Waitress Serves Five Servicemen

How things have changed in the twenty plus years since I was in my early twenties. Looking back I thought I knew it all but in fact was very naïve. What happened back then happened in a very different environment to that that exists now.

I was a waitress in a pub/restaurant. We were encouraged to dress with a level of provocativeness that would now be frowned upon. I loved being able to dress this way and particularly loved the attention that I received. We did have a uniform (not paid for by the restaurant) of close fitting blouses tucked into short black skirts. Under this we wore tights or stockings. As the stockings were always more popular with the punters, sorry diners, these were encouraged. I was delighted to go for this option particularly as the tips were much bigger.

The restaurant was made up of a number of mainly small dining areas and a waitress was assigned to one of the smaller areas or two did the largest area. I am sure the restaurant owner always assigned me to the one area that was upstairs because this offered a couple of tables a clear view as I climbed the stairs. I used to joke with the other girls that I couldn't understand why these tables were nearly always full. There were two table upstairs each able to take six diners so other than needing to climb the stairs all evening long it was the easy option.

Once a month there was a group of men who met and always booked a table upstairs. On these evenings the owner did not take bookings for the other table upstairs. I think that they had all served in a military unit together and this was their way of keeping in touch. The owner was also ex-military. They were around mid-thirties to early forties. Like many of the diners they were always very familiar with me and flirting seemed to be expected. In today's society this would be frowned upon but back then it was not. Don't get the wrong impression I was not only not upset by it but I loved it. I started to look forward to the evening serving them their food and receiving their attention. One of the men (Ben) seemed to take the lead. He was good looking, energetic and lively with eyes that sparkled. He reminded me of my dad (writing that sounds so wrong).

Each time they met things got more intimate. I had been introduced to them all but they didn't use these names much preferring to each other by their nicknames. They knew my name and the flirting did become a little stronger but I loved this. I was the center of attention and I looked forward to it. I am so embarrassed now to admit that I chose my bra, stockings and even my panties when I knew I would be serving 'the troops' as all the staff called them. I had started to make sure that my blouse was open far enough to ensure my cleavage was visible at all times. With the bra that I started to wear when with them if I leant forward the low cut nature would provide them with a significant eyeful. This did not go unnoticed by the men round the table. The teasing and flirting did now include friendly comments about my substantial boobs. At the time I was not uncomfortable about this. I certainly would be now.

It was completely my fault that things escalated. I had made sure that I when reaching for things on their table I bent just enough to ensure that my stocking tops were visible. This also meant that those sitting opposite got a view down my blouse and I am sure down my bra at times. If I was doing this now a days I know the names I would be called but I was never aware at that time of being referred to in those terms. I was loving the attention and I think they were loving the views. On this particular day I must have stretched a little further. There was a sharp intake of breath from behind me and at the same time my right nipple made a bid for freedom. The bra I wore for these evenings was a good fit but was very low cut and my nipple had worked its way out of its constraints. In the process it had become pinched and I became fully aware that it was no longer covered. It might help if I explain that my nipples are always thick and very sensitive. When they become erect they become long as well. The customer opposite exclaimed without saying what was going on but the men alongside him were soon focused on my nipple that was very exposed. One of the men said something like,

"You don't get many of them to the pound, it could have someone's eye out young lady."

As I straightened up next to Ben he spotted my predicament immediately. I stood routed to the spot not quite sure what to do. I couldn't make myself return my errant nipple to its covering and stood still feeling very silly. With a friendly smile Ben said,

"Let me help you; you seem to have a wardrobe malfunction."

Without saying anything else he slid one hand done my blouse found my now fully erect nipple and returned it to its covering. The world stopped for a couple of seconds and there was no noise until his mates started to praise him. The contact with my nipple had been electrifying. Never before or since has contact with a nipple been so erotic. Both nipples were now fully erect and I was gutted that the briefest of sexual encounters was over. I thought his mates were going to clap but it didn't go quite that far. I looked up into his friendly eyes and even thanked him. I probably only specifically remember three of my most memorable orgasms but that brief contact still fills me with sexual energy whenever I recall it. Readers must think that this was very tame as nothing more happened that evening with the customers. I did however have one of the three orgasms I do remember that evening. When they left, leaving me a bigger tip than usual, I was straight into the staff toilet and masturbated to a monumental cum. I used one hand between my legs but the other to pinch my right nipple with crushing force.

The next time the group met I was very excited but also terrified. Be clear I was no innocent virgin but what had happened the month before was frighteningly exciting and erotic. I was so frightened that I started to ask a colleague to swap which tables we served that evening. Before I actual said what I was going to my body flooded with adrenaline or something. The vision of being bent across the table with a nipple exposed flooded my mind. I needed that same excitement again.

