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

A lump formed in Simon's throat when Mr. Dalton snapped at him. Had he gone too far? Was he not supposed to draw attention to the wrongness of what they were doing? Or was the man just deliberately trying to keep him off balance?

As he came down from his second orgasm, and felt the absence of the plug that had been up his ass, a spectrum of mixed feelings was beginning to churn inside him. He wasn't sure he quite understood what was happening here, and he was starting to feel some real guilt over all of it, especially when there wasn't the least bit of tenderness from the older man. Was he just stupid for expecting any such thing? Was Mr. Dalton mad at him?

He quickly dried off, combed his hair back with his fingers, and stood naked and shivering in the office, raw and vulnerable, waiting for whatever was to come.

"I'm sorry, Simon, I shouldn't have snapped at you like that. I hope you will forgive me, and that we will continue to spend time together. I have so much that I would like to share with you . . . and show you some special things that we can enjoy."

Allen walked over to the naked boy and wrapped his arms around him, pulling his close. Allen ran his hands up and down Simon's back, reaching down to caress his butt as he caressed his body. Kneeling down in front of Simon, Allen took Simon's limp dick in his hand and caressed it gently, "Simon, I do believe that we are going to have some special times together; I hope you will continue to be a part of our family. I know that Alyssa is really quite fond of you. Now if have some other clothes to wear, perhaps you would like to stay for dinner this evening."

Before allowing Simon to leave, Allen knelt once more, wrapped his lips around Simon's dick, and swirled his tongue for just a moment.

Simon sighed with relief when Mr. Dalton came out in a much different mood. He leaned into the man with gratitude and a little desperation when he pulled him into the embrace. His father wasn't the type to hug him, and it didn't take a psychiatrist to guess why Simon was getting so much out of this.

He gasped in surprise when the man knelt down, giving his soft cock a little attention. He hadn't expected this at all, and it warmed him all the way through.

"I would like to stay," he whispered shakily. "I brought a change of clothes, just in case. I'm just not ready to go home."

He stroked Mr. Dalton's wet hair and moaned as he felt warm lips wrap around him, and an even warmer tongue.

"I've never done anything like this before, sir," he admitted as the man's mouth parted from his dick. He looked down to meet his eyes. "I'm scared, and I don't really know what to do. I don't know if I can feel about Alyssa the way she feels about me, but... I feel like I'm supposed to. Am I a terrible person?"

"You are not a terrible person, Simon. After you get dressed, come back and I will tell you a bit more about our family."

After a few minutes, Simon was back . . . and joined Allen on the couch in front of the fireplace. Allen place hand on Simon's shoulder. He could sense the tension in Simon's body before he began to speak.

"My wife, Mrs. Dalton, is well aware of my preference for young men, although I will admit that this time with you has been my first action in quite a few months. And honestly, Simon, I have no desire to spend this time with anyone else. You have been a pure joy to spend this time with. You willingness to give yourself totally to me is an incredible feeling."

Allen leaned over and gave Simon a brief kiss on the cheek, hopefully calming some of his fears at the moment.

It was a little strange being fully dressed next to Mr. Dalton now. Simon found himself blushing, and fidgeting. The little touches were soothing, and the kiss made him close his eyes and sigh. At first it baffled him that Mr. Dalton could go from being so strict and almost scary to comforting and kind, but it occurred to him that for some people, being in complete control over another was a very sexual thing, and Simon couldn't deny how naturally he'd taken to the submissive role, and how turned on he'd been, how hard he'd cum. The honesty and gentleness he was getting now from Mr. Dalton was like an answer to a big question that had been hanging over him.

"Your wife knows... that you do these things?" Simon stammered, quite surprised. He shifted a little closer, partially leaning on the older man. "I want to know everything about you, sir. I want you to be totally in charge of me. I want to know what it feels like. And I want to know how you live like this... with these secrets. I thought you were a lot like my dad, but you're nothing like him. He tries to tell me how to be a man, and I don't care anymore. I'll be whoever you want me to be!"

