Wildwood Daisy

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A 1963 trans lady finds the guy she wants at the beach.
2.5k words
4.39
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As the engine of the 1958 Chevrolet Bel Air convertible roared, Daisy Johnson turned up the radio. It was a beautiful summer afternoon in Wildwood, New Jersey. The local radio station had the newest hit from one of her favourite artists, Bobby Rydell, running. Anytime Rydell was on the radio, Johnson had a lot of energy, no matter how bad the day had been. Pulling down the top of her Bel Air, Daisy put on her sunglasses and pulled out of her driveway.

She had sex on her mind. With all the boys in town for the summer from various parts of New Jersey, she knew she could find someone to satisfy her. Daisy had a type, and she knew she would find one near the beach. She pulled the car into a spot on East Montgomery Avenue and shut off the engine. The trip from her place to the Montgomery Avenue beach access was 5 minutes, but she didn't want to walk in her stilettos that far. Besides, she thought she'd have more appeal with the Bel Air convertible.

Climbing the embankment of sand towards the glistening Atlantic Ocean, she saw thousands of people playing in the sands. Kids building sandcastles, girls playing volleyball and tanning in the sun and boys playing football. Lots of shirtless boys. From jocks to nerds, from the extroverted to the introverted, Daisy knew who she was looking for. Pulling off her gown, it revealed a very light colour bikini that would catch anyone's attention. She placed a chair near the water and her purse on the sand next to it. At that point she decided to get a tan and people watch for a while.

----

Not far down the beach, a scrawny young man, no more than 130lb wet and 5ft 8in tall, sat in the sand under an umbrella. He liked being at the beach, though none of the girls were interested in him. They wanted the football players with the leather jackets and the varsity jackets. Those who were gonna make any girl drop dead. He, devoid of much personality and really skinny, never played sports and just tended to hide in the shadows. A reverted introvert, Jack Martinson didn't expect much at the beach that day. He just was happy to be there.

Staring around at people, Jack wondered why he could not have been on the football team or the basketball team or something to attract girls. He liked girls, or so he thought. Coming from a wealthy family in Ridgewood, New Jersey, he had all the money he could ever ask for in life. But money did not make him happy. But his parents, wealthy Catholics, would kill him if he ever admitted he liked guys in a sexual fashion. It was 1963, and the church still had a lot of power. If anyone was out, he was not aware. However, he had the ability to tell who may have been in the closet. It did not seem to apply to himself, however.

After a quick trip in the water to beat the bright Wildwood sun, Jack laid back on the towel and let the sun dry him off. As he was turning around to dry his back, he caught the glimpse of a woman in a chair about 500 feet down the beach. She looked cute in her light colour bikini, basking in the hot sunlight. Jack immediately fell into a trance. He had never seen a woman more gorgeous in his life. No matter how many pool and beach parties he had been to. No one ever had her looks. Despite his amazement, he thought there was no chance in hell this woman would have interest in his scrawny body or lack of personality.

----

Daisy came out of the water herself and sat back in her chair. Grasping a sip of water from her canteen, she looked along the beach, seeing a scrawny kid staring in her general direction. When their eyes connected, he darted a look away in nervousness. Daisy, seeing him, locked her eyes on him. "Perfect." she thought. Putting the canteen down, she grabbed a towel and waltzed down to where the boy was staring at her earlier. Coming into his personal space, she could see how nervous he was in his eyes.

"Do you like what you see?" Daisy asked in a suave feminine voice.

"ummm......ergg.....I don't know." Jack stammered, wondering how this gorgeous woman was talking to him. Him. When there were plenty of the stereotype football jocks that she could talk to and have plenty of attention. But no, she wanted him.

"I know you do, you were staring at me in my bikini. Don't feel ashamed, I'm used to being stared at." Daisy reassured him. "I don't bite. I like guys like you."

"....you do?" Jack asked in surprise, stunned that he was her preference.

"Absolutely honey. People like you are sweet and gentle. I like sweet and gentle guys. The jocks all want me to just to look good, and that's no fun." Daisy continued.

"Thanks." was all Jack could say after that.

"What brings you to Wildwood honey?" Daisy asked.

"My parents sent me here for summer vacation. Being 18 and fresh out of high school, they figured as a graduation present, I could spend the summer in a Wildwood rental home on Hildreth Avenue. I'm having a good time. I'm from Ridgewood in Bergen County." Jack responded more confidently.

