Jay's Sex Club Adventures Ch. 20

"A relationship. I mean like an actual relationship. Not just the whole friends with benefits thing. I want to be able to introduce you to people as my girlfriend, not just my friend,"

"That's what I want too," she nodded her head, "But you hurt my feelings pretty bad Jay. So, if you want me back then there are going to be some conditions."

"Conditions?"

I could see a hint of seductiveness in her eyes, and I had a feeling that I was starting to understand what she meant.

"Why do I get the feeling you've been talking to Kendra?"

"Oh I have," she laughed. "And she's given me some good advice. Let's go upstairs and we'll talk about it some more."

We went into the house, and up the stairs to my bedroom. She stepped inside first, and I came in behind her shutting the door behind us, and turning to look over at her. Holly was standing at the foot of the bed with that big sexy grin on her face and I couldn't help but laugh.

"Okay, what is this about now?"

"Get undressed," she said simply.

Slowly, I started to remove my clothes while she made her way into the bathroom to freshen up I assumed. Once my clothes were gone, I laid down in the bed and waited patiently for her to return. She came back out of the bathroom a few minutes later wearing only a pair of black satin panties that showed off the bulge of her erection quite well.

"This will be our first night having sex as an actual couple Jay," she said smiling at me. I realized she was right, and that understanding actually made me really happy.

"But here's the catch, if you really want me back, then you're going to be sucking some mad cock tonight to prove yourself. And that pretty little asshole of yours? It's going to be gaping by the time I am done with you."

I didn't know if she was trying to punish me or not, but if she was it wasn't working because the idea of what she was telling me was about to happen was just making me really horny. She noticed my cock growing hard and gave it a playful slap.

"And it also means our little friend here," she said motioning towards my cock. "Is not going to be seeing much action."

"That's okay with me," I said.

"Really? Cause I'm not done yet."

"Meaning?"

"Meaning... it might be a while before you get a chance to slip that friend of yours into my tight little asshole again. Consider yourself sort of on probation... I love you Jay, but for the next sixty days, you're the one whose going to be taking it in the ass until I am satisfied."

I knew she was serious, and it was a little disappointing that I wouldn't be getting to fuck her ass for two months straight. However, the confidence and sternness in her voice was a huge turn on for me, and I figured this was okay. I was happy to just have her back, and I knew it was at least partly being done out of fun. So, to make up for my stupidity and being such a jerk I was more then willing to be Holly's little cock sucker for the next couple months.

"Should I start calling you Mistress," I asked, jokingly.

She tilted her head, a big grin on her face as if she were thinking it over before she looked back down at me and nodded her head.

"Mistress Holly... I think I like the sound of that."

"Mistress Holly it is," I said, "How may I serve you Mistress?"

"Well," she said, reaching down with both hands and hooking her thumbs over the sides of her panties. She pulled them slowly down her smooth legs slipping out of them and revealing her cock which was by now hard as a rock and standing at full attention, "You can start by getting on your knees in front of me... and sucking my cock until I tell you to stop."

"Yes Mistress," I said.

Then getting on my knees, I crawled across the mattress to the edge where she stood in front of me. I leaned in and licked the tip of her cock, breathing in her musky scent. Apparently, she wasn't to much in the mood for teasing, because she ran her hand through my hair and forced my mouth down over her cock until I gagged. I took her all the way into my mouth and started sucking, her hand guiding me as it held onto my head and I bobbed up and down sucking, licking and stroking. Holly moaned, leaning her head back, and then looked down at me, her dyed red strands of hair falling over her face.

"That's it Jay," she whispered, "Suck my cock like the little bitch that you are."

I started sucking faster, gagging and making the familiar sucking sounds as my head moved up and down over her erection.

"Suck on my balls," she ordered.

I released her cock from my mouth, and moved from her shaft down to her heavy balls, licking them each one at a time before sucking on them gently. As I licked and sucked on her balls, Holly took hold of her cock and started stroking, her hand moving up and down the length of her shaft making her balls jiggle as I licked at them.

