It had been almost a month since Trudy’s first foray into the exciting world of dominance and submission and she and Mr. Wilson had enjoyed adventure after adventure. Trudy had found a whole new level of excitement in surrendering herself totally to her lover’s desires. Just putting on a blindfold was now enough to cause her pussy to literally drip with excitement. Mr. Wilson had tied Trudy in a number of different positions each more exposing than the last. She had enjoyed being bound to her bed on her back with her hands fastened to the headboard and her ankles spread to the bottom corners.
A variation on this had Wilson bend her knees and tied them wide apart to the sides of the bed thus opening her slit wide apart.
One night Mr. Wilson had blindfolded her and had tied her standing with her hands pulled toward the ceiling. Her ankles were also tied wide apart. It had been her favorite position so far. Standing there with her breasts pointing proudly forward, she had imagined herself on display as though at a slave auction from a bygone era. (And what am I bid for this fine specimen). Mr. Wilson had left her like that for quite awhile and had brought all of her senses to a fever pitch by slowly and gently rubbing warm oil over her entire helpless body. He had finally taken her, still standing, until they both cried out in orgasm. Trudy had such a powerful orgasm that she just hung weakly in her bonds, trembling as tears streamed down her face.
Last weekend, Mr. Wilson had put her in what was, by far, the position that Trudy felt most vulnerable in. On Saturday night at his home, Mr. Wilson had blindfolded her and then undressed her completely. He led her into the living room until she felt the cold leather of the back of his easy chair touch her thighs. Wilson had attached the, by now familiar, straps to her wrists and then gently pushed her forward until she was bent double with her head touching the seat.
Wilson had tied her wrists to the arms of the chair and then spread her feet and fastened her ankles wide apart. He had left her like that for a long time before finally touching her and by the time he did Trudy was soaked. She had imagined what she must look like from her boyfriend’s vantage-point. Her long tanned legs were stretched tight down and wide apart. Trudy could feel a faint breeze between her opened thighs and knew that Mr. Wilson had a perfect view of her blond pussy from behind. She was sure that he would be able to see her juices on her puffed out slit. Trudy had pictured herself in Mr. Wilson’s position and realized that her bottom was stretched tight across the leather chair and her buttocks were opened wide apart exposing her anus. Trudy felt herself tremble as she wondered if Mr. Wilson planned to touch her there.
Trudy had always considered that part of her anatomy to be private and had never let any of her lovers touch her there. She was somehow embarrassed when even she touched her herself. It was kind of naughty to finger her bottom but whenever she did it was the most exciting thing ever. Now, here she was, bent over, helplessly exposing her bottom to her lover. Wilson’s hands had finally touched her. Starting at her ankles and trailing up the backs of her calves to her knees and then up along the insides of her thighs to her blond bush now wet with her own juices. Trudy shivered with delight as she remembered how Mr. Wilson’s fingers slid down from the small of her back through the valley between her buttocks. Trudy gasped as his fingers had crossed the sensitive opening of her anus. Trudy still wasn’t sure if she was disappointed or thankful that he hadn’t lingered there. The sex that night, with Mr. Wilson taking her while she was still bent over the chair, was the best ever.
That had been last Saturday and now, here it was Friday morning and Trudy hadn’t seen Mr. Wilson since. Each night when they talked, Mr. Wilson promised to outdo himself next time.
“When?” had asked Trudy
“When it’s time.” had said Wilson with a smile.
Trudy had waited anxiously each night for Mr. Wilson to start an ‘adventure’ but each night their talk was pleasant but decidedly asexual.
Trudy was getting ready for work when the phone rang.
“Hi.” said George Wilson “Are you ready for an adventure?”
Trudy giggled “Yes Sir”
“Good girl.” said George “Have you dressed for work yet?”
“Not yet.” replied Trudy
“Okay I want you to dress in a short white skirt. Wear the pleated one that goes about halfway up your thighs. Wear the pale blue cotton blouse with it. Pick out a pair of heels too. Oh, and there’s to be no other clothing; no panties, no bra, no stockings, nothing. Plan to spend your lunch hour at my office. Take a cab so that you’re there by 12:15. Any questions?”
“Good. See you later then.”
