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A TRANS Formation - Chapter 6 - Date Night At The Club

"Being open to new experiences expands my opportunities"

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Jerry wakes up Saturday morning, feeling the best he has felt since moving to Des Moines. Sipping his first cup of coffee, he recalls the emotional roller coaster ride he's been through, from the depths of despair after his first sexual encounter with Roger, to the heights of ecstasy last Saturday, when he felt Roger inside of him for the first time.

Cleaning his apartment last Saturday put him in the good mood he's been in ever since. He likes the clean environment and doesn't ever want to go back to that messy lifestyle again. Reading his new cookbook has given him a new perspective on his nutrition. He has chosen some recipes he wants to try this week, and he's made a list of what he needs.

While he enjoyed cooking last week, he knows his kitchen is woefully equipped to make most of the recipes in his book. He has one frying pan, one saucepan, and not much more. He wants to go to the mall tomorrow to shop for the things he needs. He doesn't have much money, so he knows he won't be able to buy everything at once. Like everything in his life so far, he'll have to buy a few things at a time, just like when he bought his stereo, one component at a time.

He gets the urge to roll up a joint from the stash he scored last night. His better judgement takes over when he remembers what a lazy ass he is when he gets stoned. He has things to do today, and more importantly, Roger is taking him to a 'Club' meeting tonight. He's not sure what's going to happen there, but he knows he'll probably meet some new people, and he wants to be clear-headed to make a good first impression.

After taking a bath and getting dressed, he cleans his apartment like he did last Saturday. He is pleasantly surprised when it only takes him about an hour this time, compared to five hours last week when he started with a filthy kitchen and bathroom. 

He gets his grocery shopping done early, and everything is put away by noon. After eating some lunch, there is nothing much to do but wait for six o'clock, when Roger said he was going to pick him up.

Putting on some music and lying on the couch, he wonders how tonight might unfold. He doesn't know what to expect. Talking to Allen about it last night, his curiosity is aroused. He hasn't seen Roger all week and he's feeling a bit horny for him. 

He remembers how good Roger's cock felt inside of him, and his desire to feel it again is strong. After a while, he drifts off to sleep for an afternoon nap. Waking up, he looks at the clock. It is four-thirty, time to get ready for the evening.

Feeling fresh and alert after his nap, he goes into the bathroom to wash his face and get a fresh shave. He's never had a heavy beard, only needing to shave his blonde whiskers once a week or less. He hasn't shaved his upper lip for three years, and yet, from a distance, his mustache is hardly noticeable. 

He puts on his best shirt and pants and he's is ready to go. He is disappointed when he looks at the clock; it's only fifteen minutes past five. He nervously walks around the apartment looking for something to do while he waits for Roger to call. The next forty-five minutes seem like an eternity, but then his phone rings. Jerry runs to pick it up.

"Hello?"

"Hey, Jerry, it's me. Are you ready to go?"

"Yeah, I've been ready for a while."

"Great! Hey, listen, I'm outside the building, do you just want to come out to the street? I don't see any parking spaces close by."

"Sure. I'll be right out."

Jerry hurries to get his coat on; he almost runs down the hall to get outside where Roger is waiting for him. He feels a new attraction for Roger the moment he gets into his warm car. He wants to kiss him, but since they are  in public, he doesn't. Instead, as they drive to the restaurant, he puts his hand between Roger's legs, rubbing and teasing his cock with his fingers. The smile on Roger's face lets him know the advances are welcome.

Once inside the restaurant, seated at their table, Roger begins the conversation.

"I'm sorry I wasn't able to come by this week. I had a busy time of it and just couldn't get away."

"That's OK, I understand. I'm sure you have a lot of responsibilities between your business and family. It's OK if you didn't have time to see me."

"It does get hectic at times. Sometimes I don't even have time to go to the Club meetings. I'm glad I'm able to take you tonight."

"Yeah, I hope I have a good time. Allen was telling me a little about it last night, but not much, he got me curious."

"Oh, you talked to Allen last night?"

"Yeah, I met him at The Mixx last night after work. We met a guy there who sold us some weed."

"I'm glad to hear that. I was hoping you and Allen would become friends. He's a lot like you are in a lot of ways. So... what did he tell you about the Club?"

"Not much, really. He said it depends on who shows up and what they want to do. He told me to go in with an open mind, whatever that means. He got my curiosity going, but I'm a little bit nervous about what might happen."

"You shouldn't be too nervous. Everyone is pretty easygoing. Let me tell you a little about the guys. You know that thing inside I was telling you about, that we both have, about wanting to be with a man sometimes? 

