The Agent- A Hopeful Offer
As Halloween drew nearer it was nice to have the others be so into the holiday like you were and so you had been coordinating with Nathalie and Kaitlyn on what the babies Halloween outfits would be since they'd be here together for the first time. There was also plans in place now for you, Kaitlyn, Alycia and baby Kat to head to the UK for Christmas so they Kat and Jonah could continue to at least spend some weeks together around some holidays until a more permanent solution could be had in the coming years.
Still as Dana was coming into town for a Halloween themed horror com, you were surprised leaving Charli XCX 's Airbnb by a phone call from Judy Greer who was coming into town for the same con and was also back from filming her next project and had thought about coming to see you since it had been a long time and you had always fancied Judy, and had thought about maybe even broaching her joining the harem, since she got a long with Dana and the others when they would meet and you and her had undeniable chemistry, exhibited by the way she was blowing you on the bed in the downstairs main bedroom as she had arrived early in the afternoon as you had decided to take a half day from the office.
Judy used both hands as she twisted and jerked at the same time that she sucked along half of your length, drooling and spitting as she would then jerk the excessive saliva into the skin of your achingly hard manhood as she would catch your eyes and smile as you'd move her hair from her face as she would go back to the tandem twist and suck before she slurped off and wrapped her perfect tits around your cock, smiling as you moaned as you tell her how great her tits are as she makes a joke about how you had plenty of younger better tits to do this with which made you "tsk" at her as she blushed and held them against your cock as you moved your hips up and down against her breasts plate as the snugness of her tits against your cock felt incredible.
After a few minutes of this she eventual turned herself around and got herself in position with reverse cowgirl, deciding to stay on her knees as she leaned down and arched her ass which looked incredible as she grabbed your cock from under her legs and aimed it into her slit as you both let out a loud groan as you smacked her ass cheek and made her yelp as she moaned and began to push her his back as she palmed the bed by your ankles and just pushed and rock her hips back as your cock crashed nearly balls deep into her mature slit as her inner walls were already a trembling wet mess.
Judy just screamed and rocked back as her orgasm wrecked her, but the way she was positioned with how deep you were meant that even following the first big orgasm she couldn't fight the sensation off and within a minute she was cumming hard again as your hands were firmly just rubbing and occasionally smacking her ass as she slowed down a bit following the third orgasm as you decided to take over and pulled her back so that she was laying against you as you hooked her legs and pulled them up, so she was still sitting with herself most buried down onto your cock as you had her palming your shoulders and chest for stability as you held her legs up and just began to thrust yourself up and down.
Judy was screaming like a banshee as your cock assailed inside of her as the force of your thrusts and the way she was positioned with her legs hooked up as she just was at your mercy and you'd have to try this position a bit more as it felt incredible and with Judy's cunt constantly spasming and her screams of pleasure mixing with your own pleasurable grunts and groans, you felt your orgasm drawing closer and closer as you just worked yourself up and down without much other thoughts then to cum and as she screamed again and you felt her kegel up around your driving manhood, that spasming constricted pressure did the trick and you pushed inside and let go as you let out a roar of pleasure as your cock was jerking and pulsating against her trembling clenched up inner walls.
You held her as still as you could as your thick strands of jizz flooded inside of her, filling up her womb and feeling the trickle down as you stayed buried inside of her until you let her legs down and pulled yourself out as she quickly laid to your left side in a whimpering panting mess as you kissed her bare shoulders and felt her reach back to pull your face to hers as she turned her head and the two of you kissed for a long moment as she moaned after the kids and said she liked that a lot as you just nodded and agreed with her as she turned over to face you, hiking her leg up against your hip as she rubbed her nose against yours and smiled that warm smile of hers as she glorified your face and kissed you softly.
The two of you laid there for a bit, catching up on life and making out like teenagers as you eventually slipped yourself back inside of her as her leg being hiked on your hip allowed for you to maneuver yourself back into her as the kissing and the way her nipples were brushing against your chest as you talked clearly turned you on as she sucked in her breath feeling your cock cresting back inside of her as the two of your stayed nose to nose, eyes locked as you grinded yourself in a gyrating motion as your cock stirred against her cum stained inner walls as she cupped her hands to your cheeks and just breathlessly moaned and let out hushed gasps as your cock glided and stirred along her cunt in such rhythm that she couldn't help but cum, her body trembling and shaking as you both moaned loudly as she locked up tightly and made you slow your motions as it was more force then expected.
Eventually you lifted her leg a bit higher into the air to give you more room as you started to move your hip from side to side to thrust more quickly into her cunt as she just wrapped her hands around your neck and pulled your face to hers, kissing you passionately as you fucked her in this sideways missionary while your orgasm built as hers rocked her body against, her toes curling as she tossed her head back and she bellowed out for you to go harder as you did exactly that, slamming with more speed and force as her cunt was spasming so often along your stroking cock they each subsequent thrust felt better and better then the last as she was screaming and moaning incoherently as the orgasms were taking her ability to speak or sound coherent.
You didn't have to wait much longer for your own orgasm as you found Judy's lips and kissed her to drown out your own loud scream as you came hard, pushing yourself deep inside as she grips the back of your neck and holds you against her lips as you kept yourself buried deep inside as your cum filled her womb so much that you could feel the instant seeping out between your crotches but you couldn't focus on anything other then Judy and her lips as you kissed all the way through the point where both of your crotches had stopped spasming and pulsating in tandem.
After a few minutes of just kissing you eventually both pulled away and eventually enjoyed the sound of the other panting and groaning as you collected your thoughts and eventually got up to get a shower in as you still had to get to the office. You and Judy showered together, laughing and cracking jokes and talking about the upcoming horror con while you waited for the right time to talk to her about joining the harem, eventually just coming out and asking her if she would want to, laying out your feelings for her and why you think she would be perfect.
Just smiled and blushed at the thought of it all but politely turned it down, feeling she was too old for you and for that and that she was happily married regardless of her propensity to drop her panties for you. She kissed you when she saw the disappointment in your look and she tells you she'll always make time and be here for you when she can and that she's just inclined to be part of something like that, though she was immensely flattered by you wanting her to be.
You dressed and saw her out to her car as she says she'll see you at the Con and sometime down the line as you kissed her cheek and thanked her coming over as she headed off as you felt a bit foolish but you would've regretted never asking her.
You eventually got into your car and headed to the office hoping maybe one day she'll reconsider, while knowing deep down it probably wouldn't happen. Still, you knew you would always have Judy Greer as a part of your life in some way, and that alone was comforting.
End of chapter.