Holly was at work, her cubicle was orderly and her files laid out before her on her semicircular desk.
She was preparing for the upcoming conference in Bangor. Her manager had selected Holly and one other to attend to represent the state environmental team.
She was on a video conference with her co-attendee a man named Fred from the Portland office.
They discussed what would be presented, this was a conference for water operators of the state and as her department oversaw the Clean Water Act they were expected to deliver some sort of guidance to the operators.
Fred was a married man in his late 40s, clean-shaved and in good shape for his age, his wife had been ill for over a year and the strain had shown on his face, and as good of a husband as he was, he was clearly looking forward to having a few days away from his normal life.
They discussed the specifics and even worked out hotel reservations as well as transportation. Fred would take the state car from Portland and drive up north to Augusta to pick up Holly and together they would make the rest of the journey north to Bangor.
The plan was to leave on Tuesday morning and make the conference in time to have lunch and attend the after-lunch talk. Then head to their hotel to check in then return to the conference for dinner and small talk with everyone.
The conference was a 3-day affair and they planned to drive back on Friday morning.
Mark, Holly’s husband dropped her off at her office on Tuesday morning kissing her goodbye and leaving her with her suitcase to be picked up by Fred.
Holly was wearing her red suit, a form-fitting red skirt and matching jacket with a black blouse under it, she looked hot but professional, exactly the look she had gone for.
Soon Fred arrived and she put her suitcase in the back seat of the state car and got in.
The drive was not too long and the two talked shop mostly, a little about each other’s lives, but mostly about work.
Holly outranked Fred although Fred had been with the state longer, Fred was one of those guys that thought he knew a lot but often proved he didn’t when he would speak, a typical know it all that knew very little but didn’t even know that.
They followed the plan, lunch and then the talk and then checking in at the hotel, each to their own rooms, then back to the conference for dinner.
Something about Fred sort of turned Holly on, not his mind for sure, but he was tall and he moved well, a physical confidence of sorts. Holly figured he was well-hung.
They left the conference early, and headed back to the hotel.
“I am going for a swim, care to join me?” Holly said as they drove to the hotel.
“Maybe, it’s been years since I went for a swim,” Fred said as they pulled into the parking lot.
Sure enough he did join her, in fact he got to the hotel swimming pool before she had time to change even, he called her saying he was at the pool and she told him she was changing and would be there soon.
As she approached the pool and dropped her towel, showing off her yellow tight bikini Fred said, “Wow, Holly nice ass!”
Holly was shocked, but out of habit thanked him and got in to the pool. They spoke about the conference a little and then Fred swam over to where Holly was leaning back against the pool edge.
Holly didn’t move back as he approached and soon he was standing in front of her, one arm over her shoulder holding on the edge, while his other hand below the water rested on her hip.
Holly didn’t move away, she smiled, and they continued to talk about work related issues. Until Fred leaned close and whispered “You have an amazing body Holly, do you mind if I touch you?”
Holly said nothing but smiled and put her head back, this Fred took as a yes and moved his hand from her hip down and over between her legs, softly touching her pussy over her bikini-covered crotch.
Holly opened her legs, but also quickly looked around, they were in fact alone at the pool, she put her head back again as Fred began to slide his hand into her bottoms, touching her newly shaven snatch and oh it felt good.
Holly had come to learn that a man who is good with his hands is good with his cock, and Fred was doing very well.
No one mentioned each other being married, no one said anything, the moment had become silent, she felt his cock now hard and tenting his swim shorts brushing against her stomach, Fred was tall and he did indeed have a large cock.
They decided to take this indoors as other guests started entering the pool area.
Back in Holly’s room, her bag barely unpacked, window blind not yet closed, her red suit in a pile on the floor, and her phone charging on the bed stand, she stripped off her bikini as she walked to the bed, Fred following and walking out of his swim shorts, his hard cock now semi hard from the walk to the room.
Holly lay back on the bed pulling Fred down on top of her. “This stays between us Fred, seriously no one can find out.”
Feed grunted a sort of yes as he began kissing Holly’s neck.
Then Holly’s phone rang, she looked over at it, it was Mark, she had to answer it, she told Fred to be quiet and answered the call.
“Hey baby,” she said.
