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My Business Trip
By Joanie
Once a year I had to travel to San Francisco for a conference that lasted a week. My boss and I would usually take the Friday flight out to play golf and the last flight back on Sunday after we had played 18 holes. He liked the Titty Bars and so did I. We both loved large tits and talked about them often. The only woman in the whole division that had a large rack was Miss Katherine but she had been rumored to be a Dike.
We were both looking forward to our usual trip when he had to have knee surgery and wasn’t going to be able to go. He was very disappointed but I figured it would be great to go by myself anyhow. I knew I’d be able to pick up some Babe with large hooters when I was out there to have a good time with and didn’t really want to play golf anyhow.
I had taken Friday off to catch up on some yard work and didn’t go in until late Monday morning. When I arrived at work many of my Buddies at work looked at me and smiled. I wondered what was going on but I didn’t think anything about until I met with my boss that afternoon. I came in and sat down and he told me that he was going to send someone with me since we already had two rooms booked and they couldn’t be cancelled. I thought great, I’ll take Mike with me. He let me know that Miss Katherine from the Pharmaceutical Division would take his place. I thought “Oh man…what a nightmare this is going to be”. I tried to get out of it but he said that she had worked out there and had some contacts that might be helpful to us.
Miss Katherine as we called her, was a very tall buxom blond in her mid-40’s that always kept her hair up in a tight bun like an old School Teacher. She always wore long dresses with high collars and dark rimmed glasses that sat on the end of her nose. She was very authoritative, demanding and domineering. No one at the office knew anything about her except that she had worked in California and had a Niece that flew in to visit from time to time. I couldn’t believe that I was going to have to spend a week with her. Man…, what a Bummer.
On Friday I checked my bags, got my boarding pass, and carried my briefcase on the plane and was puzzled but relieved when I got to my seat and found that Miss Katherine wasn’t anywhere around. Maybe she had missed the flight or was going to take another one. I didn’t really care as I wanted as little to do with her on this trip as possible. I was in 22B which left the isle seat and the window seat open. Just then a very pretty young woman around 20 or so came up and put her bag in the overhead compartment. She was petite with long dark hair and a pretty face. She was wearing a very short silk mini skirt and a low plunge mid-riff silk top that was barely holding her large breasts. She had great cleavage and I could see her nipples through her top. I thought things must be picking up when I heard her say in a sweet soft voice “Excuse me Sir, but I think I have the Window Seat”. With that she started to squeeze by me to her seat. I could smell her perfume and her large breasts were within 8 inches of my face as she went by. She smiled as she sat down and said “Thank you, you’re very sweet”. My I thought…she’s delicious!
After the plane had taken off the Stewardess came by and asked if we wanted a drink, pillow or blanket. I got a cup of coffee and the pretty little thing next to me asked for a glass of white wine and a blanket. Later when the stewardess returned to pick up our treys, the little beauty next to me leaned over and brushed her breast against my arm as she handed the trey to the Stewardess. I was very aroused at this point and found her to be very exciting. I could feel the bulge in my pants grow. Just then, she put her hand in my crotch and started fondling my cock and said “Do you think I’m pretty?”. I was a little put back by her question but replied “Oh yes, you’re very lovely”. Then she said “Does this feel good?” as she unzipped my pants. All I could do was say “Oh, Yes…” and she smiled as she pulled the blanket over my lap. I put my hand on her leg and starting moving up her thigh when she crossed her legs and said “Not just yet Baby…”. As she kept stroking my cock she was fondling my balls and she got close to my ear and started to whisper. I could feel her erect nipple against my arm as she said “Do you like this?…, Can you cum for me Honey?” Just then she put her finger in my ass and I almost screamed! I couldn’t hold back anymore as I released a big load of wet sticky juice in her hand. She smiled and then she said “My Mistress said you would like that”.
It took me a few seconds to speak but I was curious as to what she meant and I said “Your Mistress…, Who is your Mistress?”. She replied…, “She is sitting right behind us with two of my Girl Friends”. Being inquisitive I turned and looked over the seat and saw Miss Katherine sitting between two gorgeous blonds. Miss Katherine looked up at me over her glasses and broke a small quick grin. As I turned back I could feel the panic set in. She was right behind me and she knew what was happening all the time. She could tell my wife and the people I worked with as well as Frank, my Boss. Oh man…, what seemed like a wonderful encounter had suddenly turned into an embarrassing nightmare. I was screwed! I knew she would use this to her advantage and I couldn’t do a thing to stop her.
