High School Reunion

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I was shaking at the thought. My cock was throbbing and dripping pre-cum, just from going down on these two beautiful girls, and the feel of that plug deep inside of me, pressing up against my prostate. Could I really handle the real thing, though? Claire and Jackie were both huge, very well endowed girls.

I felt a pull at my ass, as Jackie slowly withdrew the plug and examined my asshole. I felt her fingers tracing lightly over the hole, and heard her moaning softly. Then I felt something hot and wet pressing between my crack, and I gasped, before moaning loudly; it was her tongue. Jackie was furiously licking at my backside now, giving me my very first rim job. It felt surprisingly good!

I never thought about such a thing really but, now I found myself wondering why I hadn't tried it sooner.

"Jackie's gonna get you nice and wet," Claire said, as she watched me suck at her cock.

"Don't you worry...she'll make sure it slides in, good and easy."

I didn't really care about that, right now. I was too focused on how good it actually felt, as Jackie licked and probed my ass with her tongue while reaching around to stroke my cock with one hand. I felt something pressing against my ass but, paid it little attention, until I felt it slip right into me...it was small...just a finger but, the pressure was intense, much like it had been with the plug they'd used earlier. Jackie continued to rotate between licking and fingering my ass, eventually working a second finger into me, and stretching me further.

As she worked both fingers in and out of my ass now, Jackie ran her tongue down the space between my balls and my ass, taking the time to tease it for a few moments, before moving on to my balls. She started sucking on them, one at a time, and by now, she had me moaning like a complete little bitch.

"Fuck," Claire moaned. "Jackie, you're getting him so turned on...I think he's ready for that big fat cock of yours."

"Think so, babe?"

Jackie pulled her fingers from my ass and examined her handy work. After a moment, she groaned softly and I looked back over my shoulder at her.

"Yep, I think he's ready," she announced, with a big sexy grin. Then standing up, Jackie stretched for a moment, before grabbing the lube from the coffee table and pouring some out into the palm of her hand.

She smeared the lube all over my ass crack and worked it into my hole with her fingers, making sure that I was as slick and wet as possible, before applying an extra amount to her cock. Taking her dick in one hand and setting the bottle down, Jackie looked up at Claire and smiled. "Here we go," she said softly.

I looked back at Claire and took a deep breath. She leaned in close, a finger under my chin and made me look her right in the eyes. "Just relax baby," she whispered.

"Take a few deep breaths, and try to relax. As long as you stay calm, it shouldn't be too difficult. And remember, don't clench."

I nodded in understanding, as Claire tried to give me tips on how to make this as painless as possible...I was still nervous as hell, though.

Jackie stood over me, her monster cock pointing straight toward my ass. As she leaned in and pressed the tip against my hole, I tensed up for a split second, before Claire gave me a nudge and reminded me to try and relax. I took a few deep breaths, as she had instructed, and tried not to panic much. Jackie pushed forward and I felt it pressing harder against my hole...harder...harder...and then...POP!

With a loud and audible wet pop, Jackie's cock slipped straight into my asshole, officially deflowering me. I gave a sharp gasp, my eyes nearly shooting out of their sockets, as I dug my fingers into the carpet.

"Fucking hell," Jackie exclaimed. "He's so damn tight!"

Claire directed my eyes back to her and offered me a comforting smile. "How are you doing, down there?"

"I-I think I'm okay," he said, a little winded.

"It hurts but...n-not as bad as I expected."

"Good," Jackie said. "Now, why did you stop sucking her!?"

Jackie gave a powerful thrust, burying her cock balls deep in my ass and causing me to help in a bit of pain. She smacked my ass hard, three times, leaving a big, red handprint on my cheeks. Claire giggled, before pushing my head back down and shoving her cock down my throat again. I gagged, as she held it down, my nose digging into the small patch of red pubic hair. Meanwhile, Jackie was now aggressively pounding my ass, thrusting her long, hard cock, in and out of me as hard as she could manage. Her balls slapped against me, the sound of our bodies slapping together, echoed throughout the apartment.

I was being fucked from both ends...and truthfully, it felt great!

"Take it," Jackie said through her teeth. She smacked my ass again, looking down and watching her own cock slide in and out of me. "Take my fucking cock, you dirty little bitch."

"Damn, babe," Claire giggled. "I haven't seen you this fired up, in a long fucking time...you're having fun, I take it?"

"Oh, you know it," Jackie said, breathing heavily.

"He just feels so good around me! Can we keep him?"

"Hmm, we have been wanting a pet for a while now..."

A pet? I gave a mental laugh, at the thought of them keeping me as a pet. I didn't realize just how serious they were both being, though.

"I have to get a piece of that booty myself before I can decide if he's slave material," Claire said. She moaned as I started sucking her cock more eagerly now, and reaching up with one hand to cup one of her breasts.

