Crossdresser Gets His Ch. 04

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Wife pushes the limits with husband.
2.6k words
4.55
201k
34

Part 4 of the 4 part series

Updated 11/02/2022
Created 10/26/2003
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Angela arrived at the house and looked around. It had been cleaned pretty well but there were a few more things that had to be done. Looking around, she saw no sign of Michael so she headed upstairs to the bedroom. Sure enough, there he was lying on the bed, his hand around his cum-covered cock. She thought he looked cute in the maid outfit she bought for him and decided to let him sleep.

She was downstairs mixing herself a drink when the phone rang. She was surprised by the voice on the other end.

"Hi Angela. It's Michelle."

"Oh, hi," Angela responded after finally realizing who she was speaking to.

"I've picked out some nice stuff for tonight," Michelle said. "I hope we're still on for tonight."

"We sure are," Angela replied. "My husband is upstairs getting some rest. He has no idea what he is in for."

"Well," Michelle continued, "I have a request if you don't mind. You were dressed kind of masculine this afternoon, right?"

Angela had not changed and took a look at what she was wearing… a denim shirt, jeans and her work boots. She thought about what she saw in the mirror at Michelle's shop, a short-haired, well-toned body that could be mistaken for a man.

"Yeah, sorry I wasn't dressed more feminine this afternoon."

"No, don't be sorry," Michelle replied. "In fact, I was hoping you could dress that way tonight."

"I can do that if you like," Angela answered. "Any thing special?"

"No," Michelle answered. "What does your husband have to wear?"

"What would you like to see him in? Right now he's in a maid outfit. I can have him get into a dress or a skirt and blouse or I can have him wearing regular clothes."

Michelle thought for a few seconds.

"No, keep him in the maid outfit," she replied. "And I'll bring something extra for him. What size does he wear?" Angela gave her the necessary measurements and Michelle assured her that she would bring something "appropriate for the evening".

"I have one more thing to ask," Michelle said to Andrea. "Do you remember Judy from the store? I'd like her to come along. That is, if you don't mind."

Andrea was intrigued. "No, that would be fine. I'm looking forward to seeing both of you."

With that they traded good-byes. It was not until Angela hung up the phone and turned around did she see Michael standing there.

"Who were you talking to?" he asked, annoyed that she was telling someone over the phone that what he was wearing.

"A friend, who I am sure you won't mind will be joining us tonight," Angela replied. It was not a question looking for his agreement, but rather she was telling him.

"Well, I'm going up to get changed," he replied and turned for the stairs.

"No you're not," Angela said. "You are to stay in that outfit with that dried cum all over your cock until I say otherwise. No, go vacuum or something."

Michael sulked away. Angela was taking this too far, he thought to himself. He thought to ask who would be joining them that evening but thought better of it. Angela did not look like she was in any mood to be crossed.

Angela showered and went to the bedroom to pick out her outfit. "Think ‘masculine'", she said quietly to herself. Looking around, she picked out a pair of loose-fitting carpenter pants and another denim shirt. She went to pick out a bra and panties but stopped. No, if she was going masculine, why not go all the way. She pulled a pair of boxers out of Michael's bureau and slipped them on. Instead of a bra, she pulled out a tight fitting tee-shirt. She did not have much in the way of tits and the tee-shirt flattened her chest even more. Pulling on the pants and shirt, she turned to the mirror. She was as close to being a man as you could get without the surgery. She finished her ensemble with a pair of her work boots.

Thirty minutes later, the doorbell rang.

"Answer the door," Angela shouted out to Michael, who walked to the door unsteadily on his heels. He looked out before opening it and, upon seeing a stunningly beautiful woman, swung the door open. In front of him stood Angela and Judy.

"Can I help you?" he asked.

"I'm here to see the man of the house," Michelle replied.

"Er… that's me," Michael replied.

"No, I said the ‘man' of the house," Michelle replied brushing past Michael.

"Hi Michelle," Angela said as she walked into the living room. The two woman hugged and Angela was surprised when Michelle kissed her on the lips with her open mouth. Surprised, but not unpleasantly.

"Angela, you look very nice," Michelle said. "very ‘masculine' if I say."

Angela smiled back at Michelle. "I was hoping it was the look that you wanted."

"It was," Michelle answered. "and you remember Judy, right?"

Andrea smiled and nodded to Judy, still curious why she had accompanied Michelle.

Michelle turned and handed a bag to Angela. "After the ‘maid' serves us drinks, she can take this upstairs and get changed."

"Michael," Angela said turning to her husband who had been standing in the room silently, "get us three glasses of wine and then take this and change into it." Michael took the bag and sulked back into the kitchen.

