Companion: The Uber for Sex Ch. 02

Rachel noticed what he was doing, and looked terribly embarrassed, but wordlessly complied, turning around and giving him a close-up view of her naked ass. To my surprise, he reached out with one hand and started cupping it -- squeezing and caressing it -- which prompted Rachel to wince in surprise, but not to pull away. Matthew continued fondling himself with his other hand, now masturbating more vigourously, apparently enjoying the feel of Rachel's flesh. This went on for a short while, before Matthew made another request. "Kneel down for me?" He asked curtly.

Rachel looked at him pleadingly. "I... This is really embarrassing."

"I'll tip." Matthew reminded her.

Rachel looked up, straight at the hidden camera, and shot me a little look that said something like "Sorry, but I don't know what else to do." She then lowered herself to her hands and knees, kneeling down before Matthew, ass pointed at him. This gave Matthew a perfect view of her pussy, which was now poking out between her thighs from the rear. Matthew locked his eyes on this, leaned back and started jerking off -- hard.

Rachel just knelt there, frozen. She was presenting her ass and pussy to Matthew like a dog in heat, and she must have felt like a piece of meat. Matthew was certainly treating her as such. He wasn't talking to her, touching her, or really interacting with her in any way. He just stared at her like a sex toy -- a stripper -- a whore -- and masturbated as if she wasn't even in the room. Rachel was blushing furiously, but she complied with her customer's wishes, and knelt there obediently, pussy and ass pointed at Matthew for his viewing pleasure. Matthew was now tugging away at himself so quickly that I figured the end was near.

Or perhaps not. Matthew suddenly slowed down dramatically, now slowly stroking his cock up and down the entire shaft. He continued staring at Rachel's ass and pussy -- still dutifully presented as she knelt before him -- his mouth slightly agape, a lustful look in his eye. He had been ignoring Rachel for the past several minutes, save for his obvious focus on her naked flesh, but now finally spoke up.

"So uh... would you do something for me?" Matthew asked.

Rachel looked uncomfortable. "Umm... Maybe?" She replied.

Matthew stepped out of his pants and stood up, walking across the room until he and Rachel were on opposite sides of it. "Come here please." He instructed.

Rachel, a confused look on her face, started to stand up, but Matthew interrupted her. "No -- don't stand. Just... crawl over here, please."

Rachel shot another pouting glance at the camera. Matthew certainly had some fetishes, and they all seemed to involve the degradation of my wife. I actually expected Rachel to object, but, much to my surprise, she simply started doing it -- crawling over to him on her hands and knees. The sight of Rachel doing this was overwhelming, and I felt myself get hard as I watched her slowly and seductively crawl over to Matthew, ass swaying. Matthew started masturbating again, slowly but firmly moving his hand up and down the full length of his cock, eyes locked on Rachel who crawled over like a dog. Rachel was blushing furiously and couldn't bring herself to make eye contact with Matthew or the camera, and she just stared at the ground, shamefully embarrassed. And yet she complied, growing ever closer to Matthew. When she arrived, Matthew stopped touching himself, and pointed his cock at her, a clear invitation. Rachel almost rolled her eyes at the rather obvious message, but instead just wordlessly raised herself up to take him back into her mouth, leaning forward, and supporting herself on her hands, ready to suck his cock once again.

She didn't have to wait for long. Matthew reached down and guided his cock to the base of her mouth, then pressed it in slowly, while using his other hand to stroke Rachel's cheek. Rachel obediently wrapped her lips around his cock, forming a tight seal, and resumed sucking on it, going down almost his entire depth, before sliding her mouth back up off of it, slurping and gagging slightly. Matthew just stood there, staring at her, seemingly in bliss.

Rachel went on like this for a few minutes -- kneeling in front of Matthew, supporting herself on her hands and knees, pleasuring him with just her mouth -- but after a while reached up to start assisting with one of her hands. She was in her element here, using the same tricks on him she used on me -- moving her mouth and hand together in tandem, stroking the base of Matthew's cock while sucking on the tip. I knew from experience that it felt great, and I watched Matthew with jealous envy. She carried on doing this for a while -- honestly, I lost track of time, but I'd guess somewhere between 5 and 10 minutes -- before eventually slurping her mouth up off of his penis and looking up at him, still stroking him with her hand.

"Something wrong?" Matthew asked.

"I..." Rachel blushed. "My jaw hurts."

