tagTranssexuals & CrossdressersJesse's Dream Job - The First Day

Jesse's Dream Job - The First Day


I should have put this at the beginning of the first installment of this series, but I was in such a rush to get it posted I forgot. I need to give "Jesse" credit for this story idea. He contacted me and asked if I would please write it for him. I didn't make him any promises as to how quick I would get to it, but the idea wouldn't leave me alone. It ended up pushing ahead of Helen and Jim's Vol. 2. Now Angel has asked for a sequel and I'd not refuse my lady's request for all the gold in...well, you get the idea.

Jesse didn't want to be late on his first day so he got to the office about 20 minutes early. He was looking sharp in a black suit pinstriped in light blue. The shirt matched the pinstripes and the tie was made up of reds, purples and a little of the light blue to bring it all together. Jesse had never had a tailored suit in his life, but now he knew why someone would pay so much for one. They made the guy wearing it look like a movie star. Antonio had worked his magic on the suite overnight and when Jesse had stopped by early this morning to pick it up Antonio had insisted that he wear it today, telling him that Ms. Angel expected it.

"My, my, my, don't you look fabulous!"

Jesse turned to see Rika coming through the door with big smile and a grocery bag. She was wearing a black pencil skirt with a crisp white dress blouse, unbuttoned just enough to show off a bit of cleavage. Sexy, yet professional.

"I'd have to say the same for you Rika. In fact, I'd say you are positively glowing this morning. The date with...um...I'm sorry I can't recall...


"Yes of course, it went well I take it?"

Rika's smile alone told the story.

"Oh yes! It was a wonderful evening full of romance and smoking hot sex!" Rika laughed "We're both walking a little funny today! Hey, since you're here why don't you c'mon into the conference room and help me set things up for the staff meeting."

Jesse followed Rika and her long legs into the conference room where she directed him to gather up plates, glasses and utensils for the food she had brought. They worked quietly, but comfortably together. When they passed by each other in the close quarters around the table their hands would casually touch the others body as they excused themselves by. Jesse had done some catering work back in his high school days and fell back into the easy rhythm of set up work.

Ms. Angel watched them from the doorway for a few seconds, impressed with how quickly they were acclimating to each other. She wondered how things would go with the rest of the crew.

"You two sure seem to be comfortable with one another."

Jesse and Rika jumped, startled by Ms. Angel's sudden appearance. They looked at each other and Rika shrugged as she said,

"I suppose so. Jesse just seems to know what needs to be done and then does it. I like it when a man sees a void and fills it."

"Oh, I agree Rika. But I like it even more when a man provides a void and I get to fill it." Ms. Angel said with a smirk. They all laughed and Jesse stepped over to Ms. Angel and asked,

"May I take your coat and hang it up?"

"Yes, please put it in the closet in my office."

It took Jesse a couple of tries to find the closet and by the time he got back to the conference room all the rest of the employees were there. Ms. Angel was sitting at the head of the large oval table and there was a seat between her and Rika waiting for him.

"Oh, here's Jesse now. Jesse, I would like to introduce you to Kara, Selena, Carla, and Pria. Ladies, this is Jesse." There were nods and mumbled hellos all around the table. "This is Jesse's first day with our company and he has been fully apprised of all of his job duties, but I ask you to be understanding with him as he settles in." Angel smiled at Jesse and then continued. "Later today we will be conducting a screen test with a very talented young lady who is new to this business, but very enthusiastic about making her big break. Kara, do you have the scene ready?"

"Yes Ms. Angel. I will only need to get some..."

Jesse focused on Kara as she talked. Her complexion was like cream and her green eyes and short red hair gave her very striking looks. She wore a bright blue blouse and Jesse could make out some freckles on her chest. Her blouse wasn't unbuttoned as far as Rika's though she still was showing a bit of cleavage as well.

"If you need it, Jesse can help you with the screen test. In fact I've already told him to plan on it."

"That will be great Ms. Angel."

"Good. Selena, how are the revisions to the screen play coming along? Will it be ready soon?"

"Yes, Ms. Angel. I'm currently rewriting the entire fourth act..."

