Freedom Comes at a Price Ch. 04

Story Info
Darren's tasks continue.
4.7k words
4.09
19.2k
4

Part 4 of the 4 part series

Updated 09/22/2022
Created 01/13/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

I was still laying on my front, my face in the pillow, when I felt Rachel sit on the edge of the bed. I kept my face hidden, partly through the shame of letting some strange man fuck my ass but also because I realised that I had enjoyed it more than I should have. I had never thought I would experience gay sex and I had certainly never cum as hard or as much as I did as when I filled his ass for him.

Suddenly I felt a cold liquid being poured onto my sore ass and thought that Rachel was preparing me for another ass fucking but, instead of opening me up, she began to rub the liquid in my cheeks. The liquid was soothing and I squirmed a little as she continued to rub it in.

"Soon feel all better Darren." She whispered into my ear.

"Why did you make me do that Rachel?" I asked her.

"Because I need to know how serious you are about being freed and with me." She answered. "And tomorrow night you will have completed the second task, it should be easy now."

I couldn't believe what I was hearing. She was expecting me to perform for her, because that's what it felt like I was doing, as quick as possible. It seemed to me that she was more desperate to get the tasks finished than I was.

Still she was right about the next task, which definitely would be a lot easier, providing she brought the right person home.

Once she had finished soothing my ass she got up, put my callipers back on and chained me back to the bed.

"Don't worry you will be undone again for the second task." She said and left the room, shutting the door as she went.

Once again I was alone, naked, and chained to her fucking bed. I didn't care that she was in the house and began struggling with my restraints again. If she heard me what was the worse she could do, fuck me with her monster dildo or whip me. I knew she wouldn't do anything worse because she, apparently, wanted to desperately be with me and I'd be no good to her dead. I moved as much as I could, trying to get comfortable, when the TV at the end of the bed flicked into life again.

Although I was shattered, my whole body ached and I just wanted to sleep I couldn't help glancing at the screen. I thought she would torture me by putting on the video she had made when testing her equipment, but I was wrong. Instead the first image I saw was Matt sitting down next to me, begin kissing me and starting to stroke my cock.

Instead of being repulsed I lifted my head as much as I could and continued to watch.

The longer I watched the harder my cock became and, not noticing that the red lights on all the cameras had come on, started to copy Matt's actions and began to stroke my cock. I never took my eyes off the screen, or sped up my wanking and was soon watching myself sucking Matt's cock and swallowing all his cum.

My wanking had become more intense by the time I was watching my cock slide into his ass and, seconds later, I came all over my chest. I was still milking the last drops from my cock when Rachel burst into the room.

"I think someone secretly enjoyed Matt's thick, juicy cock didn't they?" She said.

"Rachel I didn't hear you come in." I said.

"You might not have heard me come in." She said. "But I just watched you cumming."

"I couldn't help it." I said trying to think of an excuse.

"Don't be all apologetic." She said. "It turned me on so much watching you that I had the most intense orgasm I have had for days."

"I thought you would be mad at me for doing it when you weren't here."

"At first I was but as I watched you I got more and more turned on." She said. "And I just had to watch you finish."

Relief washed over me when I realised that nothing bad was going to happen, and relaxed on the bed, cum running down over my chest. Rachel also noticed this and lowered her head, licking it all up, before passionately kissing me. I didn't gag at the taste this time, I actually found it quite nice, and kissed her back hard.

"I think I better get the second task arranged as quickly as possible." Rachel said once our lips had parted.

"So do I and make sure you find another good partner." I answered. "And trust me these restraints aren't needed anymore."

"Very clever Darren." Rachel said, jumping off the bed. "Fancy thinking you could trick me."

"I swear I'm not trying to trick you." I told her, and I wasn't. "If our life together is going to be like this you can count me in."

"I think I'd sooner wait to see if you complete all the tasks first." She said and stormed out of the room.

This time she didn't shut the door and I looked back at the screen. The video of Matt and me was no longer playing, instead it had been replaced of my wanking. I looked at the screen and saw myself cumming but didn't feel anything like I had when I was watching the other video, and turned my head away.

