Summary:
After giving his boss a private moment of relief in the office, Tyler spends the day working closely with him on a critical presentation. Later at home, dressed in feminine attire, he shares an intense encounter with his roommate Jake that leaves him craving more. The next morning, he quietly wakes Jake before heading back to the office, where mounting pressure over an important contract leaves both men anxious about the outcome.
Here is your Story: I Sucked My Boss Then My Roommate All Night
After I gave Mike head in his office first thing in the morning, we worked feverishly to prepare for our Monday meeting. I worked mostly at my desk and him at his, but we had lots of interactions to make sure we were on the same page about every detail. Sometimes we would shout to each other across the hall. Sometimes we would wander into the other’s office and go over some diagram or spreadsheet or hash out a new idea.
My blowjob seemed to have had a magical effect on my boss. It appeared to have washed away his fears and reduced his stress level to zero. He was smiling and laughing, confident that we were going to land the MDI contract and save our jobs. Mike ordered in lunch and we shared it over his desk while brainstorming anything that could go wrong tomorrow. We made a punch list of last-minute items, some for him to follow up on and some for me. When we finished eating I went back to my office to take care of those annoying loose ends.
Deeper Into Character
Some time in the afternoon I realized that doing office work while dressed as a woman pushed me even further into my female persona. Hours and hours of watching my manicured fingers work the keyboard and seeing my reflection in the computer screen, long hair and red lipstick, made me feel more and more feminine. I was constantly looking down at my smooth cleavage on display in my low-cut gray t-shirt. Everywhere I looked I saw a pretty girl, me. It was making me horny again.
I couldn’t stop thinking about how it felt to take Jake’s cock deep in my throat for the first time ever that very morning. I thought about how I got down on my knees in Mike’s office and undid his pants. Most of all, I thought about how unbelievably hot it was to make a big, thick cock shoot off in my mouth. I had done it three times now, and I wanted more. Much more.
I tried to keep my mind on my work, but I kept wondering if Mike would be interested in maybe letting me suck him off again. I peeked into his office, hoping to catch his attention, but he was totally engrossed in the task at hand. I sighed and made my way to the ladies’ room to pee and freshen up my makeup. I checked on Mike again on my way back but he was still focused on his laptop. Just like with Jake the other night, I didn’t want to come on as too much of a slut, so I slipped back into my office and went back to work.
I lost track of time and it wasn’t until early evening that Mike finally appeared in my doorway.
“I think it’s time to call it a day, Tyler,” he said. “We’ve done all we can do.”
I nodded, hoping for some kind of suggestive comment that could lead to us fooling around again.
“Why don’t you go home and rest up?” he suggested, no hint of friskiness in his voice. “I want you at your best tomorrow, OK?”
“But Mr. Reynolds,” I said in a saucy voice, batting my eyelashes at him. “I think you’ve already seen me at my best, don’t you think?”
“Ha ha,” he laughed courteously, not taking my bait. “I sure have, Tyler. Let’s call it a day, OK?”
“Umm, sure,” I said, picking up on his vibe. “I’ll see you tomorrow. We’re going to nail this, right?”
“We sure are,” he agreed.
Frustrated Desires
I drove home frustrated. I was dressed as a sexy woman all day, in the office alone with my sexy boss, and I only got to blow him once. I was dying for more. God, I’m such a slut! I scolded myself, thinking about how much I wanted to feel my lips wrapped around yet another hard cock, how much I wanted to feel it shooting off in my mouth.
I was already planning on how I was going to seduce Jake the moment I walked in the door. Unfortunately, our apartment was empty when I got home. I flopped down on the couch, horny and irritable. I texted Jake, “where are you?”
“Out,” he responded. “How’s things? You ready to fool them tomorrow?”
“All good!” I responded. “But I definitely could use your help to get into my role, if you know what I mean.” I added the purple devil emoji.
“Be there soon,” he replied, adding a thumbs up.
I smiled to myself, reassured that Jake appreciated everything I had to offer. I scrounged up a quick dinner, took a shower, and dove into the box Sarah sent me to find a cute outfit to wear for Jake. I picked out a baby-blue silk pajama set. It had a spaghetti strap top with loose boxer shorts that rode low on the waist and high on the thigh. My new breasts looked amazing in silk lingerie, firm and full, every curve clearly visible. My hard nipples poked out against the soft fabric.
