James Pays A Lesbian Couple For Kinky Sex {MFF, Escorts, Anal, Pegging, First Time}

*A commissioned story*

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**Double Seduction at the Bar**

Friday night got interesting for Chloe and Amber when a large man walked into the bar. He was tall, at least 6’1 with a powerful build to his body at 42. His arms and legs looked strong but he enjoyed life with a larger gut. That never bothered the man as he tried to stay in decent shape. The most distinct feature of the man was his large beard. It was long with thick strands of hair hanging from his strong chin.

As he ordered a whiskey neat from the bar, the man stroked his beard pondering. Chloe was already watching the man since he entered but had to point him out to her girlfriend, Amber. They were dating but were bi-sexual individuals. Amber fanned herself when looking over to see the new patron of the bar was so sexy.

The girls got in his field of view while sipping from his glass. They started dancing together trying to be sexy in front of him. The taller blonde woman with the pixie haircut was Chloe. She was about 5’5 with an athletic build at 20 years old. Her perky 34C breasts were covered by only a sexy black bralette. Down below Chloe was wearing a matching mini skirt with a pair of ripped stockings underneath. When she bent forward, the man at the bar was able to catch a glimpse of her dark red panties.

Beside Chloe was her shorter girlfriend named Amber. She was a brunette with long hair that reached almost to her thick ass. The brown hair rested just above her black thong that was pulled high over her hips to show out of her tight black shorts. Her sheer white top showed that she was wearing a matching bra. While the dents protruding from her breasts were a clear indication that she had pierced nipples hidden under the bra. Amber was thicker but still in good shape. She was also the younger and shorter one of the two, being only 5’2 at 19. Her tits were nearly identical to Chloes besides being smaller 32C’s and pierced through the nipples.

Their slutty dancing got the man’s attention so he sent them over a couple of drinks from the bar. That was an accepted invite to come over. Chloe sipped her drink while guiding Amber to the bar to meet the mysterious man with the other. They sat on opposite sides of him before he turned to the blonde, who was clearly the alpha in the relationship.

“What are your names?” The man asked before introducing himself, “Mine is James if you were curious.” He was smooth as he spoke to them confidently.

“I am Chloe,” the hot blonde said before introducing the brunette, “And this is my sexy girlfriend, Amber.” She pointed to the girl behind him. James turned around giving her a seductive smile before returning his attention to Chloe.”

They started making small talk as they learned a little about each other. Once they get a little comfortable, he points out their piercings, “So you both are pierced girls? I see your tongue Chloe and it looks like Amber has her nipples done. I got one when I was younger myself.”

Chloe giggled as he pointed out Amber’s pierced nipples but did not see his piercings. She asked him, “Did you get your’s removed or am I missing it?”

“Wanna see it?” James asked with an evil little smirk on his face. Both girls quickly asked to see it as the man whipped out his cock underneath the bar. They were shocked to see his big dick pierced right through the tip with a metal bar.

“That must have hurt like hell,” Chloe said trying to imagine the pain compared to her hidden piercing. Without being asked, Chloe pulled her skirt up and her panties to the side to reveal her clit piercing. “I got this a few months ago,” the blonde eagerly shared when finding someone with a similar one.

“You two are insane,” Amber had said the same thing when Chloe first showed her the clitoris piercing. Her eyes were locked on James’ chrome bar though. She had only seen pictures of that kind online.

“We could take you back to our place for a little fun together but it will cost you,” Chloe told him seductively, admitting that they were escorts. They had worked as a team since starting to date a year ago. Chloe was the outgoing control freak and Amber was the easygoing sexy one who got the interest of customers.

“I knew there had to be a catch for two sexy lesbians to come over to me,” James admitted as he contemplated accepting their offer.

Chloe could see that he was on the hook so she decided to reel him in. She pulled Amber across his lap as they started making out in front of him. His boner was pressed against the brunette’s tit while watching their tongues spar sexily.

“You two are a good sales couple,” James joked as he placed a hand on each of their asses. Both were nice but Amber had more to feel on.

