High School Reunion

"Oh my God," Claire said as if she were stunned.

"You still haven't been laid?"

"No fucking way," Jackie scoffed. "Dude, you matured so well, you're a total stud now! How is it possible that you've been with girls since high school but, you haven't had some pussy?"

I shrugged, not sure the answer myself.

"I don't really know...every time I've tried, it just didn't work out, for some reason. Chalked it up to nerves or some shit but, I would just get too anxious and shit would fall apart."

"Or maybe pussies just not your thing?"

I looked up at Claire, who had a big lopsided grin and I scoffed, shaking my head at the suggestion. I knew what she was trying to say, and I laughed, chugging down the rest of my beer.

"I'm not gay," I said, as I set the empty glass down.

"How would you know?"

"What?"

"Have you ever been with a guy, before?"

"No," I said, quickly. "Because I'm not gay!"

"But, how do you know, if you've never tried it before?"

Jackie was laughing her ass off now, at how far Claire seemed to be pushing this little joke. The look on my face didn't do much to help her quit laughing, as she waved the bartender over for another beer. "Claire's got a point," Jackie said.

"You never know, until ya try."

"Right," I laughed, shaking my head and hoping they'd change the subject...and they did, thankfully.

We spent the next hour or so, just talking some more about our personal lives and how things had been going for us all, now that we were older and living with successful careers and shit. The more we talked, the more we drank and of course, the more we drank, the better we felt and the easier it was to talk.

At one point, the conversation drifted back to those days not too long ago, when I was the target of Claire and Jackie's teenage frustrations. "You know one of the REAL reasons we used to fuck with you so much," Jackie asked, her speech slurred a bit.

"What's that?" I slurred.

"You know how our parents always used to say, if someone picks on you, it's really cause they like ya?"

I thought back on it but, I couldn't remember a time where either one of my parents had ever told me anything like that...still, I nodded and smiled, waiting for Jackie to continue.

"I had the BIGGEST fucking crush on you," she blurted out, drunkenly. I just stared at her for a long time, thinking that I must have misheard or

misunderstood her somehow. The look on her face was completely serious but, it made no sense to me.

"It's true," Claire confirmed, with a nod of her head.

"Jackie had it in for you, real fuckin bad!"

"You're fucking joking," I scoffed. "Seriously?"

Jackie just smiled and nodded. "As serious as a heart attack."

"And who could blame her," Claire asked.

"You had, the CUTEST little butt!"

I blushed furiously, looking at Claire, in shock at what she had just said. "You too?"

Now it was her turn to blush, though not as hard as I was. Claire simply smiled and nodded, and I couldn't believe what I was hearing. "Wow...I-I never would have guessed."

"Obviously we couldn't say anything about it," Jackie shrugged.

"So, we just bullied the hell out of you, since we couldn't have you."

"It made shower time fun though," Claire giggled.

I shivered, remembering the horrors that I had faced in the gym locker room and the showers, on an almost regular basis back then. Claire and Jackie would always fuck with me in the showers, coming up behind me and cracking my ass with a wet towel, or smacking my ass with their bare hands. Looking back on all of that, I should have been able to put two and two together but, it never dawned on me that they might have been into me like that...they were the manliest of men at the school.

"I guess that explains a lot," I said, looking back up at them.

"You have no idea," Claire said slowly. "How much we wanted you back then. The things we wanted to do to you, we would have jumped on you like dogs, if we ever had the opportunity."

"The fantasies we use to talk about that involved you," Jackie chimed in. "Mm, you have no idea what we wanted to do to you."

I couldn't help it; they had me a little curious. So it felt like a pretty natural thing to do, to ask my next question.

"W-What did you want to do to me?"

Claire and Jackie exchanged glances, smirking at each other. Jackie took a long swig of her beer, while Claire leaned forward against the bar table so that only I could hear her talking.

"Why don't you come back to our place tonight," she said with a start. "We'd be happy to show you."

I gulped; were they seriously suggesting that they wanted to sleep with me? Before I could say anything, both girls started laughing hysterically, and I suddenly felt really confused.

"We're just fucking with you," Jackie said, laughing still.

"I thought you seriously wanted me to go with you," I laughed.

"You're straight," Claire shrugged. "We respect that."

