Messy Jessy

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Jess is the stag party entertainment.
4.9k words
4.12
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Welcome dear reader and thank you for taking the time to read this story. My first on this website.

This story is based on an ongoing conversation I have with a girl called Jess. She is fast becoming my muse. A delightful 20 something female with an infectious smile and a dirty mind. She recently discovered her inner slut. This story is dedicated to her and her continuing exploration.

Jess is 5'7", UK size 10 dress, 32D tits, brown hair and eyes, a cute face and firm body that is built for using.

So, to the story...

"What you are doing on Friday night, slut?" you heard my question before you had time to answer as you picked up my phone call. It was Tuesday afternoon. You were working from home, and it was quiet. We had been messaging throughout the morning and you had been desperate for my attention. I teased you by delaying my replies so your need for me was strong.

"Erm..Hello Sir, this Friday? Well, I was supposed to be going out with my boyfriend, why Sir?"

"Cancel your plans I need your slutty body for a little something Friday night. You will love it more than any night out with your boyfriend. Message me when you want details." And with that I hung up.

Your mind was in a daze at this point. Your body, on hearing my voice and calling you slut, immediately responded and you felt that familiar tingle in your pussy, your nipples hardening.

'No playing or cumming from now until Friday either, slut, I know you want to have a sly play after my call. Sir' You bit your bottom lip then pouted as you read my text. How does he know me soo fucking well! You thought as you carried on working trying to distract yourself.

After a long afternoon you finally called it a day and logged out. Slipping your shoes on, you grabbed your keys and bag and headed out to pick up your other half. The journey there and back was fairly quiet apart from the usual pleasantries. On arriving home, you started to get dinner ready. However, your curiosity kept drawing you to your phone.

You wanted more details on Friday, you wanted to know what was going to happen. Shaking your head, you smiled. Sir and his mind games, he always knows how to reel me in! Dinner was soon cooked and served. You and your man talked about the day and what the rest of the week held. Spotting an opportunity to mention Friday, you took a breath and started talking.

Your boyfriend and you had agreed to go out on Friday for a date night. It was your idea initially, trying to get a spark back into your relationship. Luckily, as you were talking about a possibly rearranging it for another night, your boyfriend mentioned he had been invited out with some of his friends. You enthusiastically encouraged it, mentioning you might be out on Friday with the girls from work. Both happy with the outcome you continued with your evening.

Eventually your curiosity got too much, and you messaged me.

'Sir, tell me more about Friday, pleeeeeaassseeee!!! I need to know what you have planned! pleeease I promise to be good!'

'Slut, well you lasted longer than I thought. Maybe you were busy. I knew you would fold soon enough!'

You blushed as you read my reply. 'I have a friend that is getting married soon and the entertainment has been cancelled due to illness so they asked if I knew of anyone who could fill in. Obviously, I thought of you, slut' You blushed again, eyes widening this time, followed by a grin. Then the realisation that, at the mention of me thinking about you and needing you for entertainment, had you instantly excited confirming that you really were a needy attention seeking whore.

More questions from you followed, as always, I gave vague answers just to keep you on edge. By the time you went to bed you pretty much knew I was whoring you out to the stag and his mates. I went to touch your aching wet pussy but then remembered what I had told you. Sighing heavily, you removed your hand away from your crotch and tried to get some sleep.

Tuesday led into Wednesday. More teasing from me all day. Your need for my attention had you reading all my messages and replying. This only stoked your arousal. Wednesday night had you desperate to touch yourself. You tried anything to distract your mind from wandering to what Friday night would bring. Another fitful night of sleep. Wednesday into Thursday. You managed to avoid reading my messages until 10:30.

After just reading the first two your mind was once again in the gutter, your pussy craving to be touched as it slowly dampened your knickers. You replied and it opened the flood gates. Literally. Again, I teased and tormented you with my stories, potential Friday night scenarios and my verbal humiliation. You lapped it all up like a thirsty puppy. Thursday evening had you rubbing your thighs together so much they were red by the time you went to bed. Not that you could sleep. Friday loomed ever closer, promising to finally give you release.

