The following story is fictitious, but based on a few fantasies of mine. I am not the most eloquent writer but I hope you all enjoy none the less. If there are any T Girls out there that might like to help me with this fantasy, feel free to reply. Enjoy!!!
It was December 23 and I was running late for my business meeting with my new boss. I had been out late the night before buying Christmas presents for my friends and family. Oh my god! I thought to myself, I can not believe I am going to be late to the first meeting with our new boss, she is going to kill me. Her name was Lynette Sterling. She had taken over for Jim after he retired. I had never met her before, but had heard that she was quite the strict person.
I came running in the front doors of the building dashing toward the elevator. I was a mess. My suit was all wrinkled, I was sweating and my hear was a mess, boy I am going to make a great first impression.
I gently knocked on the door and let myself into the conference room. The room was full with everyone else, so I made myself to an open seat and sat down. I'm glad you could join us Mr. Nelson, I heard come from across the room. I was almost too scared, but I looked up and there she was, my new boss. She didn't look too scary, she was about 5'7" in her heels and was probably in her late 30's. She had medium length firery red hair that framed her face nicely. She had on a for hugging black suit with a short straight skirt and a white blouse. Her figure was fairly shapely, although her breast were not that large, but that was fine since she was only my boss and I didn't need to be thinking about her tits. Is there some problem, she said in a kind of husky voice like she had been a smoker for years.. No Ma'am I responded, uuh my alarm didn't work this morning. I am sorry and I hope to never have this happen again. Fine she said, now sit down so we can continue with our meeting..
I sat there through most of the meeting, at first just glad that she didn't get any more angry with me than she did, later my mind started to wander and I began to think about her in a more intimate way. I first began to really start checking her out when she had her back to all of us while she was writing something on the grease board. She had on a pair of black stocking or pantyhose, the kind with a seam going up the back. God that looked sexy. She wasn't too flaunty or anything, I guess it was mostly just me and my imagination but I was finding her very sexy. She eventually sat back down and continued talking with us, telling us how she wanted to run things and some of the changes that would be made. She had unbuttoned her coat a bit which showed more of her blouse. When she did this I was able to look into her coat a bit and could see that she was not wearing a bra and had very dark nipples. Boy I guess with tits that small you don't really need to wear a bra, but it would be a little more professional.
The meeting went on for about 30 more minutes when she said that was all for now and told us we could go. Uuh Mr. Nelson, I would like you to stay here for a moment. Yes Ma'am I replied. Shit, now I am going to be in trouble. She stood over by the conference room doors letting everyone out, thanking then for coming. The final person left the room and she then closed the door and locked it. She walked over to where I was sitting and sat down on the edge of the table next to me. Now, Mr. Nelson we are off to a kind of rough start here me and you. Mrs. Sterling, I said, I am very sorry, I really don't know what to say. The truth is, I was up very late last night shopping and trying to get started on wrapping presents. I should have tried to pass off that stupid alarm story. First off, she said. I am Ms. Sterling, I am not married and secondly, I don't tolerate tardiness in my work place. There is something else I was noticing about you while I was talking, it seemed like you were staring at me quite a bit. My face turned red I'm sure. I apologize, Ma'am. I was just kind of taken by you. I find you very attractive. Much prettier that my last boss, well mostly because he was a man. She let out a little giggle and told me that I should be careful not too get over excited, she then looked down to my lap and noticed the bulge that I had. My oh my, I guess my advise is a little too late, she said. She then slid off the table down to the floor. She reached down with her hand and gently rubbed her hand over my ever hardening cock. UUUHHhh Ms. Sterling, I don't know if I should be doing this with my boss. Relax, I the boss, its not like I am going to fire you, well unless you don't play along, she said smiling. I gulped and tried to relax. So what do you find sexy about me Mr. Nelson? Well I love the look of a woman in a business suit, especially with a white blouse on underneath. Your back seamed pantyhose are very sexy too. Well I see, actually these are stocking and not pantyhose, but I like your attentiveness to what I am wearing.
She moved around and stood in front of me, she then put one of her feet up on the arm of my chair. She had on a pair of black suede high heels with a gold metal 3 inch heel. See she said, as she lifted her skirt up her thigh a little bit revealing the lacy top of her stockings. The stockings were held up with a garter belt, which is another thing that drives me crazy. My cock instantly got harder, and I had to adjust myself to get more comfortable. I really like a woman that enjoys wearing sexy lingerie. Well I do, she replied. It helps make me feel very feminine. Why don't you stand up so I can get a better look at you, she said. I did as I was told. I was standing up in front of her, with my but resting on the edge of the conference table. My, you are just a bit excited aren't you. She sat down in my chair and rolled around in front of me. Now don't worry this won't hurt a bit, she said. She reached up and undid my belt and unzipped my pants. Before I could even take in what was happening, my pants and underwear were down around my ankles. She was holding my hard cock in her left hand, with her long red nails wrapped around my shiny cock. Do you like the color of my lipstick, she asked? I bet it will look nice on here, don't you. And with that she slowly slid her warm wet mouth down over my hard shaft. I almost came instantly. Her mouth was very educated, she sucked me in and out, swirling her tongue all around me.
