tagTranssexuals & CrossdressersBilly Is Billie on Halloween

Billy Is Billie on Halloween

byCuriousGuy4U©

It was October 30th when I first found out who I really was, a cock sucking cum drinking whore that needed to be fucked. For so long I have dreamed of women without having any luck actually being with them. With my very feminine figure and shoulder length hair I was always pushed aside for the bigger and bader guys. As they always say, nice guys finish last...

It was Monday night and I was just getting out of school, I went to the local community college, and I was standing in the cafeteria getting a cup of coffee. The girl of my dreams, Jenny Ferguson, was right behind my and I could feel my knees get weak. I had never actually spoken to Jenny, but I have made love to her many times in my head. I was just getting finished pouring my coffee when I decided that I would speak to her for the first time.

"...Hey" was all I could get out.

Jenny didn't even look at me as I stepped out of her way so that she could use the coffee machine. Bringing my chin to my chest, I didn't make it two feet away before,

"Hi there. Billy right?"

"Uh, yeah, I'm Billy" I couldn't believe she actually knew my name.

"What are you up to tonight?" she asked me.

"I was going to go home and do some homework" I thought the truth was a good answer.

"Homework?!" Jenny said with a smile. "Want to go have a little fun instead?".

"What kind of fun?" I asked, not knowing much about the subject.

"Well I am going to a costume party and I don't have anyone to go with. It's in a couple hours and I know you think I'm hot so what do ya say?" she said with he eyes glowing.

My mind started to go into hyper speed. I have never been to a Halloween costume party and certainly have never been asked by the hottest girl in the world. I wouldn't even know what to do, who to talk to, or what to say. But I couldn't just let this go to waste; maybe she is one of those weird girls that loves nerdy guys. I decided that I could not pass up the opportunity and that I was going to this party.

"I'd love to accompany you to the party Jenny" I said with a bright red face.

"Great! We are going to have so much fun tonight!" Jenny seemed so excited to have me going to this party. It made me feel like I was the only guy on earth. "Follow me to my car, we need to hurry or we will be late". And off we went to her car, a hot pink BMW, like nothing I have seen before. As we got into the car I could see that she kept everything nice and clean except for a few pairs of panties and bras in the back seat. My eyes kept diverting back to see them all. I wasn't sure if every girl had underwear in the back seats of their cars or if Jenny just changed a lot according to her moods.

"You like those do you?" Jenny said, noticing that I couldn't stop looking at all of her gorgeous lace and leather.

"Huh?" my head quickly turning and my eyes looking right into hers.

"I said do you like my panties...?" she said interrogatingly.

"I guess so, they look nice"

"Well good" she smiled and started the car "maybe you'll get to see more later, if you're good..." she then winked at me as we drove off.

I had no idea what to say. 'Is she going to show me her smoking body?' 'Am I going to get lucky tonight?' My dick started to get really hard and could have reached its maximum 4" if I didn't cut it off by squeezing my legs together.

I didn't say much as we drove to Jenny's apartment, just a few things about the music she was playing, mostly I just couldn't stop thinking about how great the night was going to be. Before I knew it we had pulled into a parking lot and Jenny stepped out of the car. I mirrored her every move as she walked up to her front door not speaking a word or acknowledging that I was even still there. As she walked into her place she left the door open behind her, leaving me the invite to come in whenever I was ready. As I stepped into the apartment Jenny quickly turned a corner and disappeared. I was alone.

Looking around the apartment I saw a lot of contemporary art and furnishings, nothing looked cheap. I couldn't understand why Jenny was going to a community college if she was loaded with cash. There were also a lot of mirrors, one above the fireplace, along the entryway, in the kitchen, and even one above the couch in the center of the room. Unlike other apartments I have seen, this one was very big with many places for people to go. After a couple minutes just wandering around the living room I heard Jenny yell from somewhere,

"Billy, go ahead and poor yourself a drink, I have vodka in the freezer"

"Oh, ok" I said, knowing that I never drink.

