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Crossdresser Gets His

By: CourtStJester



Since he was a boy, he had a fascination about women's clothes. He wasn't sure how or when it started, but it grew into more that a fascination as he reached puberty. Perhaps it was the lack of a father in the house and growing up with two women. While they were he would snoop into his mother's and sister's dressers looking at their clothes. There were many wonderful things to look at. Bras, panties, garter belts and stockings (before the days of pantyhose).

Eventually his fascination graduated to trying their clothes on. It had to wait until he had plenty of time. Mother and sis may be visiting grandmother in Chicago or maybe went to the lake for the day. He would wait until they were gone for about an hour, too long for them to suddenly return to retrieve something, and then he would go hunting for an outfit to wear. 

Mother made sure sis' clothes were proper and lady-like so there wasn't too much excitement there. But mom's clothes were much more interesting. She was still young and being divorced she dressed to attract men. Her closet was filled with tight fitting skirts, sweaters and blouses and her drawers filled with lacey underwear and stockings both sheer and fishnet. And her shoes, WOW! High heels, boots, open toes. Just looking at them would get him excited.

Making sure the shades were drawn tight, he would pick out an outfit, grab underwear and hose and get himself dressed. He always made sure that he stuffed the bra with socks, not grotesquely big, but big enough so that the blouse he was wearing strained at the buttons. By the time he added a wig, one of many his mother had, he looked like his sister, only sluttier. He would prance around the house stopping at each mirror to make sure that his skirt was cut open enough to shoe the tops of his fishnet stockings or the blouse unbuttoned to show the top of his bra. 

Eventually he ended up, as he always did, lying on his back on the sofa, skirt hiked up to his hips, legs spread and a long cushion rubbing back and forth over his crotch until he came into the wadded up toilet paper around his cock. If time permitted, he would stay dressed up and get fucked by the cushion again.

Through the years, time did not permit his indulgence in his fetish very much. He moved into an apartment with friends and did not dare to have a women's wardrobe in his bedroom. He had a couple of girlfriends, was able to "borrow" their panties and would wear them under his jeans, but he missed the opportunities he had as a youth to transform himself into a girl. 

That changed the day he got married and once again women's clothes were within his reach. His wife worked a "man's" job as a carpenter and she bought clothes that needed to fit her muscular frame. And since her job alternated working nights and days, he was home alone at least once a week. The availability of clothes and the time to wear them led him to once again dress as he liked and that Friday night was once of those times.

He had come home at 5:00 in the afternoon and spent an hour talking to his wife. She was dressed in her work clothes, denims and work boots, and they shared a quick dinner until she had to leave.

"I'll be home around two in the morning," she said as she kissed him good-bye. The anticipation of her leaving and the sensuous kiss had his cock stirring immediately. As soon as she left, he locked the door and headed for their bedroom. He would at least wait a while to make sure she wouldn't suddenly return but at least could check out his favorite clothes while he waited.

He opened the closet and looked in. She had a beautiful black dress and that was his selection. It was tight and slit up the skirt on both sides. It was also backless and she had a backless bra that she wore with it. He grabbed it out of her drawer along with a pair of black panties. Although she wore pantyhose, as a gag they had bought a garter belt and black stockings to wear to bed one night. He loved those things and took them, too. And what else to go with these than a nice pair of heels. His wife had purchased one set of stiletto-heeled shoes, but her feet were a little too big for them. He was disappointed that she never wore them but now had a chance to wear them himself.

He got himself dressed, stuffed his bra and looked in the mirror. The dress was tight against his body patches of skin stuck out against the black fabric. His back was framed by the low cut of the dress and his thighs showed above the stockings. He should have been born a woman, he thought to himself. This much enjoyment taken from dressing up as one is wasted on a man. 

Since he had plenty of time, he poured himself a drink and pulled out a movie to watch. They had a few porn movies… hard-core stuff that he was surprised that his wife was willing to watch and that got her very stimulated. He popped one in the VCR, in their bedroom, sat down with his drink and started watching. It wasn't long before his cock was hard and straining under his dress. Pouring himself another drink he shut the bedroom light off, stretched out on the bed and slid his hand under the hem of the dress and started stroking his balls in the silk panties that he was wearing. His cockhead stretched up over the top of the panties and was leaking pre-cum into his hand. 

