Caught with Consequences

My name is Stephen, and I'm a grad student at the local business college. I've been at my job for less than a year, and as the new guy in the office, I thought that putting in some overtime would make an impression on my boss. Well I certainly made an impression, but it wasn't quite what I had originally intended!

I was hired as a paid intern, and as such, I spend a lot of time working directly with my boss. It's a fairly small company, with just a few employees in our building, most of which we almost never see. There is an associate office across the street with quite a few staff. Natasha (my boss) is the owner of the company, and is drop dead gorgeous! She's friendly, sexy, and a little flirtatious, yet very no-nonsense when it comes to matters of business.

As her intern, I was spending a lot of time working one-on-one with Natasha, and while I was learning a lot about the business, I was having a super hard time concentrating on work due to working so closely with such a hot, sexy woman. Natasha has perfect porcelain skin, and her makeup is always done tastefully, but with just a hint of sexy. Her blouse unbuttoned just far enough to show a tad of her obvious ample cleavage, and her skirts are usually just snug and short enough to show her sweet round ass and long shapely legs. Her stilettos clicking on the tile floors as she moves around the office always caught my attention and even the slightest waft of her sweet perfume always turned me on a little. Typical guy right?

As we worked together on projects, she was always very professional and task oriented, but when we were just chatting, her flirty side usually showed a little, making it even harder for me to keep my head in my work. I figured if I worked some overtime in the evenings, I could get some work done without being distracted, and that worked pretty well for the first couple days.

Then one evening as I was working alone, I noticed a door in her office that I'd never seen opened. Being the only person there, I thought I'd snoop a little. Turns out it was just a small closet that Natasha used to keep a couple changes of clothes in. There were a couple blouses and skirts hung neatly along with a satin and lace camisole. A small night stand with a couple drawers contained a couple pairs of lacy panties and matching bras as well as a couple pairs of silky stockings.

I closed the closet door and went back to work, but couldn't stop thinking about the closet, and soon found myself standing in front of the opened door again. Never had I thought even one time of myself being anything but a 100% normal run of the mill guy. I play softball and go to the bar and with my buds, and I've certainly dated more than a few girls (though I'm not dating anyone right now). That being said, all I could think about right now was Natasha...how looking that sexy all the time must equate to feeling sexy, and if that's the case, she must feel incredibly sexy all the time.

I suddenly had the overwhelming desire to know what that feels like. Even though it seemed weird, I couldn't help myself. I stripped off my pants and underwear, took a pair of the lacy panties and carefully slid them up my legs. They were quite snug, and frankly looked hot in how they barely covered my round ass. I loved the feel of the soft lace on my now hardening cock, and I stood there admiring them for a couple minutes. Loving how the panties felt and looked, I quickly stripped off my shirt, and with trembling hands, slipped the camisole over my head. The satin and lace felt incredible on my tender nipples, and I felt so sexy...and naughty!

After a few minutes, I took the camisole and panties off, and carefully put them back exactly as I found them, for fear of Natasha finding out. That night at home, I was masturbating while thinking about how sexy I felt wearing Natasha's lingerie, and I came harder than I have ever cum before. I knew this was just the beginning!

When I saw Natasha the next morning at work, I was so nervous thinking that maybe she found out what I did. I kept watching for clues that she was mad, or suspicious, but those feelings soon turned to feelings of envy and curiosity. I wondered if she was wearing the same panties that I wore last night...man what a turn on! The rest of the day was spent ogling her when she wasn't looking, and fantasizing about her, kind of like every other day up till today.

That evening I decided to put in some more OT, so after dinner I went back to the office. Once I was in and locked the door, I went directly to the closet. I couldn't really tell if she had been in there that day, but I didn't really care, and I just couldn't help myself. I really wanted to feel that sexy feeling again, so I stripped naked and slid a pair of her dainty panties up my legs. Man I loved the way they felt!!!

I had the camisole in my hands when I saw the matching bra lying there. Thinking about Natasha's sexy tits, I just had to try it on! The bra clasped in the front, so it was quite easy to put on, albeit it was pretty snug. With the bra and panties on, I slipped the camisole on, and then checked myself out in the mirror. I was in heaven, it all felt so soft, snug, and oh so sexy.

