Sissy Boy Secretary Ch. 02

I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked like she was giving it an extra special sway, knowing she would watched.

"Good morning sissy boy," was all she said before entering her office. Immediately the cock between my legs began to rise, being called that aloud in the outer office turned me on. Looking around, hoping no one had heard her call me that.

"Good morning Boss," I replied as she was shutting her door. Trying to concentrate on my work for the next few minutes, as hard as that was, I was wondering what was in store for me today. The panties felt good rubbing against my now raging hard-on. Seeing her hot ass sway through the door had me quite excited.

"Sissy boy, come in here now!" the intercom sang.

Nervously I grabbed my notebook, pen, and the finished Scottsdale account paperwork, then went into her office.

"Yes Bo..." as I tried to say, but was cut off before the words left my mouth.

"Show me now," was all she said when she interrupted me. I stood there dumb founded for a minute, not sure, what she meant. "Show me the panties sissy boy and be quick about it! I will not ask twice!" she said in a commanding tone.

As quickly as I could I removed all my clothes, except the panties, but it was not quick enough.

"Well aren't we slow this morning! From now on, you had better be dressed properly when you are in this office! On your hands and knees and get the riding crop. Do it right now!"

The look in her eyes told me that she was enjoying my discomfort. As I crawled over to the filing cabinet, stealing looks at her crossed legs as I went, I could feel her eyes on me. Her legs looked great, with one crossed over the other, bouncing slightly. This made the skirt ride higher up on her thighs, showing off her sexy thighs. The top few buttons of her blouse were also undone, leaving the top of her healthy breasts on display. Her hard nipples pressed against the thin fabric, reminding me that she enjoyed this too. After I got the riding crop, I crawled back over to give it to her. The scent of her driving me wild, the closer I was to her.

"Stand up and bend over the desk! You must be taught a lesson!" My ass was totally exposed to her in this position.

Swish. smack! Without warning the first blow struck. "OUCH!" I responded without a chance to think.

Swish...smack...swish...smack. The next two strikes hit. "Did you forget how to respond?" Swish. smack.

"OUCH, I'm sorry, 3 maim, thank-you maim!" but this was too late.

"I don't believe we start counting at 3 do we?" obviously enjoying her control over me. Swish. Smack.

"OUCH, that's 1 maim, thank-you very much maim," my ass already getting hot.

"That's better," as she rubbed the riding crop on my burning ass. Up and down the crack a couple of times as she did. Then without warning, swish. Smack.

Better prepared now, "That's 2 maim, thank-you very much maim," I responded.

She continued to smack my ass and alternately just rub it until the count of 10.

"That's 10 maim, thank-you very much maim." Now I could feel my ass really burning, something I thought I would have to get used to.

Leaving me bent over she pushed her chair back and stood behind me. While rubbing her hands over the red, sore ass and then in between them to caress the now raging hard-on, "OH this color looks good." Not sure if she was talking about the red of the ass or the color of my pink panties until she said, "But I do think we will have to get you a few more pairs." She continued to caress the ass as she spoke, which felt so good.

"Now stand up and lie down, I don't think these panties will last with you straining the front of them like that."

Moving over and straddling my head with her knees, her wet pussy just inches above my face; she reached down to stroke my hard-on through the fabric of the panties. Moving the panties to one side, she began to move her hand up and down the hard cock slowly. She reached back to raise her skirt up and over her hips. Slowly she moved her pussy down to meet the waiting lips. Immediately my tongue was licking her pussy from the bottom to the top, paying close attention to her erect clit, nibbling it softly. She leaned over to stroke and lick my cock, bottom to top, running her tongue all around the head. It only took about 10 minutes before I erupted into her mouth, both of us moaning so loud I was sure everyone in the building could hear us. Once done she licked my now deflating cock clean and placed it back into the panties.

Standing up and re-doing her skirt, "Much better, now they will last longer."

As I stood up she planted gave me a very passionate kiss, our tongues intertwining. Breaking away, she handed me the crop, "Put this away, I don't think we will need it for a while."

She returned to her seat and began reading the Scottsdale report, ever so often sneaking a look at my ass as I crawled back to put the crop away. I retuned to the side of her desk awaiting instructions.

After a few minutes she looked up, "This is great work! I am sure the company will go for this. As a reward we are going to take the afternoon off to go shopping."

Not sure how shopping was going to be a reward for me, since I hate to shop. Little did I know just how much fun this adventure was going to be.

"OK that will be all for now. There is other work to do now before we go and I need to get it done."

