tagTransgender & CrossdressersThe 21st Birthday Party

The 21st Birthday Party


To say it was a wild night would be an understatement. My 21st birthday was literally, the greatest birthday of my life. Of course, the best part of the night had been meant only as a prank that my friends wanted to play on me just for the fun. No one, not my friends and definitely not me, had expected it to go in the direction it had, but to this day I'm glad that it did. The night of my 21st birthday was the night that changed my life forever.

I had been waiting for weeks leading up to my birthday to finally be able to legally buy my own beer. Never again would I have to ask an older friend to buy alcohol for me, or sneak in and out of a liquor store and hope that the guard didn't notice that I had sneaked something off the shelf. Now, I could walk right in, grab whatever I wanted, and go right up to the register and pay for it without a problem.

On top of that, I knew my friends were planning to throw a big party for me to celebrate. I didn't know much about what they had in store, as my best friend Eric and my brother Steve were planning it, and they were very good at keeping secrets. So the most I could do was sit back and try to wait as patiently as possible until the big day finally came.

At 20-years old, going on 21, I was a pretty good looking kid. I had short brown hair, although it wasn't a crew-cut or anything like that. I weighed around 160 pounds, with a bit of muscle on me too. Brown eyes to top it all off. I'd always had good luck with the ladies, since I had first started dating in my early teen years. I had been in and out of one particular relationship with a girl named Stacey, all throughout high school. In between the few break ups that we'd had, I had been with three other girls too.

As I said, it had never been a problem, but I had finally broken up with Stacey for good just shortly after high school ended, and at that point I swore off dating all together. I felt like there was just too much drama involved, and with women in general. So for the most part, since ending it with Stacey, I had just been doing the whole random hook-up thing. One night stands, and that was that. The problem was, even that was starting to get old now. It was hard to find a girl who was interested in a one night stand, and most of the time they wanted you to dedicate yourself to them once you had done the dirty deed together.

But the idea of settling down was not something I wanted to do yet either. It had been about six months since I'd been laid because of this new line of thought that I had found myself stuck with, and I wasn't sure when I would get laid next.

I hoped that I might get lucky at my party. Finally, the day came, and since my birthday fell on a Friday this year, I requested the entire weekend off from work to celebrate. Luckily, my boss was nice enough to give me what I asked for. I finished up my Thursday night shift, went home, and called it an early night... the sooner I got to bed, the sooner the big day would roll around. As my birthday dawned, I got myself up, showered, and put on a pair of sweat shorts and a plain white t-shirt.

I slipped on my shoes, and out the door I went, making my way over to my brother Steve's house. When I got there, I knocked twice and a few moments later the door swung open to reveal Steve's friend Nick.

"Jimmy boy," he shouted, giving me a bear hug. We both laughed, and he backed off, stepping aside and motioning me into the apartment. "Happy birthday brother, how you doing?"

"Not bad Nick," I replied. "Where's Steve at?"

"He's out setting up your party for tonight. He should be back around 5:00 or so. He told me just to chill with you here for a while until he gets back."

So, Nick and I cracked open a couple of beers to pre-game and dropped down on the couch in front of the TV. We flipped through the channels for a while, but there really wasn't anything good on so we turned off the TV, and decided to just sit there and bullshit for a while.

"So tell me," I asked quickly, "What's my brother really got planned for me tonight?"

I was hoping to get Nick to slip up and tell me what was happening... I underestimated him though, because he was apparently a locked vault when it came to that question.

"Sorry buddy, but your just going to have to wait a few more hours and see for yourself," he said, with a smirk.

"Damn," I said, standing up and tossing my empty can of beer. "I've been waiting for two months to see what the hell Steve and Eric have planned. I'm starting to go crazy here dude!"

"Well, take my word for it... it's going to be worth the wait."

"I fucking hope so," I laughed.

Just then, the door to the apartment opened and in walked Steve and Eric.

"Hey, there's the birthday boy," my brother shouted.

After a brief hug from my older brother, I shook hands with my best friend Eric who gave me a pat on the back and a smile.

"Dude, tonight's going to kick... fucking... ass," Eric said.

