Not that bad

Chapter: Risky Intimacy (rough draft v1)

The tension from the meeting still clung to Josh as he made his way home, his mind a whirlwind of thoughts and emotions. The stern expressions, cold judgment, and the unsettling shift in his status weighed heavily on him. A brief glance at the clock reminded him that his first night shift loomed ahead, but sleep felt like an impossible feat.

**** for some normalcy and comfort, he picked up his phone and dialed Felicia's number. Her voice, filled with warmth and surprise, was a balm to his soul.

"Hey, Felicia, are you free this afternoon?" Josh asked, trying to sound casual. "I thought maybe we could hang out or go on a date?"

"Absolutely! That sounds wonderful," Felicia replied, her enthusiasm evident.

When they meet up Josh noticed that Felicia was looking worn down and gaunt, but on questioning dismissed it as a restless night and that she was determined to not let it ruin her day.

The impromptu date unfolded with a natural ease, overriding the chaos that had consumed Josh's day. Laughter, shared stories, and flirtatious glances brought them closer, and by the time the afternoon was drawing to a close, they found themselves back at Felicia's place.

The chemistry between them had been building, and now it felt like the dam was about to break. Josh's heart raced with anticipation and anxiety.

He was nervous, acutely aware of his changed appearance and the misconception he had yet to correct to Felicia. The recent changes had made him look even more like an attractive woman, a detail that added to his apprehension.

As they moved to Felicia's bedroom, the reality of the situation settled in. Josh found himself on Felicia's bed, adorned in a beautiful dress, his body a mix of anticipation and fear.

Josh lay there on Felicia's bed, the hem of his dress sitting at his thighs, a heavy thud of anticipation in his chest. As her fingers hovered over the fabric, a maze of thoughts scrambled through his mind.

'Is this how it feels to be on the precipice of a full reveal?' he pondered. 'A part of me wants to stop her, to either run away and hide to tell her everything later at some undetermined date where a rejection can't hurt. The other part... the part that's feeling the warmth of her touch, the sincere affection in her eyes, wants to dive into this unknown. Should I warn her about what she is about to find?'

'I don't know how to navigate this,' his thoughts spun. 'The judgments of colleagues, the societal expectations, office drama and even Hero protocol, those are obstacles I can conceptualize. But what does it mean for me to be intimate as... well, as whatever or whoever I am now?'

AISYS had reshaped his physicality, but it was the texture of his emotions that felt most altered. He remembered the days when physical touch was like a language he couldn't comprehend, he had always wanted a partner but could never wrap his head around what that actually meant, even when he was dating. Every kiss felt like a question, every touch like an accusation. Now, it was as if AISYS had given him a dictionary to a language he had never known, but was expected to speak fluently.

'If AISYS changes how my body feels pleasure, does that change who I am? Am I still Josh, or is the new form the truest reflection of me? How do I take ownership of my pleasure when the definitions of 'me' are so blurred?'

His thoughts halted when Felicia began to speak. "Be calm my little kitten, you look like your heart is about to burst. Is this your first time with a woman?" His heart pounded in his ears, drowning out his internal turbulence.

'I don't know what this makes me. But in this moment, **** and exposed, maybe I can find a piece of the answer.'

The moment of truth arrived when Felicia's hand reached for the hem of the dress and started to pull it up revealing Josh's manhood.

She paused, her eyes widening slightly, both partners freezing, but her expression softened. A smile spread across her face as she looked in his eyes.

"Don't worry, babe; this doesn't change my plan for the night at all," Felicia said with a gentle confidence. "You'll just not need the strap-on when it's your turn on top. But it's my turn right now, so I hope you're ready to be treated like a woman."

He was more than thrilled at her acceptance but not about the last part of her statement. While he felt more at home in his new body and had vague memories of being treated as a women in his dreams, he did not have the parts a women did for this activity.

Felicia had attached a strap on and was lubing it up during his internal stall out.

Felicia was getting lined up and when he snapped out of it ready to ask her to stop when AISYS piped up inside his head. 'Don't worry Josh, even without practice this will not hurt you, in fact as a women you should learn to enjoy it especially if your partner does. Would you like my help?'

Not wanting to ruin the one purely good thing in his life right now he says "Yes." but not sub-vocally.

Felicia thinking he was talking to her replies. "Does my cute little slut really want my cock? Don't worry dear, I'm more than ready to fuck your brains out."

With that she plunges in right as you feel AISYS move around your body.

The easy entry surprises Felicia " Wow you must actually be a slut to be this lose, how many people have you let fuck this cute ass of yours?"

"None." he gasps out, already feeling way better than he ever though possible from this, there is no pain thanks to AISYS, and he can feel her directing the strap-on to hit just right and every time it does she ignites the nerves in his cock and balls. He is rock hard and its not been touched.

"Are you sure babe, because your tacking me like a champ and it looks like your about to explode with out your cock getting any attention." She teases as she changes position to let her alternate kissing a nipples and teasing the other then trails kisses up to his ear while continuing to thrust and tease his nipples. She whispers "What ever the truth is it doesn't matter because your mine now." Then she twists his nipple a little harder and starts thrusting deeper and harder. " CUM now pet." she says while nibbling on his ear.

Between AISYS playing his body from the inside, and Felicia from the outside, its too much, He moans as he cums from anal for the first time, but his cock remains at attention.

"Wow babe that was so cute! As soon as you're hard you have got to return the favor." comes out of her mouth before she looks down as sees he is ready to go already,"Never mind"

She climbs on top and inserts him and starts riding. She seems like a very 'in control of the bed room' type and her movements haven't let his mind catch up but he can feel AISYS move around in his cock to make it fit and stimulate both of them exactly the right way. He Cums again and she starts to remark on it " Its ok babe, I'll just use a double sided strap-on next time we fuck, I'll fuck that cute ass until I'm more than satisfied. I would love to see how many times I can make you leak out your load with out touching your cock."

'She hasn't noticed I'm still rock hard, probably used to regular guys' He thinks, then flips her over, swapping positions.

"OH?!" she exclaims "Ready for more already?"

"I've had fun letting you lead but now it's time for you to be the one on bottom, slut." He says as he finds a good rhythm and starts to tease her and whisper in her ear like she did. 'AISYS can you send a light current through me to her at points of contact? I want to alight her nerves in pleasure at every slight contact.'

'Yes I can, would you like anything else?'

'Yes can you extent a little of your self to simulate the clit, by the time I'm done with her I want her covered inside and outside in my cum and a mental mess of pleasure.'

AISYS complies an and before long Felicia has her first O moment, but he keeps going, with little to no time to reset herself, her dirty talk has dissolved into a cry of "OH god!"

By the end on the evening she passes out in bliss covered in cum. He had done everything to her at that point.

RING* 'That's your alarm that its time to get ready for work' AISYS remind him. He cleans up the bed room but puts a dildo and plug in her to keep his cum from leaking out, steals a shower, and heads out.