Drink or Dare


This is my very first story I've ever written. I've been an avid fan of Literotica for a long time and wrote this a few years back, but was afraid to submit it for a plethora of reasons, mostly fear I think. The story is semi-autobiographical with a ton of embellishment, because you know, no ones real life could ever be this good. I've been trying to work up the courage to submit it for a while and after a few failed attempts to have a volunteer editor take a look at it I finally just said fuck it and decided to go for it. Feel free to leave any feedback you like, but please be gentle as it is my first time and hopefully my writing will improve with time. If you are an editor and wouldn't mind editing my future contributions (as I hope there will be more) please feel free to let me know. I know its kind of long, but hopefully you'll find it worth the effort. Enjoy!


Ever since I was a child I had always fantasized about being a girl. Every chance I got I would sneak into my moms closet and try on her panties, slips, nylons and dresses. The feel of the sheer silks and nylons against my skin would drive me crazy. When I hit puberty and discovered the joys of masturbation these two activities seemed to combine perfectly. So much so that while jacking off dressed as a girl I would fantasize about being sexually used by men. Eventually I felt I needed a real life person to place my desires onto. Not wanting to pick anyone that lived close by, as these strange feelings might grow stronger and create awkward situations, I happened to pick one of the only people I knew in real life that lived far away, my cousin Dale. For years I had all sorts of fantasies about having sex with him while I was dressed like a girl. Some were hot and raunchy, like I would be his little prostitute slave and suck his cock and take it up the ass like a good little whore. Others where sweet and somewhat "innocent", like we were newlyweds and having our wedding night together.

Dale, the son of my aunt Lilly and uncle Dan, was blond with blue eyes with great broad shoulders and at 18 my rural cousin was a strapping example of manhood. At six feet tall and about 185 pounds he never seemed to have any problems getting the girls in his small town to take notice of him. While we were both the same age, mine was a different story entirely. With brown hair and eyes I was five foot five and 125 pounds sopping wet if I was lucky. Living in the city and going to such a large high school I don't think there was a single girl in my senior class who actually knew my name.

Several times a year, usually vacations from school, my parents would drop me off at my aunt and uncle's house. They lived on a farm outside a small rural town about four hours from the city, and just as I would go to their house to visit occasionally Dale would also come stay with us at times. Because we had a small house, we had always shared my bed when he would come to visit, but despite this I had never had any of my "other" feelings come up when he was over. Last year Dale had come down from the farm to stay with us for a few days. As we were lying in bed the first night, talking, he rolled over and looked me square in the eye. "Jim," he said. "would you suck my dick?"

My heart jumped in my chest! Was one of my deepest fantasies about to come true? Did he really want me to suck his cock? I had to play it cool. What if he was just fucking with me? What if he told our family I willingly gave him a blow job? I could be turned into the family "faggot" in no time and endure a lifetime of harassment and ostracism. I looked at him as calmly as I could. "I'll suck yours, if you suck mine." I replied.

To my delight he agreed and said he would go first. We set up a five minute timer on a wrist watch and the one receiving would tell the other if he was going to cum as neither wanted it in our mouths(well I did but I didn't want him to know that, at least not yet).

We stripped off our underwear and I was delighted to see Dale's cock for the first time. It was soft still but about six inches long and appropriately thick and looked absolutely huge compared to my five inch erection. I started a timer on my watch as he went down on me, and although it felt good I just couldn't enjoy it as I was so eager to get his manhood into my mouth. After about 3 minutes I stopped the watch and reset it and told him the time was up.

He rolled over and I crawled down and hovered my head over his crotch. He was starting to get hard but still wasn't fully erect, but even so it was growing and now was around eight inches. I gingerly placed one hand around his balls and the other at the base of his shaft and raised it towards my eagerly waiting mouth. Slowly I began lick the tip of his rapidly swelling cock and in no time it was fully engorged and rock hard. Now it was proudly standing tall at nine and a half inches. The only thing missing, I thought, was me dressed up as his little cock sucking whore.

