First time at the theater (closed to JDrew)

[Dannyfunn63]

Dan has dressed up in his wife's things many times. Like the entire 15 years they've been married. He loved feeling sexy in her things. She would travel a lot for work and he would spend days dressed.

As things wore on, he found himself not enjoying it as much, so he started dressing and going to a Webcam site. He would show off for the men and do as they asked while he was all dolled up in clothes makeup and a wig he hid from his wife. But that wasn't enough anymore.

So there he stood in front of the mirror. He had on a skin tight black dress with a somewhat flow skirt that came down just above his knees. Knee high leather boots shimmered in the light. The blonde wig rested on his shoulders and the heavy makeup made it difficult to tell who he really was.

Dan wiggled as the panties were tighter than usual ... but he needed to hide things in the super tight cotton white panties. He took a few deep breaths and gave himself a pep talk. "It'll just be a drive. Maybe a walk somewhere where no one will be. Just go outside like this, then come home and jerk off."

He shook himself back to life and walked out the door. He stepped into his wife's small convertible, figuring it would feel more right - but he left the top up. He drove for an hour until he got lost. This was some neighborhood he didn't remember ... but then he saw it. ADULT THEATER

He grinned a bit, his dark red lipstick making his teeth appear even whiter. The car pulled into the lot and he took a big breath. He was trembling but determined. He stepped out and walked in. It was dimly lit and took him a moment to adjust. He saw magazines to one side, DVDs the other way. Straight ahead was racks of lingerie. He went there and started imaging what he'd look like in the items.

He wasn't quite paying attention around himself, not realizing man after man seemed to keep walking by down a hall just behind where Dan stood in his skimpy black dress and boots.

 

[JDrew]

Drew browsed the shelves looking for something, anything, to add excitement to his waning sex life. He picked up product after product, giving it a cursory glance, not finding anything he thought his wife, Maribel (Bella, for short) would ever consider adding to their awfully vanilla bedroom life. A remote controlled panty vibrator in the shape of a butterfly; an artisan, hand-made, glass dildo; metallic anal beads in rose gold—Bella would simply laugh.

Stopping at the Gemini Adult Book shop was a spur of the moment idea, although something Drew had considered many times in the past. This time of night traffic was light so no need to stay on the highway, cutting across the local roads was just as easy—maybe the only benefit to working late.

The sign out front was dimly lit and said Gifts, Toys, Videos and ADULT THEATER. Drew was just about even with the sign, going forty miles an hour, when he decided to slam on the brakes and swing into the parking lot.

Inside the store was bigger than it looked from the road. Rows and rows of everything from DVDs, lingerie, blow up dolls and one wall that featured the sign PARTY PLANNING STATION, filled the large room.

Drew browsed in the section: Inspired by Fifty Shades. Neckties, blindfolds and Princess Beads, Drew shook his head. It was all wrong—his wife would never go for any of it.

The realization that Drew wasn’t really there for this wife, that in reality, he was there for himself didn’t occur to him until he had decided to leave and was almost to the door. It was next to the leather leashes and collars that Drew considered finding something for himself. He spun around and found the aisle marked: For HIS Pleasure.

With a renewed purpose Drew started looking more critically at the offerings asking himself: What would I like?

He circled the aisle getting ideas and then moved to another section of the store to see what else might interest him. Near the lingerie he brushed past a woman with blonde hair and a short black dress, slight bumping into her. “Sorry,” he said quietly. The woman didn’t turn or say anything, just nodded. Was it odd to find a single women in a dingy adult shop, Drew wondered. He lingered behind her, glancing at her ass.

Another man passed by them and turned down a narrow dark hallway. Drew assumed it was for staff only until he saw the small sign that read: Theater. He remembered the large sign out front and his curiosity was piqued.

He had never been in an adult theater before but decided to check it out. He moved past the woman in the black dress once more. As he shuffled past her, he was for the second time that night, inspired to do something spur of the moment.

“I like your boots,” he whispered to the blonde.

 

[Dannyfunn63]

Dan felt people moving past him but never realized this man was right behind him. The words threw shivers down his entire body. He felt goose bumps across his body, which made his cock twitch and his nipples harden.

Dan turned and flashed a friendly smile through his dark red lips. He brushed the wig from his face and looked the man over. He was very cute. A bit conservative, but very cute. Dan didn't know if this man knew his secret, and Dan didn't know if he wanted the man to know or not.

Dan shyly turned and kept thumbing through some lingerie on the rack. He looked back over his shoulder and saw the man still staring at him.

He coughed and tried to fake his best female voice. "Thank you," Dan replied in a husky femme voice. "They are my favorite."

Dan saw the sign over this man's shoulder. THEATER. He wondered to himself if that was the booths he remembered in his younger days, or was it a legit theater with rows of seats.

Dan wanted to go investigate, but he didn't know if this man would follow him. Would he kick Dan's ass if he found out he was a guy? Dan's eyes kept darting between the man and the theater, torn on what his next move as he trembled slightly.

