*Four Months Ago*


Justin watched as a man dressed in a 20’s gangster costume with a simple black mask covering his face drift through the mass of people on the dance floor at UpSt8, the new and hottest club in the theatre district. 

Justin was quite certain that on any other night, the door attendant would not let him in, of course, he had never tried, but he was sure he was not fabulous enough. However, tonight, tonight he was one of the beautiful and fabulous. He was attending the party for GRIMS’ 200th show at its’ very own theatre, and the entire cast was invited to attend the masquerade. 

Justin had received two tickets, he invited his best friend Daphne, but she had cancelled at the last minute, leaving him dressed in drag alone and ultimately finding out that none of the other ‘fairy’ actors had shown up. Most of them were prudish and despised the party scene. Justin however, found it intoxicating and alluring. He only wished he were not stuck up against a wall drinking expensive wine alone.

Justin continued to watch the crowd, fading into the background, as he assumed how it would always be, smiling at the costumed elite through the large black feathery mask that matched his feathery-fringy flapper girl dress. The music ranging between techno and blues blared around; both were an equally intense soundtrack for the eccentric people packed in for the party. 

About an hour and six glasses of free wine later, Justin decided to leave the comfort of wall flowering and ventured into the masses of people. Hoping to possibly spot the masked gagster. Wearing a mask himself, somehow gave him more pride. 

After ten minutes of milling about Justin decided, he had been better off in the corner. He was not the only man that had opted to dress in drag; however, he was the only one that most had thought was actually a woman. Many men began to proposition Justin. Justin prided himself on his excellent gaydar and found himself out-right laughing at the straight men for their confusion. This turned into quite the sight and he nearly had to whip his dick out to prove he was a male. 

Another hour and two more glasses of wine and Justin was dancing and giggling with a semi-cute, and thankfully gay, waiter. “Are you one of the actors in Grim?” The tall, muscular, black haired man asked with adoration then pulled Justin closer to him.

“Mmmhmm.” Justin answered and giggled when he felt the man’s hard-on press into his groin. He liked the attention.

“So, who do you play, a woman? Cause you’re really hot all dressed up like that.” The waiter grinded himself into Justin once again and held tightly, perhaps to tightly to the actors hips.

Freightened a bit, Justin excused himself and went to search for the bathroom. He opted to use the ladies, not wanting to deal with the image of peeing in a urinal with a skirt on, and there was the pulling down of the fish net stockings to consider, so he relieved him self along side a few real women, most dressed in whorish costume. 

He washed his hands, touched up his lipstick, and stared in the mirror at a face that was nearly unrecognizable. “Well, Tina.” He spoke when he was alone in the tiled room. “You out did yourself tonight.” Justin pushed back the short wisps of blond curls and resigned himself to going home. He was far too inebriated to continue the night.

“I was watching you.” Justin had just walked outside the club and was startled by the scratchy voice. 

He turned and saw the masked gangster leaning up against a lamp post smoking a cigarette. Justin could not help his sunshine smile displaying itself for the mysterious man before him. “You know normally I would turn and run if someone said that to me, but somehow, that coming out of Al Capone’s mouth makes me feel special.” Justin’s blue eyes mischievously sparkled.

Masked Gangster laughed. “I prefer to think of myself more along the lines of Dick Tracy.” He flicked his cigarette and approached the blond ‘girl’.

“Didn’t Dick Tracy wear some kind of yellow suit?” Justin asked confused.

“Fuck if I know.” The dark man said with a smile. “I was just referring to his sex appeal.” This made them both laugh.

Justin pulled his, or rather Daphne’s shall closer to him. Autumn nights in New York were rather chilly, and Justin was not used to there being such a large breeze up him.

“So, do you want to stand here all night and freeze to death or do you want to come back to my hotel for a night cap.” Lust dripped from the last two words.

Justin wanted the man the minute he had seen him, but he really was not sure what that meant. He was a twenty-one year old virgin. He’d read all about gay sex, but seeing as though his only friend was a straight girl, he didn’t have much to go on besides the books and the little porn he had seen. 

Justin was blushing furiously. Women often and men had propositioned him but never before had he actually wanted to go with them. Looking at the masked god before him, he just nodded his head yes, there was no way he could say no. 