Well, all these guys have the same thing. These guys are all very successful businessmen and professionals. None of us can take a chance on society finding out about what we like to do in secret, it would ruin our lives. So, many years ago, a group of guys started this Club, to give us a safe place where we can just enjoy ourselves, and not worry about getting caught."

"How many guys are in the Club?"

"It's hard to say. We have guys come here from all over the state, but some we might only see once a year, others come to almost every meeting, twice a month."

"Twice a month?"

"Yeah. This one tonight is a smaller, more relaxed get-together. At the end of the month, we have what we call 'Ladies' Night', those can get rather exciting. I just want you to know why I'm taking you tonight, to see if you like it. And remember, you don't have to do anything you're not comfortable doing."

"Where does the Club meet? Is there like a club room someplace where you meet?"

"No, there's no permanent meeting place. We usually rent a suite in a hotel for the night. We change the place every now and then so we don't attract too much attention. The hotel staff might get suspicious if they see the same bunch of guys coming in regularly. The hotel we're going to tonight has been perfect, we might stay there a while."

"I have to admit, I'm a little nervous, and curious at the same time. But I want to be open-minded about it."

"Just try to be relaxed and I think you'll have a good time."

They finish their meal and the waitress puts the check on the table. Jerry starts to pick it up, but Roger quickly slaps his hand away.

"This is my treat. You're my date tonight. Whenever we go out like this, I don't want you even thinking about paying for anything, OK?"

"OK. I got it. Thank you for dinner, Rog."

Walking out of the restaurant, Jerry feels closer to Roger. He's never thought of himself being anyone's 'date' before. He likes the way it sounds. When Roger called him his date, it made him feel special inside. It made him want to please Roger more when they are alone later tonight.

Half an hour later, Roger pulls into a very large upscale hotel complex on the outskirts of town, by the interstate highway. Going in the front door, they walk through a very busy lobby filled with lots of people. On their way to the elevators, Roger tells Jerry the guys in the Club prefer busy places like this, because they can blend in and not get noticed. 

Jerry feels a little nervous when they get on the elevator with four other people. Roger presses the button to the top floor; the other people get off on lower floors. Walking down the hallway, Jerry notices there aren't many doors on this floor, so the suites must be pretty large. They come to the last suite on the floor, and Roger knocks on the door. The door opens only as far as the security chain allows.

He hears a voice saying, "Roger! Come on in!" 

The person inside unlocks the security chain, and the door opens wide. As they walk in, they are greeted by a friendly, older-looking man, probably in his fifties. Roger walks up to him and they embrace in a hug.

"Good to see you again, Tony." Roger turns around to Jerry.

"Tony, I'd like you to meet my new friend, Jerry. Jerry is new in town. We just got to know each other over the past month or so. I think you'll like him a lot."

"I hope so," says Tony as he reaches out to shake Jerry's hand. "Welcome to our little group, Jerry. C'mon in and meet the guys. There aren't many here yet. We kind of trickle in and out all night."

"Nice to meet you, Tony. Roger told me there might not be too many here."

"Our mid-month meetings are usually small and friendly. Can I get you something to drink?"

"Sure, I'll have a beer, if you've got one."

Jerry looks around the fancy suite. It's a large room, with a kitchenette on one wall set up with a make-shift bar and snack table. A bed is on the far wall, and near the window is a good-sized table, where five guys are playing cards.

Tony brings Roger and Jerry their beer. Leading them over to the card game, Tony introduces Jerry.

"Gentlemen, we have a new young guest with us tonight. Say hello to Jerry, Roger's friend. Jerry, I know you won't remember all the names, but these guys are Bob, Dan, Kenneth, Doug, and that good-looking guy on the end is Doctor Walt."

Going around shaking everyone's hand, he notices all of them are at least as old as Roger; two of them are a lot older. Jerry is by far the youngest person in the room.

One of the guys asks, "Hey, Jerry, do you like to play poker?" 

"I'm not sure. I haven't played too much. I'm probably not too good at it."

"That's OK, we just use play money. Doug, give Jerry and Roger a hundred dollars in chips."

Roger and Jerry sit down and join the poker game. Jerry is nervous at first, but after a few hands of poker, he starts to loosen up. These guys are having a good time and Jerry forgets about how much older they are. Over the next half hour, a few more guys drift in and introduce themselves, but Jerry can't remember any names. 

Two of the guys open a door and go into an adjacent room on the right. Someone at the table comments, "It looks like Bruce and Russell are 'in the mood'."

Everyone chuckles in agreement and continues playing. After a few more hands of poker, Jerry looks down at the few chips he has left.

"It looks like I suck at poker," he says, making everyone at the table laugh. 