She stopped stroking suddenly, and roughly shoved her cock back into my mouth and proceeded to throat fuck the hell out of me. She was really putting my gag reflex on blast, as she shoved her cock in and out of my mouth, moaning wildly the whole time. Then she pulled back again, and looked down at me with fire in her eyes.

"Lay down," she demanded.

Shoving me onto my back. She climbed onto the bed and stood over top of me, lowering herself down so that her balls were right over my mouth. I started to suck on them again, as she jerked her cock like she had a few minutes earlier.

I was being tea bagged, but I loved it and I could see that she did too. Then back into my mouth she crammed her dick once again, really showing me no mercy this time around. She thrust as deep down my throat as she could go, choking and gagging me more. My eyes started to tear up, not because I wasn't enjoying myself, but because that was a natural reaction when something is rammed down your throat like that. I could feel her cock starting to swell up and I knew what was about to happen, but she stopped before it could and backed off laying down next to me for a moment.

I gasped for air as she pulled out of my mouth, and both of us lay there breathing heavily. Once she calmed down some, she got back on her knees and looked down at me.

"Turn over," she said, "Show me your ass."

"Yes Mistress," I replied, turning over onto my hands and knees and pointing my ass out towards her.

I felt the hard crack of her hand against my flesh as she slapped my ass and I jumped in surprise, the loud slapping sound echoed through the room.

"Jay," she whispered, "Did I ever tell you how much I fucking love your sweet ass?"

"Yeah, a few times," I laughed.

She slapped me again, harder this time.

"Yeah?"

"Y-Yes Mistress," I corrected myself, realizing why she had slapped me again so hard, "You have told me a few times before."

"Mm," she groaned.

I felt her hands spreading my cheeks and then I felt her hot breath on my ass. She kissed my ass cheeks, and then started licking up and down my crack. The hot breath on my hole made me shiver and I groaned as I felt one of her fingers slipping into me. She pushed it in knuckle deep, and rubbed up against my prostate, making my cock swell to full size. She pulled back and then pushed back in, and proceeded to start finger fucking my ass with her index finger. Soon, she had two inserted deep inside of me, stretching my hole. She pulled back, removing both fingers from my asshole and spanked me again.

"You've been such a bad boy," she said softly.

And then spanked me again. And again. And a few more times. I was a bit of a sting, but surprisingly still very arousing. My ass must have been bright red bruised at this point, but I did not mind much... and Holly seemed to like that I didn't mind, because she proceeded to spank me a few more times just for good measure.

"I'm going to make you regret what you said to me on the phone this morning, Jay," she said in that stern voice, "By the time I am done with you, you'll never want anyone else again."

I felt the bed shift as she reached over and grabbed a bottle of lube off of the nightstand, popping open the cap and pouring some all over my asshole. She rubbed it in nice and good, slipping two fingers back inside of me and continuing to finger fuck me. I moaned as she stretched my hole more, and then she pulled back and inserted a third finger.

That wasn't to difficult for me to handle, but after two minutes when she started trying to work a fourth finger into my asshole, I began to wonder just what she was trying to do. At this point, I was probably good and ready for her to pound my ass with her cock, but she was trying to insert a forth finger?

I felt my ass stretch wider as the additional finger slipped in, all the way to the knuckle with the other three. She held it like that for a minute, and grabbed the lube, applying more to my ass before she started moving her four fingers in and out of my hole.

"How does that feel?"

"Fucking... weird," I groaned, "But not horrible."

"Good, then let's see if we can fit my whole hand."

Now I understood what she was trying to do, and my eyes went wide for a few moments, before I remembered how many times I had been fucked by different shemales, Holly included, to the point where my hole was gaping wide open. This probably wouldn't be to difficult or painful, considering the things I had already done in the past. I was confident in my assholes abilities.

She slowly withdrew her four fingers and slipped them back in a little deeper, stretching me further and soon enough I felt a strong pressure, a feeling of fullness. I heard Holly laugh a little and she placed a hand on my back. I felt my body starting to shake...it was a strange sensation.

"Holy shit Jay," she laughed, "You're such a dirty little whore."

"H-Huh?"

"How would you feel, if I told you... my entire hand is in your ass right now? Hmm?"

"I-It is? Fuck... it feels good."

"Of course it does, you bad boy. Are you a bad boy Jay?"

