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

Allen was not surprised at how quickly Simon exploded on his cock after the plug was inserted; and, as much as Simon did not think he had any reaction to being around a naked female, the mere presence of Marilyn on Allen's side, her fingers buried in her pussy, her moans of arousal, and the scent emanating from her cunt had to have an additional effect on Simon.

As soon as his ejaculation was complete on Allen, Simon dropped to his knees and began licking his cum from Allen's cock and pushing Allen toward an explosive orgasm of his own that Simon would devour. Mrs. Dalton could barely hold herself up as she watched young Simon give himself thoroughly to her husband . . . god, what would happen later tonight when they recounted this scene after going to bed??

She finally dropped into the nearby chair and spread her legs wide, her fingers pawing at her naked sex, grasping for that elusive orgasm . .. which came just as Allen exploded into Simon's mouth . . ."Holy fuck!!" was all she could say.

Simon was beyond delighted - he hardly had to strain his jaw or throat to get Mr. Dalton to cum really hard. He felt the hot jet hit the back of his throat, taking very little time to fill his mouth with the older man's cum. He swallowed, and the man was still cumming. He could hear the orgasmic noises Mr. Dalton's wife was making, and it certainly wasn't a turnoff - there was something damned exciting about three people together in a room making each other cum. Nonetheless, he was totally focused on the cock.

Simon leaned back and let the last few spurts of Mr. Dalton's seed coat his face, hoping they would enjoy him looking incredibly slutty, like a naughty little bottom twink in a porno. He leaned back, looking immensely gratified as he beamed up at his girlfriend's dad with his face painted in cum. He was still pretty turned on, and reached back to press against the plug up his ass as he licked his lips slowly.

"Pardon my language, sir," he said, "but that was pretty fucking amazing."

"Simon, please go into the shower. Leave the plug in your ass for the time being."

As soon as Simon goes thru the secret opening, Allen waits until he hears the shower running, he turned to his wife, "It seems your had a very satisfactory orgasm, my love? Would your like to join us in the shower. I intend to give Simon the larger plug for his young ass."

The two of the Daltons walk into the shower room together, "I hope you are not embarrassed by Marilyn's presence, Simon. I'm sure you are quite surprised by her willingness to participate in these activities with me; I would think that her vocal orgasm in the den would tell you how much she enjoyed what you were doing for me."

Handing Simon the shower gel, "You may start by cleaning my cock, and then your ass and cock. I know you have an aversion to contact with a female body, but if you and Alyssa are to be married, you will have to overcome that. So, for now, I would ask you to wash Mrs. Dalton's back. You will not need to come in contact with her tits or pussy, or even her butt, for now; but that day is coming when you will have to conquer those feelings."

Simon sighed and did a more than thorough job of cleaning up Mr. Dalton's dick, drawing it out as long as he could, followed by a good show of washing himself off. Finally, like a little boy reluctantly going about a chore, he put on a determined if slightly petulant expression and washed Mrs. Dalton's back. He wasn't so much embarrassed as uncomfortable, and wished he didn't have to make these compromises.

Marrying Alyssa would get him a house, and freedom from his family. It had seemed worthwhile, but now that he'd experienced another man's body, he knew just how little he wanted a woman's. However, there was more now to sweeten the deal - staying with Alyssa would get him Mr. Dalton. Now he was hooked on that sweet daddy dick, and he couldn't imagine he'd get to keep it if he admitted to being in over his head.

After spending a couple of minutes on Mrs. Dalton's back, he turned questioningly to her husband.

"Is that okay, sir?"

"You need to ask Mrs. Dalton, Simon. After all, she is standing right there in front of you."

It's obvious that Simon's only interest is his relationship with Mr. Dalton and his cock, but the family is going to be a part of the deal. Marrying Alyssa will require him fucking her; so he better get used to the female body . . . at least a little. Who knows, once he buries his dick in a tight cunt, he might actually like it!!

"OK, Simon. Turn around and bend over, grabbing your ankles. Hand me the lube, Marilyn . .. and the new plug. Let's see just what our little slut can handle. Why don't you be the one to lube that sweet little pucker?

Watching as Mrs. Dalton squeezes a quantity of lube on her fingers, with a nasty smile on her face she proceeds to smear it all over Simon's tight hole, even sneaking a finger inside to test this resistance.

Showing the plug to Simon, considerably larger than the first one, "You need to be able to take this . . . then we will see what comes next."

Simon squirmed awkwardly, not sure what to make of where all of this was going, but he continued to obey. He breathed hard as he held onto his ankles and tried to relax. With Mrs. Dalton preparing him, however, he tensed up and struggled to get himself loose enough to accommodate a plug.

