u/petals87

Hey everyone, thank you so much for all the love on Part 1. I really didn’t expect so many of you to relate to that slow “I’m still straight… right?” phase. So many requests for Part 2, so here it is. This is where things stopped being just texting and I started actually changing.

We carried on that back-and-forth for a few more days. The sexting was getting rougher and dirtier, and I was fingering myself while reading his messages and staring at his dick pics. Literally just days earlier the thought of actually sleeping with a guy had grossed me out, and now here I was.

Then he started asking how I felt about chastity. I’d seen the hypno videos and other sissies posting their cage pics and honestly thought it all looked super weird and fringe. But there was something about wanting to please him that made me think “it’s not really my thing, but I’ll try it for him.” So I agreed to give chastity a go and to start a proper online dom/sub thing. Part of me was chasing that exact same electric rush I got the first time I slipped on my sister’s red “FLIRT” thong all those years ago. You girls know what I mean, that first-time high is addictive, and we keep going deeper chasing it again.

A couple of days later the chastity cage and some new toys arrived. I was so nervous when I told him. He told me to put it on straight away and send a picture. Well, I couldn’t get it on at first. I was way too hard. He suggested ice, and after some persistence (and a lot of deep breathing) I finally managed to lock it.

The second I heard that little click, oh my god. I stood there in front of the mirror just staring at myself, fully dressed in panties and a little top, locked up for the first time. The sudden weight of the cage pulling down on my clitty was so unexpected and intense. It made everything feel so real. That same rush from trying on my sister’s clothes hit me all over again. I thought it was going to feel weird and strange, but instead I felt so submissive, so controlled, so feminine. It was like the floodgates had opened and I was slipping faster and deeper down the rabbit hole than I ever expected.

The next few days he had me locked for longer periods, wearing a butt plug at the same time, and the sexting got even more intense. He told me he wanted me to become “permanently limp.” That honestly scared me at the time, I worried it might not be reversible if I changed my mind. But he was making me feel so good that I just went with it.

Before long I was in girls’ panties 24/7 and sleeping in girls’ pyjamas. Every night he’d tell me exactly which panties and outfit I had to wear the next day, and I had to send confirmation pics. Handing over that control felt so hot and weirdly liberating.

He started making me dry-hump my pillow while locked and film it for him. The chastity had this dulling effect. I could feel just enough friction and pressure to drive me absolutely crazy with frustration, but nowhere near enough to actually cum. It left me so desperate and horny that I’d hump the pillow even more eagerly, grinding harder and faster. He told me I had to do it like I was riding cowgirl on a guy, legs spread, back arched, imagining I was bouncing on a real cock. So that’s exactly what I did, moaning into the pillow while the cage kept me right on the edge with no release. God, it was humiliating, and addictive.

After about two weeks he told me he wanted me locked for a full week. I was nervous, but I was so deep in the sissy high by then that I just said yes. That first night sleeping caged and waking up straining desperately against it, fuck. Another switch flipped. I was suddenly so desperate to be fucked, but all I could do was grab my glass wand and play with my ass. It felt incredible.

That eventually led to us FaceTiming. I’d ride my dildo while he stroked his cock on camera. I started getting eager to finish work just so I could rush home, throw on something sexy, and get on call with him

Hey everyone, thank you so much for all the love on Part 1. I really didn’t expect so many of you to relate to that slow “I’m still straight… right?” phase. So many requests for Part 2, so here it is. This is where things stopped being just texting and I started actually changing.

We carried on that back-and-forth for a few more days. The sexting was getting rougher and dirtier, and I was fingering myself while reading his messages and staring at his dick pics. Literally just days earlier the thought of actually sleeping with a guy had grossed me out, and now here I was.

Then he started asking how I felt about chastity. I’d seen the hypno videos and other sissies posting their cage pics and honestly thought it all looked super weird and fringe. But there was something about wanting to please him that made me think “it’s not really my thing, but I’ll try it for him.” So I agreed to give chastity a go and to start a proper online dom/sub thing. Part of me was chasing that exact same electric rush I got the first time I slipped on my sister’s red “FLIRT” thong all those years ago. You girls know what I mean, that first-time high is addictive, and we keep going deeper chasing it again.

A couple of days later the chastity cage and some new toys arrived. I was so nervous when I told him. He told me to put it on straight away and send a picture. Well, I couldn’t get it on at first. I was way too hard. He suggested ice, and after some persistence (and a lot of deep breathing) I finally managed to lock it.

The second I heard that little click, oh my god. I stood there in front of the mirror just staring at myself, fully dressed in panties and a little top, locked up for the first time. The sudden weight of the cage pulling down on my clitty was so unexpected and intense. It made everything feel so real. That same rush from trying on my sister’s clothes hit me all over again. I thought it was going to feel weird and strange, but instead I felt so submissive, so controlled, so feminine. It was like the floodgates had opened and I was slipping faster and deeper down the rabbit hole than I ever expected.

The next few days he had me locked for longer periods, wearing a butt plug at the same time, and the sexting got even more intense. He told me he wanted me to become “permanently limp.” That honestly scared me at the time, I worried it might not be reversible if I changed my mind. But he was making me feel so good that I just went with it.

Before long I was in girls’ panties 24/7 and sleeping in girls’ pyjamas. Every night he’d tell me exactly which panties and outfit I had to wear the next day, and I had to send confirmation pics. Handing over that control felt so hot and weirdly liberating.

