tagTransgender & CrossdressersCaught with Consequences Ch. 02

Caught with Consequences Ch. 02


I woke up before my alarm the next morning. As I lay in bed, I couldn't stop thinking about everything that happened yesterday. It was weird; just being out in public and at the office as Stephanie was both terrifying and exciting at the same time. The mere thought that any of my friends might find out my predicament just turned my stomach in knots. I would be humiliated beyond any anything I could imagine. Then again, there's the challenge of being Stephanie...the challenge of trying to be flawlessly feminine at all times, and not letting any of my male mannerisms show. The challenge of emulating Natasha, and making Stephanie a confident, professional and attractive business woman that makes me feel so sexy.

I've admired Natasha since day one, but I guess I never realized how much I wanted to be like her. Certainly, she's been my mentor from strictly a business perspective, but now it feels like there's more than that. I've gotten a taste of what she has, how her being sexy equals having power, and how having power makes her sexy. It's intoxicating, and I have to have more, so I jump out of bed and begin to get ready for work.

After a shower, I begin to get ready. It still takes me close to an hour just to do my make-up, because I want to be sure I do it just as Natasha showed me. After make-up, I put on a fresh pair of pale pink panties with a matching bra. Next I slip into a new pair of lace top stockings. Wow, they feel so incredible sliding up my freshly shaven legs! My ribs are a little tender from two solid days of being tightly laced into my corset, but it's essential, so I lace it as tight as possible while I watch my feminine form take shape. I then put on a new skirt and blouse that I bought last night, and slip into my pumps. After putting on my wig and combing it out, I put on my pearls, and then headed to the kitchen for breakfast. After a quick snack, I put my lipstick, mascara, and a compact in my purse, and I was ready.

Just getting in and out of a car with a skirt and heels on without flashing my panties to everyone was still challenging, so I tried to make sure no one was looking as I got in and out of my car. I'll have to work on that some more!

I got to work at my normal time, and as I sat at my desk, it seemed like I was seeing more people than usual in the hallways in our part of the building. I was getting a little paranoid that people knew about me, though no one actually stopped into our office or said anything to me. I was sitting at my desk working when Natasha got to work.

As she walked by she smiled at me and said, "Well good morning Stephanie! And how are you feeling this fine day?" in a very upbeat and sing-song tone.

"Great!" I said, while trying to match her tone, "And how are you?"

"I'm wonderful," she replied, and then she walked into her office.

That pleasant exchange put me at ease a little, so I just kept working on the project files on my desk. All morning long, it was business as usual. We discussed various projects and reports, planned out some presentations for next week, and worked on a proposal and bid for a brand new project. I was really expecting Natasha to ask me about how things were going as Stephanie, or talk about the contract, or something...anything. I was dying to talk about it, but I was getting the feeling I wasn't to bring it up, so I didn't. By not getting to talk about it, it was like Stephen never existed, and Stephanie had been there for the past 11 months.

Later that morning Natasha came to my desk and said, "A couple of the girls and I are going out for lunch, would you like to join us?"

Natasha had invited me to lunch before, but it was always just she and I, never with a group. Since I had forgotten to make my lunch that morning, I said "Sure, I'd love to!"

She said, "Great, grab your purse, and let's go!"

Since the restaurant was only two blocks away, we decided to walk as it was a nice sunny day. It was the farthest I'd ever walked in heels at one time, and I loved the sound of both of our heels clicking along on the sidewalk. Just before we walked in, Natasha turned to me and said, "Now Stephanie, you had better be 100% on your game, or these girls will figure you out in a heartbeat!" Before I could respond, we walked inside.

It was a pretty nice restaurant, about half filled with well-dressed business men and women. It was certainly not a place I would normally go, but yet, here I am! The hostess brought Natasha and I to a table where her two friends were already seated. As we all greeted each other, Natasha said, "Stephanie, this is Anastasia, and Rebecca."

If I had to guess, I'd say Anastasia was in her late 30's, probably about 5'7, curvy, and beautiful! Her hair was the most golden blond you could imagine, and she had it pulled up into a sexy bun. She owned an accounting firm that we sometimes did business with.

