Ashley Olsen

The Agent- Ashley Olsen

This was strictly business for as much as you were concerned. You didn't have a relationship with the Olsen Twins, Mary Kate and in this case, Ashley, outside the occasionally nice word here and there when Elizabeth would invite you to private events. This time around Elizabeth had called you out of the blue and asked if you would go and spend a night with her sister as a personal favor to her friend to friend. You didn't exactly understand what sleeping with her sister was going to help with and to be honest, you had been pulling a lot of these types of favors recently, and was starting to feel a little whorish. She laughed when you mentioned that and didn't even bother replying she just said she would send you the address to the hotel Ashley was staying at and it would go from there. You of course texted your women to make sure they were kept in the loop as you didn't like doing things without at least their knowing and Selena just sent a smiley face asking you to tell her she was a big fan. You shook your head and had Danica close up the suite for the night so you could get a rush on the traffic. It was almost time for the final move, and your mother would be back for one last week to finalize some paperwork and say goodbyes to her long-time friends and associates. You were still mixed about the entire thing but you were your person and so was she. You couldn't do anything about it now. It was time to move forward and a lot of that was gonna hinge on your doctor's visit in a few weeks. It was a big decision, and as it weighed on you you decided to shift yo your focus on what was ahead.

Ashley greeted with a glass of wine in hand and an eye roll as she asked why Elizabeth insisted on you being the one. You were a bit thrown off by the attitude but didn't say anything as you shut the door behind you and asked what was going on. She stood at the edge of the bed and sat down, taking a sip as she told you to get naked, as she wasn't interested in talking about her issues and was just needing to be fucked. You shrugged and took your clothes off, exposing yourself to her as she smirks and nods as she finishes the drink and sets it on the floor as she motions for you to get closer which you do. She took your cock into both of her small hands and began to stroke you off as you grew harder in her grasp as she mentions Elizabeth had good taste then, a bit of a 180 from her initial comments but you didn't bother to bring it up as she massages and caressed your dick before she said she doesn't suck cock anymore, finding it demeaning. She spits on your cock and rubs it in, stroking it faster as she then leaned back onto her elbows and kicked her legs up, hiking her dress she had on up a bit to reveal she wasn't wearing any panties. She pulls you closer to her and you got lined up to get cunt and pushed inside, her tiny frame shuddering almost immediately as her cunt gripped you tightly, almost as tightly as any you've ever been inside as it was physically painful to put anymore of your length inside of her. As you got about six and a half inches inside, she grabbed your hips and told you to show her no mercy, almost in a pleasing, begging tone as she grabbed your hand and put it to her neck as you tightened up immediately, watching her smile as she stifled a scream as her pussy spasmed as you had started to move your hips more forcefully, taking slow deliberate strokes which causes the bed to shake and her body to squirm from you but the grip on her neck kept her in place as you pushed your hips in and then pulled nearly all the way out to the tip before slamming back inside.

You repeated this slow and violent pace until she had squirmed out of your grasp and curled up as she touched her spasming womanhood and as you grabbed her ankles and yanked her back to you as you got onto the bed, you grabbed her head and yanked her head back as she moans happily as you got her laid onto her stomach flat before pushing into her pussy from behind in the prone bone position, Your grip on her neck and hair keeping her head up as you just rocked your hips violently forward, jamming of much of your dick into her cunt as you talked down to her, Ashley jawwing back at you as you felt her pussy spasming and pulsing as she rolls her eyes and eventually trails off as you stroked away deep and hard as you let your orgasm build to a mighty crescendo as she begged for your cum, your hips never slowing down as you felt her cunt lock up to be even tighter then it already was as the pulsating of her inner walls intensifies to such a degree that your cock jams in and you held your hips down and in as your muscles spasmed and you came hard, your dick throbbing madly as thick hot spurts of cum fired off deep into her tiny pussy as her small womb became immediately overflowed with your large orgasm as you could feel it pressing and oozing out between your crotches not even halfway through your load.

As your orgasm subsided you pulled out and watched an immediate amount of seed pool out of her womanhood and onto her thighs and the bedsheets, Ashley moaning and panting as she grabbed the sheet and wrapped it around her as she looked at you and smiled as she thanked you. You asked what this was all about and she shrugged and said it was between sisters and you served your purpose. You sighed and didn't saying anything as she grabbed your arm as you were about to get off of the bed and said she was sorry for being so short with you when you first arrived and that she would let Elizabeth tell you what was going on if she wanted to talk about it. She just wasn't ready. You nodded and smiled and said it was okay as you headed off after dressing, taking the long ride home as the traffic was even worse than expected. You didn't even bother to text Elizabeth as you owed her enough of a solid to just let it go. She had recently been offered a large deal by CAA to leave your agency and she didn't do so. Why, well, that was still a mystery even to you as the deal was far better then anything you could've given her, even with Lei's financial backing. When you got home you made a stiff drink and sat on the deck, eventually FaceTiming with Selena as she asked if you told her and when you said you forgot you had a nice chuckle at the barrage of insults she hurled your way. It was a pleasant way to end a day, even with all the thoughts creeping in about what the future was gonna hold.

End of chapter.