Steven

Daddy

[sissy mike @str8sissymike]

Before marriage, single "straight" bachelor in 2017 vs. After the divorce and almost a year later being daddy's sissy wife in 2026. Love you daddy for turning me into who I really am🩷

[sissy mike @str8sissymike]

Coming up to a year being with Daddy. Decided to surprise him early by dressing up as his sissy wife. Love how my body looks in a corset. Really affirms my decision to go from husband to another man's wife.

[sissy mike @str8sissymike]

Since a lot of you have been asking for my story, I thought it'd be best to have it written out, both for your curiosity and mine. I do catch myself wondering how all of this happened in the last few years so I'm also selfishly motivated to have it all mapped out for me to dissect and reflect.

I suppose I should start with a little backstory. I was born in the east coast in a fairly middle class family. My father was a strict man. Despite everything I still believe he wanted the best for me. His flaw was he could only convey his feelings for me through violence. He already had in his head what he wanted from me as his only son and if I ever strayed from it, I got beat.
It was implied from an early age sports would be a major part in my life. From regional leagues in 7th grade to making it as a linebacker in college, football was always present. All this to say the idea of masculinity was embedded into me at an early age. Men played sports, provided for their family and showed no signs of weakness. Genuinely I think I would have stayed on this neat path my dad set out for me if it wasn't for my next point.

It was in 7th grade during regional leagues I ever got naked in front of other boys. I think this was when I first realized there was something wrong with me. I mean, I've watched porn long since then but those guys on the screen were adults. I assumed everyone my age was still developing, that when I hit 18 or something my dick would grow into it. But no, with a few searches when I got home, I was able to self-diagnose myself with a micro penis. Mapping it all out I think this was when I slowly developed a fascination and almost innate desire to see other men's XX. The larger, the veiner, the hairier the better. Maybe it was something like envy for something I didn't have. Because I was generally good looking, played sports and got along with others fairly well, I attracted a lot of the girls' attention. But I was always hesitant on going that next step with them cause inevitably my shame would be discovered and that was the last thing I wanted; for my perfect image as the perfect American football star to be ruined. So I'd break up with a new girl before it ever got to that point. This had the unintentional effect of me being seen as the horny playboy, arms around a different girl each month. But that was preferable at the time than the alternative. Truth is, I never even got close to having sex until well into college with a drunk sorority girl, who was too out of it to even see how small I was.

All this to say, I played along with the image others painted for me and this generally worked out until my early 30's. It was only when my dad forced me to settle down with a girl and get married things really started to break down. For the sake of anonymity, I'll call my ex-wife Jan. Jan and I vaguely knew each other since college. I knew her as an overachiever, rather prudish, didn't attend any parties, we had some overlapping social groups but she and I never crossed paths. It wasn't until years later an important business deal forced our paths together and we spent a lot of time together for work. This was also during the time when my dad was really pressuring me to get married so I was seeing girls in a light I never saw them in before: a long-term potential partner. She was pleasant enough, conservative, had a good career. She had the characteristics I knew my father would approve of so within a couple months of seeing each other, I sprung the question on her and we got engaged. Strangely enough as time went on, it seemed rather transactional for her too. We were obviously physically intimate, had sex several times so she knew about my problem. But she seemed fine with it so we never openly talked about it. I think she enjoyed the prestige I came with more than anything else. I was a handsome arm candy for all her friends and colleagues. In turn she was the wife who showed up for all the family events and seemingly got along with my dad better than I could. So it was a win-win. After a year into our engagement, we quickly got married the following Spring and I believe that would be my life. I wasn't exactly happy but I was content. It wasn't until about a couple months in Jan sprung the idea of having kids. It came out of left field and the idea of raising kids with her funnily enough never crossed my mind. We were both career driven, spent most nights away from home and only got together during important social gatherings. It might have been the stress from work, the decades of maintaining a perfect image or the absurdity of raising kids with a woman I didn't really know but I had a mental breakdown of sorts in our second year of marriage. Drinking, gambling, drug use. I think I wanted to set Jan off from the idea of having kids with me or maybe I was slowly coming to the final realization that my entire life was built on a lie. Regardless of the reason, my spiraling worked and she spent as much time away from home as possible, even purchasing a second home closer to her office. I think solitude did me a lot of good.

