Toms Downfall

Tom always thought of himself as quite a ladies man. He was smoothie, good looking and always with a good looking woman on his arm. A different woman every night was quite normal for him and he was envied by every man and desired by every woman. How he ever kept it straight Lord only knew, but it must have been quite the mental challenge. It was his underestimation of the wrath of scorned women however that finally did him.

Sherry and Tammy had been friends ever since high school. They shared everything; sweaters, makeup, and little did they, or he realize they shared Tom as well. Tom had dated them both for months and amazingly he never realized that both of them were such good friends or even knew each other for that matter.

One afternoon Sherry and Tammy were having lunch. As they both began to talk about their respective love lives Tammy mentioned her great new lover Tom.

"Tom is the best lover I ever had. He can go on and on without cumming, always putting my needs before his own. I think I am really starting to fall for this guy" Tammy said.

"Isn't that ironic" Sherry interrupted, "My new boyfriend is also named Tom, and has the same amazing lovemaking qualities as your Tom and is a real hottie to boot. We always did have ver similar tastes."

"Really" Tammy said as she whipped out her iPhone. "Let me show you a picture of my Tom. I bet he is better looking than your Tom" she said giggling, feeling suddenly very competitive with her friend.

"Oh yeah!" Sherry remarked irritatedly. "Here is a picture I took of him last week at the beach. You will notice he is not lacking anything in the bod department."

"THAT FUCKING BASTARD!" Tammy shrieked. "Look at this picture I have and tell me what similarities you see!"

Sherry took her phone and looked at the picture. Tammy could tell from the expression on her face that she realized the same thing she had just discovered. They were both dating and fucking the same guy!

"I am going to call his ass right NOW and tell him to go fuck himself!" Sherry screamed. Almost crying now, her eyes got watery as she spoke. "I really was falling for that asshole" she sobbed, barely holding back the tears, "and it was all just a big joke!"

"Wait, before you call him I think we need to teach little Tom here a lesson about how to treat women" Tammy said, while trying to console the now sobbing Sherry.

"I don't think he realizes that we are such good friends, or for that matter even know each other. We could definitely take advantage of that fact and teach him a lesson he will never forget. I happen to have a date with him tonight so I'll call you later with my plans."

Portrait of a doomed man. Tom, grievously unaware of the forces being arrayed against him prepared for his date. As he was getting dressed he casually looked through his little black book and smiled.

"Tonight is Friday" he thought to himself. "Ah yes, Tammy night! I can't wait to suck on those "tig old bitties" of hers." Both Tammy and Sherry, in case it had not been mentioned before are both truly stacked. Tammy measures 44-29-36 and her friend Sherry measures a respectable 39-26-33.

"Tonight Tammy, tomorrow Sherry, lunch with Susan on Sunday, Monday movies with Lisa. I truly have it made" he thought to himself smugly. After the short drive over to Tammy's, Tom was excited to see that he was greeted at the door by Tammy in nothing but her black teddy.

"Ooooh BABY, I love it when you wear that outfit" he whistled as he licked his lips and looked her up and down.

"I thought we would stay in tonight, if its ok with you" Tammy asked to which Tom nodded his head vigorously and lunged for her glistening cleavage.

"Not yet big boy!" Tammy declares mischievously, "I thought we would try something a little kinky tonight, are you game?"

"You bet!" Tom says enthusiastically. "Sooooooooooo, What do you have in mind?"

"First, go up stairs, get naked and get into bed. On the nightstand you will find three pairs of handcuffs. Cuff your hands over your head and your ankles to the ends of the posters on the bed and wait. Tonight you are going to be licked and teased into the best sex you have ever had! You think you can handle that?"

Tom raced upstairs like his life depended on getting naked as fast as possible. His hands were shaking from excitement as he quickly stripped off his shirt, shoes, pants and shorts. As he closed the last handcuff on his wrist he felt exhilarated. Now he was stark naked, spread eagled and completely helpless and already hard as nails.

"Ready!!" he yelled.

"Are you sure?" called back Tammy.

"You bet!" he yelled back.

"Completely nude and helpless?"

"Yes, Yes and getting hornier by the minute, come on up BABE and let's do this thang!" He joked.

"Ready or not here we come!" Tammy called.

The look on Tom's face must have been hilarious because both Tammy and Sherry both laughed simultaneously at his expression.

"Hi Tom, remember me?" asked Sherry.

"Oh by the way Tom, Sherry is my best friend and we share everything, and we never realized it also included you." Tammy said sarcastically.

By this time Tom had come to the realization he was in severe trouble and began to twist and turn and try to get out of his handcuffs. Watching him struggle, both girls started to giggle.

"No use trying to escape" Tammy said "the key is in a safe place." With that she took out a gold chain that was hanging between her breasts and began to swing it around. On the end of it was the key.

"I-I-I" Tom stuttered.

"Words escape you, huh?" Sherry laughed. "What do you want to do to him first Tammy?"