'Morning slut, this is the only message you will receive from me until 18:00. When I will message you with instructions for this evening. Before you ask, the reason I am not messaging you until the time stated is because I want you horny wet and desperate for attention. Have a great day at work. Try and keep your mind out of the gutter please you pathetically useless cum dump. Sir'

You read this message at 07:00. Eleven hours without contact. You nearly cried. Then your need to be denied realised in your head and you moaned out as your pussy twitched. Fuck! He knew exactly how to treat me! Damn him! You thought, shaking your head and smiling. You managed to drag your sorry ass out of bed and get ready for work. At least you were working from home.

Not surprisingly the day seemed to go on forever! Even though you knew I wouldn't contact you until 18:00 you still kept checking your phone on the off chance I had caved and messaged you. No such luck. As the day continued your need for my attention, any attention, increased to embarrassing levels. Only matched by the embarrassingly wet knickers you were wearing. Even the hardness of your aching nipples was apparent.

Finally, after a tortuous day, picking up your boyfriend, feeding him and watching him get ready before heading out, you sat on your sofa clock watching until 18:00....seven minutes to go.....could this day go any fucking slower! You screamed in your head. Even deep breathing did not help. Nothing helped. Only getting my message would fucking help.

'Evening slut, grab a shower, do your usual girly stuff, hair plaited into two plaits, so the gents have something to hold on to, make up slutty, obviously, then put on your black lace bra and thong and your buttoned up dress, finish off with the black patent heels. I want you looking like a conservative vicar's wife. Be ready by 19:30. I will be outside in my car.' That was all I wrote.

You shook your head. Detailed. Precise. Direct. Very Sir. You giggled at the vicar's wife comment. Knowing full well that opportunity had long gone. Following my instructions to the letter, smiling at how uncommon it was for you to actually follow instructions, you soon found yourself ready and primed by 19:25. Primed indeed. You'd been primed since Tuesday fucking afternoon!!

You swayed down the walkway to my car. You couldn't help swinging your hips. It had become a natural progression as you embraced your inner slut. Getting into the car I looked you up and down. Smiling appreciatively. I leaned in for a kiss and you accepted it willingly. You felt your whole body tingle at my touch.

As I drove, we chatted happily about your day and me denying you. We both laughed at this. Acknowledging just how far our dynamic had come since we first met. You glowed from within as I gave you my attention. Something you could never get enough of. You relaxed into the seat feeling at ease if somewhat horny still. After a short drive we arrived at a hotel. I pulled into the carpark and turned off the engine. I turned to you.

"Right then, slut. Its showtime. I will walk you in and introduce you. Then I will lead you to the stag. He will be the man sitting on the chair in the middle of the room blindfolded with his hands tied behind his back" you raised your eyebrow and pouted "Yeah yeah don't get any ideas or be jealous, concentrate! I will put you in the same position tomorrow, if you are good".

"Now, where was i? oh yeah, you will perform a strip tease to whatever music they put on. You will strip naked. Then you will kneel in front of him and take out his cock and give him the sloppiest wettest blow job you can. Then once that is over, you are free to get up close and personal with the rest of them. And when I say 'free to get up close and personal' you will get up close and personal with all of them. Understood?" You nod and smile.

"Any questions?" You thought for a moment. "You will be there won't you Sir?" I looked into your eyes, noticing a hint of fear. Pulling your face into me I whispered "I am always here. I will be in the room making sure it all goes well. Any problems and I will sort them. No one will hurt you and if I get a whiff of malice off any of them, I will make sure they know full well that they are not welcome. Understood?" you gave me a big beam then kissed me.

I got out of the car, walked to your side, opened the door, took your hand and led you into the hotel lobby.

I walked us to the eating area at the far end and we sat on a couple of stools to the left giving us a view of the lobby and the full length of the bar. The hotel was high end and was tastefully decorated.

I ordered us drinks. "I thought it best to settle your nerves before going to the room" You smiled. I called over the young lady serving, and she dealt with my order. I watched her until we had our drinks then turned to you. You were frowning playfully "What, my sweet fuck doll? You know I like to tease you!" we both laughed and took a sip of our drinks.

You looked around at the place. We sat people watching, passing the odd comment to each other as we drank. Soon it was time to go. I walked us to the lift, again taking your hand in mine. Once in the lift I pressed the button for the Penthouse suite.