Rachel came back in, having calmed down a lot, and sat back on the edge of the bed with her back to me. With my free hand I reached out and began to stroke her back, but she shrugged me off. Unperturbed I reached again and this time she sat there letting me.

"Why did you have to try and trick me Darren?" She asked.

"Believe me Rachel I wasn't." I said. "And I will prove it to you before you do release me, if that's what you want."

"In a way I do want to release you." She said, her voice breaking with emotion. "But I'm scared you will leave and go to the police, I just need to be sure."

"In that case I suggest you find me task two quicker than you had planned." I said and let my hand fall.

Once I was no longer touching her Rachel turned to face me, and ran her hand over my chest. My cock twitched as she went lower and, very quickly, she had wrapped her fingers around me.

As she began to stroke me I placed my hand around hers and we did it together, slowly, and soon I had cum over both our hands. Rachel looked at me and lifted her hand, going for her mouth, but I stopped her. I lifted mine and reached towards her and, as she licked the cum from the back of my hand, I took hers and did the same before leaning in and kissing her.

"I'll tell you what Darren." She said licking her lips. "If you do the second task good enough I'll forget the third and we shall go straight to the envelope."

"Are you sure?" I asked slightly disappointed as I knew what the third task was supposed to have been.

"Yes Darren totally sure." She told me. "We could always do task three together one day."

She then lay down next to me and, as I put my arm around her, moved closer to me and we both fell asleep, and didn't wake until lunchtime the next day. When we did finally wake my cock was as hard as ever and Rachel was pushing her ass against me, almost like she was trying to get it inside her. I reached down, finding that she had unchained my other hand when I was asleep, and taken everything except her underwear off, and pulled the thong she was wearing to one side gently.

I nudged my cock forward, trying to find her pussy, when Rachel reached down and grabbed my cock.

"Not my pussy Darren." She said and rubbed the end of my cock against her ass.

Without lubrication it took a few goes but, eventually, my cock managed to penetrate her. She moaned loudly as I continued to push deeper into her ass, until my balls slapped against her. I slowly started to move back and forth, gently, and holding her close. Rachel was moaning and whispering my name each time I pushed forward and before long I couldn't hold back and came deep inside her. She continued to push back against my cock, milking every drop of cum she could out of me. Eventually I was completely drained and we lay together like that, my cock still buried in her ass and drifted back off to sleep again.

The next time we woke it was beginning to darken outside and I had to shake Rachel to get her up.

"What's wrong Darren?" She asked turning to face me.

"It's early evening and I thought you had to go and find something for me." I said.

"Shit you're right I was supposed to wasn't I." She said and sat upright. "Unless I don't bother today, undo you and we just make love nonstop until morning."

"That sounds so good but I need to finish your tasks." I answered. "Then we have all the time in the world to do whatever we want, and how we want."

Rachel got up off the bed and stripped off her underwear, leaving herself standing there naked.

"Tell you what." She said. "I need a shower and I'm going to trust you to have one with me."

"Are you sure you can trust me." I answered.

"Well do you want one or not?"

"Yes you know I would love one." I answered.

Rachel came over to the bed and undid all my restraints, but took my callipers off me.

"Come on then I'll help you." She said and put her arm around me.

Eventually we made it the bathroom and, after seeing how I had struggled to get this far, she began to run the bath. Once it was ready she helped me in and made sure I sat down before climbing in and joining me. As we sat there we washed each other's bodies, before Rachel turned her back to me and leaned back.

"You know something Darren." She said. "I think after tonight everything is going to be just perfect."

"It will." I said. "I won't let you down."

"I know you won't Darren."

After being in the bath for about an hour Rachel helped me get out and dried, then took me back to the bedroom. Instead of fully chaining me up she attached just one leg to the bed and went and got herself ready. She came back to me before she went out, top show me what she was wearing, kissed my forehead and turned away.

"I won't be long Darren." She said. "No trying anything or wanking."

"I won't, I'll be waiting though so don't be long." I told her.

I heard the front door open then close and just sat, waiting, hoping she wasn't gone too long. If I played everything right I reckoned she would be releasing me from these restraints for the last time, at least that's what I hoped.

Eventually, after what seemed like hours, I heard the front door open and two people enter. I listened carefully and heard two female voices laughing and joking with each other, and then the bedroom door was opened.

