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Chapter 14
by
smalldickryder
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Dick Ryder the Dick Rider
You couldn’t keep living in two worlds on one phone anymore.The constant switching between loving husband texts to your wife and filthy “breed my married ass” messages to trans women was driving you insane. So you did what any good salesman would do: you created a clean business expense.You bought a second phone — a cheap burner you listed as a “work cell” for vendor coordination. On this phone lived Dick Ryder.The profile was pure filth:@DickRyder69
“Married conservative salesman & father by day. Tiny clitty sissy slut by night. 2.75” thick little dicklet. Love being exposed, caged, and used by superior cock. My tradwife has no idea her husband takes dick better than she does.”You filled it with the best photos and videos from the road: caged clitty comparisons, ass-up plug shots, cum-covered face pics, and short clips of you moaning like a whore while riding dildos in hotel rooms. The bio made it clear, you were a secret sissy begging to be ruined.The responses came instantly. Your inbox flooded.
Day 1 – Hookup 1 happened that same night after a long day selling at a rally. Riley was a tall, athletic trans woman with long black hair, toned legs, and a thick 8-inch cock she loved showing off.
She met you at your hotel bar, dressed in a tight black dress. Within twenty minutes you were in your room.Riley didn’t waste time. She pushed you against the wall, yanked your pants down, and laughed when she saw your caged clitty.“Fuck, it really is tiny,” she grinned, flicking the cage. “Your poor wife has no idea she married a little dick sissy.”
She unlocked you just long enough to compare, then made you drop to your knees. You worshipped her cock for nearly thirty minutes sucking, licking her balls, and burying your tongue in her ass while she called you her “secret conservative cumrag.”
She fucked you bent over the desk first, then on your back with your legs on her shoulders so you could watch her thick cock disappear inside you. Every deep thrust made your itty bitty clitty flop and leak. She laughed the entire time.“Look at that pathetic little thing. It can’t even get fully hard while I ruin your married ass.”
You came hands-free, spurting weakly onto your own stomach while she pounded you. She pulled out and painted your face with her load, then made you thank her while still dressed in your conservative event polo.
you were in a different city. Sasha was a curvy blonde trans woman with heavy breasts and a monstrously thick cock. She was even more dominant than Riley.
She made you meet her at a discrete Airbnb. The second you walked in she had you stripped and on your knees.“Send your wife a picture of you smiling like a good husband,” she ordered. You did it smiling innocently while Sasha’s thick cock rested across your face. She made you caption it “Missing my beautiful wife ” before she started using you.Sasha spent over an hour breaking you.She sat on your face and made you eat her ass while she stroked her huge cock. Then she fucked your throat until you were gagging and crying. When she finally fucked your ass, she went slow and deep, making you feel every inch.“Tell me how much better my cock is than your wife’s pussy,” she demanded, pinning you down.“It’s so much better,” you moaned like a slut. “I love trans cock more than I love my wife.”She laughed and made you cum hands-free twice before flooding your guts. Afterward she took pictures of your gaping, cum-leaking hole next to your tiny soft clitty for your secret account. The third and most intense was Jade, a gorgeous black trans woman with an absolutely massive cock, thick ass, and a cruel streak.She picked you up after an evening event. You barely made it back to the hotel before she had you dressed in panties and stockings.Jade was verbal and vicious.She made you kneel and worship her massive cock for a long time, slapping it across your face while she recorded. “This is what a real man’s cock looks like, you tiny-dick conservative bitch. Your wife could never handle this.”
She fucked you in every position imaginable. Missionary so you could see her heavy tits bouncing while she stretched you. Doggy while she pulled your hair and called you her “MAGA sissy.” And finally riding her reverse cowgirl so she could watch your caged clitty bounce uselessly.Every time you got close she stopped and edged you mercilessly.
“Beg for my superior black cock,” she demanded.“Please… please breed me,” you whimpered. “I’m just a pathetic little white sissy with a tiny clitty. My wife deserves better than me.”She finally let you cum while she flooded your ass, laughing as your locked clitty dribbled pathetically.Through all of it you kept up appearances.You called your wife every night, told her you loved her and missed her. You sold merch, shook hands with politicians, and smiled for photos like the proud conservative family man you were supposed to be.
But every spare moment was spent as Dick Ryder chatting with trans women, posting humiliating content, and getting used in hotel rooms across the country.
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Shifting Perspectives
Hate and Love are very similar
You are a conservative who sells conservative merch to fund your tradfamily.
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- Gay, Cuck, SPH, Femdom, Impotence, Anal play, Transgender, Transwoman, Anal, Oral, Ass to mouth, Small penis humiliation, Size comparison, Sissy, Cage, Butt plug, Eating ass, Dildo, Sex toy, Measuring, Crossdressing, Blowjob
Updated on May 12, 2026
by smalldickryder
Created on May 11, 2026
by smalldickryder
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