My Pretend Sex Slave 05

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College girlfriend pushes sexual boundaries. Roommate joins.
7.1k words
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Part 5 of the 8 part series

Updated 10/28/2023
Created 09/24/2023
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Jett and I were lying in bed naked, our bodies pressed together. The makeup sex had gone wrong, but we made up for it and more. She loved me. The actual words were spoken.

And then more words were spoken.

She wanted to fuck Lisa.

"What? Did you--" I started.

"No," Jett said. "But I wanted to."

The admission made me wildly uncomfortable. Every moment Lisa was in my life was dangerous. Minutes ago Jett said she loved me. Now we were talking about Lisa.

I took a deep breath.

Jett pulled away, turned and faced me. I could watch her eyes while she spoke. Maybe she wanted to gage my reaction.

Who was I to judge? Maybe Jett wanted to fuck Lisa after their photoshoot, but I was the one who actually did it. The fleeting sense of overwhelming safety and peace was washed away on a tide of guilt.

"Why didn't you?" I asked.

Jett stared at me, hazel eyes questioning.

"That's not..." Jett said. "What I meant was, I'm sorry. You were right."

"It's okay," I said. "I want to understand. I'm not judging."

I didn't know if that was true, but I couldn't let this go. Things were always so weird between the two of them, between us. I was navigating dark water, and I needed light.

"It took me a while to figure it out. I don't really find her attractive, not girls in general. It was the whipping. The crop. That was what got me, what turned me on," she purred.

"So you want to try it?" I asked. Our first step in to bondage had gone wrong. The cuts on her wrists made me uncomfortable. I didn't want any more of that in my life, but I would also do anything for her.

"Yeah, but not me," Jett said. "Her..."

Jett paused, trying to think through what had happened, to find the part that grabbed her.

"I liked when she was tied down, and not just whipping her. We didn't really do it, sort of faked it, but I liked the moment, where she was hurting and writhing in pain and then it changed, became... hot. She liked it, the pain, and I liked it when her pain became something else."

My heart was racing again. I could process her words, but I couldn't understand them. Getting turned on by pain... No, that wasn't what Jett was saying, not that exactly.

She was turned on by that moment of transformation.

"Like your paintings," I said. It was a theme running through most of her work. Fear and pain transformed.

Jett took a second to connect my words to her feelings to her art.

Then her face lit up, her nervous smile turned radiant, finding something she didn't realize was missing, but was critically important.

"Yes!" she said.

Her eyes darted back and forth with mine. She kissed me, exuberant.

"That's not exactly it but yeah. That's it. That's the thing I was looking for, putting that moment on canvas, capturing it, freezing it. Transformation," she said.

Jett looked so happy. Material gifts had always bounced off her. The gifts that landed best had always been my words.

"Jesus," she said. "I need to go."

"Why?" I asked.

"Paint. I need to... this moment," she was out of bed, looking for her clothes. I saw my cum on her thighs. "Fuck I don't have any real clothes."

"Go home and change. Or better yet, stay," I said.

I watched her pace around naked, picking up her shorts first, then finding her hoodie. Jett threw it on then zipped it up almost to her neck.

"It could work," she said. She was still naked from the waist down. I saw glimpses of her recently shaved pussy. "Where are my shoes?"

"Jett?" I asked.

She turned to me. I ran my eyes up her legs, then focused on the area in between.

"Right," she said. She slipped on the shorts. The languid posture from our post sex cuddling was gone. She was back to manic, like I found her at the coffee shop the day before.

"I gotta go," she said. She ran back to the bed and kissed me again, more excited than passionate. Overwhelming energy but not sexual.

"Thank you," she said. She looked down at her wrists for just a moment, at the cuts and bandaids that covered them. "For everything."

"You're welcome," I said. I tried to mean it, but I didn't exactly know what she was thanking me for.

"Okay," she said. "And you'll talk to Lisa?"

"About what?" I asked.

"Using the crop," Jett said. "On her."

--

I missed my first class, but eventually got out of my apartment. I wish I could get out of my head. I was exhausted. A thousand crazy things stacked up on my life back to back to back, all before I even had coffee.

Our almost breakup. Then make up. Bondage gone wrong. Hurting Jett. Her liking it. Intimate sex. She loved me. She wanted Lisa.

Midterms were right around the corner. I couldn't afford to ditch class.

--

"You owe me a story," Lisa said. She flashed that mischievous smile.

We met at a food court near the library in between class. Lisa was out in public, wearing normal clothes. Conservative even. It was weird. We sat outside and ate nachos. Lisa sat next to me at an outdoor table, our legs almost touching.

