Remaking a Boyfriend Pt. 06: The Big Decision

Ray felt Tom's legs straddle his own, and then the gentle pushing of the head of Tom's penis against his rosebud. Tom teased him, rubbing his dick up and down his ass before centering it and pressing forward. After a few seconds, Ray felt a sharp sting as his asshole popped open and allowed Tom's cock inside. He let out an involuntary grunt of discomfort. Allison had used big dildos on him before, but Tom's cock was massive and his ass wasn't very warmed up.

Tom eased his cock in and out slowly, letting Ray get accustomed to the girth. After a few thrusts, he pushed deeper and deeper. Ray could feel his insides expanding to accommodate Tom's rigid member. Ray could barely catch his breath, his heart was pounding so hard.

Tom leaned down till his mouth was near Ray's ear. Ray could feel his hot breath. "Where's my cock, Rachel?" Tom asked quietly.

"Ohhh god, it's in my ass!" Ray squealed in response.

"Does my cock feel good in your ass, baby?" Tom thrusted in and out again slowly.

"It feels sooo good!"

Tom began to pick up the pace slightly. "Do you want me to fuck you harder?"

Ray gasped in pleasure. "Yes! Yes, fuck me harder! Fuck my ass with your huge cock."

Tom immediately begin slamming his thighs against Ray's legs, driving his cock all the way into Ray's ass. With each stroke he seemed to move faster, generating more force. His hand grabbed Ray's shoulder bracing him so that he couldn't get away from the assault. Ray's asshole throbbed; it hurt, but it also felt divine. It felt like his brain was short-circuited—every movement of every muscle was devoted to having Tom's dick as deep inside him as possible. He buried his face in the pillow in front of him and kept begging Tom to fuck him harder. Somehow, Tom managed to keep increasing the intensity of his strokes until he was fucking Ray so hard he thought he was going to explode.

Suddenly Tom stopped and pulled out. He slapped Ray's sensitive ass with his palm. "Flip over, baby, I want to see your face while I fuck you."

Ray obeyed, turning over and spreading his stockinged legs apart. As he did so, he noticed that Allison had taken off her panties and was fingering her pussy in the chair, and that she was also recording Tom and Ray with her phone. Ray was surprised, but he was too horny to care.

Tom kneeled above Ray and examined him, slowly stroking his cock. With his other hand, he lightly grabbed Ray's caged penis and testicles. Both of them together easily fit in Tom's masculine hand, accentuating the contrast between Ray's modest penis and Tom's massive one. It made Ray feel small and oddly secure to have another man touch him like this. He was aroused, but his penis wasn't straining at its cage.

"That's a cute little cocklet you have there, Rachel. I love that cage and piercing you have on," Tom said approvingly.

"Thank you, Tom. I'm glad you like it," Ray replied, blushing.

Tom leaned forward over Ray, positioning his cock at Ray's ass and his face a few inches above Ray's. He slowly slid in, his cock entering Ray's loosened asshole much more easily this time. He kissed Ray hungrily and deeply as his dick traveled inside Ray's ass. He began fucking him slowly and forcefully, each stroke perfectly moving upward to press against Ray's prostate.

Tom looked in Ray's eyes with a devious passion. "You're a slutty girl who needs to be fucked by big manly cock, aren't you Rachel?" he snarled.

"Oh god, yes," Ray moaned.

"Tell me!"

"I'm a slutty girl who needs to be fucked by big manly cock!" Ray yelled.

With each pump he could feel pressure in his prostate building, a glowing itch that spread outward from his stomach until it felt like it was radiating through his entire body. He began to feel each pulse of Tom's cock in the base of his own, a building pressure like he needed to pee.

Tom put his hand on Ray's throat, holding it just firmly enough to prevent him taking a full breath. Ray felt like a puppet, his body completely under Tom's control, each fiber and muscle at the will of this powerful man who was plowing his insides. The pressure and pulsing in his penis continued to build until he felt it overflow. He looked down and saw cum oozing out the tip of his limp penis and onto his stomach.

"Did you just cum on my cock, you little slut?" Tom asked playfully.

"Mmmhmmmm" Ray moaned.

Tom's strokes deepened and quickened. Ray's eyes rolled back as Tom fucked him. It felt like he was melting into the bed. Tom began grunting, and his thrusts became erratic. He scooped Ray's right leg under his arm, leaning over him and angling his cock deeper into Ray's ass.

"Oh fuck, Rachel, I'm coming!" Tom announced.