"You are an eager little boy, aren't you?"

"He'd make a great slave," Jackie groaned. "Fuck...I'm gonna cum soon...he's so god damn tight, I can't hold back much longer."

"Are you gonna cum inside of him?"

"Oh fuck yeah, I am...I'm going to breed him, like the little bitch that he is. That's what he's meant for...he was born to take cum in that delicious little ass of his."

All the dirty talk between the two of them was really starting to turn me on even more. I was moaning and grunting between Claire and Jackie, stroking my own significantly smaller cock, faster and faster, as I felt myself getting close to my own orgasm. Jackie started fucking me hard and a lot more aggressively, to the point where there was a slight level of pain involved...I could take it though, I kept telling myself.

The three of us were so into it by now, that Claire and Jackie were literally making out over top of me, while they continued to plug both of my holes at the same time. I could feel Jackie's tits digging into my back, as she leaned over me to make out with her partner. I felt her cock swelling up inside of me, and she started breathing harder, and I knew she was close.

Then without warning, Jackie bucked her hips and with a low grunt, her cock erupted and shot off deep inside of me. The warmth of her cum pumping into my hole, filled me with a feeling of pleasure, as she painted my insides white. My own cock jerked and began to spurt, jizz spraying all over my hand and the floor...I had made a little bit of a mess.

Jackie stopped kissing her partner, pulling away and kissing my shoulder, as she struggled to catch her breath for a moment. She continued gently thrusting her hips, her cock still hard as a rock, even after her intense orgasm. She slowly and carefully pulled out, and I was left with an immediate feeling of emptiness.

I could feel the cool air blowing into my gaping asshole, as Jackie leaned in to get a good look at her work.

"Mmm, I really filled you up," she whispered.

I felt her sliding two fingers into me and moving them in and out, causing me to moan loudly. She pulled them out to reveal, they were covered in her own cum, and she licked it up.

Claire giggled, as Jackie kissed one of my ass cheeks and gently bit it, before standing up slowly and letting out a heavy sigh.

"Looks like it's your turn, babe."

"Ohh, I have been waiting for this, for so long," Claire said excitedly.

She pulled her cock from my mouth and stood up, moving around behind me. I stayed in the same position, my body still twitching from my own orgasm, my legs shaking underneath of me, even though I wasn't standing. Claire lined her cock up with my gaping hole but, stopped suddenly.

"Hmm...let's take this to the bedroom, shall we?"

Jackie smirked at her girlfriend. "I think I know what you've got planned...and if I'm right, then I like the way you think."

What did she have planned?

Claire and Jackie both hooked their arms under mine, pulling me to my feet and leading me from the living room, down a short hallway and into their master bedroom.

The room was pretty big, with a Queen sized bed, covered in red silky sheets and blankets. The walls were a tan color, with a black curtain covering the windows. It had a very goth/punk sort of vibe to it, especially with the black candles that were sitting on the vanity and the dresser. Claire shoved me onto the bed and climbed on top of me, her lips moving to mine and her tongue working its way into my mouth. As we made out and she stroked her cock, Jackie started fishing through one of the drawers in the dresser, what she was looking for, I had no idea.

Suddenly, Claire flipped me over onto my stomach and grabbed my arms, pulling them behind my back and holding them together. "H-Hey, what the-"

"Shut up," she said, giving me a hard slap on the ass.

"Hurry up over there," she yelled at Jackie.

"Found them!"

What the fuck was going on? Things had taken a very strange turn, and Claire was now being a little more aggressive with me, then I had seen her act earlier. I heard what sounded like chains clinking, as Jackie walked over to the bed and handed something over to Claire. "Hold still," Claire warned.

The next thing I knew, my hands were in cuffs.

I felt the cold metal against my skin and heard them click loudly as she closed them tightly, around my wrists.

"What the fuck is this about?" I asked, a little angry now.

"Relax," Jackie laughed. "It's just for fun, nothing more."

I hadn't really realized how kinky these two bitches were.

Grabbing me roughly, Claire turned me around on the bed, so that I was facing the left side with my head hanging off the edge. Jackie walked around the room and stepped in front of me, stroking my cheek and standing so close, that her cock was right in my face...I knew what she wanted. I opened my mouth without even being told, and with a grin, Jackie slid her cock right between my lips.

As she did this, Claire lined her own cock up with my ass and slammed straight into my hole. I was still well lubricated from Jackie, and her cum made it even slicker, so she slid in with ease. "Oh wow," Claire groaned.

"You were right...he feels great," she said excitedly.

"I told you so!"

Claire wasted no time, as she started pumping my ass, thrusting in and out and pressing her full body weight down on me. The handcuffs dug painfully into my wrists, and I groaned, as Claire kissed the back of my neck while she fucked me. Jackie was holding my head with both hands, fucking my mouth, her balls slapping hard against my chin with each thrust. Over the next few minutes, I was used as a fucking blow up doll.

