Gerry’s life was busy. Not just in the conventional sense with family, work and bills. Gerry was what is commonly referred to as ‘a player.’ If he were a woman he would be called something derogatory for sure, but being a man he was exempt from all of that kind of thing. His family consisted of his parents, who he telephoned weekly and visited monthly. There was always the usual maintenance calls for a broken email account or photos missing from a folder on an iPad. These were to be expected if you dragged two octogenarians into the 21st Century screaming and kicking. Work? Well work was work. It wasn’t exciting or even challenging anymore. All the cars he sold with high ceiling commissions, he usually hit, which mean the fun went out of it a long time ago. Occasionally he would try to sell a car a cheap as he could to the right person just for fun, or access to her knickers; but most car buyers came in pairs. Young women brought a parent or some smart arse that thought having bought a car themselves made them a fucking expert. Having them in attendance only annoyed him and made to want to take as much money as possible from them. He once came so close to saying, “If your friend here wasn’t such a wanker, I would have given you the car for free!”
He didn’t though. He took the commission and kept quiet knowing they were happy with their lot, and so should he be.
Being single, and happy with that status, he enjoyed the extra cash and ensured he maintained himself well. He hated gyms, but that was the place to find women. The gym first, supermarkets second. Over the last few years he had mastered the day time rotation of eligible females to a fine art. He knew when the try-hards were in, the ones that had let themselves go and were working out for hours and then eating MacDonalds by night. There were the pretty young things that really went for it, giving their all, looking in the mirror constantly and taking selfies with over sized phones. To him they were farcical, extensions of the Kardashians living a disposal life and either transfixed with their social media or vomiting outside nightclubs in short skirts. They were not for him. His targets were divorced mothers; the ones that knew about life, cared about their appearance and knew how to speak to a man. With a well-timed smile, or a door held open without too much drama, he knew there would be a white mark in those knickers but the time they got home.
And so Gerry’s life was one large pool of MILFS. Or MIAS as he called them. (From Mama Mia, his favourite film) ‘Mums I Am Shagging.’ It made him laugh anyway.
Last night he was with Sandra. A 40-year-old mother of two with her own house. It was in a nice part of town, clean and tidy with off-road parking. She always made an effort for him. Kids with their Dad, nice meal and then off to bed. She was a few pounds over weight with large boobs and a tattoo of a horse on her hip. He never asked why a horse, in truth he didn’t care. After sucking his cock for a while, for which she was very good, Sandra undressed to reveal her soft plump skin. If you ignored her stretch marks and the red welts left behind by her underwear, she looked great. Sex was fantastic with Sandra although she did have quite annoying rash where she shaved her pubic hair. It was a little bit disgusting but he could ignore it if he closed his eyes when down there.
There was Sally with the lazy eye that killed an erection. Mona who had hair growing in the small of her back which made him gag. Karen who had a boob reduction; a BOOB REDUCTION! What kind of woman would do that? Fucking weird that’s what it was. And then there was Susan. He had been with Susan before, twice in fact. She was great in bed, funny, paid her way and didn’t mind getting come in her hair. In fact he aimed come in her hair on purpose; marking his territory if you like. On this, her last, and fateful day, she wanted to meet on a public holiday and go to the beach. That sounded okay in principle and with picnic basket in hand they got lost in the large fortress-like sand dunes. Having found somewhere away from the madding crowd he had her strip. She was a fine site for sure. Just a summer dress, no bra, no knickers, and with a quick shimie she was au natural. They drank wine and fucked numerous times in the hot sun with interruption. It was only when she mentioned that she was a little pink on her back and shoulders did she let herself down. Sex was suddenly off the cards, as was any attention for Gerry! Why she hadn’t put on sun lotion before going out was beyond him. She felt faint, was thirsty and had a headache. Talk about a cock block! To top it off, she complained a couple of times that the seat belt was rubbing on the way home and that he was driving too fast. Not fucking fast enough he had thought. Get this whingeing pink piggy out of my earshot was his intention. And so Susan was not seen again, at least by him.
Tonight though was a new lady. She had sent him a text saying she was into anal sex. He had done this before but the girl kept complaining it hurt, which he thought was bloody obvious and should not have been a surprise to her. Regardless of her getting it wrong, he was up for trying it again.
Due to domestic issues Mandy had booked a hotel room. It was middle range which surprised him what with her probably being a house wife and all. She answered the door, having previously text him the number. Mandy looked like a 1950’s pin-up girl. Retro underwear and makeup done just so. She looked amazing. On entering the room he saw she had brought food with her, nice touch, although made at home he assumed. A little sad he thought as it would have only cost £50 or so to get something professionally made. They kissed and finally she got to her knees, a bit late on for his liking but she got there in the end.
