Sissy Boy Secretary Ch. 04

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to my desk and began going over the next couple of contracts that had to be completed, hoping that my hard-on was not to visible.

Elaine arrived looking elegant as usual in a smart business suit complete with short skirt, blouse, and jacket. She stopped in front of my desk, "Good morning Sissy Boy," a little too loud for my liking. I heard giggles in the background from the three other secretaries there.

"Good morning Elaine."

"Give me a few minutes to settle in and then come into my office."

"Yes ma'am," I returned not knowing what to expect. I waited for about ten minutes then went into Elaine's office, removing all my clothes except my new panties.

"I got a call telling me that you returned to the store last night. I see that you have one of the new pairs on now. Please model them for me."

"Yes I did, I did not want to disappoint you so I went back to get the panties that we went there for in the first place," as I turned around slowly, letting Elaine inspect the panties.

"Very nice choice indeed, you look so feminine in them."

"Thank-you ma'am, I so happy you approve."

"I am a little angry that you went back to the store alone though. Why didn't you call me so I could go along with you?"

"I did not want to upset you ma'am. I thought I had wasted enough of your valuable time."

"Well you should have called knowing that I could say no. Please get the crop, you must pay for you indiscretion."

Getting down on my hands and knees I made my way over to the filing cabinet. I could feel Elaine's eyes watching me as I went. Immediately my cock began to get hard, not sure if it was her watching me or the impending spanking that excited me more. Placing the crop in my mouth, I crawled back over to Elaine.

This time instead of having me lie over her lap, she told me to stand and bend over the desk. From this position, her 5" spiked heel shoes could be seen by me as she walked around, draping her hand all over my exposed ass. This was having quite the effect on my cock, as harder and harder it got as the anticipation built. Just as her fingers were caressing my balls from behind.....Swish. Smack!

"Ouch! That's one ma'am, thank-you very much."

Swish...smack! Swish...smack! Swish...smack! The assault continued until the count of twenty.

"That's twenty ma'am, thank-you very much." My ass was burning by this point, but my cock was raging, a point Elaine did not miss.

"You love being punished don't you Sissy Boy? It is quite exciting for me too you know?" These questions did not require an answer. The smell of her sex was clearly in the air. Remaining in my bent over position, Elaine gently rubbed and patted my ass while she spoke, running the crop in between my legs and over my hard-on. Elaine then walked away, the door opening and closing as she went. Since I was not sure that she was gone, I remained bent over, trying, but not succeeding to look around the room. In the position that I was left in very little of the room was in view. Time seemed to stand still until finally the door opened again. The people that entered were talking until they saw me, then a giggle escaped them. Not sure just how many people, or who entered with Elaine, I became nervous.

"Oh you were right Elaine; Sissy Boy does indeed have a very cute ass."

"His ass is so red, what did Sissy Boy do to deserve that?"

"Sissy Boy decided to go shopping without me, and from what I heard he had a very good time."

Having determined that there was at least two other women with Elaine, I felt very venerable standing as I was. I thought I recognized the voices as a couple of the other secretaries that worked there. The whispering and giggling continued for a few minutes while the women discussed what they were going to do. The humiliation and anticipation only added to my excitement. The lace material of the panties felt great against my raging hard-on. I was wiggling a bit causing a little friction against it. The ladies did not miss this maneuver.

"Look at Sissy Boy wiggling around. He looks so cute in those panties bent over like that," said one of the secretaries. She was standing next to me, her hand placed on my wiggling ass.

I was not sure whom it was, but her hand felt so soothing on my red ass, until...Smack! Her hand came down hard, spanking my ass. Her hand continued to rub my ass and in between my legs, grazing my hard-on. I was never so excited, bent over in front of at least three females, ass red and exposed while they chatted about just what they were going to do. The more she caressed my ass the more excited I became.

Elaine then came in front of me, lifting one of my hands and sitting on the desk before replacing it back on the desk beside her. Her skirt was above her waist, the wet panties just stared at me, smelling delicious. It appeared that Elaine was just as excited as I was.

"Sissy Boy I believe that my panties have become soiled. Why don't you be a good little sissy boy and clean them for me."