"Hi Darren we are home." Rachel said coming in to the room alone.

As soon as she was in and sat down another figure appeared in the doorway. I looked towards the door and saw her for the first time, she was absolutely stunning. She was just short of six feet tall with long brunette hair, perfectly sized tits and legs that seemed to go on forever. She was wearing a salmon pink, strapless cocktail dress and matching high heeled shoes.

"Darren this is Nicola." Rachel told me.

"Hi Nicola." Was all I could say.

"Why don't we all have a little drink before we get started?" Rachel said.

"Sounds good to me." Nicola said.

Her voice was just as sexy as the rest of her.

"Are you going to have one with us Darren?" Rachel asked.

"Yes please Rachel." I said my eyes never leaving Nicola.

Rachel left the bedroom to get some glasses and the drink, leaving me and Nicola alone, before eventually returning. Soon one drink had become two which then became nearly a whole bottle and we were all laughing and joking like old friends, Rachel even released my restraints when Nicola left the room to go to the toilet.

"How are you feeling about tonight Darren?" Rachel asked while we were still alone.

"Nervous but at least she is gorgeous." I said, before quickly adding. "Just not as gorgeous as you."

Nicola rejoined us in the bedroom and Rachel excused herself, saying she was just going to get another bottle. When she came back she had got another bottle but I also noticed that the red lights on the cameras were also on, and knew that it was time.

I felt completely relaxed, probably due to the drink, turned and looked into Nicola's eyes. They were an emerald green and strangely hypnotic. I reached my hand towards her face and lightly brushed her cheek with my fingers. Her hand did the same and we slowly leaned in to each other and our lips touched. The feel of her lips was electrifying and I held her head as my tongue began to explore the inside of her mouth. Nicola reciprocated and soon our tongues were entwining around each other, like two snakes mating, and I ran my hand down her back and held her tightly, before easing her gently onto her back.

Her hands ran down over my taut shoulder muscles and, slowly down my back, finally coming to rest on my naked ass. My cock was hard and pressing against her stomach and as she squeezed my ass I rolled her onto her side and began to lower the zip on the back of her dress, before pulling it down and exposing her pert, bra covered tits.

Her bra was red and black lace with the clasp on the front and, unable to control myself any longer, I flicked the clasp undone and released her breasts. Her nipples immediately hardened, when the air came into contact with them, and I lowered my head and flicked my tongue lightly over each one causing Nicola to gasp softly.

She continued to squeeze and massage my ass as I sucked, licked and bit her nipples, before slipping one of her hands in between us and wrapping her hand around my cock. As she began to move her hand up and down, stroking me slowly, I began to push my hips against her movements. She tightened her grip a little more and soon I was moving rapidly and, literally, fucking her hand.

"Slow down Darren." She whispered in my ear, and I did as she asked.

Nicola pushed me onto my back and continued to stroke my cock as she lowered her head. I stopped moving and pushed my head back into the bed and, as her lips encircled my cock, I let out a low gasp. She sucked me slowly, her head hardly moving, and it took me all my willpower to stop myself cumming.

"Stop Nicola I don't want to cum yet." I said and she lifted her head and looked at me with those hypnotic eyes.

"You better take the rest of my clothes off then." She whispered.

I stood up as she lay flat on her back and lifted her ass slightly. Taking hold of her dress that I had already partially pulled down, I eased it over her stomach and down her legs before dropping it to the floor. Her soft skin looked perfect as she lay there in just panties, which matched the bra, and I looked her up and down, my cock pointing directly at her.

"Now the panties Darren don't be shy." She said.

I knelt down on the floor, took hold of her ankles, and gently pulled her until her legs were dangling over the edge of the bed. Running my hands lightly up her legs I hooked my fingers into the waistband of her panties, and slowly pulled them over her hips. As her panties started to come down her dark, neatly trimmed pubic hair started to come into view. Eagerly I stopped going slowly and quickly ripped the panties off her and, as she parted her legs more, her cock sprang up from between them.