Selena looked like a book worm personified. She wore square black rimmed glasses with straight black hair that hung to her shoulders. She had on a grey turtle neck sweater that made her eyes look grey and only a small amount of makeup. The tight sweater did a nice job of making the most of her small breasts. Even her voice seemed small and mousy. She looked like she was trying to fade into the chair she was perched on. In truth she looked and sounded like she would be far happier working in a library.

"...it should be finished by Friday."

"Excellent. Sounds like things are coming along very nicely. Carla, how are you and Pria coming along with the sets?" Carla glanced at Pria and said,

"Things are moving right along. We've got two of the sets finished and..."

At first glance Pria and Carla looked similar since they both had their long hair pulled back in pony tails. But that was where the similarities stopped. Pria had dark almost black eyes with shiny black hair and looked like she might have some Spanish heritage. Carla's eyes were bright blue and her hair was a soft brown. They were both wearing red polo shirts with the company logo that fit close to their bodies and accentuated their figures. Carla's shirt also accentuated her strong arms. These girls were used to doing hard work and it showed in their bodies.

"...they will be finished long before Kara needs them."

"Wonderful! It sounds like things are moving along smoothly and on time. That's all I have for this morning, does anyone else have something we need to discuss?" Selena cleared her throat and sheepishly raised her hand. "Yes Selena?"

"I was...er...wondering when Jesse will be available to help out with our individual...projects for this shoot?" Ms. Angel had to work to hide her smirk and Janice and Carla openly grinned at shy little Selena's question.

"If you need his services I'm sure he can stop by your office right after this staff meeting. Am I correct Jesse?"

"Yes, of course. I'm ready to do my best to help out in any way I can."

"There, it's settled. Everyone please be sure to grab some of the goodies that Rika picked up and thanks for coming in early for the meeting."

Ms. Angel pushed away from the table and the rest of the women followed suit. Everyone gathered up their stuff and began to head out of the conference room. Selena almost bolted from the room, but the others were more leisurely about it. Kara stopped and extended a hand to Jesse. As they shook hands she looked deep into his eyes and said,

"It's nice to meet you Jesse. I'm looking forward to directing you." She flashed him a smile and strode from the room. Ms. Angel said,

"As soon as Selena is finished with you come directly to my office. If anyone else asks for your help, tell them you are scheduled with me for the rest of the morning. Understand?"

"Yes Ms. Angel."

Jesse left the conference room to go to Selena's office as the other women were milling around and grabbing some snacks. He wasn't sure exactly where her office was but it didn't take long to figure out because each door had a name plate. After stumbling into the Studio he had to back track to a short hallway that ran off of the main one with an office on either side. The door on the left had Kara Dune on the name plate with a simple Director written beneath it. The door on the right said Selena Ryland, Screen Play Artist. Jesse shrugged after reading the title and knocked on the door. He heard Selena's quiet voice call 'Come in.' Jesse stepped into an office that had a modern feel to it with lots of chrome, black leather and glass. That was all Jesse had a chance to see because as soon as he closed the door Selena growled out,

"About fucking time! What the hell did you do, take a tour of the facility?"

Her voice sure didn't sound mousy now. She stood and stalked around her desk toward Jesse with the front of her black pleated skirt tented out over her hardon. That was when he realized she wasn't very tall. When she got to him she pulled up her skirt and grabbed her cock in her left hand as she reached up to the back of Jesse's neck with her right. She pulled hard as she said,

"Get down here! You can't suck me from way up there!" She pulled hard but couldn't move Jesse which only seemed to inflame her even more. "Down! Get down here! I'm about to fuckin explode I'm so fuckin horny and you're standing around like some statue!" Jesse realized that if he was going to keep his job he better do as she said. Selena wasn't directly in front of him so he bent at the waist and turned his head to the side to take her in his mouth. Her penis wasn't very long, six inches or so, but boy was it thick! It was all Jesse could do to get her in his mouth. "If that bastard hadn't run off with Michelle, I wouldn't be so damned horny!" As soon as Selena was in Jesse's mouth she began to hump him like crazy. With one arm along his back, the hand at the base of his neck and her other hand on the back of his head she thrust up into his mouth. "Does anybody ever think about how difficult it is for me to pour over those sexual screen plays for hours and hours without relief? NO!" She punctuated the NO with a hard thrust. Jesse was scrambling to accommodate her thick member, but his jaws were already aching. She had her skirt pulled up so she could watch her fat prick as it slid in and out of his lips. This turned her on all the more, making her hump Jesse's mouth even harder. Jesse could see her watching him out of the corner of one eye and out of the corner of the other he could watch her rise up onto her toes as she pumped her hips back and forth. Luckily for him, Selena was so pent up that it only took about five minutes of thrusting in wanton abandon for her to shoot a huge gooey glob of cum into the back of his throat. Jesse gagged, coughed and swallowed hard as Selena sent three more hard shots into his throat. "Oh god! That is so good! I haven't cum with anyone since that little douche ran off with Michelle and that has been way too long!"

Selena released Jesse's head and stepped back from him. She had a wicked little smirk on her face as Jesse rubbed his aching jaw muscles.

"I'm sorry. Did I hurt you?"

"Not really. It's just that you are very thick and my mouth only opens so..."

"I am thick aren't I?" She interrupted as she looked down and gripped her cock again. Her fingers didn't even come close to encircling it. "Here, put your hand around it." Selena took one of Jesse's hands and wrapped it around her still firm penis. She put her hands on her hips as Jesse kneeled before her and held onto her. Even Jesse's hand wouldn't encompass her thick girl cock. "Oh I like this view, you on your knees holding onto me and even you can't get one of your big hands around me. If it doesn't fit in your hand, how do you suppose it will fit in your ass?" Selena chuckled at Jesse's nervous glance up into her eyes. "Whatdya say stud? Are you ready to bend over and take one for the screenplay department?"

"I'm here to help you in any way I can Ms. Selena."

"Ms. Selena...I like the sound of that. From now on you can call me that whenever you address me. Now. Undo those pants and show me my cock's new home for the next year." Selena swirled her finger in a circle as it pointed at the floor to show Jesse to turn around. Jesse turned around and undid his belt and pants then let them drop in a pool around his knees. Hooking his thumbs in the waist band of his boxer briefs, he added them to the pool. "MMMM, Jesse you have one nice ass." Selena stepped around in front of Jesse and handed him a condom. Where she'd gotten it he had no clue. "Put this on me." She said. Jesse took the packet from her and opened it. To Jesse's surprise it was bright red. She lifted her skirt up out of the way and Jesse rolled it onto her swollen member. It just barely fit and made an odd contrast to the black and grey ensemble she was wearing. She moved back to her spot behind him. "On all fours." She commanded, and Jesse complied. He was starting to breathe harder as she neared him and squatted over his ass. She pushed his shirt and jacket up onto his shoulders as she rubbed the lubricated tip around his sphincter for a second or two. Then she simply entered him. The sheer size of her took his breath away. She stayed still, fully inside him, relishing in the feeling. She could feel his muscular ass between her thighs and her balls were lying against his taint area. She could feel him quivering. Whether it was from the pain of her stretching his ass with her girl cock or the excitement she couldn't tell and really didn't care. She was just thrilled to be in someone's ass.

Jesse could feel the lace tops of her black thigh high stockings pressing into the sides of his ass and he felt her hands follow up along his back to come to rest on his shoulders. Then the fucking commenced. Selena started off slow, all hip action. She was grinding her thick cock into him with the sexy moves of an accomplished pole dancer, arching her back as she rode his ass. Not thrusting so much as wallowing in the thick mud of much needed sex. Selena was in no hurry and wanted to enjoy every second of this delicious tryst. Her modest short heeled pumps made soft swishing sounds as they fought for purchase on the cream colored carpet.

Jesse could feel the tendons of her inner thighs digging into his butt cheeks as she wriggled around against and inside him. He couldn't see her, but the way she was moving was sexy as hell and it was turning him on like crazy. Her tempo was increasing and her legs were getting tired so Selena laid along Jesse's back. When she pressed her sweater clad breasts against him he instantly knew that the sweater was made of cashmere. It was impossibly soft between her firm breasts and his muscular back, multiplying the sensuality of the experience. Selena slipped a hand around his torso as she snaked the other down to his crotch. She easily found his throbbing penis, but instead of gripping it she lightly ran her fingers over it.

"You seem to be enjoying this." She whispered in his ear.

"Yes Ms. Selena." He replied in a strained voice.

