Probably, based on personal experience

It doesn't take long to think of one event which should've prevented you from setting up Sam with Ashley. This event made you feel so guilty, that you never told anyone else about it, and you had nearly repressed it. It happened about 2 years ago, you had just gotten engaged to James, but you were having some doubts about getting married. You ran into Sam for the first time since high school. You decided to catch up with him and get a few drinks at a bar. You had a few drinks in you when Sam brought up your engagement.

*FLASHBACK*

"So, who's the lucky guy?" Sam says as he points down at the ring on your finger.

"His name is James. We met in college."

"Does he make you happy?"

"Yeah... He does."

"You hesitated there. Katherine, does James really make you happy?"

"Yes, I love James and I love being with him, but I'm just so nervous about being married. Buying a house, having children, starting a family, all while balancing work. I don't know if I'm ready for that."

"Well, if James isn't totally braindead, then he will realize how lucky he is to get the chance to do all that with you."

"Really?"

"Absolutely, I would do anything to be in his position." Maybe it was the fact that you had a little too much to drink, mixed with the fact that you had a crush on him in high school, but hearing Sam say that he would want to be married to you, set off something inside you. You lunged at him, pressing your lips against. You don't know how long you were making out with him at the bar before he grabbed your hands and led you into the bathroom, and into a stall.

You didn't even think of James, you couldn't believe your high school crush wanted you. You were so excited, that you simply let Sam rip your panties off from under the sundress you were wearing. He shoved three fingers roughly into your soaking wet pussy. You felt like you were in heaven. As he was fingerfucking you, he used his free hand to undo his belt and pants, and pull out his rock hard cock. He sliped his fingers out of you and you felt the tip of his cock pressed against your opening. He leaned down and kissed you. During this kiss, he pushed himself inside you, the moment would have been romantic, had you not been fucking in a dirty bathroom stall.

You groaned into the kiss as he started thrusting in and out of your pussy. You lifted your legs and wrapped them around his waist while hooking your arms around the back of his neck, allowing him to pound you against the wall of the stall. He slipped his hands under your ass, pushing you into his thrusts.

Suddenly, one his hands let go of your ass and you feel his thumb press against your asshole. On his next thrust, he pushed his thumb up your asshole. The sensation was incredible. It instantly set off your orgasm. The tightening of your pussy around his cock made sure he wasn't far behind. With a loud groan, Sam came. His thick, creamy cum spurted inside, filling your womb with load after load of his potent seed. You were luckily still on birth control.

You stayed wrapped around Sam for several moments until his rapidly deflating cock slipped out of your well used pussy. You both are panting from the intense fuck. He eased you down, and you tried to stand with your legs still trembling. You felt some his cum dripping down the side of your leg. Looking over at your panties, you see that Sam had clearly destroyed them when ripping them off. You would have to go without them.

"Wow..." is all you can say after regaining your breath. "I've never had anything in my ass before."

"Really, Katherine? You really need to try having a cock in your ass. I will volunteer if you need me." You chuckle at Sam's bad joke. Your engagement ring suddenly catches your eye, and everything comes back to you.

"Fuck, fuck, fuck! I just cheated on my fiancé!"

"It's alright, Katherine, you're not married yet."

"What the fuck does that matter? I just cheated on James. I love him, why the fuck did I cheat on him?"

"Katherine, you're hysterical, you need to sit down."

"No, you need to get away from me. I shouldn't have done this. I'm sorry, but I have to leave." You run out of the bathroom, trying to avoid making eye contact with anyone who might have figured out what you were doing in the bathroom. You called a taxi and got in. You couldn't go back to the apartment you shared with James, so you give the cabbie your sister's address.

*BACK TO PRESENT DAY*

Sam didn't care about your relationship with James, you have no idea why you thought he would be faithful in his own relationship.

Maybe you set him up with Ashley just because you wanted to see more of him.

You try to push that thought away. It's been years since that night, you had almost forgotten about it. Your life with James is very fulfilling, and one night of bad judgement is not going to destroy it. You leave Ashley to rest, while you decide to make dinner for both of you.