Learning to Surrender Pt. 06

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Rick spent the next day wondering what would come next. He realized he was never going to be able to anticipate such an experienced older man like Jack. But he did find himself hoping that he was the best Jack ever had. What if Jack still saw other personals? What if he tried out some other young partners for sex? Rick couldn’t blame him – the man was so virile he probably needed draining all the time. But the thought of being replaced by someone more eager or more open scared him. What if someone else was even more submissive? He didn’t want Jack to think of anyone else let alone enjoy someone else’s body more. He wanted to be, for Jack, the number one in bed. He decided to try harder to do whatever Jack wanted and be whatever he wanted as well. And then he got the text.

“Clear your entire evening this Saturday. I want to show you off. You’ll be home very late. My house, 4PM.”

Rick was as excited as a schoolgirl when Saturday came. Soon he was parking in Jack’s driveway. He put on the choker, the sign of Jack’s property, and went into the house. Jack was sitting in the kitchen watching Netflix on his laptop. He was fully nude and had an enormous erection. There was the foam pad below the table in front of Jack’s feet.

“Rachel, I needed you all day. Get over here and under the table. Do your duty. Come be a good girl…”

Rick got under that table, kneeled on the rug, and used both hands to cup and caress the engorged testicles. They were so hot and full, clearly needing release into his body. He hungrily swallowed the thick manhood and began to worship his man, his head bumping against the table from time to time. Jack started snorting and grunting like a bull as he kept trying to watch his show. He smiled knowing that the young boy was getting more and more talented, especially at fondling his balls. The young slender fingers knew how to grab hard and how to massage softly, always dancing the fingertips to maximize his sounds of pleasure. Of course the tongue and suction on his shaft helped as well. He thought he’d be able to finish the episode but he struggled to keep himself level with his hands on the table as the boy serviced him. Soon he couldn’t hold it any longer and decided to let the boy have it. He growled and shook the table as he shot rope after rope of hot semen into Rick’s mouth. Rick was in bliss as he again successfully did his duty and drank in yet another enormous load into his body.

“Come on out and take a seat.”

Rick did as he was told.

“Tonight, we’re going to get dinner and drinks at a lounge I like. It’s a place for older men to bring young sex partners or to find new ones.” Rick shuddered at the idea of being out in the real public. “Don’t worry, its in the next town so no one will recognize you.”

“Are… you… going to share me there?”

“No, I don’t plan on it. Why?”

“No, nothing… I just want to please you… and only you…”

“I know you do. That is why I’m impressed with how much you submit to me.”

“It does really scare me when you surprise me with these ideas but… I like forcing myself to trust you…”

“I’m glad to hear that. Because I will keep pushing your boundaries and comfort zone ok?”

“Yes… “

“But I will always keep you safe.”


“Look at me Rachel. What is on your mind?”

“I just… this sounds pathetic… but I want to be your only… girl.”

“Hah, that is cute. Listen, everyone earns the right to time in my bed. Everyone has to earn my sperm. So far, you’ve done extremely well…”

“That’s good to hear…”

“But i see your concern. So how about this. As long as you fulfill my deepest needs and desires and show me you can totally surrender to me and my needs, I won’t take another into my bed. But… if you hesitate or I stop getting the feeling that you’re not trying… I will be more tempted. And if you really prove to be one of a kind, I’m going to make you my wife.”

That stunned Rick to hear… and scared him. What was a wife?

“What do you mean?”

“It mean’s you will live with me and take your place in my bed and dedicate your life to my needs. You will take every drop of my sperm forever.”

“Oh.. Ok…” The thought was crazy. What about his family? He already had a wife. How could he become someone else’s? That would turn his life upside down… but still the thought was thrilling.

“Go to the bathroom and prepare yourself. I have a dress and shoes you’ll be wearing for me tonight Rachel as well as the smallest thong I had for my boys.”

Rick went to the bathroom. He showered and shaved and cleaned himself thoroughly. After putting lotion on all of his skin, especially his ass and legs, he held up the dress. It was a thin almost sheer that left very little to the imagination. He had never put on a dress before. As he stepped into it and pulled it up with the straps on his shoulders, he was shocked to find how short it was. It barely covered the bottom gaziantep escortlar of his ass. When he bent over even slightly in the mirror, anyone could see. He looked at the thong and it really was the thinnest thing he had ever seen, barely able to cover his already dripping penis. The shoes were clear heels with straps. It was clear he would be shown off tonight.