Someone else says, "Good thing for you, we're not playing strip poker." Everyone laughs again. 

Jerry feels two hands on his shoulders, he turns around and sees Allen standing there. He doesn't recognize him at first because he doesn't have his hair in a ponytail tonight. Allen has let his hair out and Jerry is jealous at how nice it looks.

"Hi, Allen. How are you doing? When did you get here?"

"I'm doing great. I just walked in. Good to see you here. Are you having a good time?"

"So far, yes."

"Glad to hear it. These guys are fun to be with. I'll see you in a little bit."

Allen leaves them and goes into the room on the right. Seeing where Allen is going, someone else says with a laugh, "Now we know why Bruce and Russell went into the side room."

On the next poker hand, Jerry puts all his remaining chips in the pot and loses the hand.

"Well, it looks like I'm out. I told you guys I wasn't too good at cards."

Roger looks at Jerry and says, "Don't feel bad, buddy, I'm not doing worth a shit either. You want to get up and stretch your legs?"

"Yeah, that sounds good."

Roger sees a guy over by the bar sampling the snacks. He says to Jerry, "Let's go over here, I want you to meet someone."

They walk over to the snack table, where a middle-aged-looking man is sampling the food. Roger taps him on the shoulder from behind. "What's going on, old man?"

The man turns around. "Well, I'll be damned! Roger Drennon! I haven't seen you in a hundred years!"

"I know! It's been a while. How have you been?"

"Oh, you know me. Fucking horny as hell, and too god-damned busy to do anything about it. It's a fucking rat race out there!"

"You never change. Say... I want you to meet a new friend of mine, Jerry. Jerry, say hello to Norman, an old friend of mine from way back."

Jerry shakes Norman's hand. "Nice to meet you, Norman."

"My pleasure, Jerry, and please call me Norm. All my friends call me Norm. And you look like someone I'd like to be friends with."

Roger laughs and says to Jerry, "Norm is always the horniest guy in the room."

Norm replies, "I'm not kidding, Rog. I really am horny as hell. The fucking company has me traveling all over hell and back. Next week, the cocksuckers are sending me on another trip. I haven't had time to do shit for fun."

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The three guys start laughing, then Roger tells Norm, "If you talk real nice to Jerry, he might show you something you like."

Norm's eyes light up. "Jerry, can I talk to you real nice?"

Jerry blushes, not knowing what to say. Then he remembers Allen telling him to have an open mind. He decides to play along.

"Maybe, how nice can you be?" he says with a smile.

"Oh... I can be real nice...Why don't we take a walk into the side room?"

Before Jerry realizes what's happening, Roger and Norm take him past the poker game, into the dimly lit room where he saw Allen and the two other guys go earlier. 

As soon as they walk in, Jerry sees Allen and the two guys near the bed in the large room. The guys have their pants down to their knees and Allen has his back to them. Allen has his shirt off and is on his knees, obviously sucking their cocks. 

Roger whispers to Norm, "Looks like someone is having some fun."

"No shit. If only could be that lucky. Jerry is looking very good right now."

Roger puts his arm around Jerry and says to Norm, "I think Jerry might let you play with his package."

Jerry's attention is focused on watching what Allen is doing. He hardly notices Roger's arm around him. He's getting turned on watching Allen. Norm puts his arm around Jerry's other side and asks, "Jerry, do you mind if I play your package?"

Jerry says, "No, I don't mind at all. Play with it all you want."

Norm doesn't waste any time unzipping Jerry's pants. He slips his hand inside, feeling his cock under the underwear and running his fingers up and down Jerry's hardening shaft.

Jerry is laser-focused across the room where sees Allen stand up between the two men and lets them take his pants down. As Allen's pants drop to the floor, Jerry notices Allen is wearing a pair of black, women's bikini cut panties. 

A mesmerized Jerry hardly even notices that his own pants have been unsnapped. Norm is pulling them down, exposing his bare, hard cock. Norm takes Jerry's cock in one hand and his balls in the other.

Norm whispers to Roger, "Damn, Rog... where did you find this young cock? It's fucking beautiful!"

Roger smiles, "I told you he was nice. Go ahead, help yourself to it. I don't think Jerry minds, do you, Jerry?"

Jerry just says, "No. I don't mind at all. I like it."

Jerry isn't even aware of what he's saying. He is hypnotized by what he is seeing across the room. Allen has been standing between the two men in just his black panties, while the two men rub their hands all over his body. The front of his thin panties is showing the bulge of his hard cock. The man behind Allen is definitely enjoying playing with his ass. 

