Give And Take Roommates · Part 2 (2/3)
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As Valerie was about to respond, Brad walked in and whistled at the beautiful sight of Valerie's ass in the air. Her dress was too short to actually cover it in her present condition. "Ready or not here I come," exclaimed Brad.
Myron halted Brad as he tried to head towards Valerie. Myron jestered to Brad to leave the room for a second. Brad headed out and Myron punched his ass along the way causing Brad to jump and skitter forward. As they reached the living room, Brad stopped and turned around. Myron was on his heels and kissed him on the lips before he could say anything. Brad was momentarily taken by surprise but returned the kiss. They wrap their arms around each with Brad's partially stiffened cock rubbing up against Myron.
Myron broke the kiss but not the embrace and said, "For many years I have wanted to do this. Even a little jealousy has crept up knowing all those you have slept with including the guys. I was never jealous of you and Val but I did feel a little empty being left out. I love you and I love her. Tonight we want to show our appreciation to each other. I want you to understand we are not your normal hookups. We care and we want you to not only enjoy but to show your appreciation as well. Do you understand me, cowboy?" Brad nodded as Myron slid down gripping Brad's semi erect member.
"There is a lot of vulnerability going on. Starting with you as you are silent compared to normal. I know she is very vulnerable as well. She wants more than anything to make us both happy. She is going to do her best to enjoy this and make this special as I hope we all do but she is scared and nervous as well." Myron stroked Brad slowly, getting him worked up. "Be slow and gentle at first. Build her up, play with other parts of her to distract her from what is happening then wait for her when she wants more from you. I will let you two start first so she is comfortable before I join in." At that, Myron wrapped his lips around Brad's shaft and began sucking.
Brad groaned, "You know I love you both even if I am a bit selfish." Brad grunted before continuing, "Man if I knew you could suck cock so well, I would have asked earlier and saved myself some of those embarrassing times."
Myron bobbed down as far as he could on Brad's cock before popping it out. Myron smiled and said, "Looks like you are ready, cowboy. I wouldn't mind if you help me get ready."
Brad smiled and answered, "Sure thing, sis. I should probably get an idea of what I am going to take." As Myron stood, Brad pulled down his pants since he was already shirtless. He worked his way to remove his boxers, Brad shouted, "Holy shit! You're gonna be thick as fuck. Never had one that thick before."
Myron feigned surprise, "Your sis, too big for you big boy?" He laughed at the shock on Brad's face as he began to touch it with his hand. "Don't be shy, it hasn't bitten anyone yet. Not even Val during her hand job earlier. She desperately wants me to fill her up so if little Val is willing, a big boy like you should take it no problem. Come on, cowboy, have a taste. Val won't be going anywhere until we release her."
Brad dropped to his knees and began stroking Myron's shaft.
"Are you and Val a thing?" Brad asked before taking a quick lick before encircling the Myron's shaft with his lips. He slowly began working as Myron stiffened in arousal.
Myron responded, "Dear God no. Don't get me wrong, I love her more than anyone. Only you are equal to her. But I don't have the same attraction to her as I do you and other guys. It is not for a lack of trying. She badly wants to be attractive to me. I have spent years helping her bondage fantasies because she trusts me and you are not interested. But I never once took advantage though I am sure she has silently hoped. Today was the first time she saw me naked and was allowed to touch it for the first time. She wishes she was in your position now. But it was an incentive to get her more motivated for this tonight."
Brad gave one last thrust down Myron's shaft before popping it out. "So you manipulated this?," Brad asked.
Myron responded, "I guess so, cowboy. But we all are getting something we have waited a long time for and maybe it will lead to more in the future. I think I am ready, don't want to be spent before I fully work your ass," as he let go of Brad's head. "Go take her anal virginity. Make her beg for it. Deep down she craves it and start gently." Brad got to his feet and nodded before heading to the bedroom.
Valerie for her part was curious to where they went and why they hadn't started. Her mind raced at all the things going on, feeding the fear and excitement. The way she faced, she couldn't see the door. When Brad swatted her exposed ass, she moaned with a bit of pleasure while shouting out, "What the fuck!"
