Chapter Text
— Recap —
Breathless and panting, the two men continued to lock lips as their hands began to explore each other's bodies, taking off articles of clothes whenever possible. Soon they stood in Neal’s living room in only their underwear, lips still clinging to one another. Massimo finally made the move to break away from the kiss, observing a very reluctant Neal.
Backing up from Neal and finally no longer cornering him to a table Massimo motioned to the bed not too far away. “Round 2?”
——————
Neal contemplated his options. Neither were good. Option one: lower the mafia head to the bed, have him strip, and then try to slip out with June which he’s busy scrambling to get his clothes back on. The chances that Massimo would resort to chasing him naked were slim. Risk: retaliation. It was clear that Massimo had both the finances and power to easily find him when this was over and given the way the system tends to work, he would succeed. Option two: go through with the night and pray for the best. Risk: going through with the night. Finally, as there is always ‘another’ way, we had option three: talk this out like adults, see what Massimo wants, and improvise a way to talk himself out of it. Personally, Neal was a fan of option three. But something about the way the evening had progressed and seeing the half undressed muscular man before him who was oh so very good at kissing made him lean towards option two. Taking a sip from one of the wine glasses behind him, Neal raised a glass to new experiences.
“I’m new to this,” Neal admitted hesitantly as he placed the wine glass back on the table and began to advance towards Massimo. “And not a fan of uninvited guests treating my place as their own.”
Massimo watched with snake eyes as Neal waltzed towards him. Seeing the younger man, clothes disheveled, hair ruffled, and with a bright flush on his pale cheeks was quite a sight to behold. An irresistible sight. “You give me too much credit if you assume I’m well versed. And I was asking. Not making a statement.”
Reaching the mafia head and leaning his face close, Neal whispered into Massimo’s ear, “Sounded like a command to me.”
The older man immediately reciprocated by gently grasping Neal by the neck and pushing his head back, angling it in the process to look up at him. “You like that?”
“Exploring,” Neal replied.
“Lie down on the bed,” Massimo growled. “That’s a command.”
Neal, without realizing it, obeyed. Everything about this situation was deadly. Yet everything about this situation was also unbearably sexy. The con man felt a similar rush of adrenaline in this moment as was common in the minutes before he pulled a heist. A mixture of excitement and fervor with a dash of the fear that everything might go wrong.
For a brief second, Neal lay on top of his sheets alone, glancing up at the older man as he admired the view. In the blink of an eye, Massimo climbed onto the bed and positioned himself on top of Neal, legs straddling the younger man’s torso and arms supporting his weight on either side of Neal’s head. Good thing Neal did not go with option one – he probably wouldn’t have even made it out the door.
“Didn’t expect you to be so… accommodating,” Massimo breathed into Neal before locking lips in a passionate kiss once more, shifting his weight onto his right hand so that his left could explore the younger man’s body once more.
At that comment, Neal decided to play with fire and clamped down on Massimo’s lower lip, intentionally drawing blood. “My accommodation does not come for free.”
“Yeah,” Massimo purred, satisfied at how the con man always did the unexpected.
Licking the blood off his lips, Massimo decided to begin the trek down to Neal’s groin, leaving kisses and the occasional mark on his way there. During all this, the mafia never broke eye contact, keeping Neal’s every reaction in sight and embedding it into his memory. As Massimo approached Neal’s quickly swelling cock, Neal let out an unsuppressed moan that brought a satisfied smile to the mafia boss's face. But it also made Massimo want to tease the young con man more. Before making contact with Neal’s crotch, he used his tongue to trace his path past the con man’s abs, through his defined chest, up his redding neck, and back to his lips.
The eye contact throughout this possession was killing Neal as his cock wanted to break free from its fabric restraints. It was a new experience for the both of them – new, pleasure experience to clarify. Neal was always romantic and something about seeing your partner inch down towards your crotch got him excited in a way that couldn’t be expressed with words. On Massimo’s end, Neal’s reactions got his cock also trying to break free. Both men had had a number of partners throughout the years, but something about this experience in particular aroused both men in a new way.
Before Neal is able to reflect long on these thoughts, Massimo again began his journey downstairs and this time, his hands were helping out. Supporting Neal with his right arm on his lower wait, Massimo slowly slid off Neal’s underwear, exposing his bare nether regions. Seeing how happy Neal was to see him, Massimo chuckled with satisfaction – slowly sliding off his own underwear as well.
A warm and wet mouth soon wrapped itself around Neal’s cock as Massimo went down on him. The intense sensations of the event, coupled with the sensitivity of the appendage, caused Neal to push his head back into the pillows as he let out an intense and sensual moan. It may be Massimo’s first time with a cock in his mouth, but he was not a stranger to receiving them. Using the techniques often used on him in previous nights, Massimo quickly got Neal close. Feeling himself there, Neal tried to push Massimo’s head away to prevent from accidentally releasing it into the older man’s mouth or onto his face.
