Gangbang Waitress

Gangbang Waitress
By: Fiona

AUTHOR'S NOTE AND BACKGROUND.

For years, I have been meaning to write about my life, and having found this site, I decided to take the plunge. I thought that my experiences might be worth writing about and that it would be a challenge for me. This is the first story.

I have to confess that as I look through the rough diaries I have kept over the years, re-living my sexual adventures is proving to be very arousing for me. However, in some ways I feel more embarrassed to be revealing my secrets than I was when the events took place in such a spontaneous and natural way.

After my first orgasm, while playing with myself when I was thirteen I have had a very high sex drive. In my final couple of years at my girls-only school, I would often have to masturbate in the toilets to ease the hunger in my pussy. I have since learned that boys do this a lot, but I felt terribly guilty then. I even considered going to the doctor about it, but I never had the nerve. Also, I had a terrible battle with those feelings of guilt, since I had a religious, middle-class family upbringing. However, I knew that I had to come to terms with my sexual demands and learn to enjoy them, and eventually, after I left home for University, I succeeded.

I am now twenty-six, but when I went to University in England, aged eighteen, I had never experienced penetrative sex with a man. However, my hymen had been well and truly broken by then because of my masturbation with fingers and various implements. I bought my first vibrator by mail order, when I was sixteen. I should mention that when I registered with a doctor in England I immediately started on the contraceptive pill, and have continued it ever since.

What might amaze you ( it did me) is the way that, once I had taken the plunge with fucking, I so quickly did things in a few years, that most women will never experience in their lifetime. When I discovered the sexual power that I could have over men, it added a mental addiction to the physical demands of my body. It helped to transform me from a sexually inexperienced girl into a voracious vamp. I also enjoy being an exhibitionist, glorying in the effect I can have on men by flashing my boobs or pussy at them.

The main thing for me, is that having come to terms with my sexual nature, I have become a free spirit, happy and liberated, with no hang-ups. I think that is very important.

I am slim and petite, five feet six inches tall, with brown eyes in a face which I think of as plain rather than pretty. But at least I have two assets; my silky, red hair which I always keep long, and my 36B bust which looks even bigger on my girlish frame. I do need to wear a good bra, most of the time, and I can attract a lot of attention with low-cut, uplift styles.

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GANGBANG WAITRESS.

The events described here, happened in my first year at Uni. By then I had been fucked by several of my fellow students, and was thoroughly enjoying it. I was just able to get by financially, but I was desperate to buy a car. My parents thought that was an unnecessary luxury and were contributing enough to my expenses, so wouldn't help me. I found it difficult to get a part-time job which didn't interfere too much with my studies, and I took whatever was available. That was usually waitressing in hotels or cafés in the area. We were allowed to wear our own clothes, and I quickly found that if I wore tight tops and short skirts, my tips increased considerably.

One day, the manger of one of the smaller hotels where I did some waitressing work, invited me for a drink to discuss a job. He said that he had noticed how popular I was with the customers and he liked my confident, cheerful approach. And my big tits too, I thought to myself.

To his credit, he was very frank about the job. At weekends, he hired out one of his meeting rooms for a card game. It was a private function and he wanted me to act as the waitress. Then it became a bit murky. I would be there until the early hours of the morning, and the men wanted a bit more entertainment than just having drinks served. I tried to keep my face straight as he explained that I would have to dress in a sexy maid's outfit - what a cliché, I thought. The pay would be reasonable, but the tips would be extremely generous.

My humour faded, when the manager gently hinted that although genuine waitressing was involved, the more entertaining I was prepared to be - the greater would be the rewards. When I queried just how far I was expected to go, he assured me that it was entirely up to me. The men were all known to him and nothing would happen to me unless I was agreeable to it.

I was about to decline the offer, when he mentioned the lower level of the sort of money I could earn. I caught my breath. It was more money than I would earn in months of normal part-time work. That old second-hand car that I had set my sights on, suddenly seemed a month or two nearer. "You're on," I told him.

The big day had arrived. I had been issued with a very short black skirt, a little white apron, and a white blouse which was really a size too small for me. With all the buttons done up it was drawn very tightly over my 36B wonderbra. I had been instructed to wear stockings, and since I didn't have a suspender belt, I bought a pair of hold-up black nylons.

As I looked at my reflection in the mirror in my boarding house, I realised that I certainly looked like the traditional sexy French maid. I had only to bend slightly to reveal my bare upper thighs and white panties, which were reasonably modest. A pair of black shoes with three-inch heels which I had not worn very often completed my getup. At least I knew that I would have plenty of chances to sit down to rest my feet.

