Remaking a Boyfriend Pt. 05: Day One

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Steven returned with four shots of tequila and pushed one in front of Ray, smiling at her and winking. Ray looked at him. He was tall, probably 6'2". His wide-set jaw was covered with an even, dark stubble that contrasted with his light blue eyes. His rolled up sleeves revealed thick forearms, with visible dark hair (not too much) and well-defined veins. He was the kind of handsome, confident-looking guy that Ray had always felt threatened by, and here he was flirting with Ray as a girl! He was flirting, right?

Allison and the guys yelled "happy birthday" as they all took the shots. Ray immediately felt a little woozy—he wasn't used to drinking like this. He was a little scared, but also increasingly euphoric about the whole experience. Feeling suddenly emboldened, he turned to Steven, smiled, and said thanks in his best attempt at girly voice. Allison grinned at him, clearly impressed.

It wasn't long before the guys asked Allison and Ray to dance, and Ray was surprised to find himself eagerly accepting. It was clear that no one could tell that he was actually a man, and it felt exhilarating to receive all this attention.

Allison paired off with Kyle and Steven led Ray out on to the dance floor. They started about a foot apart, with Steven's hand on Ray's hip. Ray did his best to mimic the kinds of moves he saw girls doing, wiggling his hips and touching his hair. He found it hard to move much in the heels, but it didn't seem like Steven minded.

When the song changed to an uptempo rap song, Ray saw Allison move closer to Kyle, circling her arms around the back of his neck. Ray did the same with Steven. He noticed how hard Steven's muscles felt underneath his shirt. His grip on Ray's waist made Ray feel small, like Steven was in control of him.

By the time the song had changed again, Allison was grinding on Kyle, rubbing her ass into his crotch and holding his head behind her. His hands were roaming all the over the front of her body, up her legs and stomach and even brushing her breasts. Allison didn't seem to mind at all, only writhing more enthusiastically with the music.

Seeing this elicited a complicated combination of feelings in Ray. He was jealous, obviously, seeing another man touch his girlfriend. But he also understood that while he was Rachel, she didn't exactly have a boyfriend. And it excited him, seeing Allison be so sexy in the presence of a handsome man like Kyle. He was surprised to realize that there was something else there, too. He felt competitive. He wanted to be as good a dance partner for Steven as Allison was for Kyle.

Ray spun around and pressed his ass against Steven, wiggling it with the beat. Steven placed both his hands firmly on Ray's waist, driving his body against Ray's. Ray gasped when he felt something moving in Steven's crotch, and realized that Steven was getting an erection. He turned and look back at Steven, and was met with a look of pure desire. Butterflies filled Ray's stomach, and he suddenly became nervous about where Steven might expect the night to lead. At the same time, wielding the power of attraction felt fantastic, and he was proud of how he had claimed the hottest man in the club. Steven's hands started to roam as well, moving along Ray's sides and over his smooth shaved legs. Ray didn't make an attempt to stop Steven; he realized that he, too, was turned on by the image of himself as a seductive beauty in the arms of this man. He couldn't quite explain exactly why, he just knew the idea aroused him.

They danced for a few more songs before Ray Steven's hands started to get more aggressive, moving upwards towards Ray's chest. Ray stopped him, and got Allison's attention to indicate that he wasn't sure what to do. Allison got the message, and reluctantly broke away from her dirty dancing with Kyle. Ray did the same with Steven.

"Thanks boys! It's been fun, but I have to get the birthday girl home," Allison explained.

"Aw, you sure?" Kyle asked.

"Afraid so. But thanks for a lovely night!"

With that, Allison grabbed Kyle and planted a big kiss on his cheek. The parting favor clearly alleviated some of his disappointment.

Ray assumed he should give Steven one to match, but as he leaned in, Steven grabbed his ass and pulled him close. He leaned into Ray's ear and whispered.

"I love that tongue piercing. I bet you're such a freak in bed." He pulled his head back and spoke so the others could hear. "Happy birthday, Rachel!" Before Ray could do anything, he went in and kissed Ray directly on the lips.

Ray felt so surprised that he didn't move, or back away. Before he knew it the kiss was over, and he was still sorting out whether it had been an unpleasant surprise as Allison pulled him away. Ray's brain churned and images of him kissing Steven ran through his mind. A vision of the two of them in bed flashed in his vision, which he immediately pushed away.

