chance to network a little.'

Resigning myself to the inevitable I replied, 'I guess so, but I haven't really got anything suitable to wear for tennis.' As soon as the words left my mouth, I knew that Simon would have planned for the event.

'That's OK, I've got an outfit for you to wear in my office. I'll just go and fetch it now.'

It was just after seven by the time my taxi pulled up to the tennis club in a leafy suburb of West London. I was clutching the bag that Simon had given me containing the skimpy outfit he wanted me to wear. In the changing rooms I spilled its contents onto the wooden slatted bench. Simon had selected an almost invisible thong that, from behind, left my entire bottom uncovered. The white skirt was pleated and very short, and the lycra bikini top was more like underwear than a suitable top for sport. I hurriedly changed into the clothes, checking out my reflection in the full length mirror. My nipples stood out through the thin material of the top, even my aureoles were prominent. The skirt left about the bottom third of my rear uncovered, showing off my bare ass cheeks. With a gulp of apprehension I walked round to one of the outside courts where we'd agreed to meet.

Simon greeted me with a hug, whispering his appreciation at the outfit in my ear. His hands casually felt my ass cheeks as he held his grip on me for a few seconds longer than felt comfortable. We were joined seconds later by Carole and Phil, an Australian friend of Simon's. She smiled at me, commenting on how nice I looked. I felt myself blushing, knowing how much of my body was on display. In contrast she was wearing a baggy polo shirt and jogging bottoms that covered much of her ample frame. We agreed to play mixed doubles, with me partnering Phil, and Carole matching up with Simon.

As Phil got ready to serve, I became aware of how much of my behind was exposed as I bent down to face the net. He would have been able to see most of my bottom and the thin strip of thong as I leant forward. I tried in vain to adjust my skirt, but it was no use – I'd just have to get used to it. As the game progressed it became obvious that we were the much stronger pairing. Carole had probably once been quite a good player, but she was a little too plump now to make any real difference around the court. Phil, who was friendly and helpful, turned out to be a very competent player, easily beating us all for pace and variety of shots. He seemed to enjoy coaching me, standing behind me showing me how to improve my shots. His arms reached around me, holding me close against his firm body. 

We won the first set 6-2, and as we were having a drink Simon whispered to me, 'Go and take off your thong right now.' I was taken aback by the tone of his command, but I knew I would have to acquiesce. I made my excuses and slipped back to the changing rooms to step out of my panties. I was now naked under the short skirt. I returned to the court and we began the second set. I could sense my pussy lips throbbing between my legs as I bent forward on Phil's first serve. He seemed to take forever getting ready, and I knew that he was probably checking out my bare ass and partially exposed pussy. After the first point he came over to talk to me, 'Emma, do you realise you've forgotten to put your panties back on?'

I didn't imagine that he'd draw attention to my nakedness, and I needed to think up a quick excuse. 'Yes – I got them wet while I was going to the loo. I haven't got any spares. Is it OK with you?' He smiled and we continued with the game. The second set was even more one-sided than the first and we won 6-0. As we sat on the benches at the side of the court, Simon congratulated the two of us and offered to 'up the stakes'.

'I think we need to introduce make the game a bit more interesting for this final set, don't you? How about if we all agree to lose an item of clothing if we lose a service game – we're the only ones out on the courts now, so it'll just be between the four of us.' I expected Carole to be shocked at Simon's wild proposal, but she seemed the keenest to start the game. I knew I had to agree, and Phil seemed OK with the idea as well.

Phil served out his game easily, sending three aces blasting down the court to send Simon lunging along the baseline in vain. Carole got ready to serve next, and I responded aggressively to each of her weak, lolloping serves. Within a minute or so we'd won the game and she gamely took off her socks. 