Rebecca was probably in her mid 20's. She was a bit taller than Anastasia, and absolutely stunning! Her skin was tanned and flawless, and she had beautiful, thick, auburn hair pulled back into a ponytail that hung down to the middle of her back. She wore a very snug skirt that showed off her firm ass and toned legs, and a sleeveless silk blouse showing just enough cleavage to almost make me drool! She worked as a CPA at Anastasia's firm.

We all exchanged pleasantries and sat down, and I kept thinking about what Natasha said, which made me super nervous. I tried to just keep quiet in fear of outing myself, while they all chatted. After a while, Natasha started to pull me into the conversations. She knew good and well that I was scared to death, yet she was forcing me to join in the "girl talk".

When the other two weren't looking, she flashed me half a wink and a sly smile, which told me that she was doing this on purpose! She was enjoying watching me squirm, and I knew right then, that was her plan. She intentionally kept it up, making me talk about my favorite shoe stores, what kind of purses I like, where I get my nails done, etc. etc. I mostly tried to just agree with whatever was being said, but Natasha kept putting me on the spot. I was starting to get the hang of girl talk, but then the subjects of men and sex came up. Fortunately, that's right when our food came, so I was able to mostly stay out of that conversation, but not entirely.

Natasha came right out and asked me, "So Stephanie, you must do pretty well with the guys, when's the last time you got your pretty little hands on a nice hard dick?"

I about choked on my sandwich right then and there, but I tried to play it cool and said, "Oh, it's been a little while, probably a couple weeks ago." This was obviously a lie, because just yesterday I sucked 4 different cocks, swallowed 5 loads of cum, plus I got fucked doggie style...hard! Natasha knew good and well what I did yesterday, she just wanted to make me squirm some more, and she did a great job of that!

We all finished up our meals and were waiting for the check, when the other three ladies all took small mirrors out of their purses to check their lipstick, and I thought, "Finally, something I can do to fit in with these girls." I took my compact out, opened the mirror, and then touched up my lipstick also.

Just as I finished, Natasha said, "Stephanie, that's a great color on you. Did you just start wearing that shade recently?"

I looked at her and she gave me that smile and wink again. She sure seemed to be having fun toying with me! Considering that until two days ago, I was all dude, and had never worn lipstick in my life, what else could I say?

"Yeah, I just got this the other day. I'm glad you like it, a really hot chick that I know recommended it for me."

Natasha and Anastasia split the check, and we got ready to leave. We all gave each other a little hug, and then we headed out the door. Natasha and I headed down the street towards our office, and Anastasia and Rebecca headed the other direction. We hadn't walked very far when Natasha said, "You did a pretty good job in there Stephanie, very believable. Did you enjoy yourself?"

I told her, "Oh my God, I was soooo nervous! That was the most stressful thing I've had to do since I became Stephanie!"

Natasha said nonchalantly, "That was the most stressful? Hmm, interesting. Well I hope for your sake you can keep it up!" The rest of the walk was in silence, except for our heels clicking along on the sidewalk. I really do like that sound, so I just relaxed and enjoyed it.

Back at the office, we got right back to work. Again, I was expecting Natasha to ask me more about how I was getting along as Stephanie, but she didn't say a word about it, we just focused on work. Just like this morning, I was noticing more people than normal in the hallways on our end of the building. I tried to tell myself I was just being paranoid, but I just couldn't help wondering if Natasha said something or if the word got out some other way.

About 3:00, I got an email from someone I didn't recognize, turns out it was from Rebecca. She asked me if I wanted to go get lunch with her tomorrow, and I told her that sounded great. She said she would swing by my office and pick me up about noon.

A few minutes later, Natasha walked by my desk and said, "I'll be gone for the rest of the day, I trust that you can take care of things around here?"

"Of course, no problem at all!" I said. Just before she waked out the door, she looked back at me over her shoulder and gave me her sexy little grin, and then she left. I didn't really think a lot about it, and I got back to work.

About 4:00, a guy came in. He introduced himself as Robert, said he worked for Bear Engineering, and that he had a couple change orders for the project we're working on. I stood up, and cheerfully said, Well of course! Follow me, and we'll take a look," and we headed into Natasha's office. He gave me the project ID, and I went over to the files to pull the plan set. Knowing he was watching me, I was sure to add a little extra wiggle to my strut. As I pulled the plan set, I realized it was the same project that I reviewed with Paul and Brad the other day. I spread the files out on the drafting table, and Robert started to explain the change orders. They were really simple changes that he easily could have just emailed to me, but we went over them anyways.