She knew Jett and I had some sort of sex related injury. I had called her desperate for a first aid kit. She didn't know any details.

Jett wanted to fuck her. Well, not exactly that. Include her. Whip her. Where to begin?

"Jett wanted me to ask you..." I tried to run through the various ways Lisa would laugh or tease or double down. Fuck it. "Jett wants to replicate the photoshoot."

Lisa's eyebrows shot up. "Replicate how?"

"Tie you up," I said. I didn't bother to specify rope or barbed wire. No more barbed wire. "Then whip you, but for real."

"Oh," she said.

No clever retort.

"Is that something you would be in to?" I asked. Lisa had a crop, which meant she had some interest, but maybe she used it on other people, or maybe she just liked the idea of it.

"Then what?" Lisa asked.

"What do you mean?" I asked.

"After you tie me up and whip me. Then what? Do you fuck me? Do I fuck her?"

I hadn't gotten that far. Her simple words set off a chain reaction of images. Lisa bent over and tied down, body exposed to me. Sliding my cock inside of her while she moaned. Then her and Jett, kissing, large tan breasts smashed against pale and petite. Lips and tongues together, a look of desperate want in their eyes.

My cock moved.

"I don't know," I said.

"What do you want?" she asked.

She stared at me, giving me her absolute attention.

I didn't have an answer.

"Can I kiss her?" she asked.

The flash of lips on lips, naked bodies. My throat felt dry.

"Yes," I said.

"Go down on her?" she asked.

I imagined Lisa between Jett's thighs, that mischievous grin. Jett writhing in pleasure. I didn't know if she really wanted it or was just trying to get a reaction.

"Yes," I said.

"Her on me?" Lisa asked.

For some reason I imagined Lisa still tied up and bent over. Pussy and ass open and exposed. Jett lowering her face between Lisa's full cheeks.

I nodded.

"What about you?" Lisa asked.

Her words bounced off me. My head was reeling.

"I don't--"

"When you... when we did... the other night," she started. "Was that about me or was it about Jett?"

She seemed closer all of a sudden. I had a flash of our night together. I had called her slave, before putting my cock in her mouth.

Something else was rattling around in my brain, a connection not made. Lisa had questioned my relationship with Jett before. At the moment it felt like jealousy, but something else was going on. I thought of myself as a smart guy, but bouncing back and forth between these two women left me feeling the opposite.

"I don't know," I said.

"What do you want?" she asked. Her voice was quiet. She was asking if I wanted to fuck her. We both knew the answer, but yet...

"What I want to do," I started, "and what is right, aren't always the same thing."

Lisa pulled back. Looked away. I felt like an asshole, making a bad thing worse. I didn't know how to tell Lisa that I found her fascinating and sexy and scary and exhausting, and that it was wrong to cheat on Jett.

I reached for her small hand, took it in mine. She looked back to me.

"I'm sorry," I said. It was the best I could do.

"Talk to Jett," she said. "Set your limits. Together."

"What about you?" I asked.

"I'll do it," she said.

"What about your limits?" I asked.

Lisa stood up and looked down at me.

"Same as yours," she said. "Whatever Jett wants them to be."

It felt like an insult. Maybe it was just true.

--

Jett wanted to paint. For once I didn't mind. I wanted to stop by, to bask in our exchanged words. She loved me.

But I stayed away. We needed to talk in detail about Lisa and boundaries. Who could fuck what. That conversation could wait. Needed to wait. My head was still spinning.

I didn't really know what to do, so I went to the study group. Mia and her friends. Mid-terms were coming up. When we got through Applied Stats, we could shift over to one of the other classes we had in common.

--

Jett showed up at my place late that night. She smelled like chemicals and paint. I didn't mind.

We made love on sheets I hadn't managed to change yet. We didn't talk about Lisa or bondage. We spent time just kissing, as if we didn't know it would end with my cock inside of her, exploring each other with no particular goal in mind.

It was a wonderful change of pace. I didn't need new or dangerous. I didn't need to find some deeper meaning about transformation and pain. I just needed to be close to her.

--

I put the conversation off for a few days. Both Jett and Lisa hinted around for follow up, both seemingly curious to move forward with Jett's plan.

I went to her at the studio, but Jett met me outside. Something about not showing her work until it was ready.

"Lisa said yes," I said. I didn't need to clarify. The question was on the front of her mind.

"Okay," Jett said. She took a deep breath.

"That's what you wanted?"

"Yeah, it is," Jett said. "There is a lot to think about though."

