Remaking a Boyfriend Pt. 06: The Big Decision

May 1, 2024 // By:analsex // No Comment

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College

The next day, Sunday, was much more relaxed. Ray again got dressed up in an outfit of Allison’s choosing, this time a pencil skirt and blouse. Allison had him do some of his own makeup as he continued to learn how to apply everything. They went to brunch, where the waiter flirted shamelessly with them and gave them a free round of drinks. Ray tried out his girl voice a couple times when he ordered, and was happy not to get any weird looks.

After that they went shopping, and for the first time in his life Ray understood why women loved it so much. There were so many choices, and styles, and stores! Everything for men was incredibly boring by comparison. He and Allison tried on mountains of clothes, and they ended up buying him a few different outfits ranging from conservative and professional to sexy and skimpy.

After that they went and saw a new romantic comedy. It was the kind of chick flick Ray would have scoffed at before. While it wasn’t his favorite, he kind of liked how silly it was, and he even found himself crying at a sad part of the movie. He wondered if the hormones Allison had him on could be making him more emotional.

They finished off the day with a nice meal at home, and Ray rubbed Allison’s feet while they caught up on some reality TV. Even though it wasn’t nearly as eventful as the day before, it was one of the best days in Ray’s memory.

He found himself thinking about what it would mean to live as Rachel. It would be a huge change, of course, but much of it seemed natural so far. The idea and the consequences still scared him a little, but it no longer seemed ridiculous.

Monday was Memorial Day, and Allison informed Ray that they’d be having a cookout. Allison picked out a sundress and wedge sandals that they had bought the day before for Ray to wear, and they went shopping for barbecue supplies. They spent the morning preparing salads and sides. Around 2pm, Allison informed Ray that they’d be having company.

“What do you mean?” Ray asked nervously.

“I invited a friend over,” Allison responded nonchalantly.

“What friend? Do I know them?”

“Jeez, what’s with the questions? Relax. His name’s Tom, you don’t know him.”

“Well, how do you know him? And besides, I can’t be Rachel around your friends! That’s crazy.” Ray was getting increasingly nervous. Being dressed up around strangers was one thing, but this was too much.

Allison was irked by his worry. “You need to chill out. I don’t know him very well, we met through a project at work. In fact that’s kind of the point, he’ll only meet Rachel. It’s important that you be comfortable meeting new people and having a social life, otherwise this won’t work. OK?”

Ray reluctantly agreed. He was still nervous about it, but tried to trust Allison’s judgment. He knew better than to ask her any more questions.

Tom arrived at 4, right as they were getting ready to light the grill on their patio. Allison greeted him warmly and accepted the six-pack of beer he had brought.

He was older, probably late 30s or early 40s, trim and about six feet tall. He was clean shaven, with short salt-and-pepper hair that made him look very distinguished. He also had striking blue eyes, and was exceedingly handsome.

“Tom, this is my girlfriend Rachel,” Allison said.

Ray nervously wiped his hands and shook Tom’s hand. Tom’s grip was firm, and his hand felt warm and calloused. Ray felt nervous using his girl voice and gave him only a soft hello.

“A pleasure to meet you, Rachel,” Tom said in a smooth baritone. Ray noticed his eyes flit down and back up, subtly checking Ray out. Ray blushed. “It looks like you girls are cooking up a storm here!”

“Oh, it’s nothing much!” Allison replied. “Now let’s get you a beer, and you can help us out with the grill. That’s a man’s job, after all!”

Allison’s remark gave Ray a pang of confusion, and reminded him what a bizarre situation he was in. Just days ago he had never even thought to question his gender, and now here he was letting his girlfriend point out that his femininity in front of another man! He looked down at the pretty yellow sundress he was wearing and his lacquered nails peeking out the toe of his sandals. He had to say, it was strange, but that didn’t mean it was bad.

They carried the food outside and started grilling. Tom seemed to be something of an expert, and took charge of the operation. They drank and talked while the food cooked. Ray learned that Allison and Tom had worked together on a big corporate merger nine months ago, which had been a big success. Ray felt shy and tried not to talk much at first, but after a couple of glasses of white wine he gradually felt more comfortable joining the conversation.

If Tom had any suspicions that Rachel was actually Ray, he didn’t let on. He asked Ray all about his work, and seemed genuinely interested in his opinions on everything from movies to celebrities to politics. After a while, Ray noticed that Tom seemed to be finding excuses to touch him, Kurtköy Sınırsız Escort putting his hand on his shoulder after a joke or touching his waist as he moved by him to go inside. As they ate the feast they prepared and continued drinking and talking, Tom became outright flirtatious with Ray, complimenting his hair and dress and repeating how lucky he felt to spend his Memorial Day with beautiful women.