Reaching my tongue out to lick the lace panties, tasting the results of her excitement, I licked and sucked her panties like a man obsessed. As I was cleaning Elaine's panties a stocking covered leg ran up against my thigh, gently rubbing it up and down. A couple of hands were also rubbing my ass all over. I was in heaven.

"Oh, Sissy Boy certainly looks like he is doing a great job Elaine. Do you mind if I take a turn once he is done with you? My panties seem to have gotten soiled also."

"I wouldn't mind a turn either. Sissy Boy certainly looks like he knows what it takes to satisfy a horny women, and by the feel of this," her hand was grabbing my hard-on,"he certainly enjoys it too."

She continued to rub and grab the hard-on while the other hands continued to caressing my ass. Concentrating on the panties in front of me, I was trying my best not to cum, as hard as that was. I found Elaine's clit and was now gently nibbling on it as I heard a moan escape her lips. A smile crossed my face, as I wanted to do the best job I could at pleasing my boss, especially in front of her friends. Elaine let out a loud moan, grabbing my head and forcing it into her pussy as she had a big orgasm. Lapping up the juices as quick as I could, oh's and ah's could be heard from her friends. They enjoyed seeing and hearing the pleasure as Elaine let her orgasm roar, grinding her pussy into my face.

Elaine moved away on wobbly legs, allowing another one of the secretaries to take her place. Tonguing around my face to get as much of Elaine's juice into my mouth, and believe me there was a lot to get, as she had covered my face. The next lady to take Elaine's place was Sue, a leggy blonde-haired lady with a body that gives a man a hard-on from across the room. Standing in front of me and slowly raising the hem of her dress, showing off tan lines from a very skimpy bikini that she must wear, I was amazed to see a shaved pussy that was dripping already. When her dress was above her stocking thighs and waist, she leaned back against the desk, grabbing my head with both hands, guiding me into her pussy. My tongue leaps out to taste one of the sweetest pussies I had ever tasted. Going from bottom to top a few times, savoring the taste and smell, I stopped to drive my tongue hard against her clit. A moan escaped her lips as I bit down lightly on the obviously very excited clit. It was not long before her juices were flowing freely and a constant moan was heard, not only from her but also from me. Sue held my head tightly against her juicy pussy. When she finally gave up the pressure on my head, I continued to lick and clean her pussy along with getting the juices that flowed down her thighs.

"Holy shit is he ever good! That was the best pussy licking I have ever received." Sue then grabbed my head, pulling it up to her lips and giving me a kiss that showed her appreciation. I was beaming inside knowing that this would please my boss. Our tongues intertwined inside her mouth as the kiss continued. Moving out of the way I heard, rather than seen, Sue kissing Elaine thanking her for sharing me with her.

"You were not kidding when you said Sissy Boy eats your pussy better than anyone before. I always thought that you did a good job Elaine, but sorry to say Sissy Boy is even better than you."

Apparently, these ladies swung both ways, which came as no surprise to me. I had often seen these three ladies leaving the office together, for lunch or on their way home.

It was now Linda's turn, a lady whose ass I had often watched wiggling its way across the office. Her reddish hair shined in the fluorescent lights of the office, hanging halfway down her back.

"Over here Sissy Boy, it is my turn now," she said from the couch across the room.

I turned to look at Linda sitting on the couch, one leg on the back, the other on the floor. Sitting the way she was, naked except for the garter belt and stockings caused my hard-on to stir. Her 34D tits standing up proud on her chest, firm, with nipples hard. Getting on all fours and crawling up in between those luscious thighs, I began my duties. Starting at the knee, I licked my way to the dripping wet pussy that waited. Spreading her lips with my fingers, I started to lap away at her pussy, slowly at first but gaining speed fast. I was driving my tongue in as deep as I could. I put a finger in her pussy while my tongue assaulted her erect clit. Biting it gently, causing her to let out a moan. Pushing my finger in and out of her wet pussy, I continued to lick and nibble her clit until her hands were driving my face hard into her as she approached an explosive orgasm. After she was done, I continued to lick her until she was clean.

"Oh my God! That was fabulous! Damn we need to keep Sissy Boy around, I could have him do that a couple times a day!"

