Breaking Free [M/M] (closed for garajd)

Simon, obviously enjoying this more and more by the moment, took his sweet time sliding down his briefs for the pleasure of both men, and watching Charles harden as he bared himself bit by bit was intoxicating. He showed off a little, turning slowly and running his hands over himself, cupping his genitals and flicking his thumbs against his aroused nipples.

"Do I please you, sir?" he asked Charles, licking his lips. "My father taught me to be an obedient and well-behaved young gentleman... but Mr. Dalton's been my most significant mentor. I should warn you, sir, I'm soooo ready to cum... just a breath on my hard cock could make me explode."

Allen looked over at Charles, "I know as well as you do that you are dying to swallow his young cock and his incredible 2-day load."

Charles fell all over himself getting to his knees. "Thank you, Allen. You do know me quite well. I am honored by your gift of this young cock and his load."

Kneeling in front of Simon, Charles slid a hand up Simon's thigh and cupped his full ball sac, an immediate reaction from Simon at Charles' delicate caress. Charles knew that Simon was indeed ready to erupt, so, no more playing now. Charles leaned forward, mouth open wide, and swallowed Simon's shaft in one motion . . . flicking his tongue out on Simon's balls when he felt the cock head probe his throat.

"Simon, feel free to wrap your hands around Charles' head; he does enjoy a hard cock in his throat and will attempt to swallow every drop of your offering."

Allen stood silently by, stroking his cock, enjoying the interaction between Charles and the young slut . . . who will be the first to take his virgin pussy?

Simon trembled with excitement when Charles was invited to swallow his cock. He moaned when the man touched and caressed him, his cock twitching and oozing forth a dribble of precum. Being touched like this by an older man was heavenly, and he felt he was truly finding his purpose. He was in awe of the expression on Charles' face, and the sensation of his warm mouth and tongue. His fingers combed through the older man's hair and cradled his head, inviting him close in what was like mutual worship.

"Ohh, yes sir... that's so... ohhh...."

Charles was clearly an excellent cocksucker, but regardless, Simon was more than ready to release his backed-up load. He tried to draw it out a little, but it was a losing battle. His thighs quivered as the unstoppable rush overtook him. His hips bucked hard, slamming his cock against the back of Charles' throat as he released a loud yell of ecstasy, his eyes cutting from Charles' face to Mr. Dalton's stroking. What felt like a year's worth of stored cum gushed out of him in rapid-fire spurts, and he held Charles' head even tighter now, if nothing else than to help him keep his balance as his body was rocked with the force of his orgasm.

Allen stood where he was, enjoying the erotic display in front of him; he would love sharing this with Marilyn tonight in bed, anticipating the blow job he would get from her. As Simon's spasms came to a slower pace, and ultimately stopped, Allen was amazed at Charles' ability to swallow almost all of Simon's explosive cum, barely a dribble running down his chin.

Handing Charles a towel to wipe his chin, Allen went to the closet and withdrew a blanket to spread over the couch in his study. Giving Simon a moment to catch his breath, Allen was thinking about what was to come . . . or should that be, 'to cum' . . .

Turning to Charles, "Would you like to take this young man's virginity?" Allen already knew the answer, as he and Charles had discussed this earlier in the afternoon. Charles' dick was a bit easier to accept that Allen's would be; they were giving the young slut some time to work up to Allen's thicker dick.

Motioning to Simon to join him by the couch, he positioned him to bend over the couch now covered by the blanket, Picking up the tube of lube that always seemed to be present, he smeared a glob on Simon's ass crack and inserted a sizeable dollop into the tight man pussy opening with his finger.

Handing the tube to Charles, Simon looked back to see Charles liberally coating his with the lube. "Are you ready, Simon?" asked Allen. Seeing his nod, Allen turned to Charles, "Take this slut's virginity. Show him what it is like to be fucked . . . and fucked properly."

Electric thrills of excitement shot through Simon when he heard his virginity was to be taken, right here and now. He bent obediently over the couch and stuck his bottom out invitingly, gasping with pleasure as Mr. Dalton began to lube him up. For days he had been longing to to have Mr. Dalton pop his little cherry, but now that he'd had this very pleasing introduction to Charles, he was not at all disappointed. Having Mr. Dalton right there directing both of them was every bit as good as what he'd been fantasizing about.

