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 after receiving a great job offer with an investment firm. Tyler had moved to New York City to further pursue her art. Now at 28, they found themselves again brought back together in New York City after Josh took a promotion that took him to the Big Apple.
Josh could be described as a charming. This, coupled with his intelligence, lead to a very successful career. He was 6’1 205lbs and 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 5’4 120lbs.
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 6 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 10 min 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 a 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 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 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 2am 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 lead 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 was going through Josh’s mind.
Josh laid in bed that night and immediately started fantasizing about Tyler. He remembered all their 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 sun’d themselves. He could feel blood start to flowing 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 passerby’s.
He couldn’t help himself at this point. Josh traced a large vain from the base of his cock up the 8 inches to the tip. He felt the pulses 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 6:30am 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.
As she sat down next to him he blurted out, “You look amazing Ty!”
“Yea, I figured I should wear something more appropriate for tonight,” she replied with a laugh.
Josh laughed and asked her, “So what are you drinking?”
Their conversation and laughs came as natural as they always had, but there was something electric in the air between them. Josh kept staring into Tyler’s big blue eyes, like he had never seen them before. And Tyler couldn’t wipe the smile off her face as she continued to touch Josh’s back and arm every time she spoke to him.
It was now 8pm and both Josh and Tyler realized it was time for them to head out. Josh paid their tab and they began the 5 block walk back to Tyler’s apartment. They walked hand and hand in silence with both of them turning from time to time to give the other a smirk.
Tyler unlocked the door to her apartment, and even though Josh had been there plenty of times it felt different this time as they entered.
Tyler got a sense of Josh’s nervousness, so she told him, “Just to head to the bedroom, I’ll be there in a sec”.
Josh was sitting at the edge of Tyler’s bed and was started to wonder how this would effect their friendship. Would they just go on like normal pretending it didn’t happen? Would drive them apart, or would they stop being friends all together? Just as Josh was playing scenarios out in his head he saw Tyler’s shadow coming down the hall. Then, all the thoughts and doubts disappeared as Tyler rounded the doorframe wearing nothing at all. Josh did a double take he was so caught off guard.
“Figured I’d get a bit more comfortable,” Tyler said.
Josh’s eyes were glued to her naked body. He knew that Tyler had a nice body, but was not expecting this. Her perky breasts were much larger than he thought, with tiny nickel sized nipples. Josh could see the definition in her obliques as his glance went south to her nonexistent pubic hair. Josh was absolutely stunned.
The trance Josh was under was interrupted by Tyler’s voice.
“Your turn,” she said with a grin.
Josh stood up and removed his shirt. Tyler was watching intently as he removed his pants as she could see his bulge throw his boxer briefs. Then as he slid down the briefs Tyler finally got a look at his thick 8 inch cock, as it spilled over the elastic waistband.
Her eyes lit up, “Holy shit, it’s perfect,” she said while sliding her hands down toward her pussy.
Tyler could feel herself getting wet now at the sight of Josh’s muscular body and gorgeous cock. Josh’s cock was becoming more erect and he began slowing playing with himself as Tyler came and sat next to him on the bed.
As they started to kiss, Tyler removed Josh’s hand from his cock and took over the stroking duties. She could almost feel the blood pulsing as she gripped his veiny shaft.
Josh worked his hands between Tyler’s legs as they continued to make out, and he felt how wet she had become. He slowly used his fingertips to trace up her now soaked pussy to her clit.
Josh began to slowly massage her in small circles but Tyler then pushed him backward onto the bed with his feet still on the floor.
She kissed her way down his neck, to his stomach, and then ran her tongue from his belly button to the stem of his cock. Tyler looked up and made eye contact with him just as she put her mouth around the head.
Josh put his head back in pleasure as he felt her warm mouth wrap tighter around his shaft. As Tyler sucked on Josh she also stroked him with her hands, which caused Josh to let out small moans and grunts as she worked him.
Tyler took Josh’s cock out of her mouth and turned her attention to his testicles. They were smooth and Tyler enjoyed the way they felt as she was putting them in her mouth, sucking them lightly.
Then she pushed Josh’s thighs back farther and exposed his freshly shaven hole. She slowly dragged her tongue from his balls down to his asshole and began working it in circles.
Josh let out an “Oh my god!” as he had never felt anything like this.