"Oh." Matthew replied. "I suppose you have been at this a while." Little did he know -- he wasn't even the first tonight. "Still," he continued, "I was hoping to cum..."

Rachel, always the trooper, replied "don't worry -- just let me catch my breath." She kept stroking him. "Why don't you tell me about where you want to cum when you're ready." It was a nice move, since it kept Matthew engaged while giving her a break.

"Oh... um... I just figured I'd cum in your mouth. You swallow, right?" She didn't, normally. I mean, it's not like she never did, but she really didn't like it, and it was a rare event. Still, I wondered if she would do it for him. My question was soon answered, as after a brief pause, Rachel replied "oh... yeah, sure. Of course."

"Great." Matthew said with a bit of a smile. "You're really excellent, you know." It was the first indication of any enjoyment he'd given Rachel all night, and to my surprise, Rachel seemed very encouraged by it. She looked exhausted, but she smiled, as if with a real sense of accomplishment. "Thanks -- I appreciate it." She said.

"Hey, if you need a break, can I fuck your tits?" Matthew asked suddenly.

Rachel hesitated, and looked a bit uncomfortable, but I guess concluded it was a reasonable request. Her breasts weren't huge, but they were big enough that if she held them together, there would be something for Matthew to fuck. Wordlessly, she raised herself up, remaining on her knees but lifting her ass off her feet, and pressed her tits around Matthew's cock, enveloping it. She looked up at him with a sultry gaze, inviting him to use her as he pleased.

"Oh, uh... one second." Matthew paused for a second, then spat a pretty impressive wad of saliva between Rachel's breasts. Rachel's face was a mixture of confusion and disgust, but Matthew quickly explained: "it would hurt otherwise."

Rachel looked a bit repulsed, but smiled. "Um... Thank you", she said softly, still looking up at him. Matthew said nothing further -- he just began thrusting, sliding his dick up and down Rachel's tits while Rachel just knelt there, once again reduced to a piece of meat.

Rachel and I had never done this before, and I imagine she must have been feeling pretty weird, but if she was, she gave no indication. She just knelt there, dutifully pressing her tits together for Matthew, who was now fucking her tits long and hard. It was an obscene site, seeing the woman I loved assume the role of a submissive harlot. But it was a role she played surprisingly well, and she was satisfying Matthew's every desire.

After a few minutes, Rachel looked up at Matthew, and asked sweetly. "May I?

"Oh, of course." Matthew replied. He stopped thrusting, and Rachel let go of her tits, which bounced down and hung off her chest. I now had a good view of her nipples, and I was surprised at how hard they were, but I set the thought aside. Rachel lowered herself down, sliding her mouth back over Matthew's cock, which she almost devoured. She was forcing her throat down over it, taking him all the way to the back of her mouth, pressing her nose into his pubic hair, then sliding all the way back up, only to go down once again. She was inhaling him, and I could see on his face that he was in ecstasy as his cock pushed further and further down her throat. It was a blowjob like I had never seen Rachel give before, and I was tremendously envious, but I understood -- she was looking to end it.

Unfortunately, despite her best efforts, she just couldn't seal the deal. It certainly wasn't a lack of enthusiasm, or sexiness -- Rachel was deep throating Matthew like a porn star, and the sound of his cock hitting the back of her throat as she gulped it down was incredible -- but Matthew just refused to cum. Eventually, Rachel broke her rhythm and slid Matthew's cock out of her mouth, whimpering a little. "I... my poor jaw..." She whined.

"I'm close." Matthew encouraged her.

"I'm sorry. I really need a break. Do you mind if I grab some water?" Racial asked.

"Oh, sure, of course." Matthew replied. "Although if your mouth is really sore, can I just finish in your pussy?"

"I, no I..." Rachel stammered.

"I'll give you $300." Matthew blurted out. "You're the most perfect woman I've ever seen."

I was shocked. This wasn't the plan -- we settled on blowjobs precisely so that Rachel wouldn't have to truly get intimate with any of her clients. But on the other hand, $300 was a lot of money, and I actually wasn't sure whether Rachel could finish Matthew off with her mouth in her present state. She wasn't used to sucking this much cock, and she'd been at it all night. I felt the butterflies grow in my stomach as I wondered what she would do.

"I... I've never done that before -- been paid for sex, I mean." Rachel replied.

Matthew looked surprised. "Aren't you basically doing that now?"

Rachel looked embarrassed. "It's different..." She said softly.

"It's up to you. Although when I paid for your services, I really figured it included an orgasm..." Matthew trailed off.