Brad ran his fingers along her inner thigh collecting some of her leaked juices. Valerie shivered and begged, "Please don't. I am so on edge and I don't want to cum yet."
Brad licked then sucked on his fingers right in front of her. "Why not?" he asked.
"I am here to be your anal whore and I figure if I am so worked up that I can likely cum and desire doing it more," responded Valerie.
"Is this what you want or are you doing it for Myron and his scheme?" Brad asked.
"For fuck's sake, Brad. You just licked the juices running down my leg. You know I am horny as fuck. Am I scared? Yes. Nervous? Very much so. Do I want this? More than anything right. Yeah Myron got it started but this isn't anything I didn't want deep down. He gave me a nudge. You have wanted this for years and it is right here in front of you. Take me like I know you want ever since you walked into the door as well as most of your life. I am not tied up because I am forcing myself to stay and do it. I am tied up because it calms me, arouses me, and generally makes me feel great. Actually I have been tied up much of the day which has helped me get into this mood. So Brad be yourself and use me like the filthy anal whore you desire. Make me want it now and in the future. Please Brad, I want your cock buried in my ass. Pound it until you fill me with your seed. Please!"
Brad stuck a finger into Valerie's mouth and began moving in back and forth as her lips wrapped around and began sucking it. He pet her while finger fucking her mouth. "You made me wait years for this moment. Now I am going to make you wait in your horny desperate state, my soon to be anal whore. Actually I think I am going to fuck Myron first, right here in front of you so you can see the bliss of being a true anal whore," as Brad pulled his finger out her mouth. Myron on the other side is grinning ear to ear.
Valerie screamed, "No please fuck me now. I want to be your anal whore right now." She struggled to break her bonds, whimpered and began to cry.
Brad stood up as Myron came over. Myron bent over near Valerie looking her in the face. Brad had taken a moment to grab some lube and applied it as he now stood behind Myron and his toned dark exposed ass. Brad looked at Valerie and told her, "We will get to you soon enough, after all you didn't want it for years and Myron has waited patiently for years for this and it is his idea. So I am going to reward him first while you learn."
Brad pressed the tip up against Myron's sphincter, Myron quickly tried to relax and he felt the pressure start to push. Valerie stared into Myron's eyes and watched his anticipation with her own anticipation. Myron let out a slight purr as Brad broke in and Valerie saw Myron's face enjoying every bit of the brief encounter so far. Brad slowly worked his way in and began slowly pumping in and out. Myron cried out, "Fuck yes, ride me cowboy."
Brad began to pick up the pace and Valerie could see the pure joy in Myron's face. Myron looked at her and smiled, "You will get your turn honey. After I'm a used bronco, first."
Valerie squirmed to try and get any friction as she was so horny and no longer wanted to wait. There is little to no movement that would help her as she groaned in frustration. She thought Brad would come in and just take her immediately but that didn't happen and now he was torturing her by making her wait with no way to get away or relieve herself. She just wanted their touch from either one of them. She was no longer scared or nervous, she was down right frustrated and horny as hell. She whimpered, "Please fuck me. Touch me. Anything besides this."
Brad and Myron both smiled at her but neither gave into her desire. Brad was riding Myron pretty hard, enough to start shaking the bed. Myron was moaning and crying out sounds of pleasure. Brad was panting louder before he shouted out, "I am going to cum in your ass, sis."
Myron shouted, "Fucking finally. Fill me up, cowboy. I have waited far too long for this. I need it all deep in there. Don't let me down and fill me until I can't take anymore." As Brad shot his load deep inside Myron, Myron shouted out, "Oh my glorious fuck hole!"
Myron twitched and shuddered as each spurt filled him up more. Myron's eyes rolled as he gripped at the blanket in ecstasy. Valerie looked on with a smile and a small hint of jealousy. She wanted her turn.
Brad slumped down on top of Myron for a moment. They thanked each other and kissed passionately. Brad announced, "I am done, see you guys in the morning."
Valerie flipped out bouncing around in her bounds. Her face was red and fraught with anger. Before long she blurted out, "Fuck you Brad, you promised. You better get over here and fuck me. I offered you my ass that you wanted for years. Don't you dare walk away or you will never get another chance."
