Funnel Ch. 02

It was perhaps about 5am when Thomas awoke to see his mother standing over his naked form and staring at the dried semen on his window. She shifted her gaze to her son.

“Where are your pajamas? Why are you naked on the floor… and for gods sake what is all this sticky stuff on your window?”

As she watched the red fill his cheeks with shame it all clicked into place. She tugged indignantly on the hem of her skirt as if to protect herself from her own son’s perverted look.

“Put some clothes on and come down for breakfast. Its time to start your paper-route.” She left without saying anything further about the incident.

Audrey Green was putting some things away in the hall closet when she heard the paperboy coming up the stairs to her porch. She smiled slightly as she closed the closet door and came into the living room to greet him. Opening the front door, she found Thomas just pulling her paper out of his bag.

“Why, hello Thomas. You seem earlier than usual today.” He blushed and looked down at his shoes.

“Hi, Ms. Green. Here’s your paper.”

She took it from him and held the door open.

“Thomas, why don’t you come in for a bit. We can chat for a while since you got such a nice head-start on your route.”

The younger man shyly nodded and followed her inside. He sat at the kitchen table while Ms. Green made some lemonade at the counter. He studied her ass as she bent over for a pitcher. He could see the slight lines of the legs and waistband of her panties through her skirt. And just like that…naughty Thomas had a boner. He reached down with one hand and tried to rub it a bit to make the pressure not so hurtful… it was wrapped painfully around one of the leg openings of his white cotton briefs and as it tried to stiffen it goaded his sore penis. Ms. Green turned and caught him rubbing.

“Thomas, is everything ok?” He blushed deeply and asked to use her bathroom. Audrey gave a knowing smirk and pointed to a room off the hall. He shuffled off to the bathroom, closing the door and pulling his pants and down. He knew he had to be extra careful, as this door didn’t have a working lock. He decided to just pull his cock out through the opening in his briefs to wank it.

In the kitchen Audrey was laughing softly at the too obvious slapping sounds coming from her bathroom. Despite what the paperboy thought, he was making quite a lot of noise in there and the sounds were unmistakable. He was beating off in her bathroom, Audrey thought with a grin. This had never happened before in all the times they had chatted. Audrey’s mind filled with the image of Ms. Fortune milking the sperm from her pet pervert’s leashed balls. She ran a hand down to her thigh and traced the garter strap there. She had dressed up special for Thomas today. She intended to tease him with the mixed messages of her otherwise conservative attire mixed with the mature feminine appearance of an old fashioned garter and stockings.

She got up from her chair and slowly walked over to the bathroom door. She pressed her ear to it and was greeted with the telltale heavy breathing and ball slapping that accompanies masturbation. She took her ear away and addressed the door:

“Thomas. Are you going to be much longer, dear?” She tried to hold her laughter.

There was a startled gasp followed by the rustling of clothes.

“N-no, Ma’am. Just finishing up.”

A moment later Thomas opened the door looking flushed and nervous as he practically walked into Audrey standing in the bathroom doorway. There was a terribly accusatory moment of silence as she slowly glanced down at his crotch. He hadn’t managed to zip up properly and the zip had caught in the material of his white briefs.

“Ohhh…” she cooed, “let me help you with that.”

She had him stand in front of her while she sat in a kitchen chair. She raised the hem of her skirt slightly enough to show the darker banded tops of her beige stockings and the little clasps that cinched them to her garter belt. She drew Thomas closer and wrapped her stockinged legs about his own to keep him in place.

“My, my, my… got your underpants in a bunch, huh?” She chuckled.

Thomas was very nervous. He hadn’t cum yet and his balls felt heavy with sperm. He saw that Ms. Green was wearing those kind of stockings that Ms. Fortune always wore and his penis stiffened up slightly. It was an easy matter for Audrey to pull the underpants out of his zip but she handled the wadded material for a while. She pulled on it hard and the young mans dick was forced down one leg opening. She easily made out the shape of his boner as it throbbed against his pant leg. Still tethering him to her with his briefs, she slowly brought her hand up to caress the fattened head. Looking up at him in mock innocence, she asked: “Whatever is this, Thomas? Hmm?”

When he began to stutter incoherently, she laughed and let go of his briefs. He quickly zipped up and said he had to go. Audrey just continued to laugh as she nodded her understanding.