The threesome discussed the pricing details before James offered to drive them home. They rode in the car together while the girls kept him in the mood. He was distracted by them making out in the passenger seat. Amber was sitting in her lap while kissing passionately enough to fog up the windows. James was not upset that he had to keep wiping away the moisture from the windshield to drive safely. The show in the passenger seat was enough.

Chloe slapped her girlfriend on her curvy white ass. “Keep your eyes on the road,” the blonde teased as she tried to make it difficult for him to drive by rubbing the round mounds under the shorts. She was doing a good job but he was lucky not to be pulled over for swerving all over the road.

While they were kissing, Chloe took James’ hand and placed it on Amber’s soft ass cheek over the shorts. He started groping it while driving so he did not have to look. His cock was pressing against his jeans as he was being seduced by the escorts. James did not care if they just wanted money. He just wanted to have a good time himself.

“This is our place,” Chloe said as the GPS repeated that they had arrived. The three of them climbed out of the car as James followed them up to their apartment. He slapped Amber’s curvy ass as she got out of the passenger side door.

They were all in a rush to get to the second-floor apartment as James took the opportunity to peek up Chloe’s mini skirt. He could not wait to get them out of those slutty outfits for some dirty fun sex. At the apartment door, Amber teased him by pressing her soft ass against his boner. It was a good distraction from the girl fumbling to drunkenly unlock the door.

**Round 1 With The Girls Progresses Quickly**

“Welcome to our home,” Chloe jokingly said while allowing the others to go in first.

Chloe poured them all a shot in the kitchen before going to the bedroom for the sex to begin. James was pushed onto the bed as he sat watching them dance in front of him again. This time they were sluttier in the privacy of their own room. Chloe’s fingers grabbed her girlfriend’s high-waisted thong as she tugged it up even higher. They grinned knowing that they were teasing more than each other tonight.

“I love when she dresses like this for me in public,” the drunk blonde admitted before slipping her tongue into Amber’s mouth. The brunette started taking off the mini skirt that Chole was wearing. It hit the floor in seconds, leaving her in a black bralette and her maroon panties. The tall blonde had long slender legs that were so seductive.

They continued making out while James tugged on his erection through his jeans. Chole removed Amber’s shorts before taking off her sheer top that was not covering much anyway. Both girls were stripped down to their underwear before crawling over to James’ feet at the bed. He was impressed that they had rehearsed moves.

“Want us to suck your cock, James?” Chloe asked as she offered both of their mouths to him at once. He nodded while he watched her hand move up his leg. On the other side was Amber’s hand. They were both on a path up to his crotch.

Together the young lesbian couple removed his pants and underwear in a few short seconds. James removed his shirt, not being afraid to show his belly. Chloe rubbed her hand down his torso while Amber grabbed his stiff dick at the base. The blonde looked into James’ eyes as she opened her mouth to take in his head. James had to fight the urge to force her mouth further down since he wanted to take it slow and enjoy the night. Her tongue played with his dick piercing like it was a toy she had never had before. The daring young girl even tugged on it with her teeth while grinning at James.

“At least this one has a nice dick,” Amber said while her soft little hands played with his balls underneath.

“Why don’t you suck them?” James asked the brunette before her head slipped under Chloe. Then he perked up as he felt her mouth vacuum one of his nuts into her mouth.

She switched between each ball while Chloe started making a mess on his shaft. Saliva was running down to the brunette’s face below as she got sloppy. James was leaning back with his hands propping him up on the mattress. It was perfect until the blonde popped off his cock.

“You want a turn, Amber?” The girlfriend asked because she needed a break from the large member.

Chloe did not respond but took the cock into her mouth with ease. “She is better than me anyway,” the blonde admitted while shoving her all the way down her length. Amber did not even gag as her tongue touched his balls.

“She is highly skilled,” James teased feeling her throat open up to accept him inside. He had never had a woman do that to him before.