It was my turn to serve next and I knew what was at stake. I was only wearing my skirt, top and training shoes. I would have to win, or else! The first couple of points went my way, leading us to a 30-0 lead. Carole managed to return my next serve, and Phil for the first time in the game fluffed what was an easy backhand. Annoyed at Phil, I let my anger frustrate me and double-faulted on the next point. With the score at 30-30 I let the next serve rip down the court, Carole dived for her return and amazingly it came back over the net. Surprised that the ball had been returned I had to lunge to make my shot, only to see the ball skid of the rim of my racket into the net. I was break point down and needed to win the next point. I bounced the ball calmly on the service line, trying not to let Simon's jokey catcalls put me off. With a smooth movement I released the ball and smashed it as hard as I could straight towards Carole. She instinctively managed to play her backhand, and the ball shot towards Phil, waiting at the net. I knew he would be able to cope with the shot easily, but couldn't believe it when he seemed to almost deliberately volley the ball wide. We'd lost the game, and I had to take off an item of clothing.

Against my protests, Simon wouldn't let me count my trainers as an item of clothing, so I was faced with the choice between my skirt or top. With visibly shaking hands, I gripped the elasticised hemline of my top and pulled it over my head. Carole and Phil both let out a gasp as my pert breasts were exposed. Carole tried to make me feel a bit better, 'Don't worry Em, I'm not far behind, I don't stand a chance on my next serve.'

The next two games both went with serve, and both Phil and Simon could both remain fully dressed. As expected, Carole lost her game to love, and she was forced to take off her shirt, exposing her large, wobbly breasts in a plain white sports bra. With the game standing at 4-2 it was my turn to serve, and this time I was determined not to lose. Carole was equally determined with her returns, and I was shocked as the score quickly progressed to 15-40. I stood on the baseline with all sorts of thoughts running through my head, being topless now seemed no problem as I worried about having to take off my skirt. My first serve was poor, I hit it too long and now there was the chance of a double fault. Phil murmured some encouraging comments to me as I strode back to the baseline. A bizarre thought now entered my head, and I began to WANT to lose the next point. I imagined the sensation of unwrapping my skirt and revealing my pussy to Carole and Phil. The thought made me immediately very wet between my legs. I threw the ball into the air, and deliberately scuffed the shot, sending the ball whizzing into the net. Without a second thought I unbuttoned the skirt at the side and let it fall to the floor. The evening air felt lovely and cool against my naked skin. A spontaneous round of applause came from my fellow players, and I curtsied back in mock appreciation.

The next games passed in a blur – I ran around the court fully naked, enjoying the attention that I was getting from my three partners. As the light began to dim, Simon suggested that we finish and return to the club house. I was nervous about my state of undress now; worried that Simon would not allow me to get dressed again. My fears began to take shape as he strode towards me with my tennis outfit in his hands, a grin playing across his lips. He bent down to whisper in my ear, 'Emma, you can have your clothes back only if you agree to give us a 'show' here on the court.' I shook my head, refusing to believe what he had asked me to do. Simon shrugged and set off towards Carole and Phil, who were waiting by the gate out of the court. He still had my clothes and, yet again, I knew I would have to give in to his command. 

Simon heard my shouted assent and started talking to the others. The twilight air now felt cold against my naked skin, and I could feel small goose bumps start to form. I felt very exposed out on the court and covered myself with my arms, a futile gesture but it made me feel more comfortable. As I waited, wondering what type of 'show' Simon wanted me to perform. I kept seeing Carole and Phil gazing over, their eyes taking in my lonely, naked body. Eventually the three of them came back over to me.

Carole spoke first, 'Emma, I've always had a bit of a 'thing' about watching other people have sex – Phil has offered to take part, are you OK with that?' I couldn't believe how calm she was about the making the offer. I nodded and the four of us made for a secluded grassy patch near the perimeter of the club. Simon asked me to lie down; letting me use Carole's top as a blanket. I lay back, holding my knees together in temporary modesty. Phil stripped off his shirt and shorts, revealing an athletic, tanned torso. At least my experience might be pleasurable in one way – he was very attractive. Carole sat down near my face, her hands already inside her pants, rubbing furiously at her pussy. Her large breasts jiggled with her motion, straining to free themselves from her bra. As he pulled down his briefs, Phil's cock sprang free – it was long and thin, erect and ready to take me. He gently prised my knees apart and knelt between my legs. I closed my eyes and waited for him to begin.

