Tim's Journey Ch. 05

The next day, Connie could not concentrate at work. She could think of nothing else but what she had planned for tonight. She was so proud of herself. She had total control over Tim. The power was such a rush, and she loved the way it made her tingle inside, and how wet it always made her. She still was a little amazed how willing he was to please her, and how far he had gone is such a short time to prove it. None of her subs in the past had gone so far, so fast, and so willingly. There was always hesitation on their part with some of the things she wanted to do. This always led to ultimatums by her and their eventual exit from her life. However, this one was different. His whole goal in life seemed to be only to please her, and this made her very happy. She knew she was going to go farther with this one than she had ever gone with any of the others.

As she sat at her desk day dreaming of all the possibilities, she could feel herself getting wet and her nipples getting hard, they were straining against her bra. She loved this feeling, and she reached up and gently ran her palms over her breasts, teasing her nubs. They continued to get harder and protruded through her tight fitting top. She grabbed each one with her thumb and forefinger and aggressively pinched them, sending a wonderful chill through her body and straight to her pussy. Her juices flowed more rapidly and she again pinched them. She squeezed them together and continued tormenting her nipples. She needed some satisfaction. She needed that power high as well, so she called for Sarah to come to her office.

Sarah entered and Connie told her to close the door. Connie sat back in her chair and contemplated just how to use her power over Sarah. Then she got an idea.

"Open your blouse." She ordered.

Sarah unbuttoned her top to reveal her large breasts in her sexy red lace bra. Then she just looked at Connie and waited for more instruction.

"Play with your tits."

Sarah started caressing her mounds just like Connie had been doing a few minutes before, squeezing them and pinching her nipples, making them hard. Connie felt the rush of power sweep over her as this young submissive girl did as she wished. The dampness in Connie's crotch grew, and she reached under her skirt to rub her pussy through her panties.

"Is that making you wet?" she asked the young girl.

"Yes ma'am." She replied.

"Do you want to play with your pussy?" Connie inquired.

"Yes ma'am may I?" she asked as she continued to maul her own tits, squeezing and pinching the whole time.

"No, take your tits out of your bra." She ordered.

Sarah obeyed.

"Bite your nipples!" she commanded.

Sarah lifted her big tits to her mouth and started biting her rock hard nipples, alternating each one to her mouth over and over again. Each time she felt her teeth touch her sensitive nubs; the pleasure grew more between her legs. Her panties were getting moist as her juices flowed from her hot pussy. She always loves being told what to do and the more Connie ordered her to play with herself, the hotter she got.

"That's it; play with those nice big tits of yours. Get your pussy all wet. Mistress has plans for you." Connie continued to taunt Sarah.

Connie was enjoying the show and the feeling of dominance. She pressed harder on her panties, finding her clit and fingering it. The rush of pleasure coursed through her body and she continued her orders.

"Pull up your skirt, take off your panties and put them on my desk."

Sarah obeyed.

"Go to my toy box and get a big fat dildo."

Sarah went to Connie's bathroom and in the closet in the back was a large drawer where she kept many sex toys for occasions like this. She looked in and pulled out a large fat rubber dildo and returned to the office. Sarah was so turned on by the sight of the large fake cock and the commands that were being fired at her she could feel her juices oozing out onto her thigh.

"Suck that monster!" Connie hissed at her.

Sarah did exactly that. Standing there with her tits hanging out of her bra, her skirt up around her waist in stockings and high heels, she was a sight for Connie to behold. Sarah devoured the fake cock like it was attached to a man. She slid it in and out of her mouth making it slick with her spit. She wanted it in her sloppy pussy and she sucked it like a whore in heat.

"Ok, fuck that dripping cunt of yours with that cock. I want to watch you cum."

Sarah took the dildo and shoved it into her wet hole and started pounding herself with it. Connie sat there and watched the show as she continued to rub her clit harder and faster. They both muffled there cries of passion as they both reached orgasm within a few moments of each other.

After it was all over, Sarah reached for her panties. Connie told her to put them on, but not to clean up and to go back to work. Connie felt her soaked panties, and was pleased with herself when she felt how wet they were. She was going to leave them on the rest of the day and not clean up either. She had plans for Tim and those panties later.