“Wait until you experience the rest of our skills tonight,” Chloe maniacally said while running her nails down his thighs. James was ready for anything that these sexy young women were willing to let him do. They had already stripped away any restraint he had for saving money since he wanted the full experience.

Chloe pulled the brunette’s long hair to stop her from sucking the dick. Spit trailed from her plump lips to his shining cock. The blonde kissed Amber to clean the mess from her mouth before they stood up in front of James.

Amber shoved James back onto the bed as Chloe removes her red panties. Then the taller girl crawled on top of him, mounting her pussy just above his throbbing cock. Her soft lips traced the length of his cock while he felt the pierced clit drag behind. His hands grabbed onto her hips as she let it start to slip inside her wet hole. Spit was the perfect lube to get his rod inside of her tight pussy.

“You are bigger than you look,” Chloe moaned out softly as the dick opened her up. Amber took off her girlfriend’s bra exposing her perky tits with pointy nipples. They hung down in James’ face for him to suck as she started riding from the top. Amber slipped away from the man to help please Chloe.

The brunette was on her knees bedside. Her chin was touching James’ balls as she licked Chloe’s asshole. It caused her to moan even louder. James did not mind since it made her pussy gush at the added arousal. Amber was even fondling his balls while back there. She was truly a people pleaser.

“Do you like getting your ass eaten?” James asked the moaning blonde as he felt her having an orgasm. She bit her lip while nodding her head to say she does. Chloe could not speak until her climax came to an end. Even then she was gasping.

“You can fuck our asses if you got the cash,” Chloe teased while moving in to kiss James. Before he could take in the information, the blonde climbed off his lap. She barely let their lips meet for a second before yanking them away.

“My turn?” Amber eagerly asked from the floor.

“Depends on if James wants to try anal tonight or not,” the blonde said leaving the option open to the man. He was not given much time to think before the price was given. It was not much more than he expected.

“Get that ass up here,” James boldly stated after accepting the money as a loss. At that point, he just wanted to feel it.

Amber removed her high thong and climbed into the bed in a doggy position. Her fat white ass was arched in the air with her face down against a pillow. James slapped her round cheeks a few times trying to hype himself up. Chloe poured lube on her girlfriend’s ass, making sure to coat the hole well before penetration.

“She gets a little loud during anal so don’t be afraid to stuff her face in that pillow,” the blonde warned before leaning down to kiss Amber good luck.

Chloe stood behind watching as James pushed his long dick into her tight asshole. Amber had to bite down on the pillow to take in the head before relaxing. It took a few rough minutes before she was accepting the dick inside without much resistance.

“Fuck, you are so damn tight,” James grunted out while pumping himself into her ass. His hands gripped tighter to her curvy hips.

“I love it in my ass,” Amber moaned out as she started to really enjoy the painful sensation as pleasure.

Chloe snuck back into the bedroom before James even noticed she walked away. She was wearing a hyper-realistic strap-on dildo. James didn’t even notice it as she crawled under Amber with it on. While in her ass he thought he felt something stroking him inside. That was when he looked down to see the girl being double stuffed on the edge of the bed. The moans were muffled by the girl’s kissing.

As they double-teamed Amber, Chloe removed the final piece of clothing from the brunette. Her bra slipped over her head leaving her pierced nipples exposed. It did not take long for the threesome to become overwhelmed by the erotic moment. Amber was first to have an orgasm as she tightened both of her stuffed holes during her climax. That forced James to cum deep inside of the brunette’s thick ass from the intense grip. Since Chloe’s dick was plastic, she was left out of the first round. James pulled his dick from the girl as he watched his load leak from behind. It ran down her thighs as she collapsed onto the bed to relax.

**Round 2 With The Girls Gets Interesting**

James laid back on the bed with a beautiful young lady in each hand. They needed time to recover before he could even think of going again. Chloe was eager to continue since she missed out on the orgasms. Her hand moved to his limp cock as she started playing with it.

