πŸ“š michael's side job Part 2 of 1
Part 2
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FETISH STORIES

Michaels Side Job Ch 02

Michaels Side Job Ch 02

by frenchhorn1234
13 min read
4.64 (5800 views)
adultfiction

*This is the second story in this series. I would recommend reading "Michael's Side Job" before reading this story.

Michael had just finished his tutoring gig at school and was sitting at his desk, eyeing over a travel website.

"Hmm," he thought. "This one looks good."

He was looking at a European trip, and decided to use his extra money from his "side gig" to put down a payment. Michael had always wanted to travel to Europe. He thought that by the end of the school year, he might have the funds to make his dream come true.

Just then, his phone got a message. It was from Cheryl, the secretary from the Sungate Clinic. He hadn't heard from them since he got the news that Amber was pregnant (with twins) but that was three weeks ago.

"Hello Michael, we have another client that's interested in meeting you. If you can come by the clinic to do your bloodwork, we can arrange a meeting with them by the end of the month. Please let me know. Cheryl."

Michael's eyes widened. If he could get one client a month by May, Europe could be a reality. He texted Cheryl back to arrange bloodwork the following day.

It was now the end of November, and Michael found himself walking into a sports bar to meet his new potential clients: two women. This time, he was to impregnate a lesbian, if the vibe was right. He was more nervous this time than the last; at least Willard and Amber were attracted to men. He had no idea how this would work with a lesbian couple.

Cheryl told him their names and bios: Anne was 36 and a speech pathologist, and was the one that wanted to carry. Jen was 42 and a defense attorney. They had tried in vitro and artificial insemination with no success, and this was their last resort.

Michael walked up to the bar, and saw two women watching football. "Of course." He thought, and tapped one of them on the shoulder.

"Hello, Anne?" He asked shyly; he assumed it was her from the pictures Cheryl sent.

The woman glanced over at him, and gave a big bright smile. "You must be Michael!"

"Yep." Michael said shyly again, with a crooked smile. Anne was pale, thin, and had shoulder length brown hair.

The other woman who was presumably Jen was still watching the game, until Anne got her attention. "Jen.!"

Jen turned and waved, and said "want to share an appetizer? The game is almost finished and then we can talk." She looked much different than Anne. Jen had a stout body, was muscular, and had a very short haircut.

"Sure," Michael said. He was undoubtably hungry, just coming from school with no dinner.

After the game, Anne and Jen escorted him to a booth. "Sorry," Jen said. "I do love my football."

The three of them then made some small talk; Michael learned that Anne and Jen first met each other while playing together in a lesbian softball league. Both of them liked the fact that Michael was a teacher and was bi.

"So Michael, we see that with your last clients, you were able to give them twins." Anne said inquisitively.

Michael blushed. "Yep, fraternal twins. They actually run in my family. My mother was one. They say they skip a generation."

Anne and Jen glanced at each other, then Anne said "well we know that there's a chance of twins. We are actually excited about the possibility, but we'll take what we can get."

Michael then blurted out what he was thinking: "I've, well, I've never done this with a lesbian couple before. Actually, you're my second couple. I don't want this to be awkward. What do you have in mind about...how to proceed?"

Anne and Jen glanced at each other again, and Anne said "we were thinking about renting a hotel room at first. My most fertile days start tomorrow. We'll pay for the room of course. Its the one across town with a casino; we took off work for the...event."

Willard and Amber had treated him in their house, with dinner, for three nights. The whole experience with them seemed more intimate, but Michael realized that no client would be the same. And he was thinking about Europe.

"Ok, that's fine." He said. "I work until 4:00pm, and then I can meet you. So, thats Thursday, Friday, and Saturday."

"Sounds like a plan!" Jen said, and they both shook his hand, and the three of them left the bar.

Nerves were getting the best of Michael as he was driving to the hotel after school the next day. "What if I can't perform?" He thought, not knowing what to expect. Once he parked in the garage, he knew there was no turning back.

He walked to the room; Anne texted him the number earlier. His hand was shaking as he knocked on the door. "I can do this."

Jen answered, and escorted him in. "Mikey! Nice to see you. Come in."