When Mr. Dalton showed him what was going inside, he gasped, and tensed up even more.

...then we will see what comes next.

If that meant what he hoped it meant, Simon knew he had to rise to this challenge. Determined, he shut his eyes and concentrated on his fantasy of being fucked, to have a nice solid male body against his, pressing the heft of a thick, hard cock up inside him....

Finally he managed to transcend most of his tension. He felt the plug pushing inside and groaned, gripping his ankles tighter and pushing out to loosen his ring of muscle.

"Stay in that position for a couple of minutes, Simon. Give you body a little time to get adjusted to the intrusion. When you are ready, you can try to stand up and see if you can keep the plug in."

As Simon maintained his position, Marilyn and Allen watched as he struggled to keep the plug in, fully knowing that if Simon was wanting to be fucked, he needed to prep his body for that. After a couple of minutes, Marilyn finished rinsing, grabbed a towel and her robe and left, knowing that Alyssa would be home before too long.

"It's just us now, Simon. How are you feeling?"

As Mrs. Dalton slipped away, Simon found himself relaxing more and more by the moment. Breathing deeply, he found that the searing pain of the unprecedented intrusion was beginning to settle, and the raging warmth all up his backside was starting to feel kind of nice. Still, the intensity was rocking his body, and he found himself feeling quite raw all the way through.

Bashfully, he leaned slowly toward Mr. Dalton and let his head rest tentatively on the older man's shoulder as he took breath after shaky breath. He wasn't sure why this felt like such a risk when he'd sucked the man's cock a few times by this point, but he was worrying that just putting his head on Mr. Dalton's shoulder might not be okay. At least it was comforting to be asked how he was feeling.

How could he even begin to describe what was going on inside him?

"Oh... I'm feeling... everything," Simon stammered. "Happy... scared... proud... confused... excited? And... oh, god... this thing up my ass feels amazing!"

"Simon, I think that is enough with the larger plug today. Turn around and let me slip it out of your butt."

Once the plug was removed, Allen picked up the container of lube and turned back to Simon.

"Now, I want you to bend over once more, hands on your knees."

As Simon did as instructed, Allen coated his finger with the lube. Running his finger up and down the crack in Simon's ass, he felt the young man squirm under his touch. Finding the tight opening with his finger, Allen began to penetrate Simon's man pussy with his finger . . not stopping until his finger was buried in Simon's man pussy.

Simon sighed as he followed instructions, whimpering as the plug came out. He felt so empty... until he bent over and felt Mr. Dalton's finger enter him.

"Ohhh...," he moaned, his passage tightening around the invading digit. He began to pant and gasp, finding the penetration extremely intense, not only because his ass was so raw from having a huge plug stuffed up inside it not a minute ago. It was intense because a part of Mr. Dalton was inside him, and the feeling was glorious.

"Oh, yes sir, thank you sir," he babbled, pushing back a little against the man's hand as if to invite more.

"Clinch your ass as tight as you can on my finger, slut. I know you are wanting to feel a hard cock in there, but we are taking this in steps. That will come soon enough."

Allen had to admit to himself that he was looking forward to taking Simon's virgin man cunt; that will come, maybe tomorrow, may the next day, but it would come.

"I know it has been an exciting day, and a challenging one, for you Simon; I think it is time we shower and call it a day."

Picking up the gel as Simon stepped back under the cascading water, Allen reached down and took Simon's still semi-hard cock in his hand and stroked him gently, bringing him quickly back to full erection. "Yes, Simon, you may cum. Shoot your load all over my hand. You need to cum after all you have experienced today."

Simon clenched up nice and tight, loving the sensation of squeezing Mr. Dalton's finger with his ass muscles. He knew it would only get better.

The shower was a wonderful experience. He loved admiring Mr. Dalton's body, and he hoped the feeling was mutual.

The older man's warm, practiced hand on his cock was heavenly, and Simon leaned closer to him, sighing with pleasure.

"Oh, yes sir," he breathed, full of gratitude. "Yes, I do need to cum... so bad...."

His legs trembled. He placed one hand on the cool tiled wall for balance as the strong feeling began to overtake him. He groaned loudly, letting everything go, pumping his eager load into Mr. Dalton's fist.

As Simon began to cum, Allen plunged his finger with a little more vigor into his ass, feeling Simon maintain a tight grip on the intruding digit. The effect on Simon was an orgasm to 'be proud of'. The hot seed quickly coated Allen's hand and began dripping to the shower floor.

"Nice, Simon. A load you should be pleased to share with anyone."

Simon didn't know it, but Allen (with Marilyn's approval) was going to invite one of his closest friends over the day after tomorrow to be the one to initially take Simon's virgin pussy. Marilyn would not be present, but a hidden video camera would record all the action for her to view with Allen later that night.