“Hey sweetie, I called but no answer earlier, are you ok?” Mark sounded concerned.
“Oh I am fine I was swimming at the hotel pool.”
Fred starts working his way down Holly’s naked body with his lips and tongue.
“Wonderful, did you have a good drive and how was dinner?” asked Mark in his typical caring way.
“The drive was OK, but you know I had to ride with Fred and oh God how he bores me to death,” she said, causing Fred to playfully bite at her nipple.
Holly put the phone on speaker and then resting it down on the bed she grabbed Fred’s head with both hands and pushed him down so his face was between her legs.
“Oh I am sure he wasn’t that bad to ride with dear.” Mark said on the speaker.
“He is a very oral type of guy, oh, uhhh, very oral,” said Holly as Fred licked her swollen clitoris.
“Ha so he talks too much,” said Mark missing the point as he usually did.
“Uh yeah, right there, uh honey, uh what did you, ohhh what did you do this evening?”
Mark hearing now obvious sounds of pleasure “Holly are you ok, you sound, well, a bit turned on.”
“Oh sorry baby, I am masturbating, sorry just thinking of you and you know how I get.” She lied.
“Oh wow, that sounds fun, I wish I was there with you,” Mark said most honestly.
Fred was now fingering Holly with 3 fingers while licking her clit.
“Baby, ohhh yes, I think I need to say goodnight I am, fuck yes, really into myself at the moment,” said Holly breathlessly.
“OK sweetie. I love you have fun!” said Mark a half a second before Holly hung up on him.
“You naughty man, now show me what else you can do,” said Holly in a sexy yet commanding voice.
Fred lifted her up, holding her and turning to put her down on the TV stand and mini fridge desk thing. Then holding her legs out he plunged in his hard huge cock to her wet wanting snatch.
It slid in easy enough but still felt tight to Fred, his wife’s pussy had been much looser and during her long illness had not wanted sex, so Fred was in pussy heaven for the moment.
Fred fucked Holly like that for a moment then turned her around, and put her feet on the hotel carpet, bending her over the desk like thing and grabbing her hips he worked his cock into her.
Fred being so tall and Holly being so short, Fred had to bend his knees to get the right level behind Holly but once he found that level he let loose, fucking Holly like a jackhammer, shaking the whole room it seemed by pounding Holly’s pussy so hard.
But the very long time since Fred had fucked, plus the hotness of the situation got the better of him and suddenly he was over the point of no return.
Fred tried to say “Can I cum inside you?” but all he got out was “Cum!” as he slammed into Holly one last time, filling her with his pent up sperm. The orgasum shaking Fred so his legs shook and he accidentally pulled his cock out as he was shooting his mega load, it came out all over Holly’s back and some even made it up into her hair.
He then stumbled backwards and sat down on the bed behind him. Leaving Holly still bent over the desk-like thing, her face sideways and a short look of “That’s it?” came to her face, but she kindly replaced that with a smile.
“Thank you Holly, you have no idea how much I needed that,” said Fred as he worked to catch his breath.
Holly stood up and felt his load dripping from her cunt and her back down her ass cheeks and inner thighs.
Fred gained his breath and put on his swim trunks and got his towel. Holly laid down on the bed watching him thinking *Guess I won’t be getting off tonight.* as Fred walked to the door.
“So see you tomorrow then, we have the presentation to do at 11,” said Fred as he opened the door to the room.
Holly laid back on her bed, dang she needed release! She reached for her purse where she kept a small vibratory device she called her “Office assistant” mostly used at work for those moments when hormones were stronger then patience.
No purse. “Uhhhg” she muttered, she had left her purse in the car, begrudgingly she put on her Terry cloth robe she had brought with her, naked and cum covered below it, and grabbing her room key card she went out to the parking lot to get her purse and her “assistant” to finish what Fred started back in her room.
As she got to the car, she was surprised by a voice next to her, a man in a pickup truck was parked next to the state car.
“Hey, thanks for the show, sexy,” said the man sitting in the truck.
“What? What show? Are you speaking to me?” said a confused and surprised Holly.
“Yeah you sexy, I loved the show but it ended too soon for me to finish.” He said pointing to the hotel and then pointing down to his crotch.
