Billy & His Goddess, Theodora

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Stripper deflowers a virgin young man.
5.8k words
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* * * * *

In the early Fifties, the last refuge of vaudeville was the burlesque theaters. These palaces of entertainment had deteriorated from their former glory, but they were still booking live entertainment. Great comedians and, of course, the glamorous strippers attracted the younger generation. The comics were risqué for those times, but none of them worked 'Blue'. The strippers were part of the skits and the audiences laughed heartily and truly enjoyed themselves.

The young people, one had to be eighteen to get in, arrived at the theatre early enough to get front row seats to better view the strippers. The women stripping were mostly performing the same basic routine, which was a fully clothed short dance, followed by a stripping dance illuminated in a blue spotlight. The strippers would often whisper or talk softly to the front row characters to get the patrons attention. This way the patrons would return again and again in the hopes of somehow meeting these lovely ladies. Little chance of that, but hope is always eternal, especially when you're eighteen.

A group of young friends from a nearby city would save their money all week so they could afford the bus ride and burlesque ticket on Saturday night. Billy was a member of such a group of young men in their late teens or early twenties that made a ritual of going to the burlesque show nearly every Saturday night. They would get to the theatre when it opened, get the front row seats, which they occupied until the theatre closed at midnight. In those days, one could stay through multiple shows on a single ticket. Billy and his friends would always try to strike up a conversation with the strippers. Sometimes it worked and other times they were ignored.

The singular exception was Theodora. She was a local girl in her early twenties and loved to strip and talk to the front row patrons. Rumor had it that she was the girlfriend of a Mafia gangster and she pretty much did what ever she felt like doing. One of the things she liked to do is display her self totally nude when she danced. Unlike the other strippers, she did not strip. Theodora came out onto the stage in a black and red silk cloak to a drum roll. When the band started to play a bump and grind tune she threw off the cloak, stood stark naked, smiled at the patrons and began to dance.

Because of her rumored boyfriend, no one ever tried to stop her from dancing completely naked, not even the police. The cops were said to be in the mobsters' employ and turned a blind eye to Theodora's nudity. She loved to talk to the 'kids' in the front row and tease them that they should go home and get ready for Sunday school in the morning. It was all good-natured fun for Theodora, but for them it was fuel for their wildest fantasies. Each of them had often fantasized about going to bed with her and they all admitted to one another that they had masturbated fantasizing about her. Theodora's main claim to fame as a stripper was that she had a great and voluptuous body and that she was naked from the start of her routine until the end.

She had dark hair that fell to the middle of her back. Her body was solid, but not real thin. She wasn't plump, but she wasn't like the other skinny strippers, she had a body that stood out from all the rest. Her breasts were huge and defied gravity. In those days, no one had heard of implants and the way they jiggled and swayed gave proof to their reality. Her nipples stood out at least a half inch and were as thick as the end of a forefinger. They crowned her rosy areolas that were about the size of a silver dollar. Her dark bush was neatly trimmed, but her pussy was slung low underneath her and it was difficult to see it when she danced.

Sometimes she would give the guys in the first row a lightning fast glimpse of it, then giggled as she danced away from them. One autumn Saturday night Billy found himself alone for the evening. His friends had to accompany their parents to a wedding, thus were not going to be available to hang around with him. He thought about just going to the movies alone and call it a night, but the head that controlled his horny mind decided to go to the burlesque show alone. He rode the bus to the city and walked the short distance to the theatre. He was too early and went to a nearby grill to get a hamburger and coke while he waited for the theatre to open.

"Hi friend," said a very sexy voice as a woman touched his shoulder, "where are your buddies tonight?" Billy turned to see his 'Goddess' Theodora sitting in the booth behind him. She smiled at him and Billy wanted to melt and disappear. She was dressed very nicely, but sexily too, and wearing a fur coat. Across from her was seated a very big man with a dark complexion and a scowl on his face.

"Ah…ah…my friends are…are…not coming tonight," Billy stammered and looked at her forehead unable to look her in the eyes.

"Well, if you're alone, come join us and we'll eat together, ok?" she said to him. Billy was stunned. He felt his heart pounding in his chest and he thought, for a moment, that he might get sick from the butterflies in his stomach. He looked at the big man seated with her and the man smiled a toothy grin and waved to him to come sit down.