They were both drinking; Anne was sipping a cocktail and Jen held a beer. "Want anything?" Jen said.

"Um, a beer is fine," Michael said, and Jen gave him one.

"Ah, don't be nervous kid." Jen said. "I can see it on your face. She won't eat you."

Anne chuckled. "So, Jen is gonna go downstairs to the bar, and I thought we can do it doggy. She's been prepping me, so I'm ready if you are."

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Michael looked at Anne. She was standing by the sink, wearing an extra long jersey (probably with nothing else underneath). Jen walked over to her and gave her a kiss, and then patted Michael on the shoulder.

"Give us a baby Mikey," she said as she left the room.

"I'll try!" He said, and she left.

Anne was already in position on the bed, and lifted up her jersey.

Michael got naked, and sipped the last of his beer. His nerves were fading, and he got into position. This arrangement was much different than last time, but he was feeling better about the situation. Anne was watching a show on the television, and Michael gave her a warning. "Here I go" he said, and Anne nodded.

The whole experience seemed very mechanical, but Anne's pussy was wet, and he found himself easy to thrust in her. There was no small talk, only Anne saying "let me know when you're cumming, so I can get on my back right after."

"O...Ok," Michael said, and he continued his mechanical thrusts.

In a little under 10 minutes, Michael alerted Anne, and he came. It wasn't the amazing orgasm he had with Willard and Amber, but then again, this was just a side gig for extra cash. He had to keep remembering that.

Anne quickly laid on her back and grabbed her phone to text Jen that is was over.

"Thanks Michael, see you tomorrow?" She said, and Michael got dressed.

"Of course!" He said, and left before Jen got back to the room.

On Friday, right before he left school, Michael got a text from Jen. "Hey Michael, Anne really liked you. She said you were gentle and cute. Do you mind if I'm in the room this time?"

"No, of course not." Michael replied.

"Ok, great. See you soon."

"Hmm." Michael thought. This time they would have an audience. But, Jen was cool. He figured the insemination would go just like the night before, just with Jen watching. Oh how he thought wrong...

Michael entered the hotel room, and this time both women were more affectionate toward him, like an old friend.

"Hey Mikey!" Jen said, and have gave him a big hug. She was about the same height as him, but was much bigger, and she engulfed him in her arms.

Jen then maneuvered him between her and Anne on the bed.

"So yesterday, you guys tried doggy. We thought maybe we could try something else this evening if you're up for it?" Jen said, with a bit of a glimmer in her eye.

"Um, sure, whatever you want," Michael said. "Like what?"

"Well," Anne chimed up, "maybe missionary this time, and how do you feel about Jen helping? We totally get it if thats too weird."

Michael thought for a bit, and said "actually I don't think that's weird at all. The husband helped out the last time I did this, and I actually thought that sealed the deal, so to speak."

"Ok," Anne said. "We can get started, and then see how things go. Tell us if you get uncomfortable."

They both started rubbing Michael's prick through his dress pants, and his dick started to swell. Anne then got naked and laid on her back, and Jen stood Michael up and stripped him.

Nobody talked, but Jen kept stroking him until he was ready to enter Anne. Michael inserted his dick and started to slowly pump.

Behind him, he could hear what sounded like a belt being tied and a bottle being opened....

Michael kept pumping, but he noticed Anne looking at Jen.

"So Mikey," Jen said. "I really want to fuck you while you're fucking my wife. I'm currently wearing a strap on. I'll lube you up. I cant give Anne a baby like you, but it would be the next best thing for us. What do you say?"

Michael kept pumping, and the thought actually turned him on. He was bi, and he had been fucked in the ass before. Just not like this...

"Um, sure, I guess." Michael said. "Go slow?"

"Of course Mikey," Jen said, and he then felt cold fingers message lube on his opening. Then he could feel Jen's weight behind his.

"Here it goes," Jen said, and slowly pushed the dildo in Michael's ass.

Jen picked up the pace a bit, and began taking control of Michael's thrusts. Michael felt pain, but then pleasure, and started to get more into it when Jen started with her dirty talk.

