Executive Getaway

My name is Jim and I have always considered myself as a straight guy that was only interested in women. That being said, I am also very dedicated to my work and that doesn't leave much time for dating. There have been many lonely nights spent with internet porn and masturbation. This has been my life for the last several years and I am very satisfied with that. When my boss came to me with a proposition, I was very confused and uncertain about what I should do.

It all started one day when my boss, Mr. Jones, called me into his office. He told me he's had his eye on me for some time and thinks I have a real future with this company and would like to help me "move up the corporate ladder". I was shocked and excited to know that someone had actually paid attention to the hard work I had been putting in. I eagerly told him that I would really appreciate that. It's what he told me next that got me confused and uncertain.

"You know that in a couple months, we have our executive getaway." He was looking me right in my eyes waiting for my response.

"Yes. I've heard about it ever since I started working here."

"We'll, I would like for you to come with me this year. I think it would be a great opportunity for you to network with a lot of executives and would be a way to really get your name out there to people who matter in this company."

Holy cow! I couldn't believe what I was hearing!!! This is a great opportunity for me and how could I possibly pass it up?

"I am so very honored and of course I will go with you. Thank you so very much for this opportunity."

"Well, there is a bit of a catch. You see, all of the men bring their wives, girlfriends, or just weekend hook-ups. It would be very odd if I brought someone that wasn't one of those. So, I would need you to pretend to be my girlfriend for the weekend. For all intensive purposes, you would look and act like a woman the entire weekend. You will get many contacts and network with a lot of people. After we get back, you can simply act like you were there as yourself when communicating with these men. There will be so much alcohol that no one will remember that Jim wasn't actually there."

I could feel my mouth drop open and a look of "What??" wash over my face. I am sure Mr. Jones could see it as well and I am sure he was expecting that reaction. He started talking to me and reassuring me that this was a very positive thing and would be a great opportunity for me. I heard about half of what he was saying as my mind was in overload with thoughts.

"I'll give you a few minutes to think about it but I will need an answer because there is going to be some training involved in order to pass you off as, not only a woman but, my girlfriend."

What option did I have? This was the opportunity of a lifetime for me. This wouldn't be any different than those Halloween parties I went to years ago dressed as a woman. I was concerned about the "training" he spoke about but I guess it'll all be worth it if I end up getting promoted and become a career man with this company. I said, "Yes, I will do it."

I could see the excitement on Mr. Jones' face and my training began immediately. For the next two months, I was trained by several different people on how to do my makeup, walk, act, and talk. It was all very surreal to me but as time went on, I became more comfortable with it and actually got pretty good at doing all of those things.

The day came when we put everything all together and it was my first real dress rehearsal of playing Mr. Jones' girlfriend. I had always been petite and had long hair so the look came pretty easily. I had become very good at makeup. I developed a nice sway to my walk that showed off my slightly plump ass, which I sometimes caught myself walking like that during my regular days and had to stop myself. With a lot of help, I even developed a feminine sounding voice. We presented the complete new me to Mr. Jones and he was noticeably very satisfied.

"You look spectacular! Everyone will be jealous when I walk in with you!"

I was so flattered and embarrassed. Here I was looking like a very presentable woman and having a man compliment me while I still had some feelings of "This isn't right because I am a man". I was very conflicted because it felt so good to hear those compliments but I wasn't I liked the reason I was getting them.

The day was finally upon us. Mr. Jones had packed my suitcase for the weekend. When I arrived at the hotel to meet him, he had me change into my first outfit. It was a rather conservative outfit which I was good with. There were a pair of women's dress slacks, a white blouse, and a matching women's blazer. I was actually happy that they looked pretty neutral and a man or woman could realistically wear them. Then I saw the white thigh highs and garter belt with the thong and bra and breast inserts. I immediately asked Mr Jones about this and he said it was just to remind me that I was a woman this weekend. I reluctantly understood and got dressed. It was weird looking in the mirror and seeing myself with breasts. I then did my makeup and hair and was quite surprised how good I looked. This was even better than our dress rehearsal!