He started making me dry-hump my pillow while locked and film it for him. The chastity had this dulling effect. I could feel just enough friction and pressure to drive me absolutely crazy with frustration, but nowhere near enough to actually cum. It left me so desperate and horny that I’d hump the pillow even more eagerly, grinding harder and faster. He told me I had to do it like I was riding cowgirl on a guy, legs spread, back arched, imagining I was bouncing on a real cock. So that’s exactly what I did, moaning into the pillow while the cage kept me right on the edge with no release. God, it was humiliating, and addictive.

After about two weeks he told me he wanted me locked for a full week. I was nervous, but I was so deep in the sissy high by then that I just said yes. That first night sleeping caged and waking up straining desperately against it, fuck. Another switch flipped. I was suddenly so desperate to be fucked, but all I could do was grab my glass wand and play with my ass. It felt incredible.

That eventually led to us FaceTiming. I’d ride my dildo while he stroked his cock on camera. I started getting eager to finish work just so I could rush home, throw on something sexy, and get on call with him

I used to be a completely straight guy — dated girls, watched “normal” porn, zero interest in anything gay. But I guess it all started one innocent moment in my teens that I guess set me on this path. This is how I went from regular dude to secretly dressing up, craving cock, and sliding deep down the rabbit hole. Part 1 covers the beginning and the first big cracks in my “straight” identity. Part 2 (the real descent with toys, meets, chastity, etc.) coming if you guys want it.

I was early teens when it first hit me. I was chilling downstairs watching TV when Sophie Elise Baxter came on performing her new song. She was in this tight pink pencil skirt, swaying her hips subtly to the music. The way the fabric hugged her curves… out of nowhere, a thought popped into my head: What would it feel like to wear a skirt like that?

My face went hot. Heart racing. My sister had moved out but left boxes of old clothes behind. I ran upstairs, closed her door, and started digging through the drawers like I was looking for treasure. That’s when I found it, a bright red thong with “FLIRT” written across the front in shiny silver glitter.

I still remember the exact second I pulled my boy underwear down and slid that thong up my legs. The fabric was so soft, so tight in all the right places. I was instantly rock hard. It felt dirty, exciting, and perfect. Over the next few days I kept sneaking back whenever the house was empty. A black mini skirt. One of her bras stuffed with socks. Soon I was standing in front of her mirror fully dressed as a girl, touching myself through the clothes, shaking with the most intense orgasms I’d ever had. I felt so pretty, so slutty, so right.

A few years later I left home and forced myself to stop. Packed it all away. Told myself it was just a weird phase. I went back to dating girls, trying to be normal.

But in my early 20s it all came flooding back. I was still dating and sleeping with girls, still identified as straight, but the only porn that truly got me off was trans porn. At first I imagined myself as the guy fucking the hot trans girl. Then that scary little thought started creeping in: What if I was her? I’d slam the door on it immediately “That’s gay, stop.” But it kept returning. Over time I started imagining myself as the trans girl in the videos… but only with other girls or other trans girls. Guys were still completely off-limits and grossed me out.

The crossdressing returned stronger than ever. I bought my own panties, stockings, a cheap wig, and little skirts. When I had a girlfriend I’d secretly wear her lingerie while she was out.

Eventually I wanted connection. I made a throwaway account and started posting on Reddit and CD dating sites. My DMs exploded — almost all guys telling me how pretty I was, how they wanted to fuck me, how I was hotter than their wives or girlfriends. I always replied “I’m only into girls,” but secretly? The constant validation made me feel so feminine and desired. It was addictive.

Then one guy stood out. He wasn’t pushy or gross. He was patient, flirty in a sweet way, and actually made me feel special. I kept chatting with him. At first it was innocent. Then, half as a joke, I started flirting back. Before long I was sending pics. First cute ones in panties… then riskier ones.

I remember the first time I got on all fours in my room, ass up, arching my back, taking photo after photo trying to find the perfect angle for him. My hands were shaking and I kept thinking “WTF am I doing? I can’t believe I’m posing like a girl for this guy and actually sending him these pics…” But it was so intoxicating I couldn’t stop. I hit send anyway.

Then came the worst (best) part……waiting eagerly for his reply. Refreshing the chat every few seconds, heart pounding, desperately hoping he’d approve, tell me how pretty I looked, how much he wanted me. Like seriously wtf am I doing I’m now craving this guys approval. When his messages came through, it was a pic of his massive hard cock….and I have this mixed feeling of joy and excitement that I made that happen, like omg I’m making this guy hard, I felt proud and conflicted but the rush was super powerful and I was just staring at his cock in awe and happy and probably because of all those things and the fact I was super turned on….i genuinely wanted his cock, I wanted to do more, I wanted to make him cum. I told him as much and sent him more pics, trying to be even more slutty and sexy, I felt so feminine to being kinda serving him, it was honestly intoxicating, he’d be calling me a good girl, saying I was sexier than his ex, I’d throb so hard it was embarrassing. It escalated fast — full-on sexting, me describing what I wanted him to do to me, him calling me his sissy. The fantasies got rougher and rougher.

I was still telling myself “I’m straight, this is just fantasy”… but that crack was getting wider every day. The attention, the filthy words, the thrill of being wanted as a girl — it was too intoxicating to stop.