I nodded, looking down at the table for a second...I was straight...I would be lying though if I said that I wasn't a little bit curious. Maybe that was just the alcohol making me feel that way, I wasn't totally sure. Thinking back on it though, I could recall stealing a few glances in their direction in the showers too.

"I guess, I wasn't completely innocent back then," I admitted. Both girls looked up at me together, curious as to what I was getting at here.

"There were a few times where, I...might have been looking at you two in the showers, for a little longer than I should have."

"Ohhh, naughty boy!" Jackie said, pointing her finger at me.

"That is honestly a big surprise! Did you like what you saw?"

I felt myself blushing, as I thought back on it for a moment. I remembered thinking how they both had much bigger cocks than I did, and wondering briefly, what it would be like to try and suck something that big. I had probably pushed it aside quite fast, chalking it up to just be the curious mind of a teenager. The truth was though, I had always been a little curious, even throughout my twenties...I just kept it buried deep down.

"Look at that face," Claire pointed.

"You're blushing like crazy...you DID like what you saw!"

"I didn't say that," I laughed.

"There's no need to say it, we can tell."

"It's a shame we didn't know you were checking us out," Jackie said, as she finished her beer.

"It would have made it a lot easier for us to make an actual move on you if we had known."

We were all quiet for a second, after that. It was a bit awkward, especially since I was still flashing back on all those times I'd seen them in the showers and checked them out, without either of them even realizing. Just remembering the sight of their big, fat cocks, seemed to make my own dick stir in my pants. The distant memory suddenly took a new form, and now I was picturing Claire and Jackie as they were NOW, two beautiful women, that happened to have something extra. I could see them both naked, giggling in front of me, as they stroked their enormous cocks for me, and motioned for me to join them.

I couldn't believe myself; what the hell, was I thinking?

"You alright there?" Claire asked as I seemed to have spaced out.

"Huh? Uh...y-yeah, sorry, I'm fine."

"Whatcha thinking about?"

I'm sure they would both have LOVED to know, that I had basically been fantasizing about them...I couldn't tell them that though, right? By the look on their faces, they already had a pretty good idea of what I had been thinking about, anyway.

"Tell ya what," Claire said suddenly.

"Maybe we SHOULD take you back to our house...get you out of those clothes...bend you over, lube you up nice and good and make a little cock slut out of you."

I looked at Claire with surprise, and she giggled. I could tell she was being completely serious this time around, and even Jackie looked a little surprised by her partner's suggestion...not that she would have refused, and as she thought about it, Jackie seemed more and more excited by the idea herself. She looked over at Claire and giggled. "Home is too far," she said.

"Maybe the alleyway behind this bar?"

"Oh, now that's a good idea," Claire exclaimed.

"Whoa, whoa," I laughed, putting my hands up now. "Aren't we getting just a little ahead of ourselves, here? I never actually said that I wanted to...well...mess around or anything like that."

"Fair point," Claire nodded.

"Then, let me outright ask you; do you wanna have sex with us?"

I blushed, as both girls stared at me, waiting for an answer and silently hoping it would be the one they wanted to hear. I'm not sure what came over me but, I actually said yes. I took a deep breath, exhaled, swallowed the remainder of my beer and smiled. "Let's do it."

"Fucking sweet," Jackie exclaimed.

Both girls stood up quickly, Claire pulling me up from my chair and they hooked their arms under mine and started towards the exit of the bar, pulling me along with them both. As we walked, I found myself wondering, what had I just gotten myself into? Was it too late, to back out now? Probably was, since Claire and Jackie were both absolutely determined to get into my pants, and I had just said yes, so I didn't think they would let me back out.

Once we were outside, they led me around behind the bar, into the dark and rather shady looking alleyway behind the building. We went as deep in as we could, stopping just behind an old dumpster, where Claire and Jackie both leaned up against a wall and smiled at me. It was Jackie who unzipped her flies first, pulling out that familiar ten-inch thick cock, and motioning for me to get down on my knees.

I gulped, my heart pounding in my chest now, as my stomach twisted into knots with anxiety.

"Well," Jackie said softly. "Get to sucking."

"H-Hold on a minute," I said, scuffing my feet on the concrete and laughing nervously.

"I-I mean, are we really going to do this...right here...in this place?"

"No one can see us," Claire shrugged.

"Nobodies even anywhere around us!"

