Two Weeks In Paradise

From the Author: This story I’m dedicating to two fantastic Authors. Their works are an inspiration to me and I’m hoping that I’ll one day be just as good as them. Thrillerauthor, your stories kept me captivated, I just couldn’t stop reading until the very end and still when the story had ended, I wanted more. Brettlynn, your series captivated my imagination and I got in serious trouble with the wife for staying up to the wee hours of the morning, reading and reading your stories. But it was worth the week in the doghouse. Brettlynn and Thrillerauthor, this story is for the two of you and I hope to do you two justice. Just to let everyone know that I alone hold the copyrights to this and every story I've written, electronic and non-electronic, and can not and will not be reproduced without my personal consent. Now lets get on with the story.

It was the summer of 1985, Dennis had just graduated from high school and he decided to take the summer off from the job he and his best friend, Brandon, had to help his father full time around the farm.

Brandon and Dennis had both been accepted to the same college on the other side of the state and had pooled their funds together so they could get an apartment together. Since they were both interested in the same things, they hung out together most of the time.

The two of them never had a girlfriend and it seemed that they only had time for each other. After Brandon had gotten his drivers license, he spent a lot of time with Dennis, helping out on the farm when they were not working that the supermarket in the neighboring town. What free time they had, was spent up in the hayloft on the farm. They put a lot of effort into making a private place for them, moving bales of hay around, creating an area where no one could see how to get into their private little area. During the summer, they used this hideaway as often as they could.

Inside of their little private area, they had placed a blanket that Dennis barrowed without his mother knowing it. During the hot summers, when they had the time, the two of them would lay on the blanket in the nude and just talk about everything.

Brandon had pretty much moved into Dennis’ home this summer, but once a week, he would go into town to visit his parents, but he would always return to the farm that evening. Dennis found that when Brandon was gone, he felt empty inside, but didn’t know what it was.

Dennis was ashamed of his body, because of his size. He was only five foot five and he was on the chunky side, but was not fat. He could keep up with Brandon when it came to farm work or at the store, but in gym class was another thing. He hated to shower after class, but Brandon would always be there to help keep his mind off of that uneasy feeling. Brandon was the only person that he could feel comfortable around with no cloths on. His belly didn’t really stick out, but his chest did and he swore they were shaped like a woman’s breast.

At the end of July, Dennis’ parents took off for their dram vacation to the Pacific Islands. Because the farm had been very successful, they were able to take two weeks off and allow Dennis and Brandon to run things. Dennis and Brandon drove them to the nearest airport and after watching them depart, they drove the two hours back to the farm.

The next day, the two of them got up early and before they knew it, the daily chores were done and it wasn’t even noon yet.

“Dennis, I’m going to town for a few hours.” Brandon said.

“Okay.” Dennis replied. “I’m going to grab a shower while you’re gone.”

Brandon went to his room to get something while Dennis, feeling quite nasty, went to the bathroom and started the water to take his shower. When Dennis was done, Brandon was gone and the house was empty. He wandered around the house in the nude, allowing the air to dry him off the rest of the way. He felt very good not having to wear any cloths and he wished that he could do it more often.

Going from room to room, he found himself in his parent’s bedroom. Going around the room, he stood in front of his mother’s dresser and found himself opening the top drawer. Inside, his mother kept her bras and panties, along with her hosiery.

Dennis picked up one of the bras and held it to himself. With his heart pounding hard in his chest, he slipped one arm through a strap and then the other. He reached behind him and fumbled with the clasps, but managed to get them fastened. He then pulled out a pair of white cotton panties and slipped them on. He went over to his mother’s full-length mirror and looked at himself in it. He laughed at his image, but he became aroused with the way the bra and panties made him feel. But something didn’t feel right.

It dawned on him.

He had hair on his body. It was not thick hair like his father’s, but it was there.

Dennis took off the bra and panties and after finding a pair of scissors, and he went into his parent’s bathroom. He sat on the side of the tub and got to work as he trimmed the hair off of his legs, pubic hair, and under his arms. The hair on is fore arms were so fine, that he left them. After he flushed the hair he trimmed off, he flushed it down the toilet. With a new razor and the shaving cream, he sat on the side of the tub and ran some water into it. When the water was only a few inches deep, he shut off the water and got to work, shaving his legs, groin, and under arms. The feel of the razor sliding against his skin felt wonderful to him and when he was done, he emptied the tub, rinsed it out and put everything back.