"Do you think I'm sexy?" she purred

"Oh, yes. Yes. Yes." He whispered and she answered with even more exaggerated hip movement and a,

"MMMMMM. I'm glad you think so." She took two fingers and thumped his pecker hard, causing him to jump and squeeze her cock with his sphincter. "Oh that was very nice." She licked his earlobe and then sucked it into her mouth. She went "MMMM" again and kept sucking on it as she thumped his cock again. Jesse grunted and let out with an,

"Ohhhhh." Of his own.

Selena knew that Jesse was all hers. She could do whatever she wanted with him and what she wanted was for him to cum the same moment she did. She began to thrust into him. Hard pounding thrusts with all of the pent up frustrations she had within her. She released his ear and grabbed his cock in her hand, squeezing it hard she said,

"I'm so close to cuming, I can't wait to explode in you! It feels so good to be buried in your ass that I think I could do this for the next eight hours and then slump off home to crash on my couch. I love how good you feel around my dick. I want you to cum with me."

"I can't."

"Yes. You can."

"I'm not supposed to cum."

"You want to don't you?"

"Yes, but..."

"I want you to cum with me. I want to feel your dick pulsing out hot shots of cream as mine is doing the same in your ass. I want to be one with you. Are you ready to cum?" All Jesse could do was nod his head. "Here we go." Selena began pumping his ass in earnest. Her balls were slapping against him and she was stroking his turgid cock with her hand. She had just had an orgasm so even though she was close she knew she could wait for him. She didn't have to wait long. Jesse began panting really hard and she felt him tense up beneath her. Something about making a guy cum while she was pounding his ass always sent her over the edge. The rest of Jesse's body went rigid and she felt his cum pulse down the length of his prick. That first pulse through her hand sent Selena into hot ecstasy filled convulsions. She emptied her balls into the condom in his ass as she milked his cock onto her office floor.

The little two person cum fest was over in about 15 seconds. Selena was spent and thoroughly satisfied as she lay on Jesse's back. It was all Jesse could do to keep from collapsing on the floor in his own cum. After a minute or so Selena pulled her feet up under her and stood up. The air felt cool on Jesse's newly exposed skin and his sphincter felt like it was never going to close up. Jesse had to squeeze it hard a few times to get it to feel like he wasn't gaping open. Selena reached down and patted his ass cheek as she said,

"I like watching a guy try to get back to normal after I've stretched him out. Seeing his asshole shrink and contract always makes me want some more." Squatting over his rump she rubbed the tip of her cock around his sphincter and pushed the head back inside him. "MMMM I so want to do you again, but I'd better not." She stood back up and walked over to pull a sheet of paper towel from a roll on top of a cabinet. As she wiped up she said, "I've already kept you too long and on top of that I'll have to hear about making you cum. That gets me in trouble every time."

Jesse got up off of the floor and Selena offered him the roll of towels. He pulled a couple off and cleaned himself up. They didn't speak as they straightened their clothes. Jesse took a couple of extra towels and wiped up the evidence on the floor.

"There's some spot remover in the top cabinet drawer. Use that to finish cleaning up." Jesse did as he was told and Selena sat back down at her desk and went back to reading the screen play as if he had already left. Selena heard him open the door and without looking up she said,

"Thank you for coming by this morning Jesse. I expect to see you first thing tomorrow morning as well, unless of course Ms. Angel needs you. Understand?"

"Yes Ms. Selena."

Jesse pulled the door closed with a soft click and hurried down the hall toward Ms. Angel's office. As he reached for the door handle Rika said,

"Knock first! Ms. Angel never likes for anyone to barge in on her!"

"Oh. Yea, right."

Jesse planted two quick knocks on the massive door and was rewarded with a muffled 'Come in.' Jesse turned the handle and stepped inside, the massive mahogany door clicking shut behind him. Ms. Angel's head was down over some papers on her desk and she absentmindedly twirled a pen in her hand while she read. As Jesse approached the desk he was once again struck with how beautiful she was and how feminine she looked. As he watched she took the pen and underlined a section of print and added a note on the side of the paper. Finished, she looked up at Jesse and a small smile touched her lips.

"I hope that Selena wasn't too hard on you. She's been pretty grouchy the last few weeks so I'm sure she must have had some serious pent up frustrations."

"Um...no Ms. Selena was...enthusiastic, but didn't hurt me...too much." Ms. Angel laughed and said,

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