Brad smiled at her, "I don't need your ass when I can have Myron's any time." Myron snorted. "Also you can't do anything about it anyways. You are Myron's little bondage bitch and you can't go anywhere at the moment." Valerie looked at both men in horror.
Myron chimed in, "Maybe if you ask nicely, we will let you clean us up. If you do a good enough job he may get hard and take you as promised. Though I am guessing you won't get the load size I have inside of me. Plus whether he wants to or not, I am going to get his ass tonight as promised."
Valerie began begging, "Please Brad. Let me work on getting you hard again. While I am less excited about what your cock is covered in, I am desperate. Please let me try at least."
Brad motioned to Myron and they both went to a different side of Valerie and lifted her before placing face at the end of the bed. Valerie began to say something but Brad shoved his flaccid, dirty cock in her mouth. "Clean it well, especially if you want it in your ass next." Valerie gagged initially but Brad was holding her head in place.
Tears of frustration were still coming down. Part of her wanted to be let go and go to her room and finish herself, but the other part of her was begging for more. She had dreamed of this and wanted it more if she really thought about it. Mostly it turned her on so much more and made her more desperate. It didn't stop her tears of frustration but she was willing to endure the two men she loved.
Myron hadn't expected the change up that Brad threw but he wasn't going to complain. He was hoping for it at some point in the evening, likely after the planned encounter. He was a bit concerned for Valerie but she hadn't actually asked to stop, if anything she was just really horny and in need of release. She's a tough little girl and he was proud of her resilience.
Brad enjoyed his changing of plans. They had manipulated him for years when they wanted, especially Val. Getting her ass had been a dream of his for as long as he remembered and now he was making her wait. Val may never be the prettiest girl, but she was always there and he probably took her for granted. Well she was prettier than Myron but he made a good sister as well. He ignored Myron way too much and he seemed pleasantly surprised when he was fucked first knowing how much Val meant. They take care of him even when he doesn't deserve it. Brad let go of Valerie's head and she gasped for air. He let her finish licking him over on her own before backing away.
Valerie clearly pouted, "You're not hard yet."
Myron chimed in, "Brad needs a longer break. We can offer you a chance at anal release to help you out but as usual it comes with a cost. Maybe you will like it anyway."
Valerie pleaded, "Anything."
Myron asked Brad to go finish cleaning up first as he told Valerie his offer, "Brad will finger you and work on stretching your ass before he fully penetrates you. You will be allowed to cum since he will be penetrating your ass." Valerie looked relieved until Myron started again, "But you have to play used cum receptacle and cock and ass cleaner well except cleaning your own ass since you can't reach. I will even encourage him to feed you your own juices if you do well. How desperate are you little girl? Do you want to lick my ass now because tonight might be your only chance."
Valerie frowned and was conflicted. He kept making these really tough offers to get her to do things she wouldn't normally do or hadn't thought of. It was one thing to get ass fucked but she had no desire to do rim jobs and clean out the used cum. She knew a number of people do it. But she was pretty desperate and did say she would do anything and didn't want to back down. She thought Myron was secretly enjoying this. Some day she would find a way to use this against her big sis. She started to smile in spite of her reluctance. Enjoy this she told herself.
Valerie responded, "You have a deal. You like to make these things tough but one day it will backfire or I will get an opportunity to make a deal with you."
Myron laughed at her as he flipped her over onto her back. Her knees were still up against her chest as her arms were forced straight while still tied to her ankles. Valerie muttered something about not being a sack of potatoes. Myron straddled her face lining up his ass so her tongue could reach.
Brad walked in, "Did anyone think to record this, cause I want to record this moment." Brad popped out a video camera and Myron choked. Valerie was shifting and it was clear she didn't want to be recorded.
Myron looked at the camera, "Mr. Limpy, she is waiting for you to finger her ass and stretch it out until you know, you can get up again."
"Fuck you sis. I dropped a big load in your ass first instead of hers and this is how you repay me." Brad moved onto the bed anyway, camera in hand.
Myron replied, "No one agreed to be filmed and she is quite upset and making this rim job less pleasant."