When he walked out to the living room carefully he saw Jack look at him like a starved wolf. Rick’s cautious steps and balancing act made his hips sway. Jack was wearing a linen button up shirt and linen pants. He grabbed the younger boy and kissed him hungrily, roaming his hands up and down the soft dress grabbing wherever he pleased.

“You’re making me soak these tiny panties…”

“It’s ok Rachel, this is all mine anyways.”

Rick ran his hands up and down his man’s hard chest and shoulders and then dropped his hands to hold his man’s jewels. He almost gasped into Jack’s mouth when he realized that Jack wasn’t wearing anything under his linen pants. Jack grunted into the boy’s mouth as his massive testicles got massaged and was tempted to cancel the night and take have his ass on the spot. But no, the plan had to be completed. But he did need to release…

“Rachel… we have to go… but I need to cum. Show me how quickly you can make me cum… but here’s the challenge. No ass. No mouth. Go… hurry… because I just called the Uber.”

Rick undid the drawstring of the linen pants and let them fall to the floor. He unbuttoned the linen shirt and had his man step out of his clothes and stand in front of the coffee table. He had Jack stand feet slightly apart and kneeled beside him. He reach his right hand between the legs from behind and grabbed hold of the hot swollen testicles. His left grabbed the shaft. And he went to work using every bit of attention to the tensing man’s body as he stroked and fondled his man’s glorious genitals. Every breath, grunt, twitch, shudder of his man, he used to learn. He felt the balls tensing and shaft thickening. Jack even leaned down and steadied himself with his hand on Rick’s head.

“Uggghhh… Rachel, baby… I’m… gonna…”

Rick already knew from his man’s body signals that an enormous load was coming and it needed a place to be received. He moved in front of Jack, letting go of the growingly tense balls momentarily and then resumed his massage from the front. He aimed the engorged manhood as best as he could, closed his eyes, and opened his mouth was wide as he could.

Seeing Rick so eager to receive his seed, Jack couldn’t hold off any longer. Seconds later, he grunted loudly as he unleashed jet after jet of thick white semen out of his testicles. The boy’s tongue, teeth, upper lip and nose were covered and with thick jets of warm semen. Rick smiled as he swallowed, licking what got in his lips and swallowing every drop he had milked. Rick was so proud that Jack was so relieved. Jack smiled as his young lover helped him get his clothes back on.

“Rachel, bend over, hands on the sofa.”

Rick wondered if he was going to be mounted. Impossible. He had just emptied those balls. But he still was glad to assume the position. Urgent hands pulled his thong string to the left. He felt the cold lubricant be pressed into him and squeezed. He felt it coat his insides. He closed his eyes for the fingering that was surely to come. But instead, he felt a lubricated toy slide up into him. He was disappointed.

“Ok let’s go, the Uber is here.”

Rick carefully walked out wondering if the neighbors would recognize him in a dress. Jack noticed it was the first time for the boy in a short dress and heels. He put his arm around Rick to steady him until he got in the car. Rick realized how talented girls really were in moving around without falling or flashing the world. As the car drove on, the driver made small talk. Jack didn’t seem to want to talk so Rick answered for them. He felt Jack’s hand go down the back of his dress, and roughly dig under his ass. Rick slightly lifted himself up to give his man better access. Jack’s fingers traced around the plug now deep inside the boy and any time Rick tried to talk, Jack would press the plug and push it, making it lean and move inside. It was so hard for Rick to keep talking. All he wanted to do was close his eyes and cry out in pleasure. He grew bolder and slid his small hands down Jack’s manly thighs and rested them on Jack’s manhood, slowly stroking the shaft, never forgetting to reach down and massage the balls now and then.

They arrived. It was a lounge in what looked like a warehouse area. Rick carefully got out and held onto Jack tight as they walked in past the bouncers. As they walked in, everyone seemed to know Jack. Everyone whistled and hooted at the young new sextoy Jack had come to show off. Everyone knew it was the Jack’s first time in a dress. Jack was known for converting straight boys for years. As the waiters cleaned up a corner table for them, a slower song came on. Jack pulled his boy out to the dance floor, pushed up the boy’s arms up around his neck, and grabbed him by the ass press against him as close as possible. They kissed and Rick forgot where he was. He didn’t care that he was in public wearing women’s clothes. He didn’t care he had a man’s tongue exploring his mouth or big hands grabbing and kneading his ass. He didn’t care that other men would see his bare bottom and likely could see how thin his thong was or the toy lodged in his ass. If Jack wanted to show off his girl, then he had every right to, Rick thought to himself.