I tied my light-brown hair back in a pony tail, coated my lips in shimmering pink gloss, and brushed just a tiny bit of makeup on my face to highlight my eyes and color my cheeks. I wore small silver hoops in my ears and bracelets on my wrist. I checked Jake’s location on my phone. He was already here. I looked out the window and saw him on the sidewalk, walking toward our building. It gave me chills to know he was on his way, dropping whatever he was doing to be with me.
I stood in our living room, my heart fluttering, my eyes fixed on the door. When it pushed open I looked into Jake’s face and saw a look of primal hunger. He kicked the door closed, took two steps forward and wrapped his arms around me. There were no preliminaries. Jake brought his lips to mine and kissed me passionately, forcing his tongue into my mouth and grinding his hips into me. It was our first real kiss.
He slipped his hands up under my top and squeezed my breasts and pinched my nipples. I could feel his hard cock pressing into me. It was overwhelming, and I had never been so excited in my life. Jake was taking me with his tongue and hands and his thrusting hips, and I was more than willing to give in to whatever he desired.
“You’re so fucking sexy,” he panted into my mouth. “I’ve been thinking about you all day.”
I sighed and kissed him harder, swirling my tongue over his and grinding my belly into him. I dropped my hand to the front of his pants.
“What exactly were you thinking?” I asked teasingly as I began to stroke.
“I was thinking how lucky I am to have a sexy cocksucker for a roommate,” he growled.
Jake’s words made me shudder. When I took him balls-deep for the first time that very morning, I felt proud to be a deepthroat cocksucker. But that word was only in my head. Hearing it out loud was a different thing altogether. It was naughty and thrilling to hear Jake call me a cocksucker. I knew that some girls might be turned off by being called a cocksucker, but not me. Jake’s crude language turned me on like crazy. I wanted to be the sexiest cocksucker possible for him.
I dropped to my knees and went to work on his pants.
“You like me being a… cocksucker for you?” I asked, batting my eyelashes up at him as I undid his belt and opened the snap on his jeans.
“Oh, yeah,” he groaned as I pulled his zipper down with my bright red, manicured fingers.
I shuddered at my own words as I pulled Jake’s pants and briefs down to his ankles, letting his cock spring free. He kicked off his shoes and jeans as I reached up to take his throbbing shaft in my pretty hand. He pulled his shirt over his head, leaving him standing over me naked as I kneeled before him, jerking his erection in my fist.
“Yeah, baby,” Jake cooed. “I love that you’re my sexy cocksucker.”
Again, his words made me tingle with desire. I loved being a cocksucker for my studly roommate. Deep down, I realized it was what I always wanted. I parted my lips and leaned forward, taking his throbbing penis into my hungry mouth.
“Mmm,” I moaned happily, smiling around his thick shaft in my mouth. It thrilled me to know I was giving him pleasure yet again. I loved his hands cradling my head as I sucked him.
“Say it again,” I said breathlessly, giving his shaft long, wet licks.
“What?” he asked.
“Say it again,” I repeated.
He cocked his head at me, confused.
“Call me a cocksucker,” I said breathlessly.
A flicker of understanding flashed across his face.
“Really?” he asked. “You like it when I call you a cocksucker?”
“Uh huh,” I said, kissing all over his wet cockhead. “I love being a cocksucker for you.”
“Yeah?” he said, a big smile spreading over his face.
“Yeah,” I panted, licking his shaft with long, wet swipes of my tongue. “Say it again. Talk dirty to me.”
To make sure he believed me, I looked up at him and sucked his pulsing shaft into my mouth and took him deep until my lips were pressed to his balls.
“Oh, FUCK! You little slut,” he roared. “That’s it! Suck my cock, baby. Suck my whole fucking cock you sexy little cocksucker.”
“Mmm!” I squealed around his shaft, letting him know I loved it.
“Yeah, you dirty cocksucker,” he went on, “I love my cocksucking roommate! Yeah baby, on your knees, deep-throating me! Fuck! I love it!”
I kept sucking, chills going up and down my spine at his dirty words.
“Are you a slut for me, baby? Are you my little cocksucking slut?”
I sucked him madly. I couldn’t get enough.
“Are you!” he demanded, grabbing my pony tail and pulling my head off him. He held his shaft in one hand and my head in the other, keeping a few inches distance between them as I struggled to suck him back in.
“Are you?” he demanded.
I looked up at him desperately, trying to engulf him but he was too strong.