The movie showed a woman dressed in a white garter belt and stockings getting fucked by a guy with a huge cock. Although he wasn't gay, he fantasized about being a woman being fucked by a guy. He watched the movie and stoked himself with one hand and ran his other hand over his feminine body until his cock started to pulse and hot jism shot from the tip into his hand. He held his hand over his cock catching his cum until the waves of pleasure subsided and then he smeared the sticky white juice over his cock and balls. It felt nice as he massaged himself and watched the movie, and soon his cock was again hard in his hand. He stroked it again watching the woman on the screen taking a cock up her ass and he wondered how it felt. Slipping his hand underneath him he searched out his anus and slipped one, then two cum-slick fingers into his asshole while stroking his cock. The sensation of his finger sliding in and out of his ass was enough to send him over the edge. He pushed his fingers one last time deep into his ass and shot his load into his hand and onto his panties. He would have to wash the panties, he thought to himself. It was his last thought before he fell asleep.

It was several hours later and he was awake. He lay there and slowly became aware of where he was. His eyes had not opened yet but he remembered that he was lying on his bed, dressed in his wife dress and underwear and stockings with his hand on his cum-soaked cock and two fingers still embedded in his ass. It was a great feeling to be able to do this, but something was wrong. The bedroom light was on.

"What are you doing?"

He opened his eyes to see his wife standing over him looking at the scene on the bed. She had come home to find him sleeping in her clothes after obviously pleasuring himself. She had been working all night and was hot, sweaty, dirty and very irritable and the scene in front of her did not help her disposition. 

"Is this what you do when I'm not here?" she asked, not really expecting an answer.

"I… I…" was all he could get out as he started to cover himself.

"DON'T MOVE," she ordered and she started to strip off her sweaty work clothes. "You want to be a girl, you can be a girl. And I'll treat you like a girl." He didn't move. It was one think to be caught jerking off, but to be caught with your fingers up your ass and dressed in women's clothes, no she had him and there wasn't much he could do. She pushed him on to his stomach and told him to spread his legs and pull the dress up over his ass. He could only imagine what he looked like… probably what she looked like when he had her on the bed face down. He heard the drawer of the night table open and close and his wife climbed onto the bed between his outstretched legs. She was holding the dildo that he had bought for her. It was twelve inches long and two and a half inches wide. It was made to stretch a pussy nice and wide and he had bought it to watch his wife use it on herself.

"You're always asking me to let you fuck me in the ass, aren't you? Well, tonight let's see if you think it's all that you think it would be." With that, she put he head of the dido at his puckered asshole and started to push. He resisted, feeling the head trying to invade the small hole that had barely fit his fingers. She reached over and grabbed a tube of KY off the table and smeared it over the top few inches of the dildo and onto his asshole. Again she pushed and watched as his hole opened reluctantly and the tip of the dildo disappeared into his rectum.

Her husband groaned in pain as the rubber phallus penetrated him he could feel every bump and vein of the life-like cock passing his outer ring and sliding into his bowels. She continued pushing until half of the dildo was in his ass and the other half protruding obscenely out, and then she lay on his back with the exposed end of the dildo between her legs. Grasping it tightly with her thighs she started fucking him by drawing the phallus out and pushing it back in.

Her motions also had the effect of rubbing her clit on the top of the dildo and she could feel her own passions rising. As she continued to fuck her husband, she bent down and bit his exposed back.

"You look like a slut," she said to him driving the dildo hard into his ass. She was sweating now and drops of sweat were dripping onto his back. "Do you like getting fucked up the ass?" Her husband could only grunt He could smell her scent, a musky odor that was primitive and animal-like that intensified as her head would lower next to his.

"Do you like being a girl?" she said and she licked the sweat off his back then bit him hard on his exposed shoulder.

"Yes," was all he could answer.

Her pace quickened as she drove the rubber cock in and out of his ass. She could feel herself on the verge of an orgasm and loosened her grip on the dildo, allowing it to slide freely up and down her slit and she dug her nails into his back as the orgasm pounded into her body. But as the pulsing subsided, she squeezed her thighs around the dildo and continued her assault on her husband's ass. 

"No more, please," he whimpered, but his wife just ignored his please. She remembered that she had been in his positions many times. Her pussy would be sore and raw but he would take his time fucking her until he was satisfied. Tonight the tables would be turned. She was even sorry that she had used lube. Maybe next time she would do him dry.

The thought brought her to the edge and her muscled tightened and she experienced her second orgasm. This one was more powerful than the first, sending jolts through her body causing it to shake and spasm as she lay on his back. She could feel her juices splashing out of her pussy, soaking his ass and dripping down onto his balls. She lay exhausted on his back until he stirred. 

"Can I take it out," he said reaching behind expecting her to say yes.

"No, leave it in," she said in a dominating, authoritarian voice that he had never heard from her before. "We're not finished." 

Crossdresser Gets His Ch. 02



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. 



Crossdresser Gets His Ch. 03



Angela was well on her way down the highway by the time Michael had realized that his wife had bought him a maid’s outfit. It was the next step in her humiliation of him, he thought to himself.