I took the swollen purple head into my mouth and began running circles around it with my tongue as he closed his eyes, leaned back and softly moaned with pleasure. I slowly began working up and down the shaft, trying to get more and more of it into my eager mouth, but it kept bottoming out at the back of my throat four inches in. My own little boner was now erect and aching. Feeling the warmth of his throbbing cock sliding in and out of my mouth and through my lips was electrifying. I picked up the pace and pumped his meat into my waiting mouth with reckless abandon, gagging slightly every time it hit my throat. I was in heaven! I licked and slurped my way over every possible inch of that glorious pole completely oblivious to everything else but his cock in my mouth. Time must have flown by because it seemed like only thirty seconds later the watch beeper went off. By this time I was just too hot to stop. I kept sucking on his pole like my life depended on it, even though he was telling me the time was up and I could stop now. He tried to pull me off, but I was having none of it. In fact the feeling of his hand on the back of my head just made me hotter and more determined. I was getting my reward and no one was going to stop me. After fifteen seconds or so he realized I wasn't going to quit, so he just leaned back to enjoy the ride.

I was stuffing my face with his rod while I massaged his balls with one had and stroked the base of his shaft with the other. I popped his tip out and licked it eagerly, lapping up the leaking precum, then quickly sliding it back in to my waiting mouth where it repeatedly hit the back of my throat making me gag each time it did, but I didn't mind. I couldn't get enough of this hot rod and wanted to deep throat it with every fiber of my being, but lacking the experience I had to content myself with the 4 inches or so I could easily fit into my mouth.

I'm not sure how much longer I was there stuffing his cock into my mouth but I eventually felt his balls tense up. Again he tried to tell me to pull off, telling me that he was cuming, but I kept at it. His whole body tensed and spasmed as he flooded my mouth with his hot spunk. This sent me over the edge as well and I exploded all over the top of the sheets as I eagerly swallowed as much of his load as I could, but some still leaked out of my mouth and down my cheek. I stayed there till I was sure I had gotten it all and his dick started going soft. When I finally pulled off his cock he was looking down at me and I knew my secret was out.

"That was awesome!" he said.

"Thanks." I replied somewhat meekly.

"Where'd you learn to do that?" he asked.

"Ummm... no where really. Just kind of seemed natural I guess." I told him, trying to guard my answers.

"C'mon. You mean to tell me you've never done that before? I think skill at that level takes some practice. You've been sucking other guys cocks, you little faggot!" he exclaimed.

"No, no, no! This is the first time I've ever done that! I promise! Please don't tell anyone else!" I pleaded.

"I don't know man. I'm not sure I can keep this a secret, you being a cocksucker and all." he smiled at me.

"Hey." I replied. "You sucked my dick too! Don't go telling anyone or I'll say you're the same."

"Fuck You!" He hissed. "You blew me like a pro for a good fifteen minutes then swallowed my load and came all over the bed without even touching yourself! I think that makes you way more of a faggot than I'll ever be." He had me right where he wanted me.

"Please!" I begged. "Please don't tell anyone! I'll do anything! Please just don't say anything!"

He paused for a bit then said "I think I'd be willing to keep it our little secret..... on a few conditions." His lips pulled into a tight little sneer.

"Ok... well... what did you have in mind?" I asked nervously.

"Well, for starters I want a blow job pretty much any time I ask. No questions." he said sternly.

"Ok." I said sheepishly "What else?"

"You don't say nothing to nobody. If you ever mention this to anyone, not only will I deny it, but I will kick your everloving ass the next time I see you and tell the whole family that you're a gay ass little queer. Got it?"

I nodded. At least it sounded like he was as scared as I was of the family finding out about our sexual liaison, so I thought we were both good on that point. "Anything else?" I asked.

"That's all for now." he said. "I'll let you know if and when I want to add anything to it."

And that was it for the night. He rolled over and went to sleep. I was left there to lie in my own wet spot with my head buzzing about what had just happened. It took me a while to drift off, but I eventually did, and when we woke up the next morning we both acted like nothing ever happened. We went about and did all the things we usually did, like going to the mall, visiting the music shops, hanging out at the corner store, drinking cokes and eating candy bars.

When it was time for bed that night we both stripped down to our underwear and got into bed. We just kind of chatted about nothing in particular for a while till he was sure my parents were asleep. Then he looked over at me, pulled the covers down and stripped off his underwear. His cock was hard, and he started slapping it gently against his stomach.

"You know what I want." he said.

I was aching to suck his beautiful cock again, but I really wanted to be dressed as a girl when I did it. I wanted to be used as his little girlyslut. I decided to go for broke.

"Do you mind if I do something first?" I asked.

He looked a little puzzled. "Like what?" he said.

"Well since you didn't seem to have a problem with me sucking your cock last night I was hoping there was something else I could do to make it a little more... interesting."

"I don't know." he said looking a little nervous. "What did you have in mind?"

I laid it all out on the line for him. I told him how I loved to dress up in girl's clothes and that I had fantasized about being treated like a real girl by a man. I explained that was why I sucked his dick, because I had fantasized about being with a man for a long time. I told him that if he let me suck his cock while I was dressed, that I would do anything he asked of me. Absolutely anything. At first he wasn't quite sure about the whole thing. I think he just wanted to get his rocks off and go to sleep, but after some pleading on my part, he agreed to at least see what I looked like all dressed up.

I took my hidden stash of girly stuff out from underneath the bed and quietly slipped into the bathroom. I quickly jumped into the shower and made short work of shaving the hair off of my body. After drying off I made a hasty change into my sexiest outfit. It was a black bustier and matching panties with black fishnets. I had a couple small falsies I placed into my bustier and put on a long, curly black wig. I attempted to do the best slutty makeup look I could with my limited experience and quietly slipped back into the bedroom. Dale was starting to fall asleep when I came in, as his eyes were closed and his dick was almost completely limp. When he heard me close the door he opened his eyes and I'm pretty sure he liked what he saw as he did a double take and his cock instantly got hard. He sat up in bed and subconsciously he reached for his now erect dick and began stroking as I did a slow turnaround to let him see all my goods.

"Man, you look hot!" he said.

"Thanks." I said in my softest voice and giggled a little.

I gently crawled on the bed on all fours and gingerly took his cock from his absently stroking hand. He was so excited, he already had precum leaking from the tip. I looked him in the eyes as I softly licked it off and whetted my lips with it leaving a small streamer still attached to his now throbbing head. He moaned softly as I put it in my mouth and started stroking the shaft with both my hands. After a bit of this I was determined to get as much of his shaft into my mouth as possible. I slowly took in as much as I could till it hit the back of my throat. I let it sit there for a while as my muscles relaxed enough to allow an extra inch. I continued to do the same thing till I started gagging or needed a breath, then pulled off and started all over. With some patience I eventually got seven inches of his throbbing manhood down my gaping maw. At this point I looked up into his eyes and started fondling his balls while rotating my head around his shaft. This was all he could take as he suddenly unleashed a torrent of hot jism. With his cock halfway down my throat already I just had to relax and let the sweet spunk stream down into my belly. I pulled his cock out of my throat when it felt like he was done and proceeded to lick him till he was nice and clean then I rolled over to the side of the bed. He was still breathing hard and had his eyes closed.

"So was that Ok?" I asked.

He smiled. "Oh my fucking god yes! You looked so hot going down on me! I'm surprised I lasted as long as I did. Good thing you were going nice and slow or I would've cum after three seconds! Man I've never had a girl suck my cock like you did."

I'm sure I blushed a little when he talked about me like I was a girl. I'd never felt more feminine in all my life than I did at that point, and it felt great.

"Have you ever had girl suck your cock before?" I cooed.

"Sure. Plenty of times, but never like that. That was even better than some of the fucks I've had." He replied.

"You've fucked girls before?" I asked incredulously. I hadn't even seen a girl's real tits before, except in porno's.

"A few." he said. "You mean you haven't? Well I guess you wouldn't, looking like that." He laughed to himself a little. "No matter. I'm going to add a new condition to our agreement. You're to dress up any time I ask you to."

"But wait!" I started to complain. "You can't make me do this when anyone is around! What happens if I get caught?.

"Don't worry." he said. "I won't make you do this when we're at risk of getting caught. I don't want to be seen being blown by a guy in drag any more than you want to be outed."

The feminine feeling was starting to wear off after that last statement and reality was beginning to set in. Well at least I'd had another fantasy realized. With a little luck, I thought, maybe I could coax him to going a little further next time.

Over the next year I would dress up and blow Dale every time he came down to stay with me, or I went up to stay with him. I eventually got very good at deep throating him, and could keep all nine and a half inches of him securely down my throat until I ran out of breath or he came. I tried dropping subtle hints about wanting him to screw my brains out, but I think he was too afraid of actually putting his dick in another mans ass, however womanly it looked. Maybe he thought that it would push him over the line and he actually would become a fag, which may have been one of his greatest fears. It certainly had been one of mine, although when I was dressed as a girl I didn't feel like a man anymore, so those fears gradually starting fading away as I thought of myself more as a woman at least while I was dressed.

Spring break came and I was hoping to be able to lie low at home and do my usual loafing around my bedroom, playing games, sleeping in, dressing up and wacking off when no one was around, but when I got home from school on Friday, I discovered my parents had made plans of their own, that hadn't included me. So after a drive into the country I was unceremoniously dropped off at my aunt Lilly's house with a suitcase and a sleeping bag, while my parents drove off to enjoy their vacation. I hadn't even had time to secretly pack my stash of girly stuff so I could have some fun while I was here. Well at least I was up here with Dale, so maybe it wouldn't be so bad after all.

Normally aunt Lilly didn't mind me coming over on vacation because she would have time to plan a few things for Dale and I to do and we would pretty much entertain ourselves. This time however I think she was a little pissed at my parents for dumping me on her with little to no notice and she wasn't shy about showing it. Upon my arrival she curtly told me to drop my stuff off in Dale's room and get ready for dinner. She said Dale was out taking care of a few things on the farm and would be in shortly, then after dinner we were to get ready for bed because they were headed into the local town about 30 minutes away for a night of dancing they had planned weeks ago. I did as I was told and by the time I had washed up and came to the kitchen table Dale was already sitting and waiting for me. He gave me a halfhearted grin as I sat down, and both of us began eating in silence as neither one of us wanted to anger Lilly any more than she already was.

We were about halfway done when my aunt and uncle walked in, dressed in their dancing finery, and proceeded to tell us what was to be done after the meal. We were to clean the dishes and put them away. After that we were allowed to watch TV for no more than 2 hours till 9 o'clock then brush our teeth and go directly to bed. We both nodded in agreement and they walked out, got in their truck and disappeared down the long, dusty driveway.

Once they were gone I immediately opened up and began talking to Dale asking him questions about school and life on the farm expecting him to do the same, but he didn't. Instead he just gave me one or two word responses, never cracking a smile. I thought maybe I had pissed him off too somehow so I just shut up and finished dinner. By the time we were done eating, I was really bummed out. My last holdout for having fun was slipping away and it looked as if I was in for one long and boring spring break.

As I got up from the table to clean the dishes, I heard a knock on the door. Dale immediately got up and walked over to answer it as I went to cleaning the table and washing the dishes. Although I couldn't see anything, I could hear Dale talking to another guy at the door and immediately wondered who it was and what they were doing here. I heard the door close and turned around to see my other cousin Jay walk into the kitchen with Dale.

Jay was the son of my aunt Betty and lived not too far from Dale. He was about the same size as Dale at 6 feet and 175 pounds with brown hair and eyes, but a year older. The two of them would hang out all the time but Jay was clearly the alpha dog of the duo. When I was alone with Dale he was downright civil and even a little in awe of my city street smarts. He would ask me questions about music and computers, places to go and hang out, because there was none of that in the rural community where he lived. However when they were together and I was there on vacation they took every opportunity to torment me nonstop. They would poke fun at my slender frame and small stature and call me girly boy and things of such nature. Clearly, I feared, that was to be the case tonight.

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byNearMiss© 37 comments/ 236149 views/ 315 favorites

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