It was such a rush to be so desired. Simon's opening was twitching with anticipation. He knew it was going to hurt, and Charles might not be gentle. Still, his cock remained chubbed up with excitement, even though he'd just cum spectacularly. He was ready for just about anything at this point, and the amount of testosterone in the room right now worked on him like a drug.

He wiggled his ass a little, anxious to be penetrated.

"Please, sir, yes please!" he begged. "I so badly need to be fucked!"

Allen and Marilyn had previously set up a camera in the study so that she could see the taking of Simon's virgin ass. She also knew that Charles would appreciate the fact that she was watching. As much as Simon hated the possibility of being involved with a female, Charles and Allen often shared Marilyn . . . much to the enjoyment of all three.

Charles was completely erect and ready for the task at hand. He stepped up behind Simon, Allen gave his cock one more coating of lube, then gently nudged Charles' ass and whispered in his, "Fuck our little slut. Make him feel every thrust and fill him with your hot cum. We want him to remember this for a long time."

Simon's fists closed around the plush blanket that had been draped over the couch, scrunching it in his hands as he anticipated what was to come, feeling Charles step behind him. He just barely heard bits of the whisper, and the phrase our little slut was about the most glorious thing he'd ever heard. It no longer mattered what he'd been before, or what his family intended him to be. This was what he was now, and he didn't need to be anything else.

He couldn't wait any longer. He thought he might scream if he didn't get a cock inside him right away.

Then it was there, the warm rounded head of Charles' hard, lube-slick cock pushing against his prepared opening. He knew what to do instinctively, pushing out against it as the hot masculine flesh pressed through his muscular ring, pressed hard to try to get all the way inside.

Simon cried out and clutched the blanket harder, fighting not to let his body tense up as pain speared into him. He knew he'd been well prepared for this, his inner muscles trained to allow intrusion, and would soon be more welcoming of this new intruder. Breathing deeply, Simon turned his head, wanting to see what Mr. Dalton was up to while his virginity was being taken.

Allen stepped to the side as Charles began his assault on Simon's tender ass; the initial thrust, while successful in breaking thru the tight opening, brought a cry from Simon, totally expected. Charles held his position until Simon gathered himself, then began a slow, dedicated thrust for total penetration of Simon. Allen's cock stiffened at the sight; he could only imagine how wet Marilyn was up in their bedroom watching this take place.

Yes, this young man was likely going to be their son-in-law, but he was going to be a part of their family in so many other ways.

Simon took a deep breath as Charles buried his rigid shaft in him, then began a rhythmic thrusting in and out. Simon's cock returned to its aroused state, this time from being fucked by another man. He will find it is not uncommon for a man being fucked to also achieve an orgasm at the same time as the one fucking him.

Allen looked at both men, "Take your time, Charles; we want Simon to enjoy the full benefit of his first fucking. Once you get comfortable, Simon, you can also participate by stroking your cock as Charles fucks you . . . a mutual orgasm is an incredible feeling."

Sweat was beginning to bead on Simon's heated flesh as Charles's cock began a steady fucking rhythm. At first he felt he was being torn apart, but it didn't take long for the burn of agony to settle into a burn of pleasure, and the sensation of being filled was so very right!

"Oh, fuck... oh, fuck... oh, fuck!" he growled, feeling things long repressed in him being set loose.

Soon he reached down with one hand to begin stroking his throbbing erection. He could already feel it would be a tremendous one. His ass clenched around Charles's thrusting cock, encouraging his pleasure.

Allen stood patiently by Simon's side . . . as if that were possible. Simon, his protégé was being fucked for the first time and it was indeed a marvelous sight . . . the smile creeping over his face, the smile on Charles' face as he prepared to cum deep in Simon's man-cunt.

Allen slowly stroked his own cock, now fully erect . . . his own orgasm not going to happen until the scene in front of him played out . .

"That's good, Simon, keep squeezing that cock in your pussy. Charles wants to give you his hot cum. Deeper, Charles, fuck our little slut deeper."

Watching these two faces; I know that two powerful orgasms are set to erupt. And now, Charles arches his back for one more deep thrust . . . I know the telltale sign of his orgasm . . .

"Now, Simon . . . take it . . . all of it . .. feel that hot cum in your pussy."