I didn't want to disappoint Jenny so I walked into the kitchen and opened up the freezer. She wasn't kidding, not only was there vodka but every other kind of alcohol you could think of. I grabbed the bottle of Gray Goose and found myself a couple shot glasses hanging on a rack by the freezer. Pouring myself a drink I thought to myself, 'here goes nothing' and took the shot. It wasn't bad, actually it felt a little weird for a few seconds afterwards, but I never drink so what would I know about it. In fact I thought that one drink wasn't anything so I poured myself another and shot that too.

"Good eh?" Jenny said as she stood behind me.

I turned to look at her and almost blew a load. There Jenny was standing two feet away in only a hot pink lace bra and panties. She had the perfect figure, a true gift from God.

"Makes my mouth feel funny" is all I could say as my eyes almost popped out of my head from her awesome tits.

"Don't worry, that funny feeling feels great after a while" Jenny said as she walked over to the stereo and turned on some music. As it started to play, Jenny started dancing to the beat. I was stunned, I would have never thought that I would be standing in Jenny's apartment and she would be dancing for me almost naked. What happened next was even more exciting. She moved around the room dancing until she ran into me at which point she started grinding on me, rubber her soft skin all over my body. I didn't know what to do so I just stood there as my eyes rolled into the back of my head, I was in ecstasy.

After what seemed like a lifetime Jenny grabbed my hand and lead me into what I assumed was her bedroom. It was a lot quieter in the bedroom and Jenny had stopped dancing to the music.

"Ok Billy, it's time to get into our costumes" Jenny said

"Costumes?" I asked "I didn't bring a costume..."

"Its ok, we will figure something out for you to wear. It's not a costume party without a costume." Jenny said to me assuringly.

"Alright, what ever you want" I said just trying to make her happy

"That's what I like to hear Billy. We are going to have so much fun tonight" Jenny said excitingly as she opened up her closet and walked inside.

I stayed outside the closet as she fumbled around with a few different ideas. After looking in a few different sections of her huge closet Jenny finally came out with a very sexy schoolgirl's outfit. My heart pounded as I imagined Jenny in the short checkered skirt and pure white blouse. She went back into the closet and quickly returned with a black lace bra, panties, stockings and a pair of 3" heals.

"You will look beautiful in that Jenny" I said knowing that girls love to hear that they look good.

"Thanks Billy, now to find you something..." Jenny said as she walked back into the closet.

I thought to myself again 'find me something? What could she find for me in there?'

I found out soon enough as Jenny walked back into the bedroom with a very similar schoolgirl's outfit just with a red checkered skirt instead of black. Instead of laying the items on the bed she walked straight to me and put them up to my thin body.

"That should work, you will look so hot in this" Jenny said in such a sexy voice.

"What?!" I backed up quickly from Jenny not realizing that she really wanted me to wear girl's clothes.

Jenny seemed hurt "I thought you wanted to have fun with me tonight Billy... Please don't hurt my feelings."

"I do, but I didn't know you meant like this."

"Well it is a costume party Billy, and this is all I have for you. If you want to leave and go do your homework I guess that is up to you. But without a costume you cannot stay here." Jenny said as she stood there looking at me pleading with her eyes.

"You don't have anything else I could wear that isn't for girls?" I begged.

"No, this is it. Nothing else I have will fit you, this is just your size"

I stood still, not knowing what to do. On one hand I wanted to run out of the apartment and never look back, but on the other hand I wanted to see Jenny in her black lace stockings and see what she might do with me later on in the evening.

"Ok Jenny, I will do it." I gave into her wishes.

"Very good then, we are going to have to get you prepared" Jenny said as she quickly grabbed my hand and pulled me into the master bathroom.

Without warning Jenny started to unbutton my shirt. I didn't try to stop her until she started unbuttoning my pants.

"What?" Jenny seemed confused. "We need to get you cleaned up and we don't have a lot of time so just relax a little bit."

I let Jenny do what she wanted as she completely undressed me. As my pants fell to the floor I knew that she could see my small pecker and just hoped that was what she wanted. She stepped over to the shower and turned it on, checking the water to make sure that it was not too hot. Then she grabbed a bottle and put it in my hands.

"Use this to get all of the hair off your body from your face down. We can't have all that stuff sticking out in the outfit you're wearing" Jenny said firmly as she walked back into the bedroom, leaving me alone.