Dennis returned to his parents’ room and put the bra and panties back on.

As Dennis looked at himself in the mirror, he noticed that because his hair came down to his shoulders, he looked like a woman, but there was some things missing.

Dennis looked at the alarm clock on the nightstand, next to his parent’s bed and it told him that only an hour and half had gone by since Brandon had left. Mentally, he calculated that Brandon would be back in about three hours, plenty time to continue on with his dress up fun. At first, Dennis felt that shouldn’t go on, but something inside of him needed for him to go on.

Going over to the closet, Dennis looked through his mother’s outfits and came across a floral summer dress that was left behind by his mother. He took it out, and looked at the shoe rack that hung on the door. Dennis selected a pair of blue high heels and took them over to the bed along with the dress. After he placed them carefully on the bed, he sat down on the bed next to them, Dennis said to himself, “I don’t even know why I got the shoes out, and they’re not even going to fit me.”

Dennis took one of the shoes and when he slipped it on his foot, his head began to spin as he found out that it fit him perfectly. After putting the other shoe on, he realized that he and his mother had the same shoe size.

He took the shoes off, not wanting to fall flat on his face, and got up to go over to his mother’s vanity.

Dennis sat down in front of it and found that his mother left quite a bit of her makeup behind. He took some of it and began to apply some of it to his face as he seen his mother do. He started with the foundation and applied it to his face. When he noticed how it worked, he continued on and soon, most of the flaws on his face were gone. Next, he moved to his eyes and used the eyeliner then the eye shadow. He took a little while to apply eye shadow, not knowing which color to use, but then remembered what color that his mother used. Finding the color, he applied it and with he was satisfied with the results, he moved on the mascara. The blush was the hardest thing for him to apply, but when he got it on right, he finished with a light tan color lipstick.

He brushed out his long, light brown hair until it shined, then got up and slipped on the dress. Dennis managed to get the back zipped up, after finding his mother’s long handled grippers, then put on the light blue heels.

Dennis had some problems walking around in them at first, but after a few minutes of practice, he was able to imitate his mother’s walk with out falling. He swayed up to the mirror and what he saw, numbed him. Looking back at him was his mother image at his age. Everything from his head to his toes was the image of a beautiful woman.

As he turned to go back to the bed, he stopped dead in his tracks as his heart dropped to the floor.

Standing in the doorway was Brandon.

Dennis could not move as Brandon walked towards him and when he got to him, he stopped in front of Dennis.

“Hi.” Brandon said. “What’s your name?”

Dennis couldn’t say a word at first, but then managed to stutter, “Ddenise.”

Brandon placed his arms around her waist.

“You’re very beautiful, Denise.” he told her.

“Tthank you.” Denise managed to say.

Brandon leans down to her and before she could protest, he kissed her on the lips. Dennis became breathless. Never in his life had he ever kissed a girl before, much less a guy.

He soon found himself kissing Brandon back as his arms found their way around Brandon’s neck. His confined member had started to become aroused, but with the way it was positioned, the head was being pushed back towards his ass cheeks.

“Mmmm…” Brandon moaned. “Your lips taste sweet.” he said as he paused, the continued to kiss Denise.

Denise’s cock grew painfully hard and she wanted to reach down to adjust herself, but she didn’t want to ruin the mood.

Brandon sensed that Denise was felling kind of crowded, he reached down and pulled her dress up enough to expose her panties. He reached I to them and he found her hard member. Brandon pulled it forward, giving her more freedom. He continued to kiss Denise as he held on to her cock and he squeezed the thick shaft. Brandon heard her moan with pleasure and slowly, he stroked it.

Denise instinctly rotates her hips while pressing her breast into Brandon’s chest. It did not take long before she began to breath heavily and Brandon felt the head of her cock wet with her pre-cum.

“Let’s go to the barn.” Brandon whispered to Denise.

“Okay.” Denise replied as she hesitated before letting him go.

