Grayson to Gracey Ch. 01

Hello all!~ This is a mostly accurate story of how I started my sissy journey. Any and all feedback would be appreciated. Thank you for taking the time to read my story!~

The day started off like any other for Grayson as he relaxed after a day of college classes in his dorm. The door to his bedroom firmly shut as he laid back in his bed, scrolling on his phone looking to roleplay with. His eyes scanned over low effort post after low effort post but eventually stopped. The name "BBWsweetie19" popped out at him and he clicked on her post. It was very well put together so Grayson opened his messaging app and sent her a quick introduction.

A little white later, his phone buzzed with her very cordial reply. The two of them started chatting about ideas they had before happily settling on one and starting their roleplay. Grayson found that he had a lot in common with Erika as he learned her name. It wasn't long till they were sharing nudes with each other. Grayson loved the sight of her large, ebony breasts and wet pussy while Erika enjoyed pictures of Grayson's hard cock. Both of them were happy to see that the other was enjoying their body.

After a few weeks of role playing together, Erika suggested they introduce anal into the RP. However, Grayson wasn't a fan of anal. They agreed on a pool sex scene instead, but the seeds had been planted in Grayson's mind. That anal wasn't as bad as he thought. Those seeds would change Grayson's life forever, even though he didn't know it at the time.

Weeks turned to months which turned into years of Grayson engaging in erotic role play. With each passing month her boundaries loosened and tastes changed. He started off playing as strong men with visible muscles. By Grayson's last semester at college, he almost exclusively played as large breasted hermaphrodites with equally large cocks. Shifting from playing the dominant partner to more of a switch.

That was when someone messaged him on his now more femme profile. This gentleman was kind with his words, and said he had found Grayson's post (though it was posted under the name Gracey). He said he was interested in doing some hypnosis, which Grayson had listed as a kink on his post. He had meant it as part of a role play, but didn't see any harm in trying it out. Afterall, hypnosis wasn't real... Right? An hour later, this stranger on the internet had Grayson tranced. It wasn't anything extreme, just your standard introduction to hypnosis. Once again, the seeds had been planted though. Grayson now craved being a hypnosub.

He started searching the internet for more and more hypnosis videos and partners. None of them were able to recreate the experience of his first trance though. That was when he ended up on Reddit and found "SissyHypno" with all of its swirls. He sorted by all time top post and was treated to a gif of rapidly changing panties getting slid up a sissy ass while pink swirls played in the background. He found his eyes locked on that gif for minutes on end. When he finally managed to pull his eyes off of it, he was curious if panties really felt that good on smooth skin. At first he tried to disregard it, but ended up searching for more and more sissy hypno. By the end of the week, Grayson had ordered his first pair of soft, pink panties.

When they arrived at his dorm in its perfectly safe Amazon packaging, he grabbed his razor and shaved everything around his crotch. His hands glided over his now smooth skin and shivered. It was like nothing he had ever felt before. Grabbing his new panties, he pulled them up his legs till he felt the fabric on his now smooth, hairless ass. Biting his lower lip, his mind flashed back to the first sissy hypno gif he had seen. Grayson pulled those panties up his ass exactly as he had seen in that short gif. He let them snap against his ass when he finally pulled them all the way up. It was this moment that Grayson knew he was a sissy.

He went back on the internet and ordered even more panties of different colors. His cart even had lube and several different kinds of buttplugs in it. When they arrived, he had found someone to help him push his boundaries. She helped him push his first plug in when he thought he couldn't do it. She ordered him to wear panties under his boxers when he would go out for lunch. Eventually, ordering him to wear one of his vibrating silicone plugs on a walk. Grayson had to wear both a pair of normal panties as well as a tight thong in order for it to stay inside him as he walked.

It was an eye opening experience and he craved more and more. He was drawn back to Reddit, though this time not to watch more sissy hypno, but instead making a post on "Sissy Personals" and hoping someone would answer it. Grayson was not disappointed. Someone from his college offered to come over, even bringing some sexy lingerie for him to wear. Gracey was officially born.

When he heard the solid knocks on his door, Grayson swallowed and sent a message to her first lay, asking if it was him at the door. Wanting to make a good first impression, Grayson had already dressed up in his Sissy Gracey persona. She opened the door, standing behind it and let the stranger into the dorm room before closing the door. What happened next made Gracey's heart flutter.

"You look stunning," he said before holding out a bag with his gift in it. Gracey smiled as she took the bag and took his hand, leading him back toward her bedroom. She had to admit that he looked very handsome. They took a quick shower together before Gracey changed into her gift and laid on her bed.

His hands explored her soft, hairless body. The lingerie he bought for her softly clinging to her skin. Gracey got in position and took his cock into her mouth, sucking her first cock until it was nice and hard. It was unbelievable how amazing it felt to be a cocksucker. She spun around, presenting her sissy hole to her guest. He smiled as he slowly and carefully pushed the tip of his cock against her ass before grabbing a bottle of lube and squirting some out.

"Ready?" he asked in a soft, caring voice.

"Yes, Sir~" Gracey replied, taking a deep breath as he pushed forward, entering her sissy hole. It was quite like nothing Gracey had ever felt before as she experienced a new kind of fullness she didn't know she needed. He fucked the newly minted sissy until she couldn't take it anymore. Gracey was just too new and inexperienced. Instead she stroked him off over her and he came all over her stomach. He then returned the favor by sucking on Gracey's clitty until she came well, their cum mixing together on her stomach. She smiled as he got up, dressed, and left her dorm room, leaving behind a very happy sissy. A sissy with lots of adventures ahead of her.