I put my clothes back on and returned to my desk, sitting gingerly on my ass. I diligently worked on the next 2 hours, with the shopping trip on my mind. It seemed like forever but 11:30, lunchtime, finally came.

Elaine came out of the office, suit jacket on and blouse buttoned back up, "Ready to go? Lunch will be my treat Sissy boy."

Without waiting for my response, she started for the elevator, giving me a great view of her hot ass. Quickly getting up I followed her.

Arriving at the restaurant, after a short drive, with her at the wheel, I watched the skirt ride up as she exited the car. Walking in front of me, she stopped at the door, waiting for me to open it.

"Thank-you Sissy boy," she said in the middle of the waiting lunch crowd. For the rest of lunch she continued to refer to me as Sissy boy, regardless of who heard. Her foot found the way to my crotch several times during the meal, caressing it gently.

The rest of the meal went events, unless you consider her calling me Sissy boy in front of everyone eventful. Elaine paid for the lunch on our way out, and to the car, we went, with me following her like a puppy dog in heat. Soon we were on the way to go shopping.

After a short drive, we arrived at what looked to be a warehouse with a single door. The only sign anywhere was on the door, which said, "You must be 21 to enter." This part of town I had not been in before. Entering I see that both walls are filled with all sorts of sex toys. Further on are isles of magazines and movies. Going to the back of the store, I see all sorts of lingerie outfits. The back wall has a few doors side by side, the dressing rooms I assume. Elaine started looking through the outfits, ignoring me for the time being. Taking the time to look around I notice about 10 other women in the store. I over hear a sales woman telling a customer that indeed this outfit is easy to remove when you dance. It seems that the local strippers use this store.

Elaine chose three outfits for a French Maids outfit, a schoolgirl outfit, a hooker's uniform, for me to try on. She hands them to me then points at an open changing room. I grab the outfits and enter the room. Putting on the French Maids outfit first, I open the door and try to stay inside as Elaine and the sales woman talk. I motion Elaine to come look at how the outfit looks.

"Sissy boy, how do you think we can see it with you in there?" Elaine says loud enough for everyone in the store to hear,"Come out here so we can get a good look!"

"Don't be so shy sissy boy! Turn around so we can see it all!" I do as requested and model the outfit for them. They reach up and run their hands over the outfit saying how cute it looks on me.

"Now bend over so we can find out if it's short enough."

Bending over so my pink ass is fully in view of everyone, I hear giggles from a couples shoppers near-by.

"That does look cute and short enough. It looks like your Sissy Boy has been bad already today."

"Yes Sissy Boy needed to be taught a lesson this morning, but Sissy Boy has been good since then," Elaine was telling the sales lady while she rubbed my ass, swatting it a couple of times. "Now stand up and walk around a bit Sissy Boy, I want to see how it looks."

Walking back and forth in front of the dressing rooms, showing off the outfit for Elaine, I could feel my face turning quite red. A few of the other women made comments, enjoying the obvious embarrassment that showed. One of the women even let out a wolf whistle as I walked.

Elaine walked over and whispered in my ear as she rubbed my hard-on, "I see that you are enjoying this Sissy Boy. I will take care of this when we are through."

This continued while I modeled the other two outfits also. The only difference was that all the women had gathered around to enjoy the show. Elaine paid for all the outfits when I was getting dressed. When exiting the dressing room, applause greeted me from all the women.

"Hurry up Sissy Boy," Elaine yelled from the front of the store, "I haven't got all day."

Elaine handed the schoolgirl outfit to me when I reached her.

"Put this on Sissy Boy. Do not bother going to the dressing room, get dressed here. Everyone has seen you any way."

Removing my clothes and putting on the outfit, I handed Elaine my clothes. She put the clothes in the bag with the other outfits, and then headed for the car. Forced to follow her to the awaiting car dressed in the schoolgirl outfit, right behind her I followed. Elaine was putting the bag in the trunk so there I was, waiting by the door. She fumbled with the lock for a minute before the trunk opened. Finally, she entered the car, leaning over to unlock the door, which I quickly opened and got in.

The ride back to our work was brief, Elaine smiling the whole time. Only a couple truck drivers honked their horns as we passed them, obviously liking my outfit. Elaine parked the car and got out. I did the same, going over to her side of the car, which she was leaning on. Pulling up her skirt, as well as mine, she pulled my hard-on out, slipping it into her moist pussy. It did not take long before both of us reached an orgasm. Elaine then kissed me, said that she would see me in the morning, as she got in her car. Leaving me there in the schoolgirl outfit to walk to my car and go home.

On my way home I was wondering what was going to happen tomorrow, a smile crossed my face.

To be continued...