It only took about 15 minutes to finish them up, and then I gathered the files and took them back to the cabinet. As I was filing them, Robert said, "So, I was talking with a couple of my colleagues about this project, I think you may have met them...Brad, and Paul?"

I was putting the files in the bottom cabinet, so I was bent over at the waist, with my ass pointed towards Robert. I looked back at him and said, "Oh, yeah, I think they were here a while back." I closed the cabinet, stood back up and turned towards Robert.

He had just closed the door when he said, "Oh, I'm sure you remember them. If not, I've got a couple videos here that Brad sent me that may trigger your memory."

Knowing good and well that those videos are of me on my knees with Brad's and Paul's throbbing cocks in my mouth, I said, "Yeah, I remember."

"Good," Robert said, "Paul said that I really needed to come by and see you. He guaranteed I wouldn't be disappointed."

I thought to myself, "Well Steph, looks like it's time for another blow job," so I walked over to him as he leaned up against the table. I sunk to my knees and started undoing his belt. I quickly had his pants and boxers around his ankles and his stiffening cock in my hand. He stepped out of his pants and boxers and kicked them aside as I began to playfully lick up and down his entire shaft. I was ready to suck his impressive thick cock and swallow his load, but he stopped me.

He had me stand up, and then turn and faced the table. His hands worked up under the front of my skirt and he pulled my own throbbing cock from my pretty panties. As he gently began stroking me, he was hugging me from behind and I could feel his warm cock pressing against my now bare butt cheeks. He held me in this position while he expertly stroked my rigid cock...it felt incredible! Every once and a while he would nibble on my neck or ear as he worked me into a frenzy.

This was escalating quickly! My breathing grew fast and shallow, and my knees grew weak, and I could feel it welling up from deep inside me! In no time at all, wave after wave of creamy cum poured from my cock, and Robert caught every drop of it in his other hand. He gently milked me with his expert touch until he was holding my entire load in his hand. He said, "Oh yeah, that's going to work perfectly."

I wasn't sure what that meant. He let go of my shriveling cock, and gently pushed me up against the wall so I was facing away from him. He told me to spread my legs, and as I did, I felt my own warm cum being spread over my asshole. As he massaged it in, he worked his now slimy finger up inside me. His hands were huge, and it felt like he had just buried a small cock in my ass. He could feel my obvious tension, so he kept telling me to relax as he soon added a second finger.

As I leaned my face and forearms against the wall, I pushed my ass out towards Robert to give him better access. Robert then smeared the rest of my cum all over his cock, and I felt him move into position. The spongy head of his throbbing meat was pressing against me, and he just held it there. He put his hand to my lips and told me to clean the last couple drops of my cum off his fingers. I greedily licked his hand all over, the sucked each of his fingers to be sure I didn't miss any.

I then felt both his hands on my hips, and he said, "You want this don't you? Brad told me how much you liked it, how you begged him to fuck you like the slutty little bitch you are. Tell me how much you want this!"

This was all getting me very, very worked up, so I looked back at him over my shoulder and begged him, "Please bury your hot throbbing cock inside me! I'm just a naughty little bitch who just can't get enough cock. I'm a cum hungry little slut, and I want you to ravage me with huge throbbing cock! I'M BEGGING YOU...PLEASE FUCK ME...FUCK ME HARD...PLEASE FUCK ME NOW!"

He pulled me back against him and I felt his cock slowly invade my ass. His giant cock was stretching me so wide, and it hurt so bad, but I kept asking for more. Slowly he worked his girthy cock in and out of my willing ass, stretching me wider and wider each time, until with one powerful stoke, I felt his pelvis slam into my ass. I had the whole thing inside me now, and it was massive!!!!! I let out a girly squeal each time he buried that cock in my ass. Over and over I felt his throbbing meat deep inside me, and the feeling was incredible! I never wanted this to stop! In between his grunts, Robert was saying, "Take it you little bitch! Take that cock you little fucking slut!"

