Femboy Executive Assistant Pt. 02

Jackie arrived at work at 9:00am sharp. He was a little nervous after recalling the events of his interview with his new boss and what was to come with his new job, but he was very excited about the pay and his boss was definitely not a bad man to serve under.

He was wearing a skirt that rested a few inches above his knees and a three-button blouse. Under his skirt were his favorite pair of panties which were pink with a tiny white bow in the front.

He was shown to his desk by the head of HR after signing some additional disclosures regarding his employment at the office. His desk was right outside his boss's office and it was of ample size.

His first day was primarily spent doing various tasks that HR had assigned him in order to fully onboard him to the company. He was blown away at just how many papers he had to sign and how many training videos he had to watch when he was just an executive assistant.

About half way through the day he got a buzz from his boss to come into his office and he quickly got up and headed through the double doors that led into the office.

"Well good afternoon to you Jackie. I hope you haven't been too bored here on your first day. I know the first couple of days can drag along with all of the HR related tasks you need to complete but at least once it's done you don't have to deal with it anymore." Tom said as he reclined back in his chair and extended a hand motioning Jackie to take a seat.

Jackie sat in the chair across from Tom's desk and chuckled. "Yah it's been a bit boring but I know it's all necessary. Besides, I am getting paid for it so I can't complain." Jackie said as he looked around the immaculate and sprawling office.

"Yah probably not quite as fun as the day you interviewed. But don't worry, we will get you onto some fun tasks rather quickly." Tom said as he smirked.

"Well whenever you have some new tasks for me, I'm ready to take them on." Jackie said as he chuckled nervously knowing full well what Tom was referring to.

"Well why don't we start now then. It's lunch time and I sure could go for a nice blowjob while I eat my lunch. If you do a good job, maybe I can feed you a load for lunch." Tom said as he reached down and started to undo his pants.

Jackie stared at Tom for a second before standing up and heading over to Tom's side of the desk and getting on his knees. He was still a bit apprehensive about the whole situation but honestly it wasn't a bad gig. Being a total slut for a big cock was one of his favorite things to do, and now he was even getting paid for it.

Tom adjusted himself as he slid his pants and boxers down revealing his semi-hard cock. Jackie moved in between Tom's legs and nuzzled his face into his balls just like when he was interviewing.

Tom chuckled as he felt Jackie settle into his role perfectly. "Good job. You remembered I liked my balls taken care of. Get them nice and worked up. The more work you do on my cum factories, the bigger the load you'll get for lunch." Tom said as he began to eat his lunch.

Jackie smirked and realized he would definitely be enjoying this new job. Tom's balls had a strong musk to them after being confined in his pants all day but it was nothing a lavish tongue bath couldn't wash away.

Jackie made quick work of Tom's large testicles by tracing his tongue up and down his sack before sucking one of his balls into his mouth and swishing it around. After thoroughly sucking on one, Jackie let it plop from his mouth, glistening with saliva before moving to the other and repeating the same technique.

"Damn Jackie, I knew picking you was a good idea. The way you work my fat nuts is like magic. I can feel them working overtime on your lunch right now." Tom said as his now rigid cock started to leak precum as his balls were being worshiped.

Jackie smiled at the praise and continued to lick and suck on Tom's balls until they were thoroughly coated in saliva and his cock was throbbing in need.

Once Tom's cock was leaking a copious amount of precum, Jackie traced his tongue from Tom's balls, up the underside of his cock until his tongue reached the tip and he lapped the precum up.

Tom moaned as his cock was now being toyed with by Jackie's tongue and his cock throbbed ready for a mouth to suck him.

Jackie wrapped his skilled lips around the head of Tom's cock and provided the perfect amount of suction as his lips stayed wrapped around the crown of his cock. Jackie's swirled his tongue expertly around the thick mushroom head and sucked gently as he nursed on the tip.

"That's it. Suck that dick slut. You and my dick are going to become best friends and you are going to spend quite a bit of time under this desk nursing my cock and balls." Tom said as he leaned back and enjoyed the show.

Jackie continued to suck Tom's dick and started to take more of his massive cock into his mouth. Jackie soon realized just how difficult it was to push more of Tom's cock into his mouth as not only was Tom's cock large in length, but it was thick as well. Tom was sporting 10 inches and the girth was making it quite difficult for Jackie to push down past 4 inches.

Tom looked down at Jackie struggling and chuckled. "Looks like we are going to have to work on that throat game. Only true experts can deepthroat this monster. We will do some proper throat training though, don't you worry." Tom said as his cock throbbed and pulsed in Jackie's mouth.