Trudy pulled the clothes Mr. Wilson had asked for out of the closet and jumped into a quick shower. As she dressed, she could feel her excitement building. She was sure she’d be soaking wet by lunchtime. ‘What would he do to her this time?’ she wondered, ‘Would he tie her up in his office?’
What excited Trudy most is that she had no idea what would be demanded of her just that she would have to obey him. The morning at work seemed interminable. Trudy kept looking at the clock and willing it to go faster. Finally noon arrived and Trudy was out of the building and into a waiting cab by 12:01. During the 10-minute ride, she thought over and over again about what might happen. She felt her heat rise as possibility after possibility ran through her mind. Trudy paid the driver and hurried into the tall office building where Mr. Wilson worked. A few moments later, Trudy exited an elevator on the 23rd floor. Mr. Wilson’s office was down the corridor. Trudy took a deep breath before opening the door and walking in.
As usual, Mr. Wilson’s receptionist Kathy was in the lobby. Kathy and Trudy had met a number of times. Kathy smiled as she walked in.
“Hello Trudy. Mr. Wilson said to give this to you and to have you wait for him in his office.”
The pretty young receptionist handed Trudy a large envelope. Trudy looked down and saw the word ‘Instructions’ printed on the envelope in Mr. Wilson’s handwriting. She looked up to see a knowing smile on Kathy’s face. Trudy blushed a deep red in embarrassment as she realized that Kathy now knew that she was submissive.
Trudy quickly moved into Mr. Wilson’s spacious office and closed the door behind her with a sigh of relief. Mr. Wilson’s office was luxuriously furnished. His large oak desk was at one end. At the other end were a small conference table and a small sofa. The office was covered with wall to wall carpeting. Trudy sat down at the conference table and opened the envelope. Inside were a black silk scarf and a letter. Trudy’s heart quickened as she picked up the note.
Mr. Wilson’s instructions were simple and to the point. Trudy was to remove all of her clothes immediately. She would then stand in the middle of the room and put on the blindfold. Then she was to stand with her feet apart and her hands clasped behind her head until she was given further instructions.
Trudy’s face was flushed by the time she finished the letter. Just the idea of taking off all of her clothes in Mr. Wilson’s office was terrifying but to do so in the middle of the day with Kathy right outside the door, that was even scarier. Trudy was pretty sure it would be Mr. Wilson who would come in, but there was not even a guarantee of that. As Trudy stood up she realized that, as scary as these instructions were, they were also exciting. She felt her pussy tingling with her own juices.
Trudy’s hands shook slightly as she undid the first button of her blouse. It only took a moment before the blouse and skirt tumbled to the floor leaving Trudy completely naked. She moved to the center of the room and carefully put on the blindfold. Instantly Trudy’s hearing doubled in sensitivity. She clasped her hands behind her head and waited for someone to come in. Her ears strained to identify the sounds outside of the door. The wait was only a couple of minutes but it seemed like an hour. Each time Trudy heard Kathy move around out in the lobby, she would hold her breath and pray she wouldn’t wander in with a memo or something.
The sound of the door opening finally came. Trudy felt her whole body tense. It seemed to take forever for the door to close and all that time Trudy knew she was perfectly visible to whoever might be looking in from the lobby. Trudy let out a small sigh of relief when it finally closed.
Was it Mr. Wilson who was now in the room? Even if it was, did he come in alone? Trudy listened intently as someone slowly walked all around her. She felt her nipples betraying her excitement as they stood to attention under the gaze of her admirer. Very lightly, fingertips touched the underside of her breast and slid upward to her now tight nipples. The fingers left her and then touched her again, this time sliding from the small of her back, tracing the crack between her buttocks. Trudy let out a breath that she realized she had been holding for ages. The fingertips touched here and there, each time making Trudy hotter and wetter. Finally, she heard Mr. Wilson’s voice.
“You’re awfully hot, my little sex slave.”
“Oh God… you have no idea.” replied Trudy
Mr. Wilson’s fingers moved up and grasped Trudy’s left nipple firmly. With a small tug, he pulled Trudy forward. She had no choice but to follow him. In tiny steps, Trudy let herself be led forward, the tugging on her nipples guiding her forward until she felt the cool sensation of Mr. Wilson’s leather seat on her thighs. From the height, Trudy guessed that she was standing directly behind the sofa facing forward. The fingers left her nipples and moved upward to grasp her wrists.