Ray felt flattered by all the attention, and even did some flirting in return. He could tell that this made Allison particularly happy, as she smiled and giggled whenever Ray complimented Tom. Around 8pm they moved inside as it was a little bit chilly. Allison announced that she and Rachel were going to powder their noses and motioned to Ray to join her. Tom said that was fine and that he would do a few dishes. Ray was a little curious what Allison wanted but didn’t think much of it. She took Ray into the bedroom.

“Are you having a good time, sweetie?” she asked.

“Yeah, absolutely,” Ray replied.

“What do you think of Tom?”

“He’s great! I’m actually surprised how comfortable I am being Rachel around him.”

“Do you think he’s sexy?”

Ray’s face turned crimson. “Well, uh… yeah. I’d say he’s pretty sexy, right?”

Allison nodded. “Oh, definitely. I’m glad you agree! Now, put this on.” She opened a drawer and pulled something out. She laid it on the bed, and when Ray realized what it was his mouth fell open. It was the black lingerie that Ray had picked out months ago with Allison at the mall! He had forgotten all about it.

“Wh… what?” Ray stuttered. “I thought… that was for you to wear?”

“Oh no, silly! I never said it was for me. I just said I would save it for a special occasion! Go on, everything’s in your size.”

“Why do you want me to—I mean what’s the special occasion?”

Allison smiled at him and looked him in the eye. “You’re going to fuck Tom,” she said matter-of-factly.

Ray’s stomach jumped into his throat. “What?! You can’t be serious! Allison that’s crazy! I’m not doing that!”

Allison could tell she had freaked him out and motioned to him to take a breath. “Just listen, Rachel. I know that sounds crazy but hear me out. I want you to have the fullest possible experience as a girl this weekend so that you can make a totally informed decision. Right now, you’re a beautiful woman. You’ve had men flirt with you all weekend, and you’ve liked it. You’ve danced with one, you’ve kissed one, you admitted that you fantasized about fucking one. You love getting fucked in the ass. I think you need to try having sex with a man, because I think you’ll like it. A lot.”

Ray shook his head. “But, but, I’m not a REAL girl! Tom thinks I’m—”

Allison cut him off. “Relax, Rach. You already pass pretty well, even better than I was hoping, but Tom knows everything. We’ve chatted a little as we became friends, and he’s pretty open about having, well, let’s say non-traditional desires. He’s the perfect guy for your first time—he’s a friend, he’s sexy, and he showed me his clean STD test. And besides, you’re exactly his type. I showed him those pictures from Saturday to make sure.”

Ray was shaking with anxiety. “You did what? Oh my god, he saw those! Babe, I can’t do it! I’m just not sure about all of this. I’m too nervous.”

Allison stroked his head. “Rachel, I know you can. You’re so strong, you’ve shown me that. And if you don’t like it, you don’t have to do it again. And also… if it would make you feel more at ease, we can do it together.”

Ray looked at her quizzically. “You mean, like, both of us? At the same time?”

Allison nodded. Ray cocked his head in thought. Somehow doing this with Allison did seem like less of a big deal. It would be more like something they were trying together. And she was right—if he didn’t like it, so what? What was it such a big deal to try something new?

“Is… is that something you want? To do it with me?”

Allison nodded again. “Rachel, I think it would be so special to share your first time with you.”

Ray’s heart was still racing. He felt like he was standing on an impossibly high cliff, trying to will himself to jump off. Finally, he closed his eyes and took the plunge. “Ok, I guess… I guess I’ll try it, if you’re there with me.”

Allison clapped her hands in delight and motioned to the lingerie. Ray pulled his dress over his head and set about putting on the intricate black bra and panties. Allison had to help him with the stocking and garter belt, making sure the bows were neatly centered on his thigh and that the belt attached properly. Ray had never worn stockings, and found that they felt incredibly sexy over his smooth legs. She gave him a pair of black high heels to finish out the outfit, and then quickly stripped and changed into her own set of lacy white underwear and high heels.

They paused to look at themselves in the mirror. The sight was almost too much for Ray. The way the delicate lace clung to Kurtköy Suriyeli Escort their lean, toned figures was absolutely mesmerizing. They looked like porn stars, or Victoria’s Secret models! He couldn’t believe that how sexy he looked, much less the two of them together. Seeing how stunning they looked gave him a new sense of confidence, and with that Allison led him back out into the living room.