“Want to pay for another hour?” Chloe asked since he had used up his prepaid time with them already. He was not worried about the money. James did not hesitate to tell them to keep going for another round.

“Better make it worth my while,” James teased as she moved down to suck his cock. Again she could not resist letting her tongue play with the metal bar on his crown. Amber was still recovering beside them, watching as the blonde sucked the limp dick.

Chloe took his teasing as a challenge to make his night unforgettable. It was something she typically tried anyway because of her own fetishes but this time she was really going to push boundaries. She was still wearing the fake cock while James grew stiff in her mouth.

Just as he started getting erect, Chloe gave him his first sexual test. One of her fingers started teasing around his asshole. James found it odd but did not stop her. She took that as an invitation to explore further. His asshole clenched when she pressed against it with her fingertip. The blonde laughed to herself at his quick reaction. Still, James did not try to make her quit. He wanted to see what she was attempting to do at the very least.

Then she took the dick from her mouth to get saliva on her fingers. Chloe did not say a word before continuing to blow him. James felt the two fingers pressing against it for entrance and started wondering how it would feel. It was hard for him to let them inside but he slowly tried to relax just to have the experience. It aroused the blonde that he was so open to trying butt stuff since it was clearly his first time.

With Chloe massaging his prostate, James started to find pleasure in her intrusive fingers. His cock was throbbing in her mouth. He secretly started to wonder if he could take more fingers inside but did not dare to ask. Amber was finally starting to get moving again after a long rest on the bed. Her ass was in pain but she enjoyed it mostly.

“About time you slacker,” Chloe teased telling the brown-haired girl that she needed a break. Amber rolled on top of James, taking his cock back into her creamy pussy. He laid back on the bed taking his own break as she bounced on his dick. The thick woman was so wet that he could feel it running down his balls. His cum had dried on her thighs after leaking out of her gaping asshole.

While she is riding James, Chloe returned ready to fuck her ass again. Amber moaned deeply into the man’s ear as she felt her gaping ass be spread open further. She bit down on his shoulder lightly to mask the moaning. James found her pleasure sexy while he played with her pierced nipples. The metal rings made them seem long and pointier than the blonde’s nearly matching tits.

James was enjoying getting to double team Amber again but he really wanted to get inside of the tight blonde’s ass. He was not even sure if her ass was an option on the menu but he decided to go for it anyway. The man got out of the brunette to slide off the bed. James walked around behind Chloe pretending to just want to watch them.

He wrapped his arms around the tall blonde from behind with his chin resting on her shoulder. His breath went into her ear, lightly teasing as she felt her pussy getting wetter behind the strap-on. Amber was still taking it in the ass but now muffled her moans with her face in the sheets.

James kissed the blonde’s neck as he whispered in her ear, “How much to fuck your ass instead?” Before he even finished the sentence his tip was prodding at her closed hole. Chloe playfully clenched her cheeks blocking the entrance until he agreed to pay.

Knowing he was already excited about it she hiked up the price a little higher than normal. James did not care at all anymore. He laughed at her price as he pushed the wet tip into her tight rear. Chloe sucked on his finger to keep from moaning too loud as he sodomized her from behind. Both women were taking it in the ass at the same time with James’ dick controlling the pace of both.

“Fill me up,” Chloe moaned with his finger in her drooling mouth. She could feel him throbbing deep inside of her ass.

He was already fighting the urge but her asking for it was too much motivation. James dumped his warm load deep in her butt leaving both women with a messy asshole.

“Did he cum in your ass too?” Amber asked while panting after another orgasm herself. She pushed her long brown hair out of her face to look back at what was happening behind her. Chloe had an evil grin like she was planning something.

**Round 3 With The Girls Was Unexpected**

The kinky blonde girl whispered into Amber’s ear to let her in on her plan. She wanted to have some fun with James since he was so accepting of her boundary pushing anal antics. The brunette giggled as she was told the short version of the plan. Chloe told her the most important part was being quick.

