Crossdresser Gets His Ch. 02

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Wife takes dressed-up husband shopping for clothes.
2k words
4.33
183.1k
23

Part 2 of the 4 part series

Updated 11/02/2022
Created 10/26/2003
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She certainly had a busy night. Between the time she came home and found her husband in her clothes and the time they woke up, she had fucked him with her 10-inch dildo four times. He was barely able to tolerate the first two times, and the third and fourth were excruciating. Sometime after that, his wife either pulled the dildo out of his ass or he expelled it himself.

They woke pretty much the way they fell asleep. He was still dressed in a black dress, bra and stockings. Some time during the night the cum soaked panties had come off. His wife lay next to him naked, her short brown hair soaked in sweat from the constant fucking she gave her husband that night. Her pussy was sticky from her own juices but none of him. In fact, she had not touched his cock all night. She rolled off the bed and looked at him. There was something strangely erotic to the scene. She never fantasized about dominating or cuckholding her husband, but between her legs tingled at the sight of him lying in bed.

“Roll over on your back,” she said and he complied immediately, wincing as his ass cheeks pressed into his raw anus. She climbed onto the bed and straddled his head, lowering her musky pussy onto his mouth. “Lick me,” she ordered.

Her husband started sucking on her pussy using his tongue to probe deep inside her. Usually he did not go down on her after sex, even if he had not cum in her. A nice clean pussy is one thing, but he avoided “used” ones. But not this morning. She grabbed him by the hair and forced his face into her snatch, riding his mouth to her own pleasure. When she came, her juices flowed out of her and she used her pussy hair and labia to spread it around his face. Satisfied, she got up and off the bed.

“Get up,” she said and he did as he was ordered. It was clear that sometime during the night he had cum again, this time on her dress.

“You’ve ruined that dress,” she said to him. “You know I don’t have a lot of good clothes to wear. You’re going to have to get me another.”

“Yes, dear,” he said like the now pussy-whipped husband he was.

“Take a shower. We’re going shopping this morning,” she said as she wrapped a robe around herself and headed to the kitchen.

Her husband headed for the bathroom and started to undress. He got the dress off and looked in the full-length mirror. He thought he looked good in the bra, garter and stockings, but knew he would never enjoy getting dressed up again. His wife would be looking for telltale signs that he had been in her clothes. No, he had his fun for a while. He climbed into the shower and washed himself off. His cock was a sticky mess and it took some extra cleaning to get the cum out of his pubic hair. When he was done, he dried himself off and applied some aloe lotion to his burning asshole.

He found his wife back in the bedroom laying out her clothes and he went over to his bureau to get his own.

“You don’t need yours,” his wife said, “this is what you’re wearing today.” She was pointing to the clothes that she had laid out on the bed. There was a pink turtleneck sweater, black skirt, pantyhose, bra and panties. On the floor was a pair of black pumps. He stared at the clothes and started to object, but she cut him off.

“What’s the matter? All of a sudden you’re not interested in women’s clothes anymore?”

Her husband said nothing, choosing to remain silent rather than incur her wrath. No, he’d let this blow over in due course.

“I’m taking my shower,” she said as she headed for the bath. “Be dressed when I come out.” She shut the door behind her and he heard the water start to run. He dressed as quickly as he could given the assortment of clothes that she had left for him and in a few minutes he was sitting on the bed waiting for her.

“Very pretty,” she said as she stepped out of the bathroom. She was still drying herself with a towel which she dropped to the floor leaving her naked. “We’ll have to do some touch-up work. Come over here.”

He sat at her make up table and she started working on him applying makeup and eyeliner to him while standing directly in front of him. Her small tight breasts were nipple-to-eye with him and he could not help look at them and feel his cock harden. He reached up to fondle them but instead received a hard slap across the face.

“Don’t even think of that,” she said to him. Then, looking down and noticing his hard-on tenting the skirt he was wearing added, “and get rid of that!” He didn’t need to be told twice since the slap in the face quickly deflated his cock.

Once she finished with the make up, she went to the closet and pulled out a wig of long, black hair. Setting it on his head she shifted it around until she stepped back satisfied that she had it right.

“Go downstairs and wait for me,” she told him, “And put your wallet in this.” She handed him a purse and he got up and left the room, pausing in front of the full-length mirror briefly to admire the way he looked. He may be in trouble with his wife, but this was the best he had ever looked dressed in women’s clothes. “Maybe,” he said to himself, “I should get caught more often.” But he though different when he sat down on his sore asshole.

His wife joined him a few minutes later. She was dressed more casual, more male-like, in jeans, denim shirt and work boots. With her short hair, small breasts and muscular body you could almost mistake her for a man. It was almost like she was trying to hide her femininity as much as she was trying to expose his.

The ride to the mall was a fairly short one, but the cold silence in the car made it all that much longer. She drove… he didn’t even bother to ask for the keys… and parked in the parking garage. It was then that he thought of the possibility of running into someone that might know and recognize him.

“Do we both have to do this?” he asked, hoping that maybe he could wait in the car.

“Yes,” she answered coldly.