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"Oh yes, Anne. I'm fucking this twink. He's gonna shoot in you, isn't he. Give us a baby Mikey!" Jen shouted out.

Jen's weight pushed Michael's head in the middle of Anne's tits, and Anne put her arms around him tight.

Jen wrapped her arms around both Michael and Anne, and was totally in control of their thrusting. Michael was at the mercy of Jen fucking his ass, forcing his dick in and out and deeper into Anne's cunt.

Before long, he could feel his orgasm building, before yelling "cumming" in Anne's chest. Jen and Anne both gasped, and he realized that they also got theirs. He was pretty sure Anne didn't orgasm yesterday.

Their bodies were collapsed on each other, and after a few minutes, Jen backed up from Michael. The dildo made a popping sound when it withdrew, and Michael also got up. Jen gave Anne a pillow to prop under her. Michael's cum was oozing everywhere.

"Shit Mikey, that was hot!" Jen said, and patted him on the back.

Michael blushed. "I thought so too. I have to say, that was a first for me."

Then Anne chimed up, " Speaking of firsts. Alright Jen. You got your fantasy. Now I want to see mine. Michael, after you rest up, you wanna fuck my wife? She's never been with a man."

Michael was standing, putting on his underwear. At first he didn't comprehend that was said, but then his eyes grew huge.

"Um, I guess...I".

"Ha!" Jen said. "If Mikey's up for this, I'm riding that fucker. You know I like control."

"Well?" Anne said. "I hope you don't think of us as freaks, but we are trying to make the best of the situation. Deciding to do natural insemination was humiliating for us at first, but after we met you...well, your bi, sweet, and part of our community...we decided to just have fun with it."

"Well, I have definitely been rode before," Michael said, and they all chuckled. "I'm ready to go again."

"Young un," Jen said rolling her eyes, and Anne scooted over to one side of the king bed.

Michael took it as his cue to lay down, and Jen wasted no time getting on top. For the first time she was fully naked, and he was amazed about how big her boobs were when she took off her sports bra.

Jen was butch, but had a (handsome?) face with no wrinkles.

Michael's dick was already wet from his first go around with Anne, which made it easy for Jen to slide onto his prick. She started riding him at full throttle, and held his hands above his head.

"Oh yeah, Mikey," she called out, and Michael watched as her huge breasts bounced up and down.

She started riding him deep, and Michael could feel his head grazing her cervix. It was like she was trying to milk every drop of cum he had with her squeezing. He was surprised she was so good at handling a dick. She was literally riding the cum out of him.

Anne, watching from beside them, got up and kissed Jen as she rode. She then pinched one of Michael's nipples, and that did it.

"Cumming!" He shouted, and he flooded Jen's pussy with his cum.

She looked down at him, satisfied. "Well, I did it," She said laughing. Anne was also giggling.

"Doc said I cant get pregnant, so no worries Mickey." Jen said with a wink, and dismounted him.

They all got dressed, and both women hugged Michael as he left.

"Shit." He thought. "This definitely took a 180!"

They were unfortunately unable to meet on Saturday, as Jen got called in for a big case and Anne wasn't feeling well. They agreed to meet next month. Michael would still get 300.00 for the sessions that month, so he wasn't too upset.

In mid December, Anne had a missed period. She took a test and realized she was pregnant. After peeing on the stick and finding out the good news, she ran to show Jen.

"Look!" She shouted. "Maybe twins?"

Jen was rubbing her breasts in the bathroom. "My tits are sore, damn it. My nipples have never been this sensitive."

Anne looked at her a bit shocked. "You don't think..."

"Fuck." Jen said. "I sure as hell hope not."

"Oh c'mon Jen. We can afford it." Anne said with a smile.

Jen looked at her with a pissed off gaze, but knew her wife was right. They always wanted a full house. She hugged Anne, and said "Looks like we're gonna be mommas!"

Michael got the news from Cheryl later in December, before he was to meet his next clients. Jen and Anne were both carrying twins. He was shocked to hear about Jen, but was also shocked to hear that Jen and Anne insisted he receive an extra thousand from them.

"Hey, I'm getting tips now?" He thought. And with a smirk he said to himself "I'll take it."

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