My Journey

i contemplated leaving this experience out of the story but opted to keep it in the name of being thorough. There is some nonconsensual stuff involved so if that's not your thing, maybe skip this part.

I woke up the next morning in bed. I'm not sure exactly how I got there but the smell of breakfast was filling the air. Mmnnnn....

Breakfast was amazing. We all showered after we ate and Alex headed out after giving me his phone number with Jack's blessing.

Jack was packing for his trip, pulling his suit out of the closet as I was cleaning up the living room. As I was getting stuff together I came across the black teddy. I went over to the closet to hang it up.

"Why don't you keep that? In fact, take as much of this shit as you want."

"Really??!"

"Yeah, really. Get this shit out of here. The hats, the shoes, the clothes, the makeup kit. I'm sick of looking at it all. You're doing me a favor, believe me. Take whatever you want."

I didn't know where to start. Obviously I didn't need the shoes but there was so much stuff!! And I took a lot of stuff!! Panties, bras, skirts, lingerie, robes, even regular everyday clothes and a couple of hats!

I packed all that stuff in my car. Before I left, Jack pulled me into the kitchen and gave me a packet. It was all the stuff I needed to do to get the internship.

He gave me some pot and an old pipe. I looked at him inquisitively. "In case the urge strikes." I thanked him profusely and headed back to my apartment.

Same dumpy place, just as I left it. The light on the answering machine was blinking. Ugh. I'll check that later.

I tossed the packet into my desk and concentrated on getting the bags of clothes away. Once everything was away I realized I was getting hungry. A brief look through my kitchen revealed the fact that there was no food. Figures.

On my way to the grocery store I spotted a sign that I hadn't noticed before. "Jillian's Thrift Shop: clothing, shoes, accessories, furniture, household goods."

Shoes? Hmmm.... I'll have to stop back after I'm finished in the grocery store, which I did.

The place was fairly large. They had all the stuff your imagine in such a place but I was concentrating on the shoes. I sat down and tried on a couple pairs until I found my size. I found little white sneakers, a couple pairs of 2 and 3 inch heels in different styles, and a sweet pair of knee high boots with 2 inch heels!! I was really excited!!

I looked around at some of the women clothes. I did spot a cute blue plaid dress and a pair of leggings. What the hell, right?

"Did you find everything ok, miss?" the lady at the counter asked?

Miss?

"Um, yes. Thank you." I responded in my female voice.

I realized I was wearing a pair of cut off jeans and a tight pink top. Did I really look that feminine?

Back at my apartment i dug into my new shoes. They were all practically brand new. The sneakers fit well and were really cute. The boots were also really sweet. I tried on the 3 inch heels...damn near broke my neck! Women make it look so easy.

I settled on a brown pair of 2 inch heels. It was still challenging to walk but I spent the rest of the day in them. Only them.

I checked my answering machine. Mom called, a telemarketer, a couple hang ups, and my friend Brian.

"Yo! Yo! Yo! Bro! What is up? It's Bri! Hey, were going out to the club this weekend and wanted to know if you'll go. You've been a lame-o lately and we wanna get out and get some puuuussssy!!! Call me back!"

Great! Well, I guess it isn't all bad. This was my last spring break so I might as well have some fun.

I set it up for that Saturday. I'd drive so they could drink. I still wasn't up to drinking. I spent the rest of the day recovering from Jack's and trying out my new shoes.

But even on Saturday as I got out of the shower to get ready to go out, I really wasn't in the mood for it. You get cleaned up, full of anticipation, meet some girls, spend all your money buying them drinks, then they walk off leaving you with blue balls and a phone number- if you're lucky.

I guess I had been burned too many times. It's like they think they have some golden snatch between their legs. It gets old. Then if you do get to take them home it's like they are doing you some great favor.

But I went out anyway, of course, and just as predicted, nothing. Well, Joey got a blowjob behind the dumpster by some fat Asian chick. One for four, I guess. Sad thing is I probably suck cock better than that girl.

I drove my drunk buddies home, ooo-ing and aw-ing over the girls they just bought drinks for all night. Like it was a win. I humored them but I honestly wasn't surprised.

But I was surprised at the sign over the local gay bar. "Drag contest Monday night".

Drag contest? Hmmm...

I dropped my drunk ass friends off at home, pretty much tired of hearing Joey go on about the cum dumpster that blew him. We made big plans to do it all over again the next night.

Fortunately hangovers cancelled those plans. It was just as well. All I could think about was what a drag contest was. I even went so far as to call the bar and get details.

$20 cover, waived of your dressed and sign up for the contest, prizes of $100, $250, and $500 awarded at the end of the contest. Contestants had to arrive by 8:30 and the contest started at 9.

I thought it would be so cool to win something, even $100. I fooled the pizza guy the other night and the lady at the thrift shop thought I was a girl and I wasn't even trying. It kinda sounded like fun though it made me nervous.