Jerry lets out a soft moan when Norm gets on his knees and starts licking his hard cock. Jerry looks down with pleasure, seeing how much Norm is enjoying his cock. But then, like a magnet, his eyes re-focus across the room to what Allen is doing.

One of the men steps out of his pants and lies on the bed. Allen follows him, gets on his hands and knees between his legs, and sucks his cock. The other man gets up behind Allen, pulls his panties down, and starts licking his asshole. 

Roger puts both of his arms around Jerry from behind and kisses on his neck. Every now and then, Norm will whisper a few words like, 'Damn, this tastes good' or, 'Shit, Rog... you don't know how bad I needed this.' Jerry is taking all this in, just letting his body go, letting it feel whatever it wants to feel. Across the room, the man behind Allen is now up behind him, pushing his cock inside his ass. 

Just as Jerry gets close to blowing his load, Roger whispers in his ear, "Why don't you show Norm how much you like what he's doing, and return the favor?"

Without thinking, Jerry obediently lifts Norm's head off his cock and whispers softly, "Norm, let me make you feel as good as you made me feel."

When Norm stands up, Jerry is surprised his pants are still on. Jerry unzips Norm's pants and pulls out his cock, telling him how nice it is. Jerry gets on his knees and takes Norm's cock into his mouth. It is about the same size as Roger's except it's not quite as thick. 

Norm gives out a moan as Jerry moves his head up and down his shaft. Norm quickly unbuckles his belt and lets his pants drop to the floor, giving Jerry full access to his balls. Norm's lets out another moan when Jerry takes his sack into his mouth, rolling his tongue around each ball.

In the background, Jerry hears Allen moaning with pleasure, but he can only imagine what it looks like. Jerry sucks harder and faster; he feels turned on when he realizes he is sucking the cock of a man he'd just met ten minutes ago, and he's liking it a lot. 

Within a few minutes, Norm lets out a loud moan. Jerry can feel his cock pulsating in his mouth. He knows what's coming. He cradles Norm's balls in his hand and feels the force of cum hitting the back of his throat. Once again he tries to swallow it as fast as he can. 

When Norm's cock goes soft in his mouth, Jerry stands up and says to Norm, "Thank you."

Norm replies to Jerry, "Oh shit, man, I'm the one who should be thanking you. You don't know how I needed that."

Jerry just replies, "I'm glad I could make you feel good." 

Norm pulls his pants back up and excuses himself to use the bathroom. Jerry looks back across the room to see the two men now have Allen on his back. One has his cock in his mouth while the other one is holding his legs in the air, fucking his ass.

Jerry stares at them until Roger comes up behind him and whispers in his ear, "It's starting to get late. Why don't we get your pants back on so we can go to your apartment and do some of that ourselves?" 

Jerry whispers back, "Oh yeah, let's go. I want you to fuck me again. I've been thinking about it all week."

Jerry gets his pants back on and takes one last look at the heavy fucking still going on the bed. As they walk into the other room, it takes a while for their eyes to adjust to the brighter lights. Most of the guys have left. As they pass the empty poker table, Norm catches up with them.

"I just wanted to thank you guys again for making my night." He puts his arms around Jerry from behind. "I'm sure glad I met you, Jerry, I hope we get to meet again soon."

Jerry feels Norm's hand going deep inside his front pants pocket as he speaks. Norm hugs him tighter, pushing his cock up against Jerry's ass. "Sometime I'd like to see what you feel like back here," he says. 

Jerry knows what he means. He just says, "You never know what might happen."

Norm thanks Roger for sharing his date, then Roger and Jerry leave the party. 

As they drive to Jerry's apartment, Roger tells him, "That was really nice what you did for Norm tonight. I was very pleased watching you pleasuring him like you did. You've really come a long way in just a few weeks, and I'm very proud of how you're learning to let go."

Roger parks the car in front of the apartment and checks to make sure no one is around. He pulls Jerry to him and kisses him deep. He says, "Let's go in and finish this night off."

Jerry replies, "Yes, I can't wait for you to fuck me again."

When Jerry closes the door inside his apartment, he wraps his arms around Roger and kisses him. 

"Thank you for taking me tonight. I loved being your date. Shall we unfold the bed?"

"Why don't we just rest a little first, and get relaxed. Did you say you got some pot with Allen last night?"

"Yeah, why?"

"Because, I want you to smoke some before we start. I want you to get really high, it'll relax you so it won't hurt so much when I fuck you."

Jerry smiles in agreement. He has a joint already rolled up. Before he lights it, he gets naked so he can be ready whenever Roger wants him. Sitting naked in his chair, he smokes the joint while watching Roger slowly undress in front of him. His cock gets hard as he thinks about what's in store for him.