They both got out of the car and walked into the concourse of the mall. At first he was self-conscious, looking at everyone hoping that if he saw someone he knew he could avoid them before they saw him. But as they walked, he realized that he was doing what he always wanted to do, walk around in public in women’s clothes. His heart pounded with fear and excitement as they made their way through the mall to Anna’s which was a moderately priced women’s clothing store. His wife picked out here dresses. One was a slinky black number similar to the one her husband had soiled. The other two were pink and blue in color, with a sexy cut to them.

“Let’s go,” she said to him as she headed for the changing rooms. He followed her in and she tossed the two dresses to her husband, holding on to the black one.

“Try those on and let me see,” she said and she disappeared behind the curtain of her changing area. He went into his and slipped out of his sweater and slacks and into the blue dress. It was a snug fit, clinging to his ass and bust, but it was a very sexy looking outfit. He emerged from his changing area and went into his wife’s. She looked stunning in the black dress she had put on.

“Kneel down,” she said to him and did so without asking why. She lifted one foot onto the sitting bench in the dressing area and lifted the hem of the dress, exposing her pussy to him. Without saying a word, she grabbed his head and buried his face in her pubic hair. Her husband’s tongue immediately went to work on her, probing deep inside her. One of her hands held his head in place while the fingers of her other hand found and massaged her clit. She writhed in pleasure moaned loudly as she stimulated herself and her husband went down on her until a voice interrupted them.

“Is everything OK in…” the salesgirl said until she saw what was going on. “Sorry,” she added and turned and left.

Her husband probably did not even hear the sales girl since his tongue never stopped and in a minute his wife climaxed with such intensity that her juices ran down the length of her leg. She continued to rub his face in her pussy milking every throb of her orgasm. When she was satisfied, she looked down at him.

“Clean me up,” she ordered and her husband immediately started licking her pussy. She pushed his head down and he licked her juices off her leg until he reached her foot. Sticking his tongue out he cleaned all of her cum off her foot. When she was satisfied, she started taking off the dress she was wearing.

“Go get dressed,” she told him and a few minutes later he emerged carrying the two dresses he had tried on and carried them over to the register. His wife had the black dress she had just worn.

“Pay the lady,” she said and walked away to look around the store while the sales girl rang up the purchases.

“$259.97 please,” she said once she had totaled the purchases.

She took the credit card, swiped it and looked at the name on the card. It said “Michael”. She looked up, then down at the card again and then up again.

“Can I see your license?” she asked. Michael reached into his purse and pulled out his driver’s license.

“Is everything OK?” his wife asked the sales girl who was looking back and forth between the license and her husband and then finally, with a broad smile, at his wife.

“Oh, absolutely,” she replied and handed the sales slip to Michael to sign.

Angela gathered up their packages, turned and walked out of the store and over to her husband who, embarrassed at the register, was sitting on a bench in the mall, legs crossed looking positively feminine. Guys were passing giving him second looks, although she was not sure it wasn’t because they recognized a guy in drag.

“Come on,” she said to him. “I have more shopping to do.” They walked to the car and Angela got behind the wheel again. She thought for a minute and then smiled. Their next stop would be a surprise. She headed towards a store which always had a good supply of costumes, even when it wasn’t Halloween. She pulled in and told him to wait in the car until she came out and disappeared into the store, coming out a few minutes later with a bag in her hand.

“What did you buy?” Michael asked, partly to strike up a conversation and partly out of curiosity. Angela just started the car and pulled out of the lot.

“You’ll see soon enough,” she replied and they headed towards their house. When she pulled into the driveway, she turned to her husband and handed him the bag.

“I need to get some more things,” she said to him. “Hang the dresses in the closet, put this on and clean the house.”

Michael got out and Angela wasted no time in leaving, almost running over his feet in the process. He walked back into the house, upstairs to the bedroom and tossed the packages on the bed. He liked getting dressed up but this was going on too long. He didn’t intend to spend the rest of the weekend dressed as a woman. Walking over to the bed, he pulled the three dresses out of the bags and hung them in the closet. He flipped the last bag upside down and emptied the contents on the bed. It was a maid’s outfit.

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5 Comments
nancysilksilknancysilksilk11 months ago

I loved it keep writing

LisaBrooksLisaBrooksover 5 years ago
Interesting!

I can relate to the early beginnings of Michael! I, too, did the same as a 10 year old! I got married, divorced then almost married again! As the fiance' moved out I tried on her nylons and panties! I had 2 children and that moment trying on the fiance's clothes triggered my crossdressing beginnings! I had to hide it! Confused I seeked help finding out I was transgendered and given HRT to change my sex! Enough about me but stories like this tell me I'm not alone! Lets see what happens in the next chapter! Thank you ..........

Brian70Brian70about 6 years ago
Nice

Enjoyable story that I hope you continue. I would love to have a maid's uniform to clean in but for now it is heels and usually a sleeveless dress. Xoxoxo, Brie

cdCindy1cdCindy1over 6 years ago
maid's outfit

I love wearing a maid's outfit. I wish my wife would buy one for me. I would love to go out shopping with her. I can't wait to read your next chapters.

AnonymousAnonymousover 8 years ago
He was dressed when she came out of the shower

In his typical men's clothing. He told her the fun was over. When she threatened him he started to pack his stuff. She asked him what he was doing. He told her that he didn't want a manipulative bitch for a wife and that she'd hear from his lawyer. They were divorced 4 months later. She never saw or spoke to him after that day.

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