"So you're here all alone? Have you met any girls here? Someone has to like you besides me." Daisy asked, more intrigued.

"Nope. Just myself. All my friends are back home in Ridgewood or at other places for vacation." Jack responded.

Daisy immediately felt herself getting warm and not just because of the Wildwood sun. She knew she had the perfect guy she had been looking for.

"My name is Daisy Johnson, I live here in Wildwood up on Susquehanna Avenue. I would like to offer to be your first friend here in Wildwood."

"You would do that?" Jack asked, even more stunned.

"Absolutely hun. I think you will make a great friend." Daisy said with the suave feminine tone she started the conversation with.

"Oh my god. I have a friend. A gorgeous friend." Jack thought to himself. Very slightly he felt a small boner begin to grow in his trunks.

Daisy spotted this and continued. "Have you ever gotten to ride in a Chevrolet Bel Air? I have one and would love to drive you around Wildwood."

"No. I'd love to though." Jack said excitedly.

Daisy motioned to Jack towards Montgomery Avenue, where she parked the Bel Air earlier that day. "Let me grab my stuff and we'll go over to the Bel Air."

"Ok!" Jack yelled. Though in his excitement cleaning his stuff up, he tripped on his towel and fell on his face in front of everyone. A laughter outbreak occurred around him.

----

Once Jack cleaned himself up and rejoined Daisy, they walked back to the Bel Air. Daisy threw her stilettos back on for driving and jumped in the convertible. Jack politely opened the door instead of just jumping in, trying to not lose his chance with the beautiful woman. Daisy re-started the Bel Air and both were soon flying down Montgomery Avenue up to Atlantic Avenue.

Driving down Atlantic Avenue, Daisy showed Jack around Wildwood for an hour from the seats of the Bel Air. The sun continued to blast down and the temperatures were still hot. After stopping at a local restaurant for a quick meal, Daisy and Jack went back in the Bel Air and drove to her place on Susquehanna Avenue. At this point, Jack's brain was racing in excitement, finding out he was going to this gorgeous woman's house! He'd never been invited to a girl's house in high school. No one ever attempted to ask him either.

Daisy opened the door to her single story house, kicked off her stilettos and put her purse down. Jack quickly followed, kicking off his sneakers behind her. Jack took a quick look around the surroundings before plopping on a chaise nearby. Daisy went to her bedroom and picked out a new outfit to wear. She pulled off the bikini, revealing her breasts, switched to a very sexy outfit in her mind. She threw an oversized t-shirt over it. Feeling happy with her look, she opened the door and walked out to the living room.

"Ever had wine, Jack?" she asked him.

"Never. My parents would never let me drink before I was 21." Jack responded shyly.

"Well, your parents are not here. I have a bottle of chardonnay in the pantry. Let's give you some." Daisy told him.

"Really? You would let me drink?" Jack stammered.

"Of course, you are an adult. I am an adult. Just do not overdo it." Daisy said reassuringly. She poured two glasses of the chardonnay in the kitchen and walked out into the living room.

After each had finished their first glass, the sun was starting to set outside. The blazing hot sun was being replaced by a beautiful starry sky with a full moon. Jack thought to himself, "this has been incredible. Wait till everyone in Ridgewood hears about this."

However, mid-thought, Daisy pulled herself away from her second cup of chardonnay and kissed Jack straight on the lips. Jack, stunned once again, quickly learned to enjoy the hard kiss from her red lips. His boner was growing and growing fast, along with the excitement in his head. "A beautiful girl is kissing me! Kissing me! Me!" his brain was screaming. Enjoying his kiss with Daisy, he let his guard down.

"Jack, have you ever kissed a girl before?" Daisy asked him, breaking the kiss. Barely able to say anything, Jack just shook his head in return. Daisy immediately kissed him again, harder. She was getting turned on and turned on fast. She had found the perfect guy. Now it was time to get him where she wanted him.

Daisy took Jack's shirt off his head, soon removing the now-dry swim trunks to reveal a 5in cock at full mast. Jack never said anything, just watched as this gorgeous woman worked on him. Daisy, unsurprised, soon put her red lips around the cock. Doing the best she could, she soon started sucking him off. Jack completely fell into a full erotic trance. She was sucking him off. He felt like a million bucks in his head as she worked her magic on his small cock. He was so excited that he could feel himself getting harder and harder internally, a brash of cum coming to the surface. However, before it was released, she pulled her mouth away. Jack was stunned.

