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A Sissy Boy is Made

12

Edited by goamz86

For those interested this is an in-depth background story of sissy boy Greta who was introduced in Chapter 8 of Black Mistress-White Bitch. Please, if this scenario offends you please find other material to read.

*

By any measuring stick Greg Martin was a wimp, and a very submissive wimp at that. His wife of 14 years, Jaclyn, had discovered this even before the two of them were married. Actually, Jaclyn wouldn't have taken a second look at Greg, as most women didn't, had it not been for his submissive nature. If one thing could be said about the full figured and beautifully curvaceous Jaclyn it was that she was a powerful and dominating woman.

Jaclyn knew exactly what she wanted and wasn't above taking it. Those that worked for her called Jaclyn a real bitch. That was behind her back of course. At any rate, she asserted her authority over Greg from the very moment they met.

Jaclyn's father owned a mortgage brokerage firm that she ran when Greg met her. Greg had answered an ad for a job as a file clerk. Having lost his job as a bank teller almost six months before entering Jaclyn's office, he was desperate for any work he could find. Being 26 years old at the time, Greg felt the job was beneath him, but his bank account was dangerously low and if he didn't find something soon, he would be out on the street. He was hired by Nancy, Jaclyn's second in charge, and had been working for the company almost a week before he ever laid eyes on Jaclyn.

Considering his submissive nature, it was only proper that he'd be kneeling the first time he met his future wife. Greg was in the file room on his knees filing some papers in a bottom drawer when she walked in. He looked up to see who was standing over him, and blushed beet red with embarrassment as he gazed upon Jaclyn's big boned elegance. Looking down to take her in again, he saw she wore the sexiest spiked heels, and her shapely nylon covered legs disappeared under the hem of a tight fitting skirt that stopped a good nine inches above her knees. Tucked into the skirt was a sleeveless silk blouse that hugged her round belly and held in the biggest set of breasts he had ever been so close to. As he looked passed her chest to her face he noticed her beauty. All her facial features were small but fit nicely onto her chubby face. What blew him away the most, were her gorgeous aqua-blue eyes. He wished he could look into them forever. He was utterly stunned and nearly speechless as this beautiful, voluptuous and down right sexy woman stood over him.

Greg began to stand.

Jaclyn stopped him short with a hand to his shoulder as she good naturedly quipped, "No need to stand, honey, I actually enjoy the sight of a man on his knees."

Greg's face burned hotter with embarrassment, and his manhood stirred to attention in his loose fitting slacks, as he thought that somehow this beautiful creature had sensed his deepest, darkest secret.

In her arms Jaclyn carried a very large stack of files. She smiled dryly as she realized she was being checked out. Then a bit callously Jaclyn introduced herself, "Hello, we haven't met but I'm Jaclyn the boss' daughter and office manger. You work for me. And your name is?"

"Uh, um, ... er ... it's Gregory." He stumbled with his answer.

Gregory didn't understand it. He never referred to himself as "Gregory". Only his mom ever called him that, and even then only when she was mad at him. However, it felt appropriate to tell his new lady boss that his name was Gregory. He tried his best to control the nervous excitement inside and the tent that was building in his pants.

Jaclyn didn't even offer a handshake, only a terse command and another smug smile, "Here, file these for me, Gregory."

No "please", no "thank you" simply, "file these," which Gregory would soon learn was classical Jaclyn.

"Ye ... yes, Ma'am, I can do that," Gregory replied without hesitation.

He wanted to stand and take them from her, but he didn't dare. If he did, she was sure to notice how aroused he was, because his cock was now throbbing in his pants.. His failure to stand and lessen the gap between them meant Jaclyn had to bend over to hand Gregory the files. As she did that, he failed to pay attention to the stack of papers when her blouse fell open a bit giving him a clear look at her immense cleavage and a black silk bra. She noticed his stare and deliberately spilled the entire stack of files all over the floor.

"Oops." Was all Jaclyn said.

Hoping to gain approval Gregory quickly responded awkwardly, "Ah ... don't ... don't worry Ma'am I'll get them."

Smiling again, Jaclyn patted Gregory on the head as she said condescendingly, "Oh, sweetie, I'm not worried at all." Then she abruptly turned on her heel and left the room with Gregory still on his knees. Jaclyn couldn't help but giggle to herself as she exited the file room, knowing that Gregory was smitten with her, and how he had almost apologized to her when she had been the one to spill the papers all over the floor. She intended to take full advantage of this situation.