With the reverence of a monk, he quietly ascended the steps to Ms. Fortune’s front door. He felt around for the key, found it just where she said it would be, and entered the house. It was quiet inside and he felt like an intruder. He quickly fished out her newspaper and left it on the dining room table per her instructions. Then, he heard that awful sound… like a wounded cow “mooing”. There were sharp smacking sounds and even sharper admonishments being delivered in a firm female voice. It all seemed to be coming from upstairs. Remembering the bizarre show from the previous day, he had to follow those sounds. There was a sinister cadence to noises. They were almost… rhythmic. He slowly climbed the stairs that led to the upstairs and noticed to his good fortune that the far bedroom door was slightly ajar. He could now clearly make out the woman’s voice.

SMACK!
“You do! You do as I say! Hump!”

There was quiet for a bit, save for the dirty sounds of oiled skin rubbing hard against something and labored animal grunts.

SMACK!
“Hump it!” A pause. “Can you hear him? What he does now for me?”

Thomas froze in his tracks, terrified that Ms. Fortune was addressing him through the door. He peered ever so slightly into the room and saw that she was actually speaking to someone on her phone. The phone was in one of her hands and it was being held down closely to the greasy cock of the man he had seen before. She had bound him to some kind of wooden frame and held his penis in one greasy fist. He was fucking it for their entertainment like a circus geek.

Despite his revulsion at the terrible sight, his own penis was getting stiff again. He watched the hairy brute rut into his Mistress’s oiled fist. The man was sweaty and dirty looking. He was wearing some kind of leather helmet that covered his entire face. She was laughing at the spectacle he made, and brought the phone back up to her face to speak.

“Do you hear? Yes, he makes sounds like animal. He make big mess soon.” More laughter.

There in doorway, Thomas decided he had to masturbate to this. He was not particularly strong-willed to begin with and this was proving way too much for him. He carefully unzipped his pants and extracted his cock from the opening of his white cotton briefs. He whacked it in time with the forced handjob being performed on the man in the other room. His balls gently beat against his fist as he dragged it up and down his erection. He felt like he could actually cum at any minute, as he had been aroused since the time he had spent at Ms. Green’s. Suddenly, he fell forward a bit and the door opened fully, exposing him.

“AH! What you do?! Why you spy on me?”

Ms. Fortune seemed furious. She spoke into the phone.

“I have to go. The paperboy is here. I will callback.” She hung up and stood looking at the pervert in her doorway with his cock sticking out of his underpants. Her other hand remained fixed in a circle as the greasy penis of dickhead shoved in and out of it without interruption.

“I.. I’m sorry, Ms. Fortune. I didn’t mean to…”

She silenced him by holding up her free hand and shushing.

“Shame on you! Playing with yourself and spying on me! What am I going to do with you, eh?”

Thomas’ cheeks burned with shame and he hung his head. He knew what he had done was bad and now this exciting woman was angry with him. He only wished he could make it all better.

“I call your mama, no? I tell her what you do… dirty boy?”

He grew fearful of the threat and started begging. “Please, Ms. Fortune, no. I am so sorry.”

The older woman rested a hand on one hip while the other was still being fucked by the penis of her naked male. She seemed to be thinking… considering what her options were. The silence in the room emphasized the squishy jacking sounds of the pervert that she milked. She felt that she could probably make this young man do just about anything for her right now. Then, she remembered the condom.

“Come in here Thomas and undress for me.”

He shuffled into the room looking for all the world like a naughty little boy. His pants were at his ankles, hobbling his movements. He slowly undressed before her as the man in bondage continued to be milked. His big penis was so hairy and so were his balls, Thomas thought. With the last item of clothing removed, he stood naked before Ms. Fortune. She smiled wickedly as she made him turn around and show his bare ass to her. She made him wiggle it back and forth for her like a dog. Then there was a strangled whimper as her milking hand abandoned the big cock. She gave him a couple of harsh spanks to his bottom for his outburst and turned her attention to her naughty neighbor.

“You play with yourself so much, yes?”

He nodded his head stupidly, unable to say the words.

“And you cum so much, yes? All over?”

He nodded again and she laughed out loud in his face.