"He isn't lying," Steve chimed in. "We have one kick ass night in store for you little brother. You're going to love it, I promise!"

"So, when is everyone getting here," I asked.

"Oh, no one is coming here. We rented out a fucking hotel room for this shit. That way nothing here in my place gets ruined," Steve explained with a grin.

I laughed, figuring that if he had to go out of his way to rent a hotel room so that his apartment wouldn't get fucked up, then they definitely had to have something good in store for me. We hung out at his place for a little while longer, talking and laughing and having a few more drinks to get ourselves warmed up for the night. It was still early, and Steve didn't want to get to the hotel until a little later. By the time we actually left the apartment, it was probably about 7:30. We got into Steve's car, and pulled off, heading towards a place that he said wasn't too far from where he lived.

"We'll have to stop off somewhere first though," he said, making a detour from his original path. We stopped a few minutes later, in the parking lot of the local beer distributor.

"First off, it's time for the birthday boy here, to buy his first legal case of beer. Here's $30, go in and grab whatever you want."

Steve handed me the cash, and I thanked him, jumping out of the car and walking into the store. I took a few minutes to walk around, before grabbing a case of Coors Light, and carrying it up to the register. The cashier gave me a look as I sat the case down on the counter, and before he could pop the question, I reached into my pocket and pulled out my ID, slapping it down on the counter for him to see. He examined it for a few moments, before nodding his head, and sliding it back towards me.

He rang it up and I paid, waited for the change, then grabbed the case and made my way back outside to the car. Steve popped the trunk open for me, and I set the beer inside, slamming the lid shut and jumping into the back seat again.

"Alright, we're good to go," said Steve.

"Then let's get fucking moving," Nick shouted, and we all started cheering as Steve peeled out of the parking lot.

Fifteen minutes later, we arrived at a nearby hotel and Steve parked the car. He told us to wait outside until he had paid for the room and got the key, not wanting the receptionist to see that we were bringing alcohol into the building.

A few minutes later, Steve opened up a side door leading directly into the staircase for us and we piled into the building carrying all of the alcohol. Up the stairs we went, to room 407 which had been assigned to us by the front desk. When we stepped inside, I was shocked at the size of the room; it was pretty fucking big. There were three bedrooms, two sofa's and a lot of room.

"How much did you spend on all this shit," I asked.

"Don't worry about it," replied my brother. "It was a lot of money, but well worth it for my little brother."

I almost felt bad that he had spent so much, but I brushed it off, knowing that he didn't want me to pay too much attention. We opened the fridge, which was empty, and opened up the cases of beer we had brought with us to proceed with filling the fridge up.

By the time we finished, it was 8:30 at night, and time to really start partying. A few other people had shown up by now. Two of my brothers friends, Mark and Tyler along with their girlfriends Jessica and Ashley. Then three of my friends, Alex, Shane and Shane's sister Whitney.

The first hour breezed by, and I was already starting to feel just a little intoxicated at this point. I stepped outside onto the hotel rooms balcony for some air and lit up a cigarette. I had only taken a few puffs when Nick stepped outside alongside me and tapped me on the shoulder.

"You're going to want to come back in now," he said with a big grin. "Your present is here." "My present?"

I laughed at the look on his face as he stepped back into the room, and I put out my cigarette and followed behind him. Once inside, my eyes fell upon a woman, who I had to say was just straight up fucking sexy. She was tall, taller then me... probably 6'1" with long black hair and deep blue eyes. She had a very curvy body, her tits weren't too big but definitely not too small and an absolutely perfect fucking ass. She was dressed rather skimpy, wearing only a bra and a pair of very tight jeans.

"Jimmy... this here is Brianna. We invited her over to dance for you," said Steve.

Everyone started to laugh, and I gave a chuckle as well as I realized that Brianna was obviously a stripper they had hired for my party. I wasn't going to complain at all... she was so fucking hot I would be a fool to speak out against it. My friends pushed me over to a chair they put in the center of the hotel room and got me to sit down. When I did, Brianna stepped forward and they started playing some sort of club mix dance song for her to dance to. And I have to say, she was one hell of a dancer, as she started moving about the room in front of me.

