Sissy Boy Secretary Ch. 05

The whole week was spent on completing the paperwork needed for our customers. There was a lot of work and I had worked through quite a few lunch breaks, but completed the work on time. Business was getting better each week and Elaine had said that I was one of the reasons that it was going so well. Although I still stripped to my panties while in Elaine's office, nothing really happened except to get work done. Therefore, it came to a big surprise for me when a young woman showed up in front of my desk asking if this was Elaine's office.

"Yes this is Elaine's office, how can I help you?" I found it hard to keep my eyes from wandering to the cleavage this young woman showed in her low cut summer dress. It was obvious that there was no bra holding her 34D chest in place.

"I'm here to apply for the secretary's position," Lisa said.

"What secretary's position is that?"

"Sue told me that Elaine was looking for another secretary. I have an appointment this morning."

I asked her to take a seat while I called Elaine. I watched as her hem moved up very far on her lovely thighs. Picking up the phone, "Elaine there is a young woman here that says she has an appointment with you this morning."

"Oh, please send her in," Elaine answered, not giving me any explanation at all.

Turning to Lisa, "Elaine will see you now, please go right in."

Watching her ass swaying so invitingly, as this beautiful creature made her way into Elaine's office, I went back to daydreaming.

"Thank-you sissy boy," she mumbled as she passed.

"What?" not sure I heard her right.

"Thank-you," Lisa said this time, smiling as she did.

I sat there going over in my head just what I could have done wrong that Elaine was going to hire a new secretary. The reports were all complete, I filed everything that needed to be, and I could not find a single thing that I may have forgotten.

About twenty minutes passed when Elaine called for me to come into the office. Entering the office, I removed every thing except my panties, a pink lace pair today. I felt lucky that Lisa was sitting in a chair facing away from me. Elaine had gotten up to stand next to Lisa, keeping her attention away from me. Elaine's hand was resting on Lisa's shoulder as I heard her saying, "Now to show you one of the perks of working here."

Lisa's eyes bulged out when Elaine motioned for me to crawl in front of her. Elaine now had her hand over one of Lisa's tits, gently pinching her nipple.

"This is our, (apparently I was to be secretary to both), sissy boy."

Unable to hide my excitement I knelt in front of this young woman with my cock hard as a rock, pushing my panties out. Elaine continued to play with her nipple, "Would you like to try out our sissy boy?"

"Just exactly what is sissy boy's talent?" Lisa asked while moaning slightly under Elaine's hand.

"Oh, sissy boy has a very talented tongue as you will soon see. Stand up for me and you will find out." Lisa stood in front of Elaine as she removed the fabric covering her tits, her nipples pointing out. "How does she look sissy boy? Would you like to please her?"

"I would love to make her happy for you Elaine." I remained on my knees watching as Elaine unbuttoned Lisa's dress, letting the top part fall off to her waist.

Elaine's hands were caressing Lisa's tits when she said, "Now take her dress off sissy slut."

Still on my knees, I reached out to push the dress down her long sexy legs. Lisa stepped out of the dress, standing there in just her panties, garter belt, and stockings. Elaine was behind her, arms wrapped around, aggressively caressing her nipples. Judging by the increasing wetness of Lisa's panties, she was enjoying standing in between Elaine and I.

"Clean those panties sissy boy; we do not want them stained." Elaine ordered as she pressed against Lisa's ass, pushing her towards my face.

Reaching up to grab Lisa's hips, edging even closer to her pussy, I was stopped when Elaine said, "No hands sissy boy, just your tongue."

Putting my hands behind my back, I leaned forward to lick Lisa's panties. I was not surprised to find that they were already quite wet. Licking up and down the pussy, trying to get my tongue in through the panties, I devoured her sweetness. I could not see that Elaine had pulled Lisa's head back to give her a tongue filled kiss, but I heard the moans. This made me lick faster and deeper. I moved the panties aside with my tongue and continued to lick this pussy like there was no tomorrow. Lisa was pushing her pussy hard into my face as I continued assaulting her engorged clit. My lips surrounded her clit, gently nibbling the hard knob. Continuing to devour her juices, which were flowing freely by this time, my tongue went from the bottom of her pussy, then right back up to the clit. Lisa squirmed as the first orgasm hit her hard. I licked as quickly as I could but still ended up with a face covered in juices. As Lisa's orgasm subsided, Elaine had her sit down again.

"Well how do you like the perks Lisa?" Elaine asked as she moved over to me.

Elaine leaned over to kiss and lick Lisa's juices from my face as Lisa said, "Oh my, that was great!"

"What do you think sissy boy, should I hire her?" as she turned to grab Lisa's nipple with her teeth, her other hand busy fingering her wet pussy.

"I would enjoy working with her very much," I replied before thinking.

"Oh, so you think I should hire her?" Elaine said disappointedly. "Who said you would both be working here sissy boy? You should know better by now! Making assumptions always gets us in trouble. Get the crop from the filing cabinet. You need another lesson."