"Come on, kid. I won't bite and neither will Miss Theodora. Get your butt over here," the man said in a deep friendly voice. Billy got up and carried his plate and coke to their booth and sat down next to the man. The man held out a beefy hand and Billy shook hands with him, "I'm Rocco," he said with a friendly smile, "what's you're name?"

"William, but my friends call me, Billy," he managed to say without stammering. Theodora grinned at him with her perfect white teeth shining and nodded hello. Billy nearly swooned from excitement as he sat mesmerized by her beauty.

"Hello, Billy. I'm sure you know my name," she said smiling at him.

"Yes, Ma'am, I do," he said.

"Billy, my name is not Ma'am, it's Theodora and I prefer that you call me that please," she told him pleasantly. "Rocco is my driver. He works for my boyfriend and makes sure that I only meet nice people like you," she said, grinning. Rocco grinned and shook his head as he lit a cigar. "Well, Billy, are you coming to the show tonight?"

"Yes I am," Billy said, "I love your shows, Theodora," he said, not believing that he had actually called her by her first name.

"Good, I'll see you in the first row, I'm sure, Billy," Theodora smiled as she got up from the booth, "time to go get ready." Billy wondered why she had to be so early since costumes were not a problem for her, but he just kept his mouth shut and nodded. Rocco took Billy's check and Billy let him slide out of the booth.

"I'll get the check, kid," said Rocco smiling, "nice, meeting youse." Billy shook his big hand again and smiled as they were leaving. Theodora turned to look at him when she reached the door, smiled, winked at him and left followed by Rocco. Billy was in heaven. He had met his 'Goddess' and had 'dinner' with her too. None of his friends were going to believe this in a million years. Billy seemed to be in a trance when the waitress interrupted his reverie by asking him if he wanted anything else. He declined and left to go buy his show ticket. Billy sat in the front row when the evening show started at eight o'clock. He laughed at the comics and got his usual hard-on when the strippers danced and stripped. He saved his most ridged hard-on for Theodora's act and fantasized again about her. There were three shows each evening with an intermission between the shows. The third and final show started at around ten-thirty and would finish at midnight. Theodora usually closed the show, each night and tonight was no different. Billy stayed to see her final show.

Theodora seemed to dance just for Billy at her final dance. She ignored the other front row jockeys to play only to Billy. He was rock hard throughout her act and the bulge in his pants was clearly visible to Theodora as she kneeled to jiggle her beautiful breasts at Billy, sitting about three feet away. She managed to whisper "See Rocco, after the show," and hummed as she danced away, to pose naked at the curtain, ending her act. Billy was dumbfounded. He wondered if he had misunderstood her and heard only what he wanted to hear. Billy rose to leave, only to see Rocco waiting for him in the lobby.

"Hi ya, Billy," he said putting his arm around him. Billy was frightened that perhaps he had angered Rocco, or that Theodora had told him he had a hard-on when she was dancing. "Don't worry, Billy, everything is cool. Come with me," Rocco said as he guided Billy out of the theatre to a huge black Cadillac parked in the no parking zone in front of the theatre. "This could be your lucky night, Billy me boy."

Billy was ushered into the back seat next to an older man impeccably dressed, who spoke with an accent. "Ok, Rocco, it's all right." The older man ignored Billy and his attempt to say hello. He just stared straight ahead. After a few minutes of silence, the front door opened and Theodora got in the front seat and Rocco drove away. They rode for nearly an hour until Rocco pulled into an apartment building that had wealthy written all over it. He stopped at the entrance and a doorman opened the door to let Theodora out. She turned and opened the back door and offered her hand to Billy who, in a daze, clasped her hand and got out of the car. The older man said something in a foreign tongue and looked at Theodora and uttered "Call me, later." Rocco and the older man drove away.

"Are you hungry, Billy? I make a great breakfast if you're hungry," Theodora told him. Billy declined and asked where he was and how would he get back home. He was worried that if he didn't get to the station soon he would miss the bus. Theodora, grinned and said to Billy, "Honey, you're at my apartment and don't worry, Rocco will come back and drive you home when you're ready to leave," she reassured him. Billy looked about at the elegant and spacious apartment in amazement. He had only seen such splendor in the movies. "Nice, huh," said Theodora as she took his hand and led him into her bedroom. She sat down on the king size bed and had Billy stand in front of her. Billy was very uncomfortable and it showed. Theodora unbuttoned his shirt and she felt him trembling at her touch. Just then she suspected that perhaps Billy was still a virgin. "Billy, have you ever been with a girl or woman before?" she asked as the shirt fell to the floor.

