Cheat Day - Sex Stories

Cheat Day

... “Ethan, you okay?” he asked. “I get this might be…”

“Weird? Yeah, sure is,” I admitted. “But when isn’t it weird with you two?”

“It’s actually kinda freeing,” Jake replied. “I dunno, I thought it would cross a line, like, things won’t be the same. But now that I’m here, it’s kinda like… yeah, whatever, I have a cock. Wow, I’m a dude.” He remembered John was in the room and quickly added, “A cis dude.”

John laughed. “Don’t worry,” he soothed, despite his own nerves. “You’re, uh, lucky in the genetics department.”

Jake laughed. “So I’ve been told,” he agreed, grabbing his dick by the shaft and swinging it around a little. “I can totally see why jocks swing these around the locker room now. It’s like, ‘yeahhhhh, I got a peeenis.’” All of us laughed.

“Yeah, I can’t do much with these,” Katie admitted, grabbing her own boobs and holding them up. “I can’t whip them around or anything.”

“They are really nice though,” Jake replied, swiftly adding, “y’know.”

“You think so?” she asked, releasing them. “I always felt like they were too small.”

“Too small for what?” Jake asked incredulously. “It’s not like you’re currently nursing or something. They look good, they look se-” He coughed. “Se… sentimental?”

“Sexy,” John laughed. “He was gonna say ‘sexy.’”

“You failed, bucko,” Katie laughed, taking a step towards him. “We asked you not to make this sexual. I didn’t even bust out my pussy, just ma’ boobs, and even then…”

She thought she was going to ...

... embarrass Jake again. She was wrong. “I guess you got me,” Jake replied, matching her confidence and then some, taking a step towards her. His dick, jutting out far ahead of him, touched Katie near her bellybutton. “Are you gonna punish me?”

Katie started breathing heavier, then started to laugh. A very nervous laugh. An “I’m definitely turned on but shouldn’t be and don’t know how to proceed” laugh. “Jake…” she breathed. “The others are right there…”

I wanted to dispel the tension. I turned to John and shored up my strength. “When you said you wanted to get used to sex stuff, bet you didn’t picture this, huh?” I asked, trying to cut the tension.

“I gotta admit, Ethan, I’m impressed,” Jake said to me. “You got to see these boobs before and it had no effect on ya? Because right now, what can I say, I’m… hypnotized.” His hand slowly rose, going up Katie’s side. Katie got a look in her eye I never saw from her before – this glossed-over, hopeless, almost scared look. A pining look. She made zero effort to stop him, and just bit her bottom lip.

I needed to reply, quickly. “Uh, yeah,” I admitted, turning back to Jake, trying to be a little louder than I normally would be. I could have just said “save it for the bedroom” or even “stop, this is getting too weird.” So why couldn’t I? “I dunno. I guess I know we didn’t see each other that way. Plus, I don’t usually go for friends that way. I’ll usually feel it more for people I’m meeting for the first ti-”

My words caught in my ...