When Roger is naked, he comes over and stands in front of the chair. Jerry puts the joint down and leans forward, pulling Roger close so he can suck his cock. Jerry's head is spinning from the marijuana. He puts his lips on the hard cock head, lowering his mouth over it until he feels Roger's pubic hairs on the tip of his nose. Roger lets him suck for a few minutes, then takes him by his arms, and leads him to the bed.  

He lays Jerry on his back, raising his legs up so his ass sticks up in the air. Roger then lowers his head and puts his tongue in his ass. Jerry feels like he's in heaven. Roger works his tongue inside and out, letting Jerry know how sensitive and sensuous his asshole can be. Jerry can't hold his body still as Roger skillfully exploits  his anxiety.

Still holding Jerry's legs up, Roger reaches over and gets a bottle of lube he brought with him. He squirts some on Jerry's asshole and works it in with his finger, then he strokes it onto the shaft of his cock.

"Are you ready to get fucked?"

"Oh my God! I've been ready to get fucked since the moment we walked in here."

"I want you to grab your legs and hold your ass up in the air for me. Show me you want to be fucked."

Jerry instantly obeys Roger's words, grabbing his legs, pulling them back as far as he can, offering Roger his hole to use as he pleases. Roger rubs his slippery cock up and down Jerry's crack, pressing his cock against his opening, teasing him, making him want it more. Roger puts the head of his cock against Jerry's tight hole. Suddenly, without warning, Roger thrusts two inches of his cock into him, piercing him like the tip of a sharp sword.

Jerry lets out a scream. His stretched asshole feels like it's on fire, like it's been cut with a knife. Roger holds his cock there long enough for Jerry to feel his pain before he sinks the rest of his length into Jerry as far as it will go. Jerry feels the pleasure of being filled up and the pain of being split open at the same time. 

Roger works his hole with long, slow strokes, until he feels Jerry relaxing around his shaft. As his strokes become more steady, Jerry wraps his arms and legs around him, moving his ass in harmony with Roger's moves. The pain has completely gone away now; he only feels the pleasure of being totally submissive to the alpha male on top of him.

With the marijuana's full effect, Jerry loses touch with reality, and he enters a different realm. In this moment, he forgets that he is a man. From deep inside him a female personality emerges, taking control of his body. Through Jerry's eyes, she looks at Roger, surrendering to his masculinity. She feels his cock deep inside her pussy. She contracts and squeezes her tight pussy around his cock, coaxing it to deposit the cum she craves. 

Her desire is fulfilled when she feels the warmth of cum filling her up. Roger collapses on top of her as she tightens her grip on his body. With Roger's cock shrinking inside, her arms and legs loosen their grip. She slowly recedes back into Jerry's subconscious, allowing Jerry to regain control of his faculties.

Roger looks down at him. "That was wonderful, Jerry."

Jerry can't speak. He can only smile as Roger gets up and heads into the bathroom to clean up. Returning from the bathroom, he gives Jerry a kiss and tells him, "You've come a long way tonight. I haven't made you cum yet and there is a reason I haven't made you cum yet. I'm not going to make you cum."

Roger puts his thumb on Jerry's hard cock, just below the head, moving it up and down with slow, short, one-inch strokes. He takes Jerry's thumb and puts a drop of lube on it.

He continues talking, "When I leave here in a few minutes, I want you to stroke your cock just like this. You're not allowed to take it in your hand. You can only touch it with your thumb like I'm doing right now. I want you to think about everything you did tonight, every detail. Keep thinking about it until you give yourself the orgasm you deserve. When you reach your orgasm, you'll understand why I want you to do this... you were magnificent tonight."

Roger kisses him on the forehead, gets dressed, and leaves. Jerry does what he was told, stroking his cock with his thumb. 

He thinks of how he gave his cock to Norm at the Club meeting. He remembers how hot Allen looked in his bikini panties, getting fucked by those two guys. He almost feels Norm's cock shooting its cum in his mouth again. His cock throbs as his mind replays the fucking Roger has just given him. 

In the dark void behind his closed eyes, he sees an image of a girl starting to form. As the image gets clearer, she comes closer and smiles at him. She is beautiful. She whispers in his ear, "Can we get to know each other?"

As the words come out of her mouth, cum shoots out of Jerry's cock. He has given himself a glorious orgasm. He cannot move a muscle as he watches the girl's image fade back into the void from whence she came. As the last drops of cum ooze from his pee hole, Jerry drifts into unconsciousness, entering the dream world of deep sleep.


 

 

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Written by Jilluvscox
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