Caught with Consequences Ch. 03

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Stephanie's sexy (and naughty) adventures continue!
5.7k words
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Part 3 of the 4 part series

Updated 06/08/2023
Created 04/05/2018
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On Monday morning, I had on a new silk dress that made me feel very pretty. I loved the way the skirt flowed and billowed as I walked...so much so, that I parked way at the other end of the parking lot, just so I was able to walk as far as possible. There was a slight breeze, and the feel of the cool morning air wafting under my dress and caressing my thighs and ass felt wonderfully sexy!

I had only been at work about 45 minutes when Natasha called me into her office. She complemented me on my dress, and then asked me to sit down as she wanted to discuss a few things. She asked, "So Stephanie, how have things been going?"

I said, "Pretty well. I finished the data collection for the..." and Natasha cut me off.

"No," she said, "That's not what I mean. I mean, how are things going as Stephanie?"

"Oh," I said. "Well, I OK guess. I'm still really nervous going out in public where I have to interact with people. I'm afraid they'll figure out I'm a guy dressed as a girl, and just the thought of how humiliating that would be is terrifying. That being said and I know this sounds weird, that's also really exciting!"

Natasha said, "Yeah, I understand that I suppose, and since you brought it up, Stephanie the intern is doing a good job, just as Stephen the intern did...but that's not really what I want to discuss. Stephanie the slutty intern seems to be doing a great job!"

I responded with a quizzical look saying, "I'm not sure I follow."

She said, "Stephen worked here for 11 months, and not once did he bring in a new client or account. Stephanie has been here for a week and a half, and suddenly we have 2 new clients, and 3 new projects from Bear Engineering. I don't think that's a coincidence. I think Stephanie has gone above and beyond in her efforts to make our clients happy...know what I mean?"

I said, "Well, you told me that Stephanie would have some additional jobs to do that Stephen didn't have. I figured that meant that I had to do anything anyone asked. Heck, the very first day you sent me over to Mr. Kelly's office. When he was sitting there in his boxers with a hard on, what was I supposed to do?"

"True," Natasha said, "I did send you over there, but I certainly didn't tell you to suck his cock."

"You mean I could have said NO?"

"Of course you could have, and he would have been fine with that, but you didn't, in fact you didn't say anything at all did you? You just sunk to your knees, wrapped your pretty lips around his cock and sucked him off. Sounds to me like you swallowing his load of cum was as much your idea as it was his."

I just sat there stunned; I had no idea what to say! Natasha continued, "Stephanie the intern was my idea, you're the one who turned her into Stephanie the office slut, and believe me, there's no going back!! Don't worry, this doesn't change our deal, but now that I know about this whole other side of Stephanie, I think I'll have a little fun with it!"

I didn't get a good feeling about that at all, but I was really stuck between a rock and a hard place. I signed a contract that said I would abide by all her rules for the rest of the internship, no questions asked. I was just going to have to play along.

Natasha could see I was worried, so she said, "Seriously sweetie, don't worry, I think it's going to be fun! Now, let's get back to business. We have a teleconference for the final meeting on that big Bear project this afternoon. Since you've done a lot of the work, I'll do the opening comments and overview, and then I'll have you do the final review and approval of the specs. The teleconference starts at 1:00, so be prepared."

At 12:55, I went into her office and put all the files on Natasha's desk; I was ready to go. Natasha was already setting up the call, and had even poured me a fresh cup of coffee. We were sitting side by side at her desk and as Natasha was dialing into the call, she looked at me with one of her sly, sexy grins and said, "Are you ready for this?" I gave her a confident nod.

As all the participants were introducing themselves on the call, Natasha held a note card in front of me that just said "KNEEL IN FRONT OF ME, NOW!" I looked at her and mouthed the word "WHAT?" She looked at me very sternly and pointed at the floor in front of her. I slid out of my chair and knelt in front of her as ordered. She held another card in front of me that said "SUCK MY COCK BITCH!" As I read it, she slid up the hem of her skirt to reveal a strap-on dildo.

Now I understood what she meant when she said she was going to have some fun with Stephanie the Slut. I leaned in and started licking the dildo, soon taking the head into my mouth. I heard someone on the call ask where Stephanie was, and Natasha said, "Oh, she's a little busy right now, but she'll be here soon."