When they arrived home, Connie and Sarah walked in the door and found Tim in his usual position. Sarah was walking by Tim when Connie told her to stop and stand in front of him. Sarah retreated and did as she was told. She stood in front of him so the front of her skirt was almost touching his nose.

"Lift up your skirt." She commanded.

Sarah grabbed the hem of her skirt and hiked it up so that her panties were exposed. Tim could smell her pungent fragrance from her earlier experience with Connie. His cock started to fill with blood and grow as he sniffed in her essence.

Connie just stood there and watched as Tim's little cock grew and he continued to breathe in deeply. She wanted to get him good and hot for her little adventure a bit later. After she was satisfied that he was good and aroused. She ordered Sarah to take off her panties, turn them inside out and stuff them in Tim's mouth. Sarah did exactly that. She relished the feeling she got from the little bit of power it gave her.

Her panties were warm and Tim could taste the cum left on them from earlier. They tasted great. He moved his tongue all around the panties that filled his mouth. His cock twitched and he was getting hotter by the second. Then Connie did as Sarah had done and moved her crotch up to Tim's nose and ordered him to bury his nose in her panties and breathe in her scent. This worked to further turn him on. Both women's fragrances flooded his senses and he became even more turned on.

Then Connie backed up and took her panties off. Tim gazed longingly at her shaved pussy. The lips were swollen from her arousal and her clit stuck out from its hood. Then Connie took her panties and placed them over Tim's head so that the crotch was in front of his nose. He could see through the leg holes of them and could see how happy Connie was with herself. Then he turned and saw Sarah watching with a smile on her face as she slowly stroked her clit. The humiliation only added to his arousal.

Then Connie ordered him to her room, "Go kneel on my floor by the foot of the bed and wait for me."

Tim stood and quickly rushed upstairs. Sarah finished the dinner Tim had started and they both ate as Tim stayed upstairs and awaited their arrival.

A while later Connie arrived in her room. Tim knelt obediently near the foot of the bed. His cock stood at attention. His mouth had long ago soaked Sarah's panties and they had lost their taste. However, Tim continued to breathe in deeply to get more helpings of the glorious smell that Connie's panties provided.

Connie passed by him and smiled wickedly at her creation. She decided to tease him a bit more before she really got to the business at hand. She stood right in front of him and began to unbutton her blouse. With each button, Tim's eyes got wider as he anticipated seeing her lusciously huge tits. She removed her blouse and massaged her tits a bit in her bra just to torment him a bit. Then she turned around and removed her skirt, making sure to bend all the way over so she was sticking her large round ass in his face, before she stepped out of it. She still had her stockings and high heels on and decided that would be good attire for this evening. She then went to her trunk of sexual goodies and pulled out a long thin strap-on dildo. She didn't want to get the thicker one she had, for fear she might hurt Tim's virgin ass. She stepped into it, pulled it up and buckled it in place.

Tim just stared at her the whole time she was preparing herself. When she retrieved the dildo and he started to get a bit nervous. He did not know what to expect. He did trust Connie, but he had never experienced what was to come.

Just then Connie called for Sarah to come into the room. She entered the room and Connie told her to strip. She did, and as she did, Tim just watched. He was again getting very hot. Precum was dripping from his cock, and he loved the show.

Sarah had seen the strap-on and knew she was going to get a good fucking from her mistress. She was still moist from earlier in the day and as she started imagining what was coming, she got more aroused.

Connie ordered Tim to move to the side of the bed so he would have a good view. Then Connie bent Sarah over the foot of the bed as Mark had done to her last night. She started fondling Sarah's sex, getting it good and wet for her. Then she stood behind her and mounted her like a dog, and started fucking her hard and fast. She grabbed Sarah's hips and fucked her as Sarah moaned and screamed with excitement. Tim just gazed at the show, growing more and more excited with every passing moment.

Sarah's tits swayed back and forth with every thrust. Tim wanted to attack them. Connie made his day when she ordered him to take the panties off his head and out of his mouth, and lie on the bed and suck Sarah's tits while she fucked her. He scurried to the bed and lay under Sarah. She bent over a bit more to ease his access to her mounds. He grabbed them both and attacked them. Nibbling and sucking each one into his mouth alternately, he was in heaven. Sarah felt the coming of her orgasm like a bubbling volcano building to eruption. Connie's Dildo had a part that inserted into her own cunt and little fingers that rubbed her clit as she used it. She was getting almost as much pleasure as Sarah.

