Crossdressed, Trapped, and Humiliated on the Open Road

Becoming Her: A Moment of Transformation

Jordan has spent weeks planning for today, the perfect Sunday. While he may have normally been a quiet and perhaps awkward guy, today was just about him.

A few weeks of planning had gone into today. Looking online and doing some shopping to find the perfect outfit for today. It was shipped and delivered earlier this week. It had sat, waiting in his living room, ever since Wednesday. A Pandora’s box of delight.

Every time his eyes caught sight of that box, his heart raced ever so slightly. He had come home every day and saw it sitting there. The sight of it caused even the worst stress of that day to fade away. All that excitement had led to today.

Cutting open the box and peeling away the tape, folding the flaps open, and pulling out the dress. A soft, powder-blue sundress with lace at the hem. Delicate flowers are embroidered around the collar. It felt as light and as breezy as he had imagined it would from the images online.

His starchy, stiff white shirt felt like a prison in comparison. He couldn’t throw it off himself fast enough. His shorts followed soon after.

He had let the excitement get to him a bit yesterday, and he had already slipped into a pair of black lace panties. He had kept the matching bra off to the side. Along it sat two blobs of flesh-covered silicone he had gotten online as well.

It was always one of his favorite parts of the transformation. Feeling the weight sag onto his chest and his body gaining that feminine curve.

There was a strong pull to put the rest of the transformation aside. He threw the dress on right away, but he knew there was more to go.

A quick trip to the bathroom and pulling out his make-up bag, he began to really get ready. A light foundation to smooth his complexion. Ruby red lipstick to make them pop. Winged eyeliner to make him look fierce.

Then came the dress. It felt as light as clouds as it draped itself over his shoulder. The swish of the skirt electrified him through and through. The slightest movement sent the lightweight fabric into the most beautiful of motions. A spin caused the fabric to flow upwards from the wind and then drop dramatically.

He could’ve stayed home and had a lovely day, but that wasn’t the plan. His heart pounded as he stared at the door. He had made the decision earlier. Today would be the day.

A white cardigan went over his dress and arms to help keep him warm. A nice purse was slung over one shoulder, and stuffed inside it were his wallet and phone. There was one last stop in front of the hallway mirror as he tried to see if there was anything that would give him away.

There was some hesitation. His confidence was growing. With his heartbeat pounding away, he decided to skip the sunglasses to help his face and strode out the door.

A Drive into Disaster

He settled into my car seat and drummed his fingers on the steering wheel. Butterflies surged into my stomach as he seemed to be about to develop cold feet.

A few deep breaths, hand on the gearshift, and then I shifted gears and drove off. It would only be a short drive; hit up the park and step outside for a quick pic. That was it!

The radio was tuned to the local radio station. Some soft music only accentuates the sleepy town vibes. The day was still starting off, and the sun cast a warm glow over the streets. It was a perfect day—just him, the open road, and the wind brushing through his hair.

The streets and sidewalks were all quiet. He caught sight of a few people out, walking their dogs. A few were out for a morning jog to get exercise in, but the streets were still quiet and calm. This only allowed him to build up his confidence. Everything would be alright. It would be a short drive to the park.

There was a moment of pause as he pulled in front of the parking lot. While he had tried to plan everything out, the one thing he forgot to look into was the local park. The parking lot was currently closed due to maintenance.

There was still parking allowed on the street. So he was able to just idle the car in the street for a little bit as he thought about the next step.

He thought things through, drumming his fingers along the steering wheel. His eyes flashed down, and he saw his elegantly done nails. A fresh coat of light blue polish on it. This was still a pretty big step forward for him.

He had gone out. That was enough. He could make another trip to the park at a later date. With a heavy sigh, he let his hands rest on the gear.

The Crash That Changed Everything

The entire car jolted forward as the sound of a metal-on-metal impact rang in Jordan’s ears. His heartbeat accelerated as his hands dug into the steering wheel. His nails left a tight imprint on it. Slowly and with great trepidation, he lifted his head and looked around.

Another car had rear-ended him, and the driver was getting out. He could already hear her babbling out some kind of excuse, “Oh my god, I am so sorry, I didn’t know you were parked. I got distracted for like five minutes, and I am so sorry.”

Nowhere to Run, Nowhere to Hide

There was a strong urge to hide in the car. Hoping she went away definitely pulsed through Jordan’s mind. However, there was a strong doubt that it would happen. She was already approaching the window, giving his car a once-over.

“Looks like the damage isn’t bad. Your rear end looks good,” she stated before realizing what she said. She offered a small chuckle, “Oops, I mean, your car’s rear end. I am so sorry again. Are you alright?”

Okay, so his car was fine. Everything was still going fine, and he could still just drive off and hide and;

Knock-Knock.

She was now at his window, and he could see her. She looked to be a good bit older than him. She had the look of someone who took good care of herself. There were a few crow’s feet here and there, but a clean face and an impeccable sense of fashion. Jordan almost felt jealous of her outfit.

“I’m alright,” he squeaked out. He was almost tempted to add, ‘just go away’ under his breath.

The older woman paused outside his car, looking in at him. “Are you sure?”

“Yes, I’m fine. If the car is fine, I’ll just be on my way.” He couldn’t help it, and the embarrassment was too much. He wanted it to be over. He turned the key in the ignition and…

The car chugged, refusing to turn over. Vrm, vrm, vrm….silence.

He tried again. Felt his cheeks flush with further embarrassment as the woman didn’t walk away. She stood there watching him desperately try to turn the keys. The car once again made some noises before settling into an unworking silence.

“I am so sorry.”

“It’s okay, it’s okay. It was always a clunker. On its last legs,” Jordan choked. The humiliation was real. He’d have to call a tow truck and a cab, all while dressed like this. He could just imagine giving his billing info with his real name and address to some tow truck driver. All while in a short dress and heels and…

“There, there, sweetie,” the older woman crooned as she reached into her purse. She pulled out some tissues. “Your mascara is starting to run.”

A Ride He Couldn’t Refuse

Through a few rough sniffles, Jordan accepted the proffered tissue. Using it to wipe his face, “I’ll be okay, just not looking forward to…everything. The tow truck, the cab ride home with a stranger.”

“I can give you a ride,” she beamed. “Really, it is the least I can do.”

Jordan smiled slightly; it was nice. It would avoid some of the humiliation, at least. She had already seen him dressed up, and he seemed like a genuine, gentle soul. “Yes, I think I would like that.”

“In the meantime, Miss,” she stated with a slight waggle, “you will have to tell me where you got that dress. It looks great on you!”