Ethan had been watching his twin sister with envy for many years now. Not so much her, but her clothes. The jealousy was driven by what Ethan was coming to recognize as his over-developed fashion sense. He loathed the lack of style in boy’s wear available to him.

He looked down and sneered at the white briefs he wore.  He looked over at the open bathroom door.  He could see right through it to the open door into Madison’s bedroom. It was like her bedroom was calling to him. Come look. Come look!

He and Madison were best friends. They shared everything. The bathroom doors had never been closed. They had no body shyness with each other. While Madison grew into a beautiful and curvy teen, Ethan resorted to body-building exercises as his only source to develop his chest to match.

Madison’s clothes got sexier as she developed. Ethan’s stayed the same. They shared everything except Ethan’s secret desire to dress like his sister, to be identical twins.

Madison would be gone for several hours, and here were the open doors, daring him. But, up until today, Ethan had resisted that dare. His desire had grown. He could no longer resist. He quickly crossed into his sister’s room with his heart pounding and stood before her vanity. He knew she kept her undies in the left-hand drawer.

Ethan slowly drew the drawer open and stared in wonder at the variety of colors, types, and textures. There seemed to be hundreds of panties here. In contrast, Ethan’s drawer had eight balls of white and plenty of room for his socks!

Ethan ran his fingers through Madison’s panties, feeling the different textures. He felt his cock stir. He whipped off his briefs and tossed them back into the bathroom. His briefs landed on the rim of the wastebasket.  Good, that’s where they belong!

Ethan’s cock got hard as he considered his next action.  While he desired to dress sexy, like his sister, he had no desire to be a girl. He loved his cock. He loved playing with it. Like every boy he knew, he wanted to push his cock deep into a willing pussy.

Ethan’s fingers found a pair of silky panties. He pulled the burgundy-colored panties out and wrapped them around his stiff cock. It felt so good! He stroked hard and fast, coming in seconds. He brought the soiled panties up to his nose and sniffed deeply.

The scent of fresh sperm kept his cock hard. He licked and sucked the panties clean. Ethan loved the taste of his spunk. Another secret he kept from his sister. He rubbed the damp panties over his face and down onto his chest. He kept going, stroking his thighs and ass.

Being on the school’s swim team gave Ethan the excuse to keep his body hair-free. Ethan’s cock throbbed as he slowly slipped the panties up his smooth legs. He settled his balls into the crotch of the panties and let his cock stand proud. The panties were cut too low to contain his hard-on.

Ethan pushed the drawer closed and slid open the one on the right, where his sister kept her bras. He found a matching burgundy camisole and pulled it over his well-developed breast muscles. He then sat down in front of the vanity’s mirror.

Ethan had been paying attention to Madison when she did her makeup, even assisting her on occasion. He knew how to apply the foundation and the various colors to turn his plain masculine face into a cute feminine one.

When she was done, she studied her image carefully. Wow, this is Thena! Overcome with emotion, Thena came again. She scooped her come up with her fingers and delivered it to her waiting tongue. She sucked her fingers clean.

Today’s activities were enough for the first time. Thena cleaned everything up, leaving no trace, and returned to Ethan.

~~~

Thena enjoyed several private sessions fully dressed and learning to walk in heels. She even ordered several wigs to complete her transformation. These sessions always ended in sperm blasting orgasms.

The school pool closed for maintenance for a week. As a result, Ethan’s swim team met in a classroom for ‘Health’ lessons. Since there would be no changing in front of others in an open locker room, Ethan decided to wear his sister’s sexy underwear to school each day.

Having girl’s garments under his school uniform was highly arousing. Nobody suspected. It was his secret taboo. He could feel them all day. Normal Ethan among his friends and classmates, with lace panties and a bra. Thena was hiding in plain sight. He spent hours masturbating each night.

When he got to the classroom today, he found the door locked. A note stated the pool was open, and the swim team was to report to practice. Ethan was scared shitless. How would he change while wearing his sister’s underwear?

The last school period was when all the sports teams practiced. The gym locker room was packed as usual when Ethan arrived. He opened his locker and grabbed his swimsuit. Then, making excuses about needing to shit, he headed for the toilet stalls.

Ethan successfully changed and got back to his locker, hiding his sister’s things in his uniform. After the regular team practice, Ethan asked the coach if he could swim extra laps to improve his breaststroke. The additional training would take time so he could be the last one in the locker room.

Swimming the extra laps did the trick. By the time Ethan returned to the locker room, the place was deserted. However, he still took the precaution to change in a toilet stall. He failed to notice that the lock didn’t latch when he closed the stall door.

He had the bra on and was just slipping the panties up when the door swung open. A mountain of a boy stood blocking the opening. A very naked boy with muscles on muscles. Putting on Madison’s panties always gave Ethan a hard-on.  His hard-on sticking out was now on full display to the boy looking in.

“I thought I saw lace panties flash under the door. Wow, you look HOT!” The boy fell to his knees and took Ethan’s cock into his mouth.

The warm mouth sucking and licking Ethan’s cock felt incredible. Ethan had only gone so far as making out before. That had always been with girls. So this was his first sexual experience. Ethan found that he didn’t care that it was a boy doing it. The blowjob just felt great.

Ethan’s cock was longer than most of the other boy’s. It was also thinner. He watched with delight as the sucking boy’s cock swelled to hardness. It was as long as Ethan’s but twice as thick. He found himself lusting for that cock, wanting to draw out the waiting semen and swallow it.

These new homosexual thoughts, and the boy’s mouth, had Ethan coming in record time. He filled the boy’s mouth with a huge load.

“What’s your name? Can I suck your cock?” Ethan asked.

“I’m Timmy. I love having my cock sucked and my ass pounded. But not here. Let’s go to my place.” Tim offered.