I’d wondered where she was when I didn’t see her before I boarded the plane and now I’ve let her Niece jack me off in the seat right in front of her. One question I was still mulling over in my mind was…what did the little beauty mean when she said “My Mistress said…?”. I couldn’t figure it out but that was the least of my worries at this point. All I wanted to do was climb in a big whole for the rest of life…
When the plane landed I grabbed my briefcase and made a beeline to the exit at the opposite end of the plane. I my panic in took a wrong turn and left the terminal without picking up my luggage. I said, the hell with it I’ll pick it up later. I certainly didn’t want to run in to Miss Katherine until I had thought things out and figured out what to say. I grabbed a cab and went to the Hotel and checked in hoping I would get there before she did. When I got there I was handed a message saying that I was wanted in suite #1500 at 8:00 PM to pick up my luggage and was signed “Care to share a Blanket again?”. Oh my…things must be looking up! The little Babe with great hands from the plane wanted to see me again and I would love to get her in my room for the night.
I got up to my room at around 7:00 PM and realized that I didn’t have any clean clothes to wear. I took a quick shower anyhow and shaved with the electric that was in my briefcase. I didn’t wear any underwear as I didn’t have anything clean and I put on the same shirt and suit I had on from the flight. I was anticipating a wonderful rendezvous’ and thought I wouldn’t need them anyhow. I left my room on the 10th floor at about quarter ’til eight and got off the elevator and walked down the hall to suite #1500. My Cock was getting hard as I thought about what was about to happen and I wondered what her nipples and pussy would taste like. I reached suite #1500 promptly at 8:00 and rang the door bell.
I waited a few minutes and was about to push the button again when the door opened and there stood the little hot thing from the plane. She was wearing a short purple silk skirt with a see thru matching bra and thigh high stockings. She had lovely large breasts with nice pink nipples and a matching purple collar. She said in a soft sweet voice “My name is Little Bite” and gave me a kiss on my lips with her tongue probing my mouth. Then she said “Please come in and meet my Sisters”. As I came into the living area I recognized the two beauties that had sat next to Miss Katherine on the plane. One of them got up and came toward me. She had long blond hair and was wearing a short sexy white Nurse’s uniform that was low cut with sheer white stockings attached to her garters. Her large soft breasts were about to fall out of her dress and she was wearing a white collar. She slowly walked up and kissed me very passionately as she put her tongue in my month and fondled my butt. She said “They call me Yummy…” as she turned and walked away. She had a nice firm ass and I could see she was wearing a red throng.
Next came the other beauty I had saw on the plane. She was tall as well and had long blond hair styled differently than Yummy’s. She was dressed in a very sexy low cut blue Police Woman’s outfit with sheer blue stockings and a garter with spiked heels. Her breasts were enormous and were peeking out of her dress just below her blue collar. She slowly strutted up to me and kissed me as she fondled my cock and said “My name is Juicy, won‘t you sit with us?”. As she did, Little Bite brought me a beer and sat on my lap.
I was astonished! I was absolutely in ecstasy! I couldn’t believe my luck when I started getting a little dizzy. My eyes got blurry and I felt very sleepy. My beer had been drugged and I was losing my balance. As I started dozing off I heard a voice in the background say “Is she out yet…?”. Then I also heard the same voice say “Called me when she has been prepared for me”. Then just before I blacked out I heard three voices say “Yes Mistress…”.
I don’t know how long I had been out but when I woke up I had a headache and my butt felt funny. As I started to come around, I realized that I had something tied around my genitals and something had been pushed in my ass. I also realized that I was chained to a bed face down and I was wearing a pink bra, pink stockings, pink silk panties with white ruffles and a garter belt under the sheer pink teddy I had on. My legs, underarms and pubic hair had been shaved and I could see from the mirrors that I was wearing make-up with pink lipstick, a long blond wig and my nails had been painted pink. I also had a pink fur collar around my neck and I was wearing pink spiked heels and had pink toenails.
I couldn’t believe it! I was pissed…why would those three Chicks do this to me? What did I ever do to them? They came on to me…I didn’t come on to them. I had to get out of there and go back to my room. Suddenly I called out “Hey where are you”. “Let me out of here”. As soon as I got my last words out I felt a big hard thwack on my ass. “Ouch! I screamed…, that hurt”. “Who did that?”. “What the hell are you doing to…”. Before I could finish my sentence someone had come in and put a strap around my head and stuffed a ball in my mouth. I looked up…and it was Miss Katherine from my work.
She was dressed very differently but I could tell it was her. She was sitting in a chair with the three beauties standing next to her. She was dressed in a tight black corset with her breasts fully exposed holding a riding crop. She had on pair of black leather thigh high boots over black stockings that were attached to the garters from her corset.. Her breasts were enormous and perfectly shaped with gigantic nipples. She was absolutely beautiful…I couldn’t believe it was really her. All this time in the office and this is what she really looked like under those long dresses. I was amazed at what I saw! I couldn’t believe how gorgeous she looked…!