Her wrists were pulled forward until Trudy felt herself being pulled down across the back of the sofa. She bent forward until her head rested on the sofa back. Leather straps around her wrists fastened her hands pulling forward toward the front of the sofa. Her now sensitive nipples just touched the cool leather of the sofa back.
Trudy heard Mr. Wilson walk behind her and felt him attach leather straps to her ankles also. Her feet were pulled gently wide apart until her hips rested fully at the top of the sofa back. Her feet were also fastened in this position. Trudy’s breathing had quickened during the whole procedure and she knew she was soaking wet with excitement. She imagined the scene, as it must appear for Mr. Wilson. There she was, bent over the back of his leather sofa, her legs spread and her bottom pulled tight from the position she was in. She knew that from his vantage-point he had a perfect view of her pussy from the rear.
She was sure that with all the excitement her pussy lips must be puffed out and swollen. She tried to imagine the view from the rear and realized suddenly that her anus must be perfectly exposed also. That part of her that was so private was now completely exposed to Mr. Wilson once again. She knew that Mr. Wilson was standing or sitting right behind her, enjoying the view. She wondered what he would do next.
Mr. Wilson moved closer to Trudy. She felt his hands stroke gently upward and come to rest with one on each buttock. His thumbs slid slowly inward then gently pried Trudy’s bottom wide open stretching her anus tight. Trudy had never been so embarrassed. She tried to clench her cheeks but in this bent-over position, it was impossible. She felt Mr. Wilson blowing gently across her sensitive anus and shivered as she wondered what he might do to her. Mr. Wilson held her like that for what seemed ages before letting go. She heard him walk over to his desk and then the sound of a jar or container opening. Mr. Wilson’s footsteps moved back behind Trudy and she held her breath in anticipation.
The touch of Mr. Wilson’s fingertip directly on the center of Trudy’s anus was cold. Trudy gasped. Mr. Wilson had covered his finger in Vaseline and now he teased her rear opening, circling the center slowly. Trudy held her breath again, knowing what must come next. Mr. Wilson’s penetration of her bottom came a fraction of an inch at a time. In and out, each push a little deeper until finally his finger was embedded in her fully and Trudy was gasping with excitement.
Mr. Wilson chuckled “You like that do you?” he asked. “Well you’re going to like it more because as soon as I get home tonight I’m going to take your anal cherry. Between now and then I’m going to leave your bottom slippery for me and you are not going to touch yourself.
“You’re to be home by 5:30 and when you get in I want you to strip completely and go to the bedroom. You’re going to put on the blindfold and get on the bed. I want you on your knees with your ass facing the doorway. You’ll spread your knees wide apart then bend over until your head touches the bedspread. Then I want you to reach back and hold your buttocks wide apart for my inspection. You’ll stay like that until you’re told otherwise. Now, do you understand all your instructions?”
All this time Mr. Wilson’s finger had been sliding gently in and out of Trudy’s tight bottom, twisting slowly as it did. Trudy’s voice trembled with excitement as she answered her lover.
“Yes what?” asked Mr. Wilson softly
“Yes Sir” replied Trudy
Mr. Wilson’s finger pulled slowly from Trudy’s upturned bottom and despite herself, Trudy felt her anal muscles pulling to hold him in. A few quick moments later Trudy found herself untied and the blindfold removed. Mr. Wilson was smiling at her.
“Now put on your skirt and get back to the office. Remember what’s going to happen tonight.”
“How can I forget?” grinned Trudy as she pulled on her skirt.
As she left the office, Kathy smiled knowingly at her again and Trudy felt the heat of her embarrassment rise to her face.
The afternoon at the office was a write-off. Trudy couldn’t keep her mind on anything but the feeling of Mr. Wilson’s finger in her bottom and the thought of what awaited her at home.