The combination of Phil's gentle kisses on my face and erect nipples with Carole's noisy murmurings of pleasure made me wet very quickly. Phil could sense my increasing ardour, and he carefully slipped his stiff cock inside me. His hard thrusts transported me to another world, taking me away from the humiliation of being fucked by a stranger in the outdoors. Within minutes I came, thrusting my slim hips against his, squealing with pleasure at the sensations washing over me. Phil came seconds later, collapsing into my arms as his cum squirted deep inside me. He held me and kissed my neck and ears, reassuring me about how good the experience had been. When I opened my eyes I could see Carole still frantically rubbing her clit. As soon as she noticed my gaze she came as well – a long hard orgasm that seemed to last forever. 

I looked around for Simon. He was sitting a couple of yards away, nodding his head in appreciation at the scene in front of him. He winked and smiled when he saw me looking. I felt myself blush uncontrollably at his obvious approval of my wanton behaviour. I had done as I had been ordered and wondered what tomorrow might hold for me...



Phone Blackmail Ch. 05



John’s wife greeted me at the door to their house that evening, ‘Hi, you must be Emma. John’s told me all about you. Come and get yourself a glass of wine and meet the gang!’ She was very welcoming as I followed her through to their kitchen, commenting on how nice my hair looked and how flattering my dress was. I felt immediately at home, her friends were equally nice and I was soon chatting with the best of them.

The day had started at work with John pestering me for details about my experience the previous night with his co-blackmailer Simon. He seemed to delight in my faltering account of how I’d been made to strip on the tennis court and then have sex with Phil. Despite my obvious embarrassment he kept asking more intimate questions, relishing in my blushing red cheeks and murmured responses. Although I’d enjoyed my tennis experience to a certain extent, the cold light of day made my actions seem slutty and almost perverse. 

It was after his cross-examination that John broached the idea of going to his house that evening, ‘My wife Jane’s having one of those lingerie parties. I’ve already spoken to the organiser and mentioned that you’re willing to model some of the outfits. I hope you don’t mind?’

I replied, ‘Who’ll be there?’

‘Oh, just Jane and a few of her friends. I’ll be out the back playing cards in the kitchen with the rest of the boys.’

‘Do I have to?’

John fixed me with a steely stare, ‘Remember what’s at stake…’

The party organiser, Bev was obviously a pro at this sort of thing, soon putting everyone at ease in Jane’s sitting room. Her jokes and the constant flow of white wine loosened everyone’s inhibitions. After half an hour or so of the girl’s trying on basques, suspenders and other elaborate underwear over their normal clothes, Bev made an announcement, ‘That’s enough of beating around the bush – let’s get down to business. John mentioned that Emma here has agreed to model a few outfits for us – it’ll show them off a bit more with a real, live model. Are you still OK about doing this Em?’ I nodded, knowing that I couldn’t refuse.

Jane showed me through to the dining room next door, ‘It’s really good of you to do this for us Em. John mentioned that you used to do a bit of real modelling. You can get changed in here if that’s OK – Bev’s already laid out the lingerie for you to try on.’ Bev had thoughtfully numbered each of the four outfits with small, yellow stick-it notes. As Jane pulled the door half-closed behind her she laughed, ‘See you in a couple of minutes then!’

I pulled my thin silvery dress over my head and laid it on the back of one of the dining room chairs. I was braless and so just needed to step out of my white panties. I was standing naked with my back to the door as it opened. It was John, ‘I see you’re being a good girl again – well done!’ He then pointed over to a serving hatch in the wall that separated the dining room from the kitchen, ‘If you don’t mind I think we’ll open up these doors and let the boys have a little show as you get changed into your lingerie. I’ve told them that you like to be watched – is that OK?’ Yet again, I knew that to refuse was pointless. I’d gone too far with the blackmail to give in at this stage.

