Matildas Visit

David waited anxiously for Matilda to arrivd. He didn’t know what to expect at this point but would accept basically anything that would give him some relief. He started to fantasize about Matildas caramel skin and soft ass. He hoped to get a chance to fuck her again. His cock ached and he tried to think about something else.

It felt like days passed but finally a dark sedan pulled up to the curb outside Davids apartment. Matild stepped out of the car with a small briefcase and came up the stairs to David’s door. He let her in hurriedly and shut the door behind her.

“Welcome, thank you for coming.” David said hastily.

“Of course, Ms. Remington said you needed some assistance with your equipment?” Matilda said in a professional tone.

“Yes, its been weeks and I need this thing taken off.”

“Hmm” matilda pouted and appeared to think for a minute.

“Nancy said you would be able to help me out with this.” David attempted to hurry things along.

“Yes, Ms.Remington gave me pretty clear instructions on what I was to do.” She put her case down and removed a key from her pocket. “You have a choice.” David’s stomach turned. “I can take the cage off but you will not see Ms. Remington again, or I can help you release with the cage on.”

David was dumbfounded. He couldnt believe what he had gotten himself into.

“Between me and you, would it be possible to take it off for just an hour, maybe you and I can have some fun, and Nancy doesn’t have to know?”

“As tempting as that may be, I was given very specific instructions.” Matilda looked almost disappointed as she said this.

“How likely is it that Nancy and I actually end up working out?” David was weighing his options with great care.

“I know that she likes you, but she is very cautious about the men she spends her time with.” Matilda said. David couldn’t tell what to do with this information.

“How would I even “release” with this thing on?” David’s resolved was weakening.

“There are a few ways to do it but I can assure you that I will drain you completely.” Matilda said almost flirtily david was curious now.

“I cant even get hard, I’m not even sure what you would do.”

“You dont have to get hard, trust me.” Matilda said coyly.

“I don’t know…” David trailed off.

“I don’t have all night, you can either do as I say and as Ms. Remington requests or I can remove your cage and be on my way.” Matilda said with a hint of frustration.

“Alright, alright. What do I need to do?”

“Good boy.” Matilda smiled, “take off your clothes please.”

“Okay…” David began removing his shirt and sweatpants, he had chosen not to wear his usual boxers because of the cage strangling his cock. He stood naked in his apartment watching as Matilda also undressed. He decided he made the right decision as she removed her coat and saw that she was wearing black lace lingerie with straps running down to a pair of nylon stockings. She opened her briefcase and put on leather gloves up to her arms.

“On your knees.” Matildas tone became stern as she pointed to the carpet.

“Okay…” david obeyed. He felt a little silly sitting in front of her on his knees with his cock struggling against its plastic cage.

“Good boy. You’re going to listen to everything I tell you right?” Matilda said in a commanding tone.

“Sure.” David said without comitting. He felt a sharp pain on his cheek as Matilda slapped him across the face.

“You will call me mistress and you will speak properly!” She grabbed him by the cheeks.

“Yes mistress,” David said in surprise.

“Good boy, I will be standing in for Ms. Remington so you will treat me with the same respect you show her.” She reached down and felt his caged manhood. “You like that dont you?” She smiled in his face.

“Yes… mistress.” David admitted.

“Alright, I don’t have time for all this, bend over.” She slapped his ass with her gloved hand. David bent onto all fours.

Matilda removed a small curved dildo from her bag and some lube.

“Starting to get pretty familiar with your asshole?” She laughed as she slapped some lube on David’s tight sphincter. She rubbed it in roughly, pushing her gloved fingers past his tight ring and letting the cool liquid slide into his colon.

“Ooh.” David couldn’t help but react but tried to restrain his surprised moan. Matilda slapped his ass hard.

“Shut the fuck up. This is annoying enough as it is without you being a little bitch about it.”

“Sorry mistress.” David said quietly.

“God, what is it about Ms. Remington that has you boys all crazy. You’d do just about anything for a single lick of her bare pussy.” David was quiet, willing to accept that he was in quite the predicament all for his own lust. Matilda worked her fingers into David’s loosening hole and he groaned. “Have you ever been milked?” David shook his head, afraid to answer. “I assumed not. Well, I’m going to stretch your little boy pussy hole enough to get this curved dildo in there, and then I’m going to use that to beat the crap out of your prostate until your eyes roll back and you start begging me to just fuck you already.” Matilda was starting to enjoy herself, her hand pressing harder and deeper as she got two full fingers through David’s defenses.

“Oh shit.” David couldn’t help himself. The discomfort was familiar.

“Shut up, you like it. Ms. Remington had you singing like a whore when she reamed you. It’ll be easier if you just accept it.” Matilda was satisfied with the small gape she created and shoved the dildo into David’s ass.

“Gaah!” David cried out in pain. Matilda shoved his face into the ground.

“I said shut the fuck up! Don’t embarass yourself. Take it like a man.” She began twisting and pulling the dildo in David’s ass. He squirmed and groaned. She turned and angled it every which way, stretching David out until she heard a moan. She focused in on that area until David’s breath began to come more quickly. “There’s your little clit. You like that?”

“Yes mistress.” Was all David could say as his brain became overwhelmed with the feeling coming from deep in his gut.

Matilda ground the plastic against David’s puffy little prostate and he bucked his hips as she worked him. It didn’t take long for a steady string of precum to drip from the cage.

“And now we do this for about 30 minutes, we’ll get you drained and milked and then you can go about your day. The best part is there’s no drama with an orgasm, just this constant drip fed pleasure.” Matilda couldn’t help but enjoy torturing David. She loved her job. David’s drip became a steady ooze of cum as Matilda pummeled and squeezed his bud. His eyes rolled back and drool escaped his lips as he chased the final release that would never come. The pool of cum on the carpet slowly stopped growing.

“All done!”

“What?! No please.” David begged, the dildo still embedded in his hole. Matilda got up and David awkwardly tried to follow but collapsed in the puddle of his own making.

“Be a good boy and drain yourself if you have to okay?”

David lay there still contemplating if he would as Matilda walked out the door.