Chapter 1 – Chapter 1

Jane and I had been friends since we met at our university's freshman orientation. She was witty, funny, ridiculously cute and we had the same tastes in pop culture. Over the next two years the more time we spent together, the more I fell in love with her and I wanted to become more than just friends.

Unfortunately for me, Jane wasn't interested in a serious relationship. I was her best friend and that seemed like that was all that was meant to be. Then, a few weeks from Halloween, she entered my apartment positively beaming.

"I know what we are doing for Halloween!" she said as she hopped onto my bed. "You know my friend Tim from the theater company, right?" I knew Tim, sure. I didn't particularly care for Tim. He was starting to monopolize Jane's time, and when we were together she spent most of the time talking about Tim.

Fuck Tim.

"Yeah, I know Tim…theater, right?" she nodded and continued on.

"He's throwing a theme party: Cowboys and Hookers, and…We. Are. Going!" she said, playfully poking my chest with each word.

"Cowboys and what?" I asked, understandably confused.

"Hookers. The women dress up as cowboys and the men dress up as hookers. It will be fun! And it will be great practice for my major." Jane was studying to become a film makeup / special effects artist. Her work was good. Really good. How this would help, though…

"I don't know," I resisted. "I mean…hookers?" Jane grabbed my hands into hers and kissed them.

"Please! I want to go and I need a date, and you're the first person I thought of." It was as if she knew what buttons to press. An actual date. With Jane.

"Okay, if you really want to."

"I really, really want to!" she giggled before kissing me on the cheek and texting her RSVP to that fucker Tim.

Cowboys and Hookers, oh my.

***

"Well, what do you think?" Jane asked, her voice deep, gravely, and convincingly male. she extended her arms and slowly turned, giving me a 360-degree look at her handiwork. Her soft, feminine features were hidden behind loose-fitting Western wear and a beard and mustache.

"You really have a gift," I answered. I barely recognized the "man" in front of me.

"And how is this for attention to detail?" she asked as she unsnapped her button fly. She playfully pulled her jeans down and a realistic long dildo – complete with veins and balls – jumped out, held securely in place by a strap on harness.

"You really go the extra mile," I joked.

"You're right, I do! Now to get you ready!"

***

"Go ahead and take a look," Jane said, her hand motioning towards the full length mirror across the room. I got out of my chair and stumbled a little bit; I was a bit unsteady on my feet, which was to be expected. I'd never worn heels before, let alone the patent leather stilettos Jane picked out for me.

"You're going on a date with Jane," I kept repeating to myself as she took my hand and helped me to the mirror. When I finally got a chance to see what she'd been doing while I was in in that makeup chair, I was floored. Jane deserved an Oscar or something, because the woman staring back at me was fucking hot.

Before she started making me over she told me my sleight frame was perfect for this transformation, and it turned out she was spot on. The perky B-cup falsies that filled the lace bra under the tight strapless top looked natural on my 100-pound body. With the exception of the thick, bright red lipstick, the makeup was tastefully subtle. I had misgivings about her wardrobe selection when she laid it out for me, but now that I was seeing it all put together – the stiletto heels, thigh high stockings, garter belt, short black skirt – it screamed "fuck me" while just falling outside the "trashy slut" category. I gently ran my fingers through my wig and batted my fake eyelashes and thought that if I met the woman I was looking at, I would definitely want to fuck her brains out. My cock was straining against the lace thong it was tucked into.

Yeah, I would definitely fuck her.

"Good?" Jane asked, with a wry smile on her face.

"More than good," I responded, turning from side to side so I could admire my body. Jane handed me a purse, locked her arm in mine and gave me a kiss on the cheek.

"Let's go."

***

The party was a few minutes away by car, but Jane wanted to take the 20 minute walk there. She claimed it was because the weather was perfect – which it was – but I figured she just wanted to show off her handiwork. I had a firm grip on her arm to not only keep my balance, but to give me moral support as well.

Jane assured me that I would get the hang of the shoes pretty quickly, and she was right. A block and a half into the walk I no longer had to hold onto her, and my nerves melted away as the guys we passed made no attempts to hide that they were checking me out. The surge of confidence put a literal bounce in my step as I strutted down the sidewalk with the gait of a runway model, my B-cups gently bouncing with each step.

"What's wrong?" Jane asked as I slowed to a stop. She followed my gaze down the sidewalk towards a main intersection. There was a group of five guys, all in Greek sweatshirts, waiting for the light to turn. Having guys walk by and ogle me was one thing, but the prospect of standing on a street corner beside them started to fill me with dread.

"It's ok," Jane said, taking my hand. "I tell you what.. you play along and after the party, we'll go back to your place and I'll fuck you."

