Tommy Boy Gets Tricked On Halloween

Literotic asexstories – Tommy Boy Gets Tricked On Halloween by emme8,emme8
Tom’s life had been in shambles. He loved his wife, Kate, but he was unable to free himself from his bad habits—porn, alcohol, and sloth. Tom met Emme online, and she agreed to train him for his wife in an attempt to salvage their relationship and his life in general.

Tom had been a live-in houseboy for Emme for several months.

“Tommy, would you like to meet a few of my friends?” Emme asked her houseboy as he was kneeling at her feet and painting her toenails one afternoon.

“Umm, Would I be meeting them as your houseboy, or would I need to pretend to be just a friend?” He replied. “I am not sure that I could pretend to be your friend well enough to avoid embarrassing you or your husband.”

“Bob and I were thinking of hosting a Halloween party. Everyone would be dressed up and pretending to be something different. I would need your help as a server and to clean up after the party, so it would work if I hired you for the night.”

“What kind of serving do you want me to do, Miss Emme? Will this be a vanilla party? Or more of a swingers, orgy?”

“Mostly vanilla. But I may have a couple of friends that might be interested in playing with you privately afterwards. We can see how that goes later.” Emme replied as she teasingly shifted in her chair, allowing her robe to open and granting Tommy a perfect view of her freshly waxed pussy. As she moved, she intentionally smudged the nail polish against Tommy’s arm.

“Oh, damn it, look what I did again. I guess you better start over. You need to hurry if you will have time to play with me before I need to get dressed for dinner with my husband.”

“Of course.” answered Tommy as he removed damaged nail polish and reapplied the polish to the nail. “What will your costumes be?”

“I haven’t decided. Maybe Shrek and Fiona? You could be Donkey.”

“That might work perfectly for Bob and I, but you would never be cast as Fiona.” He was now blowing on her toes to dry the first coat of polish. “What if you were the enchantress Circe? Bob could be a shipwrecked and enraptured Odysseus, and I could be a male slave you had already turned into swine.”

“Oh, Tommy Boy, what a great idea. I will have to treat you to something special for being so clever. Maybe I will let my Swine Boy cum after this party, if you continue to please. That sounds so delightful.”

“Thank you, ma’am. I will always do my best to please you, even if you decide I am not worthy of an orgasm just yet. Tommy finished applying the last coat to her toenail.

“My boy, I am short on time. Help me get dressed. I will let you lick me just before I put my jeans on, if there is time. First, will you reach up to the top closet shelf? I bought a new corset, which I know Bob will enjoy seeing me wear. It is a bit complicated to get laced up, so I need your help.”

“Of course.” Tommy helped Emme into the new corset, tightening the laces in just the right places to accentuate her cleavage and her narrow waist. Then she hid it beneath a chunky sweater.

“Bob is so lucky to be your husband. And I am incredibly lucky to be your houseboy.”

“Oh Tommy Boy, you may lick my pussy now as a reward for your wonderful compliments. You are such a sweet darling.” Tommy knelt at Emme’s feet and tipped his head back, allowing Emme to push her pussy against his face. He lapped at her folds gently and inhaled her intoxicating scent. He very lightly touched and tasted her clit with the tip of his tongue, feeling the tiny bud swell.

Just as he heard a soft moan escape her lips, he also heard Bob’s heavy footsteps in the hall.

“Oh Tommy, quick, help me step into my jeans so I don’t smudge my toenails again.

I never get to spend enough time worshiping my goddess. He thought as he guided her feet into the tight jeans and into her high-heeled shoes.

“Miss Emme, If you do not have any other chores for me tonight, may I browse the internet while you are away? I will only look at ideas for your costumes and the party”.

“Yes, my boy, that would be fine.” Emme patted his head goodbye as she opened the door to greet Bob for their date night.

—————————————————————————————————

“You and Bob sure throw great parties. This was so much fun, and everyone was so nice.”

“Thank you, Kate. I wasn’t sure if I was ever going to get everyone to leave, but finally, it’s just us.

“Emme, you looked perfect tonight. That white dress looks exactly right for the Greek sorceress Circe. It’s sheer enough to show a little, but still leaves so much to the imagination. You are truly enchanting. And Bob, as the shipwrecked Odysseus, Damn, he is a Hottie.” Kate fanned herself for emphasis. “But the best of all was our little swine boy. That costume must be so humiliating for our Tommy. I’m sure he told you the sorceress Circe is like his top fictional crush.”

“Ya, he did. That’s why his costume is the swine. Tell me what you think about the look of his ass in the pink leotard and tights. He was shy about wearing it. I told him he had a great body now, and I wanted to show him off.” Emme laughed. “But I was afraid he would chicken out when I put him in the tights and started painting the rest of the costume on him.”