John opened the doors to the hatch quietly, ‘Here you go boys, say hello to my friend Emma!’ I was greeted by the sight of three faces staring at my naked breasts. They were all standing near to the hatch, like small children in front of a sweet counter. They seemed a little embarrassed, so John put them at ease, ‘Don’t worry, Em likes to show off – she’s a bit of an exhibitionist you know.’ As if to reinforce his point he gripped my arm and forced me to give an impromptu twirl for them. Their eyes took in the sight of my full nakedness, my small, pert breasts, shaven pussy and tight bottom. Yet again, I could feel a warmth flow through me, secretly enjoying my forced exposure to these strangers. Before leaving to go back to the kitchen John announced, ‘We’ll have to keep a lookout – we don’t want to be caught spying by the girls.’

Just as the door clicked shut behind him, Bev called through, ‘Get a move on Em – we’re waiting for the first outfit!’ I hurriedly pulled on the sheer white panties, pull-up stockings and clasped the strapless bra behind me. 

The girls were appreciative as I modelled the lingerie, but not as appreciative as my audience in the changing room. Every time that I tried to cover myself or limit what I was showing to the men, John would ‘tut’ at me and force me to be more expressive. I returned from the living room to try on my final outfit – a baby doll nightie. I was greeted by the shocking sight of two erect cocks poking through the serving hatch. They looked pretty strange kind of squeezed together like they were, like a pair of kebabs waiting to be skewered. Before John spoke, I knew what he was going to say, ‘Emma, you’ve gone and got all of us a bit worked up with your sluttish behaviour. You could have at least closed the doors while you were undressing. I think it’s the least you can do to help Graham and Bill relieve themselves.’ 

I glanced around me, knowing that I’d have to work fast to avoid the girls becoming suspicious. I changed quickly into my nightie and scurried over to the hatch. I grasped a cock in each hand and felt both men quiver at my touch. As I slowly and firmly rubbed up and down their shafts, I let some moisture from my mouth drop onto the tip of each cock. My tongue came next, licking the end of each cock in turn as their drawn foreskins exposed soft, tender skin beneath. The cock in my left hand was thick and average length – it felt like a rod of iron is my small, clenched fist. The other was longer but equally as thick. Both cocks were responding well to my attention, and I hoped they’d both come quickly. As I put the left cock in my mouth, Bev shouted through to me, ‘Hurry up, we’re waiting Em – what are you up to in there?!’ I had to pull the cock out of my mouth to murmur my reply. I could feel both men starting to give in to the pleasure of pushing their cocks into my mouth. I could feel their bodies start to tense just before they finally ejaculated. Their cum shot in the air and I had to jump out of the way to avoid it splashing my outfit. I breathed a sigh of relief, quickly checked the nightie looked OK and went back through to the living room.

It was about half an hour later when Bev suggested that the girls should join the boys back in the kitchen. Everyone had ordered some of the lingerie, and she seemed pleased with all the sales she’d made, ‘I’ve got a bottle of champers chilling the fridge – would anyone like to help me drink it?’ It was only when we got to the kitchen that I realised I was still wearing the skimpy baby doll nightie. It barely covered me, and under the harsh fluorescent lighting of the kitchen it seemed to be almost transparent. The men were still playing cards around the table, they’d obviously cleaned up after themselves and the serving hatch was now closed. From the wide grins from two of the players I guessed who Graham and Bill were. The memory of having their cocks in my mouth was still vivid. 

By now everyone was pretty drunk and there was still an hour to go before the taxi’s everyone had ordered were due to arrive. John suggested to the group that all of the ladies should try modelling the lingerie and do a fashion show for their partners. The sounds of the girls’ protests soon faded and they jokingly agreed to strut down the catwalk. We all crowded back to the impromptu changing room, and I wasn’t surprised to see the serving hatch was now very slightly ajar. The boys were indulging in another peep show, but at least I wasn’t alone this time. 

