Friends With Benefits

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Josh and Tyler had been friends since middle school.  From there the bond between them only grew stronger as they went through high school and then college together.  After college, Josh moved to Nashville when he received a great job offer with an investment firm.  Tyler had moved to New York City to further pursue her art.  Now at twenty-eight, Josh found himself back together with Tyler in The Big Apple after taking a promotion.Josh could be described as charming.  This, coupled with his intelligence, lead to a very successful career.  He was six-foot-one, two-hundred-and-fifty-pounds, and had light green eyes.  He had a muscular build and defined jawline.  His brown hair was always neatly manicured and he usually maintained just a bit of scruff.  Josh took great pride in his appearance and continued a rigorous gym routine even after his college football days had ended.  Tyler on the other hand was more of a free spirit.  While she was very athletic like Josh, and was very much a tomboy, they differed in nearly every other way.  Tyler was five-feet-four-inches and one-hundred-and-twenty-pounds.  She was petite and her body resembled that of a lifetime gymnast.  She had an ample set of B cups, but she usually never wore a bra.  Her blonde hair was usually up in a messy bun and she rarely wore makeup.  Even with little effort on her end, she was a natural beauty with crystal blue eyes.Josh had been in New York for close to six months now, and he and Tyler had spent plenty of time catching up and sharing stories over those months.  Josh’s new apartment was only a ten-minute walk from Tyler’s.  It was just like old times, and they both enjoyed having their best friend so close to confide in.One night after work they were sharing laughs over beers at the pub they frequented.  Josh had recently started dating Lauren, who he met while grabbing his morning coffee.  It had been nearly a month now and Tyler was curious how things had been going.  “So?” she asked, prodding Josh to tell her more about him and Lauren.  Josh laughed, “Things are going well with her,” he said, “It’s only been a month, but I think there’s potential there.”Tyler almanbahis şikayet smirked, “How’s the sex though?” Josh nearly spit out the sip of beer he had just taken.  “Geez, Ty, you never were one to mix words, were you?” He exclaimed.  But he continued, “It’s good, I mean at least I think it’s good.”Tyler gave him a twisted smile, “What does that even mean, Josh?” she said.  Josh shrugged his shoulders but Tyler could tell he was just avoiding the question.  “Just say it, ya pussy!” Tyler blurted out.  “Fine,” Josh said, “She’s just not as into experimenting with things as I am.”  “Was that so hard?” Tyler asked.  Even though they had been best friends for so long, they had never had an open conversation about sex like this.  Tyler continued, “So what is it that you want to try?”  Josh opened his mouth to speak but then closed it again.  Finally, he started again “Seriously, Ty, promise not to judge?” he asked.  “Josh, I’ve known you forever, I’d never judge you,” she replied.  “Ok, well I asked her to finger my ass while she was giving me a blowjob the other day,” Josh said.“And?” Tyler quickly asked.  “Let’s just say that was the end of the blowjob,” Josh laughingly answered.“There’s nothing wrong with a guy wanting his ass stimulated,” Tyler told him.  “I love anal, so it would only make sense if a guy did too,” she continued.  Josh laughed nervously, he couldn’t believe what he just told his best friend.  But he was more shocked at how she responded.  He always knew Tyler was a little more open than he was but didn’t expect this.  “I can’t believe we’re having this conversation,” he said.  “Why?” Tyler asked, “I’ll play with your ass if she won’t,” she said.  “Oh my god, stop, Ty!” Josh said, laughing it off.  “I’m serious, I’d definitely be into that, Tyler explained.  “How about this?” she continued.  “This Friday we grab beers after work, then head back to my apartment and we’ll see how it goes?” she asked with a grin.  Again, Josh laughed it off but replied, “Yea ok, Ty.”  That night they hugged and parted ways.  Josh called Lauren on his walk home and told her how he had met Tyler for drinks.  Lauren didn’t almanbahis canlı casino think twice about it as she knew they had been friends forever.  But Josh failed to disclose what he and Tyler talked bout.  That night, Josh had a hard time sleeping.  He couldn’t figure out if Tyler was serious, and finally, his anxiety got the best of him.  It was 2 am but he had to know, so he grabbed his phone.  ““We’re you serious about Fri?” his text read.  Seconds later he saw the text bubbles and a reply from Tyler.“Yup!” with a wink emoji, she responded.Josh was excited, nervous, and a little confused at this point.  His best friend who he never viewed like that was offering to fulfill his biggest fantasy.  Josh had his first experience with anal during a one night stand while still working in Nashville.  He couldn’t even remember her name, but it didn’t matter. She changed his perception of things when she used her middle finger and gently slid it into his asshole while sucking his cock.  He came harder than he ever had before.  Josh never saw her again, but the experience led him on a journey to truly discover what he loved about it.  Over the next several years he bought numerous toys to stimulate himself while he masturbated, but he could never share his desires with a woman he thought.  But now, here was his best friend, offering to make his fantasy a reality.Thursday passed without much excitement.  Josh took Lauren to dinner at the Italian place she had been wanting to go to.  After dinner, Lauren came back to his apartment.  They relaxed and watched a movie together.  Josh could tell Lauren had sex on her mind.  She had her hand on his inner thigh and making gentle circles with her nails, inching closer to his cock.  Normally Josh would have taken the hint, but tonight his mind was elsewhere.  He told Lauren, “I’m sorry, babe, but I’m exhausted from work and I don’t think that pasta is sitting right.”  Lauren immediately apologized and went into nurture mode, but Josh explained he was just going to go to bed.  Lauren gave him a kiss goodnight and told him, “Feel better babe,” before leaving.  She had no clue what almanbahis casino was going through Josh’s mind.Josh lay in bed that night and immediately started fantasizing about Tyler.  He remembered all the beach trips they had taken together and his mind started to wander.  He was picturing her slender, tan body, laying next to him as they sunned themselves.  He could feel the blood start to flow to his cock.  Before he knew it, his cock was hard as steel, as he pictured Tyler’s nipples poking through the navy bikini she often wore.  She was reclined back on her elbows and forearms watching passersby.  He couldn’t help himself at this point.  Josh traced the large vein from the base of his cock up the eight inches to the tip.  He felt the pulsing coming from his head.  He slowly started stroking but then remembered that tomorrow was Friday.  He pulled his hand from his sweats and texted Tyler.  “Still on for tomorrow?” He sent.  Shortly after he got Tyler’s response.“You know it, see you at Donnelly’s around 6,” She told him.Josh was startled at 6:30 am by his alarm, but got up like any other day.  When he got in the shower, it hit him again that it was Friday.  Josh normally kept a very structured grooming routine, but this morning he definitely made sure he followed it to the letter.  This included shaving his chest, pubic hair, and paying particular attention to his asshole.  He threw a tailored navy suit on and off to the firm he went.   Josh couldn’t focus throughout the day, and quickly realized he needed to get out of there.  Shortly after lunch, he packed up for the day and headed to the gym.  He had a great workout as he had so much pent up testosterone in him.  He sent a quick text to Tyler before getting in the shower saying, “Short day at work, prolly be there around 5 but come whenever.”When he got out he saw her response of, “5 works… I’m excited.”   Josh sat on a barstool sipping Woodford Reserve with his mind still racing.  Every time the pub door opened he felt a rush come over his body.  He couldn’t remember ever feeling this anxious.  Then the door opened and he caught a glimpse of dirty blonde hair and a carefree smile.  His heart suddenly started to race.  Tyler walked in a beautiful white sundress which was just short enough to show off her defined thighs.  Her hair was up in her normal messy bun and her makeup was minimal but Josh couldn’t stop staring.  

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