Trudy made fast time getting home and arrived by 5:30. Not wanting to wait, she quickly stripped off her clothes and hung them up. With a quick look at her watch, she figured she could spend 5 minutes in a shower and did so. By 5:30 exactly, Trudy was in her bedroom, naked and on the bed. She got herself into position and put on the blindfold. As usual, the blindfold had her get even more excited. Spreading her knees wide apart, she bent over and rested her head on the bed. Trudy reached back, grasped her buttocks, and pulled them open. She felt even more vulnerable than she had at the office. Just the idea that she was holding herself open in this obscene position for her lover to ‘inspect’ her was the most naughty thing she had ever done.
Trudy didn’t have to wait long. After about 5 minutes, she heard the front door open. The door closed after a moment and she waited for her lover to come into her room to discover her. She felt her anticipation build. What would happen? She wondered. Where would he touch her first? The thoughts of what might happen next ran through her mind as fast as she could think of them. She knew her pussy was now soaking wet. She could feel each slight draft of air as it passed over her wetness. Trudy strained her ears trying to hear the sounds of Mr. Wilson entering her room. Each minute seemed like hours and all Trudy could hear was the sound of her own heartbeat racing, pounding in her chest.
The touch directly at the center of Trudy’s anus was a shock and surprise. She gasped out loud, as the tip of a finger circled the center of her rosebud. It was cold and slippery. Trudy was sure it was covered with even more lubricant. The finger moved in a minute circular motion, teasing the sensitive opening. It only took a moment and Trudy’s bottom began moving with the motion of the finger, undulating almost obscenely despite herself. The finger paused for a moment, waiting directly in the center of the opening and Trudy held her breath. It was as though time was suspended, waiting for the next movement. When it came, a moment later, it was a long firm movement. Mr. Wilson’s forefinger slid fully into Trudy’s bottom until it was embedded to the third knuckle. Trudy gasped and arched her back at the sensation of his finger penetrating her. The finger pulled out slowly only to be thrust back in again. Trudy couldn’t believe the sensations. She had never imagined she could get so hot from being touched there. Her pussy was soaking wet and burning hot. Again Mr. Wilson’s finger withdrew and then plunged into her. This time Trudy couldn’t stifle a moan at the feeling.
The finger pulled from her slowly and Mr. Wilson felt Trudy’s anal muscles pull in a vain attempt to keep his finger inside her. Mr. Wilson smiled as he watched her sphincter clench down on him. Her breathing was coming in short ragged breaths now and he knew that if he kept up the violation of her bottom any longer, she would come from that sensation alone.
Trudy whimpered softly as his finger pulled from her. Trudy waited, her back arched slightly. She knew that the position left her bottom pushed up and in her submissive position, she imagined how she must look, her bottom and pussy offered from behind to her dominant lover. She waited quietly for whatever Mr. Wilson had planned next. She did not have to wait long. Mr. Wilson’s fingers began sliding up her thigh, moving slowly closer and closer to her wetness. He cupped her mound gently with one hand and began stroking her pussy lips lengthwise. Trudy waited for him to take her there but Mr. Wilson had other plans. One finger began stroking the length of her slit, moving her juices up and across her engorged clitoris. Trudy moaned at the feeling. Suddenly, Trudy felt her anus being touched again. The feeling was cold, lubricant again she guessed. The object at her rear passage was not a finger she quickly realized it was too hard. What was it?
The plastic plug pushed slowly into her, opening her already slippery bottom. As the plug was inserted, Trudy felt it getting wider and wider. Her breathing became ragged, short sharp breaths as the plastic intruder violated her rectum. Suddenly the widest part pushed past her sphincter and the plug became very narrow quickly. Her muscles pulled the plastic up into her, filling her bottom with it. The narrowest portion was kept from being pulled in by a T-handle that was now lodged against her anus. This meant that her anus was also kept open. Trudy felt her stomach muscles ripple in the beginnings of an orgasm and her anus clamped down hard on the plastic plug. All it would take would be one tiny movement of the plug or Mr. Wilson’s finger on her clit and she would be over the edge but Mr. Wilson wouldn’t let her yet.
“Oh Please.” whimpered Trudy.
“Please what?” grinned Mr. Wilson.
“Please let me come.”
“When I’m ready. Now be a good little girl for me and don’t move until I tell you.”
“Yes Sir” whispered Trudy as she concentrated on not coming.
