A really awkward moment

There is a few moments of silence as Jack and Jessy sit there on the bench. Jack with his cock in Jessy's ass and Jessy with her hands still spreading her ass cheeks so Jack could fuck her better, both smelling of sweat and sex as they are left completely stunned over what just transpired.

"Um…right." Jessy says breaking the silence as she turns her head to look at Jack, "Do you think you can pull your cock out of my arse?"

"What…." Jack shakes his head, "Oh, sorry."

Jack does so and Jessy gets off him and walks to her torn and tattered clothes.

"So….." Jack says uneasily.

"Yeah….." Jessy replies as she starts grabbing her clothes

"Look…." Jack gets up, "I'm sorry on what happened. It's was my fault."

"No, no." Jessy turns around, "It's fine. It's not like I wasn't expecting this happened. Tess told me this bloody shit might happened. It's not like I haven't dominated a girl once or twice in college.

Jessy then picks up her torn thong and sighs, "All through I wasn't expecting to go exactly like this."

She then toss over her shoulder where it landed on Jack's head.

She turns around and see her her underwear on Jack's head.

"Oops." She then gives a light chuckle, "Sorry about that."

"No, it's okay." Jack replies as he takes the underwear and hand it back to her, "I kinda deserve it after I popped your ass cherry."

Jessy blushed a little bit, "You could tell that?"

"Oh, yeah." Jack gives a uneasy chuckle, "I'm pretty sure the whole club could tell that."

"Is that why you did it?"

"Huh?"

"Fucked me there?"

"You mean could I tell you were virgin in that area? No, not until you were sweating bullets as I position myself."

"Then why?" Jessie puts back on her bra and points to her clip, "Clip me?"

Jack goes over and starts to clip her bra, "Because the ass can be the most painful areas to get fucked in, even if your anal whore or not. And I know Lisa wasn't going to go easy before she said she wasn't going to be. It's in her nature."

Jack clips it and says, "Done."

Jessie turns around and says, ""So you took my ass…..so it wouldn't as painful if she did it."

"Exactly."

"Well you seem have a lot of experience of getting fucked in the ass. Those techniques you whispered in my ear. Helped a lot. Almost didn't feel a thing until I was….you know cumming. You get fucked there a lot."

Jack sighs and turns around and starts to walk to the locker where he put his clothes, "You have no idea."

Jessy looks down as Jack goes to his locker and pulls out his pants and underwear and starts to put them.

After a few moments of silence Jessy asks while Jack sits on the bench, finishing tying his shoes, "Are you a wrestler?"

Jack chuckles, "Not anymore. I'm only an escort. I'm only here for one job and then I'm out."

"Why?"

"Bad history. Too many demons. I'm doing a favor for a friend and that is if I go on this one date and it goes well then I can let go of her services and go wherever I want to."

"And….is it going well?"

"I don't know…" Jack looks his shoulder at Jessy with a smile, "You tell me?"

Jessy smirks, "Right."

She turns around and starts putting on her shorts.

"What about you? Are you a wrestler?"

"Wanna be." Jessy says as she starts to struggle on her tights pants over her round ass.

"Tess says I would fit in….you know….." Jessy looks over her shoulder with a smirk, "My assets."

Jack smirks and smiles as Jessy continues while zipping up and buttoning up her shorts, "But the big boss lady says I have do a three trial thing before I can become official. Nothing hard, just three matches. One…."

"One you have to lose, one you have to win, and one you have show off your skills."

Jessy looks at Jack and says, "How do you know?"

"I told you." Jack chuckles, "I was a wrestler once upon time."

"So you did them?" Jessy asks as she starts to put on her socks and shoes while standing up.

"Me? No. The league I was part it have very different ideas then this one, a very different culture as this one too. But I know people who have gone through them." He then bends and pick up her shoe and toss it to her, "You should be fine."

He then turns back around, "It's easier then you think." He puts on his shirt, "Don't think too hard about it and you will be fine."

"Thanks." Jessy then pulls out her cell phone from her shorts and went through her text message, "Bloody hell." Jessie says to herself and then says over her shoulder, "Good new my friend Tess found that thing she wanted to retrieve."

"What was it?"

"Her dildo." Jessy turned around, "Apparently she had it in her purse this entire bloody time and she'll be waiting for me in the car with that man she fought in the ring."

"James Green."

"Yeah, Can you believe it? Probably shanking it up in the back seat of that rental while I was being **** here." She turns back around, "Bloody unbelievable."

Jack looks over his shoulder and sighs and gets up, "Hey…what you are doing later tonight?"