Startled, I turned towards her with a confused look on my face. she nodded and gave me that smile that had always bent me to her will.

"We will go back to your place, and I will fucking fuck you," she said as she walked towards the street corner. She looked over her shoulder at me and said, "Oh, and don't say a word to anyone. Your female voice is total shit."

***

The fraternity brothers had definitely been drinking. The smell of alcohol filled the air as they joked around with each other. They grew silent as we came to a stop, practically surrounded by them. Like the other guys I encountered during our walk, they were all checking me out, and we obvious about it.

"Play along and we'll fuck," she had told me. Inspired by that promise, I flashed them smiles and playfully turned my body from side to side, giving them a look at my profile. I had to admit that the role playing was a bit of a turn on as I watched them check out my legs, my ass, and my tits. I reached up and pretended to adjust my tits in my bra, flashing the group a smile.

"Dude, your girlfriend is fucking hot!" one of the strangers exclaimed.

"Who, her?" Jane replied, pointing her thumb back at me. "She's not my girlfriend," she scoffed. "I needed a date for a party so I hired an escort. She's worked for me before so I know she's guaranteed to be a good time." I felt my cheeks grow warm as I started to blush. Blood started to flow to my tucked cock, and I thought it was going to burst out from the confines of the thong.

"That's fucking hot," one of the other guys said, a huge smile on his face. "How much does she charge?"

Jane looked at each of the men, nodding her head as if she was counting them.

"I'd say $10 to give you a blowjob." I was too stunned by what I heard to say anything. I just stared silently at Jane as she looked over her shoulder at me and flashed that same "you'll do anything for me" smile.

"So wait, anyone with a twenty gets their cock sucked?" one of the other guys asked, somewhat incredulously.

"No, no, no, you misunderstood," Cowboy Jane responded, maintaining her convincing male voice. "You give me $10 and she'll take you behind those bushes and suck all your fucking cocks." We all looked at the thick, overgrown hedge row that obscured the empty office building behind it. I grabbed Jane's elbow and pulled her aside.

"What are you doing?!" I whispered from the side of my mouth. She looked back at the guys who were fumbling with their wallets – who carries cash the days – and held up a finger, asking them for a moment.

"I'm helping you get what you've wanted," came her cryptic answer. My dumbfounded silence made her shake her head and sigh.

"Remember a month or so ago when my computer crashed and you lent me your laptop for a week?" I nodded, not sure where this was headed. "Well, I saw your browser history.* My heart sunk from the realization of what she was saying.

"It was all porn," she continued. "And whatever wasn't gay porn was bi-male-male -female porn." She looked back at the fraternity brothers and the money clutched in their hands. "You clearly have an obsession with cock, so here's your chance to experience it."

I hated to admit it, but she was right, and I blamed my new roommate for my recent sexual transformation. Mark moved in at the beginning of the academic year, and from day one he had this annoying habit of going nude in the house. Whenever I'd tell him to put clothes on, he'd say no, telling me that he wasn't going to change who he was.

I tried to ignore him, but it was difficult to ignore a 10" dong swaying from side to side as he walked down the hall, or how it seemed to be pointing at me as it flopped over Mark's leg while he sat next to me on the couch. A few months of that rod being a constant presence led to it creeping into my masturbation fantasies. I was surprised by how intense my orgasms were when I would think about that big, beautiful dick.

I became a bit conflicted – I was still deeply in love with Jane, and wanted our relationship to move to the next level, but I had this constant lust for his dick, which slowly turned into a lust for cock in general. My porn selection started to focus on big dick porn, then on gay porn. If the video featured a woman, I usually needed some guy-on-guy action to get me to cum.

Jane was right. I had a cock addiction. A constant craving. And there were five willing ones right in front of me.

***

"Okay, a few rules," Jane said after we retreated behind the privacy of the hedges. "Your money bought a blow job. That's it. No fucking, no fondling, just your dick in her mouth." She paused momentarily to finish counting the singles. "And remember, I'm taking this slut to a party, so I don't want her to get messy. No pulling out, just cum in her mouth. Don't worry, she'll swallow. If she starts to pull away, just hold her there."

Jane's rules didn't register with me. I was already kneeling in front of one of the guys and was undoing his jeans; I was so focused on getting to his package that I barely knew she was talking. I pulled his pants down and his cock snapped free, slapping me in the face.

Those nights of fantasies about cock didn't prepare me for the feelings that cock sent raging through my body. With a thick, hard cock literally staring me right in the face, a carnal desire took over. I grabbed his cock firmly in my hand and rubbed the head across my painted lips. I wanted to tell him how much I loved his cock, but I remembered Jane telling me my girl voice sucked. I looked up at him and flashed him a wide smile before running my tongue up and down the bottom of his head. I resisted the urge to immediately shove his dick down my throat and instead let the tip of my tongue continue to tease him. I heard the sound of the other pants unzipping as I let my tongue swirl around his purple helmet over and over like it was a lollipop, maintaining eye contact with him the whole time.

