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Jason sat on the bed with Brianna, a lump in his throat.

"What is it," she said, "you are really freaking me out."

Jason fumbled his words, straining to maintain eye contact as he looked into her deep beautiful blue eyes. "I'm not sure how to tell you this really so I guess I will just come out and say it." The irony of his choice of words was not lost on him. Five years earlier Brianna's name was Bryan and she came out to Jason telling him her plan to transition to a woman. "I've been your best friend as long as I can remember and we've always been close but I really feel like we've gotten closer these last few months."

"What exactly are you trying to say Jason," she asked? 

"I'm trying to tell you that I want to be more than just friends," Jason said as he slid his hand up her thigh towards the cock he knew she was hiding under her skirt.

Brianna grabbed his hand and while not pushing it away didn't allow it to move further. "Are you sure this is what you really want," she asked?

Jason looked at her tan skin and ran his other hand up her slender arm resting it at the back of her neck. His hand dove into her long dark brown hair and he pulled her toward him as he opened his lips to kiss her. She did not protest at all and let out a small whimper as his tongue found its way into her mouth. He kissed her slender neck and felt goose bumps form on her leg.

Brianna pulled away for a moment of air and said, “I have wanted you for so long but I never thought you could be interested in me.”

“Let go of my hand and I will show you how interested I am.”

She loosened her grip on his hand and slid up his muscular arm as he explored under her skirt feeling the warmth as he inched closer to her cock. She let out a gasp as he finally found his target. He reached into her panties and stroked the length of it.

“I want to fuck you so bad,” Jason said as his chest heaved up and down with each breath.

Brianna pulled away and said, “not yet.” With those words she told him to lie back. She unzipped his jeans and pulled his cock out through the opening.

He admired her beauty as she sat up in front of him pulling her shirt over her head and revealing substantial breasts that appeared to be waiting for the moment to explode out of her sheer bra. She removed her bra and let them loose. They were large and perky and Jason hoped that they felt as wonderful as they looked.

She bent toward him, her breast pressing against his legs as she opened her mouth to accept his cock. She took only the head in at first, swirling her tongue around it. Her warm young mouth enveloped his cock and her tongue licked the shaft as she took him all the way into her mouth. She looked up at him with her big blue eyes as she swallowed his cock. Brianna slid his cock in and out of her mouth at a slow but rhythmic pace. As his head leaned back into the pillow Jason reached down with both hands moving her hair back so that he could see her beautiful young face. She allowed his member to emerge from her mouth and gripped at its base while licking it up and down all while staring at him with those beautiful eyes.

Jason pulled her up to him by her shoulders and kissed her. He wrapped his arms around her holding her tight as he rolled and maneuvered on top of her. He peeled his shirt off of his muscled body and stood up to remove his pants. Stepping out of his boxers as they fell to the floor, he climbed back into bed and pulled off Brianna’s skirt and panties exposing her thick hard cock. He left on her thigh high stockings because they turned him on.

His breath quickened as he pressed his body against hers. It was strange to him to feel her breasts and her cock hard against his skin. They kissed again as he ran his hand down the curves of her body, pausing for an instant at her nipple and then tracing a line down to her hips.

Jason looked at her and said, “I want to make love to you.”

She looked back up at him and said, “There will be plenty of time for that. Right now I want you to fuck me.”

Jason’s lips formed a tremulous smile. He lifted Brianna’s legs up and pushed her knees back against her chest exposing her tight little asshole. He reached for his nightstand and retrieved a small bottle of lube. He drizzled the lube onto the head of his cock. It was harder than it had ever been before as he rubbed the lube all over the head and up and down the shaft.

He slid two of his now slick fingers into Brianna’s ass and she moaned with delight. He wondered if she had been with anyone in this way since her transition but he felt as if she loved him as much as he loved her and that they had always loved each other.

Jason grabbed Brianna’s thighs as he pushed his cock against her opening and entered her. 

She bit her lip and then said, “Jason, you feel as great as I thought you would filling me up.”

Jason leaned on her using her legs on his shoulders as support and began thrusting in and out of her leaving only the tip of his cock in as he slowly withdrew before pushing deep inside of her again. With each stroke he pushed deeper inside of her and she moaned louder begging him to fill her with his hot cum.

He sat back on his ankles still thrusting inside of her but from his new position he was able to jerk her cock. He could see her balls tighten, as she got closer to her climax. After a few minutes of this he felt her tighten around him like a vice grip as white streams of liquid shot from her cock.

The feeling of her pulsating asshole as she came was too much for him and he started to shoot his load inside of her. She smiled as he filled her with his fluids.

As the throbbing in his cock subsided he slowly pulled out and positioned himself on the bed next to her. The pair stared at the ceiling with wide smiles. It seemed that their relationship was going to make a transition as well.

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EVELYN'S TV DANCE "Mr. Walters," Elaine said to me, "I want you to help me feminize my husband!" "Call me Walt." I tried not to look too surprised. It's not every day that the wife of a close business partner drops a bombshell like that on you. But then, I didn't get to the top of my profession by acting like a yokel. I went on as calmly as I could. "Just what is all this about, Elaine?" I asked. "Please don't question me about my reasons," She said. "My motives are very...