I stood still for a moment, wandering what I had got myself into. It didn't last long though as I felt a sense of bravado to do whatever I needed to please Jenny. I stepped into the shower and used, what I believe to be, Nair to remove all of the hair from my body. Washing myself clean I felt so soft and so smooth. Besides not having tits, my body looked like any of the girls I had seen in school. After finishing up and drying off I made my way out of the bathroom and back into the bedroom to find Jenny waiting on me.

"Loose the robe. Let me see what I've got to work with" Jenny said as if she was an artist beginning a new piece of work.

As I let the robe fall from my hairless body I could feel the air brush past me like soft breath from a warm mouth. This new feeling was invigorating and I felt incredibly sexy at that moment. Then I realized what was about to happen, Jenny was going to make me wear women's clothes. Not just any clothes though, an outfit suitable for a sexy schoolgirl. My thoughts turned to panic again, knowing that dressing this way could not lead to anything good, but I couldn't shake the thought of what Jenny might let me do to her later on.

"Start by putting these on" Jenny said as she handed me a red laced thong and bra. I did as I was told, sliding the soft fabric up my legs and then letting it strap against my thigh. My stomach started to turn as I could feel my cock harden. Feeling the thong start to ride up my ass and the way the fabric moved against my cock was amazing. After the thong came the red bra, with more room in the cups than I needed. Little did I know that Jenny had two C-cup breast forms for me to place inside, giving me a nice and soft rack that any girl would be proud of.

"Now we can slip on your blouse and gorgeous checkered skirt" Jenny smiled, I could tell she was enjoying this immensely.

I no longer hesitated, quickly trying to get the skirt on to cover my small erect penis. Everything felt so soft and sexy on my body. While keeping my ass nice and warm, the skirt let any small breeze violate my entire genital region.

"Ok, now lets get these stockings on those long legs!" Jenny seemed to grow more excited with every piece of clothing we added. Although I was getting just as excited, I kept my mouth shut and just enjoyed the experience of pleasing Jenny. She helped me as I put the lace stalkings on one by one, making sure the get an even stretch and covering everything just above my knees. After we finished I felt like a real woman and wanted to see just what I looked like. But before I could get to a mirror I was stopped by Jenny saying, "Not yet hun, first we need to get some makeup on that pretty face of yours."

Once again, her word was my command as I followed her to her makeup station in the corner of the room. Jenny had the mirror covered up, but she had me facing her the entire time anyway. While she applied bright red lipstick and a variety of eye shadows and blush, Jenny had a very focused and determined look on her face. She almost seemed like she had stopped having fun and started acting like this was her duty, her mission. It didn't take long for Jenny to apply the makeup to my face. I am not one to struggle, so I made the perfect canvas for her to work on.

"All we have left to do is fix that hair and you will be set for the party". Jenny assured me, not knowing how much I was really enjoying this. I would let her do this to me every day if I knew that she would be completely focused on me and touching my body wherever and whenever. And the hair may have been the best part. Running her fingers through my hair and getting it to do exactly what she wanted, I was in heaven. But every good thing comes to a conclusion. She had sprayed a mixture of formulas into my hair before she was completely satisfied. I now felt and smelled just like a sexy schoolgirl ready to party and have wild lesbian sex with Jenny.

"Are we done?" I asked cautiously.

"Yup, time to check you out!" Jenny's voice made me feel confident.

As I made my way to the full sized mirror on the wall I couldn't even recognize myself. My features along with Jenny's breast forms and makeup made me look like one of the hottest girls in school. I looked like the girls that I dream about every night. Standing next to one another, Jenny and I could have been in any of the hottest magazines with guys eyeing us and jerking off all over our pictures.

"The others should start arriving soon, lets go grab a drink and start the night off right." Jenny said as she gave a cute little skip and headed back towards the kitchen. As I followed I could not help myself, loving the way these new cloths felt against my smoking body. I could still feel the alcohol in my veins as I thought about taking another shot of the chilled Vodka. Not surprised, Jenny had already poured two shots for us.

"Here's ta two super hot girls having a great time tonight" Jenny gave the toast as we slammed down our shots. Just as soon as they were down Jenny had two more glasses filled up for another shot.