Simon paid close attention to Mr. Dalton's instructions, not in the least because his words were so damned sexy, and clenched up his inner muscles to give Charles a good squeeze. He could hear the man moaning with pleasure and felt a rush of pride and excitement.

Since he couldn't see Charles' cock drilling into him, Simon watched Mr. Dalton stroking himself, loving that he was getting off on directing them, and watching them.

...feel that hot cum in your pussy.

"Oh fuck yes!" Simon cried out. "Fill me up, sir, give it to me, all of it! I want you to cum in me so hard I can taste it!"

He felt the final thrust, the intensity, the tightening grip of Charles' hands on his hips. Then he felt the hot flood.

"Oh god!" Simon yelled, pressing his ass back agaist the man as if to force him even deeper. Charles' cock was twitching, pulsing inside him, and Simon could feel his innards get all squishy from the invasion of a prodigious load of cum. It was the most incredible thing he'd ever felt, and immediately it set off his own orgasm.

Simon yelped, his whole body shaking as he jerked himself to a powerful climax, spurting his creamy load all over the blanket beneath him.

"Well done, well done . . . both of you! I think you both need to head into the shower and make sure you are both cleaned up; I'm sure you can figure out how to do that. I will join you shortly . . . someone needs to figure out how to make me cum."

As Simon and Charles stand up and slowly regain a normal breathing pattern, Allen takes a cock in each hand and caresses them gently . . . "Jesus, these feel so good in my hands . . . and both coated with a layer of cum. Simon, please make sure that Charles is properly thanked for taking your virginity."

Simon gave Mr. Dalton a slightly goofy grin of mixed tiredness, satisfaction, and pride. He shivered as the older man gave his sensitive dick a little rub, and leaned against Charles' solid body, both of them warm and flushed from their recent cums. He turned to grin up at Charles, hoping they could put their heads together (maybe literally?) to give Mr. Dalton a good cum.

"I'll definitely make sure this fine gentleman is well thanked," he promised, and took Charles' hand to lead him to the shower.

This was certainly a new experience for Simon, but he wanted to embrace all of it. The moment they were in the shower stall, before Charles could be rinsed off, he dropped to his knees and began licking the cock that had just filled his ass with hot cum.

"That was incredible, sir," he said between licks. "I'm so honoured to have given you my cherry. I might not have any experience, but I think you are an absolutely champion fucker. Thank you so, so much. I loved your cock in me... and I loved you filling me with your cum. If there's anything I can do to make you feel more pleasure, please let me know."

Giving Simon and Charles a couple of minutes to adjust the shower and focus on each other, Allen entered the shower to see Simon on his knees, removing the traces of cum from Charles freshly drained cock.

Simon looked over at Allen, "Join us, Allen. Perhaps Charles and I can bring you a bit of pleasure this afternoon."

As Allen stepped into the shower, he gave Charles a warm embrace; they had shared many a shower together, often the two of them, sometimes with Marilyn sandwiched between them, and once in a while with Marilyn on her knees sucking both of them.

Simon reached for the bottle of mouth wash that Allen kept in the shower and, after rinsing, turned his attention to Allen's stiff shaft. Handing the bottle to Charles, Simon wrapped his fingers around Allen's swollen balls and prepared to swallow his hard cock.

Charles rinsed as well and turned to Allen, exchanging a passionate kiss, before sliding his lips down to tease and suckle at Allen's nipples, his hand on the back of Simon's head.

Simon contented himself for a while with sucking Mr. Dalton's cock, feeling incredibly sexy with the two men standing over him. His hands reached for anything he could grab and caress, wanting to stay connected to both of them. His eyes flicked up, squinting against the water to see the two men kissing deeply, and then Charles sucking at Mr. Dalton's nipples. The sight turned him on all over again, and he moaned against Allen's cock, sliding his hands all over both of them.

Knowing that making out was part of their sexual play brought huge excitement to Simon. He longed to be part of that, and felt he was missing out on something amazing. He'd been fucked by a man just now, sucked a couple of cocks, and he still hadn't kissed a guy. Maybe he needed to prove himself somehow before being invited that close.

Simon continued to suck Mr. Dalton's cock diligently, wanting to taste his cum again, wanting to bring him all the pleasure he could. He wrapped one arm around each of the men's thighs, and caressed both bottoms as he continued his blowjob, now and then peeking up to get an eyeful of what they were up to, craving to earn those privileges.