"Simon, I want you to feel comfortable around me and my family; I want you feel comfortable asking me anything. The next time I see your father, I will let him know how much our family thinks of you and that we look forward to you becoming a part of our family if your relationship with Alyssa continues. As time goes on, when it is appropriate, I may include Mrs. Dalton in our conversation so that you will be able to treat Alyssa as she deserves. Now we should probably head up to the dining room."

What Simon does not yet know is that Mrs. Dalton suspects the true nature of Simon's sexuality, and is not concerned about how it will affect Alyssa. Alyssa has some issues of her own concerning men, and a man demanding a normal sexual relationship with her might be greatly disappointed.

More about those concerns, and discussions involving the Mrs. later.

"Yes, sir," Simon agreed, following Mr. Dalton to the dining room. He didn't quite understand everything the man was telling him, but he trusted that he would understand more in time, and was committed to trusting and obeying this man.

Smoothing his clothing and his hair, Simon steeled himself for a dinner with the family. It was going to be surreal, and pretty soon he felt a stirring in his groin. He realized it excited him to be around Mr. Dalton's wife and daughter after fooling around with the family patriarch. The secret they shared was incredibly sexy. He thought about the possibility of doing daring things like touching beneath the table, and maybe inviting Mr. Dalton to his house for dinner, fooling around in his house, with his own parents in the next room. He grinned widely as they entered, and greeted Mrs. Dalton like the perfect young gentleman.

The evening meal was very simple and casual. As expected, Alyssa was surprised to see Simon come into the dining room with her father; she greeted him with a polite kiss on the cheek.

"I invited Simon over this afternoon so that he and I could spend some more time together getting acquainted."

Nothing further was said about the afternoon, just some family chat about the day and what was coming up in the next few days. After dinner, Allen and his wife went down to the family room and watch a little TV while Simon helped Alyssa clear the table and clean up the kitchen.

While alone in the family room, Allen quietly said to Marilyn, "You were quite right in your assessment of Simon. Perhaps you would like to join us in one of our afternoon conversations."

Simon and Alyssa appeared soon after and join the Daltons in the family room.

Simon found himself staring curiously at Alyssa when they were alone together. Now that he'd had an opportunity to experience some form of intimacy with a man, he was even more certain he wasn't attracted to Alyssa at all. Or any other girl. And yet, the fact that she was the daughter Mr. Dalton had made, with the seed that had gone down his own throat this afternoon, was... fascinating.

"What?" she giggled when she noticed the staring.

"Nothing," Simon replied, smirking. "I, uh... had a good time with your dad today."

"I'm glad to hear it. Did he teach you a few things?"

Simon nodded rapidly. For just a moment, he wondered what her expression might look like if he just went right out and told her how much he loved sucking her dad's cock.

They settled down in the family room, with Simon next to Mr. Dalton, and Alyssa on his far side. He was rather exhilarated, being right between them. He kept looking at Mr. Dalton, and at his wife, wondering just how many secrets this family had.

So far it was a quiet evening in Dalton family room; at the end of the program, Allen stood and reached for Marilyn's hand, "Shall we go watch TV or read in the upstairs sitting room and leave the family room to Simon and Alyssa?"

As they started to leave the room, Marilyn turned to Simon, "You must come again and spend some time with Allen; he told me how much he enjoyed the time with you this afternoon." As they left the room, Simon could see Marilyn reach down and give Allen's butt a gentle squeeze, something that Alyssa could not see.

Allen jumped a bit at the squeeze; he knew Marilyn was going to want a full accounting of what happened this afternoon . . . and probably want a ride on that cock herself.

Simon didn't particularly want to be left alone with Alyssa, but the subtle exchange with her mother that hinted at the true state of things between Mr. and Mrs. Dalton fascinated him enough to occupy his mind with fantasies for the remainder of the evening.

Before it got too late, Simon said good night to Alyssa and said he'd let himself out. He needed to go to Mr. Dalton's study to pick up his workout clothes first. He decided to leave his underwear in the box where the man had ordered him to drop his clothes... and a mood came over him as he did so. He took an extra minute or two to leave a fresh load of cum on his little pair of micro-briefs, and an additional minute for a note:

Mr Dalton - I had a great time playing today. I hope we can have another round real soon. Call/text me anytime, and I mean anytime. -S

He scribbled down his number, and left.