Brandon placed her cock back into her panties and let the bottom of the dress go. He took her by the hand and led her out of the bedroom and down the hallway. Just outside of the bathroom, Brandon stopped and let go of Denise’s hand, then slipped into the bathroom. Returning within a minute, she noticed that he had a jar of Vaseline. Denise knew what he had in mind and wanted for him to take her.

Holding her hand once more, Brandon lead her out of the house and moments later, he had her up in the barn’s hayloft. He let go of her hand and got the blanket they used. Brandon spread it out on the hay-covered floor and then went back over to her. He led her on in and helped her down on it, then layed next to her. Brandon began to kiss her lips passionately.

Denise moaned as his lips gently caressed her neck and moved her head so that Brandon had better access to her neck. With on hand, he squeezed her breast through the dress and bra. Denise moaned again and Brandon moved down her. He lifted her dress up and she raised her hips up as he moved the dress up. Brandon grabbed the sides of her panties, she raised her hips up again and he took them off of her.

Denise’s cock was raging hard as Brandon lowered his head and engulfed the throbbing shaft in his mouth.

“Oh god!” Denise breathed out as Brandon slid his lips along the entire length of her shaft.

She held his head with her shaky hands, while she spread her legs wider apart. Brandon’s tongue pressed against the spongy head of her cock, and then flicked the underside, sending jolts of pleasure throughout her body. Denise moaned again as she threw her head back. Her cock began to grow larger and her testicles tighten, preparing themselves to release their milky contents.

“Oh Brandon!” she managed to moan as her breathing became more labored. “I’m going to come!”

Brandon increased his efforts, his mouth and lips tried to keep up with Denise’s demands. The touch of her hands on his head encouraged him on as she lifted her hips off of the blanket.

“Oh god!” Denise screamed out loud as her sperm flooded Brandon’s mouth. He managed to swallow some of her, but the amount of it was just too much for him. Streams of cum flowed down his chin from the corners of his lips.

When Denise had calmed down from her orgasm, Brandon began to clean her up from what had leaked out from his mouth. Denise jerked and shivered every time that Brandon’s tongue touched her skin. He took his time and when he was finished, he crawled up to her and layed next to her.

She rolled on to her side and placed her head on his chest. Both of them laid there for a moment as she listened to his heartbeat. She moved her head to his shoulder and slowly unbuttoned Brandon’s shirt. Slipping her hand inside of it, she lightly caressed his nipples, sending a jolt of pleasure to Brandon’s groin. Denise moved her hand down and unbuttoned his jeans. She smiled to herself as his zipper went down and her hand found its way to his soft member. Brandon didn’t say a word as he felt her stroking his cock.

Brandon never wore any underwear and he knew that she would not have any trouble getting to his growing cock. He felt her grasp his rapidly grow cock hard and his cock jumped as she sucked on one of his nipples.

Denise stopped after a few minutes, looked up at him with a pleading look in her eyes and begged him, “Please Brandon. Please fuck me.” She moved herself so that she could look at him in the eyes. “Brandon, I need your cock in me!”

Brandon sat up and Denise helped him out of his cloths. He turned to her and slowly slipped the sundress over her head and when she tried to take off her bra, he stopped her.

“I like it.” was all that he said.

As she got on her hands and knees, he grabbed the jar of Vaseline, then moved behind her, and got on his knees. Spreading her ass cheeks apart with one hand, he smeared some of the Vaseline on her anus. Denise moaned as she felt Brandon’s index finger slowly slide into her. He continued to finger fuck her while applying more of the lubricant to her. After getting three of his fingers in her, Brandon rubbed some of the lubricant on his cock and placed the head of it against the entrance to her anus. He slowly pushed it forward as the muscles of her rectum resisted, but then gave into his persistence.

Denise felt the head of Brandon’s cock pop inside of her and she was surprised that she did not feel and pain at all, just a little discomfort. Brandon waited as she adjusted to the size of his cock, before continuing on. She wiggled her ass and he proceeded to push more of his cock in her.

When about a fourth of it was in her, Denise sighed and slammed the rest of it in her. The sudden full violation of her anus was just too much for her as she nearly passed out and her arms and legs gave out. Falling to the floor, she brought Brandon with her and his cock was shoved even deeper when he landed on top of her.