Over the next few days, Gregory found any excuse he could find to be in the presence of Jaclyn, and this didn't go unnoticed by her. She took every opportunity to tease and otherwise embarrass Gregory. She would often tease him a bit by leaning forward to give him a look down her top. She even rubbed her big round bottom up against him a few times when they happened to be in tight quarters. Jaclyn's playful verbal jabs gave him hope that maybe he could have a relationship with her, but he was too shy to actually ask out such a powerful woman. Jaclyn thought nothing of her teasing, but Gregory lived for those little exchanges.

One evening, after a really good month at the brokerage, Jaclyn invited the whole office to a local bar for drinks and appetizers. The drinks flowed and everybody got loose and was soon having a great time. Jaclyn teased Gregory mercilessly over and over right in front of the entire group.. Time after time Jaclyn sent Gregory to the bar to retrieve yet another round of drinks for the table. Jaclyn took great delight in using Gregory as her own personal waitress. Gregory understood the demeaning position he was being put in, and how everyone in the office would now view him. However, he couldn't deny her or the sexual excitement that stiffened his male rod as he did everything she asked.

By 10 P.M. the office crowd had all gone home. That was when Jaclyn, with something of a smug smile, invited Gregory to her house for a little private time. She figured she could have a little fun with the shy little guy and make his day, and if all went well, she could get laid. Of course, Gregory was thrilled (and blushed accordingly) at being offered such an opportunity and accepted without hesitation.

The cab dropped them off at her home and they went in. It was a very nice home, and Gregory noticed how well it was decorated. One thing led to another and the two of them ended up naked and in Jaclyn's bed. Gregory always feared these situations, because even fully erect, his cock was only 3-3 ½" inches long and less than 2 inches around. Nonetheless, he was drunk and his inhibitions were gone. So he did as he always did in these situations. He made sure he satisfied his lover with his tongue, because he knew he would never be able to do it with his cock. He marveled at the size of her tits, and enjoyed every second that he was allowed to play with them. When he had satisfied his tit fetish, he performed his favorite task of all, eating pussy. He loved it so, and it showed. He devoured her big, fat, juicy hair covered snatch, and brought her to three orgasms before Jaclyn told him that was enough and that she wanted to suck his cock.

Not thinking, he jumped at the chance to have his tiny cock sucked. He rolled over on his back and watched as she got on all fours to perform her blow job. Her big heavy breasts dropped from her chest and he watched them sway back and forth as she crawled up his body toward his manhood. When she reached for it in the dimly lit room, she couldn't help but let a chuckle escape her lips when she took a hold of it. Embarrassed beyond words, Gregory covered himself and rolled over.

"Oh come on babydoll, don't be that way, I think it's cute. I wanna see it again." Jaclyn told him, still giggling. "I promise, I wont laugh again, and I promise to suck it if you let me see it again."

Not wanting to waist an opportunity for a blow job, Gregory rolled back over. His cock had gone soft from the embarrasment, and now was no more than a couple of inches long and even skinnier than before. Jaclyn grabbed it with her thumb and first two fingers and began to stroke it back to life.

"Look sweetie, I can jack it with just three fingers." She teased him. "Does that feel good?"

"Oh yes!" Gregory moaned as his pleasure instantly returned, as did his little erection.

"It's just so cute." She repeated in a voice she usually reserved for speaking to children.

Gregory's cock just got harder with every word from her mouth. Jaclyn noticed this and realized he must be like those men she had read about with a fetish for being humiliated. So, she went with it.

"Does that feel good Gregory?" She asked again in her baby voice. "You like it when Jaclyn strokes your little pee pee?"

"Yes! Yes it feels wonderful" he replied.

"Would you like me to suck that little pee-pee?"

"Yes, Please. I would love that," Gregory replied eagerly.

Realizing the very dominating position she had gained, she suddenly change and said in a demanding voice, "Beg me!"

"Please, Miss Fellows. Please suck my cock." He begged. Gregory couldn't even believe he was getting off on the humiliating treatment Jaclyn was giving him. However, the hot pre cum leaking from his throbbing dick didn't lie.