After hearing Alyssa come upstairs and sticking her head in their sitting room to tell them goodnight, Allen and Marilyn quickly undressed and crawled into bed. Her hand went immediately to Allen's cock which was already getting hard. "So, tell me Allen, dear, just what happened between you and Simon this afternoon. You do know what will happen after you fill me in on the details."

Allen responded immediately to her touch, even slid his hand down and spread her thighs open to cup her moist pussy; Marilyn was as aroused as he was.

Allen related the entire afternoon to her . . . from demanding Simon to strip for him, then directing Simon to undress him and jerk a load onto Allen's cock before licking it off and draining Allen's balls for the first time. Marilyn had heard enough and was squirming fiercely in the bed; ultimately giving up her struggle and mounting Allen and grinding her dripping cunt on his cock until she exploded and flooded his cock and balls with a blast of her pussy nectar; soon followed by a blast of Allen's cum deep in her cunt.

As she rolled onto the bed beside Allen, "So how soon can I join the two of you? I need to make sure that Simon has a proper cock for our lovely daughter."

Simon went home in a daze, trying to wrap his mind around what had happened today. He managed to avoid his family on his way through the house and up to his bedroom, and as he settled back beneath the covers, he realized he could finally come to terms with something he'd been in denial about for far too long.

"I'm gay," he whispered at the ceiling, grinning widely.

As much as he'd cum today, the excitement of the day still had him hot and bothered. He couldn't seem to relax, at least not until he'd dealt with his rapidly hardening dick and the stirring in his tight balls. He kicked off his covers and reached for the lotion he kept in a bedside drawer. Sighing, he gave himself a long, slow stroke session, picturing everything that had happened with Mr. Dalton, and everything else that might still happen.

His ass was twitching with need, remembering the sensation of the plug inside him. He turned over, shoving a pillow beneath him, and reached back, pressing two lotion-slick fingers to his tight hole and pressing inside. He humped his pillow hard and fast while finger fucking himself, imagining a hard cock ramming up into him.

"Oh yes sir... yes sir...," he panted, and added a third finger. "Fuckmefuckmefuckme..."

He didn't want to make a mess of his pillow, but he couldn't stop now. He pressed his face into the mattress to muffle his moans as a flood of heat spilled over his pillowcase and lower belly.

He had a feeling he wasn't going to need porn fantasies for a while.

"You do know how to fuck, don't you, Mrs. Dalton!", Allen teased his wife as they lay in their bed. Hearing the details of his "fun" with Simon made her extremely aroused and always kept their personal sex life highly charged. Marilyn had her own 'group' of friends that met together for some 'girl play' and she kept Allen well aware of those activities too.

But, not, she wanted to close look at Simon and what he was bringing to their family, to their Alyssa, who was as prudish and conservative as they were 'wild'.

"I'm pretty sure that Simon doesn't have a desire for pussy in his body; however, if I invite him over again tomorrow afternoon, you are more than welcome to join us and observe. What do you think about that?"

Simon awoke slightly sore, having fallen asleep in an awkward posture with his cheek against the mattress and his pillow still propped under his hips. He rolled over with a groan, last night's mess crusting his pillow, his stomach, and his genitals. He was rock hard with morning wood, having dreamed all night of Mr. Dalton and his study. This new discovery had made him insatiable, and after changing his pillowcase, he hurried to the shower for a self-love session to kick off his day.

Simon generally failed to appreciate the privilege he'd grown up in, always worried about ending up, or at least being perceived as one of these spoiled trust fund affluenza kids, but right now he was incredibly grateful to have his own private bathroom. He didn't have the guts to own any sex toys, as he worried the housekeeper might be a spy for his dad and tattle on him if she found anything questionable, but he found a hairbrush in a drawer with a handle that looked just the right size. In the shower, he greased himself up with conditioner and jerked himself off while inserting the brush handle carefully up his ass. It took him very little time to spew his morning load all over the shower wall, biting his tongue to keep from crying out.