“Say it!” he growled. “Are you my little cocksucking slut?”
“I… I…,” I gasped.
He held my head off, not letting me have what I desperately wanted.
“Yes!” I eagerly agreed. “Yes! I’m a cocksucking slut! Your cocksucking slut! Can I have your cock now? Please?”
He laughed, still not letting me go.
“You want me to cum in your mouth, baby? Is that what you want?”
I looked up at him, nodding.
“Say it,” he whispered.
“I want your cum,” I said. “I want to swallow your cum.”
He looked down at me, gesturing for me to continue.
“Ooooh, Jake. I’ll be your slut. I’ll suck your cock! I’m your cocksucker. I want you to cum in my mouth. I want to swallow your cum. Anytime. I’ll suck you off anytime. Please!”
“That’s better,” he chuckled. Holding my head in one hand, he brought his other to his mouth and wet his middle finger. He brought his wet finger to my mouth and traced a wet circle around my lips, still holding a firm grip on my pony tail.
“You have such pretty lips, baby. You always did.”
I closed my eyes and groaned, loving the feel of his wet finger.
“So pretty,” Jake cooed, “such pretty, cocksucking lips.”
Jake pushed his finger into my mouth and I immediately started sucking on it, wrapping my lips tight and fluttering my tongue.
“Yes, baby,” he said, “show me what a hot cocksucker you are. Show me how you suck with that pretty mouth.”
I was wild with desire now, sucking his finger like mad. I brought both hands to his hard shaft, stroking him as I sucked his finger, his words exploding in my ears and mind.
“Good girl,” Jake said, watching me submit completely, drooling over his finger, massaging his cock and squealing with excitement. “Good little cocksucker.”
Jake released his grip on my head and I desperately gobbled his erection back into my mouth, sucking madly, drool dripping down my chin, both hands fisting the base. Jake’s temporary denial of what I craved ignited a frenzy inside me. I sucked his cock madly, taking him deep, slurping and drooling all over his shaft, fisting the base and rubbing his balls. The whole time Jake kept up a steady stream of dirty talk, calling me a cocksucker and a slutty cock fiend. He even called me a cum-guzzling slut. I sucked his balls and jerked him wildly while he called me a cock whore. He told me he was going to bring his friends around make me suck them off too, one after another.
Jake’s words blazed in my brain, taking me to new levels of excitement. Jake said he was going me make me his personal cocksucking bitch and was going to charge his friends $100 every time I swallowed their cum and $200 if they wanted to cum on my face. He said he was going to film me on my knees, blowing dozens of guys, gulping down loads of cum. I squealed with excitement around his fat cock in my mouth every time he demeaned me and told me of the nasty things he planned for me. When Jake said he was going to start a channel on Pornhub called Tyler Sucks Cock and show me looking right into the camera with my face covered in cum and a hard dick in my mouth and one in each hand it set us both off.
I held my lips wrapped tight around head of Jake’s shaft while I fisted the base and jerked myself off, too. We climaxed together, Jake filling my mouth with sperm while I spurted onto the living room floor.
“Yes, you sexy cocksucker! Drink my cum! FUCK!” Jake cried as he shot over and over again, coating my teeth and tongue and gums with gooey semen. “YES!”
The red numbers on my alarm clock glowed 12:00. I was lying in bed, trying to sleep, my mind racing. I was nervous about our meeting with MDI tomorrow, my job on the line. I was thinking about my sudden feminization, not just that I was dressing up, wearing makeup, and had incredibly realistic fake boobs, but that I had quickly developed an insatiable desire for cock. Had I been harboring these desires my whole life? I didn’t know. One thing I was sure of, though, was that thinking about sucking Jake’s cock and his dirty talk made me incredibly horny. The boner pressing against my silk, baby-blue pajama bottoms left no doubt.
I reached down and stroked myself, an endless loop of Jake’s nasty words playing in my head. I shot off in less than a minute, then calmed down. Eventually I drifted off to sleep, and the next thing I knew my alarm was buzzing. I slapped it quiet and lay on my back to take stock of the coming day. Instead of planning all the things I had to do for work, or what I was going to wear, I was thinking about only one thing, when was I going to get my next chance to suck cock?
I was worried because I knew Jake would sleep late and I wouldn’t have a chance to blow him before work. Mr. Reynolds was acting weird yesterday afternoon and didn’t seem interested in a repeat performance of yesterday morning. To make things even worse, Jake was going to be away for work that night, so there was a very real possibility I might not get to suck a single cock all day. I sighed, frustrated. I needed to suck cock in the worst way. Just thinking about it made my mouth water.
