Room Three Sixty Six

by Chicklet


Justin took a deep breath before stepping out of the door. Amy was out of town for the weekend, so he didn’t have to worry about her coming home and finding him gone. Hoisting the backpack over his shoulder, he slammed the door behind him, walking confidently towards the blue Toyota in the driveway. His keys were out and ready to unlock the door, and he threw the backpack into the passenger seat. Sitting down, he put his hands on the wheel, and took another deep breath.

Most people would say that this was the stupidest thing Justin had done in his whole sensible life. But no one was going to have the chance to voice that opinion since only one other person would ever know. Placing the key in the ignition, Justin turned on the car, music flooding the vehicle as he waited for the car to warm up a bit.

For he last six months, Justin had been waiting for this moment. He would be leaving his house as his ordinary self, but when he came back, he was sure he would be changed forever. Something that he had been fantasizing about for years was about to come true, something not even Amy knew about. Justin was on his way to a hotel downtown to meet a man he had met on a personals board online. The bag in the seat beside him contained clothing that he had purchased over the years behind his wife’s back; lingerie big enough to fit over his muscular frame. Panties, stockings, even a corset he had picked up at a specialty shop. The trips to the stores had been embarrassing, but exciting, as well. The looks the cashiers had given him sent shivers of excitement up and down his spine. They knew his secret; strangers he had never met knew of his secret lifestyle. Behind closed doors, Justin was a cross dresser. Until he had met Craig online, the only people that suspected his fetish had been those cashiers. Now another man knew, and had confessed to sharing the fetish. After speaking for months, the two men were going to meet for the first time.

Shifting the car into reverse, Justin looked over his shoulder and backed out of his driveway. The street was illuminated with yellow light, giving it an eerie and almost supernatural feel. In his chest his heart seemed to be pounding, the thub-thub sound of it drowning out the radio. Justin tried to calm himself, but his excitement was too great. In just a few minutes he would be meeting Craig for the first time.

The hotel was easy enough to find. Since planning the meeting, Justin had driven past the building multiple times, pausing in front of it before speeding away again. This event had been played out in his mind a million times before, just the idea of it springing an erection. Though he had been excited by it, his arousal hadn’t been satisfied by his wife. Amy had noted his unusual amount of masturbation, pointing it out to him and teasing him about it. Justin had been embarrassed and ashamed, and since her comment had only taken care of himself when she wasn’t around. He didn’t want her to suspect anything.

Pulling into a parking space, Justin slipped out of the car. Grabbing his backpack, he took a long, deep breath, filling his lungs with air before exhaling and slamming the car door with a metallic bang. Hoisting the bag over his shoulder again, he walked casually towards the lobby doors.

The girl at the front desk smiled friendlily at him as he walked in. Justin looked ahead nervously, avoiding eye contact with the girl. Did she suspect anything? Did she know? He quickened his step and walked towards the hallway, relieved to be out of the lobby and away from her prying eyes.

Craig had emailed Justin from his laptop an hour ago. He was in room three sixty six, on the third floor. Walking past the elevator, Justin turned in the stairway. Very nervous and scared, he thought that the bit of exercise would make him a little more comfortable when he finally met Craig.

Taking each step slowly, Justin climbed up the stairs. His mind was spinning, his heart beating heavily in his chest. Breaths came in deep gasps, a combination of the climbing and the excitement he felt. Step after step he ascended, coming closer and closer to the doorway he would pass through, shifting his life forever. It seemed as though only moments had passed from the time he had taken the first step to the moment he reached the third floor, the door wide open in front of him. Body shivering with excitement, he passed through the doorway and started down the hall towards Craig’s room.

The golden numbers on the door showed Justin a distorted reflection of himself. Standing up straight, Justin pushed his shaggy blonde hair away from his face, up over his head and prepared his hand to knock. Tapping on the door lightly, he shook with anticipation. Any second now the door would open.

The knob turned, startling Justin. He gasped and struggled not to jump back or run away. He was excited but also frightened by what he would find on the other side of those golden numbers. He had seen pictures of a young man, slightly older than himself, in his mid thirties, with dark hair and dark eyes, but what could a picture really tell you about a person? Craig could be anyone, and Justin was about to be face to face with a stranger.

As if in slow motion, the door opened. Two dark brown eyes met Justin’s blue ones, a smiling face looking straight into his own.

“Justin,” Craig said, holding the door open. “Come on in.”

