tagFetishSissy Boy Secretary Ch. 06

Sissy Boy Secretary Ch. 06


When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see.

"Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she gave them to her. Elaine took the items, "That's a good little Slut." Elaine then reached under Lisa's short skirt and put the first stocking in her pussy.

"Now Sissy Boy, remove that stocking." I crawled over to Lisa, and took the now soaking wet, as Lisa was obviously pretty excited, stocking from her pussy. This was repeated with the other stocking and then the garter belt. I now had all the soaked items in my mouth.

"Okay now Sissy Boy time to finish dressing." I started to put the stockings on when Elaine informed me to properly dress that I should remove the jacket. My cock was rock hard standing in this parking garage with cum soaked stockings and garter belt hanging from my mouth, handing Elaine's jacket back to her. Elaine stood there caressing Lisa as I finished dressing, in my panties, stockings and garter belt. My thong panties doing nothing to hide my red freshly spanked ass, or my excitement as the front of the panties were sticking straight out.

I was then placed in the car, in my outfit, in between the bucket seats with a knee on each seat and my head on the back seat. In this position my ass was on display as we drove over to Elaine's place. Elaine had Lisa spank my ass at every red light and stop sign, so by the time we got to Elaine's my ass was again on fire.

I was left on Elaine's doorstep as Lisa and Elaine went inside. While I was there the Mother and daughter next door looked over and laughed, as they had seen sights like this before. I hadn't noticed the camera that they had, but I would find out later. That is a totally different story for another time though.

After what seemed like forever, although it was only ten minutes, Lisa opened the door wearing a big black strap-on dildo. It must have been at least 10" long and about 3" around. My eyes must have given away to my fears as Lisa said, "Don't be such a sissy and get your ass in here!!" As I stepped past Lisa and through the door....SMACK......I had been struck right on my already sore ass by a riding crop that I didn't see in Lisa's hand. Perhaps my mind was distracted by the implications as to what the day might bring as I stared at the black monster hanging so menacingly in front of Lisa.

"On your hands and knees Sissy Boy, just like you know how!" Lisa responded as I quickly got on all fours wanting to avoid further slaps to my already on fire ass. Photos of the incident would show up later to haunt me.

I continued crawling into the living room to where Elaine was lounging on the couch, drink in hand. I did endure three more swats from the riding crop as it seems I was too slow. Once there, I was ordered to kneel at the side of the coffee table that sat in front of Elaine. I was lying over the center of the table as Lisa grabbed one then the other wrist and tied them to the legs of the table. I was stretched to the limit and my ass was quite exposed to Elaine. My now ever hard cock was pressed firm against the table causing quite a discomfort. My knees were then secured to the other legs of the table, stretching them wide.

Elaine started to rub my ass all over, "What a cute ass you have Sissy Boy. I do indeed like it this shade of red," as she slapped it. "You like that Sissy Boy, your red hot ass getting groped by your Mistress?"

Ummmm!!! "Yes Mistress I deserve to have my ass reddened when I do not please you." I stammered in between Elaine's caresses and slaps.

"That's very good Sissy Boy, I do love it when you obey," said Elaine as she moved Lisa between her legs to please her. "UUMMMMM!!! You are almost as good as Sissy Boy Lisa; we will work on that later though. UUUMMMM!!! For now its time to further Sissy Boy's training."

Unable to see but able to clearly hear Elaine moan with pleasure derived from the expert tongue of her newest secretary, was driving me crazy. My cock attempted to get harder but within the confines of the panties and being crushed to the edge of the table just made it hurt more. Squirming around trying to get a look at the scene behind me only caused my cock to be jabbed into the table's edge, bringing about short stabs of pain.

My excitement grew as I waited for Lisa to satisfy Elaine. The moans slowly became louder and quicker as I heard Elaine scream with what was obviously an awesome orgasm.

Regaining her breathe Elaine ordered Lisa to go kneel in front of my face showing me her toy. Lisa did as ordered and even took the opportunity to slap my face with it a couple of times. This brought about a little giggle from Elaine who was enjoying my predicament.

"Are you ready to start your training Sissy Boy? Are you ready to further serve me?" Elaine asked.

"Yes Mistress, I am ready to serve." I replied quickly as not to receive another spanking.