I was already having a great time within the first few seconds, and as she danced, she moved closer to me and sat down on my lap finally, and prepared to give me a lap dance. She reached behind her and unsnapped her bra, revealing her gorgeous tits, before leaning in close and draping her arms around me. Her tits were now right up in my face, and I breathed in her scent, groaning as my cock began to throb in my pants.

She performed a brilliant lap dance that lasted about a full minute before she stood up again, and before I could show my disappointment she undid her pants and started to slide them down her smooth legs to reveal she was wearing a black thong. Once again she moved back onto my lap, arms around my neck again and resumed her dance.

I was really getting into it now, and Brianna was being extra seductive about it, which did not help too much. Especially when, to my surprise, she leaned in and kissed me on the lips and slid her tongue into my mouth. I groaned, kissing her back. I could feel something hard against my own straining cock, and couldn't quite figure out what it was but I was also too caught up in the moment to figure it out.

As we made out more and more, I could hear a few of my friends starting to laugh as well as my brother... what the hell was so funny, I thought. I opened my eyes, and Brianna broke the kiss and slid off of my lap and that's when I saw the bulge in the front of the thong and what was clearly a seat of balls hanging out of the sides of the thong. Brianna was actually a shemale.

"What the fuck!" I said, stunned, and the room erupted into laughter as she moved back onto my lap again, smiling seductively at me.

"Happy Birthday Jimmy!" she laughed.

I couldn't believe it, but her voice didn't give much of any indication that she was packing. Nothing about her did for that matter. She was so fucking hot, I just couldn't believe what I had just discovered.

"Happy birthday little brother," Steve said patting me on the back.

"I hope you don't hate me for this one, but I thought it would be pretty fucking funny to get one over on you like this."

The shock started to wear off a little, and I couldn't help but laugh myself as Brianna moved off of me again. She slid out of the thong and now standing before us completely nude, I could see her cock dangling between her smooth legs. It was semi-erect and probably about 8 inches and a bit thick too.

She continued dancing in front of us now, as Steve and everyone else continued laughing and so did I. After a while, Brianna slipped back into her thong and a shirt and Steve gave her a beer. The party was getting even better, and it was coming up on midnight now. We had turned down the music a little, so as not to piss off anyone in the other rooms and cause any trouble, but we were still having a lot of fun.

At about 11:45, I stepped back out onto the balcony feeling a little more drunk now then I had felt earlier. I lit up a new cigarette and took a drag, leaning against the railing and looking down at the street below, a big smile on my face. When I was drunk I always laughed at everything and smiled all the time. I heard the sliding glass door behind me open, and Brianna came out to join me by the railing, shutting the door behind her.

"Hope you don't mind me coming out here," she said. "I needed a smoke myself."

"I don't mind at all," I said, slurring my words a little.

"You got a light?"

"Yeah, definitely!"

I reached into my pocket and retrieved my zippo, flipping it open and holding it up for her to light her cigarette. Once it was lit, I put the lighter away again and watched as she took a drag. I wasn't sure if it was the alcohol, or how I actually felt... but even now that I knew she had a dick, I still found her incredibly sexy.

Especially standing there smoking that cigarette right in front of me, with the moon light shining down on her.

"So birthday boy, are you having a good time?"

"Huh? Oh, yeah, yeah I am, it's a lot of fun."

"That's good," she giggled. "You aren't mad at your brother?"

"Nah, not at all. We play pranks on each other all the time. I don't think he's ever done anything like this before, but I don't mind or anything."

"Well that's good. So, how old are you today anyway?"

I guess they had left that part out when they hired her to come here.

"I'm 21-years old... finally able to buy beer on my own."

"Wow, you look younger than that, I have to say. Maybe about 18 but you don't look 21 years old to me."

"Well, I take that as a compliment," I said, and she laughed as we both took a drag of our cigarettes.

"How old are you? I mean... if you don't mind me asking?"

I expected her to get pissed at me for asking, and actually regretted the question as soon as I had asked her. To my surprise though, she shrugged her shoulders and didn't seem mad at all.

"Take a guess," she said.

Just looking at her, I thought maybe a few years older than me... probably in her mid to late twenties, I suspected.

"Maybe about 28?"

