The Start of Something Fun - Take 01

When his wife finally admitted to her affair it crushed him. They had two boys in middle school and Matt fell into a deep depression. His family and his marriage were his whole world and now it seemed everything was crashing down around him. It took him a while to figure things out and become a more independent person than he ever thought possible. His boys spent half the week with him and the other half with their mother, giving Matt time to figure out where his life was headed and if another marriage, eventually, was the right move. He worked for a large company and traveled from time to time. It was on a business trip with a group of people when he met and slept with a co-worker. This was a bit weird for Matt as he and his now ex-wife were high school sweethearts and he had never slept with another woman until now. Sex with someone different was...different, BUT great as well! He felt somewhat of a release from burden, sexually, since during his marriage the sex was missing something. It's not that it was non-existent, no, he and his ex-wife had sex on a very regular basis. Probably 3-4 times a week, but there was no real excitement to it. Matt felt like it was always the same with no adventure or even danger. Just plain old sex. This go around was exciting, new, a break from the past and he felt new life!

Along with work, Matt spent half his week raising his boys; coaching, spending time together, weekend trips, etc. He also had more down time than usual because of this new arrangement as well. He sometimes spent weeknights at the local bar, he started playing music again with some friends, and also dating here and there. The dating part was hit or miss. Not all his dates ended in sex, but more than he assumed! Matt was no greek statue; 5'-7" tall, black hair, ok shape, and he knew for a fact his cock was nothing to write home about. Hard he was almost 6"...almost. His ex-wife never complained, but she also had nothing to compare it too early on. The few woman he had now slept with didn't critique him, but he also didn't have any of them calling out to god when they fucked either. Average. Matt knew that he was pretty much average when it came to his body and fuck skills. It wasn't his fault, you get the equipment you're born with; and as for his skills in the fucking department, it takes two to tango and his ex-wife was not very adventurous with him.

Porn had always been a part of Matt's life, even from a young age. His old man kept Penthouse and Playboy mags under his bathroom sink and Matt would never pass on an opportunity to jerk off to them when his parents left him to babysit his younger siblings on a Friday night. He'd wait until they were asleep and then lock himself in his parent's bathroom, pants around his ankles as he thumbed through the magazines and stroking his hard cock to the beautiful, naked women. He'd usually cum as quickly as possible, clean up, and then head back to the family room so he wouldn't be surprised by an early arrival of his parents. This was most likely the reason he was a one-and-done kind of guy...Matt trained himself to be that way at an early age. Now single and older (he's 38), on the nights he was alone, Matt figured he could retrain himself. He would sit naked on his couch and watch porn on his laptop to see how many times he could cum from jerking off throughout the night. His record was four. Porn also brought a few things to Matt's attention, kinks if you will. He found he had a strong sexual attraction to women with perfect toes, he definitely wanted to try anal (ex-wife said NO WAY to that suggestion), and he was always turned on by watching women masturbate. That type of movie always made him hard and cum the most! Again, not being adventurous, Matt would always masturbate in private while married and there was no way he was going to suggest he and his ex-wife try it together. It wasn't until he met his first serious girlfriend (post divorce) Olivia that Matt realized there was a big, beautiful sexual world out there just waiting for him!

Olivia was a waitress at Matt's neighborhood bar where he hung out (eventually his band played there as well). She worked every Tuesday and Thursday night while she was putting herself through massage therapy school. The bar was just down the street from where Matt lived, four blocks, and Matt would go there specifically to see her. Olivia was quite a few years younger than Matt, 12 to be exact, and had a smokin' body! She was 5'-8" tall, had 38C tits, and was in great shape, especially for someone with a young daughter. She was by no means hourglass contoured, but she was in great shape with an ass that would not quit! Matt would sneak down to the bar late on Tuesday nights, after his boys were asleep, to grab a beer and gawk at Olivia, at first, but eventually started a conversation with her. After a few weeks, both Tuesday AND Thursday nights in the bar, Olivia would have a drink with Matt after her shift. They got to know a little bit about each other and Matt mustered up the courage to ask her out. Olivia said yes. They exchanged numbers and that coming weekend they planned a Saturday afternoon hike and then beers and food back at the bar.

On Friday night Matt was sitting at home with the TV on. He was scrolling through the Web, not looking for anything in particular, when his cell rang. He did not recognize the number, but answered anyway.

"Hello?" Matt said.

"Hey there," Olivia said and after a long silence continued, "Did you not put my number in your phone?"

"Oh shit! Olivia, no, I mean yes...I mean, no I forgot to put your number into my phone...yes, how are you?" Matt stammered. He was now a bit worried that she was calling to cancel tomorrow.

Olivia laughed saying, "Relax Matt...I was just calling cuz I'm bored and wanted to chat. My daughter is with her Dad and my roommate is on a date tonight. I was just sitting here studying for an exam I have next week on Tuesday. Whatcha doing?"

"Oh, just sitting here mindlessly surfing the net," Matt said.

"You watching porn?" Olivia said, "I love watching porn!"

Matt's dick was instantly hard and straining against the shorts he was wearing. Immediately he open Pornhub on his laptop. "Well, I could be if you want?" he said trying to stay cool.

Olivia laughed again and said, "Are you shy Matt? Do you not watch porn when you touch yourself?"

Matt was a bit flustered! Sure, he talked sexy when he was married and a couple of the women he fucked had talked dirtier than he experienced in the past, but Olivia was being really forward...Matt loved it!

