Cheri's Ordeal

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Transsexual receives a severe whipping.
2.6k words
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Cheri knew that she had made an error in not following Ken's instructions. She felt that she would be able to do as she pleased while at home alone. That, of course, included the right to masturbate at any time. After all, she had been beating off several times a day since her early teens. To be ordered not to was unimaginable to her. She was about to pay for her stubborn actions.

Ken had walked into the bedroom as she stood wearing her panties and high heels posing in front of the full length mirror. Even though she was a transsexual, Cheri had retained the capability of regular ejaculation. The panties had been lowered to mid thigh and she was a few strokes away from orgasm. Her eyes had just closed in ecstasy as he entered. She moaned and shot her load against the glass in the same instant she became aware of his presence.

"So. You deliberately disobeyed me, Cheri. That is not a good sign."

Ken's hand gripped her by the back of the neck and pushed her to her knees.

"Lick your come off the mirror. Now!"

Cheri was stunned. Too stunned to disobey, she cleaned off the glass and swallowed her own ejaculate.

The next moments were a blur as she was hurried out of the bedroom and moved rapidly to the spacious basement. Walking with panties at half mast was embarrassing and awkward. The extremely high heels made it even harder.

Her panties were jerked down to her ankles and her hands bound tightly and extended full length over her head. Ken took a thin leather collar and fixed it to a bolt in a steel post. He repeated this with a belt around her waist. Her naked buttocks were pressed against a cold steel plate. Her could not move in any direction. She shivered at the touch of the cold metal. Her testicles tightened, but to her own amazement, her penis was stiffening.

Ken stepped back to survey his handiwork.

"And now, Cheri, it is time to learn a lesson in obedience. You were told to refrain from handling your own penis unless I instructed you to do so. Isn't that correct?"

Cheri had a few tears starting to smear her eye makeup and meekly said nothing.

Ken's hand slapped her face once spinning it against the pull of the leather collar.

"I spoke to you, Cheri. I expect an answer."

Cheri croaked a yes. She received another slap.

"What were the exact words I used? Exactly!!"

"I .l . .think you said never to touch my penis unless you gave me permission."

"Yes. And what were you just doing?"

"I was beating my meat."

"Yes. You were beating your meat like a teenage slut."

Cheri was almost horrified to realize that she was now fully erect.

Ken stepped back and observed her erection. He took it in his hand gently and stroked it up and down. The without warning, he released it and gave it a powerful slap causing it to vibrate wildly back and forth. Cheri tried to move but was totally fixed in place. Ken slapped it again, then gripped it firmly.

"I'm going to slap your miserable little dick until it squirts its load, Cheri. Your cock will be too sore to touch once I'm finished with it."

"Please don't."

His response was to deliver another firm slap. He repeated this several more times.

Cheri's balls tightened even more and sobbed as she suddenly felt herself prepare to shoot her load under the barrage of stinging slaps. She stiffened and groaned as her penis throbbed and twitched. She dry pumped once and then a jet of drool spit out dropping onto the floor beside Ken's foot. She quieted herself as several more wads followed until, at last, the semen drooled out onto the end of her rapidly shrinking and very sore penis.

"You surprise me, Cheri. Shooting again so soon. And the evening is only just begun."

Ken took her face between his hands and kissed her gently on the mouth. He moved back slightly and whispered. "You were a bad girl, Cheri. You've made a mess on my floor. What are you going to do about it, hmmph?"

Cheri was breathing hard and looked at him with pleading eyes through her tears. She knew she would have to kneel down again and lick up her come.

"Well, Cheri, I'm waiting to hear something from you."

"I'll . . . I'll clean it up with my tongue."

"Yes, darling you will. But just before you do, I need you to suck my cock."

He released her hands and unfastened her from the post. She sagged to her knees. Her arms tingled as the feeling started to come back into them. Ken put his hand under her chin.

"Take my cock out and suck it."

Cheri obeyed. At least this wasn't painful. In fact, she loved to suck his cock. She had diligently taken it in her mouth a number of times over the last few days. Each time she had nearly come herself as his penis jerked inside her mouth, spilling its delicious come right to the back of her throat.