She got up from the chair and approached me slowly. I could see that her pussy was completely shaved and I felt slight movement in the panties I was wearing. When she reached the bed she put the riding crop on my bare bottom and said “I am Mistress Katherine and these girls are my play things…”. After a pause, she spoke again saying “Do as I say or you will feel the discipline you deserve, you little Sissy Slut”. With that she brought the riding crop up to my face and wiggled it at me, then walked out with Yummy and Juicy behind her.
Little Bite removed the strap from my head and the ball from my mouth and put it in a drawer next to the bed. Then she told me to relax my ass as she was going to remove the Butt Plug from my ass. As she removed it I felt a large drainage from my cock. She undid the chains from my arms and legs and handcuffed my hands behind my back. She stroked my cock a few times and said “This should make you more comfortable Baby” and left the room…
After laying there awhile I started to feel aroused with what I was wearing. The bra and stockings felt good on my freshly shaved legs. I liked the feel of the panties the most and I could feel the soft hair of the wig against my shoulders and I wanted to see what I looked like with it on. The bra and baby doll nightgown felt good on my chest and stomach. I had become excited and the inner part of me I had never know was starting to surface. I felt very good and was extremely turned on by being dressed like a girl.
In a few minutes Miss Katherine came into the bedroom and her girls followed her. She told Little Bite to undo my handcuffs and instructed me to kneel in front of her. As she was standing in front of me she held a long thick strap-on in her hand and said “As long as you are an obedient Sissy Girl you can please me by satisfying my girls”. Then she said “If you don’t…, you will receive the discipline you deserve. Do you understand?”. I looked up at her and said “O.K.”. She quickly grabbed me by the collar and said “Say…Yes Mistress” in a harsh tone. I quickly replied “Yes Mistress” as I hoped this would calm her anger.
At this point I was willing to say anything to get out of this mess and I didn’t want to miss the opportunity to enjoy a sexual encounter with the three beauties on the bed. They were all very hot and I wanted to lick them senseless and drill their eyes out. Little Bite was dressed in a matching red bra and thong set with her full breasts nearly exposed. Yummy was wearing a baby blue corset with matching stockings attached at the garters and her large breasts wiggled slightly as she moved. Juicy was wearing a white corset with white stockings and white panties. Her breasts were about to fall out and I could see her large pink nipples were erect. They were all truly lovely and I was about to experience the fantasy of a lifetime. I was extremely aroused and I could hardly wait.
She then instructed all of the girls to stand up on their knees facing me and instructed me to get on all fours on the bed facing them. Miss Katherine stood behind me and then she addressed the beauties saying “O.K. girls…, remove your panties. Our new Sissy Slut is here to please you”. I was so hard I couldn’t stand it until one by one they each removed panties to expose a full set of cock and balls. I was dumbfounded! I was without a doubt flabbergasted! I was hoping for the opportunity of a lifetime and was being told to suck their cocks.
Then I heard Miss Katherine say “ Come on my Sissy Slut, let’s please my girls”. I hesitated for awhile and then started to speak saying “But…”, and that’s all I got out of my mouth as I felt a hard thwack across my ass. It was Miss Katherine’s riding crop. Then she said “Do as I say or you’ll be very sorry!” As she said this she reached around and grabbed my cock and started to squeeze. I felt her pull my frilly panties down and squeeze my ass as she poured a creamy liquid on my back which started dripping down through the crack of my ass. I could feel the strap-on I thought she was going to use on the girls being rubbed between my cheeks. I wasn’t sure how I would take this but after the butt plug was removed and I was wondering how something like this would feel going in and out of me.
Then I felt her finger enter me as she started moving it around in and out of me. It felt good and my cock was growing in my panties. Then I heard her say “You like that don’t you my little Whore?” and “That feels good doesn’t it Bitch?”. Then she added “You want this Sissy Slut?” as she put the head of the strap-on against my asshole. I wanted to say no but I couldn’t. The truth was, I did want her in me and very deep. I wanted to feel her going in and out of me, hard and fast. I started thinking about all the times I had done this to a chick in my life and how much they enjoyed it, and now I was about to find out. Before I could think to say “No…Stop”, I blurted out “Yes”. Then she said “Yes, what?”. I replied “Yes Mistress Katherine”. Then she said “Say, Please…”. I was so excited by now I couldn’t think straight and I was out of control. All I could do was beg. So out of the blue I screamed “Yes Mistress Katherine…, Please…, Please Fuck Me Hard!!!”.