 

[JDrew]

Her voice was quiet and throaty. Reserved. Sexy. Drew glanced around looking for something to inspire a bit of conversation but could think of nothing that wouldn’t sound creepy. Drew returned her smile and in the somewhat awkward pause the followed, noticed that she kept glancing over his shoulder.

Perhaps she is waiting for someone, her thought.

“Well, you’re legs look great in them,” Drew said, his friendly smile broadening. “You should wear them often.”

He paused, not sure how to continue. “We’ll, I’m just lookin’ around … I’m just gonna keep … you know …” Drew made a short gesture down the aisle.

He tuned and began to walk away. The Theater sign glaring over his head. Not sure what to do, he went into the dark hallway.

 

[Dannyfunn63]

Dan trembled at every word this handsome man said. When he went down the hallway, Dan couldn't help but stare at this man. He was adorable and shy, not too intimidating. But would he feel the same way if he found out who Dan really was?

Dan waited for the man to turn a corner and then slowly walked into the theater hallway. He tried being discreet, but the heels of his boots clicked loudly in the hallway. He started to hear moans from the screen then noticed a couple men milling around the entrance.

Dan pushed the door open slightly and his eyes struggled to adjust to the darkness. He quickly darted into the back row and down a few chairs. He sat nervously and crossed his legs. He leaned back thinking he'd just enjoy the show when he looked down the aisle AND SAW THE MAN SHE JUST TALKED TO.

Was he as nervous as Dan? Did he dart to the backrow for quick exit too? Dan tried not to stare at this man as loud screens from a woman getting fucked doggystyle on the screen filled the room.

Dan kept trying to sneak peaks until one time he noticed the man doing the same. They caught eyes and flashed nervous smiles before Dan's head snapped back to the screen. He felt a strong desire combined with a strong fear. He tried not to look back, but when he did he noticed the man was on his feet scooting down the row!

 

[JDrew]

Drew clumsily slid into the seat next to the blonde. He lowered his head, his eyes looking down towards her shapely legs now exposed to mid-thigh.

“Hope you don’t mind,” Drew whispered.

He looked up at the blonde who shook her head and gave Drew a nervous smile. Even in the gloom and sporadic, dancing light coming off the screen, Drew could see that she was pretty but something else, too. She had some masculine features in her face—maybe it was her jawline, or cheekbones—Drew began to wonder if maybe she wasn’t a she at all.

On screen a closeup of the actresses hands gripping the arm of a chair. Cut to her face twisted in both pleasure and pain. Then a shot of a thick cock sliding into her tight asshole. She gasped and panted.

The thought of this sexy blonde being a man caught Drew off guard.
It didn’t scare him or revolt him. Instead Drew found himself curious.
An encounter with a feminine man, a crossdresser, would certainly be anything but vanilla, he thought.

Drew considered what he should do. He wanted to touch her, start something and see where it might lead.

The blonde didn’t move away from him, seemed pleased that he had moved closer.

Drew slowly reached out and laid his hand lightly on the smooth skin of the Blonde’s thigh.

 

[Dannyfunn63]

Dan's heart raced every moment this stranger was next to him. The moment the stranger touched his thigh, Dan gasped and his heart felt like it was beating through his chest (under the padded bra, of course).

Dan looked this man in the eye and bit his dark red lip. He smiled shyly and gave the man a concerned look.

"Please don't be mad, but ... "

His voice trailed off, not sure how to word it.

Dan reached over and watched as his finger, with its dark red painted nail, traced along the bulge in the stranger's jeans. "Don't be mad, but I've got one of these too."

Dan looked into the stranger's eyes while still tracing the now growing bulge. Dan braced himself for a punch, kick, anger, something. He figured he'd lay it on the line now to avoid anything worse.

"I have never sucked a real man before, and if you want nothing else than that just say so. If you want to run, I understand. If you want to punch me, I understand."

Dan kept trackng the bulge and noticed it kept throbbed and growing as he looked in this man's confused eyes. Dan decided to push the issue and leaned down to kiss the bulge through the jeans.

He slid back up and smiled shyly as he bit his lip. "A girl always needs her first dick."

 

[JDrew]

Drew wasn’t shocked. Wasn’t even mildly surprised that this stranger was in fact a man. What was surprising to Drew was that he found himself turned on. He surprised himself, just a little, for reclining deeper into the thin, worn fabric of the theater seat and clasping his hand around the back of the neck of the attractive stranger.

“I want you to suck me,” Drew whispered in quiet, hoarse voice.

The stranger offered a light, seductive smile and then began to fumble with Drew’s belt, the button on his jeans and then his zipper.

Last chance Drew thought. Last chance to turn away and never come back to this place. I could excuse myself and never see this person again. But Drew was entranced. The exotic crossdresser was the object of Drew’s desire. He wanted to feel this sexy stranger’s wet, red lips pressing on his cock.

The stranger tugged at drew’s jeans, pulling them down a few inches, enough to slip her hands into Drew’s underwear, grey and unremarkable, and lightly stroking the tips of Drew’s dick.

Drew closed his eyes and felt his cock stiffen and throb like he hadn’t felt in a long time.