Then I saw the stockings lying on the night stand, and I pondered for a moment..."Do I dare put them on?" Against my better judgment, I just couldn't stop myself!!! I slid those silk stockings up my legs and I almost came right then and there! Here I am, wearing Natasha's sexy lingerie, prancing around her office, imagining this is how she feels every minute of every day!

After about 30 minutes of sashaying around the office feeling the satin and lace against my skin, I figured I better take it off before I mess something up. I made sure to put everything back exactly as I found it, got dressed in my boring old boy clothes and tried to do a little work. I was getting very little accomplished as you might imagine, so I locked up and headed home. As soon as I got home I hit the shower, and in no time at all, produced an eruption of cum from my throbbing hard cock.

The next morning was a lot like the previous, I was so nervous that she might have found out. She seemed completely like her normal self though, so it was business as usual for the rest of the day. That evening when I went back to the office again, I was feeling a little guilty for what I had been doing, but again, I just couldn't help myself. I quickly got naked and put on the bra, panties, and camisole. The night before I went ahead and shaved my legs, because I wanted to feel those silk stockings directly against smooth skin...and I wasn't disappointed!!

As I stood there, I looked at the skirts and blouses hanging in the closet and though,"Should I? Could I?" At this point, how could I not? I took one of the blouses off the hangar and carefully put it on. It was quite snug, and my hands were trembling with so much excitement, I could hardly do the buttons, but once I got them all done up, I was surprised how good it looked. The padding of the bra gave me a fairly feminine shape, though nothing like Natasha.

Next I took down a skirt, stepped into it, and slowly zipped up the back. The skirt was also pretty snug but it showed off my ass pretty nicely! I then looked at myself in the mirror and from the neck down, I actually looked like a business woman, although I wasn't wearing pumps. I tried squeezing my feet into a pair of Natasha's stilettos, but no luck, they were just too small. In any case, I felt so pretty and sexy, and imagined this is exactly how Natasha must feel every day while working. I thought, "Dang, what a lucky, lucky girl!!!!"

I wanted to feel that too, so I sat down at her desk all dolled up to just take it all in. As I was imagining I was her working away while all dolled up, I opened a desk drawer and saw a tube of lipstick. I didn't even hesitate; I went to the mirror and moments later, my lips were the same luscious red that Natasha's were every day. I sat there and actually did some work while all dolled up, and it was awesome!!

After about an hour, I figured I better started putting things away. I went to put the lipstick away first but when I opened the drawer, I noticed way in the back behind her makeup was a life sized dildo! As I was sitting in her chair, wearing her clothes, tasting her lipstick, all I could think about was Natasha, on her knees, with her luscious lips wrapped around some guys cock. Just the thought was SO SEXY, SO HOT!!!

I thought to myself, "No doubt that must have happened at some time in this office, and here I am wearing her clothes and holding her dildo...I just have to know what that feels like!" So I knelt down in front of her chair imagining there was a guy sitting there with his throbbing cock right in my face, and I instinctively leaned in and slowly took that dildo in my mouth. I swirled my tongue around the head getting it slick with my saliva, then I slowly slide it deeper into my mouth.

Having received a few blowjobs, I knew the mechanics, so I started slowly bobbing up and down, imagining myself as a hot office girl on her knees sucking a cock. I have to admit, it was fun, so I started putting a little more enthusiasm into it, bobbing deeper until I felt the dildo near the back of my throat. I felt a gag coming on so I pulled back a little, and then slowly slid it even a little deeper. As I kept repeating this, I was imagining Natasha had far superior skills and could easily take a cock deep in her throat, so I just decided to go for it.

I took a deep breath, imagined that I looked the guy in the eye, and then rammed my mouth all the way down on that cock, and felt it slide down into my throat. It was only there for a second or two when I pulled back gagging and coughing. I was thinking to myself, "Gee, that wasn't very ladylike," (the gagging and coughing), but when I looked at the dildo, I could clearly see my lipstick at the very base of that cock...I took the whole thing!

Feeling satisfied that was the best I could do, I went ahead and started cleaning everything up, taking everything off, and putting everything away. After triple checking that everything was where it belonged, I locked up and headed home. Replaying everything in my mind about how awesome everything felt, I gave myself another thunderous orgasm, and then got ready for bed. That's when it happened...

My phone alerted me that I had an email so I checked it real quick...it was from Natasha. The email said, "I know your naughty little secret, princess, and I have video proof. You have no idea how mad I am right now! You have some decisions to make tomorrow; don't even think about being late for work! N."

"Oh, crap!!!!!" I thought, "I can't believe I was stupid enough to get caught." I immediately got very concerned about what was I going to do. I had no doubt that she was going to fire me for sure, even though I only had about a month left on my internship and I really need to complete it for my degree.

So many thoughts were going through my mind, such as, "I'm so friggin' screwed!!!" and, "What decisions was she talking about?" With my mind going a mile a minute, I obviously got very little sleep that night.

I got to the office early and waited anxiously for Natasha. When she got there, she wasn't her normal friendly self by any means. As she walked past my desk, all she said was, "STEPHEN...MY OFFICE...NOW!" Wow, she was pissed, and I just knew I was going to be fired.

She told me, "Shut the door, and sit down!" She had a tone in her voice that I'd never heard before. Stupidly, I tried to say something, but before I even got the first syllable out, she said, "You'll speak when I tell you to speak! I just can't believe what you've been doing. First off, you know that every time you use your scan card to lock and unlock the doors, I get a notification. When I saw that you've been coming back to the office in the evenings, I thought it was just to do work, so I didn't think a lot of it. Then last night when I saw that you scanned in, I went and checked the surveillance cameras just to make sure everything was ok, and imagine my surprise when I saw what you were up to!

I didn't know if I should be embarrassed, or scared, then she continued, "I just can't believe that after 11 months of working together, you had the gall to disrespect me like that and get into my personal things. Wearing my lingerie, and my best skirt and blouse, then prancing around here like you own the place! THEN...you use my lipstick...do you have any idea what an invasion on my personal privacy that is?

I knew better than to answer, so she continued, "Then to top it all off, I see you work over that dildo like you're some slutty little office girl. I just can't friggin' believe it!"

There was a long silence while we just stared at each other, and that was just killing me, but no way was I going to talk first. Then Natasha said, "My first inclination was to come right out and fire your ass, and to be completely honest, I still kind of want to. The thing is, we've done a lot of work over the past 11 months that I really don't want to just throw all that away, plus I know that you very much need to complete this internship to graduate, so the way I see it, I've got some pretty good leverage right now. I'm not usually a vindictive person, but I really feel like you should feel some consequences for what you did, don't you agree?"

I responded with a very meek and humble, "Yes Natasha."

She replied, "Good, I'm glad you feel that way."

She pulled a compact disc out of her briefcase and said, "Keep in mind, I have video of absolutely everything you did. So, here's my proposal, I won't fire you, but you can quit on your own accord, or you can finish the internship, but you have to do it strictly under conditions that I set. You have to decide right now, so what's it going to be?"

Sensing that it was now my turn to talk, and hearing that I can finish the internship, even though 15 minutes ago I was sure that I was completely screwed, I told Natasha, "I absolutely want to continue the internship." I really felt horrible that I hurt her so deeply, and I wanted to make up for that, so told her "I promise you that I'll abide by all your rules from here on out, no questions asked." That brought a hint of that familiar smile back to her pretty face, and I knew...or at least I thought I knew I made the right decision.

Natasha then took a letter out of her briefcase and made me sign it. The letter stated that I would continue the internship under strict conditions set forth by her, and that if I complete it to her satisfaction, she would destroy the video. If I violate any of the conditions she sets, Natasha is free to do whatever she wishes with the video.

Natasha then tells me, "Ok, so here's the deal, since you seem to like getting all dressed up in girly things, you're going to finish the next four weeks working here as Stephanie, not as Stephen. Stephanie will have all the same duties that Stephen had, but there will be some additional tasks, or should I say "jobs", on top of her regular duties." Natasha just looked at me with a devilish grin while holding up the contract I just signed.