"Yes Mistress," I grunted.

"You are a bad boy. You're a little slut Jay, but you're my slut and I love you."

I laughed a little at that. "Tell me you love me Jay," she ordered.

"I love you," I answered.

"You said it wrong," she laughed, pulling her hand out a little and pushing it back in all the way causing me to jump.

"I love you... Mistress Holly," I corrected myself.

"You fucking better," she said softly.

I felt her hand slipping out of my hole slowly, finger by finger and once it was out my body relaxed and I sunk into the mattress, breathing heavily.

"Don't get too awfully comfortable yet," she said, "We're not finished my bad boy."

I heard the cap from the bottle of lube popping open again, and she squirted more onto my hole which was now pretty stretched out somehow, I had a feeling it wasn't quite as stretched as she wanted it to be yet though. I heard her squirting more of the lube, but I didn't feel it on my ass this time. I looked back over my shoulder and saw that she was applying it to her cock, which at this point was so hard it looked like it was about to burst.

Apparently, fisting the hell out of me had really gotten her fired up quite a bit. She stroked her cock, making sure to get it nice and lubed up before moving close behind me. I pointed my ass out towards her again, and felt the head of her cock probing at my hole as her hands moved up and down my back.

"Now, it's time to really make you pay."

With those words, I felt her push her cock into my hole. She didn't just thrust into me though she slammed straight into my hole, her entire length in one straight shot. I jolted, grunting and burying my face in the pillow as she buried herself balls deep inside of me and held her position for a few moments. Then, she slowly pulled out and slammed straight back into me again, earning the same reaction out of me she had gotten when she first entered me. Soon, Holly was pounding my ass, the hardest she had ever pounded it before.

Thrusting in and out, our bodies slapping together with her hard strokes, our bed was shaking underneath of us, as she took her frustrations out on my hole.

She pulled out and flipped me over onto my back, lifting my legs up as high as they could go and thrusting right back into me. It was as if she had never stopped, because as soon as she was back inside of me she was fucking me just as hard as she had been moments before when I was on my hands and knees.

Her heavy breathing got louder, and so did mine, as we both started moaning together. This was supposed to be her way of "punishing" me, but I was so turned on and it felt so fucking good... I couldn't help it, and my mouth opened wide and I cried out, begging for more. "Harder," I pleaded.

"What," she asked, panting heavily. "What did you say slave?"

"H-Harder please... Mistress," I begged.

"You want it harder?"

"Yes please," I moaned.

She thrust as deep as she could, in and out of my ass, hitting exactly the right spot with every thrust that she delivered. Holly started gently biting and sucking on my neck, as she continued to pummel my ass. She knew my neck was one of my most sensitive spots, and she was using it to her advantage.

She pulled out suddenly, and I was left with the feeling of emptiness. She pushed me out of the way and laid down on her back, her cock standing straight up and smiled at me with that sexy smile.

"What are you waiting for... get on," she said.

Still a bit out of breath, I mounted her, reaching behind me and grabbing her cock.

I lowered myself down onto her, moaning as I slid down over her dick until she was all the way inside of me again. At that point, I started moving up and down, bouncing on her cock and she grabbed my hips and started thrusting upwards. The bed was really shaking now, and if this were a rowhome with my neighbors connected to us I was sure they would have heard every creak and moan that we were making.

I rode her cock, bouncing up and down on it, my own dick flopping around slapping against my stomach as I did. I leaned back, supporting myself on one hand and took hold of my dick and started to stroke. Holly slapped my hand away from it and I looked down at her with disappointment.

"I never said you could touch yourself," she said.

"Sorry Mistress," I groaned in frustration as I started riding her faster and harder.

She reached up and started to rub my nipples, gently pinching them and then pulled me in close so that she could lick and suck on them for a few seconds. I moaned louder, my body started to shake as I felt the sensation of an orgasm starting to build. She must have felt it coming, because she grabbed my hips and started thrusting harder. She flipped me back over onto my back, into missionary again, my legs around her waist and continued fucking me as my orgasm started to rise.

I felt her dick starting to swell and her breathing getting heavier, and I knew she too was getting close to her own orgasm.