As they exited the shower and dried off, Allen turned to Simon, "I have a business meeting out of town all day tomorrow. I would like you to come by the day after for our usual afternoon lessons."

Simon beamed brightly at the praise over his cum. He hoped to inspire lots more praise, wanting Mr. Dalton to be so proud of him, impressed, and to truly desire him.

With a light, pleasant ache throbbing happily all up his backside, Simon took his time drying himself, wanting to draw out his time with Mr. Dalton as long as possible, especially when the man informed him he'd be gone tomorrow.

"I understand, sir," Simon replied compliantly. "I'll spend tomorrow on homework - that will please my father. I look forward to playing with you again the day after."

"Yes, I don't want you to do anything to displease your father. And I'm sure that Alyssa will be wanting some your time this evening or tomorrow evening. Right?"

As Allen and Simon walk back into Allen's office, Allen wraps his arm around Simon; "Simon, I know this will be difficult, but when you come in from now on, if Mrs. Dalton is present, I think it would be appropriate for you to give her a hug . . . nothing more than that, just a brief hug. That will make her and Alyssa very happy . . . and Mrs. Dalton will continue to encourage the time you and I spend together."

As Simon prepares to leave, Allen leans in and gives him a soft kiss on the cheek.

"I'll make time for Alyssa," Simon promised. "And if it would make all of you happy, of course I can hug your wife. I can handle that."

The arm around him was a pleasant surprise, and the kiss, even more so. It set his heart racing. It may have been a little thing, but it seemed to have huge significance to Simon. It hinted at nudging their relationship into a different realm, and although he didn't want to get carried away and lose his head over something that might not mean what he thought, he was feeling much more optimistic about his future with Mr. Dalton.

"Thank you, sir. I'll see you the day after tomorrow. Do you have any instructions for me in the meantime?"

"I would like you to refrain from masturbating as much as possible; save your erections and ejaculations for when we are together. And, take this small butt plug with you. Insert it with plenty of lube at night. See how long you can keep it in over night."

Seeing Simon paying close attention to his direction, Allen is becoming more confident that Simon can be the husband that Alyssa needs . . . in addition to being the slut/slave/partner that he desires . . . and someone who will, as required, allow Marilyn to at least observe their play times.

"See you in a couple of days, Simon. Come prepared for a good time and to cum!!"

"Absolutely, sir!" Simon exclaimed. "I'll do just as you say. Guaranteed, I'll be ready to cum a lot! I hope you'll be ready for it..."

He grinned cheekily as they said goodbye.

That night, Simon had to struggle not to touch himself as he eased the small plug into his ass. He was accustomed to the routine of masturbating at least once a day, and his excitement was at new levels after what had happened today, and what might happen the day after tomorrow. The plug made his ass throb delightfully, and his cock was persistently hard. He used all the self-control he had to avoid making himself cum, and while it was a bit of a struggle, he eventually fell asleep.

After Simon left, Allen wrapped up a few more details for his meeting tomorrow and then headed up to the bedroom to change for dinner. Marilyn was stretched out on the bed, naked . . . "So tell me, love, how did the rest of the afternoon go?"

"I told Simon that I will be out of town all day tomorrow so he will not be back until the next day. After keeping the larger plug in for a few minutes, I removed it and then jerked him off until he shot a massive load in my hand. Before he left, I told him that he is not to masturbate until he returns. And he is to wear the smaller plug to bed at night."

I watch as Marilyn spreads her swollen pussy and buries a finger in her cunt at the details of your Simon's initiation into my secret life.

"I'm thinking about inviting Charles to joins us when Simon returns. His cock is a bit smaller than mine; that might be a good one for Simon to experience first. What do you think, love?"

Simon awoke with an ache in his ass, and a steel-hard erection tenting his covers. The plug inside him felt so good, and must have inspired some incredibly erotic dreams. He thought he could remember wisps of them, but they disappeared in moments. It didn't matter - he was living a real life sexy dream.

He felt a little dampness around the head of his cock, and was worried he might have had a wet dream. He reached down and felt around a little. There was no sticky residue of an ejaculation, but he had definitely been precumming like crazy.

Groaning, Simon carefully peeled back his covers, looking down sternly at his angry red hard-on.

"Not today," he muttered, knowing he had to save it for Mr. Dalton. Not that his dick knew what was going on.