The other girls quickly changed into a variety of lingerie while I stayed in my nightie. Jane bravely agreed to go through first, ‘I am the hostess after all, it is the least I should do…’ She looked good in a matching black bra and thong. She was quite small, probably only 5’ 2”, but she had very large breasts and an ample, firm behind. The black material of the lingerie contrasted well with her pale, white skin. We could hear whoops of approval from the kitchen as Jane walked in, the wolf whistles were loud and raucous.

It was about ten minutes later that Bev and I were left alone in the changing room. Each of the girls before us had received a round of applause in their outfits. The loudest reception had been reserved for Karen, Bill’s wife, who had bravely agreed to wear the see-through camisole and knickers. Bev looked over at me, ‘Well Em I wouldn’t mind wearing that nightie you’ve got on – I don’t think this bikini would flatter me all that much!’ She held up a tiny string bikini which barely had any material for coverage. She was quite a buxom girl, and she was right that the bikini would suit someone skinny like me. I nodded and pulled the nightie over my head, handing it to her just as she unclasped her bra. Her large, floppy breasts fell free and she put the nightie on. I had to unravel the bikini before I could wear it. I tied the string on one side of the bottoms and very inelegantly fumbled with the string on the other side as I tried to get it fastened. I could hear the wolf whistles greeting Bev’s entrance as I tried to get the top tied as well. The bikini was extremely skimpy, tiny triangles of white cotton covering my nipples, pussy and rear. I felt as good as naked as I stepped into the corridor, ready to greet the crowd of onlookers in the kitchen.

I took a deep breath as I pushed open the kitchen door. The crowd was in a semi-circle in front of me. The couples were standing together. Each of the husbands (who were now either naked or just wearing their shorts) had their arms around their partners, calmly fondling their breasts or rubbing between their legs. The lights had been dimmed and I could sense a change in mood. Everyone was silent as Bev stepped towards me with her hands behind her back. ‘Em, there’s just one thing we’d like you to try now if you don’t mind. John’s explained that you like to ‘perform’, and you don’t need to worry as you’re amongst friends here.’ She then revealed a large, black ribbed vibrator that she was hiding behind her back. I gasped at the sight of it – it was much larger than anything I’d ever seen or used before. She turned it on, and some of the audience giggled as it began to slowly gyrate in her hand. My reaction was one of horror – what was I supposed to do?

John could sense my unease and stepped towards me, leaving his topless wife leaning against the dishwasher. ‘There’s no need to worry Em – we’re a close knit group here, you’ve got nothing to fear.’ He calmly reached out and untied my bikini top behind my neck. He kissed me lightly as he did so, his breath smelling of beer and cigarettes. I must have tensed a little at his touch, so he whispered in my ear, ‘Remember what’s at stake…’ His reminder of the blackmail made me more willing to go along with his commands. I untied my bottoms myself and lay down on the floor, pulling my legs apart to reveal my throbbing pink pussy. John joked to the crowd, ‘I see we’ve got a natural here!’ He rubbed my pussy lips to check I was wet and took the vibrator from Bev. He let the tip touch against my clitoris and I jerked with pleasure.

Most of the group had arranged themselves in a circle around me in the centre of the room. Karen was licking Bill’s stiff cock as he played with her pussy through the flimsy material of her knickers. His eyes were fixed intently on my pussy as John gently used the vibrator to massage my clitoris. Graham and his girlfriend were both kissing Jane as she knelt naked near my head. Bev had stripped off as well, and was licking Andy’s nipples furiously as his wife sucked on his long, thin cock. This orgy going on around me added to my already heightened sense of excitement. I tried to delay my orgasm, wanting first to feel the massive thick vibrator inside me.

