Jessie Maye & Friends

The blonde, chubby MILF of your dreams. Ready to mingle and find more joy in her life. || #HuniePopRP || #NSFWRP || MDNI || Not associated with Huniepop.

[Jessie Maye & Friends @DepressiveMILF]

[🍸] ┄⊹ ┄━━━━━━━━━━┄ ⊹┄ [🍸]

❝ Is it happy hour yet ? ❞

▸ ┊N̶(SFW)
  ▸ ┊ᴊᴇꜱꜱɪᴇ ᴍᴀʏᴇ
▸ ┊ꜱᴡɪᴛᴄʜ
▸ ┊ᴍᴏʀᴇ ɪɴꜰᴏ 🔻

❝ Feel free to spoil me more..~ ❞

[🍸] ┄⊹ ┄━━━━━━━━━━┄ ⊹┄ [🍸]

[Jessie Maye & Friends @DepressiveMILF]

@HUNGVXSSEL Perhaps. But there's only one way to find out~

[Jessie Maye & Friends @DepressiveMILF]

Some people don't understand.

Despite her age, these girls ?
These puppies ?

They're still as firm, bouncy and big as ever.
Just watch em bounce and tell her they ain't !~

[Jessie Maye & Friends @DepressiveMILF]

Watching him do as she said so easily, she knew this would be an easy time.

Slowly stripping out of her own clothes, she'd come closer, her eyes scanning him all over.

That dick sure was big...was it at full mast yet ?

❝ Go ahead and jerk off to me. ❞

[Matthew Parker @HungNerd_rp]

He felt a rush of excitement come over him when she pushed him onto the bed followed by a command.

“Yes ma’am!”

He quickly took his clothes off. Just throwing them in the corner of the room. As his underwear came off his huge cock swung freely between his legs.

[Jessie Maye & Friends @DepressiveMILF]

Small, riiiiight~

With him. Things never go small.

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

Foreplay!

Gotta start things off relatively small before the real fun begins.~ Like say… a French makeout between their lips~?

[Jessie Maye & Friends @DepressiveMILF]

❝ For now. Yes. ❞

She'd smile a little at his kiss to her cheek, before she'd roll her eyes jokingly.

❝ Did you now ? ❞

[Lucas! @classcoasting]

"Nice save on my part."

He giggled and kissed her cheek.

"I missed you."

[Jessie Maye & Friends @DepressiveMILF]

@HUNGVXSSEL They'll see about that !~
Maybe she'll have him begging to cum~

Hmmm..
Tonight.

[Jessie Maye & Friends @DepressiveMILF]

Oh really ?

And just how does he want to go ahead with their fun ?~

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

Good.~ Now, he’s a bit pent up from all of the taking that they had. How about they start having their fun now~?

[Jessie Maye & Friends @DepressiveMILF]

Gonna cost him, ya know ?~

[Drake Redwood @LewdRedwood]

He’s gonna have to confirm they’re still as firm as she claims.

Mind if he cops a feel?~

[Jessie Maye & Friends @DepressiveMILF]

It's hard not to smother him when he keeps asking for it.

That little Android is just hard to resist.

Either way....she's glad to know.

[Issac Breeden @1SSACBR33DIN]

Issac can tell, he's been smothered by large breasts many times since his activation.
That, and his optic sensors indicate Jessie's breasts will still retain their buoyancy even in her sixties.

[Jessie Maye & Friends @DepressiveMILF]

She'd get up from the bed again, before walking on over to him. Grabbing the hem of his shirt, she'd push him onto bed, before she'd talk to him in a commanding voice.

❝ Alright then, take your clothes off. Now. ❞

[Matthew Parker @HungNerd_rp]

Brown eyes would follow her as she sat down on the bed.

“Okay… well. Would you please take charge? I want to experience everything that I can. But I just don’t know enough to do so myself.”

[Jessie Maye & Friends @DepressiveMILF]

@HUNGVXSSEL Fair point. They do and so does she.

Struggle with his size ?~
Haha !~
Oh honey, she can take it, easily. She's sure.

[Jessie Maye & Friends @DepressiveMILF]

Ah. He got her there.

❝ Mm, you're right with that, hun. Oh well. ❞

[Lucas! @classcoasting]

"It's hard to be better than perfection, you know...~"

Sticking tongue out.

[Jessie Maye & Friends @DepressiveMILF]

Yeah yeah, she knows~

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

Atta girl.~ He’ll send in a lotta cash to her bank account soon after they’ll have their fun.~

[Jessie Maye & Friends @DepressiveMILF]

Closing the door behind her, she'd walk on over to the bed, sitting down on its edge.

❝ That's up to you, sweetie. You paid for my services, so... I'm basically yours to play with. Could tell me to take charge though and I will. As for payment...after. ❞

[Matthew Parker @HungNerd_rp]

He didn’t expect to run into such a woman this afternoon. But now they had a whole night together.

Once he looked around for a bit he turned to face her. Finally speaking up.

“What should we do first? And do your want your payment now or after?” He asked softly.

[Jessie Maye & Friends @DepressiveMILF]

Oh ? Double ?

Mmm, now that sounds good...
Sure, sure. She'll take it !~

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

I’ll double the compensation that I just gave you. Should get you to shop whatever luxurious dress you wanted for yourself.~

[Jessie Maye & Friends @DepressiveMILF]

She's rolling her eyes with a soft smile.

❝ And here I thought I'd be more amazing than usual..!~ ❞

[Lucas! @classcoasting]

He's definitely watching...

"You look amazing as always, Miss Maye...

[Jessie Maye & Friends @DepressiveMILF]

@HUNGVXSSEL Co-star, hm ? Ambitious !~
But she likes that...

Any specific plan for how he'll achieve that ?~

[Jessie Maye & Friends @DepressiveMILF]

Unlocking the door with the key she grabbed, she'd wait for him to go inside.
They'd be here for a while.

It was still just like...early afternoon today, so...he had a LOT of time.

[Matthew Parker @HungNerd_rp]

He was honestly expecting some stares when they walked in. A milf with a young man like him. He thought that would draw attention. But this seemed like the norm to them. Which honestly made him rather relieved.

Waiting for the door to open he would step inside. Glancing around.

[Jessie Maye & Friends @DepressiveMILF]

Hmmm..
Maybe !~

What's in it for me ?~

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

Heh, fair enough.~

Sooooo… Ready to release them sweater puppies out hun~?

[Jessie Maye & Friends @DepressiveMILF]

Me ?
Doubt your compensation ?
I could never !~

Just making sure~

[—𝑪𝒉𝒐𝒄𝒐𝒍𝒂𝒕𝒆 𝑺𝒕𝒖𝒅 @Himbo_Jackal]

Awww, doubting my compensation with the way you count those dollars~?

[Jessie Maye & Friends @DepressiveMILF]

Walking inside, the staff knew her already. So they didn't even budge an eye when she'd asked for a room key, being given it almost immediately.

Signaling him to keep following, she'd soon end up Riiight at the door.
Slowly opening it.

[Matthew Parker @HungNerd_rp]

Sounds good to him. As long as it has everything they need for a good time!

And it’s honestly best she does that. He’s a bit awkward at times. So he wasn’t the best at conversation and all that

As they got closer to the hotel his heart rate began to increase. Excitement growing