Mr. Wilson moved back and sat down, enjoying the sight of Trudy’s quivering body as she tried to keep herself from going over the edge. He was sure she’d never been more sexually stimulated in her life. He waited until she had calmed down somewhat before getting up again.
Trudy felt she was now more under control but the first touch of Mr. Wilson on the plastic plug in her bottom was as though it was an electric shock! She cried out at the feeling and arched her back again as he twisted it slowly inside of her. His fingers grasped the plug and moved it in and out in minute movements. Mr. Wilson started to pull the plug from her and Trudy thought she would faint. Her pussy gushed more of her juices and she knew that her thighs were soaked with them. She couldn’t stop moaning and whimpering as the object was slowly pulled from her and she felt her sphincter grasp at it despite herself. Trudy’s face was beet red both from excitement and the humiliation of so exposing herself to her lover. A moment later the plug was pulled all the way out leaving Trudy trembling.
“Trudy, do you want something now?” asked Mr. Wilson.
“Oh God do I ever!” said Trudy, “Please do it Jeff.”
Mr. Wilson smiled down at her upturned bottom. “And what would you like me to do?”
Trudy blushed “You know.”
“No I don’t.”
“F-f-f-fuck me.” she stammered embarrassed by even saying the word.
“And where would you like me to fuck you?” asked Mr. Wilson in a soft voice.
Trudy hesitated then replied in a tiny voice she barely recognized as her own. “In my bottom.”
Mr. Wilson moved forward until the head of his cock was just touching her anus. He was well lubricated already and Trudy’s bottom was, of course, completely slippery. Trudy held her breath, waiting for him to push forward. Mr. Wilson waited a long moment until she started to relax then pushed the head of his cock into her. Trudy gasped. He was in! She had never thought it would be so easy and so, so hot! Mr. Wilson held himself there for a moment but Trudy pushed backward, wanting all of him. A moment later he was buried in her to the hilt.
Trudy’s body was a riot of sensations, her pussy was still soaking wet and her clit was quivering. Her nipples had been hard since she arrived and now they were so hard they ached. The blindfold seemed to center her attention completely on what was being done to her.
Mr. Wilson started to move slowly in and out and Trudy started to rock with the rhythm. Trudy was getting closer and closer and Mr. Wilson knew he was too. Her bottom was very tight and so hot that he had to control himself from just spurting inside of her. Trudy heard Mr. Wilson’s breath getting shorter and she knew he’d come soon just like her. Their movements were quicker and deeper now. It was only a moment before they wouldn’t be able to hold back anymore. Suddenly Mr. Wilson paused, leaving only the head of his cock inside of her. Trudy moaned in frustration and tried vainly to push back on him.
“Trudy,” he gasped, “do you know what I’m going to do to you tomorrow?”
“MMmmmmm,” she moaned, “Anything, you can do anything to me.”
“I’m going to shave your pussy bald and I’m going to spank your bottom just like a little girl.” said Mr. Wilson
“Oh!” cried Trudy. The thought of doing that was too much and Trudy felt herself tumbling beyond any possibility of holding back. Her orgasm started to rush in on her from all sides and as it did, Mr. Wilson plunged back into her fully and deeply. Trudy cried out and felt her rectum squeeze her lover tight. That was all it took for Mr. Wilson and he felt his cum rush up from his balls and shoot deep into Trudy’s bowels as she thrust herself hard back onto him.
The orgasm seemed to go on forever cascading over them again and again until they slid, exhausted onto the sheets of the bed.
Lying there, in a warm afterglow, Trudy pulled off the blindfold and looked over at Mr. Wilson. “I meant it.” she murmured, “You can do anything to me.”
Mr. Wilson chuckled as he held the beautiful girl in his arms. “I meant it before.” he said, “Tomorrow, I’m going to have your pussy be smooth as a little girl’s and then I’m going to spank your bottom until it’s hot for me.”
“Mmmmmm” said Trudy, “That will be the hottest thing I’ve ever done.”
“It’s just the beginning.” said Mr. Wilson, “We’re going to be more outrageous and exciting than you ever imagined.”
“So long as it’s with you.” murmured Trudy as she snuggled.