I just sat there stunned....I didn't see this coming at all!!! Then she said, "Don't worry sweetie, based on what I saw on the video, you're going to do just fine...heck, you may even learn to enjoy it. Now for starters, get those gross boy clothes off and throw them in the trash can."

I tentatively started undressing, but Natasha hollered, "Come on, hurry up, we have work to get done today! Go ahead and get yourself dressed in all the same things you were wearing last night, and you can keep them because I don't want them anymore. Once you're dressed, sit you cute little ass at my desk and get those reports written. I'm going out to get a few things; I'll be back after lunch." Then she looked me square in the eye and said sternly, "Do...not...disappoint me," and then she left.

I quickly went to the closet and put on everything I wore the night before, then went back to the desk and sat down and started writing the reports. Wearing all that silk and lace felt so nice, but I didn't dare dwell on it too long...Natasha clearly meant business! I went to grab a highlighter from her desk drawer and saw the lipstick from last night and had a moment of panic, so I quickly put it on, for fear of Natasha catching me without it.

Natasha got back to the office just after lunch carrying several shopping bags. As she shut the office door, she said, "Alright miss Stephanie, it's time we get you dressed in clothes that actually fit you. Take all those clothes off, we're starting from scratch."

First thing, she had me put on a fresh pair of pretty lacy panties and a matching bra. The bra was lightly padded, but Natasha then slipped in breast forms to fill the cups out perfectly. Next she pulled out a pale pink corset and wrapped it around me. She pulled and tied the laces repeatedly until my waist was drawn in several inches. It was a little difficult to breath at first, but I eventually got used to it. Next she had my roll on a new pair of silk thigh-high stockings, then had me put on a new black pencil skirt that came down to about mid-thigh and made my butt look fantastic! Next came a white satin and lace camisole followed by a white silk blouse.

Once dressed, she went to work on my makeup, explaining what she was doing as she went. She told me that I would have to practice putting on my makeup several times every night in order to get the hang of it. After makeup, she grabbed the last two bags. The first one had a classic single-strand pearl necklace, matching bracelet, and a beautiful auburn wig. After putting on the jewelry and wig, the last bag had a pair of black 4 inch stiletto pumps.

After slipping on the pumps, she had me walk around the office. She gave me tips on posture and walking in heels, and I have to admit, I was feeling incredibly sexy, and I was dying to see what I looked like. When I finally looked in the full length mirror, I was in complete awe. My only thought was, "Stephanie is friggin hot!!!!!!!" I turned to Natasha, and I kind of wanted to ask her, "Are you serious about this?" but I saw the contract and CD lying on the desk, so I didn't say a word. Natasha told me to continue to walk around her office for a while to get more used to walking in heels, while giving me tips on how to properly sway my hips and look more feminine.

She took a few photos of me, then said, "I'll choose a picture for Stephanie's new company ID and scan card, because Stephan's has already been deactivated since he doesn't work here anymore."

"Holy cow, this is happening for real!" I thought to myself, "How in the world did I allow myself to get in this predicament?" My stomach was churning, and my head was spinning.

As I was working on my walk and feminine poise, Natasha lectured me, "For a girl to be successful in this business, she has to always be professional and confident with just a hint of sexiness, and her femininity has to be displayed in everything she does." Clearly that was exactly what she expected of Stephanie.

After 30 minutes of walking around the office, working on feminine posture and attitude, Natasha told me that I had an appointment to get my nails done at 4:30, which gave us about an hour to get some work done, and then she looked at me and said, "Oh, that just won't do!"

I looked in the mirror and immediately knew what she was referring to. The front of my skirt showed my obvious excitement, and she said, "That needs to be fixed right now." She had me sit up on her desk, turn so that my feet were near one side, then lay back. She shimmied my skirt up till she had free access to my throbbing cock sticking out the top of my panties. Without saying a word, she leaned in and took my cock in her mouth. It felt incredible and looked spectacular! Her pretty lips were wrapped expertly around my cock, and she was as good at sucking cock as I thought she would be!