tagTransgender & CrossdressersCaught with Consequences Ch. 04

Caught with Consequences Ch. 04


Chapter 4

The next morning after getting myself dolled up, I headed in to the office. As I logged on to my computer, I saw that Natasha sent me my first appointment. Apparently Anya was out again, so I was to report to Mr. Kelly's office at 8:30, and to text Natasha when I got done. The last time I saw Mr. Kelly, I had my pretty red lips wrapped around his cock as I gave my very first blowjob. Since it was already 8:15, I freshened up my lipstick, grabbed my purse and headed across the street to his office. Just like before, I felt like the sound of my heels echoing down the halls practically announced what I was coming to do. When I got to his office door, I stopped for a second, and then confidently walked in. I walked up to his desk and said, "Good morning Mr. Kelly, it's nice to see you again. Natasha said that Anya was out and asked that I come over and give you a hand."

"Well good morning Stephanie, don't you look stunning today! I'm so glad to see you; in fact I haven't stopped thinking about you since the last time you were here. Would you please be a dear and get me a cup of coffee?"

"Of course!"

As I strutted over to the coffee maker across the room and poured him a cup, he said, "Feel free to pour yourself a cup also. Natasha mentioned that you prefer quite a bit of cream in your coffee."

I looked back at him and said, "You knew about that?"

"Knew about it? I was the first contributor! Natasha told me what she had planned, and I came right over and jerked off in your cup. So tell me, how was it?"

I was unbelievably embarrassed, and said very sheepishly, "Well, it was definitely the gooiest cup of coffee I've ever had sir."

"MMMM, I bet you loved it! Now get your sweet little ass over here and get you some more!"

As I walked to his desk, he stood up and undid his pants, letting them drop to the floor. He kicked them aside, stripped off his boxers and sat back in his chair, with his hard cock pointing at the ceiling.

"Come on, let's get this going, I don't have all day. Get on your knees, wrap those pretty red lips around my cock so I can feed you another load of cum."

I thought to myself, "Well this is certainly different than the first time I sucked his cock, but I suppose this is how it's going to be," so I sunk to my knees grabbed his cock which already had a dollop of precum on the tip, and took it in my mouth. He immediately grabbed both sides of my head and started guiding my up and down his cock as he said, "Oh yeah, I'll bet you'd love to have a load of spunk in your coffee every morning now, wouldn't you? Or maybe I'll just have you come over here every morning and I can feed you a load straight from my throbbing cock. It's your choice honey."

He never let go of my head, and soon he was forcing me down so hard, his cock was slipping into my throat. Over and over I took it into my throat and as he was getting close to cumming, he started grunting, then buried his cock in my throat and held it there. I could feel his cum being pumped straight down my throat, and he held me there till 5 strong waves were deposited. Once he was done, he finally let me up, as I was gasping and coughing, Mr. Kelly just sat there, staring down at me past his half flaccid cock. He made me lick up the last few dribbles of cum off his cock, and then he got himself dressed.

I got up off the floor and straightened my blouse and skirt. Mr. Kelly walked over and gave me a firm slap on the ass, and told me, "Nice job there honey, thanks for coming by."

I grabbed my purse and walked out the door. I texted Natasha and told her I just left Mr. Kelly's office, and she texted right back telling me to go directly to Mr. Howard's office, which is on the other end of that same building. I started down the hallway towards Mr. Howard's office, hearing my heels echoing down the cavernous hallway. I do love the sound of heels on tiled floors. I got to his office, but I was feeling kind of nervous, so I took a second to relax before I went in. I rechecked my make-up, and then walked into his office. I didn't even get a chance to say hello, when he looked at me, kind of chuckled and said, "You must be the little slut from across the street who likes cum in her coffee, huh?"

Instantly humiliated, I simply replied, "I'm Stephanie, from Natasha Gold's office."

"Yeah, that's what I figured. Natasha told me she had a new office slut, and I thought it was hilarious when she told me she was going to make you drink coffee with a bunch of cum in it. So tell me, do you prefer your cum in coffee, or straight from the cock?"

I didn't get a chance to respond before he stripped off his pants and boxers then sat up on his desk, and said, "Darlin', I'll tell you what, why don't you just go ahead and start sucking my cock now." His desk was so tall I couldn't kneel down and still reach his cock, so I had to suck it by leaning over while standing up. His cock wasn't very big at all, so I could easily take it all in my mouth. As I was sucking him, he said, "Ed's gonna be down here in just a few minutes. He dropped a load of spunk in your cup the other day too, and he's looking forward to feeding you another one."