My eyes widened when I saw the size of it. It was at least two inches longer than my seven and a lot thicker as well. Slowly I reached forward and took her cock in my hand and went to wrap my fingers around it. It was too thick for me to be able to encircle it fully, but I still started to masturbate her slowly. As I did a small drop of pre-cum oozed from the end and, as it did, Nicola reached behind my head and pulled me towards her cock.

My lips brushed against the pre-cum and, more by instinct than anything, I quickly licked it all off. Her cum wasn't as salty as Matt's was and it was also slightly thicker and I opened my mouth and began to ease her cock in. This time I did gag as the thick, purple end caught the back of my throat and I pulled my head back slightly, until it was comfortable. My head began moving up and down her shaft, my tongue working around it as I did so and Nicola started to buck on the bed. I went to stop but she held my head in place.

"Don't stop Darren please swallow it all for me." She gasped as she bucked even more.

"Yes Darren swallow it all." Rachel said from close behind me.

Unable to resist Nicola's soft, sensual voice, and Rachel's slightly domineering tone, I continued to suck the cock embedded in my mouth. Nicola bucked wildly twice more and, with both of them encouraging me, I braced myself until the first warm, thick stream exploded from the end of Nicola's cock coating the back of my throat. I swallowed as fast as I could, making sure none spilled from my mouth.

Finally Nicola stopped cumming and I took my head away, licking the end as I did so. She smiled up at me before gripping my wrist, pulling me down on top of her and passionately kissing me.

"I love to kiss the person that swallows my cum." She told when she pulled away. "The taste is so good."

"You sucked her cock better than you sucked Matt's." Rachel said. "I think you are almost ready but you still have to fuck and be fucked yet."

I'd almost forgotten about that, and the thought of Nicola pushing her cock into my ass filled me with more than a little fear. At least she wouldn't be doing it for a while, especially after the amount of cum I had just swallowed, which meant that I would be expected to fuck her first.

"Come on then Nicola." I said. "I need to fuck you and fill your tight ass with cum."

Nicola smiled at me, rolled onto her stomach and lifted her gorgeous ass up ready for my cock. I moved between her legs and slowly pushed my cock's swollen, purple head towards her tight little ass and pushed gently. Unlike Matt's ass the night before Nicola's loosened immediately, let my cock slide in and I began fucking her slowly. I reached my hand under her stomach and began to stroke her cock back to full stiffness as I fucked her and, after a few minutes, I felt the first signs that I was about to cum. My legs began to quiver, my balls tightened and, before I could warn her, I exploded deep inside her ass.

"Oh fuck yes fill me Darren." Nicola screamed and pushed her ass back onto my cock hard.

I continued to thrust deep into her, cumming more than ever, until I was completely drained. Sweat was pouring from my forehead as I collapsed on top her, my cock still buried as far into her as I could get it.

"Fucking hell Darren no-one has fucked me as hard or as intensely as you just did." Nicola said. "I wish I could take you home with me.

"Well maybe you could visit us again." Rachel said and slapped me lightly on the ass. "Your turn Darren on your knees."

I had only just got my breath back but complied with Rachel's order and very quickly Nicola was behind me trying to force her massive cock into my ass.

"He's too tight Rachel have you got any lube?" Nicola asked.

"You stay there I'll be right back." Rachel replied and left the room.

While she was gone Nicola carried on pushing against my ass, stroking my cock while she did, but she still couldn't force it in. It was beginning to really hurt as she pushed and pushed but, thankfully, Rachel came running back into the room with a brand new tube of lube and threw it to Nicola. She pulled away from my ass and squirted the lube all over my tight hole, making sure I was completely covered, and slipping her middle finger in to loosen me a little as well.

Retaking her position behind me she covered her own cock as well and tried to enter me again, this time managing to slide in, with a bit less trouble. I felt my ass stretching, and thought she was going to rip my apart, as she gently eased her cock all the way in my ass. Her gentleness stopped once she was fully in and, holding my ass tightly, she began to ram her cock hard and fast. Her massive cock pounded into me, her balls slapping against my ass, when Rachel dropped the envelope on the bed in front of me.

"Read that Darren and I shall give you a choice." She said.

Lifting my head I managed to open it and read what she written, before my tasks had even begun, and looked at her as Nicola continued to pound her cock into my ass.

12