Ben Esra telefonda seni boşaltmamı ister misin?
Telefon Numaram: 00237 8000 92 32

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story.

*****

Nicholas week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn’t the case. He planted himself in front of his TV, bending his legs until his feet were on the couch before he lubed up and inserted the dildo, and turned on one of the videos his aunt had taken of him. It took him almost twenty minutes to get off, and while he could feel euphoric, it was more a lessening of pressure than true orgasm.

He had gotten used to cleaning himself up after, and was starting to pay more attention to his appearance. His clothes were well cleaned, but fairly generic, and he wondered how many people could really look at him and tell he was gay. With the triple ear piercing and the other in his lower lip, he did look a bit different, but he felt he still basically looked the same. He also got into the habit of dealing with any body hair that appeared, enjoying his time in panties and the feel of his smooth skin. His first class that day was with one of his fuck friends, and while he was able to pay attention to the class, the moment it ended he propositioned his fuck friend for a fuck in the stalls. The two went in together, and several minutes later Nicholas was left unsatisfied and with cum in his rectum. It left him disappointed, but regardless, he smiled as his partner pulled up his jeans and thanked him for using him. The guy looked down at him, nodded and opened the stall door after making sure no one was around, and walked away without a word.

Unfortunately for Nicholas, he had not nearly enough free time between his classes to get off anally, but ended up giving a blowjob at a nearby dorm when he had an hour between classes. The sexual frustration that was fueled by this new humiliation kept him constantly aroused. He was having gay sex and not even getting off, he thought how pathetic was that? He was considering posting on Craigslist for a seriously big cock to use him tonight, he really didn’t care what age they were or what they looked like, but he was saved by his aunt’s text that came late in the afternoon.

“So, I found you a man for tonight. And by tonight, I mean you’ll be spending the night with him. I showed him some of the videos we took last weekend, and he was very interested in you. He’s a little bit older than you, mid-forties, and divorced. He agreed to take you out for a date, if you’d spend the night with him. Don’t worry, I gave him your measurements, so he’ll have something for you to wear at his home. Remember, this is your first date with a man.”

Nicholas gulped, trying to calm himself so his penis wouldn’t strain against his cage, simply typing back “OK”.

Cynthia continued, “Yes, I know you’ve had tons of gay sex now, but remember, this is different. You’re going to end up having sex with him and having his love filling your orifices, and you do like men… so try and give it a shot, you may be having the first date with your future husband, have some fun! He’ll be by to pick you up at 8 on the dot, so be ready and waiting, don’t keep your man waiting.”

Nicholas almost decided to ride his dildo but held back, deciding to wait. He’d been filled at both ends, he’d humped a man’s leg, yet a date seemed significantly gayer, somehow. He knew instantly he’d be playing the role typically assigned with a girl. Date? Where would they be going? Would they know? Have fun? He couldn’t imagine trying. He knew he liked men now. He knew when they praised him, it felt good, and he knew that had opened him to appreciating them in other ways. He knew he now looked at them how he used to look at women, judging their appearance, what parts he liked, and was constantly focusing on their genitals. Which ones were cute, and which were funny, and which made him feel the most inferior. He knew most men were straight, and began to understand that most of them would never be even an option for someone like him. And he knew some of them would look at him with disgust if they knew about how gay he was.

His concerns were laid to rest when his aunt sent a picture of his date for the evening. His name was Derek. His brown hair had some moderate streaks of grey in it, and his face had clear angles. He didn’t look bad for his age thought Nicholas, who thought he looked reassuring. He never would have guessed a man like this would’ve been interested in him before. Nicholas wasn’t particularly attracted to him, but found him pleasant looking. He was only slightly taller than Nicholas, and somewhat wider. She had sent no picture of Derek’s cock, chiding him when he asked, “Does it matter? You should be thankful someone is willing to be seen with you on a date. For tonight, he’s your man, and you’re his faggot fucktoy. You better get used to it, because it’s the only way you’ll ever have a chance of finding a man to be with.” She had responded.

He aydın escort tried to dress cleanly, a plain nightshirt, combing his hair, a dark pair of slacks to cover his special panties. He found himself trying to adjust his hair for several minutes, realizing how feminine his action was, and shivered. His arousal had been stroke all day, and he was almost eager. He actually had butterflies in his stomach, and he couldn’t tell if it was because he was about to go on a date with a real man or that he was excited for it. He couldn’t wait to report to his aunt.