The Masked Gangster took the flapper girl’s hand and started to walk across the nearly deserted street having to support the, what he thought was an only slightly buzzed, ‘girl’ who was giggling with him.

“So, what’s your name?” Justin asked, reveling in the closeness of the taller, older man. 

The man peered at him from under his black hat and through his mask hesitating to long. “How about we continue the theme of tonight?” He said.

Justin looked confused. “Well, I don’t know about you, but, I am no Bonnie, I don’t rob banks, hell, I’ve never even held a gun before.” Justin started to ramble. “I try not to live too dangerously.”

The man laughed again, a sound that Justin liked and went straight to his cock. “So, you think walking in the dark New York streets with a masked stranger is safe? is this something you do often?”

“Oh, no you see, I don’t….I..uh..I mean.” The stranger nearly slamming his lips against his strawberry flavored glossy ones cut off Justin’s words making him forget all about robbing banks, danger and names.

Minutes later, they were in the elevator of the Stratford. Justin watched as his stranger pressed the button indicating the top floor penthouse. He had to hold back from saying ‘wow’ and showing how excited he was. He snuggled against the lean man awaiting and scared out of his mind of what he new was going to happen next.

The elevator dinged and soon they stood inside the living area of a lavish suite. The booked hotel room probably meant that the man was one of the out-of-town and rich financial backers of ‘Grim’. Whoever he was, HE was taking off his clothes and soon stood naked in front of the boy in drag.

Justin’s heart felt like it was choking him to death. His dick was painfully hard being squeezed within the tight material of the hose. He was unsure of what to do. ‘Do I take off my clothes?’ He wondered. Then a thought swept through him, ‘I know he’s gay but does he know I really am a boy?’ 

Justin’s question was answered as the naked, except for the black mask, man reached under the front of his dress and gently cupped his penis. “Aww God!” Justin gasped.

“You are so fucking hot little boy.” The stranger whispered into Justin’s seashell ear, making the boy swoon. “I’m going to undress you but we’re going to leave our masks on. It’ll make it hotter.”

Justin could only nod in agreement. The former gangster took that as permission to do, as he liked, so without further ado he unzipped the back of the black dress. Slowly he peeled the tight material down the boy’s body until it pooled to the carpet and Justin steeped out of it. “Fuck you’re beautiful.” The scratchy voice sent chills up and down Justin’s body as he fought to control himself.

The next thing to go was the heels and fishnets. Then Justin stood in only a pair of tightly whitey’s and the black feathery mask. Yes, he was all male, there was no mistaking that. He did not realize that the other man had to catch his breath at the captivating site. “I…AM….GOING…..TO…..FUCK….YOU!” Justin heard growled at him. This made his penis leak and become so unbelievably hard it began to peak out of the waistband of his underwear.

This did not go unnoticed by the stranger, all he could do was tear the boy’s underpants from his body and dive down to taste the beautiful dick and its’ leaking pre-cum. 

The blonde boy had never felt such wonderful sensations. His body was on fire with a heat he was sure was inhuman. “Oh, god!” Justin moaned over and over.

The masked man sucked greedily at the head for a few moments and then took Justin’s pink thick dick deep into his throat. He had to grab the back of the boy’s thighs to help him keep standing, finding the affect he had on the blonde, and vice-versa, exhilarating. It was only a few seconds and he could feel the boy’s soft balls drawing up and nearing his climax.

That is when he decided to slip his hands up from the light golden haired thighs to the firm round globes of Justin’s ass. He massaged the wonderfully soft cheeks in his hands for only a second, then slipped one finger inside them, and lightly rubbed up against the silky pucker. He had just enough time to pull Justin’s dick from his throat and rest it on his tongue as stream after stream of sweet cup erupted into his mouth and down his throat. It took him a minute to realize he had come all over his own belly and leg. The boy was that beautiful and intoxicating.

Justin kneeled down to the masked man’s level and stared at him for a moment. Both of their breathing was ragged and as they fought for air they seemed to only want to breathe in one another. He wanted to draw him so badly. Sketching and Painting was just one of Justin’s hobbies, but he was quite good and ached to draw the man that had given him more pleasure than he ever knew was possible to exist. Now was not the time, his soon to be lover was leading him down a hallway and into the large master suite bedroom.