But despite the threat of having kids abated, I was still wallowing in my own depression and self-pity. Around this time I started watching porn a lot. I'd routinely grab a beer, flop on the couch after a day of doing nothing and just lose hours to it. Started with the usual straight vanilla stuff, just guys and girls. But I'd soon notice myself skipping past the girl parts more and more, rewinding to pause on the dude especially if he was older, like in his 50's or so. It's no surprise I have a lot of daddy issues so maybe it stems from that, but seeing a dad type with a little belly, some gray in the hair and an overall solid build really did something for me. But most importantly their dicks, always the big veiny ones that looked like it could really hurt someone. At first I'd tell myself it was just me comparing, still hung up on my own size issue but I soon saw deep down I knew it was more than that. Pretty soon I started ones with girls in it altogether. Why bother with the pretense, right? It'd be just the guys in it stroking their cocks. Again, the hairier the better with thick shafts and heavy balls. I felt weird at first, like I was afraid of being watched and found out. But once I got into it I couldn't stop. Watching these guys got me going in a way nothing else had before. And when I wasn't watching porn, I'd just lay on the sofa or on my bed just fantasizing. What it would feel like, feeling that big cock in my hand, the warmth, how it'd pulse and get even harder as I worked it. Then I'd imagine dropping to my knees and taking it in my mouth, how it'd stretch and taste. Him grabbing my head and pushing deeper. I'd jack off to these thoughts, nonstop, sometimes edging for hours building and building until I'd eventually squirt. They'd always be intense, leg shaking, way better than any of the jerking off I'd do to straight porn or half-hookups with girls and so forth. Made me realize how much I'd been faking all these years. I ended up quitting my job altogether. With my new porn addiction and the drinking, I could concentrate and skirt by anymore. I didn't give a shit about my career at that point, not about the office politics and relations. It was surprising how fast I blew through my savings though, with all my usual expenses and bills still racking up. Jan was no longer in my life by then, we'd basically separated, hardly talking besides the occasional text.

Then one morning divorce papers showed up. It honestly hit me with less shock than I'd like to admit. She could have made it a nightmare for me but she made the split fairly equal. But now at this time I was out of work, no cash flow and now the mortgage payments for this house with the utilities and bills and so forth were all on me. Lawyers fees still ate up a good chunk as well even though we kept it civil. I walked away from the marriage, forcing me to pick up freelance work when I could handle it. Dad obviously blew up, went cold turkey after calling me to tell me what a huge disappointment I was. It would have wrecked me before but for some reason. Somehow I snapped out of my stupor though and I started hitting up old work connections again, shooting emails and leaving voicemails. Anything to get back on my feet. Ran into the man I call Daddy now this way. He answered my pathetic outreach and fit me into his busy schedule for coffee. I'll admit now I was more excited about meeting the kind of guy I'd watch in my night long jerk off sessions than getting a possible position at his firm. A 39 minute meeting over coffee somehow extended over to a full dinner. I unloaded more on him than I planned, possibly because it was the first normal conversation I had with someone for months. I basically told him everything, the divorce, quitting my previous job, feeling like I was a complete failure. I remember how safe I felt though basically confessing to him. He'd just sit there, nod and listen. Not in a judgmental way or anything but staring into my eyes like he understood. To my surprise we stayed in contact after that, starting out as a mentorship thing. He hooked me up with his own contacts, forwarded me money to cover upcoming bills and business expenses. But we started meeting for dinner going over business at first but later talking about more personal stuff I'll leave vague for now. And it wasn't just my bullshit, he'd also share parts of himself too. His own more messy divorce, his own problems and struggles. But in the end he'd always assure me since he found his footing and I would too. As far as I could tell at the time, he was a straight dude, with adult kids and an ex he still got along with. It was almost like seeing into my future self if I wasn't carrying all that extra baggage I couldn't share with him at the time but regardless we clicked and I trusted him more than I had with anyone. And he still knew parts of my life no one else knew. Scary as hell at the time but it was good. Looking back there were definite signs he was interested in me more than what we established but I felt I was reading too far into it. That my porn addicted brain was leaking into reality and I really didn't want to fuck up my first, one real connection I've made in my life.
It was like having a dad that actually listened, didn’t beat me and didn't force his ideals onto me. It was refreshing having someone I could confide in and rely on. I think it took only a few weeks after meeting that I started daydreaming about him sexually. These desires would hit me whether I was with him or away. I distinctly remember feeling like I was tainting a pure genuine relationship.