I crawled over to the filing cabinet while Elaine explained to Lisa, "Sissy boy knows better than that. I make all of the decisions around here. I put up with these little mistakes only because sissy boy's tongue is so good, as you now know."

While crawling back I could see that Elaine was continuing to caress Lisa's hot body. "Now you will see what happens when sissy boy misbehaves." She leaned over to get the crop from my mouth. "Bend over the desk sissy boy."

I could not believe how hot I was bending over the desk in my pink panties in front of a woman that was half my age. I steadied myself for the punishment that was to come. Swish...smack came the first blow.

"That is one, thank you Elaine." Swish...smack, "That is two, thank you Elaine."

This continued until the count of ten. My ass was on fire.

Elaine handed the crop to Lisa, "Your turn now young lady." Elaine's hands were all over Lisa as the first blow hit me. Swish..smack.

"That's eleven, thank you Lisa."

"Excuse me! Eleven? I believe that was only one sissy boy!"

"I'm sorry ma'am. That was one, thank you Lisa."

Swish…smack, "That was two, thank you Lisa."

Swish…smack, "That was three, thank you Lisa."

Lisa continued until the count of ten, then she rubbed the crop up and down the crack of my ass. I heard a giggle coming from Elaine; she obviously likes this added touch. My ass was on fire but my cock was rock hard, pressing tightly against the lace fabric of the panties. Both set of eyes went straight to my raging hard on as Elaine had me stand and turn around. I stood there with the panties sticking straight out, pointing at the ladies.

"You see Lisa; you only have to know how they like to really be treated. Do you see how excited sissy boy gets?" Rubbing her hand gently up my thigh, causing my cock to twitch with excitement, Elaine groped my cock. Seeing this Lisa used the crop to caress my cock.

With one hand grabbing a handful of Lisa's hair, Elaine leaned over to give her an open mouth kiss, tongues intertwining. Elaine's other hand was busy with Lisa's tits, squeezing and twisting her hard nipples. As the kiss broke, "Of course there will be clean up duties for you too Lisa."

Elaine stood up to do a slow seductive strip tease. Elaine unbuttoned the blouse one slow button at a time. Pulling the blouse out of the dress hem, she let it fall to the floor. Elaine's nipples were topping off her tits predominately, of which one found its way to Lisa's mouth. Lisa tongued and sucked the hard nipple until it was red, and Elaine was moaning uncontrollably.

Elaine stepped back, pulling Lisa to her feet as she did so. The two of them embraced in a groping hug, hands exploring each other's body.

Releasing Lisa, "Please finish undressing me Lisa."

Lisa reached out to unzip the dress with the zipper on its side. Caressingly she pulled the zipper down, releasing the hold the hips had on it. The dress fell ever so slowly down over Elaine's smooth thighs. Elaine stepped forward out of the dress, her pussy right in Lisa's face. Lisa's hands were moving up Elaine's thighs as her tongue reached the wet panties. Moaning as she licked the outside of the panties, right over the clit, Lisa used her teeth to pull the panties down. Elaine stepped out of the panties, leaving her feet shoulder length apart. Lisa lovingly licked her way up Elaine's smooth legs to the wet shaved pussy that waited.

Elaine leaned over hugging me while moaning and whispering in my ear, "Damn is this little slut good! She must have …oohhhh….done…ooohhhhh….this before!" Elaine's hips were pressing forward, pushing her pussy into Lisa's ever active tongue. Elaine's moans got louder as Lisa used two fingers to fuck Elaine's pussy as she attacked her erect clit. Elaine had my head pulled back and her tongue was exploring my mouth deeply. Elaine's orgasm struck like a bolt of lightening. Grabbing the back of Lisa's head, pulling her mouth tightly against her clit, Elaine let out a scream that would make Tarzan blush. As Elaine's orgasm subsided, she released her grip on Lisa. Lisa moved up to kiss Elaine, giving her a taste of her pussy juice that covered her face. Lisa then leaned over to give me a tongue filled kiss too, which Elaine quickly joined.

Breaking away from the kiss Elaine said, "Well I am happy with your performance, how would you like the job Lisa?"

"Oh I would just love working here!" Lisa responded immediately.

"Ok then we will go over the details later, for now we should think about getting some lunch. Lisa gets dressed and we will all go to my house to eat."

Lisa and Elaine both got dressed, leaving me in only my panties. While they were dressing, Elaine told me to put the riding crop back where it belonged. I could feel their eyes watching as I crawled over to put it back, my red ass in the air. Once back Elaine handed me her suit jacket, "Put this on Sissy Boy."

Dressed that way we left the office for Elaine's car. Luckily, only the other secretaries saw me dressed like that. They had a good laugh as we passed by, Elaine slowing down on purpose.

The next part will start with the walk out and ride to Elaine's.