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Sissy Boy Secretary

By: Hotenuf4u



As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a 5'10" fox of a lady, found out about my indiscretion when she checked out the sites I was viewing on the internet. About 6 months after I took the job she asked me to stay after work to discuss a problem she found. I wasn't sure what this problem was so during the rest of the day I checked and re-checked my past work, without finding any problems. Seeing everyone leaving for the day I was getting more nervous.

I timidity knocked at her door and after a couple seconds she asked me to enter. She sat at her desk in her big office chair just staring at me for a minute. Then she asked me to take a seat next to her desk.

"I was checking over the access to the internet from your computer and I found some disturbing things," she told me with a stern look on her face. 

I should explain that I had been searching sites about dominant females & how they controlled their men, something I find very exciting. The humiliation factor I found to be very dangerous and sexy, it turned me on quite a bit. I often found that I had a hard-on just from reading and viewing the material.

Turning her computer screen so I could see it too she asked, "Is this what I pay you to do while you work for me?" The picture showed a male secretary in panties at his bosses feet with her holding a riding crop. My penis immediately got hard, something I couldn't control.

"Is this how you think of me? A controlling boss?" she asks. When I didn't answer right away she asked again, "Well??? Is it?," her voice becoming more stern.

"No mam it is not how I think of you." I replied.

"Well is this how you'd like me to be then?" she asks.

"Well it would turn me on. You are so beautiful and command this type of respect mam." I come back with. Watching as she crosses her legs which causes her skirt to move up farther on her thigh.

"Stand up," she orders me to do. My hardness could not be hidden, a fact she noticed right away.

"I see that this turns you on very much by the looks of you crotch." She says while staring at my hard-on.

"You are a very beautiful lady with a great body which is the main reason I took this job mam." I say. "The way you commanded my respect from the interview has always excited me. You are always in control of any situation which I find so sexy."

Let me tell you a little about Elaine before I go on. You see she is a 5'10" blonde with hair down to the hottest ass I've ever seen. Her 34D chest stands firm without the help of a bra, the nipples standing out on quite a few occasions. She always wears skirts that come a couple inches above her knees, showing a little thigh but still very professional. Her blouses are always covered up with a suit jacket that she removes only when alone in the office. At 34 she has kept her body in very good shape. 

"So what do you think we should do about your surfing the net on company time? I should just fire you since you do know its against the rules." Elaine asks.

"Could you just give me a warning and I'll never do it again, I promise. I'm sorry that I've broken the rules and know I was wrong." I counter.

"I'm not sure that you would learn a lesson that way though. I think more must be done." She replies.

"I will do anything that you want but I really want to keep this job." I say.

"Anything you say? Do you mean that?" she asks.

"Yes anything, I love this job!" I answer.

She sits and thinks for a minute leaving me to suffer. "Well I think we can work something out and you might even enjoy it." She says. "First off I believe you deserve to be punished for your indiscretion. A spanking might teach you not to do it again, don't you agree?"

I quickly say, "Yes I think I do deserve it. I was wrong in searching the internet during work hours."

"Take off your clothes so I can do it properly!" she demands sternly.

I remove my clothes as fast as I can. I stand there with my raging hard-on naked for her to see.

"I knew you would enjoy this. Now get down on all fours and get my riding crop from the filing cabinet." She says.

I crawl naked to the filing cabinet knowing her eyes are on me as I do it. I open the filing cabinet drawer and place the crop in my mouth and make my way back over to her feet. She takes the crop from my mouth and tells me to place my chair in the middle of the room, staying on my hands and knees. After a couple minutes of struggling I get the chair where requested. She removes her jacket to reveal that her nipples were quite hard. She was enjoying this too it seems. She sits down in the chair and looks at me on all fours in front of her.

When she is comfortable she tells, "Get over my knee now!!!" which I do immediately, my hard-on scrapping her thighs. She starts to caress my ass very gently then without warning I hear the swish of the crop right before I feel the sting.

"Ouch!!!" I respond as it hits.

"I don't believe that is the response I want sissy!! Shouldn't you be counting and thanking me for allowing you to keep your job?" she asks.

"Yes mam, I'm sorry. That's 1 & thank-you for it mam." I say.

"Just how many do you think it will take for you to learn your lesson?" I was asked.

Not wanting to say an actual number I reply, "As many as you think I deserve mam."

"That's a good answer my sissy. I believe 20 should be a good start." She responds.

Smack!!! Goes the 2nd hit, "2 & thank-you mam," I say.

This continues until all 20 hits are finished with her calling me sissy the whole time, which only adds to my excitement. She is so much in control of me at this point and she knows it. She rubs my very red ass at this point, "Gee that looks so red and it looks like it hurt. Do you think you learned you learned your lesson my sissy boy?"

"Yes mam, I will never surf the internet again on work time!" I respond.

"Good, now to continue your punishment," she says.

I thought my punishment was complete but she had other ideas. She has me stand in front of her while she teases my cock with the riding crop. "You did seem to enjoy that as much as I did, didn't you?"

My cock throbbing now as she teased it, "It was what I deserved mam."

"Now since you are going to be my sissy I think you should dress like one. A nice pair of panties would be a good start. Get on your knees!!!" she orders.

Having no idea what she was thinking I sank to my knees in front of her. She slowly moved her thighs apart revealing a frilly lace pair of thong panties. They looked to be a wet spot in the center of them.

Standing up she tells me, "Remove my panties sissy boy!" A nickname that thrilled me, especially coming from such a dominant women.

I reach up under her skirt and grab the top of the panties to pull them down her sexy legs. As I thought the panties were indeed quite wet.

Stepping out of them she commands, "Now put them on sissy boy!" I pull the panties on over my hard-on, the lace pushed out in front.

"Turn around and let me see how they look on you sissy boy!!" I do just that and she comments, "Now you look like the sissy boy you are! Your red ass matches the color of the panties sissy boy."

"As you can tell this has got me quite excited too. Now what do you think we can do about that sissy boy?" she asks. My hard-on feeling the wetness of her panties. She moves around me letting her hands roam over my body, slapping my ass a couple of times as she does. "Would you like to see how excited sissy boy?"

Of course I said, "I would like to very much!!!"

"Would you like to please me my little pet?" she asks as she caresses my red ass. Slowly she starts to unbutton her blouse, revealing 2 very obviously hard nipples. "Would you like to suck my nipples sissy boy? I think that would feel good to me."

I practically drool as I respond, "I would love too mam!!! Any thing to please you my boss."

"OK then you may suck on them but do not use your hands!!!" she says. I begin with the left sticking my tongue out to gently lick it before putting it all in my mouth. Then I move to the other repeating the same process as she leans her head back and moans. "That feels so good. I guess being a sissy boy you do know how to satisfy a lady."

After a few minutes of this, switching back and forth between nipples, she pushes my head away. "Now sissy boy I have another task for you. It seems I've become very wet and I don't want to stain this skirt. You may now remove it but again, no hands." She commands. I get down on my knees and use my mouth to pull the zipper down. Watching me fumble with the zipper makes her giggle a little, "Good sissy boy."

Her skirt finally falls to the floor. She steps out of it and moves back a little, her hand going to her pussy. "Would you like to lick it sissy boy?" She moves away to sit at her chair.

"OH YES!!! I would love to lick it boss!" I say from my knees.

"OK then crawl over here between my legs and beg for it sissy boy!" she says. I think she enjoys watching me crawling on the floor over to her as I watch her play with herself.

I ask, "May I please lick your pussy boss and give you all the pleasure that you deserve?"

As she holds her lips apart, "You may lick me now but no hands sissy boy and you had better do a good job!" I reach out with my tongue licking her from the bottom to the top of her pussy. I pay special attention to her clit as she moans with pleasure, using her hands on the back of my head to pull me in more, securing my head in place. My head is held in place tight as she experiences an explosive orgasm, covering my face in her juices.

"Now clean up the mess sissy boy!!" she demands. I lick every inch of her thighs and pussy until she is completely clean. "Get my clothes now!!"

I do as ordered on my hands and knees of course. I watch her get dressed from my knees. She then grabs my clothes going to her door. "That will be all for today sissy boy!" throwing my clothes out to my desk. "Now crawl out of here and get dressed. Tomorrow I expect your panties to be clean and that you will be wearing them!"

I crawl out of the office hoping that the night guard is not making his rounds. She stands in the doorway laughing and saying, "That's my sissy boy, I have more plans for you tomorrow. Good night!"

I get dressed thinking about what will be in store for me now. I have never been this excited in my life and hope this is only the beginning.

To be continued...

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... 



Sissy Boy Secretary Ch. 03



Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! 

After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door. 

The salesladies smiled and said, "Look Sissy Boy has returned!" This caused me to blush and become hard again.

"We forgot to get some more panties, which is why we came in the first place."

"Follow me Sissy Boy, I think we know your size already," as she led me back to the clothing racks, swinging her ass as we went. (A fine ass it was I might say.)

Picking out a couple of pairs of panties, "These should look good on you."

I reached to take the panties to go to the dressing room to try them on, but she pulled them away, "Where do you think you are going Sissy Boy? You are not getting shy on me now are you?"

Apparently she intended me to try them on right there, "No ma'am, but you have other customers here." 

"Lets make a deal Sissy Boy, you try them on here, and I will give them to you free of charge."

How could I argue with that? "OK that sounds good to me." My clothes came off and she handed me the panties, which I quickly put on hoping not to show my excitement. Ya, like that worked. She held the panties up standing about 5' away, making me go to her.

Not missing my excitement, "Now that's what I like to see Sissy Boy, hard and ready," she giggled.

By this time, a few customers were already watching to see what would happen next.

Taking the panties, a pink lace thong number, I turned, bent over to put them on. Big mistake, Swish...Smack right on my exposed ass. She obviously remembered my pink ass from earlier. I should have looked at more than her ass on the walk to the back of the store. The riding crop must have been in her hands already.

Swish...Smack "Any time now Sissy Boy, I have other customers."

I pulled the panties on, enduring three more smacks of the crop. Turning around to face her, I felt the riding crop rubbing my hard-on.

"Yes those look so good on you Sissy Boy," she said as she walked around checking me out, rubbing me all over with the riding crop. Swish...Smack

"Ouch!" I yelped.

"Is that how Elaine has taught you to respond?" 

Elaine has talked to her? How many other people know?

"No ma'am that is not what she taught me."

"Well, I am waiting."

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

"That is much better Sissy Boy." Swish....Smack

"That is two ma'am, thank-you very much," sensing that the other customers were gathering around. By the looks of the nipples, poking through the tops of a couple of the scantily clad women around, this was exciting to them also. What I did not know was that someone had locked the door to the store. The store was no longer open. 

The saleslady, whose name was Sue I found out, also noticed my roaming eyes.

"So I see that you noticed how exciting this is to us ladies. What do you think should be done about that?"

"I am not sure what you mean ma'am," not knowing how to respond.

"What does Elaine have you do when she gets excited?"

"Elaine makes me satisfy her by cleaning up her juices."

"Okay then, follow me Sissy Boy." My cock twitched every time she called me that. I followed her to another part of the store, where the shoes were on display. The other customers followed us. 

Sue pointed to one of the young women, "Are you ready to be satisfied by Sissy Boy?"

"Oh yes, I am so wet right now!"

Sue pointed to the bench in front of us, and the young woman pulled her skirt up over her hips and sat with a leg on each side of the bench. Her wet shaved pussy on display for all to see.

"Okay Sissy Boy, get on your knees and take care of her."

Kneeling down, smelling her pussy, as my mouth got closer, I licked from the bottom up to her clit. A moan escaped her lips letting me know she enjoyed this. I continued to lick her pussy clean, paying close attention to her clit, nibbling on it each time I reached it. Her moans became louder and her hands went to the back of my head, pulling me into her pussy as she let her orgasm go. Forcing her pussy into my face, she bucked as she covered my face with her juices. After a few more licks, she released my head and let me lap up the juices that flowed. I finished licking up the juices from her pussy and thighs, then rose back up to the kneeling position.

Swish...smack...swish...smacks, "Did you forget something Sissy Boy?"

"Thank-you for allowing me to please you ma'am."

The young woman got up, straightened her skirt, and planted a kiss, with a lot of tongue, on my lips, "That was great Sissy Boy! Elaine was right; you do know how to please a woman Sissy Boy. Lay down Sissy Boy."

Not knowing what to expect, soon I was lying on my back on the bench. The young women then reached down to release my now raging hard-on from under the panties. Slowing wrapping her hand around the base, her tongue reached out to lick the pre-cum from the tip. Opening her mouth, she engulfed my cock and began to move it in and out of her mouth. While she was doing this, I found another young woman was lowering her shaved wet pussy down to my lips. My tongue shot out to lick the lips of the pussy now above my face. With a pussy on my face and a mouth around my cock, I was in heaven. Doing my best to give the pussy as much pleasure as my cock was receiving, I licked away, nibbling occasionally on the clit. Soon I found the pussy pushing harder onto my mouth, the juices flowing freely all over my face. I cleaned the pussy as best I could before she was up moving away. I caught a glimpse of my very wet face in a mirror off to the side of the bench. The woman that just had her pussy on my face, leaned down to lick the juices off my face and kiss me. My cock exploded into the mouth that engulfed it, filling it completely with all of my cum.

I saw her walking over to Sue and giving her a deep kiss, "Thank-you for the use of Elaine's Sissy Boy. I had a lot of fun." The other woman did the same thing and I watched as both left the store, smiling as they went.

"Okay, take those panties off and get over here."

I stood up, removed the panties, and crawled over to Sue.

"Put this pair on now," Sue said as she handed me a frilly white lace pair. "Now crawl around for me Sissy Boy."

On my hands and knees, I crawled around, circling Sue. Swish....smack

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

Sue continued to spank my now sore ass for nine more strokes. She sat down on the bench, "Over here now Sissy Boy," she said as she spread her knees for me. 

I crawled over to her and proceeded to lick and suck her pussy until she exploded with her orgasm. Then she told me she wanted me to fuck her good. I moved up to her and placed my cock into her now soaked pussy, slipping it in easily. Starting slowly at first I worked my way up to frenzy, going in and out faster and faster until I exploded deep in her pussy. I was thinking that any one in the parking lot could hear her moans.

After laying there for a couple minutes, catching her breathe, she got up, kissed and thanked me.

Sue walked over, grabbed another couple pair of panties, and placed them in a bag. Grabbing my pants, she reached into the pocket, pulled out my keys, and put the pants into the bag. After putting the rest of my clothes into the bag, we walked to the door. On the way, Sue turned out the lights to the store, locked the cash register. We walked hand in hand out to my car, with me only wearing my panties. Sue unlocked the trunk, threw the bag in, walked over to the driver's door, and unlocked it.

"I had fun, thank-you very much for this afternoon Sissy Boy. Give my regards to Elaine." She then kissed me, swatted my ass, handed me the keys, then walked away. "It was worth the cost of the panties," she smiled as she went on her way.

I drove home with a raging hard-on and a sore ass, only beeped at by a couple of truckers as they noticed how I was dressed. I slept well all night, dreaming of what would be in store for me tomorrow.

To be continued...



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.



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.



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.) 



Sissy Boy Secretary Ch. 07



Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the area. Tammy knew that she would be required to reveal some secrets about her boss' business to make sure Elaine business always profited more, which was okay with her. The job was rather easy, a little filing and typing of letters while answering the phone. It was also great that the job paid really well.

Tammy's boss was a six foot, very handsome black man named Bill Andrews, a name that used to be well respected in the community. Tammy knew that some day she would have this man but up until now all of her advances had been turned down. It turns out that he was very happily married and did not want to jeopardize that. This did not stop Tammy from showing a lot of leg and cleavage any chance she got, and judging from the bulge in Bill's pants she knew it wasn't going unnoticed.

Over the time that Tammy worked there Bill's business declined sharply, although luckily for Tammy, Bill never made the connection. Tammy was providing just enough information to let Elaine win all of the big contracts. Over time the frustration was showing in Bill's attitude. Tammy asked Bill what the problem was one day. He then broke down and told her that his wife was frustrating him, always complaining about not having enough money and stuff like that. What was worse though was the way she was treating sex. She would allow him as much as he wanted but she never really got into it, but rather just laid there like a rag doll. It was driving him crazy. This is what led to making Sissy Boy a slut for black cock.

Sissy Boy's training was coming along great, now for the final step. Elaine decided that this year she would provide the employees and their spouses to a Halloween Party to reward the success of the company. In the process she would give the janitors their special reward, while also entertaining her guests. Since this was going to be a costume party she could allow Sissy Boy to wear a mask to hide his identity from the spouses and also include Tammy and her mom on the guest list.

Tammy and her mom got to the party sooner than Elaine did. Tammy had met a few of the other secretaries and introduced her mom to them. Then had been there about thirty minutes when they heard a commotion and laughter coming from the other guests. Moving over to where the noise came from they saw Elaine holding onto a leash leading Sissy Boy into the room. He was dressed in only stockings, garter belt, a pink lace thong and a hood with holes for my eyes, mouth and nose. His ass of course was bright red from the ride over. Elaine made sure to hit all of the stop lights.

Leading Sissy Boy by the leash, Elaine brought him up to the stage where a saw house was placed. Lisa and Elaine laid Sissy Boy over the saw horse and fastened his hands, feet, and legs to it, securing Sissy Boy in place. Sissy Boy's ever hard cock was pressed firmly against the saw horse, causing him quite a bit of pain. Elaine and Lisa left the stage and continued to mingle with all of the other guests, leaving Sissy Boy exposed so every one could see his predicament, red ass high in the air, mouth accessible to every one.

Elaine made it clear to all the guests that they were free to explore Sissy Boy with one exception; no one was to have his ass as that was to be saved for a special show going on later. Over the next couple of hours the guests certainly had their way with Sissy Boy. 

When Susan got to the stage she and her boyfriend stood in front of him. Susan said, "Look at those cute pink panties. Only a true sissy would wear such things don't you think honey?"

"What real man would let a women lead him around on a leash and then get left up on stage like this," replied her boyfriend. "Look at the way he's looking at my cock! Its like he's hungry for it."

"Well honey it would be pretty hot if you let him warm you up for me. You know how my jaw gets tired when I give you a blow job. Why not let Sissy Boy get you ready?" Susan retorted.

Her husband then pulled out his rather large, about nine inches, cock and put it in Sissy Boy's open and eager mouth.

"Just look at that Sissy Boy go!" "Suck it good Sissy Boy, ya that's the way!" "What a slut!" could be heard from the crowd that was now gathering.

"I told you he enjoyed it mom, just look at the cum dripping down his thighs," said Lisa to her mom as they watched Sissy Boy taking the cock that was invading his mouth. Lisa took the time to slap Sissy Boy's ass enticing a moan heard by every one. This was also the time that Susan's boyfriend decided to fill Sissy Boy's mouth with a big load. Sissy Boy swallowed every drop as to not offend Elaine. Cheers erupted from every one.

Noticing that Sissy Boy had indeed cum Elaine entered the stage, "Okay now that Sissy Boy is finally ready it is time for the show I promised. As you all know our new janitorial staff has by far exceeded the quality of the last staff, so its time to give them a little reward while also enjoying a show. Tyrone, please come up to the stage and bring your staff with you." Tyrone, a fifties man with a well kempt body probably due to all the hard work he did, approached the stage, along with him came five other strapping black men.

"All of us here know how you like a nice tight ass and mouth to amuse yourself, so we thought that no other reward would be as nice as a Sissy Boy to use and abuse for a while. Sissy Boy has undergone some training and has become quite the black cock whore. I'm sure you and your men will find him up to your high standards." With that said Elaine left the stage leaving immobile Sissy Boy at the hands of these big cocked black men.

Tyrone was the first to act; he pulled out his massive black cock and started face fucking Sissy Boy. At the same time the other workers took turn slapping his ass. "Come on Sissy Boy, take all of that black cock you slut!" "Sissy Boy loves this, " another said while caressing Sissy Boy sore cock, or should I say teeny weenie in this case. "His little white teeny weenie is hard now!" laughed another.

At this point Sissy Boy could hear murmurs throughout the crowd, reminding him where he was. This just increased his horniness and he strove to make sure that he made Elaine very happy; knowing what would happen if he did not.

For the next hour and a half Sissy Boy endured the incessant pounding of black cocks in his mouth and ass, the crowd fueling his passion. In between the cocks entering his mouth he could see that quite a few of the guests were involved in their own sex acts which made Sissy Boy happier to perform for them. These black cocks continually shot load after load of hot cum all over and in Sissy Boy. His ass was on fire from all the spanking, plus his asshole was gapping and dripping cum. The panties he had on were dripping not only from the janitors cum but also with his own. It seemed Sissy Boy enjoyed about five orgasms over the period, a fact not lost on Elaine.

To complete the humiliation Elaine had all the black guys give me a shower to clean me off, a golden shower. Sissy Boy was tied to the bench while these guys pissed all over him, cleansing all of the cum from his body. One guy even stuck his pissing cock in Sissy Boy ass and cleaned it out too. This is how the show ended.

Elaine said good-bye to all of the guests over the next hour as Sissy Boy remained tied up. On the ride home Sissy Boy was made to sit in Lisa's lap. What made this interesting was the fact that Lisa had put on her big black strap-on which was now up Sissy Boy's ass. She was also tugging and groping Sissy Boy's cock with the threat that he had better not cum in the car. The discomfort in Sissy Boy's ass was evident by the look on his face. They proceeded to Sissy Boy's house and just pushed him out of the car dressed like a slut. They gave him the keys and just as he was opening the door Elaine beeped the horn, laughing at the expression on Sissy Boy's face, knowing his neighbors would be looking. Elaine smiled and drove off.

*

Thank-you for your comments. As they keep coming I will try to write more. Any ideas are greatly appreciated, just tell me how you like the story to go. To be continued... 



Sissy Boy Secretary Ch. 08



Elaine knew that it was now time to implement her plan to bury her nearest competitor, Bill Andrews... You see Elaine's secretary arranged through the secretarial pool to make sure Tammy, the daughter from next door, got the job as Bill's secretary... As you already know Elaine has used Tammy's information to her advantage and now it seems that Bill was at his weakest point. Tammy informed Elaine about her lunchtime meeting with Bill, where he revealed that since the company wasn't making as much money, his wife had grown apart from him. Now she was nagging him all the time that she didn't even have enough money to get her hair done right any more. Tammy also let Elaine know that her teasing was having the desired results from the look at the bulge in his pants lately. Now he was ready for the final collapse, his last good customer giving there work to Elaine's company.

At lunch the next day Bill had asked her why the sad face, obviously her acting was good. Tammy replied that she was concerned about her mom, "Since mom has gotten the divorce she has with drawn from the world, just moping around all day." Tammy went on to say, "All she does after work is surf the porn sights on the internet."

"Doesn't she work any more? You know to keep her mind off of her troubles." Bill answered back.

"Yes she does still work and puts on quite the show that most people cannot see the problems she's having. It is really just at home that she really shows how all of this has affected her. I hear her vibrator," looking up to gage Bill's reaction, "buzzing and her moaning." She noted that Bill seemed real interested in this. Bill has seen my mom and he gets that look in his eyes when she's around, also a slight bulge when she wears a skirt.

"This goes on every night?" Bill inquired.

"Yes and the things she says are getting crazier and crazier too." Tammy added. "I do not think I should tell you what she says or you may become offended."

"I do not think you could say anything that would offend me, so why not just tell me, maybe I can help." Bill said, with an inquiring look.

"Well you asked for it Bill. I here her saying things like 'suck that black cock you sissy!', 'take that black monster up your ass slut!', and 'take care of that big black cock good you little sissy!'", Tammy said timidly, waiting for some sort of reaction. "I've searched her computer to find out that she has been reading stories on a site call Literotica.com. The most read section is the interracial stories. I read one of them that she has read more than once, actually quite a few times. It involved a white women watching and egging on a black guy to fuck her neighbor's daughter. Does that offend you? Do you think my mom's crazy?"

Bill then said, "Although I have not had any personal experience my self, I have a couple of friends that have related stories about hot white housewives. They seemed to enjoy the power they had over these women."

"Well it seems that my mom would like to have a black guy use and abuse a white lady, so she could direct the action. I have seen her panties on the nights I knew she was reading this story and they were wetter than I have every seen," Tammy continued. "Have you every fantasized about fucking a submissive female while being told how to abuse her?"

Before Bill had a chance to answer Tammy proceeded to explain to him how she came about this predicament, including the details of her father cuckolding her then divorcing her. She also made sure he knew that the cum soaked panties he found were hers and not her moms. Now she wanted to make it up to her and the only way she could do it was to make her fantasy come true. Tammy said that it may just be enough of a shock to bring her mom back to reality.

Tammy shimmed over closer to Bill putting her hand on hi thigh, "So is it really true that all black men have big cocks?" as her hand slowly moved up his leg. Bill was helpless to move or even to take his eyes off of the lace encased tits staring at his face. Tammy knew he was getting excited when she felt his hard cock. As it turns out Bill's eight inches of man meat was at full staff, her teasing taking effect. "Let's go back to the office and discuss this further."

Tammy moved away from Bill to allow his cock to subside a little before heading back, although it did not stay down long. All the way back to the office Tammy made sure to walk in front of Bill, with the excuse of hiding his excitement but instead so she could sway her tight ass in his face. She could just feel Bill's stare at her hot tight ass. She made sure to put on a good show. In the elevator to the office Tammy made sure to rub her hot ass on his cock, causing him some discomfort.

Tammy wanted to test his submissiveness, so as soon as they arrived she pushed Bill into the office, shut and locked the door behind her. "Okay now lets see what you have there big boy! Take out your monster black cock for me to see." Bill instantly, but carefully unzipped his pants and let them fall to the floor. The tent in his boxers was obvious, sticking straight out. "Now Bill, remove the boxers too, don't be shy."

When Bill pushed his boxers down to his ankles Tammy was behind him stroking his ass. She reached around to stroke his big hard cock for him. "You are enjoying this aren't you Bill? You are so hard now. What is making you so excited Bill," Tammy said while wrapping her bare leg around in front of him, rubbing his cock with it. A moan was heard from Bill's mouth when this happened. "Do you want to cum now Bill?" inquired Tammy. I can help you but only if you will help me, and judging from this," she lifted his cock up and gave it a shake, "you are ready." Tammy was surprised at just how submissive Bill really was.

"Yes I will help you with your problem, just finish me off!" Bill said reluctantly.

"Are you sure you want to do this?" Tammy said while starting to slowly stroke his cock.

"Yes, yes, any thing you want. Just let me cum!" Bill said nervously. Tammy was bringing him just to the brink then slowing down enough just before Bill could explode.

"You can cum for now, but you also have to promise me you will not cum for the rest of the week." Tammy stroked him faster and faster. This was turning out much better than Tammy could have imagined. As it turns out, Bill was quite the submissive. Tammy stroked Bill until he exploded with quite a few loads, all landing a couple of feet in front of him. Tammy couldn't help but to lean over and clean Bill's cock with her mouth. She gave it a few licks then told Bill to put it away and remember that he was not to cum until he came over on Friday. Bill pulled up his boxers and pants and Tammy instructed him to get down and clean-up the mess he made.

Tammy watched her boss down on his hands and knees, cleaning up the mess, while thinking that she would have to get that cock in her some time before this was over. This was so much fun for her, and much easier than anticipated. Tammy informed Bill that she was taking the rest of the afternoon off so she could set it up. After all now there really wasn't much work to do around there.

Tammy went straight to Elaine's house to let her know how things were progressing. They started to plan out just how they wanted to do this, (see chapter 09 for these details.) Tammy spent the rest of the week teasing Bill to no end, flashing her long legs and lace thong panties as much as possible. She took every opportunity to flash her tits any chance she got also. Tammy knew from Bill constant hard-on that she was driving him wild. At least a few times a day she would find a reason to rub her hot ass in Bill's crotch, watching him panic, he didn't want to disobey and cum before Friday.

Tammy also 'accidentally' left her black dildo in the family room along with an interracial video she had gotten. Her mom found it and when she asked about it Tammy replied, "Well you know my boyfriend has been out of town so I had to get some relieve." Tammy also took note that the tape had been rewound even though she had stopped it halfway through to see if her mom would take the bait. Boy did she, Tammy would find the tape moved when she came back in, after going to the club with her friends.

Tammy thought to herself, "I love it when a plan comes together."

To be continued in the next couple of chapters, hope you are enjoying them.



Sissy Boy Secretary Ch. 09



Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he never really trusted her fully, which led to the downfall of the marriage.

Here is the story as Tammy told Elaine....

When I was home on a spring break from my college studies I had a big date planned, but I left my sexy lingerie at school, forgetting to pack them. Out of curiosity more than any thing else I decided to check out what Mom had so I could borrow it. I went into Mom's bedroom to see if I could find a suitable replacement. What I found was several sets of sexy panty and bra sets, seems she liked to dress sexy, so I chose a skimpy black lace set to borrow.

The date went great and the sex even better, leaving the traces of our good time lining the panties, soaking them in a mixture of our combined juices. Without thinking, I dropped the dirty lingerie into the dirty clothes bin, right where my father found them I later learned. Instead of inquiring about them my father placed them in a bag, evidence of my Mom's misbehavior he thought. Nothing happened for the remainder of my vacation and I went back to school as I normally did.

Summer vacation was soon upon me and again I was staying at my parent's house but with one noticeable difference, the tension in the air could be cut with a knife. My father was working a lot more overtime and even when he was home, he gave Mom the cold shoulder, barely talking to her. I approached Mom about it but she reassured me it had nothing to do with me but was something she had to handle on her own so I let it go.

My curiosity got the best of me and I needed to find out what was going on, something was definitely wrong. Since neither of my parents were going to tell me, I enlisted the help of a high school friend of mine. Scott has been working with computers since I have known him so it was easy for him to wire the house for video and sound. I helped him place wireless cameras in remote sections throughout the house; parent's bedroom, living room, kitchen, and even in the bathrooms. I could monitor the output of all these devices on the computer in my bedroom. Not only was I able to see video from these devices but I was also able to direct the camera angle to see the whole room.

I monitored the video for the next week but really did not find any reason for my parent's behavior. Mom and I often ate dinner alone while my father worked overtime but the talk was always light and never personal. It was the same thing night after night, we would eat, clean up the dishes then both retreat to our bedrooms. I was surprised when on the third night I saw my Mom turning on her computer, sitting in front of it wearing only her robe. It appears she was reading pornography on a sight called Literotica.com, but I could not read what stories she was reading. My eyes popped wide open when I saw my Mom pull out a big black dildo and start to fuck herself while reading the story. I will have to find out what story it was because in a matter of minutes she was having a massive orgasm, almost falling out of the chair in the process, I guess it has been a while I surmised.

My Mom treated me to a repeat performance two more times over the next week, each ending with Mom in an orgasmic spasm. I did sneak into their bedroom and found out the stories she read involved dominating females and submissive males, you go Mom.

A few days later my Mom nervously came to ask, "Tammy would it be possible for you to find a place to sleep tonight, your father and I have to talk and we need some privacy?"

"That will be real easy Mom, what are you going to be talking about?" I inquired.

"To tell you the truth I am not sure, your father just told me that he had to talk to me about something important, he did not give me any details," she answered.

The dead silence at dinner that night was maddening; no one said a single word. I guess they were both nervous about tonight. I excused myself and retrieved an overnight bag from my room. I kissed them both good night and said I would call before I came home.

I came over here, out of the view of my parents, and waited for my opportunity to sneak back in, I did not want to miss this. I was startled when I saw my father's car leaving the driveway with only him in it. Watching I saw my parents bedroom light go on and I knew this would be my chance. Not making a sound I made my way to my bedroom unnoticed, turning on the computer as soon as I walked in.

I saw my Mom at her computer again, reading stories once more. The dildo did not appear this time so I thought that my father must be coming back and she did not want to get caught. I head my father return at the same time she did, her computer going to E Bay now.

Looking on the other camera, I was able to see that my father was not alone; accompanying him was a young woman barely older than I was. He told her to wait there until he called her then descended the stairs to their bedroom.

He found my Mom sitting nervously waiting for him at the computer desk. Putting his hands on her shoulders he leaned down to kiss and nibble her neck, knowing how horny that makes her, "I would like to try something a little different tonight to spice up our sex life, are you up to it?"

"Since we haven't had any sex in the last few months, normal sex would spice it up," Mom said sarcastically.

Ignoring the sarcasm, "So does that mean you are game, you want to try something new?"

"I am so horny I am willing to do most anything to get you to fuck me," Mom answered quickly.

"I want to tie you up and play with your hot body a while before I fuck you, it would excite me immensely," he said watching for her reaction.

"Well I guess.....what the hell?" as her hands were pulled behind the chair and handcuffed there.

"Do not worry, you will like this," he bent down to cuff each ankle to a chair leg, my Mom now bound in place. His hand rode up her leg, over her thigh and then he put two fingers in her pussy, noticing the wetness. Putting the fingers on Mom's lips,"You are wet already, you like this don't you?"

"It is different, exciting actually as you can see what it does to me," Mom noted.

"Now it is time for you to feel how I've felt over the last couple of months," my father said as he was leaving the room. Mom had no idea what he was talking about and he ignored her screams.

He returned with his lovely, very young 22 year old, secretary in tow, with lust in her eyes. Apparently, he confided in her about finding the soiled panties and asked for her help. Thinking she was going to be helping him with payback, she readily agreed to his plan. It was easy to talk his secretary into helping him since this was one of her fantasies too.

"What the hell are you talking about?" "I did not do anything!" "What in the world is this, who is she?" my Mom continued to yell at him.

"Damn that bitch is noisy, can you shut her up?" Linda, the secretary asked.

"Sure thing, I was hoping it would not come to this but I guess we have no choice," he put a gag in her mouth, securing it tightly. He returned and started passionately kissing Linda and groping her body everywhere.

The clothes flew all over as they stripped each other, both groping and grabbing each other. Linda went to her knees and took his cock in her mouth, "I can not believe anyone would not worship this cock, it is masterful," sucking it all the way in, tongue reaching out to lick his balls, (I wish I could do that I thought to myself.)

"Oh that feels so good!" "Yaa, just like that baby, keep it up!" "Damn this is better than any blow job that bitch gave me!" were some of the comments heard as she continued to give him a wet blowjob.

I watched in utter horror when I saw my father place this young harlot on their bed, licking up her thighs to her shaved pussy. He ravished her with no regards to Mom who sat only a few feet away. When I saw the way he devoured her pussy I wished it was my pussy being eaten. I noticed that my hand was now inside of my shorts, stroking my own pussy; I was getting hot watching this.

He licked/kissed his way up to take a pert nipple into his mouth, flicking it with his tongue. His other hand groped and squeezed the other tit, even twisting the nipple some invoking a scream from Linda.

"Oh my God, that feels so good," Linda yelled when my fathers cock impaled her, "Umm!"

My father pounded away at her young pussy causing Linda's moans to be almost constant now. In and out, in and out, over and over again his cock was buried in her sweet pussy. He fucked her in that position for the next fifteen minutes, what stamina he had, before he flipped her over and took her from behind. As wet as his cock was when he pulled it out told me Linda loved this, as if the moans didn't tell me that any way.

He continued his incessant pounding of this young girl from behind for another ten minutes or so, even reaching around with one hand to caress her tits. I had to admit my father had good taste; this girl had a fine ass. I was totally taken aback when my father pulled out and stepped back, allowing Linda to stand up. I noticed that his cock was still rock hard, standing at attention, ready for more and more he was going to get.

I watched Linda grab around my fathers neck to pull her self up, then she wrapped her legs around his back and mounted him, his cock going in deep. She rode him like a rodeo bull, fast and furious, up and down she bounced time and time again until I knew my father could take no more. Dad dropped Linda to her knees with his cock in her face so she could suck him to orgasm. Linda knew what he wanted so she took the cock in her wanton mouth and vigorous sucked him. I saw my fathers face squint up as he released loads of warm hot cum in her mouth which she eagerly swallowed, not missing a drop.

Linda stood up, my father put his arm around her waist and off they went to the shower, ignoring my Mom completely.

I know Mom couldn't see but could hear the two of them fucking in the shower. I switched to the bathroom cam and watched my Father fucking Linda from behind in the shower. After they were done, cleaned up and dressed my father sent Linda down stairs to wait for him.

Mom was sobbing away while my father undid her bounds, "I guess I owe you an explanation don't I?"

"You are damn right!" Mom said in between tears, "What did I do to deserve that?"

"So you would like to know what this about huh?" her father said as he walked over to the dresser. She watched as her father reached into the drawer to pull out a pair of lace panties in a plastic bag. I could see that the black lace panties were covered in cum, my cum, not hers. Results from my hot date the last time I was home. "You don't deserve it? Do these remind you of anything?" he flashed the panties in front of her eyes.

"I have not seen or worn them in the last at least three months, they came up missing one day," Mom told him. "How did you get them?"

"I found them in the dirty laundry a while back."

"Oh," it was like a light bulb going off, "Was Tammy home from college when you found them?"

"Come to think of it she was on vacation at the time."

"Why didn't you ask me then you stupid bastard? Why the hell do you always think I am cheating on you? I can not take it any more! Get the hell out of here I don't want to see you again, we are getting divorced."

"I didn't say anything because I was so mad, I was afraid I would hit you!" he pleaded.

"I don't want any excuses; you had plenty of time to talk to me before you did any thing. Now just get the hell out of my face!" my Mom roared.

My father left the house that night and it was two months later that the divorce was final, my Mom and me got the house. I never let on to Mom that I knew the real reason for what happened but I will always carry the guilt with me.

My Mom has distrusted all men since the incident, she detested them now. She has become a hermit, never going anywhere except to work or the store, spending most of her free time reading stories and pleasuring her self with the black dildo. I noticed that most of the stories involved a white female dominating a black male which gave me the idea on how to help both my Mom and you at the same time.

Now that Bill is ready for the taking I had an idea that would help you and my Mom. Let's allow my Mom to dominate Bill and have him service Sissy Boy for our hidden cameras. We can make Sissy Boy look totally feminine and let Bill think he is female until it's too late. Can you imagine the look of surprise when he finds out he's fucking a guy in the ass, even better when we show him the video. I really think I owe my Mom this and I would be grateful if you let me do this.

*

Sorry for the deviation but this was necessary to set up the next chapter. See Ch 10 for the final devastation of Bill coming soon (I hope).