Then as soon as the doors shut. I pinned you against the wall by your throat and kissed you deeply. You kissed me back. I slid my hand up your dress and rubbed your soaking wet pussy through your knickers. You moaned at my touch. Edging you whilst floor after floor passed. I let go and stood back. You stood there panting.

The lift stopped, the doors opened, and I led us into a long corridor. We turned right and headed to the door at the end. I knocked twice and it was immediately opened by a big bruiser of a man in a black suit. He smiled at me and let us in.

The place was palatial. A main room with a kitchen to the side and a hallway leading to bedrooms. The room suddenly went quiet as we walked in and stood still. All eyes looking at you. You immediately felt the mood, thick with anticipation. You shuddered. There were about 15 men of various ages and sizes.

You spied the stag tied to the chair as I had told you. Taking control of the room I began to speak.

"Good evening gentlemen, Apologies for the delay, however, let me introduce you to messy Jessy, my slut. She is your entertainment for this auspicious occasion!" I led you to the centre of the room and stood you next to the stag. The men cheered and hollered. You did a curtsy and giggled. I continued.

"As you know, Andy here is due to get married to Emily soon, after ten years together he has decided to make an honest woman of her!" again the room cheered and hollered. "As this is your last night of freedom before you are truly pussy whipped, I have a little gift for you. Then if your friends here are interested, the gift will be extended to them too" Again more hollers, you blush, feeling the men undressing you with their eyes. This in turn had the desired effect on you.

"So, just a few ground rules, gents, if I may. This slut belongs to me. You touch her in any way I deem inappropriate, and I will get Gary and Keith here to throw you out" everyone looked over at the two man mountains by the door. They both smiled and nodded. "Glad you understand. My final point before we can get started is the payment due. As Andy is the stag, he will not pay. As for the rest of you, kindly drop your 50 pence pieces in the jar on the table over there" I pointed to the coffee table by the window.

You blushed at being whored out for 50p. He always knows how to ramp things up. Such a clever Sir! You thought. As predicted, for the next few moments all we could hear was the chink of the silver coins dropping into the glass jar.

Suddenly the music started, I kissed you once more then told you to get to work, spanking your ass as I moved to stand with Gary and Keith. You started swaying to the music as the men circled you. The atmosphere was electric, and you fed off it. You soon relaxed and fell into a rhythm.

As you danced around the stag you started undoing your buttons, alternating between the top and the bottom. The men lapped it up shouting "get it off, get it off!" you loved the attention and you grinned at them. With the last button undone you teasingly showed your shoulders and opened your dress flashing your admirers. More cheering and hollering. You dropped the dress to the floor in dramatic fashion leaving you in your heels and sexy underwear.

The bra next, slipping off each strap, then turning away from prying eyes and unclipping it at the back. Holding it in place you turned back around then pulled it away, exposing your tits to them all. More comments and cheers "Fuck me look at her tits" "those nipples need chewing" "what a shameless slut". You took the bra and draped it over the stag's head. Then without missing a beat, you turned your back again.

You slid your thumbs in the waist band of your now sodden knickers at your hips, bent over at the waist and slowly teasingly pulled them over your ass and down your legs. Stepping out of them before opening your legs a little and pulling your ass cheeks apart exposing your pussy and puckered starfish. More cheers! "shit, she is soaking" "fucking whore loves it" "Best 50p I ever spent!".

You picked up the knickers, walked over to one of the men watching and pushed them into his mouth. He moaned appreciatively then removed them "She has one sweet pussy, boys!" he shouted. You turned, dropped to your knees then crawled over to Andy. Who up until now could only hear what was going on.

You kneeled in front of him, leaned up and removed the blindfold. He blinked and then grinned as he checked you out. "Fuck me lads, look at her!" You smiled at him then dropped into his lap. You undid his belt, button and zip in short order and pulled out his cock. It was a decent size and you licked your lips.

Looking into Andy's eyes you started to lick and kiss his cock all over, sucking its head into your mouth and letting out with a pop. Holding it in your hand you pushed your flat tongue against the underside and took long slow licks from his balls to its head. You slowly stroked him until he was as hard as he was likely to get.