Nervous or not, I spent the better part of the day learning how to apply makeup and not look like a guy trying to look like a girl. I also went through the clothes I had and picked out a black mini skirt, black thong, a black top that was lacy but cotton around the chest area and left my midriff exposed, black thigh highs, and, of course those boots!!

I was amazed at how cute I was all dressed!! I debated switching to the regular shoes but decided to stick with the boots.

I scoffed at myself Monday morning. No way could I go out in public dressed as a woman. What if someone saw me? It wouldn't be good. What a stupid idea. Instead I decided to take a look at the intern packet Jack had given me.

Just as I had expected: transcripts, essay, references, interview if it gets that far. I looked to see what the essay was about...mhmm...no problem, transcripts, just a phone call, references required from two professors in my major field of study and a letter of recommendation from my academic advisor. Yup, nothing unusual here... wait.

Academic advisor???? Professor Thompson?? I had been going out of my way to avoid him since the incident at the bookstore. And now I needed a favor? SHIT!!

SHHHIIITTT!!!!

I was pissed off for a while and decided not to let it ruin my spring break. I'm sure it'll all work out. I figured I'd make a few phone calls in the morning and get all my paperwork from the school, including the references and letter of recommendation without actually meeting with anyone.

By lunchtime I was thinking about the drag contest again. The apartment complex is like a ghost town during break so no one would see me leave or come back. And once I'm in the car, who is gonna know?

I had to do it. I wanted to do it. I felt like I needed it. And so later that afternoon I began the ritual of preparation. I was hairless from the nose down, except for my arms, which aren't hairy anyway. I spent forever getting my hair right. I couldn't tell you the last time to used a hairdryer and mousse. I actually got the mousse out of my roommates bathroom. My makeup was on point and I looked fucking stunning, if I do say so myself.

At 8:20 I was standing at the door of the gay bar talking to the bouncer. The music was loud.

"Name?"

"Huh?"

"Name? What's your name? So they can announce you for the contest."

"Oh, um, um, Lisa?"

"Ok, Lisa, go in the second door on the right. They'll review the rules with you."

So, apparently, I didn't understand the assignment. When guys dress up in drag, they really dont look like women. They look like female clowns. Blue eye shadow, excessive blush, globs of lipstick. A lot of them didn't even shave. It was a freak show, and here I was looking like an actual woman next to all these huge circus side show freaks.

But fuck it, i was there so I figured I'd give it a shot. I watched the other 'girls' go out on stage. They just kinda walked around, didn't do much dancing, and just blew a lot of kisses.

Then the stupidity of my situation hit me. I'm in a room full of gay men. They don't want to see a woman. They're into guys so the the unshaved, face painted freak in the flamboyant clothes is more in line with their desires.

And here I am looking like a slutty 20 something coed in a mini skirt with poofy hair. If I wanted to win anything I was going to need a plan B.

"Everybody welcome our next queen!! LISA!!!"

Here we go! I pranced myself out onto the stage like a supermodel at a fashion show. The club must have started out as a strip club because the stage was set up like one, stripper pole and all.

I got to the end of the stage, pulled my skirt up around my waist, and grabbed my cock while I danced. The place went wild!

I was surprised and encouraged so I went to the stripper pole, swung around that bad boy, and did a bump and grind against it. I stuck my ass out and slapped it. I smiled at some guys, made kissy faces, and winked at a few! I couldn't even hear the music over the cheers!!!

When I got backstage I realized my cock was rock hard! I had an absolute blast, even if the other contestants were giving me dirty looks.

After everyone took the stage they turned off the music and we all lined up. One by one they called our names out and the crowd responded.

"Third place!! Bobbie!!!" The crowd cheered.

I was disappointed. I figured third was my best shot at winning some money. Oh well. At least I had a good time.

"Our second place winner is!! "Juicy T!!!"

"And finally!! Last but not least!! The winner of our Monday night drag contest!! LISA!!!"

The place erupted!!

I stood there, dumbfounded. I couldn't believe it!!

"Do a victory dance for your fans!" the MC said in my ear. The music popped back on.

I pranced back out and did a few kneeling bump and grinds and pole spins for my adoring fans. It was such a rush!!!

I held the five $100 bills in my hand tightly as I walked to my car, still in disbelief that I won. Hadn't brought a purse or anything. In fact, I had even left my keys in my car under the seat so I wouldn't have to carry them around with me. Lady problems...

I had parked on the far corner of the lot in case anyone recognized car. I didn't want to be right behind the gay bar. It was nice and dark and secluded so it was less noticable.

I reached under the seat to grab the keys when I was suddenly yanked backwards by my hair!

I was spun around and tossed against the side of my car! Two huge, burly men stood in front of me.

"Yo baby, we saw you winking at us in there. Why don't you ride us like you were riding that pole on there."

They reeked of cheap beer and whiskey. Yuck!

The one that was talking practically fell against me, pushing his tongue into my mouth. I could feel his cock grinding against mine.

