tagExhibitionist & VoyeurLadies must be Entertained

Ladies must be Entertained


It should've been a straightforward night. My second time working as a server for the Stephenson Catering Company.

I was 18 and this was my first time job. It wasn't what I wanted to do for the rest of my life but it was a start and to be earning my own money was a source of pride for me.

The first night we'd been at a 10 year anniversary party for an uptown law firm and it had been pretty uneventful.

I wandered around with trays of cocktails and horderves then helped the rest of the crew clean up at the end.

A week later my second day on the job would prove to be far more memorable.

Linda, my boss, told me to show up at an address in Shereton Drive at 6pm for what she described as a 'small gathering for some well to do ladies.'

As instructed, and wearing my uniform consisting of black pants and white button up shirt with a black tie, I arrived shortly before 6pm.

Linda was already there and I helped unload the van and set up for the night.

The house was large with high ceilings and some expensive looking artwork on the walls.

Strangely, given my lack of experience, I seemed to be the only server there but I brushed that off thinking Linda must have confidence in me and it was probably only a small party.

The event got underway about an hour after I got there and at first it was much like the first night.

I handed out drinks then took a few trays of food out to a large table that was apparently going to act as a kind of buffet bar for the night.

Hosting the party was the homeowner, Sheila Staples. Aged in her 50s, she had dark hair with a hint of grey and was dressed smartly in a white business style jacket and matching skirt.

Besides Mrs Staples there were 15 other guests. All were woman in their 50s or early 60s and had similar appearances to the hostess.

About 45 minutes into the party Linda called me through to the kitchen and to my surprise said she was leaving for a couple of hours.

'All the food's sorted and there's nothing more for me to do,' she said.

'Are you sure?' I asked nervously, 'It's only my second night remember?'

'You'll be fine,' Linda replied putting her hand on my arm reassuringly. And with that she was gone.

Slightly puzzled by this turn of events, I made my way back into the room where the party was now in full swing.

The ladies seemed to be enjoying themselves and they were certainly enjoying the booze!

I stood near the buffet table trying to look busy while I figured out what I should do when Mrs Staples approached me.

'Tim isn't it?' she asked.

'Yes Mrs Staples,' I replied.

'Please call me Sheila,' she said, 'We're very informal here.'

'Ok,' I said.

'Now Tim,' Mrs Staples said with a hint of grin, 'With that in mind I really do think you're a tad too formally dressed.'

Somewhat taken aback I didn't know what to say but before I could open my mouth Mrs Staples grabbed my tie and undid it.

Pulling the garment from my neck, she smiled. 'That's better,' she said, 'Less formal and I'm sure more comfortable for you Tim?'

Stunned I mumbled, 'Yes, yes I guess so.'

The next thing I knew, Mrs Staples had taken my hand and was leading me into the center of the room.

'Can I have everyone's attention please?' she said raising her voice to be heard above the murmur of the various conversations which were taking place.

'This is Tim our server and, if we're good girls, our entertainment,' she said.

The women were all staring at me and a ripple of applause broke out.

I had no idea what was going on and was beginning to grow very nervous.

'Entertainment?' I asked.

'Why yes Tim,' Mrs Staples replied, 'Linda always sends us the nicest young men to perk up our social gatherings.'

'She never said anything to me about entertainment,' I said, 'I'm just a server not a singer or comedian or anything like that.'

Mrs Staples chuckled. 'Oh Tim you are a sweet thing,' she said, 'It's more adult entertainment we're wanting.'

I gulped and felt a knot growing in my stomach as I began to realize I'd been set up by Linda.

'I think there's been some sort of mistake here Mrs Staples...I mean Sheila,' I said.

'Oh,' the hostess replied with a wry smile, 'What sort of mistake?'

'I'm just here to serve food and clean up,' I said.

'Now, now Tim,' Mrs Staples replied, 'That won't do.'

The women appeared to have come much closer to me by this point and were all checking me out as if I were a piece of prime meat.

Without saying another word, Mrs Staples pulled me towards her and started undoing my shirt buttons.

'Let me help you,' she said, 'I can see you're a little nervous.'

I started to pull away but a couple of the other guests grabbed my arms and the next thing I knew my shirt was off.

The women let out a cheer. Mrs Staples was on her knees now undoing my pants.

She tugged them down to my ankles and, with the help of another guest, removed my shoes and finished taking off my pants which quickly disappeared into the crowd.

There was more cheering and a few remarks thrown out by the women as I stood there in nothing but my shorts.

The group moved even closer around me like a baying pack of hungry wolves.

'Now who wants to see his cock?' Mrs Staples yelled.

The women cheered wildly and I have to admit at this point I was becoming a bit aroused by all this attention.