"Still, I mean, what if someone walks by or something?"

Claire and Jackie exchanged glances and sighed, before looking back at me, seemingly both a bit annoyed now. "Fine," Jackie said, as she rolled her eyes.

"Let's go back to our place, then."

I breathed a sigh of relief.

I wanted to do this, I really did. Something about doing right out in the middle of the public though just did not sit well with me. Even if it seemed like there was nobody, anywhere in sight, I just didn't want to take the risk of getting caught. Explaining what I had been doing in the alleyway, with two transsexuals, to a cop would be bad enough; I wasn't about to go to jail for it, as well.

Jackie zipped her pants back up, putting away that monster of a cock of hers, and the girls led me back out front. They trusted me enough to follow them in my own car, and not turn around and drive back home, ditching them both without any warning. It would honestly have been so easy to do something like that...I didn't do that, though. I stayed tailing them closely and followed them all the way back to their apartment building.

When we arrived, we quickly made our way inside and I found that Claire and Jackie had a really nice apartment for themselves...it was a bit small but, cozy, nonetheless.

"Can I get you something to drink?" Claire asked.

"Water would be fine," I said.

My throat was dry; ridiculously dry. I sat down on the couch and Jackie flopped down next to me, smiling seductively at me, as we waited for Claire to come out of the kitchen. Jackie just couldn't wait to get things started, from the looks of it.

"You know," she said, as she reached over and started rubbing my crotch. "I'm impressed. I didn't think you'd have the balls to actually come back here with us, and do what we're about to do."

"Really?"

"Really! I thought for sure, you'd pussy out on us."

I smiled, nervously and shifted my position. "Well...I'm here."

"So you are," Jackie whispered, as she continued rubbing my cock through my pants.

By now, I was hard as a rock, and I could only imagine how hard Jackie probably was too.

She leaned in suddenly, kissing me right on the mouth. Our lips pressed together and I jumped with a bit of surprise but, offered no resistance, instead opting to kiss her back. As her tongue slipped past my lips and into my mouth, I groaned softly, and Jackie pushed me onto my back on the couch, climbing on top of me.

"Hey!"

We both jumped, startled, as Jackie and I looked towards the kitchen area to find Claire standing with a bottle of water in one hand, and her other hand on her hip. "Couldn't wait for me, huh?"

"Sorry about that," Jackie giggled. "I've been waiting too long!"

"You're such an impatient little slut," Claire teased.

Claire entered the living room and set the water bottle down on the coffee table, before sitting down on a recliner, across from me and Jackie. She just sat there and watched, as Jackie stood up suddenly, and proceeded to slowly remove her pants and panties. Out flopped that enormous cock of hers again, and god damn, was it fucking hard. Jackie was fully erect, and I could already see a bit of pre-cum dripping from the tip of her dick.

"So, are you ready for your first mouthful of cock?" Jackie asked as she looked down at me, with both hands on her hips.

"I-I um..."

"It's okay, sweetie," Claire smiled.

"There's no need to be so nervous. You're gonna love it."

Jackie stepped forward some, as I sat on the edge of the couch cushion, and reached out to gently stroke my cheek. She moved her hand up and ran it through my curly hair, before pushing my head down until my lips pressed against the spongy mushroom head of her cock. I could taste the pre-cum, almost immediately, as she shoved her cock between my lips and started fucking my mouth...no hesitation...no mercy...just straight to the point.

She tasted surprisingly sweet, I couldn't help but notice.

My tongue danced around the head of her shaft, licking up the pre-cum and savoring the taste, admiring the texture of her cock and just the way it felt in my mouth. After allowing me to explore a little, Jackie took control of the situation and shoved my head all the way down, until she reached the back of my mouth...and my gag reflex instantly kicked in.

"Ohhh, that's it, baby," Jackie moaned.

"You are a good little cock sucker, aren't you?"

"Fuck, that's hot," Claire moaned from the other side of the room.

I wanted to look over and see what she was doing but, Jackie held my head in place with both hands now, preventing me from doing anything other than sucking her cock.

"Take his pants off," Claire suggested.

Jackie was happy to oblige.