"Oh I intend to, not only is Sissy Boy good at that he has become quite the good secretary too."

Not being sure what was going to happen next, I sat back on my heels and licked as much cum off my face as my tongue could reach. Looking around the room at these sexy ladies assured that my hard-on was not going away.

"I do believe that Sissy Boy deserves a reward now after all his good work."

"I think so too, sit up here Sissy Boy," Linda said as she patted the couch next to her.

While I was working on Linda, the other two had used the time to remove the rest of their clothes also. Now sitting on the couch next to Linda, with her twisting and teasing my nipples, I watched Elaine and Sue making their way over to us. My cock was working overtime with these three sexy ladies surrounding me. Elaine and Sue each grabbed a knee and spread them apart, at the same time Linda had bent over to kiss and bite my nipples. Elaine reached down and tore the panties off me, not gently either, the thong part digging into my ass before they finally ripped free. All the ladies had a good laugh as I let out a small scream. The pain quickly replaced with extreme pleasure as Sue started to lick and suck my balls. Elaine bent over to take the head of my cock into her mouth, her tongue going around the head as she did. Taking my cock out of her mouth, Elaine and Sue were trying to kiss with my cock in between their lips. They were both running their tongues up and down my hardness, exploring every inch. Soon they were taking turns giving me a deep-throated blowjob, first one, then the other. Both of them also had a hand on my balls, caressing them, squeezing, and pulling on them. Not to be outdone Linda made her way down my chest, stopping to twirl her tongue in my belly button, to take her turn sucking on my cock. It seemed to be a contest for the ladies, seeing which one could make me explode first. I was enjoying every minute of this, trying my hardest to make it last. Feeling me tense up the ladies let up and one of them started to jerk me off, waiting for the explosion, which came quickly. My cum shot into the air, landing all over the ladies faces. I am not sure who it was as my head was bent back on the couch and my eyes were half closed, but one of them sucked the last few drops from my cock. When I finally looked up all three ladies were licking the cum off each other and kissing. When they were finished cleaning each other off, they each gave me a kiss, tasting of my cum. I sat back and relaxed as the ladies sat down on each side of me, and Elaine sat right in my lap.

"Whew, that was fun," Elaine said and the other two agreed.

"Thank you so much for sharing Sissy Boy with us Elaine, I believe we owe you one," Sue said.

"Believe me that was only the start ladies, we will definitely do these a lot more."

I smiled knowing that I had definitely pleased Elaine and her friends. Even after that, my cock started to get hard again. Elaine noticed this and wiggled a little more in my lap.

"Unfortunately we have to get some work done today." Elaine got up and turned to me, "Now time to get our clothes, and get us ready for work Sissy Boy."

I crawled over to retrieve the clothes and soon was dressing each of the ladies. Standing naked relishing the job at hand, my cock returned to its hardened state. When I tried to replace the panties on Linda, she stopped me.

"I think you should wear these Sissy Boy, since yours have been ruined."

I put the soaking wet pink lace panties on over my hard-on, much to the amusement of the ladies.

"Now get the door for the ladies and let them go back to work."

I went to the door, nervous about standing there in only Sue's pink panties while the ladies kissed and said good-bye and made lunch plans. Both ladies went past me, making sure to give my hard-on a little feel as they went by. Once out the door both ladies stopped, turned and said, "Oh how rude of us, come here Sissy Boy." I am sure my face turned as red as my ass was right now. I took the couple steps out of the office to the ladies, nervous that I might be seen. They both gave me a kiss and thanked me for a good meeting, taking their time doing it, only adding to my nervousness. I quickly went back into Elaine's office, looking around to see if any one had caught me before closing the door.

"Now that was fun, I just wish we had more time. It is time to get some work done. Return to your desk and start on your assignments now Sissy Boy. Oh, by the way, I want to thank-you for not embarrassing me in front of my friends. I think we will have a lot more fun times with them."

"Your welcome ma'am, I am glad I could please you."

I then dressed and returned to my desk to start the days work. My mind did although wonder just what more fun we would have in the future.

To be continued...

I hope you are enjoying the stories so far. Comments and suggestions are always appreciated.