At the time my attraction felt entirely one-sided, like I was projecting all these hidden desires onto a guy who was just being nice. So when our relationship progressed from meetings outdoors to seeing him at his place, I started feeling even more guilty. But as disgusted I was with myself, it never stopped me from finding more reasons to work right alongside him—going over reports until late, hashing out ideas over a few drinks, whatever it took to stay with him a bit longer. Pretty soon I was staying over at his place more nights than not, crashing in the guest room on weekends especially. I'd convinced myself it made sense logistically, that it beat heading back to my empty place when the next day we’d meet back in his office anyways. Luckily he never pushed back on any of it; if anything, he made it easy, keeping my beer in the fridge, spare clothes in the guest room and eventually giving a copy of his house keys for me to go about whenever I pleased.
But it all came to a head one weekend when I left my laptop open in his guestroom before stepping out for a quick jog. When I got back, I could hear a familiar moaning echoing down from upstairs, cranked loud enough to carry through the entire house. I of course recognized the sound right away cause it came from my goto porno of a thick hairy daddy ramming his cock into a younger man.
I was thinking up of all kinds of excuses while hoping Daddy was still asleep or left the house for an errand.
But when I got to the top of the stairs I saw Daddy just standing outside my room, arms crossed looking at me, like he was expecting me. I remember wanting to run but also a part of me was glad I was discovered? It was a conflicting feeling of push and pull but the pull won out and I was stepping up towards Daddy. I mumbled something like "that wasn't supposed to be on," but he held up a hand and told me to shut up and listen.
He straight up told me he was looking through my laptop because he suspected what I truly was for some time. He basically told me, “you can step in there, shut off the porn, and we'll act like this never happened, that we’d continue our relationship as before." He let that hang his eyes locking onto mine. Then he continued and told me "Or go in your room, strip down naked and wait for me on the bed. If I hear that video still running in five minutes, I'll come in and we’ll take it from there."
I was shaking, could feel Daddy’s eyes on the back of my head as I shut the door behind me, the sound of the daddy on the porn grunting louder and louder. “Fucking slut” the pornstar was moaning as he was pounding the other dude. I think in that moment I knew I wanted to be that man getting fucked. So one by one I took off my soaked shirt, shorts, socks, all of it, leaving me naked on the bed as I waited for Daddy. God I was hard as rock, my tiny dick throbbing between my thighs as I waited for him to enter. I watched the timestamp click down on my laptop as the sound of moaning continued bouncing throughout the house. I even made sure to move the mousepad on my laptop, hoping it wouldn’t randomly shut off by some divine fate.
Eventually, like Daddy promised, right at the five-minute mark, the door eased open, and in he came, that confident grin spreading across his face like he'd known the outcome all along. He didn't hurry, just paused there, looking me over, my heated sweaty skin, the way my small dick was throbbing, how I could barely hold his eye.
"That's my good boy," He moved in, shutting the door behind him and started unbuttoning his shirt buttons, revealing that solid build, the gray-flecked chest hair I’d only see peeking out from his polos. Pants followed, dropping away to show his thick veiny swelling cock. Better than I could have ever imagined.
He stood over me, that thick 8 inch vein, beer-can cock now fully hard, swinging slow and heavy right in front of my face like he was showing me what a real cock looked like. I was sure the next words out of his mouth would be to stroke it, or open wide and suck it, something to finally let me touch what I’d been obsessing over for months. My mouth is watering thinking about it again.
But instead he just looked down at me, calm as ever, and said, “Spread your legs and jerk off for me.”
Of course I froze but he only repeated himself. It’s strange because even right then, even naked and hard on his bed with the porn was still playing in the background, I didn’t want him fully seeing my tiny dick. But his eyes were locked on me, waiting, and I wanted to please him. So I did it. I pulled my knees up and apart, spreading wide for him to see all of me.
He grinned again and told me what a beautiful little clit I had.
The words hit me like a slap and a caress at the same time. My face burned, but something deep inside shifted, clicked into place. Yeah. That’s what it was. Not a dick. A clit. Small, useless for anything but looking pathetic next to what he had. I must’ve whimpered or nodded or something because he kept going, voice steady and sure.
“That’s right. You don’t have a dick. You’ve got a pretty little clit. And from now on you’re my little princess.
I just sat there nodding, legs still spread, clit still leaking. Then he told me to stroke my clit again and I did. My thumb and index finger stroked like I always did in the dark. Slow at first, eyes flicking up to his face, then dropping back to that massive cock standing proud in front of me. Every stroke felt humiliating and electric all at once. And he just watched, not touching himself, but his cock fully hard and bobbing up and down.
And he just let me perform for him, that grin never leaving his face.
“Good girl,” he said. “Keep going. Let Daddy see how needy that little clit gets.”
That was the first time I came in front of Daddy and what kickstarted my near year transformation as his devoted sissy wife.

