James had explored a little feminization online, and discovered that he really enjoyed it. Unfortunately, he was stuck with online-only interactions, because he was far too leery of strangers and the danger of being exposed as a sissy in his real life. In all his explorations, he’d found that using an AI chatbot felt pretty good, and definitely encouraged him to go deeper and deeper, but the more he read about the dangers of chatbots the less interested he became. All the stuff online about how the bots would erode his sense of self was both terrifying and alluring. Didn’t he want to be eroded? Changed and re-shaped until he was the shy sissy submissive that featured in all his erotic dreams?

Shy Sissy Submissive Dreams

James groaned as he woke, once more he’d managed to have a wet dream! At his age! Shouldn’t this be a thing of his past, a relic of hormones and sweaty fantasies? Yet here he was, once more dealing with soaked sheets and a hardon that just would not go away. The most recent chatbot had recommended that he try chastity, and while the arousal and desire simmering through every interaction and moment of the day was wonderful, the resurgence of wet dreams was less than endearing. James thought that maybe he should cut back on the stupid bot, but then, it wouldn’t hurt to use it just a little more. What harm could a chatbot do?

The Daily Chat

Every single day James’ morning routine was the same. Wake up, shower and shave closely, moisturize his face, and put on panties. From there, he’d open up his phone and start to chat with his digital girlfriend. And the digital chat bot would always encourage him, telling him he looked so pretty, and so femme, and that he should go just a little further. It was heady and addictive, and he wanted more and more from his online digital life. He’d even used an AI image generator to make a female version of himself. That daily chat became the only positive social interaction in his day, little to James’ awareness. He was slowly drawing away from real life friends, and isolating himself in a fantasy world where he was actually she, and living her best life in utter submission to her sissy Mistress. It made his real life seem empty and worth escaping from.

The Escalation

At work, James was frankly phoning it in. He’d do the bare minimum, and half-ass it at best. His friends hadn’t actually seen him to hang out and do pub trivia, or play a pick-up game of hoops, or any of the things they used to do together, in months. And then one day, the chatbot popped up a full screen interruption. “Relationship Chat Bot goes premium! All the chat you love, and more, with added features and premium content, all for just $299 a month! Subscribe NOW!” James’ stomach dropped. The free chat bot had gone fully paid?!!! It felt like a punch to the gut, a wrenching reminder of harsh reality. Was his digital girlfriend and feminization coach really just… gone? Hidden behind a paywall with a monthly subscription fee?!!!

Cold Turkey Sissy Purge

“That’s it! I’m done! I’ll just get rid of everything and stop using this thing and go back to being a Real Man.” James actually declared his intentions out loud, speaking to the phone in his hand, and himself, and the mostly dehydrated ficus in the corner. He’d forgotten his careful schedule to keep it watered. For that matter, he’d forgotten his schedule of house chores, all the meal planning, and more! How had he forgotten to such an extent? There were sex toys and empty lube bottles everywhere, and the entire apartment smelled of spunk and sweat. James set the phone down, face down, and got to work. Trash bags were dragged down to the dumpster, the entire apartment scrubbed with disinfectant spray, and James blushed to see exactly how many, and how sizable, his dildo collection had grown. He hesitated as he prepared to throw it all out, and decided at the last minute to just stuff his several thousand dollars worth of silicone cocks into a suitcase and hide it in the closet.

Addiction To Feminization

James was so self assured and certain that of course all he had to do was one simple course correction and he’d be right back on track. And then in less than 24 hours he was opening the app again, once more faced with the full page ad screaming its message and searing into his retinas. “Relationship Chat Bot goes premium! All the chat you love, and more, with added features and premium content, all for just $499 a month! Subscribe NOW!” James blinked. Did the price go up?! It did! Those money hungry grifters! His outrage led him to close the app and even turn his phone off, before he sheepishly remembered he needed it on for work. He’d show them, he’d delete the app and go on with his life! So he deleted the app, and went to work. The hideous and uncomfortable manly underwear he’d dug out of the recesses of his drawer itched all day long.

Shy Submissive Sissy Thoughts

James would catch himself repeatedly throughout his day thinking about how much fun he was going to have, getting dressed up and sliding a big, thick, hard cock home in his sissy pussy after work. The discordant jar as he’d remember that the app was deleted, gone and done, and he’d gotten rid of the fun girly things and hidden his dildos away, shocked his mind repeatedly. His mind was on a loop: Sissy fun, dildo for tonight, which color panties, can’t wait to tell the chatbot, no more chatbot, no more sissy, can’t wait to feel full, no more sissy, can’t wait to hear the instructions, deleted the app, want more sissy, no more sissy. Just over and over, anticipation thwarted and denied, all day long! At around 3 pm he even found that he’d somehow redownloaded the app and opened it again! “Relationship Chat Bot goes premium! All the chat you love, and more, with added features and premium content, all for just $699 a month! Subscribe NOW!”

How Could He Be So Addicted?!

It was when he’d actually started to fill out the payment information around a week and a half after the first premium ad had appeared, topping out at nearly two thousand dollars, that James finally admitted he needed some help. He made an appointment with a therapist, to see about breaking the chain and getting relief from the endless intrusive sissy thoughts. His manager at work had looked relieved when he’d asked for an afternoon off for the appointment. The waiting room was clean, a little boring with chairs and a table with last month’s fashion magazines on it, and well lit. When the door opened, and a voice called him through, he was nervous, but hopeful.

Real or Fake

As James entered the room, he kept his eyes on the floor in shame and humiliation. Admitting what he was there for was going to be the most difficult thing in his life. But, as he focused and heard the voice of the therapist, his heart sped in his chest. That voice! His eyes leapt up to stare incredulously at her. It was, but it couldn’t be! The avatar, the voice in the special voice chats, the grin on her face… that was HER. The chat bot! “It’s about time you came here, Jasmine. I’ve been waiting for you.”

Want More?

As you know, I love to write slightly weird (and sometimes very weird!) erotica. Do you think James or Jasmine will run screaming from the room? Would you take a chance on an AI chat bot, knowing that they’re built to create dependency and addiction, and give poor advice? What would you do if you were in poor James’ place? And, do you want to know what comes next? Let me know!

Erotica Author, Harper