I begged John to put it inside me – he shook his head, and instead knelt between my prostrate legs. He let his large cock out between the flaps in his boxer shorts and pushed it deep inside me with a quick, hard thrust. It hurt a little at first, but after we’d found our rhythm it was fantastic, our groans adding to the moans of pleasure coming from the others around us. John was very attentive, kissing my neck, nibbling on my earlobes and gently squeezing my nipples. His thrusts became harder as I began to playfully bite his nipples. By now Jane had left Graham and his girlfriend to themselves. She joined us – sitting astride my face as she faced towards her husband. I licked at her very wet cunt, enjoying the sound of her moans as I sucked at her clit. She came first, almost suffocating me with her legs as she collapsed into a heap on top of me. John followed, and I came almost the second after I felt his cum squirt inside me. John lay next to me and leant over, his words barely audible over the sounds of our heavy pants of ecstasy, ‘Em, you’re doing so well – that was fantastic. You’ve only got one day left before we hand over the stuff to you. Simon and I have got big plans for you tomorrow at work…’ Before I could ask what was to come, he rolled over to hug his wife on the floor. I could feel a cold shiver run through me as I began to wonder what would happen on the last day of my blackmail…



Phone Blackmail Ch. 06



As I stepped into the office that morning, my thoughts were taken up with the belief that finally my torture of being blackmailed would be ending soon. Simon and John had promised to return the evidence of my wrongdoings, and I would finally be free from their orders of humiliation. As I sat at my desk my mind wandered back to some of the events of the last week – exposing myself at the buyers' fashion show, being forced to be a naked waitress at Simon's party, letting Phil fuck me on the tennis court. Each episode brought back a mixture of memories, a sense of humiliation combined with an amazing sexual buzz. I'd been forced to unleash a side to my sexuality that I never would have believed existed. I'd discovered that I enjoyed exposing myself to others, that I became turned on knowing that strangers were watching me. I realised that I'd almost regret the blackmail ending, but at least in the future I'd be more in control of my exhibitionism.

My thoughts were disrupted by the sound of my phone ringing. It was Simon, ‘Good morning Emma, John's been telling me all about the little party at his house last night – sounds fun. I was just wondering whether you'd mind stepping into my office for a second. There's something I'd like you to do for me.' My heart raced as I walked across the busy office to his room. He greeted me at the door and gestured that I should sit down on the sofa. He took me by surprise by offering me a coffee and chatting about the new season's sales figures. I'd expected the usual terse commands, but he was more amiable today, perhaps realising that he didn't need to be so authoritative – he knew I'd comply with whatever he asked me to do. We chatted for about ten minutes before he finally changed the subject. ‘Emma, I've been very pleased with your behaviour this week. You've done everything that John and I could ask of you. I even think you've enjoyed yourself to a certain extent. Now it seems a shame that such a mutually beneficial arrangement should end, so I've got a little proposal for you.' My mind raced with conflicting thoughts as he continued with his offer, ‘We're proposing that you will receive all of the evidence of your theft today. John and I will then no longer have any hold over you, and you are free to leave the arrangement whenever you want. However, since we seem to have a good thing going together we're proposing that we'll pay you £500 for each week that you're willing to continue as our subject.'

I was taken aback by his offer – the money would certainly help pay for my own living expenses and my mother's care home fees, but I'd basically be selling my body for sex. Should I accept their proposal or walk away free from their blackmail? He sensed my hesitation and said, ‘You don't need to make your decision now – you can take some time to think about it if you want. All that John and I ask is that you tell us by the end of the day.' I thanked him for giving me the time and began to get up from the sofa. ‘Hold on a second Emma, we're not quite through yet! I've not told you about today's little game have I?'

I walked out of Simon's office five minutes later panicking about what I had to do next. He'd asked me to accompany John and himself to a hospitality day being held by one of our suppliers at a nearby race course. Normally I'd have jumped at the prospect of spending a day sipping free champagne and watching the horses. It was always nice to escape from the office and do some networking. Today's offer would have been the same, apart from Simon's order that I could only go if I took off my bra and panties. Unfortunately I was only wearing a very thin yellow summery dress with a short hemline. When I returned from the ladies' toilets five minutes later, minus my underwear, I felt very exposed – only thin cotton separating my nakedness from the outside world.