Rachel smiled weakly. "Yeah, and understand. Can I... Can have a minute to think?"

"Of course." Matthew replied. At that, Rachel walked away, and headed to the part of the apartment where I was hiding in the closet. A moment later, she opened the door to my hiding place, and mimed a gesture that clearly asked "what should I do?"

Rachel was a sight to behold, seeing her now in person, rather than through the limited resolution of one of my cameras. Her lips and mouth were covered with pre-cum and saliva, which ran down her chin, and even a bit onto her breasts. Her breasts glistened from where Matthew had spat on her and fucked them, and her nipples were immensely hard. She looked like exactly what she was -- a whore. To my surprise, though, this didn't bother me. It actually turned me on, and I desperately wanted to take her to her bedroom and fuck her myself. Sadly, I would have to wait -- I mentally returned myself to the task at hand.

She was considering fucking him. I wonder if she just wanted to fuck him, which was why she was here asking for permission. Based on how hard her nipples were, she was enjoying herself. Although I suppose that wasn't fair -- she was being used like a sex toy, and I guess it's not really surprising she had a physical reaction to that. Hell, I was having a physical reaction to watching her. And she was being offered a lot of money -- enough money to really help carry us next month.

I shrugged my shoulders and mimed back my best "I don't know!" I really didn't. I wasn't comfortable with the idea of her having sex with him, but it was a lot of money, and she'd already come so far... did this extra step really matter? In any event, I decided to leave the decision up to her, giving her my permission, if not encouragement.

Rachel looked sad, and mouthed "I love you." I looked at her, surprised, but nodded. I understood -- she was going to do it. She silently shut the door, and walked to our bedroom -- I guess to grab a condom -- then headed back to the main room, where Matthew was waiting. She held out the condom to him, and just said "okay."

"Oh wow." Matthew said, and I saw him break out into a smile. But then he added, "do I... do I have to wear this?"

"Yes!" Rachel almost shouted. "I'm... I'm sorry." Rachel said after a moment. "I really don't normally do this. Sell my body, I mean. But yes, please wear it."

"What if I pay you $500?" He asked after a moment, before quickly adding "like it says on my profile, I'm STD free. I just got tested a week ago." He paused. "Wait, you're STD free too, right? You said this is your first time doing this?"

Rachel nodded. "Yes, totally clean, but... I don't know... I..."

"It feels a lot better without a condom. It'll probably be faster." Matthew proposed, as if Rachel were unfamiliar with the mechanics of condoms.

Rachel looked at Matthew, then stared at the floor, then looked back at Matthew, the averted her gaze once again. She blushed furiously, and kept her eyes glued to the floor. "Okay. $500. You've got a deal."

I blinked twice, stunned. Not only was Matthew going to fuck my wife, he was going to cum inside of her. Still, I couldn't blame Rachel. Given what he was offering, it was the right choice.

Matthew instantly pulled out his phone and fidgeted a bit, before looking back up at Rachel. "Done." He pronounced.

Rachel looked up at him nervously. "Really?" She asked.

"Check your account." Matthew replied.

Rachel grabbed her phone and looked at it for a minute, before putting it down. She breathed deeply -- there was no turning back now -- and looked at Matthew. "Do you want to come to the bedroom?"

"Sure, great." Matthew enthused. "Would you... Would you mind crawling there?" He requested.

Rachel blushed even harder at the request, but after a moment, just lowered herself down onto her hands and knees, and started crawling once again. Matthew walked behind her, eyes glued to her ass, which swayed with her every movement.

Our apartment is small, and it didn't take long for the two of them to arrive in the bedroom. Rachel looked up at Matthew, her hands and knees staying firmly planted on the floor, and asked him "any preferences for how we do this?"

"Oh, um, no." He said after a moment, seemingly embarrassed. "This is actually... This is sort of my first time."

Rachel looked shocked. To be honest, I wasn't that surprised.

"Really?" She asked.

Matthew looked really embarrassed. "I mean, I've paid for blowjobs before. And I've watched a lot of porn. But I've never had sex with a real woman."

I almost laughed. It was so delightfully awkward, I almost forgot that it was my wife, whoring herself out to pay the rent. I waited to see how Rachel would respond.

"I..." Rachel paused, still surprised, and apparently unsure how to proceed. After a moment, she spoke up again "Okay, umm... Just give me a second to get ready..."