She stopped fucking my mouth briefly, long enough to pull me up off of the couch and help me out of my clothes. Claire had only mentioned the pants but, Jackie wanted me completely naked for her. My clothes formed a pile on the floor, and once I was totally nude, Jackie sat down on the couch and pointed to the spot on the floor right in front of her; I knew what that meant.

Obediently, I knelt down in front of her and resumed sucking her throbbing cock. I gagged, choked and sucked her cock, occasionally switching off to suck and lick at her balls. All the while, my ass was pointing straight in Claire's direction, giving her quite a view. I heard Claire standing up behind me and she told me and Jackie both, that she would be right back. Jackie didn't even answer, she was too focused on fucking my throat.

When Claire returned a few short minutes later, Jackie looked up and smiled.

"Now there's yet another sexy sight, that I've been dying to see all night."

She allowed me to stop sucking long enough, to look up and see that Claire was now standing in the middle of the living room, just as naked as me and Jackie both were...she was damn gorgeous, too. Her full, luscious breasts were the center of my attention until I happened to look down and notice that huge boner, sticking straight out from between her legs. She was about the same size as Jackie, though a little thicker probably.

"I brought a few things," Claire said, snapping me back to reality.

I looked to the object in her right hand, and couldn't quite tell what it was at first. She stepped closer though, and as she did, I realized just what it was that she was holding.

It was a fucking butt-plug.

"Just to get you warmed up," Claire smirked.

She held the plug up for me and Jackie to both see, then held out a bottle of lube in her other hand. Jackie smiled, forcing my head back down and forcing me to resume sucking her cock. As I bobbed my head up and down, I thought about the things to come. I was only just getting used to sucking dick but, they were already planning to do things involving my ass...was I ready?

Ready or not, Claire wasn't waiting.

I jumped in surprise and gave a low grunt, as I felt something being roughly stuffed into my tight little asshole...it was the butt-plug. Well lubricated, Claire had knelt down behind me and jammed it right into me, without any warning or any real caution. Admittedly, it didn't hurt all that bad...it just felt a little uncomfortable, at least for the first few initial seconds.

I quickly adjusted though, as Claire started moving the plug in and out of my ass, gently fucking me with it, while I tried to focus on Jackie's dick.

"Listen to him moan," Jackie giggled.

"He's so into it," Claire noted. "Who would have guessed, that he was such a little slut, right?"

"And he's OUR little slut!"

Jackie gave my face a light slap, as she said that.

"Right, slut?"

"Y-Yes," I said, gasping for air as she pushed my head back.

"Yes, what?"

"Yes, I'm...your little slut."

"Good boy," Jackie smiled. Then back down my head went, as Claire continued gently fucking me with the plug for a few moments before I heard her heave a heavy sigh.

"I think it's my turn," Claire said, a little irritated.

"What? Oh, come on...and you said I'm impatient?"

"Jackie, seriously! You've had him to yourself, for long enough...move over and let me have a turn, already!"

"Ugh, fine!"

Reluctantly, Jackie pushed my mouth away from her cock and stood up, moving out from her spot on the couch and letting Claire take over. As Claire sat down in front of me, she smiled down at me, stroking her ten and a half inch cock and licking her lips. "Go ahead, baby...give it a taste."

I nodded, before sticking my tongue out and licking the head, just for starters. Claire moaned softly as I did this, and I decided to focus on just teasing her a little, just to get her warmed up some. My tongue swirled around the head of her shaft, edging her on and on until Claire was panting and looking like a hot mess. I almost couldn't believe just how into this, I was getting.

I looked up and saw the lust in her eyes, and that's when I knew I was ready, to get things really going. I wrapped my lips around her cock and started sucking, immediately trying to deep throat all ten inches of her. I still wasn't totally used to that, and it was obvious, by the immediate choking and gagging that followed.

It only seemed to serve as a turn-on for Claire though, as she grabbed a fistful of my hair and started forcing her cock deeper down my throat.

Behind me, Jackie stood and watched, lighting up a cigarette and taking a long drag. She knelt down where Claire had been a few minutes earlier, and started playing with the plug, buried deep in my ass. "How does that feel, Jimmy boy?"

I gave a muffled "Mmfff," and both Jackie and Claire giggled.

"It's nothing compared to what it's gonna feel like, when you feel my big fat cock inside of you...are you ready for that, Jimmy boy? Are you ready for something a little bigger, to split that little boy pussy wide open, for you?"