Just then I heard the door open and close behind me. Having a mouth full of cock, I couldn't look up to see, but I heard a booming voice behind me say, "This must be the little cum guzzler from across the street huh! Hurry up and finish him off sweetheart, then I'll let you suck a real man's cock!"

I wanted to get this over with as soon as possible, so I was really working Mr. Howard's cock, taking it all and slurping on every stroke, and he was really responding! He was moaning loud, and telling me "Yeah bitch, suck it. Suck my cock. Suck my cock and swallow my cum again bitch!" and suddenly he exploded in my mouth! Though he didn't have a big cock, he sprayed an impressive amount of cum across my tongue and down my throat! I kept his cock in my mouth until it stopped twitching, sucking up every last drop.

Finally letting his cock slip from my mouth, I stood up and turned around to see Ed sitting on the couch, with his swollen cock in his hand. Ed ordered me to kneel in front of him, and when I did, he grabbed me behind my neck and pulled me towards him till his cock was an inch from my face. As I instinctively opened my mouth, he pulled me closer and his cock slipped right in. He let go of my neck as I started bobbing on his throbbing cock. He was considerably larger than both Mr. Kelly and Mr. Howard, and his cock easily filled my mouth. It was a bit of a struggle to keep my mouth open wide enough to keep my teeth off his cock, and considering this was my 3rd blowjob in the last half hour, my jaw was already kind of tired.

Ed said, "Now isn't this a lot more fun than guzzling cum from your coffee cup? It sure is from where I'm sittin'!"

I sucked and slurped on Ed's throbbing cock for at least 10 minutes, and my jaw was so sore I thought I would have to stop, but I heard his breathing starting to get rapid, and I figured he was getting close, so I kept going. It was a real struggle to take his cock deep, I literally felt like I was stuffing it down my throat, but I did it 4 or 5 times. Finally, I heard him grunt, then he said, "OH...HERE IT COMES BITCH...HERE IT COMES!!! UGH...UGH...UGH!!!" With every grunt, a huge wave of cum shot right down my throat. It was crazy how hard he came!!!

With my lips gently around the head of his now super-sensitive cock, I kept sucking until I had every drop of cum he had. As his cock slipped from my lips, I sat back on my heels and massaged my jaw while both Ed and Mr. Howard commented on what a cum slut I was. I suppose that's my own fault, in a couple of ways, but it sure wasn't what I had planned when this whole thing started. Anyways, the guys were clearly "done" with me, so with a tummy full of cum, and absolutely zero dignity, I walked out of the office into the hall. I went and found a ladies room, as I was sure I needed to fix my make-up. Sure enough, my mascara was smudged because my eyes had been watering and my lipstick was pretty much gone.

I spent a little time making myself look presentable again, then texted Natasha to let her know I was done in Mr. Howard's office. Natasha texted back saying that I should head back to the office, my next appointment was at 10:30. I got back to our office at 9:45, so I took the time to freshen up, redid all my make up and put on a clean silk blouse. I felt like a whole new woman now, instead of the two bit slut who just got used and tossed aside by 3 guys!

I was sitting at Natasha's desk when Robert, from Bear Engineering came in. I had no illusions that he was here for anything related to work, but I greeted him professionally anyways, pretending I didn't know why he was here. He was carrying his briefcase, so I playfully asked him if he had anything interesting for me today.

He said, "Why don't you go lock the door, and we'll discuss it!"

I strutted to the door, putting a lot of sexy attitude in my walk and shake in my ass. I locked the door, then playfully looked back at him over my shoulder, and in my most sultry voice said, "So, what exactly did you want to discuss with me?" I slowly walked back over to him and stood close enough to feel his warm breath.

He said, "I can't stop thinking about the last time I was here."

I turned around so my back was to him, backed up so my sweet ass was firmly against his crotch and slowly started grinding against him while I said, "Yeah that was pretty spectacular! You were incredible!"

"Well sweetie, that's why I'm here." Then I felt his strong hands on my hips, and slowly find their way down to the hem of my skirt as he started kissing my neck. I was like putty in his hands! He slowly worked my skirt up to my hips, and then slipped his hands into my panties, gently grabbing my rock hard cock. As he started gently stroking me, he started nibbling on my ear, and it was driving me crazy! My cock was already covered in precum and he whispered in my ear, "Yeah, that's it you sexy little thing, just let it happen, I'll do all the work.