Tom was waiting on the couch, arms spread confidently across the back of the cushion. He was trying to play it cool, but Ray noticed that he drew his breath when he saw them.

“My, my, that was quite the nose powdering ladies,” Tom said slyly.

“You like what you see?” Allison purred.

Tom merely let out a low “mmmm” in reply.

Allison strolled confidently over to Tom and placed her hand on his chest. “I think you need to get a little more comfortable.” She slowly unfastened the top button on his shirt, and then gave Ray a look signaling him to join in.

Ray nervously scurried over and stood at Tom’s other shoulder. His hand met Allison’s on Tom’s chest, and he looked to Allison for validation. She nodded in encouragement. Together, they continued undoing the buttons on Tom’s shirt, slowly exposing his toned, tan, and lightly hairy chest. When they reached the last button, Tom eased the shirt off over his shoulders, and Allison and Ray let their hands explore Tom’s chest. Ray was surprised at how excited he was to run his fingers over another man’s skin. He felt his heart beat faster as he twirled his fingers in Ray’s slightly coarse chest hair.

Allison moved her hand to Tom’s chin and turned in towards her. Ray watched agog as she moved in and kissed him, slowly, on the lips. He could see their tongues dance lightly around each other as their lips met, again and again. He could tell from the way Allison’s eyes were fluttering that she was enjoying it, and he could from the way Tom gripped the back of her head that he was really enjoying it.

As they made out, Ray felt his hand drift downward, over Tom’s toned abs, pausing at the top of his pants. Without even thinking about it, his fingers began to grasp at the buckle of Tom’s belt. He tugged gently at the strap.

This got Tom’s attention. He pulled away from Allison and looked at Ray with a devilish smile. Ray’s eyes closed and his lips parted instinctively. A second later, Ray felt the soft warmth of Tom’s lips on his own. It was an odd, exciting sensation—the kissing was much firmer than anything he had experienced with a woman, and Tom’s stubble made him feel smooth and feminine in comparison.

His body felt like it was melting as Tom wrapped his muscular arm around Ray’s waist, drawing him into the kiss. Ray moaned softly as Tom’s tongue intruded into his mouth. His heart was doing somersaults in his chest as they kissed passionately. His entire body was throbbing with excitement. Ray opened eyes and caught a glimpse of Allison, staring eagerly at him and rubbing her breast with arousal.

Tom took Ray’s hand that was still at his belt and guided it downward, until it found the hard outline of Tom’s member, straining against the light fabric of his pants. Ray’s brain nearly short-circuited. Holy shit, he was touching another man’s cock! What was he doing? And why was he so excited? What did that mean? And also… how was Tom’s cock so big? It felt like it was twice the size of his own!

Allison stepped in and helped Tom undo his pants as he and Ray continued to kiss passionately. With a firm yank, his pants and boxers fell to the floor. Ray stepped back to get a look.

Tom’s body was not overly muscular, but it was trim and athletic. He looked great naked, especially because of what was hanging between his legs. His circumcised cock was about eight inches long, thick, and rock hard. A tiny bead of precum was already visible, glistening at the tip. Ray was hypnotized as he watched Tom’s hand grip the base of his cock and slowly stroke it.

“Come here, baby,” Allison whispered as she grabbed Ray’s hand. She tugged down gently, and in tandem they lowered themselves to their knees. Tom’s cock was at eye level now, so close that Ray could see it lightly pulsating with the beat of Tom’s heart. Ray looked to Allison apprehensively.

“Go on, Rachel. This is what you’ve been practicing for. Suck his cock, baby.”

Ray leaned forward and opened his mouth. He pressed his soft, cherry red lips against the head of Tom’s penis, and slowly let it intrude into his hungry mouth. The dick was soft and firm at the same time, with an intoxicating taste of musk and salt. He could detect the bittersweet taste of precum as well. Tom grunted in approval as Ray pressed his tongue along the underside of the head.

“That’s it, sweetie,” Allison purred. “You’re a real cocksucker now.”

The words rang in Ray’s ears, and made his skin feel like it was on fire with embarrassment and arousal at the same time. She was right. He was officially a cocksucker. How long ago Kurtköy İranlı Escort would he have found the idea impossible? Mere weeks? He was completely unrecognizable from who he used to be. And as Tom’s strong hand moved to the back of his head, he knew that he could never go back.

He began to bob his head up and down now, flicking his pierced tongue along the underside of Tom’s cock as he did. Allison’s training was kicking in.