Derek picked him outside his apartment at 8PM sharp. He parked outside, and introduced himself, getting out to open the front door for Nicholas. His voice had been fairly even, clearly masculine but not overly so and he was dressed as a typical businessman, tie and all, looked like he had come straight after work. Nicholas smiled, and slipped into the passenger side seat and Derek closed the door behind him.

He let him know they were going to a bar as he began to drive. Derek explained his own situation, a divorce years old and deciding he was going to go ahead and fuck some faggots. To his surprise, he enjoyed more than just their bodies sometimes, and realized he was actually bisexual. He had no need to hide it, because anyone who looked at him simply assumed he was the man in any relationship, he just had that bearing about him. He joked that having a date made the night last longer, so it was worth it.

Nicholas was amazed with his candor. He also suddenly realized that this man, over twenty years older than him, was far less gay than he was. Somehow, that made him more important to please, and when the car was a red light, he reached out and grasped Derek’s dick through the man’s business slacks and gave it a squeeze, “Derek, it’d be worth it without the date. Thank you.” He thought that would make him feel good, because it was true to Nicholas.

Derek read this correctly as Nicholas willing submissiveness. The advertisement he had answered was the real deal, and he was going to insure a great night for this particular little faggot.

It turned out the bar in question was “The Sack”, and once entering, Nicholas had no doubt he was in a gay bar. It was slightly upscale, but still just a bar. Everywhere Nicholas looked, were men. The staff were men and the patrons were too. Nicholas scanned them room and noticed one of the men holding his partner by the ass, and several men were drinking at the bar alone, quite well dressed.

Derek got them a table in the back, and pulled out Nicholas chair for him, smiling. They sat, and ordered, a screwdriver for Nicholas and a light beer for Derek. Nicholas actually went through several as the night went on, while Derek refrained. Derek could tell that Nicholas was somewhat shy about his recent conversion, and was clearly a submissive, so he worked hard to lead the conversation. Derek spoke about how hard it was to find a good male partner, and Nicholas mused he was only starting to look for that, blushing. As they talked, it turned out Derek was a pretty decent guy, but occasionally Nicholas was taken back a bit by the grey in his hair, and after a particular funny experience Derek had shared, Nicholas realized that between the alcohol and his day long arousal he was sincerely showing interest in Derek, even though he was almost old enough to be his father.

Derek got up, and motioned Nicholas over to the corner, where there were a series of dart boards hung. He sunk three decently well centered as a warm up, and asked Nicholas if he’d like to throw a few first. Nicholas admitted he had never played darts before, so he joked his aim may be somewhat off. Derek nodded, and put his hands on Nicholas shoulders, pushing him into position. He stood right behind him, “Go ahead, try.”

He let Nicholas try several times, and praised him “Not bad for a first try, they all hit the board. But you’re moving just a little bit wrong.” He said, pressing into Nicholas from behind. Nicholas was tense for a moment, relaxing as Nicholas lifted his throwing arm, placing his head next to Nicholas’ ear “See, you’ve got to hold it just right.” He said, and Nicholas could feel a clothed bulge press into his ass, Derek holding his arm as if about to throw.

Nicholas couldn’t believe he was really on a date with a man. A date. Even if it was in a gay bar. His legs actually felt weak, despite being the same height, Derek was simply sturdy where Nicholas was soft and lean. Derek let go, and stood in front of him, and again, since they were the same height, he could clearly look into Tom’s eyes as he leaned in for a kiss. Nicholas was very much starting to like kissing and the two shared a short kiss, grinned and said “Well, hope you can shoot straight after that.” And Nicholas could not. He knew several people at the bar definitely noticed it, they all looked at him, at Derek, and knew what was going on.

Derek toned it back, and they did throw darts for a while, and Derek asked Nicholas about his life, actually paying attention and nazillibelediyespor.org giving his opinion, all the while casually finding a reason to touch Nicholas. He certainly wasn’t feeling love for Derek, but he could admit he would’ve considered this a good date, back when he was straight, except… well he was a sissy faggot. Nicholas asked for his fourth screwdriver in the hour since they’d been there. Derek went to pay the tab, and Nicholas stood quietly at his side, holding onto his arm. It did not come naturally to him at all, but he thought, he would’ve liked that, in the past, and once he did it, he found it not as bad as he imagined. He felt incredibly gay at that moment, whispered into Derek’s ear “I think you deserve a reward.” Derek laughed, pocketed his credit card and kissed him on the spot.