Holly looked back at the hotel and suddenly understood, her window blind was open, this guy must have watched Fred fucking her in the window from his truck.
Then Holly followed his other pointing finger down and looked inside down at his crotch to see his exposed cock, hard and standing tall.
“Oh well that makes two of us that didn’t finish!” said Holly still annoyed at Fred for being so fast to cum.
“Well sexy, maybe we can help each other out then,” said the guy stroking his cock and leering at Holly.
Holly had seen worse, and anyway it was dark out here in the parking lot, she knew she wasn’t about to invite this guy who jerks off in parking lots into her room, that was for sure, but his passenger seat looked clean enough.
Holly smiled and said, “Tell you what, you make me orgasm and I will make you cum so fucking hard.”
The guy was now the shocked one, half expecting this lady to pepper spray him, she was now walking over to his passenger side after saying what she had said.
Holly got in, and spread her legs, her robe spreading easily showing off her shaved snatch. “Now get me off Cowboy!” she said, no idea why she had said cowboy but it just seemed fitting.
The guy leaned down and immediately started licking her pussy, lifting one leg up so he could get his whole bearded face into her.
And did he lick! He sucked on her clit, he licked it he tongue fucked her, and he didn’t stop, he didn’t come up for air, he just worked Holly’s soaking snatch like a professional.
And soon the results came, in a huge rush of pleasure. Holly finally got off, she grabbed his head and rode it hard like an amusement park ride until her pussy was literally too sensitive to take any more, then she pulled his head back and away from her throbbing swollen pussy lips.
“Liked that didn’t you,” he said with a confident grin that showed his missing teeth.
Holly nodded yes, still shaking from waves of pleasure, and thinking how could this goblin of a man have such great technique?
The man grinned more and sat back stroking his cock and said, “Deals a deal sexy lady.” Pointing at his cock.
It wasn’t big, it wasn’t even long, it was a little below what Holly considered average even, and lowering her head to his cock, it smelled horrible!
But a deal was a deal and his hand was already wrapped in her hair and pushing her down, she opened her mouth and took the hard yet stinky cock into her mouth, hoping to suck it clean or at least get him to cum quickly.
She worked his cock, she sucked, slurped and licked it, and she was surprised that he didn’t cum immediately, she had made bigger men cum twice as fast with this style of sucking, but he held on, his cock was hard as a rock but refused to cum.
Holly knew what she had to do, she begrudgingly moved over and straddled him, sliding his small cock into her well-licked cunt, it went in so easily. She had to look down to make sure it was all inside her.
It was, and she began to ride it, she rocked back and forth and slid up and down on it, she pumped it with her vaginal muscles and reached back to stroke his balls even.
He kept trying to kiss her, but his toothless smile and cigarette breath was awful, she avoided his mouth as much as she could as she rode his cock.
She opened her robe to expose her breasts to him, he licked and played with them and that saved her from having to kiss him anymore.
She bounced on his cock for what seemed like forever!
“Cum, come on and cum for me!” she said in desperation. To that he put his hands around her neck, and squeezed.
Holly was scared now, this stranger was literally strangling her as she rode his cock. He whispered “You little slut, you are going to pay!”. Holly was shaking now as his grip increased around her neck and she began to see spots, but noticed his cock was swelling now.
And sure enough as he whispered “I could fucking kill you whore!” his small cock exploded inside her, she felt his cum shoot into her Ike a pressure washer!
Immediately his grip relaxed on her neck and she felt his hands moving away from her neck, he now held her breasts hard as he continued to cum inside of her.
Soon he was spent and pushed her off of him into the passenger seat. “You fuck good sexy,” he said as Holly covered herself with her robe and reached for the door handle.
“Thank you” Holly stammered as she got out of his truck and slammed the door, walking quickly away from his truck to the hotel doors.
She heard his truck start and drive away as she opened the hotel doors and walked inside.
Soon back at her room she laid down on her bed, now very covered and full of cum from two different guys and wondering if the second guy had left marks on her neck.
Holly jumped up and ran to the bathroom, dumping her robe and looking intently in the mirror in the bathroom, no, no marks, thank God, she thought as she looked carefully at her neck.
She ended up getting to sleep around 3 am that night.
Holly woke early for breakfast in the hotel restaurant, as soon as she sat down Fred showed up and sat with her, she rolled her eyes and acted normal.
They went over last moment changes to the speech Holly was to give and worked out some answers for questions surely to be asked by the conference goers.
After breakfast Holly we to her room to shower and get dressed for the conference, and as soon as she stepped out of the shower there was a knock at her door, she peeped through the peephole to see Fred standing in the hallway.
She let him in, Holly was wrapped in a towel and walked into the room Fred close behind her. “What do you want Fred?” she asked dismissively.
“This,” he said pulling her towel off of her, Holly now naked turned and looked slightly angry.
“Fred, look last night was a mistake,” she said as kindly as possible.
Fred pulled his pants down and began stroking his hard cock “Come on Holly give me another shot.” He begged.
Holly looked down at his amazingly huge cock, thinking maybe last night was a fluke and maybe he will preform better this time.
He was not hard, and she was horny, although she was always horny. And like clockwork, her phone rang, it was Mark saying good morning and wishing her luck with her speech today.
As Mark spoke Fred turned Holly around bending her over her bed, fingering her as she spoke as casually as she could, Mark not noticing anything odd, she held her voice calmly as Fred rapidly replaced his fingers with his huge cock, sliding into her.
Fred started fucking Holly, slowly at first, as Holly spoke to Mark. Holly having to put the phone on speaker again and lay it on the bed next to her head as Fred began loudly fucking her from behind, the slaps of him against her as he entered her over and over again.
“What’s that sound sweetie?” asked Mark.
“Oh, oh that? That I am just, oh, beating some dust, uh, uh out of my suit jacket.” She managed to say mostly normally.
Mark said, “OK sweetie, sounded like something else, you know?”
“You have such, uhhh, a dirty mind Mark,” said Holly now clearly loosing control as Fred was now back to his Jack hammering.
“Ha, yes sweetie I do, well what else do you have planed for the day?” Asked Mark innocently.
As he asked that Fred gripped Holly’s hips and pushed extra deep as he shot his load, again only achieving at best 2 minutes inside her before blowing his load, this time filling Holly’s cunt completely.
As Fred then pulled out, Holly said, “Hey baby, I need to get going, thanks for calling and I love you.”
Mark said he also loved her and hung up as Fred was walking to the door.
Once again leaving Holly dripping cum and no release of her own.
Holly avoided Fred most of that second day and even ended up having dinner with a couple of the water operators she knew from years ago to avoid Fred, she didn’t want to become his “Conference bitch” and anyway being his superior she needed to keep him below her, or rather needed him to know he was not special to her.
But later that night, Fred came knocking at Holly’s hotel door, she was a little drunk from dinner with the operators and they had been very flirty, she was horny and as she let Fred into her room she said, “This is the last time Fred, I mean it. No more after this.”
Fred entered her room, already hard and his hands all over her, his fingers quickly slipping into her cunt, and she instinctively went down on her knees and began to suck Fred’s cock, he held her head and fucked her mouth for a moment before pulling her up and pushing her onto her bed, face down.
Fred quickly got between her legs and once again Jack hammer fucked her for about two minutes then pulled out and unloaded his cum all over her ass cheeks.
Holly ended up calling Mark to come get her early on Thursday instead of staying one more night, as she had seen that scary small cock strangling guy in the parking lot of her hotel again the next night and didn’t want to see how far his strangling fantasy might go. She also didn’t want to share a ride back with Fred who would surely end up in her mouth again and she was trying to stop that from happening any more.
Fred texted Holly for awhile after the conference seeming confused about their relationship, thinking they were a thing. Holly mostly ignored such texts and eventually had to speak to him by phone saying “Look you work for me. I am not your girlfriend, we made a mistake once. Let’s not make it into a larger mistake.”
That sort of worked, but Fred still didn’t grasp it completely and often remarked on their “Weekend together” as he now called it.
Luckily Fred worked in the Portland office and Holly worked in the Augusta office, so they rarely crossed paths, but even so Holly was worried he might start telling other coworkers about it, she figured she could always deny it, but still he was just not getting the hint.
What Holly didn’t know was that Fred had made a video using his phone, a video of him fucking Holly. A video he would soon use as blackmail.