This encouraged Tyler who continued to rim Josh and then started pushing her tongue inside his hole. Josh couldn’t help himself, the pleasure was overwhelming, he grabbed a hold of his cock and started stroking.
He couldn’t believe how good he felt. Then Tyler’s tongue came away from his asshole and she emerged between his legs with a big smile.
“You ready for more?” she asked.
“Yea…I definitely am,” replied Josh.
Tyler then got up and went to her closet leaving Josh on the bed still on his back.
Josh saw her reach for something, and when she turned around she was holding a realist flesh colored dildo, and lube. The dildo was around 7 inches and not nearly as thick as Josh. But he was intrigued as he saw the large head and veins running down to a set of testicles.
He’d never used anything like this on himself he thought.
Tyler walked back to the bed. “Turn over and get on your knees,” she said playfully.
Josh did as he was told. He put his chest on the mattress and pushed his butt up in the air. He felt so exposed and vulnerable. Then he felt the sensation of the room temperature lube hit his crack and begin dripping down. This was followed by Tyler’s finger working the lube around his asshole then pushing it gently inside with a single finger.
Josh’s body quivered as she entered him. Tyler applied more lube to the dildo itself. She twisted while stroking it, in order to completely cover the toy in the slippery substance.
During the antisipation, while Josh sat there on his knees, he began stroking himself again. He could feel a bit of precum at the tip, which he rubbed around his engorged head with his fingertip.
Just then he felt the large head of the dildo pressing against his asshole.
Tyler advised him, “Just relax”.
He took a breath and she pushed it slowly. The head was larger than Josh had expected, and he could feel himself getting stretched.
Tyler was struggling to get it inside him momentarily.
Josh let out an “Agh!” as his tight asshole fought back against the toy.
Tyler pushed a bit harder and suddenly the head popped inside him. Josh gasped loudly with pleasure, as the slippery toy entered him.
Tyler began worked the dildo in and out of him in short slow strokes, each time getting a little deeper. Josh started to moan with every push inside him.
Then he began to push his ass back into the toy as if to want more. Tyler was verbally encouraging him as she fucked him.
She told him’ “Yes yes, just like that,” and “Mmm, take it Josh”.
He began to lose control as he felt her gently kiss his back. Then he felt the rubbery testicles on the dildo hit his butt cheeks.
Tyler stopped trusting it into him and told him, “Good boy, it’s all in you”.
Josh was sweating at this point. He glanced over his shoulder at Tyler and saw a deviant smirk on her face.
Tyler then ordered Josh, “Let’s have you flip back over”.
Very slowly Tyler slid the dildo out of him making a sloppy suction sound as it left his hole. Josh flipped onto his back and Tyler reapplied lube.
This time as she pushed it into him it slid in with much less resistance. It wasn’t long before she was using the entire length of the toy to penetrate Josh. He was moaning and grunting louder now as she picked up the rhythm.
This turned Tyler on even more. She grabbed a hold of Josh’s cock and started stroking him rapidly. Tyler continued fucking Josh while jerking him furiously. Josh was in total ecstasy. He could feel himself getting close to release when Tyler locked eyes with him.
Cum for me!” she demanded.
They held their gaze as Josh began to tense up.
Then Josh moan loudly, “Ugh ugh,” as he let out a huge stream of cum.
Tyler wasn’t prepared for it, and it splattered right between her gorgeous breasts.
The next, “Ugh,” from Josh, produced another thick load which Tyler tried to catch in her mouth.
This time it struck her on the cheek and ran down her neck. Josh continued to spirt cum, as each stream contained less and less fluid, that Tyler eagerly took in her mouth. Then with a final shudder, Josh had finally been drained.
Tyler left the dildo inside him and laid her head on his chest, while she still covered in Josh’s cum.
They laid silent for a moment before Tyler finally said, “That was amazing”.
Josh who was still catching his breath at the time responded, “You have no idea,” with a laugh.
A few moments later Tyler sat up and looked at Josh, “My turn,” she said.
“Don’t you want to get cleaned up?” Josh asked.
Tyler still had cum dripping down her neck and chest.
“Nope,” she replied with a playful grin.

Source: reddit.com/r/eroticliterature/comments/rm6iwm/first_pegging_experience