And that’s how Nicholas ended up in with Derek’s cock in his mouth for a fifteen minute drive late at night. For some reason, when the bartender had asked if it was separate bills, and Derek had said no, and paid for him, made things very real. His dating future was going to look like this. No one would likely even ask him questions like that. The man paid, and he was simply not one, not anymore. Derek held the door open for him again, and once they were inside Nicholas bent over and started undoing Derek’s pants, unbuckling and pulling his cock over his boxers, making him comfortable, before asking permission to blow him.

Derek smiled at him, saying “You just couldn’t wait for some cock, could you? Just keep me hard, I don’t live too far.” Nicholas had never tried to simply keep a man hard, but found himself aroused at the prospect. He didn’t even nod, he simply positioned himself as best he could and sucked Derek until he grew in girth and lengthy. It looked like he hadn’t trimmed down there in quite a long time, but Nicholas didn’t mind. He had cock in his mouth, and it took effort to not take him too far. He began to enjoy his cocksucking, the queasy feeling it gave him in his stomach, the pleasure from having his mouth full, the smell that reminded him of his new outlook on life.

Derek apparently had surprising stamina, though at several times he had to request Nicholas stop moving his tongue or head, occasionally holding it in place when he was at a light. “Let me tell you, Nicky, you’re a pretty great guy. You’re cute enough, and you’re definitely gay enough. Honestly, I usually like them a little less obviously gay, but I’ll make an exception. Because you were a pretty decent date, and because you’ve had your mouth on my cock for the past few minutes. Nicky couldn’t respond orally with a dick in his mouth, but he used his tongue appreciatively. The praise went straight to his head, as did the excitement at his situation. He spent his time practicing breathing through his nose, letting Derek’s penis rest at half-mast against his tongue.

He only pulled off when the car stopped and Derek patted his head. They were in a nearby suburb, and Derek owned his own house. It was two floors, though relatively small, but came with its own parking spot. They got out of the car, and Derek opened the door, flipping on the lights. It seemed like a fairly generic home, and Nicholas took off his shoes, wondered what it would be like to be here often, for this to be his home. He couldn’t believe that he was even thinking it, and it felt very wrong to him. Nicholas closed the door behind them, and Derek waited for him to turn backed and reached out to kiss him. Nicholas instantly responded by opening his lips, and soon they were French kissing, Derek using one hand to hold his head, the other groping Nicholas body. Nicholas started reaching for Derek’s cock again, and he broke the kiss, smiling at Nicholas “Honey, you’re going to have the best evening a little sissy faggot can get. C’mon, get out of that shirt and show me those nips of yours. I understand you have a tattoo too?” He grinned.

Nicholas didn’t bother to hesitate, he wanted to cum, and his penis was throbbing. He wanted Derek’s cockmeat as hard as could be so he could indulge himself with it. He pulled his shirt off as Derek went in further, turning on more lights. It was a fairly lived in place, and Derek said “Make yourself at home. It was a vodka, right?” he asked, banging around for a glass. Nicholas said “Yea” loudly enough to be heard. When Derek came back into the main room, Nicholas was on his knees on a large rug. Even though he’d had fifteen glorious minutes to savor Derek’s cock, he just wanted to please him with his mouth.

Derek patted him on the head gently, “I’ll be damned if you’re not worth that date, Nicky. You sure you want to do this? You do seem to really want it, and you have some… pretty intense tastes. I wouldn’t blame you if you wanted to leave.” He said, squatting to be eye to eye with Nicholas.

Part of Nicholas knew he could leave. He could tell Derek actually cared, and was being honest and treating him well. He thought it was almost sweet, and a sincere thing to do. It also made him want to debase himself in front of this particular man. He wondered what the chances were that he’d actually like the first man he went on a date with. Sure, his horniness and drunkenness had played a part, but he could see why someone might enjoy spending time with him. To answer, Nicholas leaned forward and craned his neck up, and held Derek’s head in his hands and kissed him. He bit Derek’s lip gently, reveling in how gay he was being.