Rachel raised herself up off her hands and knees and climbed onto the bed, positioning herself in the center, and lying back. She blushed a little and looked away, rolling her head to the side to avoid Matthew's gaze, then spread her legs open, pulling her feet in and raising her knees up before spreading them apart -- wide. Matthew now had a perfect view of her pussy, a fact that wasn't lost on him -- he stared at it intensely, and I think I even saw him lick his lips. Rachel slowly reached a hand down between her legs and started rubbing her clit, softly and slowly, moving her hand up and down her pussy. She started breathing a bit more heavily, stimulated for the first time after a night of being used by others, and after a few seconds, I heard her moan softly. Matthew reacted to this -- his cock sort of pulsed up -- and he reached down and started stroking it, staring at my wife and masturbating once again.

Rachel was now trembling a little, and taking short sharp breaths. I think this might have been the most embarrassing part of the evening for her -- having to pleasure herself while she knew two sets of eyes were glued to her, watching her every move, sharing her every feeling, as she got her body ready for her final act: her deflowering. She let out a loud breath as she slid a finger down and gently inside her pussy, pushing it in slowly, then pulling it out, returning to her clit, which she now rubbed more aggressively. For his part, Matthew just kept stroking his cock, and was now once again masturbating furiously.

It took a few minutes -- Rachel slowly warming herself up, Matthew just staring at her lustfully and jerking off -- but Rachel finally looked back at Matthew and announced, softly, nervously, trembling "okay..." she almost whispered "I'm ready." She lay there with her legs open, pussy sopping wet, waiting for Matthew to take the next step.

Matthew looked like he had been shot out of a cannon. He almost leapt onto the bed, positioning himself over top of my petite wife, who giggled awkwardly. "Hey, relax." She said, placing her hands on his chest and rubbing him gently.

"Shit. I'm sorry. I'm just -- it's finally happening." Matthew replied, unable to contain his excitement.

Rachel smiled at him. "Relax." She encouraged him. "You need to build up slowly."

Matthew just grunted -- I'm not kidding, he actually grunted -- and excitedly grabbed hold of his cock and positioned it at the entrance to Rachel's pussy. Rachel twitched as it made contact -- excited? nervous? I wasn't really sure -- then slowly looked up at him with a sultry glance. "Please be gentle." She asked softly. "I'm delicate."

Matthew grunted again, but seemed to respect to the request. He was now straddling Rachel, her knees still up near her hips, her legs widely parted, feet in the air. The contrast between his tall lanky body and her own petite beautiful form was a strange sight, and I saw him start to press himself into her, penetrating her, filling her, having her. I saw Rachel wince slightly and roll her eyes back, moaning softly, as Matthew slowly but surely pressed deeper and deeper inside of her, gradually lowering his weight onto her petite frame. At this point, his long but narrow cock was buried about halfway inside Rachel's pussy, who winced a little as she moaned. "Unh... that's a bit too deep."

"Oh, I'm sorry." Matthew replied tensely, embarrassed. He pulled out almost comically quickly, but it was endearingly respectful, and my wife smiled again.

"Don't worry," she said after a pause, "I'm fine. And you feel great. Keep going." She encouraged him.

Matthew smiled wide. "You're really great at this." He slowly started thrusting his cock back into her, eliciting a sharp, high-pitched moan. "Oh!" She exclaimed. I couldn't tell if it was delight or pain, or a combination of both, but she was certainly feeling something. This was to be expected, I suppose; Matthew's cock was noticeably longer than mine, albeit skinnier, and thus the longest one Rachel had ever had. As he slowly thrust inside of her, he was stretching her more deeply than she had ever been stretched before, and you could see it on her face.

Matthew was building up a rhythm, thrusting himself a little more deeply inside my wife each time. He was now up to about three quarters of his length, and Rachel was breathing heavily. The two made eye contact, eliciting a soft giggle from Rachel, who reached up and stroked Matthew's face softly. "Kiss me." She instructed him. Matthew was only too happy to oblige, and he leaned in, locking lips with her, still slowly but surely thrusting his cock further and further into her pussy.

'Kiss me?' I thought to myself. This was making me a little jealous again. Although I had to admit, Rachel looked incredibly sexy as she got more and more stretched out by Matthew. I wondered if Matthew was a good kisser. I doubted it, but something seemed to be having an effect on Rachel, who wrapped her arms and legs around him -- enveloping him -- and pulled him into her. At this, Matthew thrust his cock the rest of the way in, causing Rachel to moan loudly. "Okay." She said softly, after a moment. "You can go harder now."