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Chapter 5
by
Cmello
What's next?
Post shift
Tyler was nervous. The whole shift his boss was texting. Either on his phone or Tyler’s own phone. When Tyler got his phone back Kyle told him, with a big smile, you and your sexy, naughty girlfriend have a lot to talk about. I’m looking forward to the future with you two.
When Tyler got into the car he was nervous to see what messages that “he” had sent to his girlfriend. If he knew he was going to have his phone confiscated he could have warned her. He sat in the car and read “his” messages…
____
Kyle messaged Riley (on Tyler’s phone):
You: “Kyle loved the photo. He’s actually more chill now and letting me message you during the day. I think it was worth the money to send. Maybe we can make some more money with Kyle. If you’d be okay with that?”
Riley: “Idk, it felt a little dirty and wrong babe”
You: “get a shower and you’ll no longer feel dirty. :) Send me a picture when you’re done so I know that it was done and you’re all clean!”
Riley: 
I do feel cleaner. Now cum home so we can get dirty again ;) does my mascara running remind you of me deepthroating your cock until I start to cry from my efforts? Hehe
*you notice this message was forwarded to kyle’s phone* you gulp. Fuck. This is going to be bad… you continue reading:
You: fuckkk that’s so hot baby. If you’re horny you should masturbate.
Riley: already am. You know me. Your horny little slut :)

You: god damn, I’d love to pound your tight pussy right now.
Riley: I’m here and ready for you. Tell Kyle to let you out of work early. My ass is up and ready for you to mount. Don’t you want to mount your sexy, slutty girlfriend? Grip my hips and take control of me. I know you do… ;)

She continued: Tell Kyle I said pretty please let my Tyler come home early. Maybe we can send him photos of me sucking your cock? That’d be worth more than $200 :)
You: “That’d be hot babe. I’d like that.”
Riley, responded saying: “speaking of sucking cock. Your boss send me this message today when we were texting:”
*screenshot of message in brackets below*
[Tyler: Riley you remind me so much of the last girl I fucked. She was a cute, petite girl like yourself. I loved watching her little white lips try and fit my whole cock around her mouth and she loved the challenge. I bet you’d love the challenge too.

*Holy fuck, that’s my sister Melissa, Riley never met her. Melissa fucked my boss. Kyle keeps reading..*
Riley: haha I don’t think you should be sending me this kinda thing. But if we did that it would be a lot more expensive than $200
Kyle: hey, maybe your boyfriend would pay to watch! Maybe he’s a little cuck :) Maybe he’d love to see how deep I could take you. My ex loved to feel me drive deep into her. She loved how full I made her. I bet I could make it to your ribs. You’re so petite.
]
*Riley texting “you” again following the above screenshots*
Riley: “Any truth to that statement haha are you a cuck? Btw, I didn’t picture your boss to be black. You know the guy I dated before you was black *emoji covering eyes*”
You: I mean. Watching you take a cock would be pretty hot. Maybe we could get $200 or something for that too. I bet you’d like it as well. You know I haven’t been able to satisfy all of your sexual needs. Maybe for your birthday I can give you a hall pass. Your sex drive is phenomenal and maybe today after work….
_____
You stop reading there. You just couldn’t read anymore. Fuck. Kyle got so many photos from riley today which he forwarded to himself. He also made promises that you really don’t like for future actions.. Should Tyler even tell Riley she wasn’t texting him? That honestly would break her. She sent so much. She may be a sex freak but loves putting out her innocent façade.
Kyle got so many photos today that photos may not be enough anymore… he may want more…. Especially since “Tyler” basically said he’d be okay being a cuck for not a lot of money. Who else knows what else that “he” agreed to or suggested. You’ll let Riley tell you tonight then you can tell her you changed your mind on them..
What's next?
Approved cheating
Workplace sexting gone wrong
Story starts off focusing on a couple and how they are tricked/seduced by the man’s boss. The story then takes some wild turns as more information becomes known. Tyler realizes the once unwanted girlfriend sharing can be used to his advantage to get what he wants. He has the opportunity to upgrade his sex partner. He has the opportunity to make his sister his.
Updated on Jan 15, 2026
by Cmello
Created on Oct 4, 2025
by Cmello
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