He got up slowly and groaned some more, walking gingerly and a bit bowlegged on his way to the bathroom, the little plug inside him feeling three times its size after being stuffed in there all night. While standing under the warm spray, he gnawed on a clenched fist to keep from crying out as he very slowly removed the plug. At first it was a blessed relief, but soon he felt quite empty without it. He went about his shower, touching his cock only as much as was necessary to clean it; too much, and he could have easily set himself off and wasted a big load of cum that belonged to his girlfriend's dad.

He wore two snug-fitting pairs of underwear and baggy jeans that day, worried about going to school with an obvious boner. It didn't seem to want to go down.

Even sitting in class seemed to turn him on. The hard plastic chair beneath him was unyielding, and his backside still ached so deliciously. He found himself occasionally grinding his ass against the seat, causing that warm ache to flare up. He stuck his hand in his pocket and tenderly stroked the trapped head of his excited cock, unable to resist teasing himself at least a little, but he let up before it went too far. He wished he could send Mr. Dalton some totally inappropriate texts, but he didn't want to cause either of them any trouble.

The day seemed to last an eternity.

To keep himself occupied after classes, he did all the studying he could, and later took Alyssa out to a movie, and then for ice cream. He was starting to enjoy making her happy - he knew how much it would please her dad.

Less than a day, and he'd be with Alyssa's dad again. Tonight he'd put the plug in again, and he might just manage to go a second night without blowing his load.

After a wild night with Mrs. Dalton, Allen gets up early the next morning and leaves for his all day meeting, an hour's drive. The meeting, while very productive, last much longer than anticipated and is well past dinner time when he gets home. Marilyn and Alyssa have already eaten; Allen picks up a sandwich at a local drive-through and eats at his desk, reviewing paperwork from the day's meetings.

After a couple of phone calls, including one to Charles to invite him to a "meeting" tomorrow afternoon, he stops in the family room and chats with his women for a few minutes before heading up to bed. Tomorrow should be an exciting day!!

==========

The next morning rolls around; Allen is up at his usual time; coffee at his desk; phone calls to his business partners; confirmation call from Charles for this afternoon. Lunch out with Marilyn and then back to his office to await Charles and Simon.

Simon once more awoke with the ache of the plug in his backside, and once more narrowly avoided cumming as he showered and set about his day. He could scarcely concentrate in school for his excitement, and the day dragged on as he barely contained his arousal and looked forward to all the fun that was to be had with Mr. Dalton. He longed to be fucked, and hoped today he would be deemed ready.

After school he followed his usual pattern, putting on his most daring set of briefs and a tennis outfit before hurrying as fast as he could to the Dalton home. His heart was thumping in his chest, and his cock was throbbing along with it as he let himself in the back door and headed to the man's familiar study.

Sitting in his office, his friend Charles across the desk, Allen looked up as Simon entered the room. "Good afternoon, Simon. This is my dear friend, Charles."

A questioning look on Simon's face, "Charles, this is the young man I was telling you about. Now be a good man and show Simon what you are going to be sharing with him this afternoon."

A smiling Charles stands and quickly drops his tennis shorts, revealing that he is not wearing underwear . . . a nice sized cock (a tad smaller and not as thick as Allen's) . . . at the same time, Allen stands and walks around the desk, naked from the waist down.

"Simon, please tell Charles the restrictions you have been under the past couple of days and tell us how well you have followed the direction I gave you."

Simon had been quite startled to find another man in the study with Mr. Dalton, a distinguished-looking man about Mr. Dalton's age. He looked vaguely familiar, though Simon couldn't place his face. Maybe someone his own father worked with...?

The presence of a second man... a second cock... was something he was initially unsure about, but he realized it was arousing him powerfully. He took in the man's smile, and the size and shape of his cock, and was surprised by how quickly he was growing comfortable with this situation. Simon returned the smile, which grew even broader when he saw Mr. Dalton standing beside Charles, both of them with their cocks bared. A pleasant shiver danced up Simon's spine.

"Yes, sir," he responded to Mr. Dalton's instruction, and faced Charles squarely. "Sir, I've been refraining from masturbating under Mr. Dalton's orders, and I haven't cum since two days ago, when he jerked me off. For two nights, I've slept all night with this plug in."

He pulled the small butt plug from his pocket, where it had stayed when not inside him.

"Simon, please undress for Charles; I am quite certain that your naked body will have an effect on his currently soft cock. Right, Charles?"

Simon hands Allen the plug and begins to undress . . . using the box that I have provided for his clothing. Tennis shorts, then shirt into the box . . . that's enough to start getting a rise out of Charles. The t-shirt, exposing Simon's chest and nipples brings Charles to almost a full erection. Allen watches as Charles slides his hand down and starts rubbing his cock. "I take it you like what you see so far, Charles?" Allen asks.

Finally, his briefs and his cock springs forth . . . "Please, Charles, feel free to examine our young slut."