Ray grasped Tom's firm ass and pulled it toward him. Tom grunted loudly, and every muscle in his body tensed. Ray could see the veins and defined muscles bulging in Tom's lightly sweat-sheened body as he threw his head back.

Finally, Ray felt Tom's cock explode inside him. It was an odd sensation, but he could feel Tom's every pulse as he shot his load deep inside of him. It felt so intimate and satisfying, the hot jet of Ray's seed painting his insides. After six or so spasms, the motion ceased, and Tom stopped moving.

Ray ran his finger through Tom's hair as Tom recovered, and slowly withdrew his cock from Ray's ass. Instinctively, Ray tensed his ass to keep Tom's cum from spilling out. Ray rolled over and they both lay there, panting. Allison finally broke the silence.

"Holy shit, that was so hot! How was her ass, Tom?"

"Fucking perfect," Tom replied lazily. Allison moved over to the bed and lay down beside Ray.

"How was that, sweetie?"

"Um... amazing," Ray replied. His head was still swimming.

Allison traced her fingers down Ray's heaving chest, arriving at the small pool of cum in his bellybutton. She scooped up as much as she could, and brought the dripping creamy load to Ray's mouth. He opened automatically, feeling the still warm, salty load drip onto his tongue. He savored the taste and swallowed.

"Good girl," Allison whispered.

Tom rolled off the bed lazily. "I'm going to go clean up, you girls stay put." He strolled to the bathroom.

Allison stared at Ray intently. "How do you feel, honey? I know that was a lot to process."

"Um, I'm still a little confused," Ray said honestly, "but I know that felt fantastic. I don't know what came over me! I... I wanted it so badly."

Allison smiled. "That's what it's like as a woman to need a dick. It's such a powerful desire. And, um, one I'm feeling right now." She motioned her head back towards the bathroom where Tom had turned on the shower.

"Um, oh." Ray's head swam as he realized what Allison was saying. She wanted Tom to fuck her. A twinge of jealously hit Ray, but it was immediately followed by the thought of how she looked sucking Tom's cock. The thought Tom's enormous dick plowing her pussy sent his heart racing. Besides, it did seem that Allison should get to fuck him if Ray had. And he would be there with her. "Ok. Yeah, I mean, I get it." He smiled at her.

Allison looked delighted. "Thank you, Rachel. Today has made so many of dreams come true."

Overwhelmed with love her, Ray kissed her passionately. They began making out, and didn't even notice that Tom had exited the shower and was standing at the foot of the bed.

"Looks like you girls are having fun without me," he joked. He dropped his towel, revealing his flaccid but still enormous member.

"Not for long," Allison purred. "Rachel, it looks like he needs some help. Get him ready for me."

Ray crawled over and slowly stroked Tom's penis with his hand. Tom gently petted his hair as he worked. He placed his mouth on the head of the cock and began lightly sucking. It felt completely different working with a soft dick. He drew a few inches of it into his mouth, massaging it with his tongue. He began to feel it stir, each beat of Tom's heart bringing more blood and heat into his cock. It gradually hardened in Ray's mouth, a feeling he found delicious and intoxicating. Before long he was sucking vigorously, bobbing his head on the now hard cock.

He was lost in his task, thinking of nothing but how to please the cock in front of him. It wasn't until Allison tapped him on the shoulder that he remembered he was only the warmup. He shyly pulled away, and moved aside.

"Go sit at the foot of the bed, Rachel," Allison asked sweetly. "Tom needs some room to work."

Ray got off the bed and Tom got on. Allison scooted down so that her feet were dangling off the edge of the bed, one of them right in front of Ray's face. With a quick motion she kicked her pumps off on to the floor.

"I want you to kiss my foot while Tom fucks me, OK?"

Ray nodded. He was still buzzing with pleasure and was feeling so docile that he would have agreed to anything she asked of him.

Tom positioned himself above Allison. Ray watched with fascination as the bulging head of his cock parted Allison's glistening pussy lips. He could hear the sucking sounds of her moisture as Tom gradually worked his cock into her cunt. Allison moaned loudly as he entered her.

Ray took her foot in his hands and began kissing her soles. The anklet holding the key to his cock dangled right in front of his face as tasted the light sweat of his girlfriend's foot, all while watching her take another man's raw cock. It was an unbelievable scene, and Ray marveled at how comfortable he was feeling with it. He felt strangely happy seeing his girlfriend receive pleasure like this.

Tom began thrusting in earnest, and Allison's moans turned to screams of pleasure. Ray began sucking on her toes hungrily as she begged Tom to fuck her.