Mr Jones couldn't contain his excitement again. "Oh my!! You look so good!! I can't wait to go downstairs and for everyone to see me with you on my arm!" I was so nervous even with him saying that. Dressing up as a woman for a Halloween party was one thing but going to an executive meeting/thing dressed as a woman and trying to convince everyone that I am a woman was a whole other thing.

"Mr Jones, I'm not sure I can actually do this"

He leaned in and whispered in my ear "Call me Michael."

He then straightened up and said "You look great. You've been preparing for this for a couple months. You're going to make so many connections tonight. Tonight you are Allyssa and you are going to be fantastic!"

For some reason, that made me feel better and ready to go out there as Allyssa. So we walked out of the hotel room holding hands. He would squeeze my hand anytime someone would walk past us and look at me. He knew they were looking at me because I looked so good.

We went into this big ballroom and I was expecting to spend the weekend in meetings but this was a straight up party!! There was music pumping, lights flashing, people dancing and just having a good time. That's not to mention all of the alcohol that was being drank. Mr Jones, I mean Michael, was right! I met a ton of executives and got names, phone numbers, and email addresses. They were all very drunk and none of them are going to remember much about tonight so when I contact them, they'll all play it off like they remember Jim! This is actually working out really well.

The party was over and we Michael and I were back in our room. I went to change out of my clothes and put some sleep clothes on. I realized I had nothing but lingerie to wear. Thanks Micheal for packing my luggage!! I asked him why I didn't have anything to sleep I and he told me that I needed to play the part of a woman all weekend. What if someone came in our room and I didn't look like a woman? OK, I guess I can understand that. I changed and tried to take my fake breasts off but they wouldn't come off. I questioned Michael again and he told me he put a special glue on them and they will only come off when he applies the solvent, which will be after this weekend. He needed to ensure that I played my part for the entire weekend.

I wasn't happy about that but I was really drunk and needed to go to sleep. I laid in the bed and Micheal curled up against me. I told him this was too much but he still stuck with the whole "what if someone comes in? We have to look like we are a real couple".

So, there I was spooning with my boss. What could I do? I'll fall asleep and tomorrow morning will bring a new day. But then I felt something hard rubbing against my ass. I was wearing a thong and matching babydoll so I didn't have much to keep me from feeling whatever that was. I laid there wide eyed wondering what was happening. What I thought was happening couldn't possibly what was actually getting ready to happen. Then Michael whispered into my ear, "Just relax". I felt my thong being pulled to the side and something wet being smeared on my asshole. Then something, I realized was a finger, slipped inside me. I gasped. I'd never experienced this. I think I like it.

He finger fucked me for a while and then I felt a second finger slip in. That filled me up like I've never known. I was really feeling confused but also I loved how good it felt. My ass felt so full. I don't think I like it anymore because I know I like it now!

He asked me if I liked this and what could I say? Hes got two fingers in my ass and I am in heaven so I said I loved it! He asked me if I was ready for what's next. I am pretty sure I knew what he was talking about and as a straight man, I never thought I would have a cock in my ass but here I was. I was so horny from the finger fucking that I actually said "YES!!! I WANT YOU TO FUCK ME".

He must have been lubing his cock because it as he was teasing my hole by rubbing it up and down my crack, he finally started pushing his cock into me. His cock head pushed my hole open and then slid inside and I gasped. "Holy shit!!! I have a cock in my ass!!!" As he slowly pushed his cock deeper into my ass, I couldn't believe what I was feeling. This feels so good!! He was soon balls deep in me and I was questioning everything I'd every known because this felt so good.

He pounded my ass for what felt like hours. I'll never forget the feeling of him grabbing me hard as he shoved his cock deep inside of me and then shot his load into me. That feeling of being filled with warm cum made me explode.

After he came in me, he rolled over and I rolled over and put my arm around his chest. What am I doing?