Then you slowly dribbled on his cock head before taking him into your mouth. Andy moaned with pleasure as you started taking more and more of him in your mouth. Slowly building a nice rhythm. You felt him hit the back of your mouth and taking a breath forced his man meat into your throat. Again, he moaned. You kept your eyes on his. Putting your hands behind your back you face fucked yourself on his member.

Faster and deeper you went, taking him all with each downward stroke. You felt his cock grow, reaching up you massaged his balls and redoubled your efforts. You were rewarded with a twitch and then a moan as the stag came hard. You pulled your mouth up to his head, holding all he gave you in your mouth.

Once he had stopped cumming you opened your mouth to him, showing him his deposit. You turned and showed everyone else before swallowing loudly and shouting "mmm....tasty! thank you, Andy!" Everyone cheered! You stood up and a glass of champagne was shoved into your hand. As you drank it,

Andy was untied. His friends patting him on the back and congratulating him. One man shouted, "Well Andy, you won't forget that blow job, mate, the best and last one you will ever get!!" cheers and laughter went up from the crowd.

Then it fell silent. All eyes now on me. I looked at you and tilted my head. You understood. You smiled at me then shouted, "Who's next on this horny wet slut!!"

Within minutes there was a pile of clothes on the floor as each man stripped off. Then whilst your mind was trying to process the differing array of nakedness and swinging dicks around you, you were lifted up and carried like a rag doll into the large master bedroom and unceremoniously dumped onto the softest bed you had ever lay on.

You giggled and wriggled as what felt like a hundred hands caressed stroked and pinched your whole body. Suddenly it went dark. You shuddered. Then you heard my voice in the background "Its okay, slut, just a blindfold..." you smiled. This just gets better and better!!! Then you felt your arms and legs being pulled as you felt them being tied.

Soon you were spread eagled, tied to the bed, unable to move and blindfolded. With the torment of the last few days, you nearly came. Hard. Then nothing. No hands on you. No noise. Nothing. You lay there confused.

Then you felt warmth on your ear. You relaxed as you heard my voice. "It's okay slut, they are just sorting out drinks and deciding what order to fuck you in. Oh, I have a little extra surprise for you if you like? Another little dark deep secret you have. If you behave, I will let you have it"

You gasped and moaned "Pleeeeeease Sir! Pleeeeease!! I will be good I promise, pleeeeeeeeease!!!" You heard me laugh. "Jeez you are such a shameless whore. You don't even know what it is yet!" with that I leaned in and kissed you, pinching and pulling on your nipples as I did so. You squealed. Then nothing. I had left the room.

What seemed like an eternity you suddenly felt a presence at your side. "Well slut the gentlemen are ready for you. However, before I let them lose on you, I want to taste your sweet wet needy cunt before it becomes stretched and sloppy". You shivered.

Then you felt my tongue tease your outer lips. sucking them into my mouth and grazing my teeth along them. I took a few long slow licks from bottom to top before burying my face in your soft folds and flicking the tip of my tongue against your clit. You moaned and sobbed as I went fast and hard. Grinding my face into you. My beard tickling you.

You soon came all over my face but still I continued until you came again coating me in your sticky sweet nectar. I pulled away. "Th.....th.....thank you Sir!" you hissed. Then nothing.

You had no idea how many cocks you had and how long it went on for. You were mauled and fucked, your tits kissed licked bit pulled twisted and pinched. Your mouth used over and over as cock after cock filled your throat. You took each intrusion eagerly, moaning and whimpering when one of your holes was empty.

On they went. Relentless. Different size cocks filling your slutty pussy and mouth. Some came quick others took longer. Some fucked you hard and fast, some slow and gentle. The changing pace keeping you cumming over and over. You had never felt so alive. Your whole body felt charged with electric pulses. Your mind a complete mess as you tried to process each feeling, each orgasm, each thrust into your well worn and stretched holes.

Still they continued. Filling you with their seed. Your mouth and cunt overflowing with their cum and your juices. You were a hot sweaty mess, and you couldn't be happier. Then it stopped. You were untied. The blindfold removed. You lay there. Spent. Unable to move. Your body tingling as the blood rushed to your aching limbs.

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