While she was sucking on me, she reached down with her right hand and was rubbing herself under her skirt. I reached down and began to gently massage her breasts with my hands. Her tits were maybe a b cup, but they were very firm and perky. I noticed that her nipples became very big and hard, so I rolled them back and forth between my fingers. She moaned a bit witch only made her suck me harder. I was almost ready to cum when she pulled my cock out of her mouth and said, No, I can't have you go cumming in my mouth and on my face, we need to be able to leave out of here and not be all messy. I have an alternative for you. She then stood up and bent over the table. She lifted her skirt up over her ass, exposing her lacy black bikini panties. She pulled those down just enough to expose her asshole. Now, if you can think of a way to lube up that hole, then it is yours, she said. I eagerly dropped to my knees and began to lick and tongue her tight little hole. I was getting even more excited by doing this and I wanted to see how wet she was getting, so I went reaching up her skirt. She pinched her legs together and said that was not advisable. You might find something you wouldn't like.
Huh? I thought. Its my time of the month she replied. Oohh ok, well sorry. Her ass was plenty lubed up with my saliva, so I stood up and gently began to work my swollen cock into her ass. I fucked her in the ass for several minutes but couldn't stand it anymore with all of her wiggling and I exploded like I hadn't done in a while, deep in her ass. It was all I could do not to scream. After I recovered I pulled up my pants and tried to straighten myself up the best I could.
Ms. Sterling, I must say, you were wonderful, but I feel bad that you weren't able to get off like I did. She told me that was fine. She just wanted to please me. I was still very horny and wanted more than before to please my boss. Don't worry Ma'am, I have eaten pussy before when there has been blood, I really don't mind, and kind of like it. Well ok, she said, but I must tell you, its not like other time I assure you. You may, but only if you promise not to run out of her. Uuh yeah sure that's not a problem I told her. Boy I thought, she is sure making a big deal out of being on her period. She stood there in front, I turned her around and set her down on the table. I grabbed onto the waist band of her panties, with that she lifted her legs up in the air and I pulled them off. I wanted to leave her skirt on because it looked very sexy. She had her legs squeezed kind of tight together, but I would work my way between them. I started down at her feet, licking and sucking on her skin through her stocking. My cock began to grow in my pants again. As I began kissing at her knee, I grabbed each knee with my hands and gently pulled her legs apart. What I discovered next, almost made me pass out. In between her legs was not a pussy like I was looking for, but a cock. This woman had a dick, like me. She was not a woman at all.
She looked very embarrassed and tried to get up. I held her down and said to wait a minute. You know, you didn't need to lie to me either, I said. I am sorry she said, I just didn't know how to tell you. What that you were really a man? Fuck, I don't know how to take this. Well you could take it in your mouth like I did yours. HUH??? I thought to myself. Uuhh no thanks, I am no fag. Look at me she said, do I not look like a woman? Yes you do, but this is odd for me. I must admit I was feeling very horny, and wanted to return the favor to her. And with that I slowly open my mouth and pulled her limp dick into my mouth. It was very odd at first, I didn't really know what to do. Don't worry she told me, I am clean if you are worried. Just do to me what you think would feel good to you. I began sucking on her "big clit" it was kind of limp in my mouth but soon began to grow as I continued to suck. I looked up at her and she had unbuttoned her blouse and was pinching her big dark nipples. The thought of that was so exciting to me, here I was sucking this cock which was attached to a beautiful woman. Her dick was pretty hard now, I could no longer hold the whole thing in my mouth. I could hear her moaning and feel her wiggling around, this made me so hot, my cock was raging hard again. I was so into this. I didn't know what to think of myself. I have always loved women but here I was sucking cock. I tried not to think about it too much, but could help myself. I would suck hard just on the tip of it while I gently stroked her shaft and would occasionally gently squeeze her balls. Her cock and balls were all clean shaven which was even more exciting. I was so excited by my boss, I wanted to have more of her, I wanted to feel her inside me. I pulled her hard dripping wet cock out of my mouth and told her that I wanted to feel her inside me. She told me no, not this time. She doesn't want to scare me too much. I agreed and continued to lick and suck her cock. I knew she was getting close to cumming because she was moaning very hard and was having little spasms. I didn't know what I was going to do with her load, but she soon answered that for me. She grabbed onto my head and pulled herself out of my eager mouth. I was told to open my mouth wide, which I did without argue. She shot her hot cum all over my open mouth, lips and face. It felt so incredible. She wiped my face off with some tissues she had in her purse, but not before kissing my very passionately.
Now Mr. Nelson, I am sorry if this was more than you wanted from your new boss, but I think you are going to go far in this company, she said grinning. No one ever knew about our little thing in the conference room, which was good, but from that day forth, my boss and I got along very well. I even got to feel her inside me. I will tell you about that at another time.