Jack lifted the bottom of the dress completely and hungrily grabbed the bare cheeks. Rick didn’t care that everyone was guaranteed see his thong. Then Jack reached into his pocket and pressed a button on a wireless remote. Rick yelped as the plug inside him that had been resting against his prostate began to buzz and vibrate. His knees buckled as he held onto his man for dear life. He couldn’t think straight, just close his eyes and moan on the dance floor. Jack smiled as he looked around. Many regulars looked on in jealousy wishing they had a sex partner like his, lost in waves of pleasure. He turned it off leading to a desperate whimpering from Rick.

The two lovers went to sit down. As Jack ordered food and drinks, Rick was still in shock that he had a remote controlled vibrator in him.

“Want to see how strong it can get?” Rick could only nod. At the first level he was already in heaven, squirming in the booth. Jack clicked to level 2. Rick gripped the table and crossed his legs. Jack clicked again. Rick had to put his head on the table, teeth clenched, letting out a pretty loud squeal. When he felt it become even more intense he fell over onto Jack’s lap, babbling incoherently. Jack stopped as old acquaintances came by the table to talk. Rick was still delirious from the vibrator inside of him.

“Rachel dear, look up. See this man? He’s an old friend, older than me. He taught me how to seduce young straight men like yourself long time ago.”

“Oh… Ok…”

“He wants to dance with you. Is that ok?”

“Just dance?”

“Oh no, I just want him to have a feel for how lucky I am. I told him he’s not allowed to have you. Ok?”

“Ok Jack…”

“Go on now…”

Derek was already standing with his hand extended to lead Rick back onto the dance floor. He drew the boy in close to him and steadied him with his hand on the lower back. When they got out into the crowd, Derek pulled Rick close to him and began to sway with the music.

“Did Jack tell you who introduced him to the world of straight boys?”


“I did. I taught him all the tricks and tools of the trade many years ago… I thought I was a good hunter but Jack has turned out to be a far greater lover than I ever was in my day… as you probably already know.”

His hands slid down and rested just above the boy’s bottom. As the music continued and the dance floor became more and more crowded, Derek began to smell and lightly peck at Ricks face and neck, whispering how soft and wonderful his body was and how lucky Rick was to have found such a “girl.”

All of a sudden, Rick felt the vibrator lodged inside of him turn on. He panicked as his legs began to weaken and he was forced to lean more on Derek, possibly sending the wrong signal. Jack seemed like he was manipulating the controls according to the music, up and down, up and down, driving Rick into a trance like state with his eyes closed. Derek whispered something into his ear but before he could say he couldn’t hear a thing, Rick felt his face grabbed and a rough bearded kiss planted on his lips. He kept his mouth shut as he remembered what Jack said. His body was off limits to Derek. Should he run? At that moment, the vibrator jumped to the highest setting, setting fireworks off deep within him as his prostate took the brunt of the vibration. He couldn’t breath let alone stifle his moan and as he did, he felt Derek capitalize on the moment and shove his tongue roughly into the young boy’s mouth. Rick was in turmoil, worried that Jack would see him unable to move or resist this man. He let his tongue be ravaged by this new tongue and focused only on staying on his feet.

The vibrator inside of him of continued to put pressure on his prostate, undulating. Rick held onto Derek more and more, breathing through his nose, moaning into Derek’s mouth as the rough tongue dominated his mouth. Knowing the boy’s defenses were lowered, he grabbed his hair and pulled back, exposing Rick’s neck and chest, ravaging the sensitive and vulnerable region with his mouth and tongue. His hands wandered even further, his fingertips touching bare ass right below the hem of the dress. Derek then could feel the vibrations emanating from the boy’s core and he smiled knowing what Jack was doing from the booth. He pulled the boy’s face back and began to kiss Rick again even more hungrily and even more boldly began to trace his fingers along the thin thong string, down further and further, until he tapped the shaking vibrator. Rick knew his body was no longer his to control and even found himself kissing back. But when he felt fingers at his bottom tapping on the vibrator, he panicked, knowing he had to stop this.