I could sense people drawing closer, so I looked to either side of me and saw the other frat brothers closing in, stroking their dicks. I felt my own cock stiffen even more as I realized that I was the one making them so hard. It didn't matter to me that they thought I was a woman, all that mattered is that they wanted to use my mouth.

I looked back at the dick I had started to gently stroke and saw precum oozing from the slit. I leaned in and ran my tongue up the underside of the shaft and over the head, scooping up the precum that had leaked out, I licked another stream of precum from his head and left my tongue out. I looked up at him and smiled, showing him the little pool of his juice on my tongue, his early reward to his blowjob whore, before I closed my mouth and swallowed.

"Fuck!" he moaned, pushing his hips forward. My heart raced with anticipation as I opened my mouth and welcomed him in, his bulbous head spreading my lips and sliding over my tongue.

"Oh my fucking GOD!" I thought as I finally felt a hard, warm dick in me. I gently bobbed my head up and down, my painted lips leaving streaks of red on his shaft. I was in absolute heaven. He rocked his hips back and forth in rhythm with my mouth, the tip of his dick finding the back of my throat with each push. I looked out of the corner of my eyes to either side of me and saw two of the fraternity brothers, dicks in hand, stroking and waiting their turn. I reached out and wrapped a hand around each cock and took over for them.

I found myself wishing I could have an out-of-body experience and watch this: Me, all dressed up with a cock pumping in and out of my mouth with a hard dick in each hand. My hands worked faster as his hips picked up their own pace. In my fantasies, I was a deep throat blowjob master. In reality, well, I had a gag reflex. Not bad enough to pull away from his thrusts, but noticeable enough that it turned him on and made him keep going. Drool was spilling out of the corners of my mouth as the college stud fucked my mouth like a pussy. He started to moan and groan, pumping faster, and then it happened…

The moment I had dreamed of most…

I felt his body stiffen as his shaft started to throb. He let out a final groan as his cock exploded. I had eaten my own cum before, but this? This was bordering on magical. The sensation of a cock throbbing in my mouth, made me see stars. Delicious thick jets of salty cum shot against the roof of my mouth as I swallowed and gulped as quickly as I could. One of the things I enjoyed about eating my own cum was the variety of texture and taste, and this was no exception. His load was so much thicker than any of mine, and so much bigger. I didn't think his orgasm would ever stop! He pulled his dick out of my mouth, my lipstick smeared all over it. I licked the last savory drop of jizz from his dickhead and he backed away. My heart was racing, and his cum shot unleashed a ravenous cum slut inside of me. In that moment I wasn't interested in drawn out, erotic blowjobs. No, I wanted to drain the other four men's balls as quickly as possible, gulping down every delicious drop.

I moved my head over to the cock in my left hand and took his head in my mouth. My tongue swirled around his head as my left hand jerked him faster and faster. He let out a muffled "fuck!" before his dick started to spasm, blasting rope after rope of cum in my mouth. His load was sweeter than the first, and not as thick. It was a powerful orgasm, though, as each spurt shot deep into the back of my throat.

I could sense the dick in my right hand was about to cum, so I quickly shifted my mouth's attention to him. I barely got his purple helmet into my mouth before he deposited a thick pool of cum in my mouth. Channeling the girls in some of the porn I watched, I didn't swallow; As his cock spurt jizz into my mouth, I held it there, collecting it all. After he finished cumming and pulled out, I looked up at him and opened my mouth, showing him the delicious gift he deposited for me. I tried to gargle with it like they do in the movies, but I didn't have the skills for that yet. I swallowed it in one big gulp and then showed off my empty mouth to him. I wanted him to know what a good little cum bunny I was!

The last two dicks were standing behind me, so I spun around and reached for both of their poles. They were pretty nicely hung, and at any other time I may have used my mouth to edge them for hours, but my cum lust was controlling my brain. I used my grip on their cocks to guide them closer together. I placed both of their heads together, opened my mouth as wide as I could, and tried to suck them both in.

Their dick heads were so big I could barely fit half of them in. My tongue danced all over their tips, getting coated with their salty precum. My hands worked their shafts, my fingers gripping them and running up and down their full length. My fingers moved to the base of their shafts, then to their smooth balls. As I massaged their balls, each hanging heavy with cum, I could feel their hands return to their cocks and they started jerking. They started breathing heavier and heavier until they let out a simultaneous moan, both reaching orgasm at the same time. They flooded my mouth with their jizz, a massive sperm cocktail filling my mouth. I gulped as quickly as I could, goosebumps forming on my skin out of the sheer pleasure of two dicks completely emptying their balls into my mouth.