They switched positions various times and took turns fucking my ass until it was gaping and full of their seed. I swallowed mouthfuls of cum until I felt so full, I swore I couldn't take anymore. By the end of the night, we were all exhausted.

I found myself sandwiched between Claire and Jackie, all three of us covered in sweat, as we snuggled up together and drifted to sleep. If you would have told me ten years ago, that one day, I would be having sex with my biggest bullies...and that they would be two of the sexiest girls, I'd ever met...I never would have fucking believed you.

I woke the next morning, to find myself alone in their bed.

Confused, I sat up slowly and rubbed my forehead. My body ached, my ass was still quite sore and very loose and I could still taste cum on my breath. Standing up, I found it difficult not to fall right over, with my legs shaking underneath of me. I wandered out of the bedroom and found Claire and Jackie sitting in the kitchen, both of them still naked, drinking coffee and smoking their morning cigarettes.

They both looked up at me and smiled. "Look who's awake," Jackie nodded.

"Morning," I said, still a bit groggy.

"You sleep good, sexy?"

"Yeah, I...w-what happened, last night?"

"Oh come on now," Claire laughed. "We weren't that drunk."

"You turned into a total cock slut, that's what happened."

"I remember that," I said, sitting down at the table. "It's just so faint...I don't even remember falling asleep."

"You were exhausted," Jackie said.

I yawned, stretching a little, as Claire stood up to pour me a cup of coffee and handed it to me. I took a sip and groaned; I was nothing without a good cup of morning coffee.

"So," Claire said, with a start. "How do you feel about it all?"

I looked up at her and Jackie, and they both stared at me, almost looking anxious for my response. I thought back on the night before, trying to clear the fog that surrounded my mind and remember things a little more clearly. From what I did recall, it had been the best sexual experience, that I'd ever had.

Granted, I had only slept with a few people before but...what Claire and Jackie had done to me last night, topped those few other experiences that I'd had. "It was great," I said, finally.

"I mean, I just...never knew I would enjoy something like that."

"I think it was more than enjoyment," Jackie laughed.

"You were moaning like a fucking bitch, the whole time."

I blushed, and both girls laughed, as they started talking about some of the things that they had done to me the night before, and how watching me squirm around as they fucked me, had been a huge turn on for them both. "Do you think you'll be willing to hang out with us some more, in the future?" Jackie asked, after a while.

"You mean, actually hang out...or ride your cocks again?"

"Both," Claire replied, and we all laughed.

"Well yeah, definitely. As I said, I really liked what we did..."

Claire smiled at Jackie. "Looks like we've got a third wheel, babe."

"Three is always better than two," Jackie said.

They both looked back at me, grinning evilly at me.

"You have no idea," Claire said. "The things we've got planned for you, Jimmy boy. We're gonna rock your fucking world."

Oh boy, I thought.

What HAD I gotten myself into?

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  • COMMENTS
24 Comments
smoothed273smoothed2738 days ago

👍👍👍👍👍👍💖💖💖💖💋💋💋💋✌🙏

smoothed273smoothed273about 1 year ago

💖💖💖💖💖💋💋💋💋

baratect2baratect2over 1 year ago

One of my favorite stories on this site

illwindillwindabout 4 years ago

This wasn't great. Wasn't completely terrible either, but there were definitely some problems.

The most glaring issue is that you forgot that you had made the MC a virgin; which is kind of a big deal. It goes from them finding out he's never had sex, to them nearly fucking him in an alleyway. And once they get back to the apartment they aren't exactly gentle. Then at the end of the story he's comparing his night with them to his other sexual experiences...huh? What happened to him being a virgin?

This really felt like two stories. One had a great setup and I was excited to see how it panned out. But from the moment they actually decide to have sex and leave the bar, it was like all that setup was forgotten and it turned into a generic shemale-on-male sex story. The story could have just been him meeting these two in a bar and going home with them. The fact that he was a virgin, that they went to high school together, and that they were his former bullies...none of that seemed to be a factor once the sex started.

The sex itself wasn't bad, but again, it just felt disconnected from the writing that came before it. I like when trans get a little rough with their boys and it would have been a fairly hot scene in another circumstance, but given the setup I would think they would be going out of their way to make sure he was having a good experience. If not out of guilt then because he's a virgin. Instead they just completely use him and give him a smack anytime he dares to question what they're doing. That's not exactly how I saw them making things up to him. Hell, did he even orgasm? Seems like that was forgotten about as well.

This was a great premise and I would love to see it get the ending it deserves, but this isn't it.

AnonymousAnonymousabout 4 years ago

hope we get to see more about Clair, jackie and jimmy. this story was awsome

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