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.
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"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.