"Wow, that's definitely a compliment," she laughed. "Actually, I'm 36-years young," she said. "No shit," I said, shocked once again by this beautiful woman.

"You don't look a day older than 28, I swear."

"Awe, that's sweet."

We continued talking, and drinking, just the two of us out on the balcony while everyone else stayed inside and drank. It had started to rain, but we were dry under the roof above us that came out far enough over the balcony to keep the rain out. No one inside felt like coming out.

Before either one of us knew it, it was almost 2:00 in the morning. Our conversation had turned a bit flirtatious, and had been growing since then with the both of us flirting more and more heavily. I think she was a bit surprised at first that I was coming on to her, even after finding out that she had a penis. After a while though, she seemed to warm up to it and started going along without much hesitation. I sat down on a chair on the balcony and cracked open what I intended to be my final beer for the night, and took a swig.

"You know... I have to say. I have never seen a woman more beautiful than you Brianna."

"Oh really? Did you forget that I'm not your typical woman?"

"No, I remember," I said shaking my head. "But I don't care... you're a little different sure, but your still fucking beautiful."

"Well," she said blushing. "Thank you... did you like my dance earlier?"

"Oh, I loved it. Every second of it."

"Mm, really," she asked, coming over and sitting down on my lap in a similar position to earlier. She was still only wearing her thong as she sat down on me, and I could feel the stiffness of her cock against me as she brushed a strand of hair out of her face.

"Mmhm... I loved how soft your lips were too."

"Mm, all the better to kiss you with baby," she purred, leaning in and kissing me softly on the lips.

I moaned, as her tongue came sliding into my mouth again. My hand moved up her smooth legs and under the t-shirt she was wearing to massage her breasts. We were getting more and more intense with every passing moment, and I could not believe that I was getting into this right now. Our lips parted, and she went to start kissing and sucking on my neck. I started breathing a little heavier as her warm breath blew against my ear.

"Tell me birthday boy... I'm guessing you don't have a girlfriend... am I right?"

"Mmhm... yeah, you are right."

"Good," she whispered, blowing warm breath on my ear again.

She started sucking and gently biting on my neck, leaving a pretty large size hickey. Then she stopped and pulled my shirt off, tossing it to the floor and started licking and sucking my nipples. I moaned louder this time, the feeling of her warm set tongue against my nipples driving me crazy.

She started sucking on my chest, just above my left nipple, leaving a second, larger hickey in the place of her lips.

"I've left my mark on you now," she said seductively. "You're all mine now baby."

"Mm, you can have me babe," I replied, slurring a little.

"Wanna go inside... and take this a little further?" she asked.

"I think that sounds like a great idea," I answered.

She slid off my lap, took me by the hand and pulled me off of the chair. I opened the sliding glass door and we stepped into the hotel room off of the balcony. Everyone who stayed had fallen asleep, and I noticed a few people must have left because the crowd was smaller now. Down the hallway, and into one of the three bedrooms we went, shutting the door and locking it behind us. Once we were in there, Brianna turned around and shoved me down hard onto the soft mattress. She jumped on top of me, and pulled my sweat shorts down and threw them aside.

She removed her t-shirt, throwing it to the floor and revealing her breasts again. With me now only in my boxers and her only wearing her thong, Brianna got on top of me and leaned down, kissing me hard on the lips and grinding her ass against my cock. I grabbed her by the hips and flipped her over onto her back, pulling the thong off and throwing it to the floor.

Her hard cock sprang free, now standing at full attention... it was huge. I'm not sure what came over me, but I leaned in and started to lick the head of her shaft, causing her to moan softly underneath of me.

"Oh fuck Jimmy... y-you don't have-"

I silenced her by taking her entire length in my mouth, and she gasped at the feeling of my hot mouth around her. I took as much as I could, until she reached the back of my throat and I jumped, gagging just a little. She sighed, running a hand through my hair and forcing my head down a little more over her cock. I continued to gag each time that I went down, until I adjusted and had managed to take her entire length after some work.

"Oh shit," she groaned. "You're really good at this."

Report Story

byWhiskeyIsGood© 9 comments/ 84127 views/ 121 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: