Posts of "Urban" from "patreon"

If you really want me - Part 1

Hey, I'm Ted. I had a really good childhood, you know? My parents, Bob and Alice Smith, were awesome. And Cara, my sister, she was four years older and just like a goddess to me (she was super into Disney back then). Plus, we had Ria, our dog. We lived in a nice house, always had plenty of food, a warm bed, friends, school – I even had a motocross bike!We were just a solid middle-class family, living in this suburb called Pleasantville. We were super close. Honestly, no matter what happene...

He Wasn't Even A Boy! - Chapter 4

OTHER CHAPTERS | ALL STORY LISTDisclaimer: All characters depicted in this story are 18 years of age or older at the time of the events described. This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.&#34...

They Think I am a Woman! - Part 3

OTHER PARTS | ALL STORY LISTBefore I knew it, Sheila had me back on my feet with a little help from a spotty McDonald's helper, who looked like Ronald McDonald's son. I was whisked into the ladies' toilet (another thing to add further horror to my already battered senses). Luckily, there was no one in the toilet. I think I would have died if there were. 'Sheila, let me go home, please!' 'Now don't be a silly girl, Toni. You only slipped and fell over, no big deal.&#39...

They Think I am a Woman! - Part 2

OTHER PARTS | ALL STORY LISTFor some reason, Mr Percy was dancing rumbas in my panties, trying to break free from its nylon prison. I could not believe that I was the same person.'Wow.' I said with awe.As I looked at my new self, I realized that I was the spitting image of my mother. OK, not exactly, but probably when she was a girl about my age. My mum always dressed young and could have been my older sister in the photo I have on my shelf in the flat.I realised that to see my mother, a...

The Girl He Could Be - Part 7

OTHER PARTS| ALL STORY LISTTim was relieved. He couldn’t imagine what it would be like trying to live here and keep up his charade.Patty and Nancy had better imaginations. Nancy could just picture it. Tim would go crazy here. Mrs. Brown would mother him like he was her own daughter. Mr. Brown would probably be all right with it; she was neat. Jeff and his little brother would like it just fine, too. Patty thought it would be fun, but not yet.Tim wasn’t ready yet. He wasn’t feminized enough...

They Think I am a Woman! - Part 1

OTHER PARTS | ALL STORY LIST'I'll have to ring them. Let them know about the mistake.'What job were you going after, hun?' said Sheila.I went a bit red.'Erm, secretary.'I hurriedly explained. 'The job didn't say anything about being male or female, and anyway, they can't discriminate anymore. There are laws against it.'Sheila looked at me with an amused expression on her face.'Sure, Tony, do you really believe what you are saying?' There are a few ...

They Think I am a Woman! - Intro

He Wasn't Even A Boy! - Chapter 3

OTHER CHAPTERS | ALL STORY LISTDisclaimer: All characters depicted in this story are 18 years of age or older at the time of the events described. This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.The ...

The Girl He Could Be - Part 6

OTHER PARTS| ALL STORY LISTOctober in Florida was still very warm, and the heat rose from the pavement as they walked to Pam's car. The cool breeze, blowing through his hair as they drove with the windows down, felt wonderful. He looked up at the small, white, puffy clouds, and his heart soared. His wildest dream was coming true. They waited in the car while Patty went in for the cash. Tim tucked the two hundred dollars in his purse. It was amazing how comfortable he felt out in the daylight...

Only Man In office - Part 12

OTHER PARTS| ALL STORY LISTPlease tell Mrs. Sharp that we discussed that solution and that you will do that only because of the conditions of the new contract with Mrs. Sinclair. She will be more than happy to hear that.But you have to ask her to give you a corresponding salary increase. And she has to get you a new female driver's license and ID. Please tell her exactly that, too. But now let's go to bed, my dear; it was a long day for you." With that, she hugged him and pulled him ...

Only Man In office - Part 11

OTHER PARTS| ALL STORY LISTWhen Michelle was presentable again, she went back to Mrs. Sinclair, and both watched Mrs. Sharp being properly fucked on her desk for some time.After a minute, Mrs. Sinclair grabbed Michael's hand and took him with her. She left the office with him in tow, closed the door, and when they reached Michael's desk, she had him sit down there."Michelle, dear, you heard my promise. Please open up a new contract file on your computer and start taking some dictatio...