"Why'd you stop?" he asked Daisy.

"Because, it's time to reveal who I am." Daisy said as she removed the oversized t-shirt. "I picked you for a reason, Jack." She pulled her bikini top off and slowly shimmied off the bottoms, revealing a surprise to Jack.

"You're.....a.....uhhh......guy?" Jack stammered, looking at a fully erect mast of a 10in cock fromthe pelvis of this gorgeous woman.

Daisy laughed. "Well, I was once. A long time ago. I'm not out for understandable reasons, but I still have this for my satisfaction. Jack, I came to the beach looking for a type of guy who would be able to satisfy me. The jocks do not do that. When I saw you, I thought 'boom.', he will." Daisy shook her hips, motioning Jack toward it. "Now, do you want to see what it feels like in my position?"

Jack's brain went from racing to confused. "How could such a gorgeous woman have a cock, let alone one that large? She never came off as someone other than a woman. Am I gay? If I suck it, does it make me gay?" he thought, staring at the pointy object in front of him. Eventually he decided that if he wanted to continue to be with this gorgeous woman he would do what she wants. Jack leaned over and grabbed hold of the large member.

Daisy smiled. She knew she had him. Now, she was going to take full control. Jack's pink lips were already making her feel excited. "Just suck it, Jack, it won't hurt you."

Jack complied eagerly, taking it and opening his lips. He began to suck on it. Daisy moved his head up and down to help him intake more of the member. His brain started racing again, finding out how much he liked what he was doing. His small cock was still fully erect, as the eroticness of the moment was eating at his brain. The more he did it, the more his confidence grew. Daisy just continued to smile and his head bobbed up and down. Soon, she was ready to explode in his mouth.

Jack was fully engaged as time flew under the full moon. Within another 2 minutes, he felt something creamy come out of it. He had no idea what it was, but he liked it. He wanted more. He continued to bob on Daisy's cock, feeling more and more of the creamy stuff coming out. He sooned realize he was starting to leak as well.

Daisy soon pulled his head back, fully satisfied that Jack had become her guy. Jack, a mouth full of cum, was in a euphoric mood. "Jack, honey, I would like to take your virginity now." Jack, understanding what it meant, nodded in excitement. "Is it gonna hurt?" he asked.

"Yeah, but only at first. Now get on your legs." Daisy motioned. She grabbed a bottle of lubricant and put it on herself and his tight behind. She was absolutely hot, and was ready to take this man's virginity for her own. She began to press into him. Jack clenched up at first, never having anything up his ass before. His brain was racing and screaming at this point, wondering what this was gonna be like. Soon the pain set aside as the 10in cock took over.

Daisy, now fully in him started ramming him, hard. Their excitemetns combined making one hell of a hot scene for the next 15 minutes. She came in him multiple times and at that point, Jack had experienced multiple sissygasms. Once Daisy decided she had enough, after the 5th cum session, she pulled out of him and let Jack fall on the bed, both a sweaty and leaky mess. Daisy grabbed the oversized t-shirt and her chardonnay glass and sat next to his naked sweaty body.

Jack, catching his breath, could not believe what happened. A beautiful woman had just fucked him silly. Soon he fell asleep. Daisy looked at him sleeping thinking to herself, "I got him." She put down the chardonnay and fell asleep herself.

----

When the sun woke up both of them, Daisy went downstairs and made an easy breakfast for both of them. Both scarfed it down. Then, she grabbed a fresh workout outfit and her stiletto heels. She grabbed his stuff from yesterday and gave it to him to put back on. When he did, she brought him back to the Bel Air and drove him back to his place. She gave him a kiss goodbye and jumped backed in the Bel Air, driving off. As Jack watched her drive away, the radio started playing that Bobby Rydell hit she liked.

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Femboy_AmandaFemboy_Amanda5 months agoAuthor

These are all gonna be small vignettes. I have no attention span and feel that shorter is better. Thanks though

AnonymousAnonymous5 months ago

Great story Amanda, I very much enjoyed reading it- I think it could have been a little longer story.

I would have enjoyed knowing what Jack was thinking and feeling during the lead up his many

sissygasms, how surprised was he when came hands free the first time. Also don't be shy writing the back and forth sex talk while Daisy was reaming Jack with her 10 inch girl cock. Sexy talk is good.

5 Shiny Stars for you Amanda!!

Dare

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