I wore a coat over my outfit for the short bus journey to the hotel. As the usual vibrations from the bus travelled through my groin, I felt a strange mixture of emotions. Naturally, I was rather apprehensive as to what awaited me, and yet I found that I was definitely horny. Some of my favourite masturbatory fantasies began to flit through my mind. And yet, I was still relatively inexperienced sexually. Was I ready for what I might be asked to do?

Well I had never been one to shrink a challenge, and my confidence in my power over men was beginning to develop. It's easy money, I tried to convince myself - not wholly successfully. My final thought as I walked into the hotel was that I would play it by ear and see how far I wanted to go. At that point, I hadn't a clue how far that was.

I had been told that the clients were well off businessmen who liked to play for high-stakes poker games in privacy. I could see the point in using students like me who would only be in the town for a short while and would never become part of the community to tell tales. I had been to the room earlier in the day and shown the layout of the drinks cabinet and buffet table. Theoretically, my duties would simply be to keep the men topped up with drink and food as required. What else they would want remained to be seen.

I have to admit that my legs and hands were trembling slightly as the manager ushered me into the room and introduced me. He locked the door behind him, after indicating how to unlock it from the inside. The room was softly lit with glowing wall lamps, and the heavy drapes were drawn. A brighter, overhead lamp illuminated a large round card table and several leather armchairs and a sofa completed the furnishings. The drinks bar and food table were in the far corner.

There were six card players of varying ages and appearance around the table with piles of banknotes before each one. I took off my coat, and there was silence, as six pairs of eyes scanned me eagerly in my outfit. I suddenly felt naked. A tall, middle-aged man, with silvery hair rose and approached me. "Good Evening Fiona, my name is Ted. Thank you for coming to look after us this evening. You look lovely." My face reddened and for a second, I almost felt that I should do a little curtsey, to acknowledge his welcome. Instead, I muttered some thanks and headed for the refuge of my working area. As I swayed across the soft carpet on my heels, I could feel eyes following me.

I picked up my pad and started taking orders. The arrangement was that the total drinks bill would be charged to the organiser as part of the room hire, so I didn't have to handle cash. My first unorthodox task was when one of the men asked me, to the sound of chuckles, to undo a couple of buttons on my blouse, handing me a £5 note with a smile. I smiled in return and did as he asked. Of course, now every time I leaned over a table, most of my boobs were on display as well as my panties.

Apart from that, everything was normal as the evening wore on and drinks flowed. Earlier on when I was still nervous, I stooped behind the bar and gulped down a very large gin and tonic. I felt very guilty, but not enough to stop me having another couple later. So I was feeling relaxed and mellow, when after a couple of hours, the card games broke up to allow the men to use the adjoining washroom and have something to eat from the buffet.

A group of the younger men gathered around me and asked the usual questions about my Irish accent, where I was from and so on. Everyone was very friendly and I was beginning to forget that I was dressed very provocatively. Ted, who had spoken to me earlier, took me to one side. Looking intently into my eyes, he asked me how I felt about providing a little entertainment for his friends, to enhance the card games. He added that I would be well rewarded.

Of course, I was prepared for this, but still felt a surge of panic as I asked what he had in mind. Ted explained that the winner of each hand would be entitled to ask me for a forfeit, for which he would pay me from his winnings. When I agreed to give it a try, he smiled delightedly. Taking my arm, he whispered in my ear,

"Don't be afraid to do a bit of haggling, my dear. There is a lot of money floating around and you look very enticing."

While the players returned to their table, a chair was drawn up for me beside it. Soon, with laughs of delight, the first winner eagerly drew a large pile of notes to him.

"Forfeit, forfeit," came the cries from the losers, pointing at the winner. He looked at me for a moment.

"Take off your blouse, please," he asked. I hesitated, and he gathered several notes and rose to show them to me. I took one glance at the amount involved and nodded quickly, hearing them rustle as he put them in the bowl which had been set aside for me. I stood up and found my fingers trembling as I undid the rest of the buttons, and slipped of my blouse, to a little ripple of applause. The low cut of the bra revealed my boobs almost to the nipples, and the wired support pushed them up invitingly.

I was aware of the admiring glances my tits were receiving as I served drinks and then the next forfeit arrived. I knew before he announced it, that it would be my skirt, so I had braced myself for its removal. I kept telling myself that my white panties were more modest than my bikini bottom. However, this wasn't a swimming pool or beach and I was performing for a roomful of men.