As soon as the words left my mouth I felt her large big cock enter me all the way up my ass. She had pushed her cock as deep as she could as I felt her stomach against my ass. As she continued this I looked up to see the three beauties had stood up and were kissing and fondling each other. I liked seeing them lick and bite each other’s nipples and stroking each other’s cocks while they watched me looking at them.
Then I felt a slight slap on my ass from Miss Katherine as she said “Come on girls…let Sissy Slut taste your cocks”. With that they all came closer and started rubbing their cocks on my face and lips. Then I heard Miss Katherine say “That’s it you little Sissy Slut…, lick their balls and suck their cocks” as she slapped me across my ass again.
I was so hot I couldn’t take it anymore! I had never done this before but I was beyond ecstasy and my erotic hunger had taken over. I put Little Bite in my mouth and started to suck her warm cock. She was appropriately named because she was small as compared to the other two but she caressed my hair and face and smiled at me. Yummy and Juicy continued to stroke their cocks and kiss as I licked and sucked Little Bite. Then Miss Katherine said “That’s it…In and Out”, then she added “Come on Little Bite, give Sissy a nice load to swallow”. I didn’t know if I was ready for this but I couldn’t stop now when a hot fluid began to fill my mouth. I didn’t want to swallow when I heard Miss Katherine say “That’s it Sissy…Drink, Drink it all up”.
After Little Bite had expended all her love fluid in my mouth, I felt her withdrawal and Yummy quickly put her cock in my mouth. Her cock was considerably larger and I was barely able to take the whole thing. I began caressing her balls while she fed me her throbbing long cock. Miss Katherine spoke up and said “Juicy…, do you have a surprise for our little Sissy?” When I looked up at Juicy she had a smile on her face when I felt her cum on my forehead and nose. Then Yummy held my head and pushed her cock deep down my throat. I started to gag when I felt the gush of her load come out of my mouth and drip down my chin.
By this time Miss Katherine had started slowly withdrawing from my ass and the three beauties moved off the bed and stood on the floor. When Miss Katherine stood back on the floor she dropped the strap-on and climbed back on the bed and told me to lye down on my back. I did as she told me and she moved her pussy up close to my face. Then she said “Stick out your tongue my little Sissy Slut…I want to fuck your face until I come”. She began rubbing her cunt up and down on my face as I licked her vigorously with my tongue when I felt someone’s thighs against mine. It was Little Bite and she sat on my cock and started fucking herself. I could feel her little cock bounce up and down below my belly button when I felt hands starting to stroke my cock as she fucked me. I could feel my balls being massaged and licked while Little Bite’s tight ass went up and down on me.
I started to hear Miss Katherine moan and her pelvic movement quickened. She was rubbing her clit on my nose as she started giving me instructions on how to please her. “That’s it” she said. “Lick my wet Cunt…you Whore”. “That’s it…Suck my Clit… you little Slut”. “Faster…Faster”. My tongue flicked in and out and side to side as fast as I could. I could feel my cock starting to cum in Little Bite’s ass when suddenly Miss Katherine let out a loud groan and picked her pussy just slightly away from my face. I immediately felt a strong gush of squirting fluid start to spray my face. After a deep sigh she said “That’s for you my Sissy Slut”.
I was numb. I couldn’t move and I didn’t really want to either. I didn’t care that I had cum all over my face nor did I care that I was still dressed as a little Sissy. I had enjoyed the whole experience and found that I liked having someone cum in my mouth. I was surprised but I enjoyed having my ass reamed out by my Mistress.
In the afterglow I felt good knowing that I had experienced something I had deep down always needed. My tongue and jaw hurt and my ass was sore but I felt totally fulfilled. As I lay there exhausted, Little Bite brought in some drinks and she and the other two beauties smiled at me. Miss Katherine looked at me and said “Sissy Slut, I have made you my Bitch and you will serve me when I see fit”. Then she added “I will check you each week at work and you had better be wearing Panties. Do you understand me?” I replied “Yes Mistress”.
I was pretty wiped out and started to feel a little dizzy. I knew I was tired but I hadn’t expected to just fall asleep this way. Then I realized…I had drank something that was drugging me again. I couldn’t fight it this time and just let myself drift off.
I woke up very late that night in bed with my suit, shirt, socks and shoes on. I was back in my own room on the 10th floor. As I lay there, I looked around the room and saw my luggage. When I finally raised my head up I saw something on my dresser. I walked over and picked up a pair of pink bikini panties with a note on top. The note read “Make sure you wear these to work for next week‘s Staff Meeting…, I’ll be checking”. It wasn’t signed but it didn’t have to be. I knew exactly who it came from…
The End