2 years ago
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Chupa Chupi Khel Ke Aunty Ko Choda

Acha to aapko bore na karte hue mai short mai apne baare mai btata hun my name is Siddharth and mai bhubaneswar odisha mai rehta hun So jo story mai share karne Wala hun vo 2011 ki hai us samay mai 12th mai tha aur Maine apna 12th apne gaon se kiya hai to story bhi mere gaon ki hi hai jaise ki aap sab jaante hain gaon mai electricity ki kami rehti hai hmare yaha 2 phase mai line kat ta tha pehle phase mai maximum ghar connected the par 2nd phase mai bahut hi kam ghar the hmare yaha 1st phase ka...

3 years ago
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She needed the money Chapter 13

All that next week Victor noticed his wife Rhonda and their house “guest” Ann were especially sexually excited. Of course he realised that it wasn’t him that was causing this. No, it was the possibility of getting a dog. Still, he wasn’t complaining as both women used him for their enjoyment. He did hope that, if they got a dog, that wouldn’t stop. After all, apart for a couple of minutes of furious humping, a dog spent the majority of time tied and not actually moving. One fact that meant...

3 years ago
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Insane Club Posse

Erica was small for her 32 years and looked more like a teenager from a distance rather than a fully grown woman, and her wicked sense of humor got us into trouble more times than you could imagine, especially when she pretended to be my daughter instead of my wife.Petite was the perfect word to describe her with slight curves in the right places, a small but firm chest and a smooth rounded ass that looked super amazing in leggings leaving next to nothing to the imagination. She left her hair...

4 years ago
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Strange Brothel

DISCLAIMER "Strange Brothel" contains graphic sexual scenes between consenting adults. It is not intended for readers under 18 or those who are easily offended by pornography. If you are under 18, or if you are offended by pornography, please do not continue to read this story. All rights reserved: Permission is hereby given to distribute this story via electronic means only, for non-profit use. This header and the rest of the story must remain intact. All rights for this...

3 years ago
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Day Dreaming

"Today we will investigate second degree polynomials in x" The teacher droned on. But I couldn't concentrate on math and my mind (and body) took me back again to HIM. AHHH, what a delicious memory. Ever since he first touched me I had been walking around with a semi and now just the thought of him had me instantly erect. Hopefully this weekend would find us together again and we could further explore each others' bodies, especially his heavy, huge and cum-filled cock. Queer, fag, fairy,...

2 years ago
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Strange Things Happenning Part 1

Hey, guys, my name is Varsha { real name }   It’s my first story nd also of my life. Hope you like my story and give me feedbacks too. So coming on topic   I’m from Jaipur city, Rajasthan and my age is 22 yrs with fair complexion body that is 5’8″ height with fat on perfect places and very sexy curves with 34d boobs and dark nipples. 4 years back I was a guy with not much muscular body but with little chubby chest and curvy ass. My friends in school used to tease me by sometimes squeezing my...

2 years ago
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Sisters Wedding Part 2

Sam woke, fully dress and did what she use to do, pulled off her bra and top turned the pillow to feel the healing powers of the cool linen, all without opening her eyes. 20 mins later she stirred again, stretch and lazily ran a hand along her thigh, slowing remembering the pleasure from last nights encounter. Running her hand up her thigh, she could feel the dry cum stuck to the skin and soft hairs. Arching her back her hand reached her groin and gently rubbed the still wet gash, probing more...

2 years ago
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A Show to Never Forget Part III

Jennifer looked at Justin, snoring loudly as he slept. "Justin wake up, time for you to get out," she yelled at him. He didn't stir at all, sound asleep. Jennifer moved next to him and shook him on the shoulder, "Justin wake up, go to your own room to sleep." Justin jumped a little and looked at her groggily, "what?" He almost yelled. "Time for you to go to your room, so I can go to bed," she said sincerely. Justin slowly rolled off of the bed and stood up, still in a daze....

2 years ago
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Craigslist Chronicles Ch 08 Job Interview

dominate masc executive looking for 'fun' interview - 38 Looking for a come hungry slut to suck me off and then take my hard cock in the office. I am conducting interviews all day Monday, Tuesday, and Wednesday for a position within my company. Looking for a break, and to live out a fantasy of mine... Come in professionally dressed with a resume in hand. The interview will be at the end of the day, so few people in the office. I have one open interview spot for Tuesday at 4 PM....

4 years ago
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Ponygirl for Hire

Part-Time Ponygirl Ponygirl for Hire?By: Long JohnsonNote: This is a work of fiction, derived entirely from my own imagination.? Any similarity between any persons living or dead is strictly coincidence, or my good luck.? I?ve never been to Arizona, I just picked it because my atlas was open to that page when I picked up. This is written in several parts (8 so far) so all of the characters listed are not in each part.? I wrote this before the Kari series.    Characters at Ponygirl...

4 years ago
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A STONED SESSION IN VICTORIA PARK

I’d been away for a few weeks, hanging out in Europe, where I’d met up with some very open-minded and horny guys – and back in the UK I felt a need to catch up with local lads for some of the kind of fun which seems so much easier to find abroad – piss fun! 

I'd been really horny all morning and on Squirt for a few hours (!) I realized I needed to have some serious piss fun and soon. So I got messaging with a piss fan in my neighbourhood, 34-year-old bear of a guy, and we decided to meet when...

3 years ago
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Sword Saint a New StartChapter 40Adventure at Miss Theresas

Chandra and I were busy for the next couple of days. The only time we were able to relax was when the tailors came to measure us for the new outfits I wanted us to have. Lady Megan had plenty, according to Chandra, so we didn't have that extra delay. I did not let our schedule interfere with her training; I made plans with the Sisters for us to work on our teamwork. We made it an afternoon at the Temple. Chandra and I needed to learn how to work together as an effective team when push came...

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