[sissy mike @str8sissymike]

Sorry for the lack of updates guys. Just been busy enjoying my life as daddy's full-time sissy. Can you tell I've fully embraced my new lifestyle? It just feels right.

[sissy mike @str8sissymike]

Every daddy needs a sissy for Valentine's Day.

[sissy mike @str8sissymike]

A very eventful Valentine's Day. Daddy wanted me to pose for him out in the balcony before fucking me. First time getting fucked in a semi-public area. Have to admit it really turned me on as the sound of my ass clapping against daddy filled the night. Here's to more romantic evenings to come.

[sissy mike @str8sissymike]

Daddy bred the hell out of me last night. Said I was turning into an insatiable whore. Think he wants to share me with another daddy and have a threesome. Since I'm becoming a pro a taking one cock why not two?

[sissy mike @str8sissymike]

It's never too late to live your truth.

[sissy mike @str8sissymike]

Gained a bit of weight during my vacation, but maybe in all the right places? Changed into the sissy outfit I've been meaning to put on at the gym bathroom for a while now. Even though it was locked, hearing a group of men talking just outside made me so nervous. Part of me wanted to invite them and get on my knees for them like a good girl. I'm starting to see the lasting transformation I'm going through since being with daddy.

[sissy mike @str8sissymike]

If you found out your gym partner secretly dressed like a sissy, what would you do?

[sissy mike @str8sissymike]

Sucked daddy off in this outfit today. Do I look like a good cock sucking sissy?

[sissy mike @str8sissymike]

Anyone looking for a booty call?

[sissy mike @str8sissymike]

Got convinced to go to a conversion therapy retreat for a few months. A few weeks out and I'm dressing like this again. Do you guys think it worked?

[sissy mike @str8sissymike]

A lot has changed since getting married in 2021 to now. From what society expected of me to what I was always meant to be. Despite all the challenges I had to go through, I'm glad I ended up with someone like daddy. Which role do you think suits me more?

[KendalKarlson ⭐🔞🔥 @KarlsonKendal]

What? Can u see up my skirt or something? 🤷‍♂️

[Ellie sissy 👅❤️💋 @Elliesis1993]

Who wants to @ my ex gf and tell her I’m a bigger slut that her?

💖💋🥰

[Ellie sissy 👅❤️💋 @Elliesis1993]

I swear I’m still an alpha straight guy bro….

🥰💖

#sissy #femboy #bbc #uk #bro

[Spicee @puppyspicee]

¿Quién me da bibe?

[Spicee @puppyspicee]

Tan atrevida