As Natasha began her briefing, she grabbed me by both sides of my face and pulled me down on the dildo, driving it deep into my mouth. She kept doing this over and over and over, the whole time she was talking. For 10 minutes straight, that cock was like a piston pumping in and out of my mouth, occasionally going down my throat. I was concerned the loud slurping could be heard on the phone, but there was nothing I could do, she was in charge. As she finished her comments, she pulled me off that cock and motioned for me to sit in my chair, then handed me a card saying, "Fix your lipstick."

After I touched up my lipstick, we were listening to the guys from Bear Engineering talk about the project when Natasha handed me the next card that said "STAND UP AND FACE THE DESK." I did as I was told, then the next card said "BEND OVER THE DESK, REST YOUSELF ON YOUR FOREARMS". As soon as I did that, Natasha started gently brushing her hands up and down my stocking clad legs. Oh my God, that felt so awesome! Then she started lightly dragging her perfectly manicured nails slowly up my legs. It felt absolutely amazing!! She worked her way up the back and insides of my thighs, past the tops of my stockings and over the lacy edges of my panties. She had me so turned on, I hadn't even realized that it was my turn to talk on the call.

I tried to collect myself and started giving my presentation, while Natasha continued her erotic and sensual assault on me. Somehow I muddled my way through the rest of my info, and then as the financial folks started their presentation, Natasha put the phone on mute and told me to slip off my panties. As soon as I did, she pushed me back down on my forearms, and then moved in behind me. She hiked up my skirt and soon I felt the coolness of lube smeared onto my rosebud, followed by the head of her dildo pressing against my ass.

Natasha said, "OK, here we go!" and then she unmuted the phone. She grabbed me by my hips and I felt the dildo press harder and harder until the head slipped inside me. I let out a muffled squeal, though I don't think anyone heard it. She slowly kept pushing into me, and I felt every inch invade my sweet ass until I felt Natasha's pelvis pressing against my cheeks. She then slowly pulled back until just the head was barely inside me, and then started over. Natasha worked that cock in and out of me at a steady pace for the next 5 minutes, and I laid there taking (and enjoying) it like the slut I've apparently become. She was picking up the pace, fucking me even harder when I heard someone say my name on the teleconference.

I tried to compose myself and asked, "Could you repeat that please?" It was Robert asking if I had any final comments about the specs of the project. Natasha was burying that cock in my ass with force as I said breathlessly, "No, I'm good to go. Everything looks great from here."

Natasha put the phone on mute again, and then told me to stand up. She reached around and grabbed my cock and started stroking it in the same rhythm as she was plowing my ass. In less than a minute, I was getting close to cumming, so Natasha slid my coffee cup under my cock, just as I unloaded a huge load of warm creamy cum directly into my coffee. As she milked the last drops from my still throbbing cock, she slipped the dildo out of my ass. I put my panties back on, and we both sat down in our chairs to finish the call.

As the call was wrapping up, Natasha handed me another card that said "DRINK YOUR COFFEE". As I took a little sip, I could definitely taste the cum. After we all signed off the call, Natasha said, "How do you like your coffee?"

I tried to make light of the situation, so I said, "I don't mind a little cream in my coffee," and then took a nice big swallow to prove it.

Natasha said, "Good, I'm glad to hear that, because throughout the morning, I managed to get 3 guys to jerk off and dump their loads into your cup. There's as much cum as there is coffee in there, and you're going to finish the whole thing!"

Over the next 15 minutes, I sipped on it, and it seemed like the taste of cum got stronger and stronger. As it turned out, most of the cum was settled to the bottom, so the last couple swallows were just mouths full of warm creamy cum with a hint of coffee. As the last gooey glob slid down my throat, Natasha said "Good girl, now back to work!"

Just before we went home for the day, Natasha came to my desk and said, "Stephanie, I'm going to be having a little party at my place tomorrow evening, and I'd really like it if you could come. It's just me and a few other girls...a little dinner...a little wine, it'll be fun."

I didn't have anything planned, and sensing I really didn't have a choice anyways, I said, "Sure, what time?"

"Great! About 7:00," she said, and then she headed out the door.