Billy's mind raced to find the right answer but all he could is stammer, "I…I…I once felt a girls breast at the movies," he blurted out, embarrassed.

"Oh, I see, honey, you have never had fun with a girl naked and just you alone with her, right?" Theodora asked him, as she undid his belt and began to pull his pants down. Billy shook his head 'no' and Theodora smiled at him. "Well, don't worry, honey, we all have to have a first time for everything." His pants fell in a heap at his ankles and he stood only in his Jockey shorts. His cock was steel hard and pushing at his shorts. "That looks nice," she said, as she looked straight at his bulging shorts, "can I see it without your shorts on, Billy?" He nodded and trembled as she hooked her thumbs in his shorts and pulled them down. His cock sprang out, pointing straight up. His cock was nearly seven inches long, uncircumcised and his balls hung low, but drawing up. "Oh my, that's lovely, Billy. May I touch it?" she asked. He nodded as Theodora reached out and gently grasped his cock and squeezed it gently, forcing the blood from his cockhead to prevent Billy from cumming. He groaned at her touch and could not believe that this was actually happening to him with his 'Goddess'. A large clear drop of thick pre-cum seeped from his cockhole. Theodora wiped it up with her forefinger and licked her finger clean, "Umm, virgin pre-cum tastes better than any other pre-cum, Billy."

Billy's legs were shaking and Theodora laid him down on her bed. He lay naked looking at her as she stood and removed her dress. She reached behind her and undid the lacy bra that held her magnificent tits prisoners and let it fall. Slowly she pulled her panties down and stepped out of them and climbed into bed with Billy. Again she gently squeezed his cockhead to preclude his cumming prematurely and slid her naked body next to his. Theodora sat up against the soft pillows and brought Billy's head to rest on her breast. "Do you like my breasts, Billy?" she asked.

"Yes," Billy said softly, "they're so soft and warm." She raised herself up and placed his face between both breasts. Billy moaned, as he smelled her perfume and his mind reeled with excitement. Without thinking he kissed her breasts all over and rubbed his face in them blissfully. She sighed as she brought a nipple to his lips and asked him to lick it. Billy licked her breasts as she held his head and kissed his forehead. Instinctively he pulled her nipple into his mouth and began to suckle her.

"Umm, that's so nice, Billy. Suck it harder and gently bite it and pull it with your teeth," she said as she closed her eyes to enjoy his tongue. "Lick the other nipple too, Baby," she told him. Billy moved his mouth to her other breast. He showered it with kisses and bathed it with his tongue before sucking it into his mouth to suckle, gently bite and pull at her nipple with his teeth. Theodora moaned in pleasure as she held him tightly and 'nursed' him. After some time had passed, Theodora rolled Billy on his back and lowered her mouth to his nipples. Billy was dumbfounded as she licked his hard little nubs. He could feel her tongue licking them and a strange feeling throbbed in his cockhead. "Like that?" she asked as she resumed tonguing his nipples without waiting for his response. His moaning and labored breathing told her all she needed to know.

She rose up and gently took his cock in her hand, squeezing his cockhead, and pulling his foreskin back to reveal his purplish pink and bulbous cockhead. He was straining not to cum and she recognized the signals easily. Her hand moved down to cup his balls and she rippled her fingers around his balls. Her head moved to his groin and she kissed the tip of his cock and licked up another thick drop of pre-cum that had oozed out. His cock throbbed as she realized that he would cum soon regardless of her efforts to prevent it. She covered his cock with her mouth, closed her lips about it tightly and licked his cockhead all about. Billy tried not to cum, but overwhelmed by his 'Goddess', he erupted in a massive orgasm spewing his thick white virgin cum deep into her mouth. Theodora moaned in delight as she swallowed his cum and continued to lick and suck his cock. His cockhead was so sensitive to the intensity of her tonguing that he sought to pull out of her mouth because he couldn't stand it. Suddenly his orgasm peaked with ecstasy and he relaxed limply onto the bed sheets. Theodora continued to lick and suck his semi hard cock and moved to lick and suck his balls. After a few minutes of her oral treatment, Billy was hard as a rock once again.

