7 Jul 2017
Toby's Sexual Journey - Chapter 2 - "His First Time"
- 0 Comments
- 1072 Views
8 minute read
Toby was adamant that his days of wanking followed by sobbing were about to come to an end. The only way to stop his semi naked step mother entering his wank bank at the crucial time was to have sex with an actual real woman. His new job at the local paper felt like a natural turning point in his life and Amber, his non old, non fat and non ugly colleague, seemed like the perfect person to end his self love misery. Today was the the day he would get the ball rolling on that mission by complimenting her on her journalism.
Amber was looking particularly sexy today in her ill-fitting blue blouse which showed the outline of her bra. Her tits were on the big side although a little saggy for a women of 25. Luckily for Toby he liked saggy, saggy was good. Toby peered over his computer monitor watching Amber lean over the photocopier. Her creamy white cleavage bobbed slightly as she struggled with the print settings. He began to imagine her blouse bursting open with the weight of her tits and them bursting out in her red bra. Suddenly his fantasy was interrupted by flashbacks of seeing his step mother's ample breasts in a lacy white bra all those years ago. He lept out of his chair and rushed to the toilet, hoping nobody noticed the mild protuberance forming in his trousers. They didn't.
"Have you been crying?" asked Sheila as Toby exited the bathroom red eyed. "Em, no, I...I.. was eating chili Doritos and rubbed my eyes while I had Doritos dust on my hands" was his inventive response. Sheila clearly bought it. "Oh you poor thing, let me have a look". Sheila was in her final year before retirement. She was 63 and had been at the paper for 30 years. Her last good article was 29 years ago. She reminded him off Deborah Meaden from Dragon's Den but with a fatter face. Where she most resembled Deborah was in the chest area, she also had huge knockers. These were now being pressed against Toby as Sheila inspected his eyes. She blew on them, "how does that feel?". Thinking she was referring to her massive tits pressed against his chest Toby replied "a bit awkward if I'm being honest". "Awkward? What's there to be awkward about?" replied Sheila "I'm clearing the Doritos dust away, not that I see any, you must have gotten it all out". Relieved Toby chuckled "oh you meant how does you blowing on my eyes feel". "Well what did you think I was talking about?" responded Sheila. Before Toby could invent another answer the penny dropped with Sheila as her eyes pointed down to where her chest met his. Toby gulped. They silently peeled away from each other and sat at their respective desks.
Later that afternoon Amber was at the water cooler downing a freshly poured glass of ice cold water. A bead of water trickled from her mouth. Toby was transfixed. He snapped himself out of his lustful stare and went to approach her. This was it, he was going to give her the compliment that would eventually lead to mind blowing non imaginary sex, he hoped. His palms were sweaty, he was breathing heavy, there was a slight tremble in his voice when he said "Hi Amber". "Hey Toby" said Amber. "I just wanted to tell you that I think you're articles are very good" uttered Toby nervously. Amber smiled and said thanks before walking back to her seat. "The seed has been planted" thought Toby " my sexual flower is about to blossom".
As he turned to return to his desk he bumped into Sheila. For the second time that day her massive tits were in contact with his chest. This time Toby noticed that the top two buttons were undone and some cleavage was on show. Immediately Toby thought that she had bumped into him on purpose, Sheila had the hots for him. He couldn't help but stare at where her tits stretched from the sheer weight of them. Sheila looked down at the same spot and close to a whisper said "well this is awkward". Toby tried to side step out of the way but Sheila went in the same direction, her tits never breaking contact from him. "Oh, this is very awkward" she said in a now obviously seductive manner. Toby could now feel her nipples against him as they hardened and grew into his chest. He gave a quick glance around the room and saw that everyone was too busy with their work, or Facebook, to notice the sexual tension brewing two feet from the water cooler. He thought their lack of observation skills didn't bode well for their journalism but his mind quickly returned to the now heaving large breasts pressed against him.
"Excuse me Sheila, I need to pass" said a nervous Toby. "Oh you pass alright" replied Sheila in a breathy tone, "with flying colours". "No, I need to get passed" replied Toby knowing fully well that that was meant as an innuendo. He didn't quite get what the innuendo meant only that it was an innuendo. Sheila moved to one side slightly giving him enough room to pass by but not enough to avoid brushing against her tits as he did so.
Toby wanted to follow up on his earlier compliment to Amber but his encounter with Sheila had left him flustered. He stared at Amber as she rummaged in her handbag. Her wobbly tits were hypnotic. His line of sight, however, was interrupted as Sheila walked by. His gaze followed her, her giant ass swung from cheek to cheek as she walked. Her VPL was mesmerizing. Suddenly Shields' head turned and to her delight caught Toby staring at her fat ass. She disappeared into the disabled toilets. Before the door closed a hand appeared beckoning Toby. He reassured himself that, as per usual, his co-workers were oblivious to anything taking place in the room. He reasoned that the Amber plan was a long term strategy while the Sheila option was going to have an immediate pay off. He darted to the disabled toilets.
Once he stepped inside, Sheila slammed the door shut and locked it. "30 years in this fucking place and I've never once had an office fling or anything remotely like one. I don't want to retire without so much as a sneaky fingering" said Sheila raging with lust. "OK" said a sheepish Toby. Sheila turned around and hiked up her skirt revealing white stockings and big white cotton knickers. "You like staring at my fat ass boy? How'd you like to fuck it?" she snarled. "Well, em, I, ah..." fumbled Toby. "Fuck my ass" she demanded. She reached her arm back and unzipped Toby, she pulled his rock solid but small cock out. "Put that in my ass now". Toby said nothing. He pulled her knickers to one side, then parted her cheeks with both hands. Sheila grabbed his cock and guided towards her squirming asshole. "This should fit in no bother". Before he knew it Toby's slender cock was sliding into Sheila's massive hole. He gyrated slowly at first, building up speed as his confidence grew. Soon he was pumping her ass, smacking his balls against her cheeks causing a ripple effect. He swept his right arm around to Sheila's hairy pussy. She placed his fingers on her clit and he began to rub it. Sheila opened her blouse and pulled down her big white bra until her massive tits flopped out. She placed her two arms against the wall as she bent forward. Her tits swung and giggled as Toby pounded her ass. "Fuck me hard, fuck my ass hard" she gasped. She began to shudder, her chubby body shaking all over. "Fuck, I'm cuming, I'm cuming" she said in a muted squeal. Her body still trembling she sat on the toilet. She took Toby's cock in her hand and feed it into her mouth. She fitted it all in at first.Then she ran her lips to the tip. She flicked her tongue on his bell end. It glowed pink and grew to a throb. Toby grabbed her hair as his whole body stiffened. "Dear lord fucking Christ almighty" he yelped as a surge went threw his body and he shot an ungodly amount of semen into Sheila's face. Spurt after spurt smashed against her face, on her chin, her lips and in here eyes. He shook as he whispered "my god" repeatedly. He tucked himself in and Sheila told him to go out first and she'd follow once she get his jizz out of her eyes.
Toby sat at his desk in shock at what just happened. He finally lost his virginity. It was sex, sex with a big fat ugly soon to be pensioner, but a real woman all the same. And his step mother didn't enter into his head once. At least his theory was right. Soon Sheila exited the toilet, her eyes reddened. Amber spots her and asks if she'd been crying. Sheila thought for a moment and then answered. "No, I was eating chili Doritos and I rubbed my eyes with some Doritos dust still on my hands.
To be continued.