Allen was enjoying the dual attention, Simon's mouth and tongue on his cock and balls, Charles' lips and tongue on his nipples; both men increasing the tension in Allen's balls, ramping up toward an explosive outburst in Simon's mouth. Allen could feel a hand on his thigh and butt, probably Simon looking for whatever he could reach and caress on the two men.

Whispering to Charles, "I know you want my cum, Charles, you always do; why don't you get on your knees and share it with Simon?"

Charles traced his lips down Allen's torso and thru his pubic hair, then kneeling beside Simon, both of their hands now squeezing and caressing Allen's ass. As Simon sucked Allen's hard shaft, Charles leaned in and swallowed Allen's balls, rolling his tongue over and around them like a hard gumball . . . a technique he knew Allen particularly liked.

Simon didn't hear what was whispered between them, but he smiled around his mouthful of cock when he notice Charles kneeling next to him. He gave Mr. Dalton's backside a particularly friendly squeeze in his excitement, the proximity of Charles' mouth to his giving him a hint as to what might be coming. His first fuck had been a revelation, and he was thirsty for more firsts.

He loved the feeling of the other masculine body so close to his, both of them so naked and slippery beneath the warm water of the shower. He reached for Charles, stroked his wet hair, and massaged the back of his neck, hoping he wouldn't mind the contact.

He heard the noises of pleasure Allen was making with two mouths working on him, and the salt tang of precum spread over his tongue. Simon moaned hungrily in response, knowing it wouldn't be long now.

Looking down, Allen was indeed aroused by the two heads he saw bobbing up and down around his 'privates'; Simon sucking and swallowing his cock, and Charles swirling his tongue all over his balls. Two hands on his ass, one each from his two lovers, only added to the thrill.

Before long, the two of them found that by sucking up and down on both sides of his engorged shaft not only aroused him further, but gave Simon and Charles the opportunity to flick their tongues back and forth.

By now, Allen's labored breathing gave every indication of his impending orgasm . . . a blast that would undoubtedly satisfy the two of them. He reached down and, hands on the backs of their heads, held them steady as he began to release his flood of hot seed.

"Now, my lovers, take my hot cum!!"

Simon moaned, feeling out of control turned on as Charles joined him at sucking Mr. Dalton's throbbing cock, and now and then their lips and and tongues met around the shaft. He licked more hungrily at both Allen's cock and Charles' mouth, craving more, more of everything, more of this incredible rush.

With one hand Simon massaged Mr. Dalton's ass, and with the other, he reached for Charles, rubbing his neck, and his chest, and then experimentally tweaking one of his nipples.

When Allen took hold of them and announced his impending load, Simon opened wide, feeling his cheek mash against Charles' as they both primed to receive the huge load of hot cum spurting forth from Mr. Dalton's cock. He stuck his tongue out to get a little extra as the flow waned, and his tongue collided with Charles'. He couldn't hold back now - as if possessed by an outside force, he turned his head and threw his arms around Charles, mashing their mouths together and mingling tongues, sharing Allen's load back and forth. It wasn't anything like he imagined his first kiss with a man would be, but he wouldn't trade this for anything. His cock was pointing straight up and twitching excitedly.

Allen leaned back against the shower wall, watching his two lovers . . . experienced and youthful . . . exchanging his cum as they sloppily kissed and traded tastes of his cum between them. Charles was close to his age and usually quite reserved, but this opportunity to take a "newbie's" virginity and then to share the cum of a man he looked up to with the same cocksucker was a new high for even Charles . . . and he was all in!

Allen stepped back under the cascading shower and allowed the spray to wash over him and rinse his body of the sweat and remaining residue of the joint blow-job by Simon and Charles. Looking down he could see that the young gun, Simon, was already hard again . . . and that would need to be dealt with.

"Stand up, guys . . . I don't think we are quite finished here yet. Seems as if young Simon has another 'woodie' that we must attend to."

As the two stand, Allen turns Simon's back to Charles' chest. Immediately, Charles wraps his arms around Simon and begins teasing and tweaking his nipples; Simon's jerking cock shows the impact of such teasing.

Allen drops to his knees, caresses Simon's torso, down to his thighs and then takes the young man's balls in his hands, playing with them for a minute or so . . . then leaning forward, mouth open, tongue searching for Simon's head and the sensitive slit.