Denise comes to and Brandon’s cock was still inside of her.

“How long was I out?” She asked Brandon.

“Not long, love.” he answered her. “Are you okay?”

“I think so.” she replied. “I think that you can continue now. There’s no more pain.”

A second later, Denise felt his cock withdraw and then push back in her. He slowly pumped her as he kissed the back of her neck.

“My god, Denise!” Brandon groaned. “You are so fucking tight!”

He stopped moving to allow the excitement in his testicles subsides. When he had calmed down, Brandon started to pump her ass again. Using long steady strokes, his cock would come out just till the head was in, then he would lame it back in. Every time his whole shaft was in her, she would grunt and wanted more.

Brandon could feel the tension building up inside of his balls and he knew that his release was going to happen soon. Reaching under her, he grabbed her bra-covered breast and humped her harder. The presser in his testicles increased as the slapping noise, moans, and grunts increase with every thrust. Squeezing her breast, he cried out as the first stream of cum is deposited into her. With every inward thrust, more cum is left in her and with one final push, Brandon collapsed on top of her, out of breath.

Brandon’s cock remained inside of Denise, but as it softened, he kisses her cheek then her neck. After laying there a moment longer, Brandon rolled off of her. Both of them move to their sides, facing each other and gazed into each other’s eyes. Denise moved and kissed Brandon on the lips.

“Well, I better get back to the house and clean up.” Denise said after the kiss.

“You’re not going to get out of those cloths, are you?”

“I should.”

“Please don’t. I like you this way.”

“Which way?”

“The way you are now. You’re so beautiful.”

“I guess I could, but how long should I… you know… stay this way.”

“Until your parents get back.”

“Okay… but if I get caught…”

“You won’t.”

Denise got up and slipped back into her dress. Brandon follows suit and got back into his cloths. After they where fully dressed, the two of them walked back to the house, hand in hand.

When they arrived back at the house, Denise noticed the time and realized that it was almost suppertime.

“What would you like for dinner?” she asked Brandon.

“Why don’t you surprise me.”

“Well, why don’t you go take a shower then relax in the living room until dinner is ready.” she said.

“You know,” he said with a smile, “I think I will>“ and them Brandon Kissed her then headed to the bathroom.

Denise walked into the kitchen and began to cook their dinner. Wanting to make Brandon happy, she fried a couple of steaks and heated up a few vegetables. She set the table with a couple of candles in the middle, then after putting the food on the table, she went into the living room and found that Brandon had fallen asleep on the sofa. Waking him with a kiss on his face and lips, Brandon looked up at her with a smile and she told him that dinner was ready.

Brandon knew that Denise’s mother taught her how to cook, but he didn’t realize how good she was until he took his first bite.

“This steak is fantastic!” he exclaimed and devoured the entire contents on his plate.

Denise smiled as she worked on her plate. She was glad that she had listened to her mother when it came to cooking.

When they had finished, Brandon helped her clean up and they went into the living room. Denise curled up to him on the sofa and they watched a movie on the television. Every now and then, Denise would feel Brandon’s fingers running through her hair, which sent chills down her spine.

The next thing she realized, that the news was on and she still had her head laid on Brandon’s lap. She let out a sigh and sat up. Brandon smiled at her warmly and she leaned over to kiss him. Never in her life had she ever felt so happy with things. As they kissed, she toughed his cheek tenderly and when they stopped, she looked into his brown eyes. The look she saw was good, but she didn’t know what it meant.

“Let’s go to bed.” Brandon said to her.

They got up and headed towards Denise’s parent’s bedroom, hand in hand. When they were in front of the bathroom, Brandon told her that he needed to use the told and went in while Denise continued to the bedroom. Once in the bedroom, she went over to her mother’s dresser and found in one of the drawers, a short nightie. Quickly, she changed into it and then went over to the bed. Denise turned down the covers, got into the bed and waited for Brandon to come to bed.

A few minutes went by before Brandon walked into the bedroom. He got out of his cloths and jumped under the covers. Denise snuggled up next to him and they began to kiss each other.