Initially I was repulsed by these huge drunk men. But when he started grinding his hard cock against me...I don't know what it was. I wanted him. And his friend too. I was suddenly amd overwhelmingly overcome with the desire, the need to please them.

I reached out and grabbed the quiet one my the belt and pulled him in for the surprisingly awkward three way kiss.

When they pulled away, I said as seductively as I could in my female voice, "do you guys want to fuck my mouth?"

Their eyes got big and they smiled at each other.

"Fuck yeah!" they both said at the same time and began fumbling with their pants.

Mere seconds later I was sitting on my heels eye level to their cocks as I stroked them. I found the heels were just the right height that I could squat down without having to kneel. The car behind me helped me keep my balance as they thrust their cocks in my face.

I can't begin to describe the amazing feeling of being in public, dressed as a woman, sucking two cocks in the corner of a dark parking lot. I lifted my skirt and pulled my thong aside so my cock popped out into the cool night air.

I worked them with my mouth, stroking the other when it wasn't their turn. I loved their grunts and moans as well as their conversation.

"Ah, fuck yeah, this is good!"

"Yeah it is!"

"It's been forever since I had a good blowjob. She sucks a mean dick, doesn't she?"

"Yeah, she's a fucking good cocksucker! It's better than I thought it would be."

"Nah, man, I told you, faggots suck the best cock!"

Faggot? Am I a fag? Even with all the cock I sucked, the cock I craved, getting fucked in the ass and dressing like a woman, I still didn't think of myself as gay. But I liked sucking their cocks and I liked something about them calling me a faggot.

I liked the humiliation of it all. Sucking their cocks while they act like I can't hear them. Like I didn't matter, like I was just a warm, wet hole for them to cum in.

The quiet one came first, pushing my head against the car and unloading a surprising amount of cum into my mouth as he howled. I swallowed what I could and the rest ran down my chin.

I used the other guys cock to scoop it up before I went to work getting his load. It didn't take long. He roughly fucked my face until he also released in my mouth. He pulled his cock from my mouth with a pop.

As I ran my tongue around my mouth to clean up the sticky cum and swallow it, I was suddenly and roughly lifted up and pushed against the car again.

I was shocked when the big guy pushed himself against again, this time his slimy, semi stiff rod ground against my rock hard cock. He kissed me deeply, tasting his cum and probably his buddy's too.

I'll never forget what happened next.

He broke our kiss and aggressively grabbed a fist full of quiet guy's hair and tossed him to the ground between us. He fell to his knees, clearly drunk and off balance.

"What the fuck, Ronny?"

"Don't you think you should thank the pretty lady for showing us a good time?"

"Dude, I'm not doing that?!!" His face was inches from my pulsing cock.

"Fucking suck her cock you little bitch!" He grabbed the back of his head and pushed his face onto my cock.

"Aaammmmpphhhh!!!"

The big guy then positioned himself behind his buddy, put his cock again the back of his head, and started fucking.

Yup!! Ain't that some shit??!! As he humped the back of his buddy's head, quiet guys mouth would ride up and down my cock! He was moaning in protest, which just made it feel that much better.

The big guy put his arms under my shoulders and grabbed fistfuls of my hair from behind. He pressed his lips to mine and kissed me roughly and passionately.

With my arms in the air now, I had little choice but to wrap them around his head. I pulled him even closer to me.

Inevitably I came right in quiet guy's mouth. He had stopped protesting for the most part. Well, until he realized I was pumping his mouth full of cum. Apparently he didn't care for it.

"Mmmmnnppphhhh!!!!" He was pushing against my thighs trying to get off.

Big guy was still going though. He wasn't kissing me anymore. He had his head on my shoulder, grunting, still holding my hair from behind, roughly humping quiet guy's head.

This became moderately uncomfortable for me. I had just cum and my cock was ultra sensitive but quiet guy's mouth was still wrapped around it. I could feel my cum running down my leg. Apparently quiet guy didn't swallow it.

Big guy suddenly stopped grunting and grinding. He squeezed me ridiculously tight and pulled my head back by the hair.

"Mmmnnnnfuuucckkkkk!!!!"

I felt some of is load splash against my stomach but the overwhelming majority of it landed on quiet guy's hair and dripped onto his face.

He was freaking out now. Pushing against me and the car, screaming around my cock. I don't think he cared for this.

When big guy pulled away, quiet guy shot up. He was very unhappy.

"What the fuck!! Are you some kind of sicko?"

"I don't know. Looked like you were enjoying it!"

"Enjoying it?? Ah, fuck you! I've got cum in my eye you motherfucker!"

"Ah! You liked it. You've always been a cocksucker!"

They started pushing each other as they argued. I slowly bent down and grabbed my keys off the floor of the car, which were also right next to my five $100 bills, and slid into the seat.

They had pushed each other a few feet away and weren't paying any attention to me. It was getting rough. I gave them one last look, started my car and took off, closing the door as the car moved away.

A quick look in the rear view mirror gave me my last glace of my would be assailants. Big guy was punching the shit out of quiet guy.