In just a minute or two, I came as hard as I'd ever cum in my life, and his left hand was full of my warm creamy cum. As soon as I was done, he told me to slip off my lacy panties, turn around and lean over, face down the desk. As I did, I soon felt a bunch of my cum drizzled directly on my rosebud. He said, "Oh, honey, I've been thinking about your sweet ass for a week," then I felt his cum covered cock resting against my ass. He applied a little pressure, and I gently leaned back into him until I felt the swollen spongy head of his cock squeeze its way in.

I let out a very girly "Ooo...Robert!" Even though having his huge cock in my ass hurt, it also felt awesome! With a couple inches of his cock impaled in my sweet ass, Robert held his hand to my face and told me to lick the rest of my cum off it. I cleaned off every delicious drop, then I felt both his hands grab my hips as he slowly buried his cock inside me. My ass felt like it was on fire, but yet I didn't want him to stop. He started slowly pumping his entire length in and out of me from where just the tip was barely inside me, to where his hips were pressed hard against my ass cheeks. After a couple minutes, the burning sensation was gone, replaced by intense pleasure, and I think he could tell that, because he started picking up the pace. Feeling his cock pumping in and out of me got my own cock hard again, though I was face down on the desk with my arms splayed wide, so I couldn't do anything about it.

Robert kept telling me how tight my ass was, and how good it felt, while I kept telling him how big his cock was and how good it felt stuffed inside me. I told him how after the last time he fucked me, how I enjoyed the feeling as his warm cum slowly oozed out of my gaping ass, and how it soaked my panties and smeared all over my stockings.

While he had already significantly picked up the pace, now he started driving his cock into me with much greater force as well. As his hips slammed into my ass cheeks, they made an audible "slap", it sounded just like he was like he was spanking me. The power of that big meaty cock working me over was crazy intense, and I started moaning and squealing with each stroke. For ten solid minutes, he ravaged my ass like I didn't even know was possible. Soon I found myself begging him with each stroke saying, "OH...ROBERT...OH...YES...PLEASE...OH...GOD...PLEASE. YES...FUCK...ME...HARDER...PLEASE...YES...YES...YES...YES...YES!!!!!"

Robert's hands gripped my hips tighter as he was absolutely plowing into my ass with all he had, and soon I felt his torrent of cum unleashed inside me. We stayed motionless for a minute or so as Robert's orgasm subsided, and then I felt him slowly start to pull his shrinking cock from me. As soon as he pulled out of me, I tried to squeeze my ass shut to hold in his cum, but to no avail. A steady ooze of cum dribbled down my thigh as I scrambled to slip my panties back on. Once I got them on, I sat back against the desk and relaxed a bit and I felt his warm load completely fill my cute little panties, coating my cock and balls, and leaking out the leg holes and oozing down my thighs. At some point while he was impaling me with his meaty cock, I must have cum also because the front of my blouse and skirt had cum smeared all over them.

Robert got his pants back on, walked over to me and gave me a deep, passionate kiss, then headed out the door without saying anything at all. I sat there for another minute or two, reveling in what just happened, then set out to get cleaned up. I stripped down, and then put on new stockings, and a sexy black lace bra and panty set. I put on a new black skirt, and a white lace blouse, that wasn't necessarily see-through, but you could definitely tell I was wearing a black bra. As I was fixing my make up, I noticed that my cum was smeared all over Natasha's desk, so I cleaned it up as well. I put all my cum soaked clothes in my bag, and put them in the closet, then texted Natasha, "My 10:30 appointment went very, very well!"

She texted back, "Glad to hear it. Now you should go get yourself some lunch, you have a long afternoon ahead of you! Make sure you're back to the office by 1:00."

I went out and had a nice relaxing lunch at an outdoor cafe, and just sat in the sun and thought about what a crazy morning I just had. I was already feeling kinda tired...turns out that giving three blow jobs in an hour, then getting man-handled and fucked doggy style will kind of tire a girl out! Be that as it may, I was sure that Natasha had more in store for me this afternoon, and to be honest, I was actually looking forward to it!

At 12:50, I headed back to the office, and when I got there, as I walked into Natasha's office, Christi was waiting for me. She was sitting on the edge of the desk with her legs crossed, and God, she looked stunning!! After I picked my jaw up off the floor, all I could manage to say was, "Oh, hey Christi, what are you doing here?"