"Would you look at that," cooed Theodora, smiling at him, "you're ready to go again aren't you, sweet Billy," she nuzzled his pubic hair with her nose, rose up and kissed his lips deeply. He felt her tongue enter his mouth and roll around his tongue. There was a new taste in his mouth and he realized that it was his cum, still on her tongue. Billy didn't care. He loved every minute of being with his 'Goddess' and he returned the kiss with equal fervor. She lay down beside him as Billy began to lick and suck her nipple again. She pushed her breasts together so that Billy could take both nipples in his mouth at the same time. "Your cock tasted good, Billy," she moaned as he sucked both her nipples, "you're a fast learner, honey." She took his hand and moved it down to her bush. He played with her bush for a few seconds, then his fingers dipped down to her wet pussy. Billy instantly pulled his hand back and released her nipples.

"Did…did… did you pee?" he asked sheepishly. Theodora laughed and shook her head.

"No, silly, I didn't pee. You just put your fingers in my juices," she laughed.

"What…juices?" stammered Billy.

"Billy," she explained, "a woman produces juices to lubricate her pussy for intercourse," she explained, "If we didn't, then it would hurt for both of us when we fucked."

"Are we going to fuck too?" asked Billy.

"Oh yes, darling, we surely are going to fuck our brains out. You're virgin cock will be a professional before this night is through, Billy," she took his hand and put it on her pussy again. Gingerly, Billy explored her wet cunt with his fingers while Theodora sighed with pleasure. He pushed his finger into her cunt and felt the soft velvety inner flesh of her cunt. Billy got on his knees between her legs and lowered his head to look at his first ever cunt. She smiled in amusement at his inquisitiveness and at his virgin inexperience. She reached between her legs and brought his hand to her engorged and erect clit. "Rub this little nub, honey." Billy drew his wet fingers over her clit. She moaned and gasped from the delightful sensation. "That's my clitoris, or clit, Billy. It's the center of pleasure for a woman," she moaned as his finger flicked back and forth across it. "Do this, Billy," she told him as she put his fingers on either side of her cuntlips to trap her clit between her cuntlips. "Now move my pussylips up and down on my clit with your fingers, Billy. This will stimulate any woman, darling. It's how I like to masturbate," she moaned as he did her bidding. "Sometimes I rub myself or push my fingers inside, but I like this way best."

Theodora writhed and gyrated as Billy masturbated her. Her eyes closed as she moaned and gasped delightfully as her young lover pleasured her. Her clit was so sensitive that she snapped her head from side to side as he continued to 'torment' her sweet clitty. Billy could feel her trembling as he played with her clit. Her moans were long and drawn out as her body writhed. Suddenly, she cried out and convulsed as she erupted in a thunderous orgasm. Again and again she would buck, jerk and cum as she sighed, gasping delightfully. Her juices drenched his hand, but Billy continued to rub the sensitive nub causing her to experience one orgasm quickly followed by another. Finally, her orgasms subsided and she pulled Billy up to kiss his mouth.

"That was fantastic, lover," she gasped and kissed him.

"Are you all right?" Billy asked unaware of what had just happened. Her writhing, moaning and shuddering had frightened him, thinking that he was hurting her.

"Oh yes, Billy, I'm more than all right. That was awesome…absolutely incredible," she reassured him. "That is how a woman cums if she's properly made love to. Women have orgasms too, Billy. Some of us even squirt out some juices, just like I did, but we all get wet when we cum," she explained. Billy was astounded. He was unaware that women masturbated and he didn't know that women had such powerful orgasms. He had heard rumors, but he thought it was just tales without any basis in truth. Tonight he had learned differently. Theodora put a large pillow under her ass and raised her hips up. Billy could see her wet cunt easily now. "Billy," she began, "I want you to lick me down there on my pussy, just like I licked your cock," she told him. Billy had second thoughts about that. His friends had told him that it was not a thing that men did, because it was dirty. He balked momentarily as Theodora grasped his head and gently, but firmly, brought his head between her legs. Billy inhaled her scent and found the fragrance of her cunt pleasing and alluring. "Please, Billy," she implored him.

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