“Why don’t we go back to a VIP lounge, Rachel.”

“I’m… not supposed to…”

“Jack he owes me alot from back in the day … You don’t think he’s priming you for me?”

Rick’s mind was on fire. He was told clearly not to share himself but why would Jack make him so defenseless with the vibrator? Derek began to step towards a curtain behind which he could find a place to plunder his friend’s well-trained boy, his left hand leading the way, clearing a path through couples, his right hand firmly grabbing and pushing the boy in the direction he wanted, all the while feeling the vibrations pulsing from the boy’s core. He smiled wickedly as bouncers he knew pulled back curtains. They had seem him lead boys back there hundreds of times. Rick could barely stand or open his eyes, but he knew the situation was getting dangerous.

“Rachel, step in here.” Rick was pushed into a dimly lit booth with a bead curtain for a door. Derek took a seat on the only chair and pulled his prize onto his lap facing him.

“Rachel your body is so soft…” Rick was grabbed and seated, legs spread on this man’s lap and bulging crotch. Rough hands hiked the hem of the dress up high around his waist exposing his entire bottom. Only the vibrator and thong was between Derek and his carnal treasure. The same hands then pulled down the string like straps of dress off the shoulder down to the elbows, then pulled Rick’s arms up through them. Rick, still eyes closed and barely able to control himself, realized he was nearly naked with a man he was told not to give himself to. But Derek was a professional. He forced his tongue into the boy’s mouth, roaming his hands all over the exposed flesh. He had his way groping and grabbing the boy’s breasts, his neck, his waist, and especially the smooth ass. His fingers traced along the thong and began to twist, push, and pull on the vibrator plug. He began to pull and push it more and more like a dildo, bringing Rick to moans and shrieks of pleasure. Other men walked by the curtain smiling and hollering. Derek continued to kiss, suck, fondle every bit of young smooth flesh as he nearly was pulling the vibrator out before plunging it back into Rick.

“Rachel, kiss me. Kiss me and undo my shirt. Come on, baby. Help me feel good too…” Rick in a trance felt his tongue being dominated. When he couldn’t bring himself to undress this man, bigger hands took his and guided them to the shirt buttons in front of him and slowly he did as he commanded, one by one, exposing a hairy chest and prominent belly. As the last button was released, the shirt fell open completely and he felt the near total skin contact. Derek groaned as he was getting what he wanted. He pulled away from the kiss.

“Now Rachel, my belt and pants. Time for you to meet your new toy.” Rick was alarmed. This was progressing far beyond his limits and what he promised. He knew once he opened this man’s pants, he would surely have no control. Strong hands grabbed his face and again planted a hungry kiss into his mouth. Derek was definitely a pro with his tongue. Again, strong hands grabbed his and guided his hands, this time down into a belt. He hesitated until the vibrator was popped completely out of him and then re-inserted. Rick gasped and groaned as it was pointed to massage his prostate again. He found his fingers beginning to pull the belt open. Soon the clear sound of it coming undone was heard.

“Go on… Claim it. It’s all your’s tonight. Don’t you want meet my best part?” Derek stopped manipulating the boy for the moment of truth. He wanted young men to clearly take the final step on their own when touching his manhood for the first time. The booth was silent except for their breathing. Rick noticed he wasn’t being touched but the silence drew on and somehow mounted enormous pressure on him to act. His brain was screaming because Derek wasn’t even his physical type! He wasn’t attracted to him at all. But he found his fingertips tracing along the button and zipper nonetheless. He couldn’t bring himself to just run away. But he couldn’t bring himself to take the next step. And Derek wasn’t initiating anything. He wanted to scream. Almost to just break the awkward tension raging in his mind, his fingers fumbled the pants open.

“Such a good girl, Rachel.” Derek heard his zipper lower. He kept his discipline and remained patient. Nervous, slender fingers began to feel the edge of his underwear.

“Good girl… Good girl…” Derek whispered as he knew he had him turned. Rick’s fingers gently pulled back the elastic of the boxers and at the first touch, both moaned as the electric tension broke. Rick fingers curled and gripped this man for the first time. He was hairy, much shorter and thinner than Jack, but had enormous balls. Each testicle felt like a D battery.

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