Sorry Sissy You Lose Pt. 04

Slave had been busy. Spending hours looking online for things for his Mistress. His little dick always swelling and throbbing as he went through pages of web sites, looking at heels, lingerie, hose, dresses, jewelry, etc. Mistress had tasked her slave. He was to purchase various outfits for her to wear on an upcoming trip. A work trip for his Mistress, but her well hung, older lover would be at the same conference. And slave knew that Mistress' pussy would be wet for him, all day, all night, every day of the conference. Slave also knew his little dick would be easily excitable, dripping precum at the thought of his Mistress enjoying her lover.

Slave had bought some high end lingerie for Mistress. It cost him a pretty penny, but he imagined Mistress strutting her sexy body in it at the conference, in the hotel room of her lover. The thought of slave buying her expensive lingerie she wore for her lover made his little dick hard... he often stopped to play with himself as he looked at the selections of lingerie online, imagining Mistress and George, her wet pussy and his hard cock... while slave's little dick would be tucked tightly in lace panties... ignored, untouched, denied.

On a good day slave's dick was 5 inches in length. On his best days. But the real problem was the girth. Or lack thereof. Slave's little dick was thin. Needle dick thin. The kind of thing that caused his Mistress to request him using a dildo with his dick when fucking her. He could not fill her hot pussy, let alone stretch it, with his little dick. Contrast this to George's big cock. Mistress said his cock was very thick. Pop can thick. Mistress said George's cock would stretch and fill her little pussy, that it would hurt at first until she stretched around its girth. But slave knew she would take his cock. Balls deep. He had seen her fuck other big cocks. Sure, it started with Mistress sucking both her slave and her lover's cocks. But eventually Mistress spent more time, more focus, on her lover's larger cocks and balls, first stroking her slave's dick and then holding it while she worked her oral magic on the other big cock, but ultimately ignoring it while she focused her attention on the new cock before her.

Slave couldn't blame her or be angry. He felt how wet her pussy got as she sucked those big cocks. He watched her pussy stretch around those cocks, and then coat them glistening wet with her juices as they pumped in and out of her. He heard her moans and dirt talk as she fucked her lovers.

Of course his reward for buying her sexy things to wear, for arranging the play dates, for being a good sissy cuckold, was licking her pussy clean after another cock fucked it so good and shot hot cum deep up inside his Mistress. He smelled their cocks, he tasted their cocks, he tasted all of their cum. All on and in her pussy. His little dick always got hard as he licked and sucked their cum out of his Mistress' pussy. And when he was fortunate enough to put his little dick inside his Mistress pussy after it was well fucked and cummed in, he was reminded time and time again of how small he was, in length and in girth. He could feel her wetness, but not her walls, it was not tight, and he knew she could barely feel his dick.

Slave bought his Mistress some heels, lingerie, and jewelry for her pending trip. He pleased his Mistress with the choices he bought. She tried them on and modeled them, teasing her slave by sending him hot pictures. And one night she strutted an outfit slave bought for her, making him crawl, making him beg, reminding him how little his "teenie weenie" was. After licking her pussy, kissing her feet and legs, after being his Mistress' little sissy toy to play with, slave was rewarded by Mistress. She granted him permission to fuck her.

As they began to fuck Mistress asked slave if he thought George would like the outfit she had on, the outfit slave bought for Mistress. "Yes, Mistress" came her slave's quiet reply.

"Slave, do you think George will want to fuck me in this outfit?" Mistress asked.

"Yes, Mistress. Very much so" replied slave. And his little dick got rock hard as he heard his Mistress whisper "George, oh go slow, you're so much bigger than what I'm used to, George. His dick is much smaller than yours. Oh George yes" Mistress teased her slave with her dirt talk.

Slave felt his Mistress get so wet all over his dick as they fucked. He knew Mistress was imagining fucking George during the conference. Her moans got louder, her breathing quickened.

"Mistress yes, fuck him. Take his big cock balls deep. Give George every inch of your pussy he needs to milk his cock" slave said as they continued to fuck.

And that's when it happened. For the first time. Ever. Mistress squirted! She came so hard, so loud, so incredibly sexy, she squirted all over her slave's little dick and balls. A puddle was on the bed as her legs shook and she mumbled something about squirting.

Slave was so turned on. His Mistress had never squirted before. He knew his Mistress would be beyond wet for George at the conference. He wanted George to make his Mistress cum. Hard. Fast. Repeatedly. He wanted George to make Mistress squirt...

During their most recent training session Mistress laid on her bed, spread her legs wide, and told her slave to lick her pussy after kissing it. Of course slave obliged, licking her slowly as instructed.

"Slave do you want me to fuck George?" came his Mistress' question as he was busy lapping her pussy and rubbing her legs.

"Slave seriously - do you want me to fuck him?" Mistress asked her slave.

"Yes, Mistress. Yes please I want you to fuck George" slave responded.

And with that Mistress grinded against her slaves' face and then came all over his face as she thought of fucking and sucking George at the conference...