James had not even got a chance to remove his cock from the blonde’s tight little ass. She pushed him back with her butt before spinning around to face him. He was confused by the fast movements right after cumming. Amber moved quickly from the bed to grab his wrists. The thick girl had the advantage as she yanked him onto the bed. James caught himself on his hands with the small girl struggling to hold him in place.

Chloe pushed his tree trunk-like thighs up so he was forced into a doggy position. The girl applied her spit to the toy and his ass before trying to push it slowly inside. James could not take the thick toy with his inexperienced ass as he clenched himself tightly resisting.

“That is too much,” James said as he winced in pain. Then he sighed to catch his breath, accidentally allowing it some relaxation to get the tip inside. He could not believe that she was jumping from fingers to strap-on so quickly.

The sensation was oddly satisfying to James even though it still hurt. His pain caused him to continue protesting while trying to enjoy the sexual exploration. “Stop pushing it in,” the man ordered but Chloe knew he would like it once he got adjusted.

“I think he kinda likes it,” Amber said in a sexy little voice while watching his face finally stop wincing.

“I am not paying for this,” the man said while he was being sodomized by two hot young lesbians.

“Since you paid for two rounds, I guess we can let this be a special deal for the third round being free,” Chloe said, pushing the toy deeper inside. If he would have tried he could have got a discount on the whole night.

James was starting to relax because the toy had started gaping his hole from behind. It was no longer as painful. The tearing sensation had turned to a pleasurable tingle in his ass. The man had never tried butt stuff to any extent near this but found that it felt better than expected. James thought it was weird but could not help but enjoy taking it.

“He really does like it,” Amber said while pointing out that he was fully erect again. Her finger flicked against the piercing on his crown while watching it flinch.

“I never thought I would be in this position, and I really never would have guessed I would like it,” James said letting himself finally give into it fully.

“That is what every straight man says the first time,” Chloe said while feeling her pussy get even wetter from his admission to liking his butt toyed with.

“Maybe I should milk him,” the brunette said sitting beside him now that she did not need to hold him in place.

James wanted to beg the woman to milk his throbbing erection just to relieve the tension he felt down there. Chloe was pounding him from behind, getting off to breaking down his boundaries in a single night. Meanwhile, Amber teased his stiff dick with her soft fingertips as she waited for Chloe to answer her suggestion.

“I think we can milk him for a little money if he wants that,” Chloe said, slapping him on the ass. Something about the way he was being treated aroused James in a way he never felt before. His cock controlled him as he told her he would pay.

“Then I guess we can take care of you some more. Most men do not make it this far on their first night before needing to be held in bed,” the blonde teased knowing she was in control for the moment.

Amber’s soft hands started stroking his cock as if she was actually milking a cow. He was already precumming from his tiny hole. The brunette poured some lube on her hands to make it easier. That felt even better on James’ sensitive dick. She stroked it like a game while sitting with her pierced tits beside his face.

The man took one into his mouth to suck as he tasted the metal mixed with her skin’s natural flavor. He was trying to distract himself from the immense pleasure he was feeling in the lower half of his body. His legs even started to feel too weak to support himself anymore.

“This is intense,” James grunted as his knees slipped from the edge of the bed. He tried to get back on his knees to take it but he could not. “Just keep going,” he told the blonde behind. Amber could no longer attempt to milk him as flattened the erection to his stomach.

“I will be right back,” Chloe said as the toy left him gaping on the edge of the bed. Amber was showing her sweet side as she rubbed the man’s back in support of him taking it so long. James just wanted to feel it back inside.

“You did better than I did my first time and I didn’t have Chloe pounding me either,” the brunette joked as she waited for her girlfriend to return.

It was just the break that the group needed as the short-haired girl returned with water. They passed around the bottle taking sips after the long night. Once they felt ready to finish, Chole pushed James back on the bed. She stood bedside while putting his heavy legs over her shoulder. Then she started to fuck him in the ass again.

His cock perked right back up as he was stuffed. “Looks like I can get started again too,” the cheerful blonde said as she started stroking his enlarged dick.