As Sarah let out a scream announcing her orgasm, Connie felt her climax coming too. She just pounded on Sarah's pussy harder and faster until she felt her orgasm hit and she moaned out with pleasure.

Tim was busy with his favorite activity in the world, playing with big tits. He heard all the moaning and screaming from the women and he thought he was going to cum himself. He stopped playing with the tits dandling in his face and warded off his orgasm.

Connie stood there after her orgasm and could see how turned on Tim was. His cock twitched impulsively, and his balls were high and tight in his little sack. She called to him and asked a question, "Would you like to tastes Sarah's pussy?"

"Oh yes ma'am." He answered excitedly.

"Go kneel next to the bed and I will let you tastes her pussy."

Tim hurried to the floor and anticipated Sarah putting her pussy in his face for him to lick. However, he was a bit surprised when Connie walked up to him and placed the dildo strapped to her in front of his face. He could smell their juices, and it triggered that lust in him almost instinctively. The fake cock danced in front of his face, dripping with Sarah's cum.

"Suck momma's cock and you can taste Sarah's pussy." Connie said seductively.

Tim didn't even think twice. He opened his mouth and eagerly started cleaning Sarah's cum off the rubber cock. Connie was so proud of herself. The power was almost intoxicating. Watching this man suck her fake cock and knowing she was soon going to fuck him in the ass with it.

"That's it Sweetie, clean momma's cock and get it all wet with your spit so I can fuck you with it." She said with a devilish grin.

Then she grabbed his head and started fucking his face like all the guys had done to her in the past. Connie pulled the cock out of his mouth and sat on the edge of the bed. She told Tim to stand and bend over while he sucked her cock. He did as he was told. Then Connie looked at Sarah and spoke, "Ok my pet, get the lube and get his ass ready for me."

Sarah grabbed the tube of lubricant from the chest of goodies and placed a big glob on her middle finger and started rubbing it on Tim's puckered hole. The feeling was amazing. He had always wondered what it would feel like to have a woman play with his ass, but never got any of them to do it. He was enjoying her massaging the outside of his ass when suddenly she penetrated his sphincter with her finger. Tim jumped a bit, but Connie grabbed the back of his head and forced his mouth back down around her dick. Sarah continued to assault his hole with her finger.

Tim fought against it for a while, but then it started to really feel good. He could feel her finger tip against his prostate, and his cock got hard as a steel pipe.

Tim was sucking a fake cock and his ass was being penetrated with this woman's finger. He should have been humiliated, but in his state of arousal, he didn't seem to even notice how degrading this should feel. He just sucked and moved his hips in rhythm with her finger, enjoying every feeling they both brought.

When Connie was satisfied that his ass was ready for her, she ordered Sarah to switch places with her. Sarah went to the bed and laid back and opened her legs. "Eat me you pussy!" she snapped. She was really starting to enjoy the power of domination.

Tim dove right in. He sucked and licked and nibbled all the parts of Sarah's pussy as Connie looked on with delight. Then she grabbed her hard rubber cock and placed it at the entrance to his ass.

"Spread your ass for me." She commanded.

Without even slowing his pussy eating, he reached back with both hands and spread his ass cheeks for her. Connie grabbed hold of his hips and slowly drove the fake cock into his ass, not stopping until her pelvis touched his ass.

Tim tensed up a bit; he had never had anything that large up that hole before. It was a bit of a shock and he tried to relax to ease the pain that was accompanying the phallus. Then Connie retreated. He could feel every bump molded into the strap-on dick, and it triggered even more arousal. The pain was real, but it was a good pain he decided. As Connie slowly reached the top of her stroke and again pushed in, the pain started to subside and the lube was helping now that it was all over the length of the dildo. She got into a bit of a rhythm and Tim was starting to enjoy the feeling. In and out, in and out, she moved. Now she started moving a bit faster, and then faster. He started moving against her as her speed increased. He was really getting into it.