“Oh fuck, Rachel,” Tom groaned. “You’ve got a perfect slutty little mouth. Suck that cock, baby.”

Ray started moving faster and going deeper, until he could feel Tom’s massive cock hitting the back of his throat. He gagged briefly, but quickly remembered what Allison had taught him. With one lunge forward, the head of Tom’s cock passed into his throat, and slowly worked himself down. He got about an inch of the way from the base before he had to pull off and breathe.

“Damn Allison! You really taught her how to give head!” Tom said, obviously impressed.

“I know, right?” Allison responded, giggling with pleasure.

Ray, still panting, looked at Tom with his best possible sultry eyes. “You thought that was good? Just wait,” he cooed.

He dove back on Tom’s cock, working it with his hands and tongue. After getting it soaking wet with his saliva, he pushed it into his throat again, this time pushing further and further, until his nose was resting against the bottom of Tom’s six pack. He stayed there for a few seconds, feeling proud and horny and in complete bliss. He could feel Tom’s legs quaking with pleasure as he slowly withdrew and kissed the tip of his dick.

“OK, now I’m jealous!” Allison declared. “My turn.”

Ray rested back on his heels and watched as Tom turned toward Allison. Ray gazed with a mix of jealousy and excitement as his girlfriend, clad in ultra-sexy lingerie, put her hands on another man’s testicles and took his glistening cock into her mouth. She looked exactly like a pornstar from a high-end video. Hotter, even.

She didn’t waste any time getting into a good rhythm, working her mouth along Tom’s swollen shaft and massaging his massive balls. It was an incredible sight, Allison looking gorgeous as she bobbed her head on a huge dick and Tom flexing his toned body in sync to meet her mouth. Allison turned slightly and winked at Ray, then in one motion plunged her head all the way down on Tom’s cock, effortlessly pushing her lips all the way to Tom’s pelvis. She paused there, and extended her tongue to lick Tom’s balls. Ray was amazed, he had never known Allison could suck cock like that. But then, his cock had never been big enough for her to really show her skills.

“Mmm Rachel, seems like you still have a few tricks to learn from Allison,” Tom said playfully.

Ray blushed and suddenly felt like getting involved. He stood and moved to Tom, turning his face toward him. They made out passionately as Allison continued making love to Tom’s cock with her mouth. Ray could tell that she was getting excited, as he could hear her stifled moans as she worked. Tom broke their kiss to push two of his fingers into Ray’s mouth, which he accepted eagerly. He wound his tongue around Tom’s tough fingers as they worked their way to back of Ray’s throat before withdrawing. They resumed kissing as Tom moved his hand behind Ray’s back, working his wet fingers beneath Ray’s panties and towards his ass crack.

Ray shuddered in anticipation as Tom’s slippery index finger pressed against his asshole. He sighed with pleasure and felt his body melt as his sphincter expanded, allowing Tom’s digit inside his ass. He could feel it moving and probing inside him, and a flame of desire kindled in his stomach as it passed over his prostate. Before long his second finger was pressing against Ray’s asshole, asking to be let it. Ray happily obliged, and he felt a mix of pain and relief as Tom’s second finer slid through his tight asshole.The combination of Tom’s mouth on his own and the slight ache of his asshole being stretched turned Ray’s legs into jelly. Without even thinking, a phrase escaped his lips.

“Please fuck me,” he whispered. Tom pulled back and looked at him with a grin. Allison stopped sucking Tom’s cock and looked at Ray with surprise.

“What was that Rachel?” Tom asked firmly.

Ray quivered under his intense stare. His breath was shallow and ragged, and his heart was thumping in his chest. His mouth suddenly felt dry. “P-please fuck me,” Ray repeated.

That was all Tom needed to hear. Without another word, he helped Allison to her feet. She led the two of them to the bedroom, where Tom motioned to Ray to get on the bed.

Ray did as told and got on all fours, his ass facing the foot of the bed. Allison pulled up a chair by the side of the bed and crossed her legs. Clearly she wanted a good view of the action. Tom climbed on the bed behind Ray and ran his hands over his back, tracing Ray’s spine. Ray moaned in response.

Ray felt Tom’s mouth touch gently on his sensitive back, planting kisses on his soft skin. They moved lower, and lower, until he was kissing Ray’s smooth, plump ass. As he did so, he gently pulled Ray’s panties off his waist and removed them. Ray’s caged penis sprang free and dangled between his legs. It was aching to get hard, but the cage held it firmly in place.

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