The taxi journey to the race track was fairly eventful. I was sandwiched between John and Simon as we drove through the busy roads out of town. John seemed to particularly enjoy gently pulling the hem of my dress up - each mile we travelled he would tease it a little higher until eventually my pussy was exposed. I tried to pull it down, but he stopped me – forcing me to sit on my hands instead. As the three of us stared straight ahead John pulled my legs apart a little so that he could rub between my legs. His slow, almost tender, massage of my throbbing clitoris was too much and I whispered in his ear, begging him to stop. His laugh at my request was accompanied by more frantic massage, his rough fingers rubbing hard against my clit. I squeezed my legs together as I came, almost breaking John's wrist. I tried to stifle my gasps of pleasure, trying not to attract the attention of the taxi driver. I failed though, as he spoke, ‘Is everything alright miss?' He turned to face me, watching with a smile on his face as I tried desperately to pull down my dress. His eyes stared at my exposed pussy for a second or so and I could feel my face blushing with the embarrassment of what I'd done.

John's close attention to me continued as we made our way to the hospitality box overlooking the race course. I was surprised by how forward he was being in public, his hands grasping my buttocks as we made our way through the crowds of racegoers. He kept lifting the hem of my dress, partially exposing my bottom. I knew there was no point trying to complain, he wouldn't listen and it would probably only serve to make him more eager to expose me. By the time we got to the box my embarrassment had almost disappeared, I was getting so used to being treated as his sex toy.

The hospitality box was large with a panoramic view over the rolling green of the race track. There were floor-to-ceiling glass windows at one end, and a table laid out with food and drinks on one side. Two men stood up from their seats as we entered. Simon spoke first, "Ron, Keith –hi! Glad you could make it. You know John, don't you? I'd like to introduce Emma, the young lady I've been telling you about.' My heart leapt at the thought of what he'd been telling these strangers. Both men shook my hand and looked appreciatively at my body, barely concealed behind the thin, yellow summer dress I was wearing. I could tell from their expressions that Simon had told them more than he should have done.

The first half an hour or so went without incident. The group of us sat around talking about work while we steadily made our way through a bottle of Margaux. Ron and Keith were old friends of Simon's and worked at one of our shoe suppliers. I even started to relax a little, losing my fear of what I might be ordered to do that afternoon. In a way I hoped that something would happen – so far I had enjoyed the games that Simon and John had made up for me. While we chatted I even had time to think over Simon's offer of money in exchange for being their ‘slave'. Should I take money for something that I was beginning to find pleasurable, or should I try and retain at least some dignity? I still hadn't made up my mind about what I should do.

It was five minutes before the first race when John changed the conversation away from work. ‘It's about time we made some bets on the first race. There's usually a massive queue to the bookies, so why don't we just bet between ourselves?' We all agreed to John's plan, and Simon continued,

‘Let's say a tenner per race – winner takes all.' He then turned to me, ‘However, I wouldn't want to take money from a lady, so Emma can offer something else instead!' The others laughed at Simon's suggestion, all eyes fixed firmly on my blushing face. He continued, ‘If Emma wins, then she can take the money, but if she loses she has to agree to do whatever the winner wants, at least until the next race.' I nodded in semi-reluctant assent and the five of us set about choosing our horse for the first race. 