Fuck it! I decided. I got up, brushed my teeth, and put my ear to Jake’s door. I could hear him snoring softly. Ever so quietly, I pushed the door open and tiptoed to his bed. Fortunately, he was lying on his back. Gingerly, I pushed the sheets back. He kept snoring. Wow, I thought, taking in the sight of him wearing only a pair of black boxers. How come I never realized how hot my roommate is before? Jake had six-pack abs, broad shoulders, and a dusting of dark curls on his chest. His legs and arms were toned and muscular. He exuded raw, masculine power.
Standing over him wearing lingerie, my boobs pressing out against my silk top, my painted fingernails, Jake’s masculinity made me feel even more feminine. It also filled me with desire. I felt bad that I was going to disturb his sleep, but the idea of going a full day without cock left me no choice.
Delicately, I kneeled over him on the bed and took the elastic of his boxers in my painted fingers. I slowly pulled them down to his knees, revealing his flaccid member. I looked to his face, still snoring. I cradled his soft penis in my dainty hand, leaned forward and lifted it to my lips. I took it in my mouth and swirled my tongue around and around, like a propeller. After only a few moments I felt a response. It began to grow. The snoring stopped.
I felt Jake’s hand on the top of my head as his cock inflated. In less than a minute Jake was fully hard. He groaned sleepily as I began to bob on his thick, hard cock. I stretched my jaw and took him deep with long, slow strokes as my tongue fluttered around the smooth skin of his shaft. Jake dropped his other hand to my head as I took his ball sack in my hand, massaging his nuts as I sucked him. Jake cradled my skull as I increased my efforts, keeping my lips wrapped tight around him in a perfect O. I moaned and squealed around his thick meat in my mouth, thrilled to start my day by sweetly sucking my roommate’s dick.
Jake was thrusting his hips off the bed now, fucking his hard cock into my sucking mouth as I drooled all over him.
“Yes!” he shouted as he gripped my head tight. “YES!”
I held his throbbing cockhead tight in my lips and fisted him as he shoved his hips upward and unleashed a torrent of sperm into my hungry mouth. I held still, my tongue swirling over his squirting head, savoring each blast of hot cum.
“Mmm,” I purred as I gently milked his shaft and balls, eager to squeeze every last drop of semen from his heaving testicles. When he was done I planted a wet, loving kiss on the head and licked all over, cleaning the sperm and spit from his deflating member. I spied another drop seeping out from the tip and licked it clean, then rose to my feet.
At least I got to give one blowjob today, I thought to myself, proud of having taken the initiative.
“I have a big day,” I said matter-of-factly, as if it was no big deal that I snuck into his room and woke him from a deep sleep with a cum-guzzling blowjob. “I’ll see you tomorrow, OK?”
Jake chuckled, amazed at his good fortune. He rolled over, pushed his face into his pillow and went right back to sleep as I headed off to the bathroom to get ready for the biggest day of my young career.
I got to the office early and saw that the lights were already on. I checked myself in the mirror. I fixed up my lipstick and brushed my hair so it was just right. I was wearing the black pantsuit and white blouse that Sarah had picked out for me on Saturday. I added medium-sized silver hoop earrings and wore the silver chain around my neck with a black, circular pendant that dangled in my cleavage. I wore the black pumps with 2″ heels. Just like on Saturday, the overall effect was incredible. The jacket was sharply tailored to accentuate the curve of my bust and my waist. My face was stunning. The black pendant hung in my cleavage, my white shirt suggestively unbuttoned, allowing a furtive glimpse of my black bra if I leaned over just so.
I dropped my things in my office and leaned into Mike’s doorway.
“You ready for today?” I asked optimistically.
Mike looked up at me and did a double-take.
“Wow,” he said, “you look stunning.”
I gave him a saucy smile and cocked my hip out.
“Thanks boss,” I grinned.
Mike forced a sickly smile. Despite my morning cheer, he looked like a wreck. He had a nervous look on his face and sweat on his brow. His suit jacket was draped over the back of his chair, his sleeves rolled up and tie loosened. He looked like he had been at work for hours.
“I don’t know,” he groaned, “if we don’t get this contract we’re done. But you being here, looking like that, gives me hope we can pull it off together.”