The next day at work, everything was business as usual; at least it was between Natasha and me. There were a couple guys from other offices that suddenly wanted to chat me up. I'd seen them around the building for months, but never really said anything to them at all, but for some reason, now they were super chatty. It took me a while, but I finally figured that maybe these were a couple of the guys that put a deposit in my coffee cup yesterday. I have no idea how Natasha managed to talk them into that, or what she told them about me. Even though I'm just now meeting them for the first time, I'm guessing I've already swallowed a load of their cum. I know I was thinking about that the whole time we talked, and I wondered if they thought the same.

I rushed home from work in order to get ready for Natasha's party. I put on a cute dress and did my make a little more boldly than I did for work. I put on dangly earrings and a matching silver necklace, slipped on a pair of sparkly heels and headed out the door. I was in the mood for some good food and good wine, so I decided to Uber instead of drive my own car.

I got to Natasha's just after 7:00. As I walked up the driveway, she opened the door and said, "I'm so glad you came, come on in!" Just as we were walking into the living room, Natasha said, "This is going to be so much fun, I've already told the girls all about you."

I stopped in my tracks as my stomach did about 4 back flips! "You told them?"

"Don't worry silly, I didn't tell them everything."

I cautiously followed Natasha into the living room where the other 4 ladies were sitting, drinking wine. I tried to prepare for the worst. Natasha then introduced me, "Hey girls, Stephanie's here!"

They all introduced themselves, and they were all really friendly. No one said anything indicating that they knew I was really a guy, so I was wondering what Natasha really told them. One of the girls spoke up and said, "Natasha, I thought you had a boy intern working for you."

Everyone looked at me, and I thought to myself," Oh crap, here we go..."

Natasha then said, 'Oh, that was Stephen. Yeah, he and I ran into a bit of a glitch, and he just didn't work out. That's when I hired sweet little Stephanie here. She's doing a fantastic job...but enough shop talk, let's eat."

We all went into the kitchen where Natasha had a taco bar set up, and plenty more wine. While we were eating, Christi said to Natasha, "It's too bad you had to let Stephen go, I was hoping to get a piece of that someday!" All the girls giggled as Christy continued about all the hot kinky things she wanted to do to Stephen. The others started chiming in about how they had also wanted to ravage Stephen, how they wanted to just throw him down on his desk and ride his face, suck his cock, and bite his sweet ass. It was so wild listening to what all these hot women were saying about what they wanted to do to me, and it was really turning me on!

When we were done eating, Natasha asked me to help put away the food as she told the others to head back to the living room. When the kitchen was clean and we started back to the living room Natasha said, "So Stephanie, did I happen to mention that this is a sex toy party?"

"What?" I said as I stopped in my tracks, "What do you mean it's a sex toy party?"

"I mean, it's like a Tupperware party, only for sex toys. I throw a party every few months, it's a fun way for the girls to all get together and just let their hair down a little...come on, live a little!" She didn't give me time to think about it, she just held my hand and led me into the living room.

There were a couple tables set up with an assortment of toys arranged on them. There were dildos, vibrators, lubes and lotions, handcuffs, nipple clamps, penis shaped lipsticks etc. etc. etc. I was pretty embarrassed just looking at all this stuff, especially in a room full of hot women. I must have been blushing, because Christi said, "Stephanie, this stuff doesn't embarrass you does it? You seem like a girl who likes to have some naughty fun!"

Anastasia jumped in and said, "Of course she likes to have fun! I'll bet you had fun when you were getting double-teamed by those two studs in Natasha's office didn't you Steff?!"

The room went quiet and my face probably turned four shades of red. I looked at Natasha and said, "Oh my God, you knew about that??"

She replied, "Oh sweetie, it's my office, I know everything that happens in there!" then the rest of the girls all giggled and started telling me how lucky I was. They all joked about how they now wanted to work for Natasha too! While I was still super embarrassed, I did feel a little better now.

Natasha handed us all a catalog of all the products that she was selling, and then asked me if I would help her show some of the demo models. As she talked about an item, I had to retrieve it from the table, and then walk around to show it all the girls, who were sitting around the room. I was doing my best to be Natasha's sexy assistant, showing off everything from the cute little finger sized vibrators, to some ridiculously big, but lifelike dildos. Holding those massive cocks in my hands, showing them to these smoking hot women, and hearing their comments about what they thought of these toys was just unreal!

After showing off all the toys, Natasha needed two volunteers to play a game. Actually, she only needed one volunteer, because she told me I was playing. Christi jumped up and said that she wanted to play too. Having no idea where this was going, I got that knot in my stomach feeling again!