"Here's ta two smoking hotties showing off their bodacious asses tonight!" Jenny shouted as she gave me a slap on my ass, almost causing me to spit up my vodka. And as I put down my glass I just found Jenny pouring yet another shot, making this the third one in under two minutes.

"And finally here is ta two sexy bitches having the hottest sex of their life tonight!!" Jenny screamed and then took down her shot and giving me a huge wink. The thing I guess she didn't know is that she would have to get me drunk at all to get me in her bed.

Suddenly there was a knock on the door and voices coming from outside of the apartment. It sounded like a couple guys that have already had enough to drink. As Jenny's face lit up and she started walking to the door she turned to me and gave me my last instructions for the night.

"Just let me do all of the talking. We don't want these guys thinking that you are gay otherwise they will hurt you very bad. Just keep quiet and look sexy and you will have a great time."

As she opened the door I could see that there were not only a couple guys, but six of them all together. They were all dressed up in costumes, like us, but they weren't too original. Every one of them had jeans and a football jersey on, with a little bit of face paint like the football players on TV wear. It looked like their entire costume took about 5 minutes to put together and the jerseys were all from the same team, but I couldn't tell you which one.

As they walked in I kept my mouth shut and stood lifeless, not knowing what to make of all this. Jenny gave a hug and kiss on the cheek to every one of the guys as they walked through the door. One by one they passed me through the kitchen to put away their beer, some of them giving me a smile or a wink as they walked around me.

It seemed like forever as the guys got settled in. Some went and turned on the TV and the others started pouring drinks for everyone. After a couple minutes everyone ended up back in the kitchen. One of the Guys, who I found out was named Kyle, had a line of tequila shots set up for eight people. I was feeling pretty buzzed by now and didn't really know what to make of anything right now. I just wanted some of the other girls to show up and take some of the attention off of me. As the shots were passed around to everyone, including myself, Jenny proposed a toast.

"Everyone, this is Billie, she is the guest of honor this Halloween and may it be the best Halloween of her life" Jenny raised her glass and gave me the sexiest, yet most evil, smile I have seen in my entire life.

"Here! Here!" The guys yelled as they all pounded their shots in unison.

"Lets go start the movie" A guy everyone called Hawk said.

"Sounds good, everything is ready to go" Jenny replied as everyone started making their way into the living room where two large couches were set up around a television. Still unsure of what to do, I stood still waiting for guidance. Jenny noticed this and quickly helped me move over to one of the couches and sat me down right in the center seat. I could already feel my body melting into the sofa while six shots of hard alcohol rushed through my lightweight body. Two guys sat down on both sides of me, I could see that is was Kyle and Hawk, the only two guys that I really knew the names of.

As the movie began I knew it wasn't a feature film. I watch a lot of movies and this wasn't even rated. From a black screen we first saw a girl dressed as a schoolgirl, surprisingly almost exactly like Jenny and I. She walked down the halls of her school alone until she ran into three boys who she didn't look surprised to see. Before I knew it the movie went from four people talking to soft-core sex. My mind raced with excitement thinking about how great it would be to have a girl in the halls of my own school. But just as I was thinking of this I could feel a hand slide across my chest and start rubbing my fake nipples.

"Huh...?" Was all I could get out as I turned my head sharply to look at Jenny for advice. But instead of getting any help with the situation I found Jenny staring at me with a smile and three guys fondling her perfect body. As she gave me the wink that I was starting to get to know too well, Jenny said to the guys next to me,

"Be gentle boys, she isn't as durable as I am"

My confusion turned to shock as Hawk started kissing my neck and grabbing my thigh. But I didn't fight; it actually started to turn me on. Lucky for me these guys would not notice my hard-on because of its small size, but I needed to make sure that they did not find out that I was really a guy; the last thing I need is to get killed on Halloween night.

"We're gonna have a lot of fun tonight hot stuff" Kyle whispered into my ear. Just then my face was turned and Kyle started to kiss me on the lips. I didn't even try to stop him as his tongue slowly slipped into my mouth and started massaging mine. As I closed my eyes I really felt like a girl. Having two guys do what they wanted to me and just enjoying the experience.

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byCuriousGuy4U© 7 comments/ 160321 views/ 51 favorites

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