Perhaps the drink helped, but I felt more aroused than embarrassed when I wriggled out of the tight skirt and attached apron. I stood in front of them in my bra and panties; my nylon-clad legs tautened by the high heels. There was more applause and various favourable comments. I think it was then that my current exhibitionist tendencies first began. I realised that I was becoming very turned on by the attentions of the men as I moved round the room, and I worried that my increasing wetness would show through the white knickers.

I was still wrestling with myself as to what to allow for the next forfeit, when decision time arrived. The latest winner asked for my bra to come off. I still couldn't make up my mind, and there was silence except for the soft background music while I hesitated. Perhaps the music gave him an idea.

"I'll tell you what," he said. "Keep your bra on, but how about a dance and a kiss instead?" Ted spoke up to rule that if I agreed, the dance would last for three minutes and the kiss for one minute. I watched the winner count out some notes, and I surprised myself, by shaking my head.

"A bit more than that please," I declared in a shaky but firm voice. There was approving laughter,

"You tell him girl," someone called. The man pulled several more notes from his winnings and when I nodded, he rose eagerly to calls of encouragement.

"I'm Bill," he said as he took me in his arms. That simple move was the point of no return for me in what was to be a very sharp rise in the learning curve of my sexual experience.

There was no pretence at dancing. We just stood swaying to the music and Bill pulled me hard into his body, dry-fucking me through my thin panties. He bent his legs and I felt the bulge of his erection pressing against my wet pussy lips, while his hands roamed over my tingling body.

Quite simply, all my sexual demons that had been kept under some sort of control for so long were set free. It was all too much for me - the close presence of the men, the alcoholic buzz in my brain, and the wave of lust that Bill was releasing in my semi-naked body - I surrendered. I stood passively, as he unhooked my bra, and slid it down my arms where they hung at my side. There were whistles of appreciation as my breasts swung free.

He cupped them in each hand, fondling my firm white flesh, and rolled the stiffening nipples between each thumb and forefinger. Then, before I knew what was happening he bent to suck, lick and bite my nipples, sending sparks of pain/pleasure shooting through me. Dimly I heard Ted call, "Time," and Bill raised his head to kiss me. Our teeth clashed when our mouths linked in a wet, slippery kiss, and I felt his tongue search for mine. When his hands went to the waistband of my panties I reached down to grip his wrists, in a last desperate attempt to maintain some control.

An arm came between us and Ted pulled us apart. "Steady," he snapped at the highly excited Bill. "Steady." He looked closely at me.

"Are you all right Fiona?" I was anything but all right. My heart was hammering, my pussy was flooding, and my clit was straining against the gusset of my knickers. As I gasped for breath, Ted gave a signal and the men started to drop high denomination banknotes into my bowl. I gazed in fascination, as it was almost filled. I couldn't begin to calculate how much they were giving me, but I knew that it had to be well beyond what I had ever hoped for.

I will never know if it was the lure of the money, or my lust, which was the deciding factor, but with a very weak smile, and in a choked voice I managed to mutter,

"Yes, I'm fine."

I stood with my legs slightly spread while Ted ran his fingers between my thighs. When he encountered my damp panties, he smiled.

"Good. I'll put your money over there," and he carried the bowl to where I had left my coat. Men gathered excitedly around me and Bill led me to the large sofa where he pulled my panties down. My legs had gone weak and I slumped down on the sofa, leaving my knickers around my ankles. Eager hands reached for me, my panties were removed and I was naked except for my black nylons and stilettos.

My mind kept struggling to balance the different signals that it was receiving. I knew that my behaviour was outrageous by any standards, and yet I had reached a state of sexual excitement that I had never enjoyed before. I was literally quivering with anticipation, and I knew that I was going to cum within seconds of anyone touching my clit. I wanted to know what it would feel like to have those men fucking me. That was my first glimpse of the enormous sexual hunger that I have now come to accept and live with.

In all honesty, I can't remember precise details of the events that night, but they were something like this. Someone leaned over to kiss me and hands fondled my breasts; but when fingers probed at my pussy, I drew up my legs to help. I felt two fingers work into me, and ream rhythmically for a moment. Then a thumb was rolling my swollen clit around and I screamed as my first climax of the night exploded. I bucked and heaved against the fingers as I came, long and hard.