"I have something for you, too," Michelle said to Angela. "Is there somewhere we can go to put it on?"

"Sure," Angela replied and the two headed for the bedroom. When they got there, Michelle opened a second bag and handed Angela a box. She opened it and stared at its contents. It was a cock and set of balls. Not a dildo but rather a thick, flaccid, six-inch penis with a set of balls hanging from them. The coloring and texture made them absolutely life-like. If it weren't for the base that fit into a strap-on harness, it could have been mistaken for a surgically-removed set of genitals.

"Let me explain," Michelle said taking the toy in her hands. "This fits the harness that you bought today. You just slip it in the harness. What is nice about this one is this little appendage here." Michelle was pointing to what looked like a finger on the back of the toy.

"When you wear this, this little piece slides into your pussy and up against your clit. Any movement of the cock and balls moves the little piece inside you. Put it on."

Angela got the harness off her bureau and started to undress.

"The boxers are a nice touch," Michelle said to her as she admired her outfit.

"Thanks," Angela replied. "I figured I might as well go all the way."

When Angela had the harness on, Michelle helped her with the cock, stepped back and smiled. Angela was standing there with a thick cock hanging in front of her.

"Get dressed and we'll go downstairs and have some fun," she said to Angela.

They got back to the living room and there were two glasses of wine waiting. Judy had already started on her glass before the ladies had returned.

They sat on the couch and chatted for a minute until Michael walked back in. Angela's jaw dropped when she saw him. He was wearing a long black nightgown, black stiletto heels and a black, long haired wig. Around his neck was a black choker.

"Very nice," purred Michelle, "but get rid of THAT." She pointed to the front of the gown that was tented out by Michael's erection. "I don't care how you do it, just get rid of it and when you do, tuck your cock into the panties that were in the bag."

Andrea giggled as Michael turned and left the room.

"You're terrible," she said to Michelle with a smile. "But you have great taste in clothes."

Thanks," Michelle replied "I didn't think the black nightgown was really your style. I really think that you look great tonight. I could just eat you up." Michelle leaned in towards Andrea and planted a light kiss on her lips. Pulling back slightly, she searched Andrea's face for a reaction and saw only Andrea's deep blue eyes looking back longingly into her own. Michelle leaned forward and kissed Andrea again, this time a longer, lingering kiss sucking Andrea's tongue into her mouth and playing with it with her own. Finally, their kiss broke.

"We're going to have some fun tonight," Michelle said softly. "Let me lead the way."

Andrea nodded. She was perfectly capable of designing her own fun, but this strange, erotic woman sitting beside her had an almost hypnotic effect on her. She stared at Michelle until Michael walked back into the room.

"Much better," Michelle said as she looked at the front of the black gown. Michael's hard-on was gone and the gown fell smoothly to the floor. "Now, let's have some fun. Michael, come over and kneel in front of your wife."

Michael, struggling to keep his balance in his heels, walked to the couch and dutifully knelt in front of Andrea.

"Good," Michelle said to him. "Now, unzip Andrea's jeans." Michael did as he was told and Andrea lifted herself slightly to lower the jeans and boxers and exposing the cock she was wearing.

"Michael, why don't you give your wife a blow job," Michelle told him.

Michael glared at Andrea, humiliated in front of the two strangers.

"Come on, Michael," Andrea chided him, "come give me a blow job."

Michael knelt closer and grabbed the rubber cock in his hand, his fingers unable to circle its girth. Slowly, he moved his head forward until the cock was at his lips and, opening his mouth wide, he slipped his lips over the cock head.

"Very good, Michael," Michelle said encouragingly and choosing her words carefully. "Now, suck it into your mouth until your nose bumps up against your ‘husband'." Michael started sucking and in a few seconds had a rhythm started with slurping noises accompanying his movements.

Michelle looked at Andrea and saw that Michael's actions were having exactly the affect that she had hoped. Andrea's eyes were closed and her breathing had be come increased and shallow. Her hands were wrapped behind Michael's head and guided his movement up and down the fake penis, which stimulated her own clit. As her excitement built, Andrea forced Michael to move the cock in and out of his mouth faster, sometimes even thrusting her hips forward pushing it into his throat and gagging him until she could take no more. She grabbed Michael's head and buried it into her lap as her orgasm hit her harder than ever before. Her body was wracked with spasms and Andrea cried and moaned until, finally, she collapsed back into the cushions of the couch.

"Did you enjoy that?" Michelle asked as soon as Andrea opened her eyes.

"That was fantastic," Andrea replied. "You're going to have to try it."

"Oh, I have other things in mind," Michelle replied. She looked over at her companion.