Unable to speak, almost as if his voice had been taken away from him, Justin gulped. Nodding, he slipped past Craig and into the dim room. The lamps were on, but the light wasn’t much. He took a few steps into the room and turned around.

Craig slowly slipped the “do not disturb” sign onto the doorknob, shutting the door behind him and clicking the deadbolt into place. Turning around, he smiled at Justin again, his thick lips curling upwards in a teasing way.

“I was afraid you wouldn’t come,” Craig said, his deep voice reverberating off the walls. The voice seemed to penetrate Justin’s body, making his very bones shake as he quivered.

Straightening up again, Justin tried to hide the fear he felt. Shaking his head, his shaggy hair falling back in front of his eyes, Justin tried to respond to Craig’s comment but again found his voice had abandoned him. “I’m glad you’re here, anyway,” Craig said, walking away from the door and towards Justin. Justin knew that Craig had experienced meetings like this before. They had discussed it in length on the telephone, what things Justin was willing to try and what things Craig hoped they could do. But now that he was here, Justin felt doubt entering his mind.

Craig moved past Justin, keeping the space between them rather wide, and took a seat on the bed. Justin turned, watching Craig’s slim body as he moved. Craig wore black shorts that fell lower than thigh length, and a loose top. Justin couldn’t make out much of his body underneath the loose fitting clothing, but he thought that Craig’s face was attractive enough. Full, thick lips, easily curling into a smile, and almond shaped brown eyes with thick lashes. Swallowing again, Justin thought to himself that Amy would find this man attractive. Craig’s exposed lower legs were covered in dark hair, and his calf muscles stood out well.

“Justin?” Craig said, softly, looking up from the bed to his blonde companion. “Aren’t you going to say anything?”

“Hi,” Justin said, his voice cracking. Justin’s cheeks instantly flooded with color, his quivering voice embarrassing him. He looked away from Craig’s laughing face as the other man chuckled.

“It’s understandable that you’re nervous,” Craig said, lying down on the bed. He crossed his legs and put his folded arms under his head, propping his face up to watch Justin as Justin began to nervously pace the room. “I don’t expect you to just jump in bed with me, you know.”

“I know,” Justin said quietly, putting his hand over his face. He wiped the sweat away from his brow and pushed the hair out of his eyes again. His heart was beating so loudly he thought for sure that Craig could hear it. Taking a deep breath, he opened his eyes and looked back down at the man on the bed. “I’m sorry,” he apologized.

Craig laughed again, further embarrassing Justin.

“Hey,” Craig said. “There’s nothing to be sorry for. Let’s try to think of some things that could relax you, huh? Do you want a massage?” Craig patted the bed next to him, suggesting that Justin lay down next to him.

“I don’t know,” Justin said. “I’m sorry,” he apologized again.

“Stop apologizing,” Craig chided. “Come on, lay down. Take off your shirt. I brought some oil in case you were tense.”

Rolling over, Craig got off the bed, and Justin reluctantly pulled his shirt off of his chest. His tanned skin was exposed to the other man for the first time, tiny golden hairs covering the darkened skin, his tight stomach flexing as his arms pulled the shirt off and tossed it to the side.

Slowly, Justin kicked off his shoes, walking over to the bed in only his socks and pants. He climbed up on it, crawling to the center and lying his body down slowly.

“Good boy,” Craig laughed, pulling a bottle of oil from a bag next to the bed. “Now, shut your eyes. This is going to feel good, I promise.”

Justin rested his head in his folded arms, struggling to relax his body. The first touch of Craig’s hands on his body almost made him jump in surprise, and he had to laugh at himself as he closed his eyes lightly.

The bed moved as Craig hoisted himself onto it, straddling Justin’s back. Justin’s skin tingled at the feel of the shorts against his bare skin, the rough fabric sending sensations through his body. The feel of Craig’s weight on his body made him feel good, and he couldn’t help sighing into his crossed arms as Craig opened the bottle of oil.

Wet, slick noises filled his ears as Craig rubbed the massage oil into his own palms, warming it before he reached down to knead Justin’s shoulders. Craig’s fingers pressed into the muscles between Justin’s shoulders and neck, rubbing persistently but gently, almost forcing Justin to relax. His slick fingers rubbed into the muscles, working out the knots slowly, as Justin groaned with the pleasure of the rubbing. It had been a long time since anyone had rubbed Justin’s shoulders, and he was enjoying it.

