Author's Note

This chapter was written in its entirety by Commander_Bobo, go check him out.

006 “Diamond Tiara” Earth Pony, Filly

Bio: Collected after running away from her abusive home. We had to allow her some time to heal before being admitted into the roster as she was found with many bruises and injuries around her genitals and flank.

-Deep and Semi-Loose Pussy
-High Pain Threshold
-Begrudgingly Compliant, Doesn’t Struggle
-Slow to Cum
-Anal Ready

006 - Diamond Tiara

As you walk down the hallway towards the door that holds your filly for the night, can’t believe you’re going to be this filly’s first customer, surely it will be worth the extra bits.

You reach the door and open it to see a small pink filly sitting on the side of the bed looking down at the floor, she notices you and quickly looks towards you, taken aback from the intrusion. Without skipping a beat she speaks “Ugh, I didn’t know you would be coming so early.” she rolls her eyes “So, what do you want?” she says emotionally. You skip the pleasantries and just motion your hoof towards the bed.

She must be very well trained as without any further instruction she stands up on the bed and points her rump towards you, flicking her tail up for an easy entrance. You stop to look at her ripe genitals before you're interrupted by her “So you gonna do it or not?”. You quickly snap out of it and go over to her.

You hadn’t even realized it but you’re already fully erect, while standing over her you decide to start grinding against her pussy, she gives out a moan as you do. You continue to grind up against her eliciting some more minor reactions but now that she's properly wet you stop and lay on the bed and tell her to position herself on top of you, which she does with haste. Although you thought it would have been implied, she didn’t get the memo, so you lift her rump and force yourself inside of her with your hoof. She moans as you insert your cock, she is quite loose and you're able to put the first couple inches in without any resistance from her youthful genitals.

You're now just mere inches away from her face and inside of her, you pull her face down onto yours and begin to kiss her. She is slow to reciprocate your kiss and is very awkward in her ‘kisses’. It’s just you forcing your tongue in and out of her mouth, she is not enjoying it and that only makes you want to continue.

All this kissing makes you forgot your primary goal, you push her mouth off of you for just a second to begin forcing her pussy up and down on your cock, she takes the hint and starts bouncing on it with a deadpan face, giving out an occasional moan or two as she lets you go further inside of her. You return to making out with her, closing your eyes as you do. Although she isn’t as tight as the other fillies working here she’s still just as hot, if not hotter and you feel yourself getting closer to climaxing.

Pulling her tongue from her mouth for a moment to tell her to go deeper before continuing your passionate invasion of her muzzle, she simply nods and begins to put more and more of you into herself on each bounce, moaning as she goes past your medial ring. You quickly resume kissing her as she bounces on your cock. She begins to moan more as it goes deeper, her moans are louder than before even though they’re muffled through both of your mouths.

Your cock is finally entirely inside of her, and you can’t believe how you can be so deep inside this filly. You wonder if this truly is her first time with a customer as she is not as tight as you would expect, but you stop thinking about that as you get closer to climax. The tip of your cock starts to flare as you feel yourself right on the edge. The filly on your cock, like the good slut she is, feels this and begins to pick up the speed. You pull away from the filly’s mouth and curse at the top of your lungs, giving her a shock before pulling her down all the way on your cock as you cum. Ropes of semen burst out into her kitty as your cock throbs inside of her. She yelps out a high pitched moan being filled even more than before. She collapses on your chest with your cock still inside her as you both catch your breath. As she lays there you can’t believe the experience you just had with such a cute little filly, you start petting her mane while she keeps her head muzzled on your chest.

You stay there for a while just snuggling with your latest conquest before looking at the clock and realizing that you’ve been cuddling for the last 15 minutes, but more importantly that you still have 20 minutes on the clock. You think of what next to do to this filly to get the best bang for your bits, but just thinking of the many possibilities of your perverted mind makes you get another erection. The pink filly sturs as you pulsed in her pussy, waking her from her half slumber. She looks up and gives a cute little yawn that only a cute filly like her can give. She looks down at your erection growing inside of her. She looks back at you once again with her deadpan expression from earlier.

You thought for a moment that perhaps she was happy with this arrangement, but how could that be true? How could anypony be happy being an unwilling and unpaid prostitute before they’ve even had a colt friend? Wasting away as nothing more than a sex toy for a bunch of pervs like yourself while her friends got to live a normal life. You quickly snap out of thinking of how you could be scarring and ruining this filly’s life forever, after all ‘if I don’t do it somepony else would’.

You take a deep breath and look at the clock, you’ve lost another minute of valuable time to your thoughts. You tell her to take your cock out of her and she complies, still laying on your chest. You ask her to insert it into her anus and she seems less willing to do so. You repeat yourself and she finally puts it in her ass, giving out a loud moan as she did. She’s much tighter in her ass, she’s slow to put it in but you know you only have so much time left so you pull her down and force yourself into her quite quickly, pushing out a high-pitched yelp from her as you do. She shivers from the shock of having such a large member inserted into her under-used hole.

She needs no more instruction and begins to slowly push her pelvis up and down onto you. Although she’s much slower than when you were in her deep pussy she’s made up for it with the undeniable tightness of her anus. You position her head on your chest, her hot breaths feel nice against your chest.

As you continue to slowly fuck her you see she’s still in her usual deadpanned expressionless face. You decide to fix this by putting your hoof towards her vagina. You begin to massage her clit very quickly, her breath against your chest turns into a heavy and wet pant that starts to stain your fur.

You take your other hoof and force her rump to bounce faster and deeper onto your cock. You're really feeling it now as she passes your medial ring. She’s also quite adamant about the experience as you can sense she’s getting closer to orgasm. Although she’s already had quite the experience, her pussy is not just done yet, although you're just about ready to cum you hold it back so you can witness the filly cumming first to avoid having to buy another hour with her.

Although you try to put up a resistance, you can feel yourself coming closer to cumming. you lustfully yell out ‘yes’ to confirm that what this underaged whore on your cock is doing, is working, just as you get to your very edge of jizzing you feel yourself about to complete your goals with the cute pink filly’s genitals. in a lust-filled state, you slap her ass and scream out for her to keep going. She immediately starts to shiver and yells out “No, please no, daddy!” She picks up the pace to the extreme and before you can even think, you finally climax, and clearly what you were doing to her was working, as she gives out a huge moan before squirting out onto your abdomen, trapping your hoof inside of her.

This was much more than what you were expecting from her, as an explosion of fluids erupts from the both of you. As semen seeps out of her ass and she soaks your stomach in her youthful juices, your semen comes out of her in waves as she continues to have her orgasmic experience and her vagina seems to never stop as she continues to squirt out onto you.

You lay back on the single pillow on the bed and catch your breath, she puts her muzzle deep into your fur, but you can hear her mumble “Please daddy, no, I promise to be good.” and things along that line as she continues to shake and shiver on your chest. Your mind begins to wander as you think what the hell is up with this filly and what might have happened to her before she began to work here. Your mind is interrupted by your eyes as you see the clock on the wall, you only have a minute left. You pull her off from your cock, it makes a satisfying pop as you do. You give her one last kiss on her forehead as you very gently push her off your chest and onto the bed. You get up and move to the door to leave, but you look back one more time to see her still shaking and now curled up into a ball on the bed. As you open the door a staff member is already there to warn you that your time is up.. You leave with a new favourite pink filly at the facility. As much as you want it, you don’t have enough bits for another hour so you’ll just have to remember to come back for her and you can only hope she remembers you when you do.