"Why don't you get Michael ready for Andrea," Michelle said to Judy who had quietly watch the scene unfold in front of her.

Judy rose off the couch and walked behind Michael, who started to lift his head of the rubber cock in his mouth.

"No, Michael," Michelle said sternly, "leave that in your mouth. We'll let you know when you can take it out."

Judy knelt behind Michael and lifted the black gown he was wearing up to his hips, exposing his ass clad in the black silk panties, his erection pressing against the fabric. Judy pulled the panties down leaving his ass exposed. She then unzipped the side of the skirt she was wearing and let it drop to the floor.

Andrea gasped. Under the skirt had been hiding Judy's cock. Not a rubber one but the real thing, thing but 7 inches long with a real set of balls hanging loosely below.

"Pretty surprising, isn't it?" Michelle said with a chuckle. "Judy can pass for a girl anytime she wants as long as she keeps that hidden."

Judy smiled and moved forward, stroking her cock until it stood out straight and hard in front of her. When she was close enough, she leaned forward and placed her cock head against Michael's exposed butt hole and, with a quick thrust, penetrated his anus. Michael, unaware of what was coming and his mouth still filled with Andrea's rubber cock, gave out a muffled scream.

"That works as a good gag, too," Michelle said as if giving a product endorsement.

Judy inched forward, pushing her cock deeper into Michael's ass until it was buried deep inside, then eased the long, rubber phallus out until only the head remained inside Michael. Then, just as slowly, Judy slid her cock back inside.

Andrea watched as Judy slowly sawed in and out of Michael's ass. It was one thing to fuck him herself with a strap-on, but to watch a real cock ream his rectum was an altogether different scene. One, incidentally, she was enthralled watching.

Judy picked up the pace pushing her cock deep into Michael, each time ending with her balls slapping against his. The force with which Judy was pushing was forcing Michael forward and Andrea's strap-on buried itself in his throat. He was grunting and gasping for air as Judy continued her assault on his ass. She must have been at just the right angle to massage his prostate since his cock suddenly erupted spewing strings of white cum onto Andrea's work boots.

Michelle glanced at Andrea and saw that she, too, was close to experiencing another orgasm. Leaning over, she caressed Andrea's breasts through her shirt and, bringing her lips to Andrea's, kissed her deeply. Andrea released her husband's head and pulled Michelle closer as she came hard and fast.

Judy was ready, too. Her pace had picked up to a point where the rhythmic "slap", "slap", "slap" of her skin against Michael's was the only sound in the room. Finally she tensed, pushed hard into Michael and her cock started twitching. Michael could feel her hot load of cum deep shooting into his ass.

Michael thought to himself that his humiliation was over but he was wrong. As soon as Judy's cock had softened and slipped out of Michael's as, she knelt beside him and, grabbing him by the hair, pulled him off Andrea's strap-on and to her dripping cock.

"Judy has to leave, Michael," Michelle said to him, "and you need to clear her up."

Judy brought her cock up to Michael's lips and pushed it into his mouth.

"Do what Michelle said," Andrea added. "Lick her clean."

Michael reddened with embarrassment but did what he was told to do. Sliding his mouth down onto Judy's cock, he licked and lapped at it sucking the combination of her cum and his juices off the limp organ. After a nauseating five minutes, Judy pulled out of his mouth and stood.

"See you at the store tomorrow?" she asked Michelle. Michelle rose and kissed Judy gently on the lips.

"Yes, love. See you tomorrow."

Judy pulled her skirt back on, gathered her things, said good night to Andrea and slipped out the door.

"Let's go upstairs and have some real fun," Michelle said to Andrea.

Andrea took Michelle's hand and lead her to the bedroom, Michael following behind.

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12 Comments
1Martiniman1Martiniman8 days ago

Abandoned story…what a shame.

cdCindy1cdCindy1over 2 years ago

I agree with another reader -- you need to find a female name for Michael. He is so pretty in his new clothes and when he gets fucked by a real cock. I wish I was him/her.

LisaBrooksLisaBrooksover 5 years ago
Judy's Surprise!

Now that was fun! I love those cocks that give the user as much pleasure as the recipient getting the pounding! I also loved how Michelle showed Angela / Andrea a coarse in "How To" with a strap on! That sexual moment gave Michelle a path to her own sexuality! Great story! We need another story to see how Michael transforms in to a ravishing woman!

AnonymousAnonymousover 8 years ago
Judy stuck her cock into his mouth

And he bit it off. What? You think he would let her get away with that crap? That was the end of the whole mess. Judy was left with a stump. Michael beat Andrea to a pulp later that evening and left her.

satinshawnasatinshawnaover 9 years ago

oh, how I would like to be Michael

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