I felt him gripping my hips tighter and tighter, and the pace of his cock plowing into my ass quickened. His breathing was getting heavier, as he continued his unbelievable assault on my ass. After almost 10 minutes I could hardly even stand up on my own, but he held me up by my hips as he mercilessly pounded my poor ass. His pace began to slow down, but the force of his cock burying itself inside me increased. Over the next 30 seconds, he was absolutely impaling me with his cock, and then he pulled me hard into him and held me there as I felt his cock explode, filling me with his hot cum. He held his cock buried to the hilt in my sweet, but abused ass, and I could feel every rippling spasm as he poured wave after wave inside me. After the spasming slowed, I gripped his cock with my ass to try and milk every last drop from his softening cock. I could feel his hot sticky cum beginning to leak from my ass and ooze down the insides of my thighs.

He slowly slipped out of my well fucked ass, and as soon as he did, a flood of his hot gooey cum leaked from my now gaping hole and dribbled down my inner thighs and slimed my stockings. I even noticed a couple pearly drops of cum on the toe of one of my patent leather pumps. Robert wasted no time getting himself dressed, and headed towards the door, leaving me weak in the knees and still leaning against the wall. I was such a hot slutty mess!

Robert said, "You know what? Brad was right, you absolutely did not disappoint, that was fucking awesome!!!" and with that he walked out the door.

As I straightened up and walked to the chair to sit down, every step I took caused a little more of his cum to leak from my ass. I picked up my panties and put them back on, and between the cum on my thighs and the rest leaking from poor punished ass, my panties were soon a creamy, gooey mess plastered to my ass, cock and balls. It took me almost an hour to get cleaned up so I looked presentable enough to head out of the office and to my car. All the way home, I thought about what the dry cleaners must think of me, since every couple days I bring them one of my skirts covered with cum. I suppose they think I'm just a slutty little cum toy. Sounds about right, today anyways!

The next morning at work, again, everything was all business, though my sweet little ass was still a little tender from the pounding it took yesterday. I was getting more comfortable, and even chatted up a few folks in the hallway. Everything seemed fine, and no one seemed suspicious at all. What a relief!

Just before noon, Rebecca walked in, and she looked just as hot as she did yesterday! She flashed the most beautiful smile and said, "Hey, ya ready to go?"

I said "Sure am!" and I grabbed my purse and we headed out.

Rebecca drove us to a sandwich shop across town. As we chatted along the way, she apologized that we couldn't talk more yesterday. Rebecca explained that Anastasia tends to be the chatty one whenever they go out, so she just tends to just sit back and take it all in. I told her, "Yeah, I get that, I'm kind of the same way."

After we got our food and we sat down, Rebecca said, "So Steff, tell me about yourself."

That kind of caught me off guard at first, mostly because for obvious reasons, I absolutely didn't want to tell her anything about the real me! I finally responded, "Eh, there's not a lot to tell. I'm a grad student, just finishing up my internship before I go out and make the big bucks!"

We both kind of chuckled, and then spent the rest of lunch chatting. As we sat there chatting I just couldn't take my eyes off of her. She was just so beautiful, and charming, and friendly. Her eyes were the brightest blue I'd ever seen, and I was just lost in them. I was really digging this girl, but unfortunately, in my current situation, there wasn't anything I could do about that.

While we chatting, she mentioned lunch yesterday. She said, "So, you mentioned at lunch yesterday that it's been a while since you've been with a guy. I can't believe a hottie like you isn't dating someone."

I tried to play it off saying, "Yeah, I guess I just haven't found the right one yet, but it's not for lack of trying!"

We both giggled, and she said, "Yeah, I hear ya. I'm in the same boat."

In my mind I was thinking, "Ha! Girl, if you only knew..."

Once we finished lunch, we headed back so she could drop me off at my office. When we got there, I leaned over and gave her a girl hug and said, "Thanks Rebecca, this was fun. Next time lunch is on me."

She said, "Oh, please, call me Becca...and that sounds great, how about tomorrow?"

I said, "Awesome, see ya tomorrow!"

After I got out of her car and she drove away, I could still smell her perfume. This woman was incredible, and I couldn't do anything about it but be her friend.

The rest of that afternoon, and the whole next morning, I couldn't stop daydreaming about Becca. I couldn't wait to see her again, and time just seemed to drag on, as it usually does when you're really looking forward to something. Once lunchtime finally got there, I rushed over to pick Becca up, and we had another fun chatty lunch together. Dang I was falling for her, but I couldn't do anything about it!

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bySteffinheels© 3 comments/ 18855 views/ 30 favorites

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