He was keyed up all day in class, checking his phone frequently in hopes of hearing from Mr. Dalton.

After sitting through a couple of conference calls that took most of the morning, Allen took a break around noon. He contacted a couple of his "mature" fuck buddies and brought them up to date on his activities, without revealing Simon's name; they tentatively planned on a meeting of the 'club' in a few days . . . 3 hard cocks for Simon to drain, and maybe his initiation in having his ass fucked.

After a bit of lunch and another chat with Marilyn, who definitely wanted to see what Simon was carrying between his thighs, Allen sent him a text.

"How about another tennis lesson this afternoon. Mrs. Dalton wants to observe your stroke and see if you have what it takes to join our family. If you can make it today, wear a pair of shorts and the tightest, most revealing underpants you own."

Simon felt the phone buzz in his pocket while he was in class, and carefully pulled it out to read the text, his heart pounding.

Mrs. Dalton...? Just how dirty was this family?! The idea of Alyssa's mom being involved freaked him right out, yet somehow didn't take away from his arousal and excitement. As long as Mr. Dalton didn't make him touch her, he could definitely see the situation being rather sexy, in a totally wrong sort of way.

Did Alyssa have any idea...?

He quickly texted back: I'll be there!!

After school, Simon dressed similarly to yesterday, with the only pair of underwear he had that were sluttier than yesterday's - low rise micro briefs that were a few years old, and a bit see-through. Half aroused all the way, Simon made his way over and, as before, went around to the back door and let himself in, heart thumping wildly. He had no idea what this afternoon had in store, but he had every intention of satisfying Mr. Dalton.

Allen and Marilyn were in the study when Simon arrived; Allen behind his desk and Marilyn in a side chair wearing a flowing dressing gown. Simon could only guess where this was all headed. Allen looked up as Simon entered the study, "Close the door and lock it behind you, Simon."[

Waiting for him to do as instructed, Allen stepped from his desk and walked around to stand beside his wife. Allen, while wearing a neat button down shirt was naked from the waist down, his cock already beginning to stiffen. Marilyn reached over to caress his bare ass and wrap her fingers around his shaft. "Do you find this cock as exciting as I do Simon?"

Not waiting for an answer, Allen turned back to Simon, "Strip down to your underwear, Simon. Marilyn would like to see how well you fill it out."

Simon felt as taut as a coiled spring as he locked the door and turned to face the couple, taking in their attire and postures. He prayed that he wasn't in over his head.

Mrs. Dalton's question made his throat go dry, but it was impossible to miss how aroused he was. All he could manage was a vague nod before proceeding to slowly strip, piece by piece, his eyes locked on Mr. Dalton's cock.

His shoes, socks, shirt, and finally his shorts went into the box next to the door. He took a step closer to the couple, standing with an odd mixture of dignity and nervousness, in just his tiny micro briefs, with his rigid erection straining at the inadequate fabric.

"Sir... ma'am," he whispered.

Marilyn looked up at Allen, her fingers lightly caressing his balls as they hung below his shaft, "Allen, I do believe Simon is quite uncomfortable in those tiny briefs. Would if be ok if he stepped out of them?"

Allen looked down at his wife, "Absolutely, love. Simon, please rid yourself of those briefs. I do believe that Mrs. Dalton can handle the view of your delightful cock."

As your briefs land in the box, "Do you approve of Simon's young cock, love?" After a slight nod of her head, "OK, Simon, come closer. On your knees. I do believe that Mrs. Dalton is expecting a demonstration of your cock sucking abilities. Is that right, Marilyn?"

Simon's eyes went very wide. Was he dreaming? Was this really happening? He wasn't sure why his girlfriend's mom needed to be assured of his cocksucking ability, but he figured it was mainly some fetish they had between them. He decided he didn't mind one bit being a part of it. Nor was he likely to mind becoming a part of this family, should things go that far. He was a bit scared Mrs. Dalton might take off her robe and she'd find out in a hurry just how gay he was, but for the moment he found it kind of exciting that she might be turned on by this.

As he got on his knees he thought of his own father, who obviously hadn't the slightest clue what really went on in the homes of families he respected... nor in the life of his own son. Dad's head would explode.

Blushing, Simon opened his mouth and wrapped his lips around Mr. Dalton's hefty organ, his eyes glancing between the two of them, just to remind himself how depraved this was. His own rigid cock was almost dripping.

As Simon knelt before him, Allen could see the smile on Marilyn's face; she was going to enjoy this. As fantastic as their own sex life was, when they included other people, it got even better. Tonight would be another epic episode in the Dalton marital bed.

Simon did not hesitate and took Allen's cock into this mouth, quickly bring it to full erection. As he began to grow in Simon's mouth, Allen could feel his arousal increasing and could hear Marilyn's breathing becoming more rapid . . . she was indeed enjoying this and would repay him later for the performance.

Looking down at Simon, Allen decided to add a bit more to the show for Marilyn.

"Simon, please stop for a moment. I think you know what I want you to do before you make me cum?" Turning to his wife, who has a questioning look on her face, "Simon is going to masturbate until he shoots his load all over my cock, then he will clean his load off my cock as he continues sucking me to orgasm. I think you will enjoy his performance."

Simon leaned back, sliding his lips off of Mr. Dalton's cock with a light, wet smacking noise, and considered the instruction he was being given. He looked back and forth between the couple, ever more curious about their relationship. But could he actually jerk himself off in front of a woman? A mom? His girlfriend's mom?

He stood up slowly and took his cock in hand, looking Mr. Dalton in the eyes, practically smitten, and then straight down at his big, hard dadcock. Yes... he could definitely do this.

Breathing hard, Simon jerked himself with long, rhythmic strokes that steadily increased in speed. He was producing plenty of precum, and used it to lube himself up. He wanted to ask Mr. Dalton for something to put up his ass, but he wasn't sure he had the privilege of making requests. As the heat in his body rose, and he began to softly moan, he decided he couldn't resist - he hastily popped two fingers into his mouth to wet them with saliva, and reached back to press them against his hungry pink pucker. He was breathing raggedly now, pointing his cock squarely at Mr. Dalton's as he approached his climax.

Looking down as Simon wet his fingers and reached back for his tight pucker; looking over at Marilyn, "Baby, why don't you go get the butt plug out of my desk drawer and the lube. I think Simon needs it right now."

As she goes to my desk, I step back for a moment, "Simon, lean over the chair." As Mrs. Dalton returns, I can see by the look in her eyes that she is aroused; her cunt has to be dripping wet by now. I know that Simon is not at all interested in contact with Marilyn, but I can't keep everything from her.

Pointing to the butt plug and Simon's ass, she nods, coats the plug with a generous glob of lube, and slowly inserts it into Simon's tight rosebud, her hand resting his lower back for leverage.

"That's it, Simon, you little slut. Now you can finish jerking your hard cock all over mine for Mrs. Dalton's pleasure."

As he begins stroking again, Marilyn leans against me, her fingers buried between her thighs . . . she will probably cum herself when Simon coats my cock with his cum.

Simon leaned obediently over the chair, presenting his ass, and shut his eyes as the plug was carefully inserted. He sighed happily, and a lot more precum began to flow.

"Thank you, ma'am," he said shakily, his eyes gleaming as he opened them again and gazed in Mr. Dalton's direction. This was so surreal, and so wrong. Part of him wished his obsessively prudish parents could see this. Part of him wanted to go absolutely hog wild, and rub it right in his dad's face.

Simon was sure by this point he'd never been so aroused. Once more he used his own precum to lube himself up, and his hand made wet slapping noises as he started up again, his ass throbbing warmly. He took very little time now to get himself to the edge, and he couldn't hold back even if he wanted to. Gazing lustfully at Mr. Dalton's hard organ, he groaned loudly and began to gush prodigious amounts of his hot young seed all over the older man's dick and balls.

The expression on his face was dreamy and practically drugged. Drunk on the orgiastic rush of the situation, he fell to his knees and almost immediately began to devour the huge mess he'd made, licking and slurping like a starving pup with a meaty bone.