"I be in my hotel room. Showering this cum off. Why?" Jessie turns towards him, "You want to take my ass again?"

Jack gets close to her and puts his hands on her hand that was putting her phone back in her shorts pocket, "I was actually thinking of takings something a little bit more pleasant."

Jessy breathing starts to get heavy as she asks slowly, "Why do you want little old me? Isn't bitch tits over there." Jessy nods her head over towards the locker room entrance, "More your liking?"

"I told you." Jack gets up close, almost pinning Jessy to one of the locker as he takes her hand put it over her head, "That was a favor for a friend. Besides I had my eye on you the moment I enter the bar."

"Some friend." Jessy replies as her lips almost touches Jack.

"You have no idea. She saved my life."

"But you still didn't answer my question. Why me? Out of all the women in the bar, all those skanks and whores who would die to spend a night with you after that match you pulled, why me?"

"I don't know, do I need a reason?"

"In this case, yes." Jessie replies as both wrestlers were seizing each up with their eyes.

Jack thinks about it for a few seconds, "Maybe because you're most normal person there."

Jessy looks at him quizzingly, almost looking offended, "And that turns you on?"

"When you had the life that I had…." Jack leans close and starts to breath warm breath in her ear, getting Jessy turned on, "And the family I had. The bizarre and strange is almost a turn off."

He starts to nimble on her ear making Jessy moan.

She pushes him off. "Sorry, I can't. I just can't"

Jack is stunned. "Why, is it because of what happened?" Jack points over to the bench where they had sex, "I apologize for that."

"No, of course its not that." Jessy says as she walks over and picks up her hand bag she dropped, "That was some of the best fucking I had in a long time."

"Then what?"

Jessy leans and says with her hand bag and torn thong in her arms, "I don't date wimps."

Jack is flabbergasted at what he is hearing as Jessy starts to walks away, "What….what….were you not here when I fucked you and you were begging for me to fuck your ass?"

Jessy turns around, "And were here when you let your 'date' boss you around? You were pet bitch from what I saw. Pitting around, making excuses of why she shouldn't **** me and pick came to choose you faulted. I don't need a man like that I need someone who is decisive and macho enough to know what he wants and take it."

"You mean a douche bag?"

Jessy looks at him annoyed.

"That was a joke. Besides, I didn't have a choice. She would've beaten me up and fucked me too right next to you if I didn't comply. And trust me she would've done a lot worse if we were both on our knees licking her pussy. Her and her goons."

Jessy looks annoyed at the statement of her being on her knees and Jack saw this and knew he needed to fix this quick.

"Besides didn't you see me dominate her in the ring?"

"Beginners luck."

"Beginners…..beginners luck?" Jack is completely stunned at what he is hearing, "Come on you got to give me enough credit then beginners luck over what happened in the ring, especially over a seasoned wrestler like Lisa "Dollar Bill" Cole."

Jessy says nothing.

"Look, I'm not asking to be your boyfriend. In fact if all goes according to plan I'll be leaving this city by the morning. I'm asking for is one night of fucking and champagne. Something a little bit nicer then what we just had. And trust me I will show you how macho I am."

Jessy looks at him and says, "Well you did make me cum one or twice and you did fuck that bitch pretty good in the ring."

"One night. That all I want."

"Give me your phone."

"Why?"

"Just do it you silly git." Jessy says with a smile.

Jack does and she starts to type.

"What are you doing?"

Jessy replies while finishing typing on his phone, "Giving you one night."

She gives it back to him and he can see she giving him her hotel room and phone number.

"Call me when you are done with your 'date' and you can show me how much of a hunk you are."

"Trust me I will."

"Great." Jessy lean over and give him a peck on the cheek, "I'll get the cuffs."

"Oh, shit, no!" Lisa screams in the bar.

"Looks like your mistress is calling."

Jack looks at Jessy, "Ha Ha very funny."

She shrugs, "I try. I'll think I take the back way before someone takes my 'back way again."

She walks to the back entrance as Jack looks down at his phone at the information before Jessy says, "By way I never got your name."

"Jack. Um Jack…." Jack think of a last name and finally came up with one. A last name of someone that he hated but at the same time loved with all his heart, "Jack Matthews."

"Well Um….Jack Matthews. Don't be late."

"Fuck this shit! Break! Beat! Get over here."

Jack looks over at the locker room entrance and then back Jessy who smiles and whispers, "Bye."

She pushes opens the door and goes while Jack goes back into the bar to see what is the matter with a new hope that everything will turn out right in the end.