“No,” Massimo growled, his mouth full and gripping both Neal’s arms at the wrist with his left hand and pushing them away, “let it out.”
“I can’t-” before Neal could finish, he finished inside the mob boss's mouth, releasing a thick white liquid and feeling his cock pulse at the pleasure. Looking down, Neal saw the older man continue to stare at him as he gulped down his cum. This sent shivers down Neal’s back that could only be categorized as an unrealized sexual desire for the man before him.
For Massimo, it was a new experience indeed to not only give a man head but also to have cum in his mouth. Surprisingly, he did not mind it. Seeing the sounds and expressions Neal made during the process was more than enough payment for the service he provided. Noticing the way Neal glanced at him after cumming in his mouth, Massimo could not resist the urge to swallow the release to see how Neal would react. And it was completely worth it.
Letting the remaining cum and saliva drip from his mouth into his hands, Massimo began to stroke his own cock with his left hand as he advanced towards Neal’s ass with his right hand. Massimo now knelt between Neal’s parted legs and inspected the younger man’s hole to see how this would go. Most women would be wet by now and after a finger or two or three of foreplay, would be ready for penetration. Unsurprisingly, an asshole would not have that automatic function. Licking the pointer finger of his right hand, Massimo gently circled outside the hole, gauging Neal’s reactions to it. It was primarily of confusion and fear at the new experience – but no reluctance. Slowly, Massimo attempted to push the finger in but stopped quickly as he heard Neal hiss at the entrance.
“You okay?” Massimo asked.
“Yeah. Yeah,” Neal replied through closed eyes. “Don’t worry, I’m okay.”
Seeing the clear pain on Neal’s face along with how strongly he had shut his eyes, Massimo let out a sigh and changed his position such that he was not on top of Neal once more. Hearing the movement, the con man opened his eyes to look at Massimo with confusion.
“Don’t lie to me Neal,” came the answer.
“I’m sorry,” Neal stammered. “Let me suck you off instead?”
Shifting in his position, Neal attempted to sit up to gain better access to the older man’s cock which he was still stroking with his left hand. Before the con man could make it very far, a calloused hand pushed him back down onto the mattress.
“Stay,” Massimo ordered. “And moan for me baby.”
The mafia boss then moved in for a kiss and used his tongue to explore the innermost depths of the younger man’s mouth. After a considerable amount of exploration that left Neal breathless and seeing stars, Massimo laid a trail of kisses down his cheek and to his neck. There, the mafia boss strategically allowed his teeth to graze such a sensitive area of the younger man’s body, eliciting a sharp gasp. At this, Massimo growled his approval before beginning to at first gently, and then with more force, suck on an area right above Neal’s collar bone. An area where a hickey would be both easy to hide and easy to find.
Typically Massimo wasn’t one to leave marks. It was a lot of effort for something that didn’t give him direct pleasure and it wasn’t something he would actually see (as a rule of thumb he never slept with the same woman twice in one month). But seeing how Neal reacted to them and how perfectly those red blossoms looked on the con man allowed Massimo to understand for the first time why people would ever go through the effort. Appreciating the art he left on the younger man and hearing the symphony of moans coming from his mouth brought Massimo close to finishing. Feeling himself on the edge, Massimo moved back up to bring Neal into a deep kiss, pressing his body onto the younger man’s and feeling the heat between them. Finally climaxing, Massimo released his load over Neal’s stomach and, sitting up to appreciate the view, could feel himself quickly start to get aroused again.
Massimo laid down beside Neal on his back, eyes closed, living in the moment and still feeling the heat between them. Neal turned to look at Massimo with a perplexed look on his face.
“Ask me,” Massimo said, eyes still closed.
“Are you sure you don’t want to fuck?”
Turning to lay on his side and look into the con man’s sky blue eyes Massimo couldn’t help but smile. This, lying in bed with a man who conned him out of an art piece worth millions, was not something he would have ever expected doing. Taking out the latter part of the situation, lying in bed with a man was something Massimo did not think would happen. Yet here he was. And he was… happy.
“Yes.”
“As in yes you would like to fuck but you can’t because your a one shot man?” Neal knew exactly what the mafia head meant but something about the moment made him want to tease the older man. At this point of the night, the fear he once felt towards the dangerous mob boss had, for the most part, dissipated.
“Yes I would like to fuck but,” looking at Neal, “another day.”
Neal was surprised at the honest response. “Aren’t you supposed to be a villain?”
“Even villains have a soft side.”
“Mmm hmm,” sliding his knee between Massimo’s legs to gently tap at his rising erection, “except you're hard right now.”