Debt Collection Pt. 05

If you're new to the story, please start at chapter 1.

For an easier reading experience, I've combined two chapters into one, so this one's a little longer.

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***

I had more exciting experiences again over the next two weeks. On some days, I would engage in more roleplay with Mr. Goldman, letting the perverted professor play with my innocent, teenage body. On other days, I let Bruce fuck me roughly in Amy's sex chamber so we could tease the bound, orgasm-starved Alex. I even ran into Lily's fiance in the hallway twice, and like the good little girl I was, I let him fill up my mouth with his creamy load both times.

I also had regular sex with Jake. However, I felt angst and uncertainty toward him. We had agreed to be sex friends, but that arbitrary distinction did nothing to dull the romantic chemistry we had together. He would often have sex with me in the missionary position, kissing me tenderly as he thrust into me, and it drove me crazy for him. He would stare deeply into my eyes during sex, and I would find myself lost in a beautiful trance.

When I had sex with other men, my mind often wandered to Jake, and I let my imagination run wild. For instance, whenever Mr. Goldman chained me up and defiled my innocent body, I imagined it was Jake instead who was training me to be a slutty pleasure slave. I would come over and over, my needy body lusting after Jake's touch.

One particular day, near the end of Alex's imprisonment, I went to have sex with Jake at our usual time. I came to his room wearing a cute black dress and strappy heels, an outfit that I knew would make him instantly hard.

But something felt off. Our conversation felt stilted, and Jake could barely look me in the eye. His kisses weren't as passionate, either. When we began to have sex, Jake couldn't cum, or stay erect for more than a minute. Finally, we just gave up.

"Am I doing something wrong?" I asked as he pulled out of me. "Do you not like me anymore?"

Jake sighed. "That's not it," he said. "Something's just been bothering me recently."

"What is it?" I asked.

"Yesterday, I was talking to Lily, and she told me that you and Francis had done a hot bondage roleplay together. She thought that I might find it sexy, so she asked if I wanted to see the video." Jake stared down at the floor. "I guess out of morbid curiosity, I said yes."

I felt a weird tightness in my chest. "Okay. Keep going."

"Yeah. So I watched the whole thing. It was hot. But at the same time, I just felt so unbelievably jealous. I watched as you orgasmed all over his cock and I thought to myself: I need Angie to cum. But she doesn't need me to cum. She can just have somebody else get her rocks off for her. And I'm not trying to say that in a slut-shaming manner. It just... made me feel like you didn't need me."

"I was just acting," I said.

"It doesn't make any difference," Jake said. "I just can't be your sex friend anymore. I like you more than a friend, Angie. I can't stop thinking about you."

My throat felt constricted. "Can I admit something, Jake?"

"Sure."

"Each time I had sex this week, I was fantasizing about you," I said.

Jake blushed. "Really? Why?"

"Because I..." The next words were on my tongue, and I barely managed to spit them out. "I have feelings for you. That's why I'm sorry," I turned away, trying to cover my eyes, which were filling with tears. "I can't date you, Jake. I still have loans to pay. My sister is working hard to do that, and I can't just let her do that alone."

"Wait, Angie," Jake said. "I've been thinking about it, and there's a way we can date while paying off your loans at the same time. I can use Alex's money."

"What do you mean?"

"Whenever I report to Lily that I've had sex with a girl, it goes on Alex's tab. So I can just report to Lily that you and I are having lots of sex."

"Oh. So you'd be my only customer." I thought about it. "Didn't we have this discussion a couple of days ago? There were some issues with that plan, right?"

Jake nodded. "Well, once Alex realizes that I'm using his money to fuck you, he might want a piece of the action. He'll also probably feel a little lonely just fucking girls by himself. He said having me around helps him stay grounded, or something."

I giggled. "Why does Alex need a 22-year old boy to keep himself grounded?"

"I have no idea," Jake said, grinning. "What a mess. It's like he's perpetually in a midlife crisis."

We laughed for a bit more, feeling much of the previous tension between us disappear. Then, Jake stared at me, searching my expression carefully. After all, I still needed to give my answer. Having made up my mind already, I kissed Jake lightly on the cheek.

"Okay. I'll be your girlfriend," I said. "We'll find a way to deal with Alex, I'm sure."

He hugged me tightly in response. "Thanks, Angie."

I took a deep breath. "Yeah. I just know I can't sleep easy knowing my sister is still working here. We need to siphon Alex's money as fast as we can."