Myron shifted as Valerie was trying to yell, cutting her off, "Try to relax and enjoy cause you're about to feel some pressure." Valerie tensed when she felt Brad reach her sphincter. Myron once again told her, "Relax honey or it will hurt more."
Brad slowly got his finger in and began fucking her slowly. The tension lessened slightly. Valerie was finding that rim jobs are not so bad but being a receptacle for used cum was not as pleasant. Brad's finger had surprised her but once the initial shock wore off it started feeling reasonably good. If he would go faster she might cum soon but Myron wouldn't let her talk while he drained Brad's used cum into her mouth.
Brad kept the camera close as he used his finger in Valerie's ass. He was setting up to add the second without warning. He pulled out the finger and then placed two when he reentered. Valerie squealed and then moaned within a few seconds of adjusting. A minute later, Valerie was trying to fuck his fingers in hopes of getting an orgasm. She noticed that the cum stopped coming from Myron's ass but he made no move to get off her face. Valerie moaned louder and screamed as a fountain of cum splashes into Brad's camera.
Brad shockingly said, "Oh she's a squirter, I didn't know. Fuck she got it all over my camera. At least that should be quite the video to post." He laughed maniacally, having stopped fingering her after she squirted.
At this point, Myron had gotten off of Valerie's face. She was breathing heavily trying to catch her breath and calm herself as her body twitches after her first anal orgasm. Finally after a minute she spoke, "First off asshole, you wouldn't know I was a squirter cause you have never made me cum before."
Brad interjected, "Told you we should do anal."
Valerie rolled her eyes, "Fuck you. Next time you want sex, I'm going to use a very large strap on your ass until you cum."
"Oh, threats from my tiny little sis. Trying to make up for your lack of size?" He sarcastically commented.
Valerie sneered, "I don't make threats, only promises. Much like if that video gets posted, I will bite your dick off."
"You're kind like a Chihuahua, all bark and no bite." Myron groaned and Valerie snarled ready to attack. "So how are you going to stop me if I post it now." Valerie began to buck and scream profanities at the top of lungs trying to get to Brad but looking more like a turtle stuck on its back.
Myron interjected, "Enough Brad. This is supposed to be fun and now you are being cruel for no good reason." He stroked Valerie's head trying to calm her down. He continued, "She trusts us and that's why she agreed to this. Don't be a douche bag and ruin it before we even finish."
"You can't even see her face. You sat on her face for the parts it would have shown up in," Brad exclaimed.
"Not the point. You didn't ask hers or my permission. Trust man. We trust you, don't mess that up. She is in an emotionally vulnerable state especially after her orgasm. Even if they don't see her face, she is pretty unique in her physique that people will figure it out. So let it go and talk to her later about it. Let's finish the night on a good note." Myron retorted. Brad agreed and Myron asked Valerie if she was ok and she nodded. "I am betting that orgasm helped?"
Valerie shuddered, "Don't think I have ever had one that strong before. It was intense."
Myron got up and walked over to Brad and kissed him while fondling Brad's cock. He whispered into Brad's ear, "Time to take her anal virginity and for me to get to fill your ass." Brad seemed calmer as Myron got down and started licking Brad's cock. After a couple of strokes and sucks, Brad came to life down there again.
Myron walked over to Valerie, "Are you ready to be his anal whore and lose your virginity? You may get another orgasm like that if you still have enough pent up energy." Valerie shuddered again and licked her lips before nodding. "Then beg properly for it like you have all night, like a good naughty little girl."
She looked up and smiled at Myron. It offended her to be called that all her life but since earlier in the afternoon when their relationship changed, she knew it was now who she will always be for her big sister. She looked over to Brad, "You can be a huge fucking dick at times. But tonight I want that big cock of yours to finish what you started and make me your anal whore. Please take my virginity that you have wanted to take forever. Make me scream in ecstasy. Try to split me in two as you think I am so dainty. Most importantly, please fucking make me cum like that again and I will be begging you to anal fuck me all the time. Take me now. Please!"