"Oh Steff, you're so silly, I'm your 1:00 appointment!"

"Wait...you're here to...to see me? Why?"

"Well, Natasha and I were chatting a couple days ago, and she mentioned that one day she had a stiff neck, so she asked you to massage it for her. She said that one thing lead to another, and that you two ended up on the floor with your face buried between her luscious thighs. She said it had been a very long time since anyone has licked her pussy like you did. That's why I'm here sweetie."

She gently put her hand on the back of my neck, pulled me close and kissed me. It was a tender, but very erotic kiss that went on and on. Once it broke, my trembling hands were cupping and fondling her tits through her silk blouse. Without either of us saying a word, she stood up, and I carefully started unbuttoning her blouse. As her blouse fell open, her tits were now only constrained by her white lacy bra. I slipped her blouse off and tossed it on the desk, then reached for the zipper on her skirt. I slowly unzipped it, and she slowly grinded her hips as I shimmied her skirt down over her curvy hips and to the floor. She stepped on foot out, hooked her skirt on the toe of her pump and flung it out of the way.

She looked exquisite standing there in just her bra, panties, stockings and pumps! I unrolled Natasha's yoga mat, and we both knelt down on it. Christi lay back, and I started kissing her again, our tongues wrestling in each other's mouths. Soon I started working my way down. Her bra clasped in the front, so as I undid it, I started kissing and sucking her beautiful tits. After a minute or two, I continued my way down until I got to her tiny thong. I slipped it off her, she parted her legs and I nuzzled my face into her sweet shaven pussy. She was already wet, and as my tongue wriggled its way inside her, she let out a loud sexy sigh. Her pussy tasted so sweet, as I continued working her over with my tongue and sucking on her clit. Christi wrapped her legs around me locking my face against her pussy with her luscious thighs. She started grinding and thrusting her hips to meet the rhythm of my tongue, and for the next ten minutes, she moaned and sighed as I licked and sucked her sweet pussy. Soon she was saying, "Oh Stephanie, yes, lick my pussy baby! Yes, sweetie, please make me cum! Come on! YES, BABY YES, LICK IT, YES, OH GOD, YES, HERE I CUM BABY! HERE I CUM! OH YESSSSSSSSSSSS!"

I could feel her pussy throbbing as I was licking and slurping up her delicious cum. It was friggin' incredible! She kept her thighs locked around my face as I gently licked her pussy clean. Eventually, she unwrapped her thighs, and after giving her pussy several gentle kisses, I sat up. Christi had a huge smile on her face, then sat up and said, "Natasha wasn't lying, that really was incredible! Now I see why she..." Christi stopped for a second, looked me in the eyes, then down at my skirt. "Uh, Stephanie. Sweetie. What's that?"

Looking down, my hard cock was making a significant bulge on the front of my skirt. Apparently Natasha hadn't mentioned that, and I really didn't know what to say. All I came up with was, "Um, well..."

Christi then said, "Hike up your skirt sweetie." I was so embarrassed I couldn't even look her in the eye as I slowly hiked up my skirt, high enough to show my cock encased in my black lace panties. After a very long and awkward silence, Christi said, "Well isn't that interesting. Sweet little Stephanie has an adorable little cock. Natasha hadn't mentioned anything at all about this!"

After another awkward silence, she said, "Well, don't just sit there, get on your back baby...I'm going to put that thing to use!" I laid on my back, and Christi straddled my thighs. She worked her way up until I could feel her warm pussy rubbing my cock. She reached down, grabbed my cock and slowly lowered her pussy onto me. "Mmmmmm, I came here to get my pussy licked, and I was planning on licking yours. Honestly, you were going to be my first, so I sure wasn't expecting this!"

Christi sat upright, cowgirl style, and started grinding and riding my cock. The sight of her beautiful tits bobbing up and down was awesome! I was super worked up, moaning and sighing as this smoking hot woman rode my throbbing cock. She was really getting into it as well as she rode up and down every inch of my cock slamming her pelvis into mine with every stroke. Looking me in the eyes, she said, "Come on baby, let me feel you cum inside my sweet pussy. Give me your load of creamy cum, so I can feed it right back to you sweetie."

All I did was give her a slight smile, and she said, "Mmmmmm, you want that don't you? You want to lick all your gooey cum from my hot pussy don't you? Come on baby, I want to hear you say it. Tell me you want it!"

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