"Hmmm, I am hungry, how about you? Lets have a Tomcicle!" As she made her suggestion Sherry pulled out from behind her back a jar of Hershey's chocolate syrup that had just been heated in the microwave. Striding over to Tom's rock hard member and softly beginning to stroke the sensitive glans on the head she smirked as he began to twitch.

Each stroke sent what felt like an electric shock through his body and he was already squirming desperately and she had not even begun yet. Slowly dripping the syrup on the very tip of his dick and glacially beginning to lick it off, she looked Tammy and winked as their mutual boyfriend just moaned. Slowly being coated in chocolate, Tom had never been so aroused in his life! Tammy and Sherry kept feasting on his helpless member for what seemed like hours and several times he thought he would cum but never quite made it. The girls sensed when he was getting close and they used this information to stop while he calmed down before they started up again. After another hour of this treatment he was mad with lust.

"I tell you what Tom" Tammy said. "If you give Sherry and myself three orgasms a piece in one hour, we will let you go. Otherwise, you will remain here tied, naked and frustrated for a week. Deal?"

"Deal!" Tom nodded as he had no choice and what did he have to lose after all.

Sherry was first up and crawled onto his chest and thrust her sweet dripping cunt right in his face. As soon as he took a long whiff of her scent, he began to lick,suck and chew like a man possessed. Her scent and taste was driving him crazy. As he feasted away eating her out she lazily licked his balls making them bluer and bluer as the minutes ticked by. He thought he would burst when finally she shuddered and cried out.

"Thats one!" declared Tammy. "That took fifteen minutes, so you are going to need to step it up a bit boy. I hope you can beat the clock." Sherry rolled off of Tom and sat in a chair beside the bed to recover while Tammy got her treatment.

"I think I will ride the white worm for my turn on the Tommy-go-round." Tammy said, while she pulled out a rubber band and tied it tightly around the base of Tom's dick.

"Don't want you cumming too soon now do we?"

She quickly mounted him and began to buck and rock like a rodeo rider. Tammy purposely teased him by keeping her nipples just out of reach of his tongue, the chain with the key hung tantalizing in front of his eyes.

Three or four minutes of this and she moaned and rolled off as her juices poured out of her and onto his stomach. His dick was on fire now, especially as she carefully removed the rubber band, avoiding contact with his swollen glands.

Sherry was eaten out again and then Tammy had a repeat. As Sherry was coming back for thirds Tom heard a buzzer go off. "Oh, too bad. You did not make it." Tammy smirked. "Well, I am off to bed now, I'm tired. How about you Sherry?"

"Yeah, I'm pretty tired too. We can continue this in the morning." Sherry said.

"What about me!!" cried Tom, almost insane with lust. "You can't just leave me like this all night!"

Tammy's smile grew wide at his words and she suddenly pulled out a strange looking device. It had a long tube on one end and was attached to some sort of pump on the other.

"You are absolutely right Tom, and we aren't going to." Tammy said. "This milker should keep you good company tonight." She cackled as she slipped the tube over Tom's throbbing cock and turned on the switch.

"Nighty,Night Tom!" Sherry said.

"Sweet dreams!" Tammy added as both girls went into the other bedroom leaving Tom alone. The device they had placed on him slowly fired up and hummed and sputtered as it began to stroke him, increasing it's speed every few minutes or so. After about 15 minutes he was arched up off the bed as he felt the sperm rising in his balls and his toes started to curl and reflexively began to tense up, ready to cum.

The machine must have some sort of monitoring device because right at the last possible moment it shut down completely, leaving Tom teetering right on the edge. He almost started to cry at that very moment as he felt his orgasm slip back down into his aching balls.

Oh well, maybe I can get some sleep now, he thought to himself. As soon as I calm down a little bit I will doze off. Four or five minutes later his penis was beginning to get limp and he started to drift off.

Once again some sort of monitoring device caused the machine to start back up again.

"OH NO! Not again!" screamed Tom as everything started over. Once again it brought him right to the edge and stopped and the cycle continued all night.

The next morning Tom was nearly insane with horniness. Try as he might he could not get the device to let him cum. The door to the bedroom swung open and in walked Tammy and Sherry.

"Morning Tom!" the two beauties said musically.

"Please, please, please let me cum!" Tom pitifully begged as he whimpered and writhed on the bed. "I think I will lose my mind if this keeps up much longer!"

"Don't worry Tom, a week will pass quicker than you think" Sherry said while trying desperately to hold back her giggles.

"NOOOOOOO! Please, I'll do anything you want just please let me cum!"

"Not yet! You need to earn that right!" Tammy yelled back at him. "Sheyeww, you smell. I think its time we bathe you and let you go to the bathroom. No doubt you need to pee right now." The girls giggled as they attached a dog collar to Tom's throat and added another set of handcuffs. These attached his wrists to the collar, so his arms were kept away from his package and he was just as helpless as he was on the bed. After his collar was secure, they then unlocked the first set of cuffs and the leg cuffs and led him by the dick into the bathroom.