Derek broke the kiss, and pulled Nicholas up. He handed him a glass of vodka, “Drink up, you’re going to need it.” He said, motioning for Nicholas to follow him to the bedroom. There was a table end next to one side of the bed with an alarm clock, and a well-made, large bed, a couple of chairs and a dresser with a TV on it. Derek walked over to the window, closing the blinds. “You can be as loud as you want, babe, neighbors aren’t close enough to hear a thing.”

Nicholas took a lengthy sip of vodka, his throat burning and his head in a nice warm place. Derek pulled out a box, pulling off the lid. He pulled out a long sheer dark set of stockings, “Get your stuff off, no sissy is walking around my place in those.” Handing them to Nicholas. Nicholas didn’t hesitate in removing the remainder of his clothing, and flushed when he caught Derek’s eyes focused on his chastity cage. They went up about three fourths of the way up his thighs, the silver of his cage contrasting with the dark stockings. He bent over tugging them on, making sure Derek got a good shot of his tattoo. He wasn’t sure if this was being seductive or not, he just wanted Derek to see his ass bent over. Derek stepped up to him, palming the cage in his hand. “Jeesus, I didn’t really believe it but… You’re the real deal, a fucking sissy faggot. That’s quite the statement you’ve got tattooed on you there, Nicholas. It’s pretty hot.” He said, and Nicholas flushed again. “Thank you.” He said.

Derek however, wasn’t done. He would’ve preferred a bra for Nicholas, but the nipple rings made that difficult. Instead, he tugged on them, feeling their strength, and Nicholas squirmed. He brought out a pair of three pound nipple weights, and slowly attached the weights with a short three inch leash. Nicholas was beginning to feel his arousal rage. He didn’t expect this, and it felt extremely debasing. Derek kissed each of his nipples, stepping back to take a look.

“No, still missing something.” He said, removing a small object from the box. It was a dark black choker that he allowed Derek to slip around his neck. It was made of some synthetic fabric that felt pleasant to his skin, and had a silver lock in front where Derek put it in place. “There, now you look a little bit better.” He began undressing himself as well, tossing his clothes into a pile on a chair. Nicholas could clearly smell the scent of cock and man musk. Derek was not in shape, but neither was he too out of shape, and Nicholas believed his curly chest hairs were thicker than anything he had ever grown.

Derek’s cock was semi erect, and he was surprised that he hadn’t taken advantage quicker. He sat down on the edge of the bed. Nicholas stepped closer, and Derek pulled him around, so Nicholas’s ass was facing him. “So, you were really straight just a few months ago? That’s what your ad said.” While he admired Nicky’s ass.

Nicholas’ face actually blanched. He didn’t really know what his aunt did when she found these men, he just trusted her. Somehow, it would be different if the man knew how Nicholas had swapped sexual orientations. That he enjoyed it. That every chance he had to stop, he didn’t. Nicholas was quiet, and Derek’s fingers crept towards his ass. He couldn’t share that just yet. Nicholas grunted slightly as he felt a wet finger press into his anus. “Yeah. Some stuff kind of happened, I started to like men. I think that’s why girls never really liked me that way, y’know? Now I just love sex with men.” He said, as the finger further invaded his ass.”Ugn, that feels so good.” Nicholas actually felt wetness in his eyes, “I’m sorry I’m such a fucking sissy faggot. Thank you for the date, it was my first one ever.”

Derek could tell how close Nicholas was to the edge, and teased him, withdrawing at just the right times, “its good you figured this out so young. You’re really cute, and I’m having good time tonight. Now get that cute ass of yours on my lap, faggot.” Nicholas was more than happy to comply, carefully sitting himself in between Derek’s thighs. He could feel Derek’s cock press up against his ass, a now common and reassuring feeling. Nicholas placed his hands on Derek’s thighs to keep steady, trapping the cock between his cheeks. He lifted himself slightly, massaging it. The weights attached to his nipples would give sharp, jarring tugs occasionally, and Nicholas shivered. He was experiencing quite a bit of discomfort as his own penis tried to surge and was restrained by the cage. Derek slipped his hands around Nicholas waist, into his panties. Derek’s hands were so close, and having a grown man grab for the base of his penis was equal parts horrifying and desirable. Nicholas squirmed, continuing his little lap dance. Even now, after all his experiences, he was shocked at how hard he could make dicks. Was he just a natural? Was this what he was good at it? It felt good to be so wanted, even if it was by other men.

Ben Esra telefonda seni boşaltmamı ister misin?
Telefon Numaram: 00237 8000 92 32