Date: Mon, 13 Feb 2023 01:09:22 -0500 From: Olivia Princezza Subject: Jackie's Date Date:2/13/23 Name:Olivia Email: OliviaPrincezza8@gmail.com Story: Jackie's Date (M/CD GayTeen) Please support Nifty. All characters in this story, living or dead, are purely coincidental. This is a work of fiction. Jackie East is 17, He has long long blonde hair, green eyes, he stands at 5'4", 105lbs. He has a thin body. People say he looks very effeminate. He creates videos on the internet. And does some live streaming. Usually it's him talking about the latest video games or movies coming out, react videos that type of stuff. Things in general. Also he enjoys wearing women's clothing. One day he was talking to his audience, while wearing a cute blue skirt, and white blouse. "Hey chat, I have a fun idea." "How would one of you lucky guys or gals like to win a date with me?" "The rules are simple." Jackie took a breath. " Send me an email, my address is below, and why you want to date me." "Also you must be in the same city, state or nearby state, as me." "I'll pick the winner in a week or two." Jackie went and started his review on upcoming video games. Jackie was reading a few of his emails late at night. One email was from a guy named Jason. Dear Jackie, I would like to date you, cause you are so beautiful. You would make me happy if you went out with me. -------------------------------------------------------------------------------- ------------------------- One was from a girl name Stacy. Jackie you are so beautiful, I would love to go out with you on a date. We could even go to the malls and shop together, get our nails done and fun things like that. -------------------------------------------------------------------------------- ------------------------ All the emails were pretty much the same. People were saying how beautiful he was. And do some things like go to a movie and dinner. Do some shopping. Some offered marriage, some money. Honestly he was having a hard time. He was thinking he might lie and scrap this plan for now. Until he saw one email. It came from someone named I'm Your Big Daddy. Hey, If you are reading this. I say, you go out with a real man. I'm 6'5", 43 Y.O. 250lbs of muscle, dark hair, and a 7in cock. I like to build things, work on cars, exercise, I have my own gym in my house, I work from my house and do a little gardening... -------------------------------------------------------------------------------- ------------------------- Jackie didn't bother with the rest of the message. This was the winner. He sent everyone who entered an email and announced the winner tomorrow. Jackie went on the air and started his live stream. "People the winner for win a date with me is..." Jackie took his hands and slapped this tabletop like a drum. " I'm your big daddy." After that he thanked everyone who entered and said he may do this again in the future . After his live video was done, Jackie reread I'm Your Big Daddy's email. Then sent Big Daddy an email: Looking forward to our date. When and where shall we meet? Also what is your name? Jackie sent the message. A minute later came the reply: When: Friday Morning 9 Where: Diner on 12th I'll be wearing jeans, white tee, and brown work boots. My name is Ivan. But call me Daddy -------------------------------------------------------------------------------- . Jackie sent another message, See you Friday. Jackie kept up with the channels and talked about everything like usual. He also mentioned he would give an update on his channel about the date. He was also making jokes. People asked when and where the date would be. However he refused to say. He said he would be unfair to the winner and him. It was Friday. Jackie was up at 7. Showered then got dressed, happy knowing he never needed to shave. He threw on his pink nylons, tan skirt, white blouse. He put his red lipstick on and some other make-up. His hair in a ponytail. He then slid into his knee high pink boots, and grabbed his purse. He left a note for his family and headed out. He decided not to take his car and walked to the diner. It was a nice day for a walk and besides he seldom goes out in public dressed like this. Jackie got to the diner five minutes earlier. The place looked empty except for the wait staff and four customers. In fact he was waiting for the staff to tell him they were closing for the evening. That's how empty it was. The waitress walked over. "How many Honey?" "Two." "My date isn't here yet." The waitress walked her over to a booth with a big window where you can see the traffic and people entering and leaving the restaurant. It was here that he saw someone fitting his dates' description coming up the steps. Jackie thought he looked like someone combined The Incredible Hulk(minus the green skin) and a football player into one being. He came into the restaurant and the waitress pointed him to where Jackie was sitting. "Hello." He said. "Hi." Jackie's voice squealed a bit. "So we'll order breakfast then we can go from there." "Sounds good?" Ivan asked. Jackie nodded. He was afraid to speak for a minute thinking his voice would squeak again. "So why did you choose me?" He gulped some air. And in his normal voice spoke. "Your answer seemed to be very honest." "Also the other emails I got felt empty." "I can't describe it." "People offered me money and marriage. But I had no interest." "How long have you watched my stream/channel?" I watched it for about a month." "I forgot you might have school today." Jackie laughed. "I graduated last year." The waitress came back and both placed their orders. Ivan ordered pancakes, with scrambled eggs and fruit, and coffee. Jackie ordered eggs in a basket, (Real thing. It's an egg fried in a piece of bread) fruit and tea. Both said please and thank you. Ivan moved a bit closer to Jackie. "What would you like to do after breakfast?" Jackie didn't know what to say. He was nervous. He stuttered. "I...I...I..." "You don't have