She had pleasured herself at his expense all night then taken him shopping while he was dressed as a woman. Then she made him go down on her in the dressing room and embarrassed him in front of a rather shocked (or amused) sales clerk. Now a maid’s outfit.

Angela was nervous as she drove down the highway. She had never done this before so she picked a store that was far enough from home that no one would recognize her. She had seen this one before and after about 25 minutes driving on the highway she took the exit ramp that lead to a small industrial-type park. At the end of a building was a door with the words “Michelle’s Adult Gifts”. She parked in front, took a deep breath and walked into the store.

Angela had hoped to walk in unnoticed, but the large bell above the door rang and let everyone within five miles know that a customer had entered the store. It was unnecessary since there were what appeared to be two store clerks standing at the counter as she entered. The young one, maybe in her early 20’s, continued with her paperwork. The other, an older woman in her early 40’s with a curvy body, long straight black hair and wearing a leather skirt, looked up and smiled.

“Hi, I’m Michelle. Is there anything I can help you with?” she asked Angela.

“No,” Angela replied, “I think I’ll just look around for a minute.”

And look around she did. The store contained a wide assortment of adult “gifts”.. videos, magazines, costumes, toys. She wandered up one aisle and down another until she found what she was looking for. 

“Can I help you pick one out?”

Angela turned with a look of embarrassment on her face and Michelle just smiled. 

“I… er… um…what’s the most expensive one that you have?” was all she could get out.

Michelle reached up and pulled a package off the shelf.

“This is the most expensive strap-on harness we carry,” Michelle replied handing the package to Angela. “It’s $89.95 and not a bad one, but…”

Michelle took a couple of steps to her right and took another package off the shelf.

“This one is only $49.95 and is much better. Take a look at the straps. They are wider and more comfortable on this one and they’re adjustable. The more expensive one is not adjustable, the straps are thinner and can cut into you after a while.”

Angela didn’t realize there was so much to consider when buying a strap-on harness. She looked at the less expensive model and handed it back to Michelle.

“Thanks, I’ll take that one,” she said.

“Good choice,” Michelle replied. “Now, do you need a cock?”

Angela giggled which caused Michelle to smile. Angela noticed how pretty Michelle’s face was when she smiled and it made her more comfortable.

“Well, I already have one, but what do you have?” she replied.

“We have a large assortment right down here,” Michelle said as she walked further down the aisle. “Most of them will fit in that harness. Do you know what will best fit in your girlfriend?”

Angela uncomfortably turned to Michelle.

“Well, it’s not for a girl, it’s for my husband,” she replied hesitantly “and I want it large.”

“I see,” replied Michelle and she gave Angela a knowing glance. “How about this one?”

She handed Angela a large rubber cock. It was somewhat pliable, 10 inches long and two and a half inches thick with vein-like bumps running along its sides. She ran her hands along the flesh-colored phallus and smiled. It was perfect.

“I’ll take it,” she said to Michelle. “One question though, how do you put all this together?”

Michelle turned and yelled up to the young lady at the front of the store.

“Judy, we’re going to be in the fitting room for a minute.” She then turned to Angela. “Follow me.”

Meanwhile, Michael had changed into the maid’s outfit. It was a short number complete with black stockings and a garter. He kept his bra on and when he was finished he looked at himself in the mirror. With the exception of the cock tenting the front of his skirt, he looked like a real maid, if real maids wore this kind of outfit.

He got to cleaning the house as he was told but soon he realized that he would have to take care of his raging hard-on so he headed for the VCR in the bedroom. This time, he choose a MMF movie and lay back, stroking his cock. He had most of the work done and figured he could get his rocks off, get changed and be waiting for Angela to get back. 

He watched the action on the VCR. Two guys were doing this woman, one in front and one in her ass. He knew how that felt and was happy that part of his punishment was over. The woman was moaning and that really turned him on. He stroked faster and faster until he blew his load straight up in the air and landing back down on his cock and hand. Eventually his stroking slowed and, like most men, he closed his eyes and fell asleep.

Michelle and Angela, meanwhile, had walked to the back of the store, through a door marked “Private” and into a small room with a couch, desk, chairs and a mirror. Michelle locked the door behind them.

“Take your jeans off and I’ll show you what to do,” she said to Angela.

Angela sat on one of the chairs and undid her work boots, kicked them off and then pulled her jeans off.

“OK,” Michelle continued, “take your panties off,”

Angela hesitated but Michelle reassured her. “ I just want to make sure you get it fitted right. No sense in trying to figure out how to do it right when you want to use it, is there?”

That made sense to Angela and she slipped her panties down her legs.

