Crossdresser Gets HisbyCourtStJester©
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."