"Oh my god, fuck me with that huge cock!" she cried with wild energy. "Fuck that pussy! Make me your slut."

Ray watched Tom's muscular ass and flex harder and harder as he pounded his rod into Allison's open sex. Ray could see her creamy juices building up around the stretched lips of her pussy.

"You like watching him fuck me, Rachel? You see what a real man looks like fucking my cunt?" she said aggressively.

Ray grunted affirmatively with her toes deep in his mouth.

Tom kept fucking her deep and hard, with a metronome-like pace for what felt like ten solid minutes. Ray was impressed with how much stamina and strength it must require to keep fucking that like; it was something he had never been capable of.

Allison's moans got louder and less coherent until her back arched and she let out a cry at the top of her lungs. Ray felt her toes curl in his mouth as an orgasm wracked her body.

"Oh god, Tom!" She was shaking with pleasure, but he didn't slow down at all. As her orgasm began to subside, Tom only picked up the pace. He began grunting, and Ray could see his muscles tightening.

"Oh fuck!" Tom cried out. His balls contracted, and Ray knew that he was pumping his hot sperm deep inside Allison, just as he had done to Ray. After a few more spasms, he kissed Allison and rolled off, clearly tired from all the exertion.

Ray was still swirling his tongue around Allison's big toe as she caught her breath. He was incredibly turned on at the sight of Allison's red, swollen pussy which shined with a mixture of her juices and Tom's seed.

Allison looked down at him. "Don't just stare at it, come clean it up," she said plainly.

Ray crawled on to the bed and positioned his head between her legs. Tom fondled Allison's breasts as Ray began to lap at Allison's clit, slowly circling it with his tongue. Allison moaned and pulled him inward, indicating that she wanted him to be less delicate.

Ray opened his mouth and ran his tongue broadly over her lips. He could taste the slightly bitter musk that had been churned up by Tom's cock inside her. It was a decadent aroma, and soon Ray's entire face was buried in her folds. Allison's satisfied moans were his encouragement as he pressed his tongue deep inside her.

As he ate her, he began to taste something new, stronger and saltier. At first it was a trickle, but before long it was pouring out in globs. It was Tom's cum. This turned Ray on in a way he hadn't expected. He had already sucked another man's dick and taken his cum in his ass, but eating another man's cum out of his girlfriend's pussy was yet another illicit thrill. Ray noted that Tom's cum tasted different from his own; less sweet, and a little more sour.

"How does his cum taste, babe?" Allison asked dreamily.

"Salty. Really good," Ray replied between licks.

Tom chuckled and spanked Ray's ass playfully. "You're a perfect little slut, you know that Rachel?"

After Ray figured that all of Tom's cum had made it into his mouth, he picked up the pace on Allison's clit and put two of his fingers in Allison's pussy. Within a couple minutes, he could feel her hips bucking. He brought her to another screaming orgasm, after which she could barely keep her eyes open she was so spent.

The three of them lounged on the bed for a while after, idly feeling each other's bodies and reveling in the incredible sex they'd just had. Finally, Tom said he needed to get home to get ready for work the next day. They got dressed, and Ray and Allison saw him off. He gave Ray an extra long goodbye kiss as he left, and said he looked forward to seeing him again.

Once they were alone, Allison poured some wine and motioned for Ray to join her.

"Rachel, I just want to say that I'm completely thrilled with how today went. I was worried you would be too nervous to really enjoy yourself, and that I'd have to push you to go through with it, but you were such a natural!" She was beaming as she looked at Ray.

"I don't really know what came over me!" Ray replied truthfully. "I guess I just realized that, you were there, and you love me, and there was nothing to be embarrassed about, and so... why not try it?"

"But you liked it right?"

"Oh, it was incredible! I don't think I've ever felt that sexy in my life! And having someone else in control like that, I just felt so safe and loved. And I came so hard!" He laughed.

"Oh baby, I'm so glad. And... you didn't mind seeing me with another man?" she asked gingerly.

Ray hesitated. "I felt a little jealous a couple times, but I don't know—I liked seeing you happy, and it just kind of... made sense. I don't know how else to put it." He paused again. "Would that be, like, a regular kind of thing? If I'm Rachel, will you fuck other guys?"

Allison nodded slowly. "I won't beat around the bush. Yes. I need to have a sexual relationship with a man in my life, and even though you're so important to me and give me so much, as Rachel you can't fulfill that." She looked concerned as she waited for Ray to speak.