“Good, now slide one leg in here. Good, now the other in here. Good. Now let’s slide the cock into this hole and pull the harness all the way up.”

With a little help, Angela pulled the harness loosely into place. Michelle knelt at Angela’s side and tightened the straps then slipped her fingers between the strap and Angela’s skin and slid them back and forth. Kneeling there, here face a foot away from Angela’s pussy, Michelle picked up the musky scent of Angela’s sex. Still kneeling there, Michelle put her hands on Angela’s hips and turned her towards the mirror.

“Take a look,” she said to Angela who looked at herself in the mirror. With her denim shirt, short hair and hard cock sticking out in front of her, she looked like a man.

“It looks good,” Angela said.

“Yes, it does,” replied Michelle who reached around Angela and stroked the cock. “It looks and feels real and with someone who really knows how to use it, well…”

Her voice trailed off.

She heard in a whisper of a voice by her ear. She took her eyes off the cock in the mirror and looked up to see Michelle standing close behind her, her eyes staring at Angela’s in the mirror. Michelle’s mouth was inches from Angela’s ear.

“Do you want to see how to use it?” she whispered. Her breath sizzled in Angela’s ear causing goose bumps all over her body.

“Yes I would,” she replied.

Michelle walked over to the couch, leading Angela by the hand, and knelt in front of it.

“Kneel behind me,” she said and Angela took her place behind Michelle, who hiked her skirt up around her waist. She reached around and took the rubber cock in her hand and guided it to her pussy. Then she bent at the waist and laid her chest on the couch.


“Push it in,” she whispered to Angela who leaned forward tentatively. Michelle reached behind and grabbing the cock in her hand pulled Angela forward. The mushroom shaped tip of the dildo disappeared between Michelle’s thighs and slid into her pussy.

“Yeah, that’s it,” Michelle groaned as Angela slid the pink monster further into her. “All the way, baby,” she whispered until she felt Angela pressed against her ass checks. “Now start rocking back and forth.”

Angela pulled back allowing about six or seven inches of the dildo to slide out of Michelle before she gently pushed it back in.

“Don’t worry, baby,” Michelle reassured her, “I won’t break.”

Angela picked up her rhythm pulling almost all the way out and then sliding back in fast and hard. She was grasping Michelle’s hips in her hands for leverage, making sure that Michelle was coming back into her as hard as Angela was pushing into her, when Michelle took one of Angela’s hands in hers and started rubbing her pussy. 

“Keep going, keep going,” Michelle panted as Angela stimulated her towards orgasm.

Angela could not believe the surreal scene she was in. She had never touched another woman, never mind having lesbian tendencies. She started to rationalize her situation by saying she was the man in this bizarre scene, the one with the cock. But no matter how she cut it, she was a woman fucking another woman.

She was now engulfed in the action, pumping the cock hard into Michelle’s pussy. Her thighs slapped against the back of Michelle’s legs and the sound blended into the background as the two women grunted with each long hard stroke and Angela picked up the pace of fucking and rubbing of the plaything in front of her.

Michelle let out a low, guttural moan and her body shook as she came under Angela’s onslaught. Her pussy clenched at the rubber toy inside it as a warmth rushed over her. She reached behind and grabbed the rubber cock again, this time trying to stop Angela from continuing to ram it into her sore and stretched pussy.

The sudden stop of motion snapped Angela back to reality. Her chest heaved as she gasped for air, feeling as if she had just ran a sprint. She looked down at Michelle whose head was resting on the couch.

“Are you OK?” she asked her.

Michelle looked back, an expression of satisfaction on her face. “Yeah, I’m just great.”

Angela slowly leaned back and let the 10 inches of rubber slide out of Michelle, who winced at its removal. 

“Well, I guess you know how to use it,” Michelle said to Angela.

“Yeah,” relied Angela, as she rose and slid out of the harness. “Thanks for the ‘lesson’”.

“No, thank you,” Michelle replied. “I’m just sorry I won’t be able to see you in action with your husband.”

Angela looked at Michelle for a minute, then reached for a pen and pad of paper on the desk.

“Be at this address at this time tonight,” she said as she scribbled on the paper.

Michelle smiled. “Can I bring anything?” she asked.

“Anything you like,” Angela replied. “I’m sure you can find something in the store you might like to bring.”

Angela gathered her things and walked to the front of the store with Michelle. Judy, who had patiently watched the store, gave Angela a knowing smile. She knew Michelle had just got fucked. She never failed.

“I’ll see you tonight?” Angela asked.

Michelle stepped towards Angela and kissed her softly on the cheek.

“I’ll be there.”



Crossdresser Gets His Ch. 04



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.