Slowly, Craig moved down from Justin’s shoulders to his back, his fingers sliding their way across Justin’s smooth, tanned skin. The tips of Craig’s fingers pushed into Justin’s muscles, pushing the flesh this way and that as he ran his fingers in circular motions, working out the soreness. Everywhere his fingers touched, a good, aching pain arose as the tension melted away. Soon Justin was moaning as Craig’s hands worked their magic, and he felt completely relaxed.

Craig smiled, looking at the shiny skin underneath his hands. The lamplight reflected off the dark oiled skin, his palms moving over Justin’s back. The heavy massaging stopped, and Craig was just enjoying the feel of the muscles underneath his hands. Justin was enjoying it too, and moaned into his arms again, arching his back slightly and pushing his bottom up into the air. Reluctantly, Craig moved his hands away.

Remaining on top of Justin’s back, his thighs still rubbing against Justin’s skin, Craig spoke again.

“Do you feel better,” he asked.

Justin moaned again, nodding his head in his arms.

“Glad to hear it,” Craig said. “Do you feel comfortable enough to show me what you brought?”

Justin sucked in a deep breath, his heart speeding up inside his chest again. Almost reluctantly, he nodded into his arms. Craig smiled and moved off Justin’s body, the bed shaking as he rolled off Justin and sat on the edge. Justin slowly pushed himself up, his blonde hair ruffled where it had rubbed against his arms. He looked almost like a little boy as he walked over to the bag.

With quivering fingers Justin unzipped his bag, opening it and pulling out a few of the items. He blushed as he saw the lingerie, items that no one had ever seen him wear. Slowly, he turned around, holding up a pair of red panties so that Craig could see them.

“Very nice,” Craig said, his smile widening. Craig’s eyes sparkled as he looked from Justin to the panties. “I’ll bet the color looks fabulous on you.”

Justin blushed, half happy that the other man liked the panties, half horrified that he was actually showing the clothes to someone else. Putting the thong panties aside, he pulled out the matching garter and fish net stockings, lifting them up almost casually for Craig’s inspection.

“Justin,” Craig said, seriously. “I can not wait to see you in these.”

Justin’s eyes darted from the floor to the other man, his gaze slowly locking on Craig’s crotch. The loose shorts didn’t give much away, but Justin imagined that he could see a bulge in the other man’s pants. Swallowing deeply, Justin looked back at the backpack. He lifted out a lacey corset, one that didn’t lace up very tight. He loved the feel of the corset against his chest.

“Are you going to put them on?” Craig asked, eagerly. Justin seemed unable to look away from the corset. Slowly, nervously, he nodded. His pounding heart thumped inside his chest as he gathered the items and his backpack into his arms.

“It’ll just be a moment,” he whispered, walking towards the bedroom.

“Take all the time you need to make yourself pretty,” Craig smiled, watching Justin as he nervously made his way into the bathroom.
Shutting the door, Justin considered flipping the lock. But that was just silly, he thought to himself. And it might insult Craig. So, leaving the door unlocked, Justin began to strip out of his pants and socks.

Carefully, Justin slipped the panties over his legs and up his thighs, relishing the feel of the smooth fabric against his sensitive skin. The thong slipped between his buttocks, rubbing against his sensitive hole and making him shiver with excitement. The feeling was always the same when he put the panties on, his cock instantly beginning to swell, pushing against the red fabric which held the bulge snugly against his body.

Justin took another deep breath, pulling the garter belt out of the bag. Fastening it around his tight stomach, he sighed deeply, looking at himself in the mirror. He loved the way he looked like this, the straps dangling loosely against his legs, the red panties bulging with his semi-erection. Slowly, deliberately, he began to step into the stockings, sliding them up his rough legs. His hair stuck out of the crisscrossed openings, but that only mildly upset him. One of his fantasies was to shave his legs smooth, to make them more touchable. But that would have given his wife some idea of what was going on, and Justin didn’t know how to hide shaved legs from someone he regularly snuggled up against in bed. Shaking his head, Justin tried to ignore the hairs, and clipped the stockings to the dangling garter.

The corset slid on next, the thick fabric wrapping around his chest but leaving his dark nipples exposed over the top. With some difficulty, he hooked the back into place. The smooth fabric felt good against his recently massaged skin, and Justin looked at himself in the mirror. The corset added a bit of curviness to his figure, squeezing his stomach slightly to give the illusion of hips on his male body. Justin slid his hands down his sides, reveling in the feel of the pressure against his ribs. Taking another deep breath, struggling not to bend too much, he pulled a pair of black high heels out of the bag.