"Lisa had conditions," I said.

Jett looked surprised. I had the feeling that life not only never told her 'no', it almost always gave her an enthusiastic 'yes.'

This was about to get awkward. But I wasn't forcing this issue. Jett was.

"She wanted to know if she could kiss you, if it was okay with me," I said.

"What did you tell her?"

"Yes," I said. She looked perplexed.

"Is that okay?" I asked.

"Yeah," Jett said. "It's great. I'm just surprised."

This was a strange kind of tight rope. I felt any mis-step would send me plummeting. This was her idea. Why was I under pressure?

"I just want you free to do what feels right in the moment," I said. That wasn't quite true, but it sounded good.

"It'd be kinda hot right?" she asked.

Jett smiled. I smiled back.

"Yeah," I said.

"That it?" Jett asked.

"No," I said, "She asked if you two could do... other things."

"Like what?"

"Anything," I said. "Everything."

"Can we?" she asked.

My heart was racing. My throat dry.

"As long as I'm there," I said.

Jett kept getting closer, it reminded me of Lisa, the other side of this conversation.

"Thank you for... trusting me," she said.

Jett looked around, suddenly hyper aware of her surroundings. It reminded me of the moment in the studio, when we were alone together, when she wanted to suck my cock in public.

"Why don't we continue this conversation at my place?" she asked.

"There was more," I said.

"Tell me," she said. Jett was watching my every move.

"She wanted to know your rules for us, Lisa and I. What are you comfortable with?" I asked. My heart was pounding again. Just asking the question felt dangerous.

Jett's eyes narrowed.

"Like what?" she asked.

I didn't want to have this conversation. This wasn't my idea.

"Come on Jett," I said.

"You want to fuck her?" Jett said. "Your pretend sex slave?"

I had imagined every possible sexual situation with Lisa. It was impossible to separate what I wanted now from what I had imagined during summer, at the height of pretend sex slavery.

"This is your thing," I said. "I want to be supportive. Just tell me what you want."

"I don't know," she said.

I sighed. Her hand reached out to mine.

"I'm sorry. You just gave me permission for anything," she said. "I feel like an ass."

Jett took a deep breath.

"It's not a contest," I said.

"Let's just see how it goes," she said.

"No," I said.

Jett looked surprised.

"Why?"

Things were better with Jett now, great even. She loved me. Lisa and jealousy and bad communication had gotten us in that other mess in the first place. I didn't want to make Jett jealous. No. Not jealous. I didn't want to make her insecure.

"Brett?"

Insecurity was part of it, but I was missing something. This wasn't about Jett. It was about Lisa.

Why?

So many of my conversations with Lisa felt like something was fracturing, like Lisa loved me and all I did was hurt her. I didn't know how or why, and none of it made sense.

I was tired of feeling guilty. I shouldn't have fucked Lisa, but I wasn't the one stripping naked. Pretend sex slavery was her fucking idea.

How could I explain something to Jett that I didn't understand?

"Jett," I said. "Tell me what you want. I love you, but I'm tired of guessing. I'm tired of hurting people because I guessed wrong. I don't understand, but that's okay. I don't need to. I trust you."

Jett leaned in and kissed me. I closed my eyes and rested my forehead against hers.

"I love you," she said.

"Yeah," I said back.

"So anal then?" she said.

What?

I stared at her. Her serious face broke in to a wild smile.

"You should see your face," she said.

"You didn't answer the question."

She took a long pause. I could see her struggle with an idea, but I didn't know what.

"I'm sorry Brett," she said. "I'm not comfortable. I know you love me, and you're amazing, and you said I can do anything. I don't feel the same way. I guess I'm a jealous person."

"It's okay," I said. "I wasn't asking. All I want is you."

"You think it would fit?" she asked.

"What?" I didn't follow.

"Maybe I'm jealous, but I'm not a prude," she said.

Anal sex. I honestly had never considered it. Our sex life was every bit of what I could handle at the moment. There was no need to look for something new.

"I uh," I started, "I've never tried--"

"Me either," she said. "But I would. If you wanted. I trust you too."

She smiled. Nervous, like she was trying to fix something.

I had a flash, Jett lying on her stomach naked. Long legs and tight ass exposed. The moment when it slides in, a groan and a shudder as she struggles to take it. Knowing she did it just for me, an expression of service. A gift.

Just the mini-fantasy made my cock hard. The way she was nervous and hopeful even more so.

She couldn't share Lisa the same way I could, but she could share something else. My body lusted for her, but my brain fought back. Her offer felt wrong.