Justin stared at the bed and felt his heart start to pound wildly once again. ‘This is it!’ He thought. ‘Am I ready for this?’ He saw the smile that played on the black masked man before him, it made his heart lurch and he knew the answer. ‘Yes.’

Justin soon felt his body lifted onto, what he was sure was, Egyptian cotton red sheets. He smiled up at the man who brought himself down slowly over his small framed body. He felt the sticky cum gluing some of their skin together, as well as the rock hard cock of the man who was about to take his virginity. He felt a shock of fear jolt him and he stared worriedly into the man’s dark brown eyes. 

The naked gangster noticed the boys fear and soothed him by kissing his eyelids and then following with slow languorous kisses to his lips. When he pushed his tongue inside he traced the pearly white teeth with it and was pleasantly surprised when Justin started to suck the taste of his own cum from his tongue. This was making him impossibly hard and had him moaning, acting once again like a school- boy and forcing him to demand harder rougher kisses.

Justin started to grind his hips and now aching cock against his lover. “Please, Please, Please.” Justin begged, not really knowing what he was begging for. 

“You want me to fuck you little boy?” The older man asked in a whisper. “Did you like all the attention those men gave you when you thought you had a pussy?” He continued. 

Justin could not answer. He was so far gone from the feel of the hot wet tongue circling his nipples, sucking them, and then nibbling . Justin loved the way the silky material of the gangster mask rubbed against his skin cooling the places where the man had bitten him.

“Please, please fuck me now!” Justin begged once again as he felt the mans tongue dip into his tight pucker.

The masked man looked up at the boy and smiled wickedly. “You like that.” He whispered and continued his exploration making the young body thrash upon his hotel bed. When he added a spit soaked finger the boy gasped. The orifice was so tight and it took a while to get his pointer finger all the way in. He moved the finger around and continued the assault, adding two more spit drenched fingers and scissoring them aoart amongst the tender walls. He couldn‘t get over how tight the kid was. He enjoyed the taste of the boy, it was so sweet and….and…and… virginal.” But he had been so eager? He stopped his torture and looked up at the blond who was not happy about the loss of action and then was seemingly embarrassed by the uncontrolled whimper that escaped his sweet pouty mouth. 

“Have you ever been with anyone before?” The older man said looking into Justin’s eyes for the truth.

Justin wished he could crawl in a hole and die. His feathery mask hid nothing and the red sheets surrounding him only emphasized the blush that spread among his body. “No.”

Justin was sure that the other man would yell at him and tell him to get out but instead he saw a slight smile grace the raspberry colored lips and felt them lay a kiss at his now semi-opened hole.

Justin watched as the man placed a condom on his long cock and he contemplated how it was going to fit inside him, but he new he had to do it. He wanted the man as much as it seemed the man wanted him.

His small legs were placed on the man’s strong muscled shoulders. Justin watched in wonder as lube was spread over the massive cock and then into his hole making him shivver with anticipation.

“It’s gonna hurt.” The man told him. “But I promise it will get much better, just relax and push into me. You’ll be alright.” 

Justin nodded his head and the man kissed him tenderly. Not another word was spoken from their mouths yet so many lines were written with their bodies.

They ‘made love’, as Justin liked to think of it, too many times to count that night. When Justin awoke to an empty bed he was not surprised. He walked into the living area and found a note written on hotel paper beside his drag clothes, along with a pair of sweats and a t-shirt. With shaky hands he picked it up trying not to cry from the dread.

Blondie,
Had a great time last night, but as all good things do, this must come to an end. I hope I gave you a night you’ll never forget. I won’t forget it. But now it’s time to take our masks off and go back to reality. This room is paid up until tomorrow so stay as long as you like. The clothes will be a little big but I’m sure you’d rather go home wearing that than the other thing you had on last night. I won’t be seeing you again, but, you can see me in your dreams.- Al Capone

Justin folded up the letter. He willed himself to not cry but lost the battle as he dressed himself in the clothes of the man he loved, clothes that smelled like him and walked out of the Penthouse suite rented by a man whose name he didn’t know, a man who he was sure he would never see again for the rest of his life, yet, he would love as long.