Slipping his feet into the pumps, Justin felt his calves tensing. His legs were forced into a strange position, familiar to him only because he had tried the shoes on before. It was still a bit difficult to stand with most of his weight on his toes, but Justin struggled to do so gracefully. With his hands he combed his hair out of his face again, and leaned towards the mirror, examining his features.

Over the last couple months he had been experimenting with some of his wife’s makeup. He wasn’t totally comfortable with it yet, but he loved the feel of it on his face. It was almost like a mask on him, a cover over his natural skin, transforming him from the Justin his wife and friends knew to the Justin that was in a hotel room meeting a strange man for perverted activities. Pulling some of the makeup out of the bag, Justin began to paint his face.

The blush added a nice tone of color to his cheeks, but with the embarrassment he’d been feeling all night it really wasn’t necessary. Still, the feel and scent of the rouge made him feel good, so he brushed it on sparingly. Bright red lipstick was next. The cool, thick coats of red over his full lips made him feel sexy. Puckering at his reflection, he smiled. The dark red matched the color of his panties, stockings, and corset. Lastly he pulled out the mascara and darkened his long lashes, batting them once or twice once they were done.

The finished product was quite stunning, his handsome face transformed into something more feminine. Justin’s tongue darted out of his mouth, tasting the sharp taste of the lipstick on his lips. A shiver traveled up his spine, and Justin was ready to leave the bathroom, exposing himself to another human for the first time.

His hand shook as he twisted the knob on the doorway, and his chest heaved as he breathed heavily, lifting one foot and taking a step off the linoleum and on to the carpeted floor of the hotel room.

Craig was still sitting on the bed. His legs were crossed in front of him, his body resting back against his arms. When Justin came into view, Craig sat straight up, his arms at his side on the bed, and looked the other man up and down. Blushing again, Justin watched Craig’s eyes drift up and down his scantily clad body. Justin suddenly felt silly, and the urge to cover himself with his hands flowed through his body. But as he lifted his palms, Craig shook his head softly, looking Justin in the eyes.

“You look great,” he said softly, standing up. “Gorgeous, even.” Craig walked slowly towards Justin. Justin felt as though he were locked in place, unable to move an inch. His feet, in the high heels, ached slightly. His chest heaved under the corset, his bare shoulders pushing his chest out.

“Thank you,” Justin said, his voice barely above a whisper. “It’s exciting to have someone see me like this.”

“No one has before,” Craig commented, almost to himself. “I can’t believe you’ve been hiding it for so long when you look so great.”

Justin laughed suddenly, his nerves a little more at ease as each second went by. His heart still thumped quickly in his chest, the sound of blood pumping filling his ears. Craig was hardly a foot away from him now, their bodies becoming closer and closer as Craig took tiny steps. Sucking in a breath, Justin moved, closing the gap between them. His bare nipples brushed softly against Craig’s shirt, hardening instantly at the friction.

Slowly, Craig moved his head forward, his nostrils flaring as he smelled the makeup on Justin’s face. His lips were close to Justin’s lips, the full red lips of the other man parting slightly. Craig moved even closer and brushed his lips against Justin’s, tasting the lipstick as he did.

Justin’s lips spread further apart, his tongue tasting his own lipstick, and the musky taste of the other man’s mouth. Craig allowed Justin to explore, Justin’s tongue first licking the underside of his lips and then moving over the round edges of Craig’s teeth.

Moaning, Justin plunged his tongue in deeper, running it along the ridge at the top of Craig’s mouth, tracing the line and then touching Craig’s tongue with his own. Their breaths mingled together, each tasting the other as their kiss went on.

Lifting his arms, Craig wrapped himself around Justin’s muscular body. The corset didn’t cover much of Justin’s back, and Craig could feel the hot skin, still slick from the oil he had used in the massage not long ago. His fingers dug into Justin’s flesh, pulling Justin’s body closer to his own, Justin’s chest thrusting hard against Craig’s shirt. The bulge, confined by the dark red panties, pushed up against Craig’s leg, and Craig smiled, his lips curling up away from Justin’s. Justin moaned into Craig’s mouth again, thrusting his hips against Craig’s leg, his hot breath filling the other man’s mouth. Justin yearned for the feel of Craig’s bare chest against his.

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