“You are so dirty. Dirty, dirty, dirty. Like dirty little boy you play with yourself and make big mess.”

She walked to her nightstand and retrieved several items. One was a leather strap, which she proceeded to bind his wrists with behind his back. The second was a smaller leather strap, which she fastened about his naked balls. There was a leash attached to the ball collar, like the one he had seen on the man when he had been masturbated. And of course, there was the fat, bloated condom. She gave a sharp jerk on the leash and issued her first command.

“Down! Kneel down!”

Knowing he didn’t have much of a choice, Thomas sank to his knees on the wooden floor. He knelt in front of the woman who now controlled him by his balls. She regarded him for a bit and playfully waggled the leash to make his scrotum bob and dance for her. Then she sat down on a nearby chair and proceeded to remove one high heel shoe. The large dark toe reinforcement of her stocking came into view and she wiggled her toes allowing them to air out beneath his face. The odor was strong and made Thomas’ cock begin to grow. She brought her stockinged foot down between his legs and playfully slapped at the head of his penis with it. The silky stocking felt sooo good to him down there. Then, she gave another sharp pull on his testicle leash and ordered him to tilt his head back. Slowly, Isabella Fortune began to dangle the full condom over the young man’s face.

“You open your mouth for me. Wide open for me. Do it!”

He did and she began to pour the thick cream into his mouth directly from the used rubber. He gagged slightly but his own little penis was an angry red and throbbing under her playful stockinged toes. Some of the sperm dropped down in heavy globs to spatter thickly onto his upturned face and hair. She used two fingers to help the remaining semen out of the condom and into his mouth. All the while, she cooed to him and chuckled softly at the sight he presented. She could see him swallowing the nasty stuff down in big gulps. When the condom was completely empty, she praised him like a dog and ruffled his hair.

“Ah, you make mama very happy. Such a good boy!”

He could still taste the sperm in his mouth and glanced over at the man’s enormous, hairy sac where all that nastiness had come from. He gave an involuntary shudder and began to ejaculate all over Ms. Fortune’s pretty stockings. He grunted like a pig as she laughed and laughed very loudly at him.

“Oh… you make such a mess like a dog. Shame on you.” She chuckled at him and tugged rhythmically on his ball leash to urge him empty.

His cock gave up its remaining spurts under her cold scrutiny. She continued to laugh as she brought her stockinged foot up under his penis, pinning it to his stomach and smearing his cream around into the fabric with a firm rubbing motion.

When Thomas got home from his paper route, his mother called him into the kitchen. He submissively entered and found Ms. Green already sitting there drinking coffee. She smirked at him as he entered.

“Ms. Green… um…hi.”

“Hello, Thomas. I was telling your mother about your bathroom break at my home this afternoon.”

He was horrified and his face turned scarlet. She continued.

“You remember. How you helped me fix that pipe under the sink?”

“Oh! Yes… uh… yes, that.”

She went on, explaining to his mother while her eyes never left his. She was enjoying his embarrassment immensely.

“Thomas seems very good at getting down on his knees and handling pipes.”

The double-entendre was completely lost on his mother. “Yes. I should put him to work doing that more often. Its good work for a young man.”

Ms. Green smiled at him from the rim of her coffee cup. His mother went on to explain the real reason for Audrey’s visit.

“Thomas, Ms. Green said she has chores that she would like you to do around her house. I don’t see any problem with that. You can do them after you finish your route. Ms. Fortune is your last stop and then you can go over to Ms. Green’s to assist her.”

“Sure, mom… I guess that would be alright.”

He would have popped a boner at the prospect if he hadn’t already been so thoroughly milked by Ms. Fortune’s stocking feet. He watched Ms. Green’s pretty hand glide down to covertly play with one slightly exposed garter strap under their kitchen table and he practically swooned.

Um… I have to go to my room. It was good to see you again, Ms. Green.”

When Thomas got to his bedroom he gingerly removed his trousers and underpants. His ass was still red and sore from the spanking he had received from Ms. Fortune after he had messed her lovely hosiery. She had cursed prettily at him in Italian as she had done it. There was something very refined and lady-like in everything that she did. Even when she was spanking him, he felt like he absolutely deserved it. He was quickly becoming overwhelmed by these new turns of events. He carefully crawled under the covers, naked and fell into a fitful sleep.