Jackie was offended at the mention of needing training to deepthroat. He was not a newbie when it came to deepthroating but even he was having a very difficult time working this monster. He resigned himself to just putting all of his effort on working the amount of cock he could fit and massaging Tom's balls while he sucked to earn Tom's load.

Tom rested a hand on Jackie's head and moaned as he was approaching his orgasm. Tom's balls were working overtime churning up a massive load for Jackie to swallow and before he knew it, Tom's cock was shooting out thick rope after thick rope.

The first shot took Jackie off guard with no warning from Tom. The first shot hit the back of Jackie's throat with enough force to make him gag and sputter but he couldn't pull back because of Tom's hand holding him in place. The second shot seemed even more powerful but Jackie was at least expecting it so he started to swallow the large amount of sperm that was being shot in his mouth.

Jackie felt Tom's cock tense 7-8 times shooting out full load each pulse before it started to slow down and Jackie felt like he had a full course meal with the amount of cum Tom had just poured into him.

Jackie continued to nurse on Tom's drooling cock for a few minutes until it finally started to soften and it popped free from Jackie's mouth. He coughed a few times and stood up before flattening his skirt and straightening his blouse.

"That wasn't half bad, my new assistant. Not the worst blowjob I've had but far from the best. Maybe I'll have my boy at home teach you a thing or two about giving world class throat jobs." Tom chuckled before he pulled his pants and boxers up and adjusted himself.

Jackie scoffed at the thought of needing blowjob lessons, but he was also intrigued in the fact that someone could actually throat that monster. "Well maybe I will have to get some lessons. Is that all you needed from me sir?" Jackie said with a bratty smirk.

Tom waved Jackie off with a smile and said that once he was done with the tasks HR had assigned him, he was free to leave early.

Jackie perked up at that as he realized he really didn't have much left to do from HR and it was only 1:00pm. He quickly finished up and headed home early with a smile on his face.

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Tom was seated on the couch back at his house and all that could be heard was licking and slurping sounds coming from underneath him. His platinum blonde femboy currently had his face upright on the sofa directly underneath Tom's ass.

Tom's balls rested heavily on the boy's throat as he stroked his cock idly while he relished in the boy's tongue lapping at his asshole. One of Tom's favorite ways to relax after a long day was to come home and have his boy service his asshole until he was ready to blow his load down the boy's throat.

The only problem was that his boy was not very fond of eating Tom's ass, especially after a long day at work where it would get sweaty and musky being confined all day.

"Get that tongue in there slut. Get that asshole nice and clean and I'll give your throat a nice creamy reward. This may be the last time you need to eat my hole like this. My new assistant may be taking your spot as my rimmer. He gave a mediocre blowjob today, nothing like your tight throat. I might relegate him to be my ass licker while I save my cock for your throat only." Tom chuckled as he stroked his cock faster.

The boy started to lick and suck on Tom's asshole with more fervor at the thought of never having to give a rimjob again. He was more than happy to give his throat up if it meant not having to lick Tom's ass anymore.

Tom stayed riding his boy's tongue for a good 15 minutes before he scooted backward and angled his cock straight down towards the boy's mouth. The boy opened immediately and Tom thrusted forward and hilted his monster cock balls deep in the boy's throat in an instant.

Tom reached down and grabbed the boy's neck with both hands before roughly fucking his throat with reckless abandon. The boy gagged and sputtered but remained still as his throat was being thoroughly fucked.

"Oh yeah this is what I needed. Tight ass throat pussy is the only way I need to cum. That blowjob earlier today barely did anything for me but this is going to make me cum buckets. Fuck your throat pussy has my dick spoiled." Tom said as he continued to pound away at his boy's tight throat.

Finally after about 5 minutes of intense throat fucking, Tom hilted himself balls deep in the boy's throat. His large and pulsing balls smothering the boy's nose as he came loud and hard. His cock pulsed and shot rope after rope straight into the boy's belly as Tom groaned loudly and felt the tight throat milking him of every last drop.

Tom shot close to 20 heavy ropes down the boy's throat before finally pulling out and sitting his asshole back on to the boy's mouth.

"Damn that was a good nut. Get back to tonguing my asshole until I'm ready to go again. I got about three or four more loads I want to dump down that throat pussy." Tom said as he settled back into sitting on the boy's mouth and enjoying his tongue and lips.

The boy groaned but resigned himself to rimming Tom hoping that it was his last day doing so. He quickly went back to sucking on the hairy hole before sticking his tongue against the wrinkled flesh and cringing.