Simon groaned and leaned back against Charles, his body responding powerfully to the teasing of his nipples. Electric shivers of pure pleasure coursed all over him, causing his hips to jerk, fucking into the welcoming warmth of Mr. Dalton's mouth. One hand cupped Allen's head; the other reached back to hook around Charles' neck, keeping them both close to his aroused young body.

"Oh god, oh fuck, oh god....," he moaned, almost losing his mind with the overload of pleasure. "That's soooo good, oh, FUCK! You guys turn me on so much!"

When he wasn't watching the very sexy sight of his girlfriend's dad sucking his cock, he was craning his head back to seek more kisses from Charles, suckling at his neck when he couldn't find his lips. The only thing keeping him from shooting his load immediately was the fact that he'd cum so recently. He wanted to savour this experience.

Looking briefly up to Charles, Allen was quite certain that they were giving Simon something that he had never imagined in his wildest dreams. Allen was well aware of Charles' devious thoughts . . . how he loved to play and be played with. As Allen sucked Simon's cock, he slid his hand between the two men standing in front of him and gave Charles' dick a good rub before wrapping his fingers around Charles' balls.

Allen had learned over the years that Charles' balls were as sensitive to finger caresses as his cock head was to oral stimulation . . . and this seemingly innocent caress, was bringing Charles to a full hard-on . . . and was now making its presence known against Simon's freshly-fucked ass.

How much longer could Simon hold out before spraying his cum into Allen's warm mouth? The combination of Allen's tongue on his dick and Charles' cock riding the crack in his ass . . . what young body could hold back an orgasm from that treatment?

Simon felt the activity behind him and soon Charles' hardening shaft was distinct and throbbing along his sensitive cleft. He released a loud moan and ground his ass against that exquisite warm hardness. It enlivened the still pulsing ache in his backside that felt so sweet in the memory of his first fucking.

Yelling out profanities, Simon bucked his hips back and forth, alternately grinding on Charles' cock and fucking Allen's mouth. He was in heaven, and certainly he wouldn't last long at this rate.

His body tensed up, and his mouth flew open as the powerful climax hit. Allen's mouth filled with his fresh young seed, and delicious aftershocks sent Simon's flushed body into an all-over tremor. He went weak, relaxing back and trusting himself to Charles' strong arms.

Allen could sense the threatening blast from Simon's mouth, and was ready when it came. One hand cupping Simon's balls, the other gripping the base of his shaft as the warm seed flooded his throat. The taste, the sensation was incredible . . . he could only imagine how much Marilyn would love to be in his place, although that is not likely to happen, given Simon's intense dislike of female contact.

However, filling Marilyn in on the details later would certainly drive her to draining his balls tonight with her swallowing every drop of his hot cum. Charles would be begging him for another 3-some with him and Marilyn soon, also.

Finally rising to his feet, Allen looked at his two lovers "Gentlemen, I think that is enough for one afternoon. Let's finish with a quick shower. I'm sure Simon will be back over here this evening to see Alyssa, at least that is what I think she said this morning."

Showers wrapped up, Simon on his way home, Allen and Charles return to his office where they are met by Marilyn. "Charles, you owe me something. After watching your performance with Simon, I need to feel that hard cock in me before too long."

Charles promised to deliver on his debt to Marilyn and headed home. After a warm embrace, and a promise of an early bed time, Marilyn headed to the kitchen to fix dinner.

Simon had never felt so happy and satisfied in his life. Every inch of him was abuzz with pleasure, though he was quite exhausted from all the action. He got in as much touching and kissing as he could before the shower was over and they had to part ways for now. Before departing, he thanked both of them profusely, and made abundantly clear his desire for more playtime.

At home, he paused in his kitchen for a glass of water, and his sister strode in, giving him an odd look.

"What in the world are you wearing?" she giggled, noticing his close-fitting shorts and polo.

Simon tried very hard not to blush. He shrugged as nonchalantly as he could manage. "Tennis clothes. What's your problem?"

"Nothing," she tittered, pouring herself a glass of sweet tea. "Maybe we should get you one of those little pink flutter skirts from the Venus Williams collection."