"I'll always be there to help you out," Jake said.

I smiled at him. "Perv."

Jake pulled my body up against his chest and kissed me. His lips were firm and aggressive, and I let out a couple of moans as he lightly sucked on my tongue and lips.

When we finally pulled away, I said breathlessly, "Let's get the fuck out of this building."

***

After I quit prostituting myself at the Debt Collection Agency, I went back to working at the aquarium. Finally, I didn't have to worry every day about running into my sister at the loan agency. Life felt easier, and dating Jake helped.

Every day, I would bike to Jake's apartment after my shift ended at the aquarium. We would watch a movie or TV show, and then have a session of intense lovemaking afterward in the privacy and comfort of his bedroom. He was simply insatiable, and I loved it. We would fuck into the early morning hours and I would wake up late, biking back home with a sore but satisfied body.

Eventually, Tessa realized that I had a boyfriend.

"Who's the lucky boy?" she asked me one day, as I returned one morning from Jake's house.

"We've only been dating for a week," I said. "Don't scare him off, Tessa."

"I won't," she said. "You don't even have to tell me his name. Just tell me what he's like."

I sighed. "Fine. He's a little nerdy, a little socially awkward. But he's really sweet. And..." I thought about him thrusting up into my naked body, as I moaned out his name over and over. "He's a really good kisser."

"Aw," Tessa said. "You are so into him. It's cute."

As the weeks passed, my relationship with Jake progressed smoothly. I began to feel like I was finally having a normal sexual life — well, except for one little thing. At the end of each day, Jake and I would report our sex sessions to Lily, and it was recorded on Alex's tab.

"Are you and Jake a thing now?" Lily said as we called each other one day. "You've been doing nothing but have sex with him lately."

"Yeah. We've decided to date, exclusively. Though, Alex is still paying for all the sex Jake's having with me."

I heard some laughter over the line. "Keep sucking Alex dry, girl. You are doing what God should have been doing all these years. Though I have to say, I've missed you."

"I know, Lily. I miss you too."

"I've been watching your sex videos nonstop since you stopped coming here. They're so damn hot. If your current career aspirations ever fall through, just know I took a couple of film classes in college. I could edit your sex scenes into a piece of art."

"Oh, shut up," I said, blushing. "Well, if you miss me that much... maybe I'll see if I can open our relationship just a little bit."

There was a pause over the line. "Really?"

"Yeah. But I have to ask Jake. We're probably going to have another complicated conversation about relationship boundaries. Speaking of open relationships, how do you deal with those? Like, with you and your fiance?"

"I don't think I know the answer to that, really," Lily said quietly. "James and I broke up a week ago."

"What?" I said. "Really?"

"Yeah. We had a complicated conversation, and James said he wasn't ready for a long-term relationship," Lily said.

I felt a little guilty. After all, I had sucked her fiance's cock twice, and he had liked it enough to cum in my mouth both times.

"I'm sorry. You two seemed happy," I said.

"It's fine. Shit happens," Lily said. "I've been keeping myself distracted with the usual vices. Though, they don't seem to help. I've never cried during sex before."

"Aw," I said. "I'll ask Jake if you can come around, then. And if he says yes, I'll do my best to cheer you up."

"Thank you so much, Angie," Lily said. "Let me know."

"I will."

***

That night, when I visited Jake, we watched a movie together. And in the middle of the movie, I decided to spring that awkward conversation with him.

"Would you be okay if Lily... joined us as a third one day?" I asked. "Like, for sex?"

"What?" Jake said. "Why does she want to be our third?"

"Oh, she misses me a lot," I said. "We're pretty good friends now."

"Oh. I mean, I'm okay with a threesome," Jake said. "I just didn't expect that. I just figured she'd find us... boring. We're pretty vanilla."

"Well, she's currently going through a breakup," I said. "So she wants something more affectionate."

"Okay," Jake said. "Do I have to fuck her?"

"Probably not. I think she wants to play with me. But don't worry, she's not gonna steal me," I said, grinning. "I just see her as a friend."

Jake thought about it. "Okay. I mean, we can try it and see how we feel. But if we feel uncomfortable, we should probably stop."

I nodded. "Okay. That sounds like a good idea."

I was excited. To be honest, I had missed Lily as well. I hadn't seen her for a while. I told Lily the good news, and we scheduled a date on the weekend for her to come to Jake's apartment.