When I opened my eyes again, it was to see a young man kneeling between my legs and aiming a short, but fat cock at my dripping cunt. He rubbed the bulbous head between the lips and onto to my still-throbbing clit, bringing a moan from me. I was ready for as much cock as these men could give me, and they knew it.

"Good girl," he muttered, as he pushed his cock into my slippery slit as far as he could. Within a few seconds, he was pumping steadily back and forth in my pussy. I was slithering on the leather sofa from his movements as sweat broke out all over my body, and hands took turns to squeeze my swollen breasts.

The one inside me had staying power or had drunk a lot for he seemed to go on for ages. He stepped up his pace, pounding furiously and I felt a hand groping for my clit. It found it, just as a hot load shot deep into my clenching cunt. I threw my head back and cried out in utter passion as another orgasm swept through my body. While I lay, still jerking and trembling, the man on top pumped several more times, making sure I got every drop, before slipping his wilting dick out.

Just then, I felt my head being lifted and turned, and I saw Ted kneel in front of me, sporting a long cock that jutted out from his hairy belly. It was meaty and laced with bulging veins. As he slid it into my mouth, I grabbed the fat cock by the base to control it and began to suck voraciously. I was reasonably experienced at giving head at that time, but hadn't learned to deep throat.

From the corner of my eye, I saw one they called Jim climb onto the sofa. He was a well-built man, middle-aged with short brown hair and possessed a very nice-looking cock of about seven inches. He didn't hesitate, but thrust his dick into my flooded pussy in one smooth plunge.

I groaned and whimpered with pleasure as he fucked me with strong, steady strokes, and I found myself rolling my hips to get the full benefit of his thrusts. I felt a pulsing cock being pressed into my free hand and instinctively, I wrapped my fingers around it and began to stroke it. I gurgled incoherently as three cocks worked themselves on my hot young body.

Under the pounding I was receiving from the big cock, I was suddenly hit, without warning, by a rolling, swirling orgasm. I pulled Ted's cock out of my mouth and screamed out, as yet another climax roared through me.

This was all new to me then, and I had always needed at least half an hour before cumming for a second time - and twice had been my maximum. I was beginning to hit what, these days, I call the twilight zone, where my orgasms come at a breakneck pace -- but only in special situations.

Ted pushed his wet cock back into my open mouth and started to hump with increasingly jerky motions as he enjoyed the blowjob. Grasping the back of my head, he began to work my head up and down and I had to hold him back with my fingers around the base of his dick. I was anxious to please him and I could hear my gurgling sounds as I sucked ever more vigorously.

Just as I felt someone else start to enter me, my efforts were rewarded. Ted jerked upwards hard, one final time, then exploded in globs of cum that hit the back of my tongue, and I swallowed as quickly as I could. However, my head was turned to the side, and when Ted withdrew, I felt a small stream of cum escape my lips and dribble down my chin.

After that, I went into some kind of delirium for a while, and it is all a confused blur of cocks and hands pleasuring me while I writhed and moaned. Eventually, I was brought out of it by a sharp pang of pain as someone tried to stick his cock in my ass.

I hadn't experienced anal at that time, and wasn't prepared to allow it. I reached down and pushed the invading cock away.

"No, not there," I grunted.

"She's fucking flooded," complained the man on top of me.

Ted intervened. "She said no - stick it in her cunt like the rest of us," he ordered. I touched my gaping pussy. It was indeed leaking copiously and I realised that there was a sticky pool under my buttocks. My fingers were knocked aside, the man drilled his cock into my steaming cunt and with a long groan, he pushed deep into me.

He leant over me and desperately thrust his cock around my flooded walls. In that position, the pronounced ridge that ran the length of his shaft touched my clit, and I raised my thighs to get closer. There was so much white cream in me that his cock squelched with each entry and I could feel a foaming goo run down my thighs while I trembled and jerked as my next orgasm reached a crescendo.

I think that was the last fuck, and I might have dozed off in exhaustion, for my next distinct memory is of Ted standing over me, fully clothed, as were the other men. He handed me my clothes and a wad of banknotes. "We're going now Fiona. Thank you very much. You can use the washroom and let yourself out. We hope to see you again - you were fantastic."

In the taxi ride home, I counted the money unbelievingly. I had never held so much money in my hand before. I now had enough to buy the car! Despite the shiny new cars I have owned since, that old Ford will always have very special memories for me, as will my very first gangbang. Of course, the guilt and a very aching pussy came the following day. But I quickly got over both. However, I never did attend another of those card games. A girl has to have some pride!