When they finished cumming the five guys put their shorts back on, thanked Jane for the use of her whore, and they left. Jane walked over to me and pulled a tube of lipstick out of my purse. She knelt in front of me and kissed me on the lips for the first time ever.

"That," she whispered as she fixed my lipstick, "was the sexiest thing I've ever seen."

***

All I wanted to do was cut the evening short: we'd go back to my place and finally fuck as promised. But Jane wanted to make an appearance at the party, so we did. People came up to me and complimented me on my outfits and make-up; some of the cowboys went so far as to reach under my skirt to make sure I had a dick. The time spent at the party was a bit of a blur. All that was on my mind was Jane's promise. Jane's promise and the birth of my inner cum slut. My cock would twitch every time I thought back to those frat cocks, the five loads in my stomach, and my appetite for more.

"You ready?" Jane asked, snapping me out of my cum-filled trance. I nodded and we headed back to my apartment.

Where I would finally get to fuck Jane.

***

We walked into my apartment and, as usual, Mark was sitting on the couch watching TV, manspreading with his 10" cock resting on the couch cushion. He looked over at us with a confused look on his face. We must have been quite the sight: a bearded cowboy and some cum gulping escort. As I looked at his massive dick, my inner cum slut took over once again. He had been taunting me and tempting me with those smooth balls, the long veiny shaft, the perfect bulbous head, I was going to finally take control. I walked over to the couch and took off my wig, tossing it to the side as I knelt in front of him. I grabbed his pole with both hands and lowered my head onto it.

"What the?" Mark asked, even more confused, but doing nothing to stop me. Not that he could, really. My brain was singularly focused on getting his cum. He laid back and closed his eyes and let my hands and mouth do their work. Jane unbuttoned her jeans and stepped out of them, her strap-on standing at attention. I took his dick out of my mouth and rubbed the shaft all over my face.

"Fuck, I've wanted this cock for so long," I confessed to him. "It's so fucking perfect," I said as I licked and kissed all over the head. I lowered my head and licked and sucked on the balls that would soon be feeding me my cum nightcap. The sounds of me sucking and slurping on his nuts was drowning out the television and made him moan. I ran my tongue back up his shaft and around his head before I took his dick back inside my mouth. I got on all fours for better stability as I moved my mouth up and down, angling my head so that I could fit as much of his ten inches in me before I would start to gag. He put his hands behind my head and gently guided it up and down, letting out satisfied moans as my mouth made love to his prick.

Jane had fished a bottle of lube out of my purse and poured it all over her strap-on. I didn't realize she had moved behind me until I felt something press against my hole. I pulled Marks' dick out of my mouth and looked over my shoulder at Jane's smiling face. She had removed her shirt and I got to see her perfect, perky A cups for the first time. Her nipples were so hard they could cut glass.

"What did you think I meant when I said I would fuck you?" she smiled, pouring more lube down my crack and all over my hole. I answered her question by pushing my hips backwards into her, the head of the strap-on spreading my hole and pushing into my ass.

"Are we going to talk, or fuck?" I asked, the events of the evening making me bolder than ever. She smiled and grabbed my hips and started to push the length of the dildo into my welcoming ass. I moaned loudly as she pushed in and out, the head of the dildo massaging my prostate. Mark pushed my head down onto his cock and started to hump my face. He let out a loud scream, followed by a geyser of hot jizz. This was the biggest, most powerful load of the evening, and no amount of swallowing could possibly drink it all. I pulled off his cock before I gagged from all the cum and jerked his dick, painting my face with rope after rope of his man juice.

Jane was pumping my ass harder and harder, pouring lube down my crack to keep my man pussy well lubricated. She was fucking me with the full length, her hips making a slapping sound against my ass as she rammed me. The sensation was more than I could handle.

"Oh, fuck!!!" I yelled out as my cock finally got the release it needed all night. Jane pushed all the way inside of me and reached around, catching my spurts of cum in her cupped hand. I couldn't believe I was cumming without touching my cock, but the events of the evening, and Jane fucking my ass with her cock, was hotter than I could have ever imagined. Once the last drop of cum dropped into her hand she slowly pulled all nine inches of her strap-on out of me and we collapsed on the couch next to Mark.

We looked at each other and smiled. Mark's cum had utterly glazed my face; my body heat made the semen watery, causing it to run down my face and dripping onto my fake breasts. Jane brought her hand to her lips and slurped my thick white load into her mouth. She leaned towards me and we kissed, swapping my cum back and forth, sharing my salty seed, both of us swallowing down our share of the load.

Jane lay her head on my shoulder and let out a deep sigh.

"Mmmm. Best. Boyfriend. Ever."