James was fingering the brunette’s pussy that was inches from her face. She moaned lightly when starting to enjoy his fingers. Chloe noticed it and started fucking him even harder in his tight hole. Amber liked trying to make her a little jealous and she saw it coming out in the slight hate fucking she was giving to James.

“You should put them in my butt instead,” Amber moaned out in a sexy voice while looking right into Chloe’s eyes. The girls were daring each other to keep pushing it as lust filled their eyes for each other.

Chloe tried to compete as she pushed his legs apart on the bed. It caused him to feel even tighter around the toy. He was grunting harder as the blonde proved that she could test his limits too. Amber decided to up the ante.

“Want to eat my ass, James?” The slutty brunette offered while winking at her girlfriend. They both knew that there was no way he turned it down. James seemed to be down for anything tonight.

The strong man reached over his head to grab her thick hips. He lifted her up and pulled her legs over his face. When he lowered the short girl down she felt his tongue teasing her asshole. She bit her lip while grinning at Chloe. Amber had taken the lead back from him. She kept stroking him with his tongue exploring in her ass. Her favorite move he attempted was giving her a tickling rim job.

“Amber is such an anal whore,” Chloe teased as she pulled her girlfriend in for a kiss. It was a triangle of anal play on the bed as James felt himself getting closer.

“Chloe is just jealous I am letting someone else tongue my ass,” the brunette teased back after playfully biting her girlfriend’s lip.

The blonde grabbed Amber by her throat as she started choking her. She knew what got her girlfriend turned on. Her pretty face turned red with a big smile. Chloe looked deep into her eyes as she showed her who was in control. Then she let go of her grip so Amber could start gasping for air.

“Why did you let go?” she asked playfully. Amber was stroking his throbbing dick as fast as she could. The more turned on she became the more intense for James it was. The girls were using him in their own sexual games.

Chloe grabbed the brunette’s neck again. This time kissing her while she fought for air. She felt her tongue slowing down as her body lost oxygen shortly while making out. This time when the blonde released her, Amber had no sarcastic remark. Her body handled it differently the second time it was teased.

Amber squirted all over James’ chest causing him to stop tonguing her. He lifted her waist from his face, looking down at her gushing pussy as he grunted even harder. Chloe was giving him all that she had after seeing her girlfriend squirt for the first time.

“That was new,” Amber moaned as she tried to keep stroking him.

Finally, James could take not more of the erotic night of sexual exploration. His cock erupted like a volcano as his warm seed sprayed into the air with immense velocity. The cum covered Amber’s pierced tits above his waist as he emptied everything. Getting his prostate milked for so long had caused a massive build-up. He could not stop grunting with each spurt being released from his rocket.

When it was all finished the girls watched him lay there unable to move for a few minutes. While he tried to recover from the best orgasm in his life, they started cleaning him up. Their little pink tongues licked all over his body collecting the cum. Chloe got most of it before they had him mostly cleaned.

The girls kissed each other over his softening cock for a little while before he was comfortable moving again. He could barely walk as he stood up from the bed. James settled his bill with the girls before they both kissed him goodnight.

James walked awkwardly down to his car where he sat silently for a moment. He had to think about the events that had unfolded for him tonight. Somehow he went from never letting a girl near his butt to allowing one to plow him from behind. The weirdest part for him to accept was how much he enjoyed it.

He could not stop thinking about how intense it felt when he was cumming that final time. There was so much going on but still, he could feel the faint sense of the past orgasm. A part of him wanted to go back inside to try to feel it again. The rational part of him knew that his body would not be able to take it so soon.

As the man drove home in the early morning hours, he thought about how much he wanted to try new things with the girls again. James wondered if he would be able to pay them to show him some more kinks in the future. He could feel it becoming a problem already. When he got home he went straight to the bathroom feeling like he needed to shower the night off of his body. Something inside had been changed.

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Source: reddit.com/r/eroticliterature/comments/n85d6w/james_pays_a_lesbian_couple_for_kinky_sex_mff