Natasha had Christi and I sit in chairs in the middle of the room, then she took two pairs of pink fuzzy handcuffs, and cuffed our wrists behind our backs. Next she got two tubes of the cock shaped lipsticks, held one in each hand and told us to choose. Christi ended up with one called "Cum Ravage Me Red", and mine was called "Cum Fuck Me Fuchsia". Natasha had two of the girls apply the lipstick to Christi and I, making sure it was put on very heavy.

At this point, Natasha announced that this was a blowjob contest, and that the winner of the contest would receive a free gift bag, to be selected by Natasha. The rules of the contest were that two girls would stand in front of Christi and I holding matching dildos in our faces. We had 60 seconds to give our best blowjobs, and we would be judged on technique, enthusiasm, and depth. All the girls were laughing it up and having fun picking their favorites as Christi and I sat there a little stunned. I looked over at Natasha, and she gave me a wink and a smile, showing that she was having a blast embarrassing me like this.

Next Natasha had Anastasia stand in front of me, and Susie stand in front of Christi, then handed them matching dildos. These things were HUGE! They were at least 8 inches long, and almost 2 inches in diameter. Anastasia and Susie held those cocks at crotch level, and then stood directly in front of us so the heads were right in front of our faces. Before I had a chance to protest that I didn't want to do this, Natasha, "OK bitches, get ready to suck those cocks! 3...2...1...GO!"

The girls were all cheering us on as Christi and I started sucking those giant cocks. Though it was bigger than any real cock I've sucked, I was quickly able to get the first third or so into my mouth. Having my hands tied behind my back, I had to rock my body back and forth in order to bob up and down on that cock. I started moaning as I did my best to take it deeper and deeper while gradually picking up the pace. Natasha announced that there was only 30 seconds left and the girls started cheering louder.

Anastasia started pumping her hips while cheering me on saying, "Come on Steff, suck my meaty cock! You know you can do it, take it deep bitch!!" and with that, I felt that giant cock start deep into my throat. Anastasia pushed as I felt it going deeper than I've ever had a cock in my throat before. Soon I felt the fabric of her dress brushing against my face, and then she backed that beast all the way out until just the head was in my mouth. When Natasha announced there were 15 seconds left, Anastasia and I locked eyes. She gave me a quick grin, and then proceeded to thrust that cock back into my throat. I took it like a good little slut without gagging, but my eyes were watering something fierce! As she was slowly pulling back, sliding it out of my throat again, Natasha yelled "TIMES UP!"

All the girls yelled and cheered as Christi and I sat there trying to catch our breath. Natasha uncuffed our wrists, then said "OK girls, let's check the scores. In the category of sexy enthusiasm, based on her sexy moans and impressive pace, the nod goes to...Stephanie! In the category of blow job technique, displaying superb cock sucking skills and wonderful eye contact throughout, the nod goes to...Christi!

All the girls cheered and were calling out their favorite to win when Natasha announced, "And for the final category, both girls left lipstick prints on their cocks, so let's measure. The Cum Ravage Me Red lip prints measure in at 5 ¾ inches...not bad! And for the Cum Fuck Me Fuchsia lip prints...all the way to the base, taking all 8 ¼ inches into her throat! That makes Stephanie our Cocksucking Champion!!!"

Everyone was laughing and having a good time, while I was quite embarrassed...I just won a cock sucking contest in front of a bunch of hot women!! Natasha handed me a large pink velvet drawstring bag with my prizes in it and made me open it in front of the girls. Inside was a dildo like the one I just got done deep throating, a new pair of fuzzy pink hand cuffs, three cock shaped tubes of Cum Fuck Me Fuchsia lipstick, a metal butt plug with a sparkly pink gemstone on the end, a small bottle of flavored lube, and a satin sash that said "Miss Deepthroat" in large glittery letters, which I was made to wear for the rest of the evening.

For the next hour or so, we all browsed through all the toys on the table as well as leafed through the catalog. After a while, Natasha handed us each an order form and all the girls immediately started filling them out. I didn't want to look out of place, so even though I already had a bag full of toys, I ordered a vibrator, some lube, and a pair of nipple clamps. I had no intention of using any of them, but I felt like I had to order something to be seen as "one of the girls".

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