The Journey

Story Info
Submissive sissy's journey to submission.
1.6k words
4.02
52.1k
9

Part 1 of the 2 part series

Updated 10/17/2022
Created 12/06/2011
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Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while they chatted online, and had even begun to suggest that he wear it for a few hours in the evenings. Tom was a lifelong transvestite. As a kid he appeared to the world as an athletic rough and tumble boy, but he secretly loved to dress very feminine and loved the feel of silk, satin and nylon. He was also very excited about bondage. He loved the helpless and restrictive feeling that bondage provided and it seemed to be a natural part of his feminine and submissive alter ego. While Tom was able to indulge his fantasies on rare occasions, he was like most any other guy in that he knew he was supposed to get married and have a family. He tried to push the feminine and bondage feelings aside. But even after a long marriage and kids the feelings were stronger than ever. His sex life had deteriorated badly in recent years. She wanted nothing to do with his "perversion" and had grown rather frigid towards him. He had tried so many times and in so many ways to re-interest her in sex, but all of his efforts were futile, and had met with failure and rejection bordering upon open scorn. That part of their life seemed to be past now, and that knowledge hurt him deeply still. That had pushed Tom to pursue online sites that concerned transvestites, and BD/SM. Tom loved these sites early on and would masturbate while imagining he was the damsel in distress or maid in bondage. Masturbation was all that he had to attempt to satisfy the sexual yearnings she no longer seemed to feel. He would tease dominant men by saying that he would be their feminine sissy slave while full well knowing he would never follow through with a meeting. But as the years went on, Tom's feelings about truly acting on his long held fantasies became stronger. These feelings that he had harbored for decades were finally going to be acted upon. Every time he and Jason chatted, Tom would feel more girly and seemed to fall more under Jason's spell. Of course it was Jason who so forcefully "suggested" that Tom wear his CB-6000 device on his trip. Tom found that complying with such a request had begun to feel more and more natural, that pleasing Jason in such seemingly small ways had become very important to him. The plan was for Tonya (that's the name Jason had given Tom when they first started chatting) to text when he arrived at Jason's house. Jason would leave the front door unlocked and Tom would use the front bedroom and bathroom to transform into Tonya. That way Jason would only ever see the sissy slave Tonya and not have to deal with the boring society-facing Tom. Jason had never expressed much interest in stodgy old Tom, focusing all his attention upon Tonya instead. Their first meeting would be an overnight stay. The fact that they had chatted and e-mailed each other for a couple of months made this a little less risky proposition. They determined their respective fetishistic passions were extraordinarily complementary. Jason thrived on the power and control of training and using a newbie sissy slave and Tonya ached to be feminized and used. Tom sent Jason the text he had arrived and slipped into the unlocked front door to begin the exciting task of becoming Tonya. Jason had thoughtfully provided fluffy pink towels for Tonya to use. Tonya loved that Jason was a masculine dominant man but also was considerate of Tonya's shy and girly feelings and encouraged her to embrace them. Tonya also loved the feeling of very smooth skin. She shaved all of her body hair and made sure her face was as smooth as possible too. She wanted to look her feminine best the first time she met Jason in person. She knew he expected her to look like the slutty and sexy sissy they had chatted so much about. She chose a tight fitting black dress to go over her black bra and panties. She also laced herself into a tight black boned corset to achieve the hour glass figure that made her look and feel so feminine. Finally it was time to emerge from the bathroom and meet her dominant man, the one who had captivated her thoughts so often lately. She slipped into the black 4" high heeled pumps and timidly walked into the living room where Jason was waiting. He glanced over to take her in and was very calm and cool in his appraisal. He told her to twirl around so he could see her fully. He ordered her to bend over and shake her ass for him. Tonya was extremely compliant and excited. Of course her clitty was still imprisoned in the CB-6000 so she could only feel it try to grow in its prison. And yet, that prison made her feel even more free to embrace her submissive femininity, so under this dominant mans' control, it was like her clit was held tightly within the grip of his power at all times. Finally Jason came over and began feeling Tonya all over. He caressed her corseted waist and settled on her sexy ass. She loved the feeling of being felt up. She knew this was where she belonged and she was ready to give herself to this controlling and masculine man. Jason sensed that she was already under his spell and smiled to himself. He ordered her to his knees and then proceeded to tie her hands behind her back. With each pass of the rope around her wrists, Tonya's breathing became faster and she could feel her heart beating rapidly in her chest. Jason then began pulling down his pants. Tonya could only whimper as she saw Jason's semi erect cock spring out. He told her to kiss the head of it. Tonya was quick and eager to comply. She asked permission to take it into her salivating mouth and Jason graciously agreed. His smile was no longer concealed. He knew what he wanted, and he was getting it. Here she was, dressed sexy, clitty caged, on her knees, hands bound behind her with a gorgeous cock in her hot mouth. All seemed right in the world as Tonya began to worship Jason's wonderful man-meat. She felt his hand move to the back of her head and she relished the feeling as she concentrated on the head of his swelling cock, the tip of her tongue coaxing precum from his oozing slit onto her tongue where should could savor the taste of his essence. She found she was unconsciously making a low humming purr in her throat, which brought a throaty growl and a firmer grip upon the back of her head. The entire world narrowed to just Jason and pleasing him with her mouth, all the stress than had been in poor old Toms' life was gone, it had nothing to do with her any more, for Jason she was Tonya now and serving him for his pleasure was all that mattered to Tonya.