The atmosphere around the table when I asked to take their drinks order was one of nervous excitement. When I took Ben's order he asked me quietly whether I was okay serving the table. I wanted to tell him that I was sexually excited by being there but just settled on saying that I was fine. The banter seemed a little more open than previously but I was frustrated that they didn't mention the nipple incident and I thought that was the end of it. When collecting the plates from their main courses I deliberately lent at full stretch across the table while standing between Ben and the smallest of his mates. I was determined to show Ben specifically not only the tops of my suspenders but well beyond. I tried to wriggle so that my nipples that were just held at the very top of my bra would be freed up but failed.

I happily stayed in this position pretending to not get hold of the plate but challenging, with my eyes, the men opposite to look down my blouse. I was successful to a man. I couldn't pretend that standing in this position any longer was not deliberate but just as I started to lift my upper body a hand slid up the back of my leg. As with the nipple contact the level of excitement this caused me was ridiculous. Something gave and I was shocked that I thought I had peed myself. It wasn't that much less scary when I realized my pussy had been flooded with sexual arousal. The hand travelled on up beyond the top of my suspenders until it slid under the elastic of my panties. It did not stop until the large hand was covering the whole of my right cheek.

"You can either stay where you are and let us all enjoy the view or you can get up and ask another member of staff to serve our sweets. If you stay there I will ask Pete to release your gorgeous nips so that we can enjoy seeing them and you can enjoy showing them off."

I thought about protesting but just managed to be honest enough with myself to stay where I was. Pete didn't need to be asked twice and was soon releasing my dangling boobs from my bra. It wasn't either very comfortable or very dignified, as he didn't unclip the bra strap. It did somehow feel even more dirty.

(I must just stop to give men a little advice; if you want to excite a woman's boobs and nipples do so when they are dangling, nothing compares. If you women disagree please put a comment at the bottom of this story.)

I forgot the hand on my bottom as hands found my boobs and more excitingly my rock-hard super-sensitive nipples. Ben was standing next to me by the time my panties reached my knees and his fingers found my pussy and clit. He bent and put his mouth to my ear and whispered.

"I apologize if I am reading you wrongly. There are three options; firstly we all apologize profusely and you stand up, secondly I bring you to orgasm as your body is screaming for, or thirdly you get our sweets and coffee and come back up and let at least two of us fuck you senseless. Which will it be Angie?"

He was asking me to ask them to fuck me. Yes I wanted to orgasm but option two was just not enough for me and I knew it. I suspected Ben knew it too. As I didn't move everyone knew option one was not being considered by me. The animal excitement of what was being done to my body threatened to achieve option two without further consideration. My reply was almost with disappointment when I said,

"I will go and get your sweets and coffee. Please order the cold sweets as the hot ones take minutes to prepare."

This comment went down a storm and laughing they all ordered cold puddings and all declined the coffee. My bra and panties were both removed before I was allowed to leave the room. I walked very gingerly down the open sided stairs as I did not want my excited pussy to be on display. My boobs and nipples were much more of a problem as without my bra my erect nipples were very prominent. I was fine while I could hide them with a full tray but in the kitchen was a problem. My best friend spotted that I had a problem and asked me if I needed help. She could see I was braless. I nearly told her what was going on but was afraid it could ruin everything. She said she would come up with me to deliver the food as she put it "I could help you if you are feeling rather outnumbered."

I was certain she knew that thing had turned sexual up there but surely she could not know what I was returning to. I thanked her for her help and she covered my movements until I had a tray full of deserts to cover my embarrassment. It seemed harder to climb the stairs modestly but I did my best with limited success. Old Mr. Hardy copped his best eyeful ever even allowing for his fading vision. When only he had a view I bent right over on the pretext of needing to get a better grip of the tray and gave him an opened legged view of everything under my pulled up skirt. From his expression it was clear his vision had not faded too much yet. Rereading this I am judging myself as much as I am sure the readers will be.

By the time I walked through the door my pussy was flooded again. I don't know if I had expected all five men to be standing naked when I returned but finding them seated as they had been earlier, fully dressed and discussing things that I don't think included me was really disappointing. As I served each one their sweets I completely unnecessarily bent right forward and positively encouraged them to explore between my legs. Half way round the table I disposed of my blouse but left my skirt on because it just felt really dirty to do so. I served Ben last and his fingering of my pussy had me desperate for the main course. When he stood up he directed me to lie on my back on the table where an area had been cleared. The table was not big and some part of my anatomy could be easily reached by each of the men.

The one thing above all that I learned from that evening is that anticipation can be every bit as exciting as the event. No I am not going to write that the sex was not exciting, as it was breathtaking, but I now know to enjoy the expectation as I had that evening. Lying on that table I was coiled like a spring.

Maybe they had been talking about me as I walked in, as they seemed to know who would do what straightaway. My nipples were quickly smeared with cheesecake by Fred (always referred to as Foxy) who took his time in doing so. This was removed by Smithy's mouth. I swear that if he had eaten a whole serving of cheesecake I would have orgasmed from his mouth alone. When ice cream was spooned onto my hot pussy I was less impressed. The spoon even pushed the fast melting sweet into my pussy. The removal of this was much more enjoyable than the application. The mouth of AA was not rushed and visited my anus as well as my pussy and clit. The warmth as my clit was turned from near freezing to hot and swollen was wonderful. I was very embarrassed that I could not hide how arousing I found the licking of my tight anus. No man or woman had touched me back there and it felt electric. Again I was racing towards an orgasm that I am sure owed as much to the whole situation as it did to the specific licking and sucking that seemed so skillful.