“His body has gotten into such good shape. I don’t think he looked that good when he was on the swim team in high school. Now, have you worked any miracles with his tiny cock?”

“Of course I have; he has a chastity cage that is a large hollow dildo. The best part is that it locks on him. I might make him wear it for our little afterparty. I think you will enjoy it.”

“Oh, Circe, you certainly are a magician.” Kate laughed

“Kate, I don’t think Tommy hasn’t recognized you in your costume yet. He can be so oblivious at times. If you can stay quiet, Tommy probably won’t recognize it as you until I make him start to be submissive to you. Does that sound like fun?”

“It does. Thank you, Emme.”

“Do you think I am bad for wanting to make him submit without letting him know who you really are?”

“I am sure he won’t mind; his standards used to be so low for a mistress.”

“Good, because I want to show off how well he is trained all the time now, and not just when he is on his best behavior trying to win you back. Besides, I want to see how long it takes him to realize he is playing with his ex-wife. It is so unexpected for you to be here; we will have to give him a little leeway. But he should recognize your body, even in the dark, before he licks your pussy. If not, I think we should make him lick your clit, while Gary fucks you from behind until you cum and squirt all over his face.”

“Oh, that sounds so wicked. I can’t wait for our little afterparty. I have missed the way Tommy would lick me to multiple orgasms. I have never had a man as skilled or attentive to oral sex as Tommy. Gary is a wonderful husband and a great fuck. He has all the important qualities that Tommy didn’t have, but he just doesn’t have the oral stamina Tommy did.”

“Well, Kate, you are going to be getting a real treat from him tonight. He hasn’t orgasmed since the first week he has been here with me. He is a desperate boy; he will be even more attentive than you remember.”.

“Emme, he’s been here for 5 months. How have you prevented him from cuming for so long?” Kate looked so surprised. “He used to masturbate multiple times a day.”

“You know, before you sent him here, when he and I were “just friends”, I strongly encouraged him to orgasm only in your presence. He wasn’t perfect, but he made huge progress.”

“Yes, I appreciated that, but that was only for short periods at a time. I can’t believe he has endured five months of denial. How have you kept him from masturbating?

“Oh Kate, I have been keeping him in a chastity cage since the day he arrived. It keeps him so well-behaved. I told him he might get to cum tonight, but he doesn’t want to. Really, he wants to save the big release for you. I think it will be fun to force him to cum for you when he is trying so hard to hold it back.

“Emme, you truly are a sadistic Domme.”

“How does Gary feel about you taking Tommy back as a house boy? Gary doesn’t seem to be a Dom at all. Does he understand the dynamics required to keep Tommy obedient? It’s more than just giving the houseboy a list of chores. Will he be okay with his wife queening her ex-husband very frequently? Or with you doling out punishments for imaginary infractions.

“I think Gary needs to see more of the dynamic to realize Tommy will not be a threat to him. Then he will be good with it. Bob doesn’t seem to mind you with a house boy.

“Kate, It takes a lot of work to keep Bob happy in this situation. Even though Bob doesn’t want the dynamic of being my slave boy, he sometimes feels jealous of all the attention I give Tommy. So we had to make some rules. For instance, it is very rare that Tommy is allowed to make me orgasm. It became a part of our play that Tommy was too pathetic to even be able to make me cum orally. I would let him try, but I frequently pre-arranged for interruptions. I would then insult him for not performing well enough, as if it were his fault. Most often, he was only treated with the privilege of preparing me for sex with Bob. And punishments. I treated him with lots of pretend punishments.”

“I bet he loved that,” Kate said, glancing over at Tommy in the next room as he bent over to gather up the empty wine glasses.

“He doesn’t actually get off on the pain as much as he thinks he does, typical guy. But he definitely responds very well to humiliation and edging as punishments. Speaking of which, do you think Gary will be game to get a drink spilled on him? We need to make Tommy spill a drink, so I have an excuse to punish him and start this after the party.”

“Definitely, I will get him to do that.

“Perfect, Make it happen soon. By the way, those are cheap wine glasses. It’s fine if they break.”

__________________________

It was only a moment later that Emme heard the glass shatter from the other room.

“You are a bloody idiot!” Gary was yelling at Tommy. “It’s no wonder Circe would turn you into a damn swine.”

Emme ran to the scene of the commotion with a towel.

“Oh Tommy, what have you done now? What a terrible mess you made.” she scolded Tommy. “Go get the broom and clean this up now.”

“I am so sorry about my boy making such a mess and splashing you with water.” she said as she turned to Gary and dried his shirt off. Then she turned to Kate and said, “Oh dear, he got you some wine also. Let me help you out of the wet dress; we can soak it in club soda so the stain won’t set.”

Tommy quickly picked up the broken glass. “I am so sorry, Miss.”

“Tommy, take this dress and soak it in club soda. Then bring a wooden spoon back with you.”

“Yes, Ma’am” and Tommy ran to comply.

When Tommy arrived back, Emme was sitting on a chair, waiting. “Over my knee, careless boy. I need to teach you to be more careful.”

Tommy turned bright red at the prospect of witnesses to his punishment. He obediently knelt over Emme’s lap.

Emme started with a few light strokes with the wooden spoon on Tommy’s buttocks. Then she increased the intensity, causing Tommy to flinch and jump.

“Gary and Bob, please hold his arm and legs still.” Both were much bigger and stronger than Tommy; they easily held him still as Emme continued to spank her boy’s ass.

Emme rubbed his ass after each strike.

“Tommy Boy, I don’t think you are learning your lesson with this spanking. Stand up and let me inspect your penis.” Tommy stood in front of Emme with his face down, his hand behind his back, and his legs spread wide. Emme closely inspected his penis, squeezing his balls and milking a drop of cum from the tip.

“Your swollen cock and precum tell me that my naughty boy is actually enjoying this. Go get me my toy bag; I will need to use something more intense.” Emme did her best to keep her voice harsh and her expression cold as she gave him the instructions. As soon as he was out of the room, she flashed Kate and Gary an excited smile.

As soon as Tommy returned, she buckled leather cuffs on his wrists and ankles and led him to the weight machine that was in the home gym. She attached his ankles to the corners of the weight bench and his wrists to a hook from the ceiling.

“Tell me, Tommy, how should I punish my careless boy? ” Emme asked as she blindfolded him.

Tommy didn’t answer quickly, so she shoved a gag in his mouth. She took the flogger from her toy bag and whipped his ass several times until he began to moan through the gag. She reached around and felt his little cock.

“Ya’ll look at this tiny cock. He is getting an erection from being punished. This kinky little boy I have to deal with and attempt to train She continued to alternate fondling his cock with whipping his ass.

“Look at this wet spot on his tights. He is leaking even more pre-cum. Maybe I should be focusing the remainder of my punishment on this tiny cock. Maybe I can teach him to control himself.”

Emme walked around the weight machine so she could use the flogger on Tommy’s cock. She landed stroke after stroke on the hard little shaft. She intentionally landed a few blows on his stomach.

“Oh, his cock is too small of a target for me to hit with this flogger.” She handed Kate the flogger. “Do you think you will have a better aim to hit this little baby cock?”

Kate took over, landing several strikes against his shaft and whipping his balls. Even though Kate was not hitting him too hard, it wasn’t long before Tommy was trying to beg through the gag. So Emme detached the cuffs from above his head and helped him sit on the bench. She began to undress him from the waist up before making him lay back on the bench. Then she removed the ankle cuffs and his tights.

Emme had stripped naked as Kate positioned her pussy above Tommy’s face. She rubbed her wet pussy on Tommy’s face. Emme grabbed a larger butt plug from her toy bag, lubed it up well, and inserted it deep into Tommy’s ass.

They watch Tommy for any changes in his reaction that could indicate he recognized the scent, taste, or feel of the pussy glazing his face with juices. Emme continued to work the toy in Tommy’s ass, edging him even closer to orgasm. Tommy was not aware the pussy he was praising belonged to his ex-wife Kate. So Kate removed the gag from his mouth and allowed him to lick her pussy.

“I’ve always been curious about the feeling of cock in my ass. Do you think I could ride that cock?” Gary spoke up as he stripped out of his clothes.

“I am sure this hypersexual toy would love to be used for your pleasure, Gary. Use him in any way you would like.” Emme answered encouragingly as she applied lube to Tommy’s cock.

Gary straddled Tommy’s waist and took the cock into his ass. He went to allow his virgin ass to open up for Tommy’s cock. Both guys were soon moaning. Kate reached over and stroked her husband’s cock as he rode her ex-husband’s face. Gary was grinding his ass against Tommy’s lap as Kate kissed his face and used her hands to bring him to orgasm. Gary came hard, jerking and spasming. He continued to shoot his load all over Tommy’s chest and neck.

Tommy was trying to say something, but Kate just ground her pussy harder against his mouth. She pinched his nipples and laughed at his attempts to squirm away.

“Gary, grind harder against him. I want to make this boy cum when I do.” Kate instructed Gary. This was the first time Tommy heard her voice the entire night.

Once he heard Kate’s voice, Tommy immediately recognized it. He let his orgasm flood through his body. Almost immediately, he pumped his hip up to shoot his jism deeper into Gary’s ass. He licked, sucked, and moaned into Kate’s pussy. Kate came hard, riding his hungry mouth. Gary was holding her tight in his arms, kissing her deeply as she slowly came down from the intense orgasm.

As soon as Kate recovered enough, she stood up and pulled the blindfold off Tommy. “Surprise Tommy Boy.”