Allison was manic as they exited onto the street and called a car. "Oh my GOD! Rachel that was amazing! He was so in to you, and you were amazing! I can't believe you kissed him."

"Well, more like he kissed me," Ray replied.

"WhatEVER, you totally wanted it! You were grinding all over him."

"I was just trying to keep up with you!"

"What did he say to you at the end?"

Ray told her, and they both laughed in response. The car arrived and as they rode back home, they unpacked the night. Once back at the house Allison poured them one last glass of wine. As the high of the nightclub atmosphere wore off, Ray brought up something that was bugging him.

"So that guy, Kyle, did you... like him?"

Allison studied his face before responding. "You mean did I think he was handsome and fun to dance with? Yes, of course. Did I want him in a way that would threaten us? No, sweetie, of course not."

"Yeah, but... I mean, if I were Rachel... would you miss being with a man?"

Allison sighed. "Yes, I would. I love men. But I love you most, and I love you as Rachel."

This response relieved Ray, even if it didn't answer all his questions.

"But now," Allison continued, "let me ask you a question. Be honest: did it turn you on to see me dance with Kyle?"

"It made me jealous, but, um, yeah. It also turned me on. Just, seeing you be so seductive like that."

That familiar devilish smile crept across Allison's face. "I think we should take this to the bedroom," she said.

They made out as they made their way to the bedroom, and as they flopped on the bed, Ray saw their reflection in the mirror and realized that they looked like every guy's lesbian fantasy right now. He felt his cock twitch between his legs.

Allison grabbed his head and pulled him in for a kiss. Ray had kissed Allison thousands of times before, but this one felt different. It was passionate, but there was something softer and gentler about the way her mouth moved on his now. They took their time, their tongues slowly engaging and intertwining, as their hands moved over each others bodies. Allison trailed her kisses down to his neck, and Ray moaned at soft warmth of her mouth. His body felt like it was on fire; he was turned on in a way that he had never felt before. He wanted to be enveloped by Allison, to be taken by her.

She moved her hand underneath his dress and gently pulled his nipple. Ray's brain went into overdrive.

"Fuck me!" he blurted out.

Allison smiled. "What was that sweetie?"

"Please fuck me!" Ray repeated, this time louder and more insistently.

"You want me to fuck that tight little ass of yours?" Allison whispered into his ear, finishing the question off with a lick of his earlobe.

Ray was so turned on that his response felt involuntary. "Mmmmhmmm" he moaned. He felt a burning hunger deep in his stomach.

Allison stood up and in what felt like seconds they were both naked and Allison was stepping into her strap-on harness. Ray's new cage resisted the throbbing attempts of his cock to get hard as he watched Allison smear lube over the glistening head of the dildo.

Ray spread his legs. Allison slid between them, her long hair hanging down on Ray's chest as she held herself over him. With her left hand, she positioned the tip of the dildo against Ray's rosebud. With a gentle thrust of hips, it slid easily in.

She took her time entering him. They kissed slowly but forcefully as Allison gradually pushed the cock deeper. When it was finally all the way in, she began grinding her hips, not pulling the cock out but still moving it.

Ray gasped with pleasure. He felt filled to the brim, and each tiny movement was a cascade of sensation inside him. It was like Allison was inside his soul, controlling his every move and sensation.

Allison began to pick up the pace. "Your ass feels so fucking good Rachel. You love having this huge cock in you, don't you?"

Ray practically squealed in response. "Oh my god, yes!"

Allison's eyes were ablaze with desire. "Mmm, right. It made me so turned on seeing you dance with that guy tonight." She started drawing the cock out and in, really fucking Ray now. "Did you like grinding on that guy like a slut?"

Ray felt a bomb of tension building in his groin as the dildo pounded his prostate in rhythm. "Mmmm yes! I liked turning him on!" he panted.

Allison slowed down and pulled the dildo nearly all the way out. She lowered her voice and looked Ray directly in the eye. "Did you want him to fuck you? Did you want his big cock in your ass?"

Ray panicked. He could barely think straight, all he wanted was for Allison to fill his ass again. He wanted to say no, but he felt confused. "Um, I don't..."

