Chapter 4
by Lossleader2
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Afterglow
David followed Matilda out the door to the guest bedroom still in a daze from what had just transpired. He had had kinky sex before, or so he thought, but that was unlike anything he’d experienced. He watched Matilda walk about as if nothing had happened, if not for her short skirt and messy hair David would have never thought anything was off. She was very attractive and the way she had practically begged him to fuck her was also a new experience. As he started to think about the odd dynamic she had with Nancy he realized they had entered a drawing room. Matilda had grabbed a sewing tape and had walked over to him.
“I’ll just be a moment.” She said matter of factly. She then bent down and began taking measurements of his groin. She wrapped the tape around his balls, extended it to measure his dick, and checked his waist. She wrote a couple numbers down.
“Wait here.” She said briskly.
“Wait, are you okay?” He asked sheepishly.
“Of course! Miss Remington has asked me to set you up with a parting gift and I will be right back.” She smiled professionally.
“That was really fun.” He prompted.
“Uh-huh.” She said and walked out.
David stood in the drawing room naked and confused. He had wanted to have sex with his host and had spent the whole encounter thinking about her smooth thighs, big tits, and toned ass. He almost didnt enjoy his time with Matilda who he now realized was almost just as attractive. He still hoped to have a chance with Nancy.
Matilda returned after a few minutes holding some odd looking equipment. Nancy walked into the room wearing a bathrobe that barely hid her figure.
“I apologize for the lack of communication. I don’t have sex on the first date, you must understand, but I didnt want you to leave unsatisfied. That said, if you’re serious about dating me I can’t have you running around on me.” She smiled at David and his nerves flushed away.
“I wouldn’t do that.” David said weakly.
“Oh I know, but a lady can never be so sure with you handsome men.” She patronized him but he didn’t catch on. “If you are serious you will wear this special piece of clothing until our next meeting.”
Matilda held up what David was now understanding to be a chastity device. It was silver metal and looked quite small.
“I’ve never worn one before. Won’t it be uncomfortable?” David was unsure.
“I’m not sure, I’ve never worn one.” Nancy laughed. David laughed along nervously. “You dont have to wear it of course but I don’t think I can continue this if you don’t.” Nancy knew this was a crucial point. “I’ve had bad experiences in the past.” She added, lying.
“I can try it I guess.” David thought to himself that he would take it off as soon as he was home.
“Perfect. Matilda.”
“Yes mistress.” Matilda knelt down in front of David and slid his cock into the small space in the chastity device. She strapped the rest at the base of his scrotum and cinched it down. She then clicked the strap in place and put a small padlock into its housing, sealing it with a key. His balls felt slightly crushed and his cock was scrunched into the small space.
“I think its a little tight.” David complained.
“Perfect, then it fits.” Nancy said. She walked over to David and put a hand on his chest, kissing his cheek. She smelled amazing and he could feel himself getting horny again. This came with a considerable amount of discomfort. The walls of the cage felt like they were **** his member, he winced.
“Aww, I can tell you’re feeling the snugness. I’ll be out of town for the next couple of weeks but when I get back I would love to see you.” Nancy said with a bright smile.
“A couple of weeks!” David wasn’t sure he could wear this that long.
“Don’t worry, I’ll send Matilda by to check on you next week.” She winked. Matilda didn’t react but smiled professionally.
“Can I have the key at least?” David asked weakly.
“Ha ha no of course not! What would be the point of that. You could just put this back on right before you see me. I want you to save up all of that juice for me when I get back from my business trip.” Nancy rubbed his balls and then began to walk out. “I look forward to our next date.” And like that she had left.
The next few hours were a blur as David put on his clothes over his shackled manhood and got in the car with the butler. He drove David directly home.
“Have a good day sir.” The butler said politely as they arrived at his apartment.
“Is this always how she does things?” David asked incredulously.
“I’m not sure what you mean sir.” The butler avoided the question.
“Sorry, I guess I assumed everyone was part of whatever this is.” David said ashamed for asking.
“If you don’t mind my saying so sir, Ms. Remington seems to have taken a liking to you. It’s rare that she is so invested.”
“Thanks.” David exited the car feeling a strange and a little excited. The cage was uncomfortable when he was turned on but right now it almost felt like it wasn’t there. He could last a few weeks like this. He hoped.
——————————————
Nancy was beside herself with excitement. Her first conquest had gone better than she could have hoped. She had been a little disappointed in the brute **** she had used to get what she wanted but the results spoke for themselves. He was a promising prospect and all she had to do was wait. In the meantime she would make preparations for her next catch.
The next few weeks saw Nancy going on similar dates. She sought prospects similar to Davids temperament. She started off meeting then in the same area but realized quickly that this opened her up to being seen by her other prospects, so she opted to find men in different neighborhoods. The next few dates were not stunning successes. Most of the men were too timid or sure of themselves to be of any use to her. The string of bad dates had her frustrated. She did meet one man of interest. He was an artist who worked with acryllic paint. He had dark skin and a nice haircut and had impressive style. He wasn’t the type she was looking for since he had a large frame and was well toned. They talked longer than she normally would and she found his conversation different from the rest of her candidates. She let her frustration get the better of her and let him take her back to his studio. His art was beautiful and she bought a piece after he bent her over the couch. He had been tender but dominating and his cock was almost uncomfortably large. He held her hips as he fucked her deep. She gave herself up to him and relinquished control for the night. She came after the first few minutes and offered to return the favor. His cock felt warm in her mouth and she could taste herself on him. She snuck two fingers underneath his legs as she sat between his legs at the foot of the couch. She toyed with the rim of his ass and he began to moan a little. She sucked on her fingers and began to dive for his prostate. She pressed deep and was surprised how easily he let her do it. After only a few minutes of this she was milking his cum into her mouth, pressing out with her fingers and gulping it down. She swallowed his milk and licked from the hilt to the tip, squeezing every last drop that she could.
On her way home she regretted letting him have that power over her but saved his number just in case she needed to relieve some stress.
———————————————-
David was growing ****. His manhood had been strangled by the cage over a week now and he could barely think straight. The slightest glance at woman had his cock pressing against the cage like a wild animal trying to break free. His balls had grown too, filled with his unspent fluid. Every day at work all he could think about was Nancy Remington and her smooth skin, her toned ass. He had help off this long without contacting her but couldn’t wait any longer. He texted the number that Matilda gave him.
David: Hey Nancy, I hope your trip is going well! Let me know when you get back, would love to meet up!
Nancy: Hi David! I’m still on my trip, Ive been thinking about you and your little predicament and I feel so bad :(
David: It’s okay! I am definitely feeling pent up…
Nancy: Do you want me to send Matilda by to check on you? I probably won’t get back until next weekend.
David could not imagine going another week like this and the thought of getting a chance to blow off some steam with Matilda was too enticing to pass up.
David: If she’s around I wouldn’t mind meeting up with her to talk…
He wasn’t sure how to approach this but his desperation had completely overridden any weirdness he felt about the situation.
Nancy: of course! I’ll have her swing by around 8 tonight ;)
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Harem house
A mifls harem house
Nancy Remington comes from old money and says she lives alone. The truth is that she lives in a mansion filled with men she seduced into becoming her playthings
Updated on Jun 4, 2024
by Lossleader2
Created on Dec 6, 2023
by Lossleader2
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