"I know that in this day and age I should not feel the way I do but I just can't help how I feel. I was pretty much raised by my Grandfather and Grandmother when I grew up. In their day it was wrong for a white woman to be with a black man. Although I know it is wrong I still cannot get over the feeling that it is wrong and nasty for me to have sex with a black man. This brings me to my problem; I need to find a way to reward all the janitors in the office for their hard effort every day. I have hired this janitorial staff because they are the best around. They all just happen to be black. They are a truly great bunch of workers and I have the utmost respect for them. I have never had a complaint on the work that they do. This is why I am so adamant on rewarding them."

Elaine was now standing behind me, leaning over and reaching in between my legs to grope what was accessible of my cock. Lisa and Elaine both seemed amused at my inability to remove my eyes from the big black dildo now only inches from my mouth. Both ladies giggled when Lisa rubbed the menacing member across my lips. They mistook my fear to be pure desire as I stared right at it.

"I told you that Sissy Boy would like this didn't I Lisa? Just look at her stare!" Elaine stated, "And her little cock is so hard right now." She continued to rub and pinch the head of my cock as it peeked out from under the table. The edge of the table was still digging into my cock as I squirmed under Elaine groping. Elaine slapped my ass a couple of times then moved to the other side of the table, right next to Lisa.

"That is a big nasty cock you have there Lisa. It looks so naughty doesn't it?" Elaine said as she rubbed the dildo over my lips. "What do you plan on doing with it Lisa?"

"Well," Lisa said, "I think Sissy Boy needs to learn how to service a big black cock since it is too nasty for you or me to do." My eyes lit up at that last suggestion. "Just look at how eager Sissy Boy is." My tongue had inadvertently started licking the dildo as Elaine pressed it into my lips. I knew exactly where this was going and I was in no position to argue at this point, so I gave Elaine what she wanted, a black cock slut. My mouth started to open but Elaine skillfully left the dildo just out of reach.

"Do you want to please me Sissy Boy? Would you become my black cock whore so I can better my business position in the world?" I digested the statement but thought it odd since she said I would be rewarding the janitors. "Oh doesn't she look sweet opening her mouth to please me. That is so delicious to see. I need to do something for you now," with that Elaine took the strap-on into her wet pussy to cover it in her juices, "Enjoy this just this once Sissy Boy since it will never happen again!" Taking the dildo out of her sweet pussy, the juices shining in the light, Elaine turned Lisa to place the strap-on into my open and waiting hungry mouth.

Although I did enjoy the taste of Elaine's cum, that coated the big black dildo, I did not like the idea of a black cock in my mouth in front of these two obviously hot ladies. It was then that I noticed the presence of another person in the room. Out of the corner of my eye I could make out the figure of a very young girl with a video camera in hand, catching all the action. I found out later that this was the daughter from next door and that she was indeed 20 years old but only looked younger. (This video will be used in further adventures of Sissy Boy.)

As Lisa literally fucked my mouth with the big black strap-on Elaine bereted me continually. "Suck that black cock Sissy Boy!!! Yaa that's it, suck it good. You are such a little slut!!!"

"What a little slut you are with that black cock in your mouth, how nasty is that?" Lisa retorted, as she continued to make me gag on the strap-on, driving it deep then pulling out to do it again.

"I think our Sissy Boy likes it nasty huh? Suck that nasty black cock whore." Elaine said. "What nasty girl would ever suck on a black cock, how nasty?"

Elaine moved behind me and started spanking me. "You are such a naughty little Sissy Boy!! Sucking that nasty black cock and enjoying it!!" she laughed at my predicament. I tried to shake my head no but was unable to as my mouth was pretty well occupied at the moment.

The humiliation as to what I was doing was driving me mad. Being spanked and having a fake black cock driven into my mouth was too much. I was even more humiliated as I erupted into an explosive orgasm, the cum dripping down my thighs.

"Damn Sissy Boy, did you just cum?? You do like this don't you?" Elaine said as she retrieved the cum from my thighs and let it drip onto my ass.

"That was sooo hot!!" said Tammy, (the daughter from next door), "I can't wait to show this to my Mom, she'll love it!! You be sure to let me know when I can borrow Sissy Boy for a long weekend. Mom and I would have so much fun," not waiting for a reply Tammy went to the door, "Bye and thanks again."

Borrowed for the weekend, what was she thinking about; Elaine wouldn't do that would she? After the humiliation of what I had just done? My cock let me down at this point, getting hard again just imagining what a weekend with Tammy would be like, very fun I thought.


(Since this is getting too long I will leave you with those thoughts in mind and continue the training in the next chapter.)

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