“Look, Chase might be a real pain in the ass up at work, but he’s decent enough to me and faithful. He’s just…” she started. “He thinks he’s a lot bigger than he is, and thinks he’s a lot better than he is. Plus his jealousy is just maddening.”
“Yeah?” he asked.
“Yeah,” she sent. “He’s so paranoid that I’m going to leave him. The only time I ever want to leave him is when he’s being a pain in the ass about being scared I’m going to leave him.”
“I’m sorry,” he sent. There was a minute of silence before she replied.
“I shouldn’t have told you that,” she sent.
“I’m sorry for you,” he said, “but don’t worry, I’m not going to use this new knowledge against him in some nefarious plot.”
“Thank you Dexter. You seem like a really good guy. By the way, I meant to tell you,” she sent. “I’ll have a surprise for you on Monday, if it gets here today that is.”
“What’s that?” he asked.
“Let’s just say I updated my wardrobe a bit,” she said. “You mentioned wanting to see more cleavage, right?”
“I mentioned wanting to see you naked and in underwear, but I guess I’ll settle for cleavage,” he said.
She sent him a laughing smiley face and texted, “You’re so mistreated and neglected.”
“I am,” he sent. “I show off my cock, twice now, and haven’t even seen you in your underwear.”
She didn’t reply to him for a minute, and he began to mildly panic thinking he’d crossed a line.
“Now you can’t complain,” she sent, followed by a picture.
He smiled when he saw it. She was sitting at her desk, but had opened her blouse up and was displaying her lacy white bra covering her massive breasts.
“Did you just take that?” he sent.
“No,” came the reply. “It’s one I sent to Chase the other day after you got me all worked up and horny. Are you hard?” she asked.
He chuckled, looking down at his semi-erect cock tenting his pants.
“Getting there really quickly,” he said.
“Prove it,” she replied. “Pics or gtfo.”
He laughed and thumbed through his pics, looking for one of his dick that he’d sent to Jessie. He selected one that framed his cock nicely and didn’t make it look small or anything. He sent if off to Nicole without hesitation.
“God…” she sent. “You’ve made me a very happy girl,” she said. “If you hear moans coming from my office, it’s just me… masturbating constantly.”
He chuckled and sent her a laughing smiley face. “Go do some work, you lunatic,” he texted.
“Oh, yes sir!” she replied playfully.
*****
Jessie
Wednesday and Thursday were normal for Jessie. She didn’t see her boyfriend much, only for a bit on Wednesday at lunch, and Thursday evening for dinner. When she got to work on Friday though, Mr. Murphy almost immediately had her come in to his office.
“Good morning,” she called, smiling sweetly.
“Good morning,” he replied, looking up from his laptop. “I want you to walk over the top of me while I lay down. Can you start going through some boxes over there to start with?” He smiled widely at her.
“You’re the boss,” she said, returning his smile. Turning, she lifted her skirt a little teasingly and then turned, focusing on a box that had files for the current client she was working on. She heard Mr. Murphy roll his chair out from behind his desk and slide closer to her. She heard the telltale zip of a zipper behind her and smiled. Standing, she went through a series of moves in front of him. Mostly she just bent way over with her knees straight. He came up behind her at one point and knelt down, looking at her. For several minutes she held this position, standing up and looking at a file while he moved around her, almost as if he was inspecting her for something.
Then, he laid down on the floor and she moved to stand over him, her ankles touching his ears. Again, several minutes passed while he stroked his average sized erection and watched her as she stood above him. He was too excited to last long though apparently, and shot his load onto his chest, hastily moving his shirt out of the way. Jessie stepped away from him and went to retrieve a towel from the small bar built into the wall of shelves near the door and went back to hand it to him. He cleaned himself up and then went back to work as if nothing had happened.
Happy to have been able to help him, she went back to work. Her phone buzzed then, and she saw that John had texted her.
“Got that video yet?” he asked.
“I was gonna film it tonight,” she said.
“Good deal, thanks!” he replied.
She figured that the could film the video tonight, and then she could let Donna fiddle with it on her computer all day Saturday while she and Dexter were at the amusement park with Erin and her boyfriend. An idea struck her then, and she sent a message to Erin, a plan forming in her head.
*****
Dexter
That evening, Dexter went over to Jessie’s as he was told. Jessie had gone a little overboard with her preparation in his opinion. There were lights set up in the living room, shining down on the floor and couch. Jessie had her camera setup on a tripod, and it looked like she had another sitting the table.
She emerged from the bathroom and came up to kiss him, then pulled him to the bathroom with her. He looked in and saw Donna’s dark brown hair and then saw another very attractive young woman.
“Sweetie, this is Erin, my new friend,” Jessie said. “Erin, this is my Dex!”
Erin, a stunningly attractive blonde, leaned over and waved. “Nice to meet you,” she said.
“Likewise,” he replied.
“Erin’s here to help me get Donna ready for your sex movie tonight. I told her all about John and how he likes to be humiliated, and how much Donna loves your cock,” she explained.
Dex raised an eyebrow.
“You’re going to need to shave your pubic region,” Jessie said, glancing at him.
He raised his eyebrows again. “Are you serious?” he asked. Jessie nodded as he looked at what was going on. Donna was standing naked in the bathroom and Erin was doing her hair. Jessie had knelt back down and had a razor, shaving cream, and a cup of water and was gently shaving her roommate’s pubic region.
“She couldn’t just do that herself?” Dex asked.
Donna shrugged. “She wanted to make sure and get it perfect looking,” she said.
“I’m sorry you got roped into this, Erin,” he said.
“Actually, this is kinda fun,” she replied.
“I’ll leave you to it,” he said, turning to leave.
“Go ahead and shower,” Jessie said. “We’ll shave you in a second.”
“Just give me the razor when you’re done,” he said. “I’ll handle it.”
“No sir,” Jessie said sternly. “It’s got to be perfect.”
He sighed, pulling off his shirt and then pants. Glancing up at Erin, he trepidatiously started to slide his underwear off in front of the nearly complete stranger in front of him.
She glanced over and then down, smiling and looking up at him before focusing back on Donna. He chuckled quietly and stepped in, washing himself with soap and then rinsing. By the time he’d finished his shower, they finished primping Donna.
“Erin, can you grab him a towel,” Jessie said, still kneeling and inspecting Donna’s groin. “Step into the shower and rinse off your crotch,” she said, looking up at Donna.
“Don’t get your hair wet,” Erin warned.
Donna quietly did as she was told, winking at Dexter as she slid in with him. Erin turned, a dry towel in her hand but averted her eyes as he stepped out and started to dry off.
Then Jessie, ever the instigator, stood and turned, addressing Erin. “Would you mind making sure Dex is shaved clean. I’m gonna go and make sure the setup is perfect.”
“Oh,” Erin said, looking at her and then back at Dexter. “I don’t…”
“Jessie, she’s never even met me,” Dex said. “You can’t ask her to do that.”
“I didn’t ask her to give you a blowjob,” she said, handing Erin the razor and shaving cream. “She’s just shaving you. I want it perfect. You can move your junk around for her. She doesn’t even have to touch you. I’m going to go out there and make sure the setup is good and then I’ll be back to take over.”
Wondering what his girlfriend was trying to do, Dex sighed and went to stand over the towel. Erin smiled at him and then shrugged and slipped down to her knees.
“If this makes you uncomfortable, I can totally do it myself,” he said. “You don’t have to listen to my lunatic girlfriend.”
Erin shrugged. “It’s fine,” she said. “I’m a massage therapist, so I’ve seen my fair share of junk. I just didn’t expect to see it so close.”
He smiled, shrugging. Glancing down, he reached for the shaving cream and lathered up his pubic region as Donna stepped out of the shower and headed to her room to get dressed, leaving Dexter alone with Jessie’s new friend.
“Lather your testicles up for me too,” she ordered.
Dex nodded, doing as she asked.
“You sure you want to do this? My girlfriend likes to see how far she can take things sometimes.” Dex looked down with a raised eyebrow.
“It’s not how I pictured meeting my new girlfriend’s boyfriend, but it’s fine, really. Just don’t get any dirty ideas,” she said playfully.
He nodded and stood still, stealing a glance or two down the cleave of her shirt as she stood and dumped out the dirty water from Donna’s shaving and rinsed out the cup, getting more water to rinse and then putting a fresh blade in the razor itself.
“We should have used trimmers or scissors on you first,” she said. “This is gonna be a pain in the butt.”
“I can rinse and dry off,” he offered.
She shook her head. “We’re already here, let’s just get through this.”
He nodded, more than happy to let this attractive stranger near his cock and balls. She started by getting up close to him and shaving his upper pubic region, and around the edges, washing out the razor every few seconds. As she worked, he looked down and watched.
She was very attractive, without a doubt. She had a peculiar smile that turned up at the very edge, and adorable dimples when she smiled. Her hair was straight, but wasn’t too long; maybe shoulder length. Her breasts were her best physical feature though. They were large and perky, and he wondered briefly if she had larger nipples or smaller like he preferred.
He shook the thoughts away and looked down again, past his lathered groin to her cleavage. The shirt she was wearing wasn’t necessarily low-cut, it just happened to be that the angle he was standing at was perfect for staring right down it.