"You like my cock in your ass my pet?" Connie asked.

"Uh hmmm." He mumbled, not stopping the assault on Sarah's sloppy cunt.

Sarah was digging the pussy licking she was getting and she started to cum. "Oh Yes!" she screamed, as her orgasm hit. "I'm Cumming!"

Connie too was approaching orgasm as she soaked in the scene she had created. The dildo did its job on her now drenched pussy. She started fucking his ass fast and hard. In a few moments her body shuddered with excitement and she came, screaming as it ran through her body. As the feelings continued through her body, she leaned on his back. Her tits squeezed against his back and her body. He could feel the smooth cool silk of her bra and he loved it.

When she had recovered, she stood up and wanted to make sure Tim was willing to perform like this in the future. So she told Sarah to kneel next to Tim. Sarah moved beside him and Connie started again moving the rubber cock in and out of his ass. She told Sarah to start playing with his balls.

"Play with his little nuts" She commanded. "Make him cum for me. I like seeing his little penis shoot its wad."

Sarah reached under him and grabbed his sack lightly. His cock was so hard his sack was tight against his balls, and his balls were so high from his arousal that they didn't even dangle below his throbbing cock. She cupped his little nuts in her hand and started massaging them as Connie quickened the pace of the cock assaulting his ass.

Tim could not believe how much he was enjoying the feeling of this fake cock being driven in and out of his ass. The humiliation of having this woman treat him like a bitch and fuck him up the ass just drove his desires higher. He could feel his orgasm coming as Sarah continued to fondle his nuts, and Connie fucked him hard and fast.

It wasn't long before he was uttering a primal grunt as he shot cum all over the sheets. Shot after shot kept coming. He could not remember ever shooting this much cum in his life. Every deeper degradation Connie forced on him only brought him greater pleasure than the time before. After the last spurt of his seed had launched across the sheets, Tim collapsed on the bed, landing directly in the puddle he had just created. He lay there as Connie withdrew the fake cock from his ass and all he could do was turn over on his back and say, "Thank you ma'am that was incredible."

Connie glowed as she heard him voice his appreciation. She was so proud of herself and of him for being so willing to please her. She just looked at him and said,"You are welcome my pet. Anytime you want that again, you can just ask. I love fucking men in the ass with my cock."

Connie removed the strap-on and climbed on top of Tim as he lay on the bed. She straddled his face and told him to clean her pussy. She was actually dripping cum from her lips. Tim eagerly lapped up all the juices from her cunt, drinking all her cum down his throat. He couldn't have enjoyed anything more.

After she was clean, they all went to the shower and Tim was ordered to wash both the women. Then he had to remove the soiled sheets from the bed and make it for Connie to sleep in.

Everyone went to bed soon after that. Tim lay there more sexually satisfied than he had ever been in his entire life. The more Connie took control, the more he wanted to please her. The more degrading she got, the more pleasure he enjoyed. He decided that he had complete trust in Connie. She new what pleased him, and it seemed she knew him better than he knew himself. He was going to give himself completely to her. He didn't know he could be this happy and satisfied, but he was exactly that. He drifted off and slept a deep comfortable sleep that night.

Everything was normal for the next week or so, when Connie decided it was time to move to the next level. For Tim to become the complete cuckold she wanted him to be, he was going to have to develop a taste for cum, male cum. So she devised a plan to initiate that.

One night after dinner, they were all sitting around watching TV when Connie ordered Tim to come stand in front of her as she sat on the couch. He obeyed. Connie opened her robe and started playing with her tits.

Immediately Tim's little cock sprang up. Connie just continued to tease him with her enormous tits. She pinched her nipples and squished her mounds together. Tim just watched and said nothing.

When his cock was good and hard, Connie started talking to him.

"Would you like to suck momma's big tits? She teased.

"Yes ma'am." He replied

"Stroke your little pecker for me and I will let you suck my tits."

Tim grabbed his modest cock and rubbed his hand up and down its length.

Connie just continued massaging her breasts and talking to him. "Would you like to fuck my tits?"

Tim just nodded as he gazed at his favorite things in the whole world.

"I like watching you stroke your pathetic little penis." She chided