"Tell the truth! If he were here right now would you suck his cock? Would let him ram your ass and pull your hair?"

The image flashed into Ray's mind and he knew the answer. He gulped. "Yes," he said meekly.

Allison smiled ear to ear. "Yes what?"

Ray paused. "Yes, I'd want him to fuck me."

At that response Allison slammed the dildo back into Ray, and he convulsed with pleasure. She fucked him harder than she ever hand before, and pressed her mouth to his hungrily. He felt the fuse on the bomb inside him shortening. His breath quickened and his eyes rolled back, which made Allison go even faster.

The bomb went off. Every muscle in Ray's body seized as he cried out. He could feel his heartbeat in every cell of his body as a tsunami of pleasure swept over him. Cum oozed from his caged dick and pooled in his belly.

Allison gingerly pulled out. She moved her mouth down to his stomach, and sucked some globs of semen off his stomach. She kissed Ray's lips and pushed the salty juices into his mouth, which he swallowed easily. Ray's mind was swimming as she lay beside him.

"Holy fuck that was hot," he said, chest still heaving. "I don't what I... I mean, I'm not gay, you know?" He looked at Allison, who gave him an easy grin.

"Girls wanting to have sex with men isn't gay, dummy. And don't worry about stuff like that. I'm proud of you for being so open to exploring this."

This eased Ray's mind. They kissed more, and before long Ray's mouth was between Allison's legs. She was sopping wet already, and it didn't take long for breathing to grow erratic. Ray teased her, kissing around her folds and lightly tonguing her clit.

"Oh fuck, Rachel, yes, eat my pussy," Allison moaned.

Ray pressed the metal ball of his tongue piercing against her clit, which started her orgasm almost immediately. Her legs tightened around his head, and she grabbed the back of his head and pressed him into her sex.

Ray continued eating her, and brought her to two more orgasms before his jaw got too tired to continue.

Both lay speechless as their breathing gradually returned to normal. They fell asleep exhausted and sweaty, holding each other tightly.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
TrstxxxTrstxxxabout 2 years ago

Rachel’s first real cock will be amazing..great story

RegretsRegretsover 3 years ago
A little more help with the personal grooming

Although Ray was required to shave his legs there was no help or mention of shaving his bum, and keeping it shaved at regular checks. Without this addition and even with perfectly shaved legs Ray would still feel as hairy as a goblin knowing that his bum was hairy. I know it is not all that long ago, in another segment Alison did shave his bum, but a girly man notices these things. He can’t be expected to reach down there by himself. Really, it could be made one more sign of his subjugation that there are regular times when Ray has to drop everything for a sudden bum shaving appointment.

Any man who has ever shaved under his arms, to try, as a youth, knows what a huge mistake it is if one is doing physical work. Of course, it is a sign of a deep reaching femininity when women do subject themselves to this regime.

Another matter is Ray’s weight. He is now a very toned 155lbs, down from 175, but I think that a further reduction to bring him nearer to 140 lbs is desirable. 155 is just a bit too heavy for a hot woman to be. Even another 7/8lbs reduced to just under 150lbs and maintained there, or else, would show that Alison is a true master of her craft and Ray would have become a shop window to shout out her skills to those of us who can pick up on the signs of man who is truly in the control of his mistress.

A large dog, for instance at a dog show in peak condition as far as the public are concerned would very much like to get hold of a large steak and put on some weight and be as its fellows on the street, but if Mistress will not allow it the dog must just put up with life as it is, it’s love and affection for Mistress, even so, are a turn on for some who know the facts about its day to day life.

AnonymousAnonymousover 4 years ago
Love it

I love this story, from start to here now. Wish It could happen to me this way.

AnonymousAnonymousover 4 years ago
This cant be the end?

This series needs to continue! Or atleast start a new series based off of this.

AnonymousAnonymousover 4 years ago
Love it

Great story. The theme is nothing new but I love the way you have unfolded the story. The pacing is perfect. Some stories with a similar theme go forward too quickly. The pace of your story provides satisfaction with each chapter but with just enough anticipation for the next. I found myself drawn in as I read dreaming I was Rachel. Thank you so much for such a wonderful story!

Show More
Share this Story

Similar Stories

A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Making The Perfect Husband Before his wedding, submissive desires overcome Mark.in Mind Control
Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
More Stories