to answer me now." After a few minutes , the waitress came back with their food and drinks. "Can I ask you a personal question?" Jackie nodded. "Ever suck a man's cock?" Jackie spat out his food and began coughing. He slapped his chest, grabbed his water cup and drank it all the way down. He took a minute to regain his composure. Ivan kept eating. Afterwards they got the check and they went dutch. "Can we go to your house and talk?" Jackie asked. "Yes we can." Jackie got into his date's sports car. "I'm sorry I shouldn't have asked you that in the restaurant." "It's okay." They got to Ivan's house. It was a nice ranch house, on the outside. They walked into his house. "This was my family's house." He said. Jackie noticed it had three bedrooms and two baths, One bedroom looked like he turned it into his personal office. Beautiful paintings on the wall. "It's beautiful." "I'm going to answer your question." Jackie answered. "Yes." Jackie admitted to himself he was attracted to Ivan. Jackie didn't know why but threw his purse down, then told Ivan "I want you to fuck me." He undid his blouse. slid his dress down and pink panties. his cock at two inches he thought was sad. "I'm sorry my cock is tiny." "That doesn't matter." Ivan took his work boots off, socks, jeans, underwear, and top. He was naked. His cock sprung up like it won the lotto. It was a good 7in. And clean shaved. "Suck my monsterous cock, faggot." "I want a nice red ring." Jackie swallowed as much of the cock as he could muster. He was happy that Ivan didn't have hair around his balls. Ivan listened to him gag as he placed his hands on Jackie's head. "That's it, you fucking slut." "Swallow the whole thing." Jackie gagged, as he moved his head back and forth. "That's a good faggot." "Oh Fuck." Ivan cried as removed his cock from Jackie's mouth and shot some thick loads of cum on Jackie's chest. Jackie was going to take a hand and wipe some cum off his chest when Ivan said "Leave it." "You want your sorry boi pussy, ass fucked?" "Yes please." "Bitch you need to ask." Jackie thought for a moment. "Daddy, will please take your big magnificent and monsterous cock and fuck my sorry ass?" Ivan made Jackie get on his hands and knees. "Think you can handle this cock in your tight ass?" "Yes Daddy." Ivan slowly took the tip of his cock and teased Jackie's ass. He also took a hand and slapped Jackie's ass . "Fuck me Daddy." "Please." Ivan took the tip of his cock and slowly pushed it in. "FUUUUUUUUCCCCCCKKKKK!" Jackie screamed as the cock slowly went in. Ivan pushed more in as Jackie screamed with delight. Finally it was in. And he began to thrust back and forth. "God, Daddy." "Fuck." Ivan kept thrusting as he pulled on Jackie's ponytail. Jackie moaned. "I'm surprised my cock fits in that tight hole, you slut." "Keep fucking me daddy." Ivan kept thrusting and gaining speed. In and out faster and faster. "Daddy, I think I may cum." "You hold your cum in." "Daddy I can't." "You can cum, after I cum in your ass." After a few more thrust Ivan shot his loads into Jackie's ass. Ivan felt load after load coming out. "Okay Princess." "You may cum now." And just like that Jackie shot his load onto the floor. "Fuck, Daddy." Jackie said breathlessly. "How about a nice shower?" Ivan asked. "Ever have a golden shower?" "No daddy." Jackie paused. Then said: "I would like to try it." Ivan made Jackie take his boots off, made him kneel on the floor. "Open your fucking mouth, you whore." Just then Ivan began peeing on Jackie. Starting at his face. some of his piss went into Jackie's mouth. He kept peeing on Jackie for what seemed like forever. Slowly going down Jackie's body. "I want you to swallow my pee." Jackie complied. "I want you to lay down." "Yes daddy." Jackie laid on the wet floor. Ivan bent down. "I see you got excited. Jackie's cock sprung up a bit. Ivan went and began sucking on Jackie's cock. Jackie kept perfectly still. He moaned with pleasure as Ivan was sucking him off. "Do you need to cum?" "No daddy." "How about pee?" "No daddy." Ivan kept sucking on Jackie's little cock. "God daddy..." Jackie was fighting back the words. "I'm going to cum daddy." A second later Jackie was shooting his load in Ivan's mouth. "Good sissy." "Fuck, now I need to pee daddy." "Okay you fucking whore, pee on daddy's chest." Jackie got up and started peeing. His stream hit Ivan in the chest. "This is hot." he told Jackie. Then Jackie laid down. Ivan down on top of Jackie. Both started kissing each other. Tongues darting in and out of each other's mouths. Jackie felt himself squirting. Jackie never squirted like this before. He probably came more times today than when he masturbated in his room alone. Ivan rolled onto his back. His cock sprung up. Jackie jumped on his daddy. His nylon cover feet on top of Ivan's legs. Ivan again inserted his cock into Jackie's ass as Jackie grabbed Ivan's hips. He slowly began to go down. "Oh Daddy." "I can't believe what a slut I am, for your cock." He said this as he kept going up and down. After a few more slides, "Damn daddy, I think you came into my ass again." Ivan laughed. Both Jackie and Ivan were sweating and hot. They were fucking for hours. "Okay you fucking whore, I got a surprise." "Get on your knees." Jackie got off. "Kneel faggot." Jackie did as instructed. "Open your mouth." Jackie opened his mouth. Ivan began jerking his cock off. After a minute or two, thick loads of cum came out of his cock. Hitting Jackie in the face and mouth. Jackie swallowed the cum in his mouth. It was sweet and salty, as he swallowed the load. "Did you enjoy yourself you whore?" "Yes Daddy." "Would you like to spend the weekend with me?" "Yes daddy." Jackie was happy he was going to spend the weekend with this guy. "We should get you a shower and clean up." Jackie jumped in the shower as did Ivan. "Do you want me to drive you to your house?" Jackie said yes as he thought about what he would wear differently to make this guy happy.