Only Man In office - Part 10

OTHER PARTS| ALL STORY LISTDue to Patreon’s rules, I had to publish Only Man In Office - Part 10 on my Blogger site instead. You can now read the first chapter there.Link - https://urbanstoriess101.blogspot.com/2025/05/only-man-in-office-part-10.html

He Wasn't Even A Boy! - Chapter 2

OTHER CHAPTERS | ALL STORY LISTDisclaimer: All characters depicted in this story are 18 years of age or older at the time of the events described. This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.More...

He Wasn't Even A Boy! - Chapter 1

OTHER CHAPTERS | ALL STORY LISTDue to Patreon’s rules, I had to publish He Wasn't Even A Boy! - Chapter 1 on my Blogger site instead. You can now read the first chapter there.Link - https://urbanstoriess101.blogspot.com/2025/05/he-wasnt-even-boy-chapter-1.html

The Girl He Could Be - Part 5

OTHER PARTS| ALL STORY LISTDisclaimer: All characters depicted in this story are 18 years of age or older at the time of the events described. This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.Concentr...

Relationship With Crossdressing - Office Family, Matter - Chapter 3

OTHER CHAPTERS | ALL STORY LISTThe revised dress code policy sat in Tommy’s inbox like a hard-won trophy, its bold, unambiguous language a stark contrast to the vague corporate-speak he’d grown used to. He read it again over his morning coffee, savoring the words: Employees are free to dress in alignment with their gender expression. No asterisks, no caveats. Just permission finally to exist as himself.Rachel appeared at his desk with two coffees in hand, her grin sharp with victory. “To n...

Only Man In office - Part 9

OTHER PARTS| ALL STORY LISTDisclaimer: This work is intended for a mature audience and complies with all applicable content guidelines regarding age-appropriate material. It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions. Reader discretion is advised. Enjoy responsibly within the context of fantasy.When Michael went to work the next morning, everything seemed so normal for him: shaving all over, applying make...

He Wasn't Even A Guy! - Intro

ALL STORY LIST | Chapters - CH 1 | CH 2 | CH 3 | CH 4 | CH 5 | CH 6 | CH 7 | CH 8 | CH 9 | CH 10 | CH 11 | CH 13 | CH 14 | CH 15 | CH 16 - 17 | CH 18 - 19 | CH 20It is purely fictional and intended for entertainment purposes only. The content is not meant to promote or endorse any real-life actions.Reader discretion is advised. Enjoy responsibly within the context of fantasy.Coach Bradford called out the times as I ran past. Right on schedule. One lap down, three to go. Tilden was just where I w...

Relationship With Crossdressing - Office Family, Matter - Chapter 2

OTHER CHAPTERS | ALL STORY LISTThe revised dress code policy landed in everyone’s inbox at precisely 8:03 AM on Monday, the same time corporate HR always sent out their bland, bureaucratic announcements. Tommy had been refreshing his email since six, with a mix of anticipation and dread. When the notification finally popped up, he nearly dropped his coffee.He read it once, then twice, his fingers hovering over the trackpad as if the words might dissolve if he touched them.Gone were the vague p...

The Girl He Could Be - Part 4

OTHER PARTS| ALL STORY LISTThey watched the girls turn into the high school parking lot. The guys had been waiting for half an hour."You’re late." Jim bellowed as he opened the front door. "Where’s Pam? We can’t all fit in here." There were four of them and four girls.Tim knew them all by sight. They were all jocks, and except for Jim and Jeff, they were huge. Only one had ever beaten him up.That was Randy, Sue’s boyfriend. It had been almost two years, and Tim prayed he ...

Only Man In office - Part 8

OTHER PARTS| ALL STORY LISTToday at the opera, there was a performance of 'Aida.' A lot of people wanted to watch the show, and there was a crowd of people standing in front of the opera house.When the limo stopped before the main entrance and the driver opened the doors and helped the ladies get out of the car, they made a little show of themselves. A good-looking gentleman with three amazingly dressed ladies is always good to get some attention.There was even a red carpet on the way to...