"Jay... I'm gonna... c-cum," she moaned.

She kissed me forcefully on the lips. Her tongue slipped into my mouth, and mine into hers and we moaned together as she drove herself as deep into me as she could get and held herself there. I felt her cock swelling up more and more until finally her body started to shake and her cock began to pulsate.

I felt the warmth of her cum pumping deep into my hole, we broke our lips apart and she buried her face in my chest practically screaming in pleasure as she emptied her balls inside of me. When she finished, she started slowly thrusting in and out of me again, still breathing heavy. As she continued to slowly fuck my ass, she took hold of my cock and started jerking it for me.

Our lips met again, and we started making out. I felt my body shaking, and tense up and I groaned against her lips, gyrating my hips, my cock sliding back and forth through her clenched hand which was wet with lube and cum.

I howled in pleasure as it hit me full force, and I could feel my asshole clamping down around her cock, squeezing her tightly. With a shutter, I cried out and my cock erupted in her hand, cum spewing everywhere with quite a bit of force behind it.

One shot landed on my chest, and the second on my own face. A few shots landed on her breasts and she laughed a little as I continued to unleash the torrent of jizz that had built up inside of my balls, until I had completely drained my cock. Once it was finished, I sunk into the mattress, exhausted and Holly released her grip on my cock and licked the rest of the cum from her hand.

"You got some on my breasts," she said in her commanding voice. "Clean it up slave."

She leaned in close, her breasts right in front of me, and I started to lick my own cum off of them for her. She moaned, as I licked her nipples and started to suck on them for a moment before she backed away and then laid down at my side. Her head rested on my chest and her hand gently caressing my arm, she kissed my cheek.

"So... am I forgiven," I asked, in a tired voice.

"Yes. But don't ever hurt me again... got it?"

"I'd never do that again," I replied, kissing her on the lips and she smiled.

"I know."

I laughed a little and looked up at the ceiling, thinking about what we had just done, and that it had probably been the best sex I'd ever had in a while now. That, and what we had done the night before after our threesome with Jen. I realized that while I had been with Christina, the sex wasn't all that bad but it had always been missing something. A certain feeling that I always got when I was with Holly, it was a feeling that Christina just never gave me.

That being said, I knew I had definitely made the right choice by calling Holly over here and choosing her.

"So, do I have to call you Mistress all the time for the next two months now," I asked jokingly.

Holly laughed, and shook her head.

"Just when we're having sex," she said, "When we're not having sex, I'm just regular old Holly, Oh, and since your apology was so 'sincere' we'll forget about the top restrictions, after two months I'd miss you're little friend way too much."

"Got it," I said, smiling with the feeling she was happy again.

"Hey, we're still in bed," she said, nudging me softly with a smile.

"Right... I understand... Mistress," I said laughing and she laughed as well. We laid there for a few minutes in silence, and just before I drifted off to sleep I heard her whisper in my ear, "I love you."

The next morning, I awoke to a very sharp pain in my backside. I groaned, shifting uncomfortably and turned over onto my side facing the window. Holly was not in bed with me and I wasn't sure where she had gone. I heard movement in the room though, the sound of the drawers opening and closing and bags rustling. I forced myself into a sitting position, trying to shut out the dull ache in my ass and found myself looking across the room at Christina who was shuffling through her belongings. She noticed that I was awake, and looked over at me.

"Sorry," she said, "I didn't mean to wake you."

"It's fine."

"I figured you uh... made your decision. So, I just came by to grab my stuff and then I'll be out of here."

I nodded my head, and leaned over the side of the bed grabbing my boxers off the floor and slipping into them, then got out of bed. I groaned, walking towards the bathroom with a specific walk that told Christina I'd really gotten it hard last night.

"Fun night," she asked, with a smile.

"Yeah," I laughed, "Not so fun the next morning though."

I walked into the bathroom, relieved my bladder and when I came out Christina was on her way downstairs. I slipped into some pants and a t-shirt and walked down as well, only to find her, sitting on the couch in the living room with her bags at her side.

"So this is goodbye then, right Jay?"

I leaned against the railing for the staircase and nodded my head, running a hand through my hair.