Memories of Lily licking my nipples and teasing my clitoris kept my pussy wet and excited the night before. When I woke up, I still felt unbearably horny. So I went to the bathroom and masturbated to the memory of Lily dressing me up in various naughty outfits, fondling my breasts and fingering me as she did so. After I was finished masturbating, I called up Lily.

"Hey, could you bring some sexy outfits tonight?" I told her. "I want to look really hot for Jake and you."

"Sure!" Lily said. "Also, how much money do you want for tonight?"

"Don't worry about it," I said. "We're doing this as friends."

Lily laughed. "Angie, you're being too nice. I just like helping girls out with their loans."

"I'm telling you, don't worry about it," I said. "I'm not going to treat you the same way I treat Alex."

There was a pause over the line. "Aw, that's so sweet. I'm glad you feel that way. Honestly..." I heard Lily sniffle in the background. "I like you a lot."

"Is this a romantic confession?" I teased.

"Of course it is," Lily said, laughing. "Alright, see you later. I can't wait. Love you, Angie."

"Love you too," I said.

As I hung up, I began to finger myself again, feeling a shiver of anticipation run down my body.

***

That evening, I came to Jake's apartment feeling more worked up than usual. I was looking forward to seeing what kind of outfits Lily would bring to dress me up in. After all, I hadn't fucked Jake in anything too scandalous, since my wardrobe was so tame. When I finally climbed out of this debt hole, I hoped I could purchase some more fashionable clothes for myself.

Lily arrived a few minutes after me, and I opened the door for her. She was dressed in a sheer white T-shirt that revealed a black bra underneath, along with a short black skirt that showed off her bare legs. "Damn," I said. "You look great, Lily."

"Don't I?" she said. "Some old men were staring at me in the parking garage, and I thought about giving them my business card." She laughed.

Jake came out of his bedroom. He was dressed in his usual plain attire, a T-shirt and baggy jeans. It was a shame he didn't wear tighter clothes, I thought. Those attractive girls who bullied him in high school would probably be lining up to suck his dick if they could see how toned his body was now.

"Hi, Lily," Jake said. "How ya doin'?"

"I'm doing okay," Lily said. "I'm still pretty sad about the breakup, but I've been looking forward to tonight." She showed us the bag in her hands. "Now, let's get Angie dressed up."

We spread out the outfits on the table. Lily had brought some sexy lingerie sets, along with some cute skirts and tops. But one particular outfit caught my eye. It was a sexy security guard outfit.

"Can I try this on?" I asked Lily.

"Sure," Lily said.

First, I put on the skintight blue dress. It was short enough to reveal most of my thighs and barely covered my ass. A zipper ran up the front of the dress and even fully zipped up, the dress still revealed much of my cleavage. Decorative pockets had been sown on the breast cups, and above the right pocket was a badge that said "Security". There was also a black belt on the dress which ran across my hips and above my ass, and it allowed me to adjust the tightness of the dress around my waist. Hanging from the belt was a pair of handcuffs, which I thought was a cute touch.

"The dress is so short," I said, staring downwards at my bare thighs.

"Yeah," Lily said, bending down to adjust the ends of my dress. "I like it, though. Your legs are beautiful."

Jake was staring intently at my body, his hungry eyes traveling all over my ass and tits. I smiled, turning away to wiggle my butt for him, and I swore I heard a quick intake of breath behind me.

"Don't get too excited, you two," Lily said. "We're still not done with the outfit."

I nodded and took the black stockings that had been included with the outfit. As I bent over and slowly slid the stockings on, I caught a glance of Jake admiring my stocking-clad legs. He quickly looked away, feigning indifference. God, I loved teasing Jake. His reactions were just too cute.

A pair of heeled, ankle-high black boots finished off the outfit. They made my feet look petite and sexy. I stood up and glanced over at Jake and Lily. "What do you guys think?"

"God, you're sexy. I want to see you get fucked right now," Lily said.

She pulled me against her and kissed me. I moaned in surprise, feeling the warmth of her full, round breasts on my chest. Meanwhile, Jake positioned himself behind me, pressing his hard bulge against my ass. He reached around my waist and began groping my breasts through the dress, catching my nipples between his fingers and teasing them.

"Mmm... Jake..." I moaned.

My body continued to melt in his grasp, my pussy already lubricating itself. His hands had roamed around to my ass, admiring its feel through the blue dress. Meanwhile, Lily reached for my belt and took the handcuffs, winking at me. "Put your hands behind your back," she said.