I was so ready for the main course I was close to frustrated tears. I was aware that neither Ben nor Flapper had touched me since I had served their sweets. It then dawned on me that Ben had referred to me being fucked by at least two of them. I was desperate to be fucked but was nervous of being gangbanged, something I thought only happened in porn films.

Ben took control of me and the whole situation. He moved me so that, still on my back, I was on the edge of the table in front of him. He lifted my legs up to his shoulders before looking into my eyes. They clearly confirmed what he needed confirming before he slipped his trousers down and entered me slowly. Was it being watched, what he was doing or was it the crippling anticipation that made this penetration like none I had experienced before? All that mattered at that moment was that his prick felt beautiful. He fully penetrated with an ease I had never experienced. This was not because he was small, as he seemed to my inexperienced eye a good size. His eyes remained friendly and had this been happening in my bed with just the two of us I would have described it us gentle lovemaking.

It was not happening within a vacuum and this was turning gentle lovemaking into a sexual experience that most women will never have the pleasure of enjoying. It is an experience that I will remember for the rest of my life. This was both lovemaking and something that I was feeling as so much more. Never in my life had I wanted two such conflicting sexual outcomes. Firstly I wanted what this man was doing to me to last forever; secondly I wanted to cum immediately. I didn't have any choice in the matter as an orgasm that I had no warning of took total control. I wish I could do it justice by describing it but no words would be enough. I came and came and carried on cumming until my mind was cream cheese. I know I was saying something and making a lot of noise but I have no idea whether any of it was coherent.

Whatever happened Ben was beside himself with excitement and praise. It was him that for some reason I had wanted to please. I wasn't however finished for the evening. There was one man left and it was obvious that he had won whatever the bidding process was and I was his prize. I couldn't remember what his real name was but like all of them he was always referred to by his nickname, 'Flapper'. Ben (or Sarge as they always called him) turned me over onto my knees in the middle of the table. My skirt was finally removed. When he started to entered me I was uncertain that I was up for any further sexual pleasure. There was a hushed silence as his prick stretched my willing pussy to its limit. I was shocked at how tight I felt given that I had just had an extraordinary orgasm only a minute earlier. It quickly became obvious to me that Flapper was built like no man I had known. It was some time before he eventually bottomed out as his balls hit my clit. By this time despite the discomfort of being stretched like never before I was certain that I wanted what I could only assume was his sizeable prick.

In this position my boobs were dangling and were very quickly caressed by hands from every direction. This was no gentle fucking I was being fucked vigorously from behind while my excited nipples were being partly caressed and partly tortured. I had no idea which of these was better. I had not seen his prick before it had pushed into my surprisingly tight pussy but I knew it had great girth. When fingers found my clit I was climbing the steep slope to orgasm at an alarming speed. I was soon at the point when nothing would stop the climb to total oblivion, total abandon and the purest of pleasures. This orgasm was short but powerful as the large prick in my pussy emptied itself deep inside me.

As his softening cock slid out of me there was a round of applause. I was a little surprised by this but felt compelled to turn and see the prick that had felt so good. It was soft but even flaccid it was huge. I couldn't believe I had just taken all of this monster in its erect state.

"Angie we were worried that you would not be able to take Flapper's huge cock but you not only took it but seemed to be loving it. You are such a slip of a thing, are you OK?"

I had no idea how to answer Ben. I didn't want to admit the truth that I had just had the most amazing sexual experience of my life. I did confirm that I was fine and that I had enjoyed both orgasms. Any concern in the room was now satisfied. One of the other men stepped forward but Ben held up his hand in a gesture that stopped him moving forward.

"I think that Angie has had quite enough for one evening. No man should ever follow Flapper in any case."

The other man put forward a protest but Ben waved it away. Ben then repeated that the fun was over for the evening.

"I hope that Angie will agree to serving us food in a month's time. I can only hope that she might agree to serve herself up to others who have not sampled her delights quite as fully as they would have liked to tonight."

I was still buzzing but was very relieved that another cock would not penetrate my now tender pussy. I had been concerned that I would be required to entertain all five men with at least my hands or my mouth. Each man seemed to be compelled to agree with Ben. There was a chorus of,

"Ok Sarge."

They were clearly not going to challenge the man that was in charge of them.

Within five minutes all five men were gone but not before Ben had made sure I was ok. My waitress friend (Sandy) also wanted to ensure that I was ok. She made it clear that she had no doubt that things had got sexual and wanted the full details. I didn't lie to her but said just enough that with a promise of full details when the chance arose she stopped questioning me.

She was not only persistent until I told her nearly all of the truth but badgered me until I promised her that she could serve the coffee the next time I served the troops. I will write about that evening at some time in the future.