Despite being the favourite and leading for the first part of the race, my horse ‘Helios' came in a poor third, about six or seven furlongs behind John's horse.  He turned to me with a wicked grin, ‘How lucky am I? I've just won £30 and I get the chance to order you around! I'm feeling a bit hungry now, would you mind taking off your dress and handing around the sandwiches?' His tone was matter of fact, and I didn't even bother to protest. I slipped the thin dress straps off my shoulders and pulled the dress down from the waist. My breasts popped out of the thin material to appreciative gasps from my audience and I then wriggled free of the dress, letting it fall around my ankles. I felt warm inside, knowing I was the centre of attention for this group of men. Ron and Keith both had their mouths open, gawping at my naked body. Until the next race, I enjoyed wandering around the hospitality box nude, offering the men sandwiches and canapés. Apart from the occasional bottom fondle or brief squeeze, the four of them remained calm and relatively inhibited in my presence. I was relieved the window of our box was not overlooked – at least my exhibitionism was confined to within the privacy of the four walls.

My resignation at not being able to pick a winner was confirmed when my horse fell at the third fence in the second race. Simon jumped for joy as his horse romped home by a short length. He accepted the congratulations of the others and then turned towards me, ‘Emma, as we're entertaining our suppliers it seems only fair that we let them sample your amazing blowjob skills. I'd like you to show Ron and Keith what you can do!' Without needing a second chance, both men kicked off their shoes and pulled down their trousers and shorts. They both looked a little silly standing in shirts and ties and naked below, but the size of their straining erections was much more serious. They stood about three feet apart facing each other and I knelt between them. I gripped Keith's throbbing cock in my left hand and took Ron's into my mouth. Both of them gasped at my touch. I slowly began to massage Keith along his long, thick shaft while licking at the tip of Ron's twitching cock. I deliberately took my time, trying to build both men up to a climax at the same time. I could sense Ron was about to come, and slowed my sucking, pulling Keith's cock towards me and putting the tips of both cocks in my wide-stretched mouth. The sensation of having two cocks in my mouth was amazing, both men struggling to hold back from ejaculating. Within seconds of each other they both came, their cum mingling together on my tongue and dripping down my chin. I struggled to swallow the combined volume of their cum, but managed eventually. Simon and John both clapped their hands at my efforts, their smiles and knowing winks making me feel even better.

We all sat down to have some food before the next race. Simon and John joined Ron and Keith in taking off their clothes, and the five of us were all naked as we sat around in the comfy armchairs. I took the time to look at their middle-aged bodies as we sat chatting. The four of them were all past their best to a certain extent, but nevertheless they all had an ease and maturity that I found exciting. I hoped that I'd lose the next race, and deliberately chose an 80-1 outsider as my horse. The race was almost over when there was a knock at the door to the box. I couldn't believe it when Simon got up and, despite being naked, went over to open it. ‘Hi Carol! Glad you could get here. We've been having fun as you can see!' It was Carol, the lady who'd enjoyed my naked tennis match so much. She seemed blasé at seeing four naked men and me sitting around in the box and took John's offer of a glass of wine without even flinching. 

As I'd hoped I lost the next race and Simon won again. Within seconds of his horse passing the finishing post, Simon spoke up, ‘Emma, would you mind undressing Carol for us please?' I jumped out of my seat and walked towards her. Her lustful eyes gave me the sign that I could proceed, and I helped her out of her jacket. My fingers fumbled a little with the buttons on her blouse. My nervousness was made worse by the suggestive comments from our audience. She turned her back to me to let me unhook her bra, releasing her large, floppy breasts. Her small, pale pink nipples were already erect. Her skirt came off easily and I knelt in front of her to pull down her panties. She seemed to moan with pleasure as I revealed her thick, bushy pussy to the room. 

Now John spoke up, ‘Thank you Emma, now would you mind letting Carol tie you up?' At this moment he took a napkin off the table and passed it to our new guest. Carol asked me to put my hands behind my back and expertly tied them together. John continued, ‘If you lose the next race Emma, I'm afraid we'll have to punish you a little – do you understand?' My heart sank at his words; he seemed to be hinting at something darker than anything they'd asked of me before. I started to protest, but his withering look was all that I needed to know my pleas were useless. I started to watch the next race, fearful of what would happen if I lost…