The Girl He Could Be - Part 3

OTHER PARTS| ALL STORY LISTNancy turned to Pam. "I know who that girl is." She couldn’t believe what she saw."Who is she?" Why the melodramatics? Pam wondered.Nancy started walking fast, pulling her friend along with her. "That ‘girl’ is not a girl. That ‘girl’ is Tim Hynes." She wanted to catch up to him."You’re kidding!" She was shocked. "Isn’t that the kid in your grade that you went out with once?" Pam knew Nancy wasn’t kidding. She tho...

Working In A Beauty Salon - Finale Part

OTHER PARTS| ALL STORY LISTThe salon's usual hum of blow dryers and chatter died instantly as Alex stepped through the door, the bell's cheerful chime sounding grotesquely out of place. Hugo felt the shampoo bottle slip from his fingers, hitting the tile with a dull thud that echoed in the sudden silence. His pulse roared in his ears as Alex's polished dress shoes clicked across the floor, each step measured like a predator circling prey."Luna," Alex said again, extending the...

Relationship With Crossdressing - Office Family, Matter - Chapter 1

ALL STORY LIST | CHAPTERS - CH 2 | CH 3Note: This is a completely separate story and not a continuation of 'Relationship With Crossdressing - Family Matter'. It follows a different plot, setting, and characters unrelated to the previous story.The office buzzed with its usual Monday energy, keyboards clacking, coffee machines hissing, and the occasional burst of laughter from the break room. Tommy adjusted the hem of his fitted blazer, the soft fabric brushing against the lace-trimmed cam...

Only Man In office - Part 7

OTHER PARTS| ALL STORY LISTWhen Michael talked to his wife in the evening, he told her how the day went and that Mrs. Sinclair and Mrs. Sharp were really pleased with him. Christine was really pleased to hear that too. Even when Michael asked her if she was ok with him being on duty as a waiter for Mrs. Sinclair and the company party, she agreed."I think it is a wonderful opportunity for you to become accustomed to serving a lot of women, and it would improve your serving knowledge. And mayb...

The Girl He Could Be - Part 2

OTHER PARTS| ALL STORY LISTTim headed for the juniors' department.This time he would ask for help immediately when a girl showed up. He took a second to check his hair again in a mirror. He couldn't see anything wrong with it. It must have been his imagination, he decided. He skirted the department, looking for what he wanted. When he spotted the displays of shorts, he turned in between the racks.There were several girls in the area, but they were busy in their own search for what they w...

Relationship With Crossdressing - Family Matter

ALL STORY LISTThere is nothing sexier than a pair of beautiful, shapely legs in sheer stockings under a short skirt with a little lace showing at the hem, all perched on a pair of beautiful high heels.Well, maybe with the exception of a beautifully shiny, long, flowing mane of hair, a beautifully made-up face, and a pair of beautiful, ample breasts peeking out of a sheer top or lacy dress. These things are what I find sexy.It doesn't matter to me who is underneath these things, be it a woman...

I Can Wear A Skirt To Work - Chapter 9

OTHER CHAPTERS| ALL STORY LISTSaturday morning, I awakened late. I wrapped myself with the only robe available in this room, a negligee left over from a previous night’s gown. Out in the hall, I discovered that the door to my bedroom, or rather, of late, Kate's was ajar. I knocked; she wasn’t here. Neither was her car in the driveway. A quick survey of the bedroom confirmed that she’d moved out. Ted’s belongings were back in place.I caught my breath at that thought. I had actually th...

I Can Wear A Skirt To Work - Chapter 8

OTHER CHAPTERS| ALL STORY LISTTuesday morning, I awakened in a disoriented state. I still wasn’t used to sleeping in filmy nylon, plus I wasn’t in my own bedroom. It only lasted a moment, then I remembered that this WAS my bedroom, after all for the duration of the week.There was a knock at the door. That brought me fully awake in alarm until it sank in that it had to be Kate. An earlier knock had been what had awakened me at first."Hello," I called out."Shake out the cobwebs, sl...

I Can Wear A Skirt To Work - Chapter 7

OTHER CHAPTERS| ALL STORY LISTSunday morning, I was awakened by a thumping sound. Wrapping a robe around myself, I trudged my front door and opened it. Kate said nothing; she just stood there.It wasn’t necessary to ask why she was there, even at such an early hour; the large case resting at her side told all.I exhaled in a sigh, breaking the silence, "Come on in.""Thank you."Observing that she was fully made up, I asked, "You got up awfully early, didn’t you?""I d...