Tanya continued licking and sucking making sure to include Jason's balls in her oral parade. The feeling of being dressed sexily while bound and having her clitty caged while worshiping Jason's cock was making Tonya moan like the slut she was. After a while she felt Jason's cock grow even harder in her mouth and the twitch that accompanies the beginning of a male orgasm let Tonya know that a creamy reward was about to be hers. Although she had never swallowed a man's cum before, it seemed like she had been ready for this moment for decades. So many of the stories, pictures, and videos that she had masturbated to had revolved around a sexy tv swallowing a man's cum load. As the first of the jizz entered her mouth she nearly passed out thinking to herself that she had truly found her place, kneeling while bound and dressed as a sexy slut with a mouthful of man seed sliding down her throat.

She was able to swallow it all without spilling a drop and that made her feel proud. She looked up at Jason with her heavily made up eyes as if to say "was that good, Master?" Jason looked down at his slutty bitch and gave her a wry smile as if to say "not bad, slut, for a first-timer."

Tonya dutifully cleaned Jason's cock to make sure she accounted for every drop of Jason's cum. Of course Jason knew that Tonya had deep-seeded submissive feelings. That's what made their relationship so perfect. He was a domineering sissy controller and she was a submissive sissy slut.

Jason told Tonya that she did ok but that she would need to continue practicing her cock sucking skills to become a better sissy for him and his friends. Jason already envisioned using his new prize for the amusement of others. He would always own her but part of ownership includes being able to whore his bitch out to others. Yes, that would come in time but several more sessions would be required to ensure that she was ready to please others to the degree that they would always be a little jealous of Jason for having such a completely feminized sissy slut available to do his bidding.

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5 Comments
AnonymousAnonymousabout 12 years ago

Sorry, but unless it is reformatted with more paragraph breaks, it is unreadable

AnonymousAnonymousabout 12 years ago
Imagination!!

Wow. Enjoyed it.

AnonymousAnonymousabout 12 years ago
Re: Paragraphs

Actually, she had it nicely formatted and a lot of the formatting got removed in the submission process (she is My sissy submissive)

AnonymousAnonymousabout 12 years ago
Paragraph

Try to use smaller paragraphs.

AnonymousAnonymousabout 12 years ago

Very well done for a first submission. Hope this story will be continued.

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