I wracked my brain until I found something true.

"Jett," I said. "I want to explore every part of you."

"Don't get your hopes up too high," she said. "It may not work."

My cock wasn't huge, but Jett was petite. I had no idea.

"Wouldn't hurt to try right?" I smiled.

"That may not be true," she said. "Or so I've heard."

I took a deep breath. We survived Lisa's gauntlet, communicated difficult things, and now we could laugh about it, or at least banter.

"You'll talk to Lisa?" she asked.

"Yeah," I said.

"Don't expect... I don't want you to fuck her, but maybe in the moment, if I ask you to do something specific, is that okay?"

"Sure," I said.

--

I worked out the details. We were set for Saturday evening. Lisa looked surprised that I was able to hash it out with Jett.

We met at Jett's place. It was large and nice compared to our apartment. I carried the delusion that if it happened at Jett's, away from our home, then Lisa and I would be insulated from consequences. Even in the moment I knew it was wishful thinking.

Lisa brought a bag full of goodies. I assumed it was the contents of her sex drawer.

Then we got to it. Lisa's flirty and adorably irresponsible exhibitionist act was gone. She was different around Jett. Intense. Had it always been like this?

"The most important thing," Lisa started, "is communication. If something makes you uncomfortable. Stop. When engaging in activities like this, we use safe words. Yellow for slow down and check in. Red for stop. Got it?"

We nodded. Jett looked at me. She had an excited grin.

"Brett, take off your clothes," Lisa said.

I looked to Jett, she shrugged. Here goes.

I had confidence that this night would get very sexy very quickly, but it hadn't yet. I was more nervous than anything, my cock not even half hard.

I stripped off my shirt and jeans.

"That's fine," Lisa said. "Jett, you are going to be whipping me, correct?"

"Yes," Jett said.

"Brett, I'm going to show her where to hit and where not to hit. We're going to use you for practice. I need to be able to watch her. Is that okay?"

"Yeah," I said. I didn't find any part of this sexual, but I could take it, using my body to calibrate Jett for the real thing.

Lisa had me put my hands against the wall, showing Jett where to hit or not. Then a few practice swings against my body. They stung, but I could manage.

"Okay," Lisa said.

Jett smiled. I could see the sexual energy crackling in her body, in the slight flushing of her cheeks and chest, the way she stood, her legs spread ever so slightly, like she was making room for me.

"What now?" Jett asked.

"We get in to character," Lisa said. "From here on out, just listen for my safewords. Otherwise..."

Lisa trailed off. I could imagine where this would go, remembering how she had baited me, wanting me but only when it was rough.

"Brett, are you okay?" Lisa asked.

"Yeah," I said. "Yes."

"And you want to do this?" she asked. She was asking the both of us in theory, but I knew she was talking to me.

I nodded. Then Jett did too.

"Some advice?" she asked.

"Sure," Jett said.

"Take my clothes off," she said. "The both of you, together. Then tie me up. Afterwards, do whatever you want. Focus on each other, find what is comfortable. Then you can fuck me or not. You can leave me alone or make me watch. You can make me beg for your touch then ignore me. Or not. Anything you want. And when you're ready, the crop. Okay?"

We nodded.

"So do it then," Lisa said.

Jett and I looked at each other. She was a perpetual smile. Then we turned our attention to Lisa.

Jett started working on those buttons. Delicate fingers removing and opening bit by bit. As much as I didn't want Lisa in my love life, it was hot.

While Jett worked on her shirt, I rifled through Lisa's sex bag, finding the rope.

Lisa was completely stoic while Jett unbuttoned her shirt. The rope was already pre-knotted for exactly this purpose. I had time to watch my girlfriend work on Lisa.

When the final button was released, Jett pulled open Lisa's shirt, exposing her soft stomach and large breasts. Jett opened it all the way, enough to expose dark nipples. Lisa didn't protest.

I'd seen those breasts dozens of times or more, but Jett hadn't. She turned to me, watching me watch. Then she leaned down, grabbing Lisa's breast and and running her tongue across a dark nipple. I watched it get hard in real time.

Oh fuck, I thought. Watching Jett take baby steps toward sex with Lisa was incredible, maybe this had been my fantasy all along, just never knowing it until I watched it unfold.

Jett cut her eyes down to my hard cock.

"You liked?" she asked.

"Yes," I croaked.

"Good," she smiled.

Lisa didn't smile. She looked past us, to the wall.

Jett forgot about Lisa and rushed me, her lithe body grinding in to my hard cock. I was down to my underwear, Jett still fully clothed.

12