"Grow up," Simon muttered. He quickly finished guzzling down his water and left the kitchen before he could start looking incriminated. He felt stupid now for not changing into different clothes after his 'game', but what he was wearing wasn't that bad. At least, he was pretty sure his sister didn't suspect anything, but was only looking for an opportunity to tease him.

He had a short nap, and talked himself out of the boner he woke up with so he could have a civilized dinner with his family before spending the rest of the evening with Alyssa.

Simon's sister smirked at him across the dinner table a few times, but he ignored her. His dad stayed silent for most of the meal, checking things on his phone in between bites rather than talking to his family, which they were quite accustomed to.

"I hear you've been playing tennis," Simon's mother finally spoke up to fill the silence, ever the family diplomat.

Simon nodded. "Mr. Dalton is teaching me. He's very good."

"Since when are you into that stuff?" his sister challenged.

"Leave your brother alone," their mother scolded. "Simon, I'm proud of you for finally getting into athletics. Maybe you could play with your father sometime."

Simon nearly choked on a mouthful of roast beef, and quickly gulped down some water. His cheeks felt rather warm. "I dunno that... dad would be interested."

"Hmm?" the Senator murmured, glancing up from his phone and meeting Simon's eyes.

"Tennis... we were just talking about tennis," Simon said, his voice nearly cracking. "But I'm sure you wouldn't want to play."

"Hm... I used to play a mean game. Learning a lot from Allen?"

Simon shifted in his chair. He was realizing with slight panic that if he went too far with this, he might have to actually learn tennis. "Well... maybe," he equivocated. "I'm not naturally that coordinated, so I'm still not good. He really is... quite excellent, and... I'm still new at it. Maybe I never will be a very good tennis player, but... I'm at least keeping in good shape. And it's nice to spend time over there. They treat me like part of the family."

As Simon finished speaking, he realized his tone had risen from uncertain to almost spiteful and accusing as he reached the last sentence. The subject matter had poked at a particularly tender spot he'd almost forgotten was there. His dad looked up at him again, eyes narrowed.

"Why the attitude?" Senator Thorpe challenged. "If you want to play tennis, we'll play tennis!"

"Oh of course," Simon shot back. "It's just that easy! Quality father-son time, as if that's something you've ever done! Have a look through your schedule on that phone that's surgically attached to your hand - if you've got a single appointment on there you can easily set aside to devote to your family, I'll be checking the weather forecast for reports of hell freezing over."

The Senator's grip tightened on his phone, and a vein was starting to pop out on his flushed forehead. "What a lot of melodramatic nonsense. You think I don't give my family any time? What are we sitting around the dinner table for?"

"I don't know, dad," Simon retorted. "It took you like, half an hour to even look up from your phone. Maybe we're just here to pretend we're a family, the way you've always pushed us to, but it's all just bullshit, isn't it?"

"Simon!" his father snapped, slamming a fist down on the table.

The two women had gone silent and stone-faced. Simon had never felt so bold. It was the first time he'd ever said a swear word in front of his family.

"Yell at me all you want," Simon replied, his tone still escalated, but there was a certain serenity behind it now. "I don't care. It doesn't change anything. You know why I like spending time with the Daltons? They make me feel like I belong, and like I can be myself, rather than just being part of someone's public image."

He sighed harshly and dropped his fork, not very hungry anymore. He stood up, and smoothed out his clothing. "I'll play little Master Thorpe, the perfect Senator's son, for you until I'm ready to get married and move out. Until then, I'd rather not spend more time around here than I have to! Thanks for dinner."

Simon hurried up the stairs to change, and soon found his mother following after him, wanting to talk. He was as nice as he could be, and indulged her desire for a mother-son chat. It turned out to be not so bad - he told her a few things about Alyssa, and how she liked the idea of promise rings, and his mother took him to her bedroom to give him an antique emerald ring that had belonged to her grandmother, something he could give to Alyssa as a pre-engagement symbol.

Simon dressed in his usual upscale, preppy fashion in anticipation of spending the rest of his evening with Alyssa, and slipped the ring into his pocket to give to her. Even though he thought this promise ring thing was sort of idiotic (why so many girls nowadays seemed to want three fucking rings to prove a man's love, he could never understand) but it wasn't costing him anything to make her happy, and making her happy would make her parents happy. That could only lead to great things for him.

Soon he was headed off to the Daltons' for the second time that day.