Now, unfastening his pants and reaching in to get it out, she quivered with anticipation. He was already rock hard. Ken's penis was of decent size, if not huge, and it filled Cheri's mouth as she rose over it and let it plunge in. Now he relaxed and didn't budge, making her move her mouth the full length of it. It's heat seemed to rise as her lips tightened over the head. His nuts contracted and he began to grunt with each loving suck. Cheri felt his hips move slightly and his pelvis push forward. She let her fingers gently scratch his balls the way he liked it. He began to fuck her mouth, now, not caring if he rammed it down her throat.

"Suck my cock, Cheri. I want you to swallow my load."

Cheri felt her own organ stir at the sound of his mounting passion. Ken's hand moved to the side of her face and caressed her cheek as it hollowed with each long stroke. Finally he took her head in his hands and drove his cock into her mouth to the balls and flooded her with semen.

"Suck it!"

Cheri felt the discharge flood her throat. She almost gagged as wad after wad spit down her throat. As his thrusts slowed, Cheri made up for the movement by bobbing rapidly up and down over the full length draining every precious drop. She held his cock firmly in her lips. It was still fully erect. Finally, he pulled her face away from his prick.

"Now, clean up the mess, Cheri. Now!"

Startled, she obeyed immediately. His foot was inches from the puddle of her own discharge, and she felt the leather of his shoe against her cheek as she licked the semen from the floor. Ken squatted down over her and whispered.

"And now it's time for your punishment, Cheri."

Ken pulled her up. He took a moment to gently fondle her tits. They were firm and lovely as only those of a young transsexual could ever be. He tweaked the nipples the way that Cheri loved. He then got down to business.

"Bend forward. More! I want you facing your own prick as I punish you."

Cheri was pressed down further until her head was nearly as low as her knees. Ken snapped manacles around her wrists and pulled her arms upward, back over her shoulders and secured them from a suspended hook. He slid a steel bar across her neck that was secured through two eyebolts then pulled a leather strap beneath her chin and secured her firmly against the post.

Next he knelt beside her and whispered into her ear.

"I love to see you like this. Bent over with your beautiful ass pushed up for me."

He stroked her ass very gently as he continued to speak. Cheri had an extremely pale complexion. Her ass was deliciously white. It would make for a startling contrast.

"I'm going to use the thin leather strap to begin with, Cheri. I'll take my time and make sure I get your ass completely red. But first I want to make sure your little nuts are taken care of."

Ken took a small soft leather pouch and gently eased Cheri's sack into it. The pouch had a leather string which he used to secure her balls tightly up against her cock now pressed against her stomach. To complete the bondage, he used a special block of metal to separate her ankles by 3 inches and tied her rigidly to the floor. This left her free to move anything between the tightly bound neck, wrist and ankles during her punishment. However, any motion other than side to side would be horribly painful.

"Now, you're ready for the first session, Cheri. I'm going make sure I make this last for you."

Cheri did not want this to last at all. Her position was very painful, and she was getting red in the face.

"Please, I feel like I'm going to be sick."

"Just more mess to clean up, if you do." No sympathy in his voice.

"Let's get started, my dear."

Ken drew back the thin strap and administered a firm sharp CRACK across Cheri's left buttock that was angled to catch her inner thigh.

"OUCH! That hurt. Please stop!!"

Ken repeated the blow without response adding an extra amount of effort. Cheri screamed again. 10 more stinging slaps started to bring up the delightful livid colour in Cheri's small white buttocks. To Cheri's surprise, she felt Ken's hand slowly stroke her flaming cheeks.

"The colour is lovely, Cheri. Too bad you can't see it yet."

He proceeded to deliver another 10 in fairly rapid succession.

"Now the colour is getting deeper, darling. You should now feel a true glow through your lower body."

Cheri was whimpering by now, her entire torso alive with the pain. Ken released the bar over her neck and Cheri was able to rise awkwardly to get her head above waist level for a few moments.

Her arms were still rigidly held up behind her and the new position put extra strain on them. Ken put his arms around her and pressed his erection against her hot cheeks.

"I'll fuck you in the ass later, Cheri. Here. Let me press it against your shit hole as we speak."

He spread her cheeks with his cock head and guided it directly against her asshole.

"That's where it's going. Right up your ass."

He pulled away and forced her head back down and locked the bar over her neck. He quickly lashed her 6 times to get the red colour back, then slowed down as he let the strap crack across her buttocks another 30 times, catching the upper and inner thighs. Cheri was in tears as Ken released her for another few moments.