"I like that." She told him referring to what he called her. She was two years younger than him, yet he was calling her Miss Fellows. "I like a lit' boy that knows how to show proper respect."

"Say it again." she commanded.

"Please suck my cock Miss Fellows" he asked shyly, his cock throbbing with excitement.

"Cock? Sweetheart, this is in no way a cock. A cock doesn't get stroked with three fingers. A cock wouldn't disappear in my hand like this one does." With that she grabbed hold of his shaft with her entire hand. The only thing visible was the little mushroom head. "A cock is big and thick and is used to fuck. This right here baby, this is a penis, a little penis, a penis that a 7th grade boy would be ashamed to have. This is definitely not a cock."

Gregory should have been embarrassed to hear such things. His cock should have shrunk from the humiliation, but all it did was throb harder. She was now short stroking it with her whole fist, running her palm over the sensitive head making him almost cum each time.

"Now if you want Jaclyn to suck it, You're gonna have to call it what it is, OK?"

Gregory nodded.

"Now ask Miss Fellows again." She said, returning to the baby talk.

"Please Miss Fellows, please suck my penis." Gregory begged.

"Your what penis?" She asked.

"My little penis. Please suck my little penis." He asked again.

"That's better." She replied

Jaclyn finally lowered her head to his little cock and put it in her mouth. She sucked it up and down about four times before he informed her he was about to cum. She immediately removed it from her mouth and let his orgasm subside.

Over and over again Jaclyn skillfully used her tongue and mouth to bring Gregory to the very brink of orgasm. She found it amusing that she could put its entire length in her mouth without it even reaching the back of her throat. She was sure she could even fit his balls in her mouth as well. She didn't try, but she was sure she could. She just continued to bring him oh so close to orgasm over and over. Yet each time he neared completion she would cease her efforts and giggle to herself at Gregory's misery. There was no doubt she was enjoying the power and control she had over him. The continued torment was more than Gregory could stand. Soon he began to beg for release. Gregory knew it was humiliating to beg for his pleasure, but he couldn't help himself. He wanted to cum and he would do anything to achieve it, even beg for it.

Jaclyn smiled smugly as she pulled her mouth from his tiny organ denying him his release. That twenty-five minutes of torment would be the very last time she would ever suck his cock.

After waiting a short time for his approaching orgasm to wither, Jaclyn repositioned herself on her back and spread her legs. "Think you can satisfy me with that lit' pee-pee of yours Gregory," she demanded to know.

Fearing that he himself might be sent away less than satisfied Gregory quickly stammered, "Ohhhh yes ... yes I can satisfy you."

"I doubt it, you lit' wimp., but give it your best shot. Come up here and give Miss Fellows all you got. Fuck my brains out with that little thing." She told him in a voice dripping with sarcasm.

Jaclyn's degrading words heightened his arousal as his tiny man tool stiffened further. Excitedly, he jumped on her and slid his teenie cock all the way in, and began eagerly pumping her pussy as best he could.

Jaclyn giggled out loud, "You're tickling me, baby doll." "Come on, is that all you got sweetie?" she teased him, only turning him on more. "Fuck me, you bitch, fuck me like you mean it," Jaclyn urged.

Gregory pumped harder and tried futility to go deeper. His masterful performance was laughable, as it was only about a minute and a half before he unloaded his steamy hot cum inside her accepting pussy. He collapsed on top of her in complete exhausted satisfaction.

Jaclyn patted him on his head as he lay panting on her chest, and in a comforting voice she said, "That's OK baby, Miss Fellows didn't expect anything more than that. You tried your best."

Once again Gregory wasn't embarrassed by her condescension; He was turned on by it. They lay there for a few more minutes before Jaclyn sent him on his way in a taxi. The taillights of the taxi hadn't even disappeared from view before she was on the phone calling a real man to come over and fuck her right.

That was the first of only 16 times that Gregory has been allowed to fuck Jaclyn to date. The next time he was allowed pussy access was their wedding night, then each year after that on their anniversary.