Brad came over without a word and flipped the turtle known as Valerie over and scooted her ass to the edge of the bed. Myron dumped some lube on Valerie's ass, while Brad took care of his cock. He finally says, "You want me to start soft and easy or should I see if I can break you in half?"
Valerie laughed at him, "You wish you could…" Brad went from zero to full in one quick stroke. Valerie screamed out, "Holy fuck!" Her body shook and gasped.
Brad replied, "Too much for you already?"
Valerie quipped back, "You think one stroke is going to break me, asshole. Or do you not have the stamina to try to break me? Unless your real goal is to make me an anal whore first before you try to break me. Either way, you should probably start fucking me before you get too excited."
Brad pulled out and slammed back in. You could hear the two bodies slapping together. Valerie's face was driven into the bed, her hands were clenched tight into balls and her toes curled. She hoped he couldn't hear her gasps but at least he couldn't see her tears. She knew he just wanted to hear her give in and ask for a more gentle fuck but she challenged him. Relax, breathe, and focus on pleasant things. He will not break me, she thought.
Brad continued doing it for another dozen or so thrusts before shorter but still powerful thrusts. Valerie gave a few squeals and groans but endured. Brad finally spoke up, "Are you sure you're a virgin back here. Beyond being super tight, you have taken it better than a pro. I guess bronco busting time is over." He slowed his pace to smoother more rhythmic strokes.
Valerie's face was still buried in the bed but her crying and nerves were starting to calm down. Valerie felt a hand come in from the side under her arm and reached the top of her dress. The dress was pulled down just enough to expose one of her little nearly flat breast. Fingers tweak her nipple and her head shot up, she sniffled, "Fucker!"
Brad laughed, "She's alive and yes, I'm fucking you. Thank you."
He bent forward to tweak her nipple again when Myron joined in and thrust his cock straight into Brad with about as much mercy as Brad gave Valerie. In the process, Brad slammed deep into Valerie breaking his rhythm and causing her to gasp. Myron knew Valerie pretty much asked for it but Brad needed to be taken down a peg himself. Brad screamed, "Holy fuck!"
Myron laughed from behind, "The cowboy couldn't break his steed so now he gets Brokeback Mountain."
Valerie snorted as Brad groaned. Myron continued thrusting into Brad who thrust deeper into Valerie. Squeals, moans, and groans from all three permeated the room. The anal train began to pick up rhythm and the three of them seemed to be enjoying themselves.
Brad was in a pleasant conundrum. He was living his dream of finally fucking Valerie's ass. His ass was also completely filled with Myron's rather large and thick cock. Pleasure from two sources is great but it's hard to focus and fully enjoy both. For the moment, his prostate was well massaged and really turning him on and making him want to cum soon. He really wanted to make Valerie cum again and get more opportunities to use her ass in the future. Myron just felt so good. He just couldn't complain. Then again he and Myron were going to be spending more time together as well. Brad could only think of how awesome this felt. He was glad these two set this up.
Myron was kissing the back of Brad's neck just taking in the pleasure of finally fulfilling his deepest desire. Today he decided to take some initiative to get more of what he wanted. He realized he would get many opportunities with her as her bondage addiction was just too great for her to stop. He would make sure she was well taken care of as he always had but this added dimension gave her fantasies a purpose for him. Though he was still unsure what to think about his relationship with her. She was very much attracted to and wanted him, but he wasn't and never had the same attraction.
For the most part on a regular basis she wasn't all that feminine and she pointed out he had been with much more feminine guys. He had allowed her to see and touch me in ways she had only dreamed of yet he was unsure if he wanted to let it develop further. He didn't want to be cruel and lead her on that way. He felt he really needed to think about it.
Valerie's rough start, which was her own fault letting her temper get in the way, had turned into a much more pleasurable experience. It hurt so much and while she was not much for a lot of pain, she wanted to prove a point to Brad. He wouldn't break her, especially not with his dick. She was always trying to prove her toughness not only to them but to everyone. It was part of her insecurity about her size. While she knew Brad wouldn't break her, Myron's changes and intimate knowledge of her strengths and weaknesses was another matter. A small part was glad he wasn't interested in her. But she would be lying to herself if she didn't wish he was interested and tried to break her.