"Of course I do! Do you?" Matt asked thinking she would be a bit bashful as well by him asking that.

"Fuck yes I do!" Olivia said, "I love watching porn when I play, either alone or with someone. What's your favorite? I really like watching guys cum...either touching themselves or blowjob videos."

Matt didn't hesitate, "I love watching women masturbate. It's a HUGE turn on for me!"

As he was talking to Olivia, Matt unbuttoned and unzipped his shorts, pulling them down to free his now rock hard cock.

"Mmmmmm, seeing a woman touch herself always makes me really wet," Olivia now purred into the phone, "Is there a specific video you like that I can watch?"

Matt wanted to ask if she was naked and masturbating, but now suddenly needed to find a video suggestion for Olivia. Luckily he had book marks on Pornhub and scrolled though his list.

"I really like anything with Riley Reid or Penny Pax," Matt said as he picked up his earbuds and put them in, giving his hands free access from the phone. He could hear Olivia clicking away on her laptop; Matt pictured her naked on the bed as she searched for female masturbation porn! Based on what he had seen of her in the bar, what Matt pictured in his mind made his cock twitch.

"Oooooh, found a good one," Olivia said and relayed to Matt what she had looked up, "Open the same video and let's watch together!"

She could hear Matt typing away as well and she asked, "Did you find it?"

"I did," Matt answered, "Push play."

They both clicked play on Matt's command and watched Riley Reid slowly stripping on a bed and eventually start masturbating with her fingers.

"Mmmmmm," Olivia again purred, "She looks so fucking sexy...I'd really like to taste her fingers right now..."

Olivia trailed off and Matt could hear her breathing become heavier over the phone. He was now slowly stroking his dick up and down, listening to Olivia's breathing. He was picturing her naked on her bed just like Riley was in the movie, slowly pumping two fingers in and out of her wet pussy. Matt's breathing became a bit jagged and heavy as well as he increased the speed of his hand.

"Are you touching yourself?" Olivia whispered, "Please tell me you're touching your hard cock right now..."

Again, Olivia trailed off as Matt heard her breathing getting heavier and heavier. He was now stroking his dick faster and could feel his balls start to tighten a bit. He knew it wouldn't be long before he shot his load. He pulled his shirt up and tried to take it off without stopping stroking, but it was no use. Matt fumbled a bit and finally pulled his shirt off and then kicked off his shorts and boxers. He was now completely naked and stroking his cock watching porn, which he had done before, but this time there was a woman on the other end of the phone doing it with him...or at least that was his assumption.

The fumbling with his shirt helped Matt edge a bit and his balls loosened, he continued stroking and finally answered Olivia, "Yes, fucking-a yes I'm stroking my cock right now...I'm not really watching the movie cuz I'm thinking about you."

"Oh my god that is so fucking sexy Matt," Olivia squealed, "My pussy is so, so wet right now! Listen..."

Matt could hear over the phone the squishing sounds Olivia's fingers were making as she fingered herself for him. Matt needed to see her so bad!

As if reading his mind Olivia whispered, "FaceTime me...I NEED to see you cum..."

Matt had never done that before! He was about to see Olivia's naked body, see her masturbating, and she would see Matt. His body was shaking with excitement!

"Oh wow," Matt said and finally asked, "Are you naked too?"

"Fuck yes I'm naked," Olivia purred, "I need to see you cum Matt! Video call me so we can watch each other...please..."

Olivia's breathing was getting harder and Matt knew he needed to act fast or he'd miss her orgasm. He clicked stop on Pornhub and hit the video chat button on his phone call with Olivia. In a few seconds he was going to see her not only naked for the first time, but fucking masturbating for him! Matt's cock was now drooling pre-cum like crazy and his shaft was glistening.

Olivia answered the video chat and was laying back into a pile of pillows on her bed; she was completely naked and Matt soaked in her body as quickly as he could before they both orgasmed together. She was completely tan, not a tan line in site, her pussy was completely shaved clean, and her hard nipples were pink and small just like her aureolas. Olivia was fucking sexy as hell and Matt was ready to erupt from just seeing her, never mind the fact she was also masturbating! Olivia now had one finger in her pussy and was pinching her nipples back and forth with her other hand.

"Let go," Olivia slightly commanded, "let me see your cock...mmmmmm, can't wait to get my hands on that tomorrow..."

That's all it took and Matt could feel his balls tighten and the cum start to rise up his shaft. He grabbed ahold quickly and said, "Fuck Olivia I'm gonna cum!"

Matt lifted his ass off the couch and shot 4 hard spurts of cum that hit his chest; a few more eventually dribbled onto his stomach and hand. At the same time Olivia's neck and chest became very flush as she announced her orgasm as well.

"Fuck, Matt! I'm fucking cumming baby!" she screamed as she thrust her hips up off the bed to meet now two fingers in her pussy. Olivia fucked against her hand as her orgasm lasted a good 20 seconds.

When she finally stopped, Olivia held her hand up to the phone saying, "You want a taste?"

Matt's cock throbbed even though he had just cum the hardest ever in his life; he wanted more and knew that he would tomorrow! Olivia then sucked the cum from her fingers, licking them clean as Matt watched mesmerized. After cleaning her fingers Olivia lightly tapped her clit with the tip of her index finger and shuddered through another mini orgasm as Matt just watched. He was looking forward to tomorrow's date.