"Time for a fuck, Cheri."

Ken guided his erection against her asshole. He had used lubricant on himself and dipped his finger into her stretched hole to assist the penetration. With a single thrust he drove into Cheri right up to his balls. Cheri groaned. Her legs were quivering and she felt sick. He didn't stop. He pulled back and drove it in again. Her blazing cheeks were spread flat with the force of his stroking. Ken took a long time to finish the fuck. The previous ejaculations made it a very long process to build up the load that was now prepared to surge into Cheri's gaping shit hole. He began to stroke faster. Each stroke caused Cheri to cry out with a mixture of pain and pleasure. She loved fucking, but the associated feelings were confusing her. Sudden she realized that her tightly bound cock and balls were aroused. Her prick, stretched tightly against her belly was so hard she thought the skin was going to split. She felt her sore prick ready for a discharge. How could this pain allow her to shoot off? Her mind stopped thinking as her anus went into spasm. Ken was rammed so deep into her asshole that she felt it in her chest. He was starting to shoot his load. Her own prick started to pump. They were making it together. She felt saliva drool out of her mouth and she shrieked at the intensity of the ejaculation which shot along her belly for several inches before hitting the post below her head in a beautiful parabolic arching shot. Ken's load was so far up her ass that she knew she would be shitting sperm all night.

Ken took his cock out of her slowly. He caressed her body and carefully released all the bonds. Cheri sagged into his arms weeping. He held her for a moment.

"Cheri, my sweet young girl, all this emotion and we have only begun your punishment."

"Oh, Ken, I can't take any more."

"Cheri. You can and you will. Now it's time to clean up my prick."

He let Cheri sag to her knees, her face slumped against his waist. His shit stained prick awaited her attention.

She had vomited into the toilet several times after the last session. Ken stood unmoved over her shuddering body. Cheri was confused by her reactions. The pain was so alive and yet her cock had betrayed her. She had blown her load several times while her cock and ass were on fire. And she knew that when he took her back to the whipping post, she would get hard all over again. She felt fear-not of the whipping, but of herself. How had it come to this? She was a sick puppy.

"It's time to get started again, Cheri. On your feet."

Cheri wobbled onto her high heels and staggered back out to her punishment rack. She stared at Ken with loving eyes in spite of the throbbing pain in her ass. She knew she would love to have his cock driving up her ass again right now. If only he didn't whip her too hard. Foolish girl.

"Now. Stand with your hands over your head and don't move them. I'm going to use the dog whip to remind you that you are a bitch in heat."

Cheri could barely get her hands up. The whip lashed her thighs savagely.

"I said get your hands up."

Cheri tried to crouch down, but was rewarded with two harsh strokes across her exposed ass. Ken gripped her wrists and hauled her up. He fastened her with leather thong and yanked her into an upright position almost off the ground.

"Oh, God, it hurts."

She yelped as the whip bit into her buttocks again and again. As Ken paused and let his hand caress her tits, Cheri's cock reached its full rise and bobbed up and down with each twist of her nipple.

"Should I lash your little prick, Cheri? Or should I just whip your thighs?"

He smiled letting his whip ride against her tiny balls.

"Maybe these little acorns need some attention?"

"Not my balls, Ken. Please don't do that."

"Cheri, no just doesn't work for you. I said no to you and you ignored me. Why should I pay attention to you?"

She flinched as Ken flicked the short whip upwards between her legs.

Cheri's scream reached new heights. He flicked again and her voice rose in pitch and her head slumped forward. Her cock sagged to rest.

Ken went behind her and worked her ass over with 10 or so more laser sharp cracks.

He then eased her down onto the floor and pissed directly onto her blazing ass.

"Once you get all this cleaned up, you can crawl back into my study and suck my prick again."

He left her nearly unconscious on the floor knowing that she would recover fairly soon, especially with the prospect of a mouthful of come in the offing.

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AnonymousAnonymousalmost 13 years ago
straight desire

just stokin to your story..

straight but getoff on thinkin about gettin in ass ..

deep and hard..have had some play...

w/gloves and strapon...fantsize about more...

anyhow thanks and would like to read more..

studrox@yahoo.com

AnonymousAnonymousover 19 years ago
wow

wonderful. this is the best punishment story i have ever read. my man clit is hard as a rock. i wish i could meet a man or several men who would treat me like this everyday.

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