The day after their first sexual encounter Gregory found himself in Jaclyn's office fearing he was going to be scolded, or worse, fired. To his surprise, he ended up under her desk eating her pussy for more than an hour as she conducted business on the phone. Their relationship grew from there and so did Jaclyn's domination and humiliation of him. Gregory often found himself on his knees between her fleshy thighs as he licked her to one fantastic orgasm after another. This happened whenever the urge compelled her: at the office, at her home, even once in a bathroom at a restaurant where they were having dinner. Gregory loved proving his love for her in this way; He was totally devoted to her. Little did he know Jaclyn was not as loyal. She spent many nights out getting hammered by men with big fat cocks as Gregory sat at home alone believing she was at dinner meetings for work.

Over the next three to four months Jaclyn introduced her lap dog Gregory to many new things including butt plugs, strap-ons, and cock cages. Just a week into their physical relationship Jaclyn demanded that he begin wearing a chastity device which locked around his less than masculine cock. The devise caused a great deal of discomfort whenever Gregory became aroused. And, of course, Jaclyn held the only key. She quickly became addicted to the erotic power she had over the submissive little wimp and she found every opportunity she could to wield it. She loved watching him wince in pain from his cock cage by arousing him. She would call him to her office during the day and make him guess what color bra and panties she was wearing. Then she would open her blouse and show him. He little cock would get rock hard and he would buckle over in pain. If she was feeling really naughty she would lift her skirt and show him she was not wearing panties at all, then make him watch as she fingered her fat juicy cunt for several minutes, then feed him the juices from her finger. She just ate up the feeling this power gave her.

Jaclyn soon realized that she would never find anyone more devoted, loving and obedient than Gregory. Besides, she knew very well that her urges for big fat cocks could be filled elsewhere. With that in mind, and without bothering to inform him, she began to plan their wedding. The day she mailed out the invitations Jaclyn had her strap-on buried deep in Gregory's ass-hole when she decided to tell him they would be getting married. She laughed smugly as he promptly shot his hot load of cum all over the floor because he was so excited by the news.

"Should I consider that a yes, Gregory?" Jaclyn intoned sarcastically, as she drove her strap-on in deeper and harder,

Gregory bucked furiously, jamming his hips back to meet Jaclyn's powerful assault as he attempted to take every last inch of her fake dick and he hollered, "Yes my love, yes I would love to marry you!" Then he just repeated over and over, "I love you, I love you, I love you."

As if there was ever any doubt, Jaclyn stated coldly, "Then it's settled your going to be my bitch." With that she slapped his left ass cheek hard as if emphasizing her words.

As Jaclyn repositioned herself so Gregory could use his talented tongue on her oh so ready and juice cunt, Gregory realized it was true. She was sitting on the edge of the bed when Gregory kneeled between her soft, creamy, white thighs and drove his tongue straight into her gaping love hole.

'Yes,' Gregory thought, 'there is no doubt that I am the bitch in this relationship.' With that thought, Gregory's teeny weenie began to stiffen again.

Gregory was wearing a cock cage and a big fat butt plug the day he pledged his love and devotion to Jaclyn on their wedding day. She patted his ass repeatedly that day reminding him how it would be. Jaclyn had made two of her lovers groomsmen, telling Gregory they were her cousins. When she told Gregory she needed their help in the bride's room after the ceremony he never suspected she was fucking and sucking them like the big cock whore she was. Gregory had no idea he was licking their cum from her pussy that night before Jaclyn permitted him to fuck her for the second time. He was so excited about getting laid that he just though her extreme wetness meant she was very excited as well.

During their four-week honeymoon, Jaclyn took every opportunity to embarrass and humiliate Gregory in public. Jaclyn made sure that while in public everyone knew exactly who the boss was in her marriage. Her first demand was that Gregory always refer to her as Miss Fellows (Jaclyn wasn't about to take some wimps surname) whenever they were in a social setting. Of course, the abuse only heightened Gregory's constant arousal. This only added to his endless discomfort, as he was always required to wear his chastity device.

They were on a shopping trip the third day of their honeymoon when Jaclyn had a sudden and very evil thought and chuckled to herself.

"If you're going to be my bitch I suppose you should dress the part don't you think, baby doll?" She asked Gregory.

What bothered Jaclyn was the fact that she hadn't had the wicked idea sooner.

Momentarily, Gregory was absolutely flabbergasted, for as submissive as he had been all his life, he had never thought about the prospect of cross-dressing. He gasped in pain as his tiny pee-pee stiffened inside the cock cage he was wearing.

12
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