I nodded and did so. Lily handcuffed me, tightening the cuffs on my small wrists. I struggled playfully. "It's a little uncomfortable," I said.

Jake's hands were roaming around my ass, and as he heard my words, he slapped one cheek. I yelped in surprise, and he whispered in my ear, "That's what you get for being a tease." He bent down and ran his hands down my stockinged legs, enjoying the feel of them on his skin. "Let's bring you to the bedroom," he murmured.

Jake and Lily led me by the arm, handcuffed, to the bedroom. Jake sat down on the bed, and ordered, "Get on your knees."

I did as he asked, feeling a little tingle in my pussy at his sudden assertiveness. Behind me, Lily also knelt, and I felt her breasts press up against me as she embraced me from behind and groped my breasts eagerly. At the same time, she lightly kissed the back of my neck. As I moaned, enjoying Lily's ministrations, Jake took off his pants, revealing his gorgeous cock.

I knew what he wanted, so I took the head of his cock into my mouth, sliding my tongue all over the engorged head. As I sucked him more fiercely, Jake pushed my head further onto my cock, throwing his head back in ecstasy as his dick tickled the back of my throat. "Oh fuck, Angie," he sighed. "That feels good."

He let go of my head and I quickly came up for air, coughing. I glanced back at Lily, who was fingering herself under her skirt, panting in desire. "Enjoying this?" I asked.

Lily nodded, showing me her drenched fingers. "I want him to fuck you. Don't let me get in the way, though. I'll just watch."

I gave her a quick kiss. "If I see you looking lonely, I'll come over and lick your pussy until you cum."

Lily smiled and helped me stand up. Reaching under my dress, she slid a finger into my dripping wet pussy, then pulled out. "Angie's more than ready, Jake. It's time to fuck your sexy little officer."

I saw a raw sexual desire in Jake's eyes that I hadn't seen ever since I had worn bridal lingerie for him. He pushed me facedown on the bed so my ass was sticking up in the air, my handcuffed wrists crisscrossing over my back.

"Her butt looks unbelievable in this dress," Jake said. "You have great taste, Lily."

"Aw, thank you," Lily said. "If you ever want to dress up Angie in a sexy outfit again, call me."

"Well, I guess I'll be calling you all the time, then," he said, and I smiled to myself.

Jake slid the hem of my dress over my ass, revealing my naked pussy. He slowly maneuvered the head of his cock into me, and I let out a whimper as he stretched my entrance. He wasn't giving me as much cock as I wanted, though, and soon my whimpers became frustrated.

"Stop teasing me already," I moaned. "Give me all of it. Please."

Finally, Jake shoved his cock into me and began to move back and forth. I moaned into the bedsheets, feeling Jake's big cock rub against my sensitive inner spots. His cock was an utter force of nature, and considering Jake could only get hard to me, it made sense why it was so huge right now.

"God, Angie... you're so hot," Jake said, groaning in pleasure as he thrust in and out of me.

"You love it when I dress up in uniform, don't you?" I moaned.

"Yes," he said, squeezing my ass. "I'm so hard right now."

"I can tell," I whimpered. "I'm losing my mind...your dick feels so good inside me."

I groaned as Jake thrust into me harder from behind, my face pressed against the bedsheets. As I was handcuffed, the position felt quite uncomfortable, but the discomfort just seemed to add to the erotic sensation of Jake fucking me forcefully, punishing me with every inch of his cock.

On the other side of the bedroom, Lily lounged on Jake's chair, watching us, her expression one of ecstasy as she finger-fucked herself. She seemed quite close to orgasm already, and I figured the sudden stimulation of seeing me get fucked, in a sexy outfit like this, had almost pushed her over the edge.

"Wait for a second, Jake," I said. "Lily looks like she's close to coming. Let me finish her off."

He pulled out of me and helped me off the bed, but not before giving me a long, passionate kiss. After we pulled apart, I walked over to Lily, my black heels tapping against the wooden floor.

"Wait, Angie," Jake said. "Let me do something that I think Lily will enjoy."

I wasn't sure what he was talking about, but I stood right in front of Lily's face, waiting for Jake to do something. The first sensation I felt was his hands on my thigh, running down my stockinged legs.

"What are you doing?" I said, moaning a little at the ticklish sensations. "Oh!"

My yelp came from him massaging the back of my thighs. He then pressed his face against my supple flesh, tickling my thigh with his facial hair, and I began laughing uncontrollably. "Stop! You horny little... piece of shit."