Responding to the cheers of her guests, Mrs Staples grabbed the waistband of my shorts.

My dick stiffened a little more as she slowly began pulling them down.

As I looked around the room all I could see were 15 pairs of eyes staring at my groin in anticipation of my hardening cock being revealed.

My shorts were down to the top of my pelvis and then with a quick pull, Mrs Staples yanked them down and my dick sprang free.

Up went the loudest cheer of the night. I stepped out of my shorts that had been moved to my ankles and then watched as my last item of clothing was thrown into the crowd of lustful women.

Suddenly everyone seemed to be holding a cellphone and were obviously taking pictures of me as I stood there naked.

My arms were still being held so I could do nothing to cover myself as the women clicked away.

'What should we do now?' Mrs Staples said smiling broadly.

Immediately the guests responded in unison with a loud cry of 'make him cum!'

Not for the first time that night I was stunned but by this stage I was resigned to the fact that I could do nothing to stop whatever was going to happen.

'Well I always aim to please my guests,' Mrs Staples said gleefully.

She took my dick, which was now rock hard, in her left hand while grabbing my balls in the palm of her right hand.

Her hands felt soft and arousingly cool on my private parts.

She started tugging my cock gently and massaging my balls.

I looked around again and just as before all eyes were firmly fixed on my groin.

Some of the women had put away their phones but others were still trained on me no doubt filiming and waiting for the inevitable cum shot.

'Has everyone got a good view?' Mrs Staples enquired and hearing no complaints she tightened her grip on my shaft quickening the pace of her strokes.

'I think we need some lubricant,' Mrs Staples said as she continued to rhythmically pull on my cock.

With that one of the women stepped forward eagerly and, as Mrs Staples briefly paused her tugging, spat on my dick.

'Anyone else want to help this dirty boy reach his climax?' Mrs Staples said.

Another guest came forward and delivered some phelm on my dick.

Mrs Staples tugged harder as a third woman came forward but this time instead of spitting on my cock she bent down and licked it.

At this point I was really close to cumming and Mrs Staples could obviously tell.

'Ok girls that'll have to do I think it's time,' she announced.

Another cheer went up and a chant began 'cum, cum, cum!'

The women started to a slow hand clap as Mrs Staples jerked my dick faster and faster.

The clapping speeded up and her strokes followed suit as I felt the cum begin to make it's way from my balls and up my shaft.

As the clapping reached a feverish crescendo, Mrs Staples squeezed and yanked my cock harder than ever before and with that I exploded.

The women cheered once more as I fired streams of thick, sticky white cum onto Mrs Staples' face and jacket.

As the last jet shot out the hostess licked some of my cum off her face then took my cockhead in her mouth and sucked off the final few drops.

When she'd finished she stood up and the group of women began to move away and resume their conversations.

'Good job Tim,' said Mrs Staples, 'And there was you thinking you couldn't entertain us.'

She chuckled and used a tissue from her pocket to clean off the cum I'd just sprayed on her jacket.

'Now Tim,' she continued, 'I suggest you find your clothes then check on the buffet. I've eaten but some of the girls might still have an appetite.'

She walked off and, still shocked by all that had gone on, I did as I was told.

The rest of fhe night was as if nothig unusual had happened.

Having located my clothing and dressed I served more drinks and when Linda returned we tidied up as the party wound down.

As we left the house at the end of the night, Linda handed me 100 dollars which she said was from Mrs Staples for me providing 'great service.'

Linda and I never spoke about what had gone on although I'm sure she knew and if she didn't there'd be plenty of video footage of my experience circulating a certain section of the town's society.

I'm still working for the Stephenson Catering Company but the job has been a lot more routine since that night at the Staples' residence.

Report Story

bygwriter77© 4 comments/ 17332 views/ 11 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartRockoftheWoods, heathrowinneo and 9 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous10/16/17

Arousing story!

I like your story! It is really arousing to stand in front of lots of clothed women, being stripped and photographed! You never know what the women will do with the photographs. That makes the experiencemore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous10/09/17

An arousing story!

I love your story. I think I wouldn't dare to go to such an event. But if it happens to me.... I think the most arousing and humiliating event was being photographed and filmed naked. If I was the waitermore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous10/07/17

A great story!

Thank you for posting. Five stars.

p.s. To the Anonymous who left the long comment: you should turn this into a story and submit it -- you have the bones of a very sexy tale here.

Go for it!

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous10/06/17

Thank you. This is true. I was asked by my aunt to serve drinks and some food at a party for 9 of her female friends. I agreed, I was 24, when I arrived they were all older, over 50, well dressed, includingmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 4 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: