It all started my sophomore year of college. I was 20 years old and like most students I loved to go out and party. It seemed that I went out almost every night but somehow still managed to keep my grades up. During the second semester I was running low on cash so I started to look for a job. I was talking to one of my professors and she said she could get me a job working on the web page. I decided to take the opportunity since my major did have me working on computers.

       I met my new boss the following Tuesday. Her name was Anne; she was Farley tall for a woman, about 5’10”. My first thought was how beautiful she was, she was very thin with size C breast and legs that seemed to go on for miles. She was very friendly but told me that she expected to get a lot of work done during the next few weeks. The semester went on like usual and I ended up working for her over the summer. I came to work on the first day at 7:30 a.m. to find a note on my office door “Fred come straight to my office when you get in today”. I was nerves walking down to her office because for the most part we just communicated through the phone or email. Her office was huge. The door was located in the very front and off to the side there were two more doors. One leading to a closet, the other leading to a private bathroom she had a coffee table in the middle of the room surrounded by  a couch and two leather chairs. Her desk was right in front of a huge window and had to chairs on the opposite side of her. When I got there she was sitting behind her desk. Her hair was let down and it went to her mid back; she had on a low cut top so her cleavage was very visible. I sat down across from her and trying to act non-aroused asked her what was up? 

“Shut the door.” She demanded. I did as she asked and then went and sat back down “See the problem is that we found porn on your office computer, and I really look down upon that here. If you want to get your rocks-off you do it on your own time not mine do you understand me?”

“Yes maam. I’m sorry”

“It’s too late for sorry. I’m afraid we’re going to have to let you go”

This was a big problem for me. My parents had started to pay for my college when I got this job and the deal was as long as I had it I didn’t have to pay a dime. I had already spent all my money on booze and other pointless items.

“Please Anne, don’t fire me I won’t do it again I swear”

“It’s too late, company policy”

Please I’ll do anything I swear just give me another chance

She looked at me for how long before she finally spoke again. “Ok I’ll give you another chance, but you have to promise that you will do every single thing I ask you to do or else you are gone. Do we have a deal?”

“YES” I replied so fast without even thinking about what she was actually saying. “Great then we should have a lot of fun this summer or at least I will have a lot of fun” she replied with a smirk on her face. She got up and walked over to the door and locked it. I noticed she had on Knee high black boots and a short skirt to go with her top. She came back and sat on her desk and crossed her legs as she did so I noticed she was wearing a black thong. The height of her desk made her sit higher than me so she was looking down at me when she spoke

“There are going to be a few new rules from now on. First you will never speak while I am speaking. Second you will obey every rule or be punished. Understand me?”

“Yes”

“You will always address me as Miss Anne no matter what. Failure to do any of these three simple rules will result in me punishing you or releasing you of your position. From here on out you are my little slave, you’re the scum of the whole office and need to be taught a lesson. Now take off all your clothes!”

I hesitated “what the fuck are you waiting for get your clothes off this instant” I slowly started to take off my clothes “hand them here” I gave her my clothes as I removed them. I was down to my boxers when she said to stop. She then took my clothes and went over to her closet. She walked in and returned with a bag. Kneel she ordered. I did and she walked behind me and brought a collar out of the bag and attached it around my neck.  She then moved in front of me and looked me up in down. “Now we are going to have to do something about your behavior. Let’s see…” and with that she gave me a swift kick to the balls. I collapsed in pain. “Get up you little sissy”.  I tried to keep from throwing up and knelt up.  “That first one was for hesitating when given an order we still have to deal with that fact that you didn’t call me miss Anne” with that she gave another hard kick causing me to go to all fours again. She walked back to the closet and left me to catch my breath.  When she came back she had a leash in her hand and two small pad locks. She used one to lock on the collar and the other to lock on the leash. “You are to remain on all fours when in my presence understand?”

Yes Miss Anne

“Good now remove your boxers so I can see that pathetic thing you call a penis.” I quickly removed them not wanting another kick in the balls. “Kneel up and spread your legs” I did. Although I was embarrassed I still was starting to get hard. “Look at your little penis. Your liking this, you pervert.” She reached down and grabbed my cock and started to play with it. “You think this is fun? Well that’s good because you are going to be my little slave all summer. Know I have to get some work done but I don’t want you to get bored so stay here” again she went to her closet, this time she came back and tied a piece of thin rope around my sac  and the other end to the corner of her desk. She then tied my wrist together behind my back and laid me down so my legs and arms were under me. This stretched my sack so tight I thought it would rip it right off. She then attached my leash to the heavy chair so I couldn’t move forward at all. “There that should hold you for a while”. She then stepped on my chest and her boot dug into me. She raised one of her heals over my mouth “Suck you fucking perverted sissy” I opened my mouth and sucked on the heel of her boot while she crushed my chest with the other one.  “Good little boy. How would you like a drink?” She removed her heel from my mouth.

Yes Miss Anne,

“Good” she came over and stood above my head so I had a clear view of her black thong. She removed it and set it on my face. “Know open wide and if you don’t you will not be feeling anything in that cock of your ever again” and with that she let out a stream of warm piss. She didn’t even try to get it all in my mouth but soaked my whole face. I couldn’t help but swallow some though it was horrible. She took her know soaked panties and shoved them in my mouth. “Don’t spit those out and they better be clean by the time I get back. With that she left.

I laid there not knowing who was going to come in or when Miss Anne would get back. I finally heard the door open about an hour later. “I’m glad to see you didn’t go anywhere” she laughed as she came in. She looked down upon me and with a huge smile. “Do you want to play?”

“Yes Miss Anne” I tried to mumble through her panties

“Good” She started to untie me but left the collar on. She told me to spit out the thong and to where it. “Know when I enter a room you are to kiss each foot and offer your services to me. Since you didn’t you will be punished again but we will wait until later for that…..Well what are you waiting for!!!” With that I crawled over and kissed each boot and asked how I may serve her. “Well I see that your cock is still hard take care of that but don’t cum until I give you permission!” with that I started to jerk off, Miss Anne sat on one of the chairs and removed her boots. In no time I felt like I was going to cum I looked at her and she nodded “on my feet sissy” and with that I blew the biggest load all over her feet and the wooden floor. “Well look at that, your cock does work but you made a mess clean it up” I started to head for the bathroom to get a towel when she yelled “with your fucking mouth!! How stupid are you” I slowly went back and started to lick my own cum off her beautiful feet. I cleaned up every drop off cum and then worshiped her feet. She shoved her whole foot into my mouth witch almost made me gag. After this I was again rock hard since I did have a foot fetish.

“You are just to Horney for you own good but you’re here to serve me not for your pleasure.” She stood up and kicked me onto my back. She went to the closet and brought a dildo gag with her. “Would you like to see your mistress naked little sissy?”

“Yes Miss Anne” she then stripped down till her perfect body was completely nude. She shoved the gag into my mouth and buckled it. She slowly lowered herself until her ass was right in my face. She rode my face so hard that I thought my nose was going to go raw from being shoved in between her ass cheeks. After she came she removed the gag and told me to go clean up her piss mess that I had made early by not catching it all. I crawled over there and began to lick the floor even though it was mostly dried up by now.  When I was finished I went and knelt in front of her desk. “Go put your thong on” she ordered I did as I was told and came back. “I need to get some work done why don’t you go play dress up and put my clothes on”

“Yes Miss Anne” I went and put her clothes on.

“Why don’t you look like a little slut? I want you to go down to the sex store down town and buy a strap-on dildo. Put it on this card and you might want to get some lube. You have 25 minutes. For every minute that you’re late you will be spanked.”

I couldn’t believe she wanted me to go out in public like this as I headed for the door she stopped me and took a picture “Just a little reminder of what a sissy you really are. Now get going the clock is ticking.”  I got to the store and they had two strap-on dildos the girl that helped me couldn’t keep from laughing. I didn’t know what one to go with. The one was a purple 6 inch dildo and the other was an 8 inch black dildo. I figured she would be using this on me and decided to go with the 6 inch dildo. I walked up to the cash register and paid for it. I looked up at the clock and saw I only had 5 minutes to make the 15 minute drive back to her office.

I knew I was late by the time I got to her office door. I went to turn the knob but it was locked. I knocked but there was no answer. There I stood, dressed in a little skirt wearing panties, a low cut top and boots that were way to small for me, waiting for something to happen. I knocked again but still nothing. I didn’t know what to do I waited for another 20 minutes when all of a sudden the door opened and their stood Miss Anne completely naked. “What the fuck are you doing? On your knees!! Now get your ass in here.”

I’m sorry Miss Anne. The door was locked, I knocked but you didn’t answ…

“Are you saying it’s my fault that you’re late?”

No. I jus

“Well this will not be tolerated. You are 30 minutes late that will be 30 spankings and you forgot to kiss my feet when you saw me. That’s twice in the same day. I’m going to have to think off a way to help remind you of your duties.” She sat down on the couch and picked up a wooden hair brush that was lying on the table. “Remove everything except my thong and get over my knees” I did as I was told. My cock pressed up against her upper thigh and began to slowly get hard. “You will count all 30 and you better thank me after each one.”

“Yes Miss Anne.” With that she smacked my ass with the brush. “1, thank you Miss Anne. 2, thank you Miss Anne.” The first couple weren’t too bad but by the 10th my ass was starting to get sore and tears were starting to form in my eyes. By the time she finished I had tears running down my face and my ass was so sore I didn’t think I would be able to sit for a week.

“Good little sissy. That should keep you from being late”

Yes Miss Anne

“Now let’s see that dildo.” She walked over and removed it. “Well it seems that you went for the smaller of the two. I knew you would that’s why I locked you out. Know go bend over the table.” I did as I was told. She came back with some rope and tied each hand to a far side leg of the table and each of my ankles to a leg of the table. This caused my ass to be stuck up in the air and I knew what was coming. I had never been fucked in the ass before and I was scared shitless. She moved to the front of me and was wearing the strap-on. “This is going to be fun little sissy. Know open your mouth and lube up me cock.” She shoved the dildo into my mouth and I began to suck it. “Aren’t you a good little cock sucker” she pulled out and walked around me and shoved the dildo in my ass. I was in pain as she started to ram me and I began to scream. “Oh now we can’t have that, now can we.” She pulled out and came back with a ball gag and put it in my mouth. She then fucked me for 20 minutes. Towards the end though it was starting to feel kind of good and my screams became more of a moan. “I knew you would end up liking it.” She untied me and had me go to the bathroom and clean off her dildo. When I returned she had on a sports bra and some spandex with white low-cut socks and white sneakers. I crawled to her feet carrying the dildo in my mouth. I kissed both of her shoes and she took the dildo and put it away.  “Go sit in my desk chair.” I did she took the ropes and tied my wrist to the arms of the chair and my feet so they were resting on top of the rollers. “I’m going to go work out but you are going to sit here and wait for me.” She placed the gag back into my mouth. I was tied to the chair wearing only her thong and a gag in my mouth. She pushed the chair into her bathroom and left me there in the dark. By the sink she had a digital clock that said 11:15. I watched as the clock slowly ticked by. I was starting to get hungry and tried to pull on the restraints this was pointless so I sat there and waited. At 1:00 I heard noise outside the door of the bathroom and Miss Anne came in. She was soaked in sweat and looked tired. “I bet your starting to get hungry aren’t you”. I nodded my head. Well I’m going to shower then I’ll see about feeding you. She stripped down and removed my gag only to replace it with her sweaty socks. I could taste her sweat and I loved it. I really did have a thing for feet. She duck taped them in. She turned my chair so I could see her as she took a shower. My cock sprang to life again as I watched her wash her magnificent body. She got out, dried off, and put back on her original outfit minus the boots and thong.

She rolled me out next to her desk and got on her phone “Yes Mary could you bring in my lunch, Thank you”. A panic went over my body, I didn’t know who Mary was and I definitely didn’t want her to see me like this. Miss Anne must have noticed because she looked over and gave me an evil smirk. She removed the tape but ordered me to keep the socks in my mouth. She then untied me from the chair. “On your knees!! Know when Mary walks in you will treat her as you do me that means you will kiss her feet and offer your services, don’t worry I have already informed her of you situation she knows your nothing but a little sissy slave. Don’t remove the socks either and you will address her as Miss Mary.” She walked behind her desk and started working.

I watched the door and it slowly opened. In walked Miss Mary. She was a middle aged woman about in her late 30’s. She wasn’t nearly as beautiful as Miss Anne but she was still pretty. She was about 5’7” with her heels on. She was thin and had about B cup breast. She was wearing a nice white button up shirt with a little black skirt. She had on a pair of Stiletto Open Toe Pumps and I could see her cute little toes that were painted with red nail polish. I crawled over to her and tried to kiss both feet but the socks made me drool and soak her feet rather than just kiss them. “You idiot, can’t you do a simple task.” She yelled as she kicked me away.

Miss Anne came from behind the desk “Oh Mary I’m so sorry this slave is new and still in training come let’s eat lunch and we will deal with him later.”

“Oh Anne you don’t need to apologies for this slave. He will learn in time to behave. Here I brought subs for lunch.” They sat down and started talking as if I wasn’t right in front of them. “Slave why don’t you remove my socks so you can eat.”  I removed her socks and crawled next to Miss Anne. “Open your mouth and Miss Mary will feed you” I did as I was told. Miss Mary took a bite of her sub and started to chew it up. She then spit it all in my mouth. “There you go you little slave. Now swallow it and make room for more.” Miss Mary told me. I did as I was told and she continued to feed me until the sub was gone. “I bet he is thirsty Anne don’t you think?”

“Oh I’m sure he is. I don’t have to go but why don’t you fill up a glass for him or better yet” she walked over to the closet and returned with a dog dish and two riding crops. “Here you go Mary” she handed her the dish and a ridding crop. Mary pulled down her bright pink thong and pissed in the dish. She then set it on the table in between the two of them. “Ok there you go slave drink up” Miss Mary told me. I slowly crawled to the dish and started to lick it up like a dog.  As I was licking they stood up and went behind me. One of the swung the crop and struck my ass. I jumped and both of them laughed at me. “Lie on your back slave.” Miss Anne instructed me. She grabbed the dish and brought it over to me. Miss Mary plugged my nose and when I went to breathe through my mouth Miss Anne poured the remaining piss down my throat. “Good boy” she said as I swallowed it. “Know don’t move” They both went to the closet and came back with rope and other equipment I couldn’t see. “Go lie on your back on the table.”

Yes Miss Mary

They tied me to the table. I was completely exposed with my balls resting just on the table. Miss Mary came with her heels on and stepped right on my stomach. She then took the other foot and shoved the heel in my mouth. “Suck it like a cock.” I did as I was told she pulled it out and then placed the other one right above my mouth “Beg for it”

Please Miss Mary let me worship your foot.

She shoved it into my mouth and I sucked on it. My cock was still hard and Miss Mary stepped off of me. She removed her clothes but left on her shoes. Miss Anne appeared completely naked as well. She handed Miss Mary some Clothes pins and they went and attacked my sack. They put them all over my sack on any place they could find. There must have been at least 20 clothes pins pinching down on me. They were both laughing as I started to buck my hips. Miss Anne spoke “Oh stop that we can tell you like it look at your cock it’s still hard. I think you should be thanking us for giving you this pleasure.”

“She said to thank us!” Miss Mary screamed at me and slapped my dick.

Thank you Miss Anne and Miss Mary

“Good Boy” Miss Mary replied. She got up walked away. Miss Anne crawled on top of me and sat on my chest. Worship my feet until Miss Mary gets back. I started by kissing her heel that was resting on my lips. “Use your tongue.” She barked and I started to lick it and she moved her foot so I was licking her pretty little toes. “Get your tongue in between them.” I did as instructed and worshiped her toes moving my tongue between all of them and then sucking on her big toe. Miss Mary returned and took some pictures. Miss Anne got off me and took a condom from Miss Mary. Miss Mary placed the dildo gag in my mouth started to ride my face.  “Know I’m going to fuck you but if you come before I give you permission you’re going to be so sorry.” She placed the condom on my cock and slowly started to ride me. Time one was going up the other was going down. My face was getting smashed by Miss Mary’s lovely ass and every time Miss Anne and rode me my sack would bounce causing the clothes pins to hurt even more. Even though I was uncomfortable I was still getting closer and closer to Cumming. Miss Mary came and she squirted all over me. She stood up and removed the gag. “I’m going to cum Miss Anne.”

“No you’re not” with that she stopped and got off of me. “Since my slave can’t control his penis will you help me Mary?”

“Of course I would.” She went to the closet and put on the strap-on. Miss Anne lay on top of me so her head was down by my cock and her ass was resting on my face. Miss Mary then began to fuck her and I had a front row seat. They moved to the couch and continued over there. After they had finished they came back and took pictures of me. Then they roughly removed the clothespins and untied me. My cock was still standing straight out in front of me. I wanted to cum so bad.

Pleas Miss Anne may I cum?

“No you may not” she laughed. “Know get on all fours and crawl around like a dog. Go get a drink out of the toilet and come back here” I did as I was told and returned to them. They had me kneel in front of them and they began to tie me up. When they had finished I was hog tied and laying on my side. Miss Anne placed a condom on me and began to jerk me off. “You may cum when you are ready” with that I shot a huge load into the tip of the condom. She slid it off and drained the cum into my mouth. She then took her thong and shoved it into my mouth as well. Last she pissed right into my mouth and taped it shut. She got up dressed and her and Miss Mary left. “See you tomorrow Sissy hope the janitor doesn’t find you” and she shut the door leaving me in her office.