“Undress me,” she purred.
“With pleasure my gorgeous film star.” He said, playing along noticing she had an edge of command about her voice. He liked it!
Again, as with other women he noticed her underwear had left an imprint on her white skin. She was a bit blotchy with heat and when he went to knead her boobs he almost recoiled from the sweat underneath them. He kissed her and wiped his hands on her ample arse hoping to brush away the thought, but the small of her back was wet too. This was not good at all. In fact he really did not want to fuck this pinky wet version of the Michelin Man. He felt pity for her in some ways, although how she looked wasnt his fault.
“Do you like what you see?” She said climbing on the bed.
“I have to say you are unique in many ways.” (sweaty, he thought)
This was said with a slight edge that he thought she might have picked up on. Not that it mattered, he would be out of here very soon.
“Shall we play a game now Gerry? A real sexy game?”
He felt a twitch in his cock; she knew how to use her tone of voice for sure.
Come over here my big man, let me have you..
He had never been tied down before during sex, it wasn’t his thing, or so he thought until now. He was kneeling on the padded bench at the foot of the bed with his chest flat to mattress. With arms stretched out in front and secured, his ankles tied to the bench left his cock and balls exposed. Mandy had sucked greedily on his cock and made him come very quickly. She stretched his ball sack with her teeth and rubbed warm oil into his buttocks. It was a new experience that he could get used to.
“Now, let’s put this in your mouth sex boy,” she whispered in his ear.
Before he could object a ball with straps was pushed into his mouth and the buckle secured behind his head.
“Breathe slowly Gerry, in through your nose and out your mouth, what a top boy.”
He thought this was very kinky, like in porn films where the girl was tied and……..’WHACK!’
The pain exploded across the cheeks of his bum without warning, and then another, and another. He gasped for breath, his brain trying to catch up with his circumstances.
“Now that was okay wasn’t it?”
Before he could respond her mouth was around his cock again, drawing his attention away from his now burning buttocks. She sucked hard and let her fingers circle his arsehole. This was a new sensation, a bit gay for his liking, but quite nice. Three more rounds of paddling, frantic cock sucking and fingers in his arse made Gerry drift away until he was lost. It was only when his looked to his left and saw Mandy in a mirror buckling up a harness with a large rubber cock in did he start to protest.
“Now my brave boy, did you think I wouldn’t give you what you asked for. Not many men are so confident to agree to anal on a first date!”
Gerry’s protests were misinterpreted for enthusiasm and by the time Mandy was on her sixth sphincter stretching stroke, it was hard to tell the difference between lube and Gerry’s pre-come running from his cock. So what if it was a bit gay he thought, he was in heaven and who would know?
Gerry was asked to make himself available at 12.00pm the following day in the showroom’s main office. He knew why, he had been watching the sales graph for the past six months. His ribbon indicating the number of car sales had slowly moved away from the others guys in the team. They were losers, but that didn’t distract from his self perceived greatness. Take this morning for example. Two cars sold, back to back in under two hours. The first to an elderly couple with a mobility allowance; easy sale if he was honest, the second to a pair of sisters. They wanted to share the cost of a car as they would be living together away from home. One had massive boobs that almost rubbed the steering wheel and the younger one kept flashing her crotch every time she got in and out the car. It was a joy to service them, the pleasure was all theirs, he was sure of it.
Washing his hands before going to the office, he tried to come up with a few words of gratitude and encouragement for the losers. Smiling at the mirror he really didn’t care, the £10k bonus was his for the spending. What a day; even the dull ache at the back of his balls didn’t squash his smugness as he walked into the room of smiling colleagues.
“Ah Gerry, there you are. As I was saying, we are very pleased to welcome the newly appointed regional manager to present the top sales person 2018, so a warm welcome to Mandy Davidson.
Gerry stood frozen, lost for words.
“Well done Gerry, you must have really stretched yourself to win the top boy slot!” she said smiling.
I could not stop reading this! Well done! And, hilarious 🙂
Thank NN. I read an article on Twitter last week about giving advice to male writers on how to portray women realistically. Have been on this planet some time now I felt that I had seen enough of life to be honest and meet the request of the twitter author.
Oh I loved it. Such satisfying ending. As a dominant, I was just thinking while reading: goodness someone got to whip his ass really good. Thank you for that. ?