"Get in the shower slave-boy! I think we got your face quite dirty last night!" they laughed as they watched him step into the tub and they turned on the water. Now standing in the shower, Tom closed his eyes as the warm water on his dick felt like a million tongues lapping at his cockhead. He had been rock hard for almost 18 hours now and was on the verge of shooting his load at any minute, it would only take a tiny bit of sensation to cause him to pop.

Despite knowing it meant more teasing and suffering, he smiled when he saw Tammy and Sherry get undressed and join him in the shower. The girls were giggling uncontrollably as they gently lathered him up from head to toe being extra careful not to stimulate him too much to orgasm but making sure his dangly bits were nice and foamy. They also lathered themselves up and got a big thrill pressing their naked, soapy tits up and down his chest as his moans echoed against the marble tiles.

Tom, writhing and moaning, wished hopefully they would slip up and stroke him to release, but they never did, and after a very long hot shower they all got out of the tub and dried him off as well as themselves.

"Do you have to go to the bathroom Tom?" Tammy asked as she noticed him crossing his legs. When he nodded he did they uncuffed one of his hands and left the room.

Pausing as she left, Tammy said "If you jack off while alone and uncuffed in here, we won't be as nice to you today as we have been so far, got it? Don't take too long, you have much work to do today as your suffering and punishment is just beginning." She winked as Tom again nodded as they left the room.

Giggling, they were both sure to take all the towels and the curtains with them as they left him alone. "I don't think we have to worry about him escaping" Sherry said. "After all, where can he go naked as he is?" They both left him alone and closed the door behind them as they wanted to give their prisoner a little privacy to relieve his bladder.

After Tom peed he noticed that outside the window was a fire escape that beckoned to him for thoughts of freedom. The idea of being caught in the infernal milker again, and who knows what else this afternoon made Tom really consider his escape options. He enjoyed the oral worship on his two girlfriends, but he realized they were never going to release him and he worried greatly about exactly what terrors they were going to inflict on his balls today.

"I don't live that far away." he thought to himself. "If I run very fast and stay near the trees, nobody will see me." As he quietly opened the window he heard the girls rustling in the other room, obviously monitoring the bathroom for suspicious noises.

"Whats going on in there?" Tammy asked. "Hurry up or you are going to really be punished!"

"Just a minute!" Tom shot back, trying to buy time. He needed not only this window, but a window of opportunity to make a break for it and as he inhaled deeply, he quietly slipped out the window and onto the fire escape.

He turned beet-red with humiliation as this was the first time he had been outside totally naked before. To make matters worse he only had the use of one hand, the other being still cuffed to his collar. Being early morning, now was the time for any attempt at escape and he decided to make a run for it.

He scrambled down the fire escape as fast as he could run and out into the parking lot where he accidentally ran into a girl who was out jogging. As she screamed and said she was going to call the police, Tom said nothing but just kept running. There were a bunch of trees behind the apartment complex, and if he could just make it there he could sneak through the woods and over to his own apartment which was on the other side.

His feet were covered with scrapes and scratches from the pavement but he made it to the woods and was very tempted to jack off right there. He had been teased all night and needed release bad, but he continued onward in his nude dash.

"Time enough for that when I get home" he thought as he continued running through the woods. "I hope my key is still under the mat". A half an hour later he finally reached his apartment building, the naked journey through the underbrush taking longer, and being more painful than he had hoped. He had been lucky so far, other than a few joggers, no one had seen him so far. This however was going to be the hard part.

His apartment was on the third floor and he would have to go right by the pool in order to get to it so he waited for the opportunity to come when the fewest people would be in his path. When he finally saw an opening he made a break for it.

As he raced by the pool he heard four or five girls laughing hysterically and pointing at him and his face grew even redder. He had never been so embarrassed in his life, but he was almost home and in just a few more steps he knew he would be safe. Looking behind him his humiliation grew as he realized that a couple of rather busty and bikinied teenage girls were now chasing him. His heart beat fast in his chest as he ran faster, so close to ending his nude display.

He beat them to his apartment and luckily found the key still under the mat where he had left it. Opening the door he rushed in and slammed it behind him just as they were came up the stairs and as he panted inside he could hear them asking each other where the naked man had gone through his now locked door.

His heart was racing and he was shaking with sweat and lust he smiled as he took his hard suffering cock in his hand and prepared to whack off when suddenly the lights were flipped on!

"Welcome home Tom!!"

He felt his heart sink when he now realized that he was standing start naked in a room full of all of the girls from his little black book, twelve in total.

Susan, the girl he was supposed to have had lunch with on Sunday spoke first.

"Tammy called us all up and told you what you were doing and how you were playing us all for fools! Its time to settle up Tommy boy." And with that that two of the girls grabbed him by his hair and dragged him into the bedroom as the rest of the crowd laughed and followed them inside.