"It feels strange to say this," he mused, "but I think I'm ok with that. I mean, it's not like I was satisfying you when I was Ray. Plus, part of me was really turned on seeing you with Tom. And we'll still have sex right?"

"Of course, baby! I love fucking you. It's just, sometimes you need a good hard cock, you know?"

Ray chuckled. "Yeah, I guess I do know."

Allison laughed as well. "So, does that mean that Rachel is here to stay?"

Ray took a deep breath and bit his lip. "I think I'm still getting used to things, but I've felt happier this weekend than I have in a very long time. I don't think I could go back to my old life if I wanted to. I want to be Rachel."

Allison broke into a mile-wide smile and threw her arms around Ray. "You're going to be so happy, baby. We both are!"

They spent the rest of the night chatting and recounting their adventures from the weekend. It was 1am before they finally called it a night and went to bed.

**********

Despite the seismic changes of the weekend, Tuesday morning felt pretty familiar. Allison went to work, and Ray woke up a little late. He showered, using a razor to clean up the little bit of hair that was starting to regrow in a few places. After drying off, he threw on some comfortable women's athletic shorts and a tank top that they had purchased on Sunday, and tried applying a little bit of eyeliner and lipstick. The makeup wasn't perfect, but Ray thought it looked fine. He drank his smoothie, did a little yoga, and tried to work on some of his freelance projects.

Around 3pm, he got an email from Allison.

"Hey Rach! Hope your day is going well. I'll be getting home at 5—be dressed and ready to go run an errand. Wear something cute, but nothing fancy!"

Ray knew better than to ask what the errand was; if Allison had wanted him to know she would have told him. After a little bit more work, he quit for the day and started going through his new clothes to pick out an outfit. He chose a pair of short cutoff jean shorts and a casual white blouse. He put on his new necklace and chose some sandals with a two inch heel to complete the look. He noted how comfortable he was already feeling about the prospect of going out in public in girl's clothes.

He was putting the finishing touches on some more dramatic makeup as Allison got home. Ray hurried out to meet her at the car, not wanting to keep her waiting.

"I love your outfit, sweetie!" Allison said as they pulled out. "You have a natural sense of style."

"Aw, thanks!" Ray blushed.

They chatted about Allison's day at work as she drove, and before long they pulled into a parking log. Ray gulped. They were back at Human Canvas.

Before Ray could protest, Allison had dragged him out of the car into the shop. Ray's heart started to thump in his chest as Mark strode out to the front of the shop. Ray turned away and lowered his head in hopes he wouldn't be recognized.

"Allison, good to see you again, honey! And is that... is that your little guy friend? He doesn't look like much of a guy friend anymore!" Mark let out a deep rumbling laugh.

Ray's face turned completely crimson. Fortunately the shop was empty but it still felt embarrassing to be recognized, especially by a macho type like Mark.

"Hi Mark, thanks so much for squeezing us in again," Allison answered.

"Anything for a pretty face, darling, and double anything for two pretty faces! I gotta say, Allison, your friend is really wearing the hell out of those shorts!" He stared lasciviously at Ray's ass.

Allison nudged Ray. "Rachel, say thank you for the compliment."

"Um, thanks Mark," Ray said quietly.

"Rachel now, huh? I'll make a note of that. Come on back, ladies, I got everything set up for you." He was till chuckling to himself as he retreated into the shop.

Allison had to practically drag Ray to get him to move, but he finally acquiesced and slowly walked to the chair.

"So we're doing the bellybutton and both nipples, that right?" Mark asked Allison.

"Yep!" Allison replied nonchalantly.

Ray's ears rang. Three more piercings. His nipples? He opened his mouth to say something, but realized he had nothing to say.

"Can you open that blouse for me, doll?"

Ray hesitated for a second before doing as Mark asked. He fumbled with the buttons and finally opened his blouse, revealing his padded bra. Realizing what was about to happen, he removed his bra as well without being asked.

"Look at that, Rachel already has some puffy little tits!" Mark pinched one of Ray's swollen nipples with his gloved hand.

Ray merely bit his lip and looked down in response.

Mark set to work, preparing his needles and tools. He worked quickly, putting a curved barbell piercing in Ray's bellybutton and a straight barbell horizontally in each of his nipples. It hurt, but Ray was used to the pain at this point. Allison let him squeeze her hand through the whole process, and it was over before he knew it.

Mark cleaned up the piercing sites, and Ray was just about to ask about care instructions and grab his bra when Mark looked at Allison again.

"And the design you sent is going on the lower back, right?"