~~~

They spent the next two hours sucking and fucking each other. Timmy insisted Ethan wear his sister’s bra and panties. They even experienced showering together to clean off the sweat and dried semen. Ethan enjoyed losing his virginity to Tim. However, he was still looking forward to his first pussy.

Timmy asked if Ethan ever wore a dress. Ethan explained he became Thena when wholly dressed as a girl. Then, Timmy asked if Thena would go out on a date with him.  Ethan leaped at the chance.

~~~

Ethan didn’t want anything from his sister’s closet for Thena’s date. So he got online and ordered the dress, shoes, and all the accessories.  Thena did some trial sessions, testing different makeup, wigs, and accessories until she got the look just right.  One she knew Timmy would be pleased to take out.

There was no way Ethan could change into Thena on a Friday night in his home, so he reserved a hotel room near the restaurant Timmy had chosen.

Ethan packed everything into his backpack in the morning. After school, he took Uber to the hotel to have plenty of time to get ready.  Thena planned a bubble bath to soften her skin and sweeten her scent.

After her bath, Thena started on her makeup. It was early, so she took her time. After her makeup was perfect, she sparingly applied a classic perfume, Chanel #5.

At 6 PM, Thena had finished dressing and was buckling her shoes when her cell rang. Timmy was waiting for her in the lobby.

Timmy was mesmerized when he spotted Thena leaving the elevator. She was wearing a blue satin dress with a tightly fitted bodice and a pleated skirt.  The dress was low cut across the bust, leaving Thena’s shoulders and arms bare.

In addition, there were blue lace straps that went over each shoulder. The pleated skirt flared out with the hint of blue petticoats beneath. The dress only came down to mid-thigh. Blue fabric roses were attached, starting at the right shoulder and going diagonally down to the hem at the left thigh.

Thena wore matching blue high heels. Her thigh-high stockings were white net style with satin tops that left several inches of thigh bare under the dress. In addition, she wore white transparent gloves with satin and pearl cuffs at the wrist.

She also had a blue lace and satin ribbon tied in her hair that kept her long, wavey locks behind her shoulders. Her auburn waves fell to her lower back. Her ensemble was completed with a neckless of tiny white pearls dusting her neckline.

Thena had done her exquisite makeup slightly heavy to accommodate the low light of the restaurant and theatre. To Timmy, she looked like a teen angel. He was in love! Knowing she had a long cock to pound deep into his ass was a bonus.

Timmy was wearing a well-tailored sports suit without the tie. His masculine bulk made Thena feel petite and feminine next to him, even though Ethan was an average-sized boy for his age.  They made a good-looking couple.

~~~

The couple had a lovely dinner at an upscale steakhouse.  Timmy had been carded, so the staff knew they were under twenty-one and wouldn’t be served alcohol. The staff treated Thena with every courtesy, never suspecting she had a cock.

Timmy couldn’t keep his hands off Thena, rubbing her shoulders and back, squeezing her thighs. He would also slip his hand under the dress and stroke Thena’s hard-on. Thena returned that gesture with interest, keeping Timmy just as hard.

They proceeded to the play, a comedy about modern relationships that had them laughing until their sides were sore. In the press of intermission, Timmy was able to snag a couple of glasses of wine.

~~~

When the evening was done, they returned to Thena’s hotel room. She excused herself to ‘slip into something more comfortable.’ She returned wearing sheer burgundy babydoll lingerie with matching G-string panties.  Her hard nipples were clearly on display. Her even harder cock was also showing.

Timmy was frantically attempting to undress. Thena stopped him and offered to do it. She slowly removed each garment, stroking and kissing whatever was exposed by the removal. By the time Timmy was naked, he was on the verge of an orgasm.

Thena stroked his cock hard and fast, then popped his cock into her mouth to get Timmy’s first orgasm out of the way. Then, she swallowed his semen and looked up into Timmy’s eyes with a big smile and a wink.

The rest of the night was filled with hard fucking and sucking as befit boys their age. Thena in lingerie only increased both of their carnal desires.

~~~

Thena went on several more dates with Timmy. Ethan and Timmy became best buddies as well. Timmy was happy to have sex with either. Unfortunately, it all came to an end when Tim’s family moved out of the state.

When his twin sister, Madison, learned he was no longer a virgin and wanted details, all Ethan answered was, “I’m a Gentleman. I won’t tell.”