Playing the Part

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story.

***

My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let me back up and tell you the story.

It was my last summer break before college and I was taking full advantage of it. My friends and I went to all the popular nerd events and during the last one, a comic convention, my life was changed forever. Unlike the rest of my overweight friends I was pretty small. Five foot, three inches, and barely one hundred and fifteen pounds of scrawny little man. I kept my brunette hair long, since I liked the way it looked and a girl in had once told me it looked good. My eyes were a deep shade of green and I was a bit on the pale side with light pink lips and nipples.

The comic con we were going to was a Sci-Fi one and I was going as a certain space princess since I had both a small body and the hair to do it. We were three hundred miles away from my home town which give me the courage to do it since I knew no one I knew would be there. The morning before the convention my friend Mandy, who was a pretty big girl with fire red hair and huge 44DD breasts helped me do my makeup and hair in a long pony tail like the princes had worn when she was in the infamous gold bikini. We had made the bikini and it was really skimpy. Skimpy enough that I was a bit nervous when I put it on the first time back home.

The top was a 3D printed plastic that I painted gold then lined with green felt so that it looked just like her metal top. The bottom I had Mandy do out of actual metal since she was an amateur black smith and it had to be one piece. Being fair it was actually incredibly well done. It matched my pelvic area perfectly which was sort of the idea only it left very little to the imagination and required me to shave my entire body. The fabric barely covered my little dick and the sides of my ass were showing at all times. I was worried that if any one stepped on the fabric either the top of my dick or my ass crack would show.

I wasn't normally a cross dress or crossplayer as it's said, but everyone wanted to do the franchise and our only three girl friends were just too big to play the part. I was perfect for it and the girl's wanted me to do it way more than the guys did. It's not that big of a deal I was told and to be honest I had always wondered what I would look like as a girl. Now I was 18 and free so why not give it a shot I thought.

After I was dressed, I was looking at myself in the mirror and pretty proud of how I looked. I fit the part and unless I bent over no one could see my red thong or the tape I was using to hide my small dick and keep my balls pulled up tightly inside myself. Even my small dick would show in this costume if I didn't hide it securely. I gave myself one last look then grab my three-inch heel mid-calf boots and put them on. I had practiced walking in these for weeks and felt pretty damn good about myself as I left the hotel.

Waiting in line I was getting my ass checked out often and it was a pretty big confidence booster for me. Mandy and the others noticed it and when no one was around I was called a slut playfully from the girls. Nope I'm still a sweet little virgin I said.

Which way Mandy asked?

All ways I said. I haven't even kissed a girl yet I told her.

Oh, wow Samantha said.

I laughed and said yep completely pathetic.

***

The convention was a blast and my original fear of being called a homo or something faded fast as I walked around being asked to take pictures with people. Most had no idea I was a guy and the ones that did were cool with it. I even got a chance to take a few pictures with the official team for the modern movies, which for a Sci-Fi nerd like myself was a pretty big deal. The only thing that upset was at the end when I ran into Randy my bully. I had no idea he was a closet Sci-Fi fan but he was there and seemed to be enjoying himself. I avoided him in fear he would recognize me and start in on the taunting then left a little earlier than the rest of my friends. The man was brutal to me and seeing me like this would put him into overdrive. I had a restraining order against him but I wasn't sure if it was valid in this state.

When I got up to my hotel room, I ordered pizza and waited for it to arrive. I kept the costume on and had a plan to thoroughly jerk my little cock while in costume after I ate. A knock came on my door and when I opened it, I said wow you guys are fast. Instead of a pizza delivery person I cam face to face with my bully Randy.

I fucking knew it was you Randy said with a smile and pushed me back into the room. He shut the door and said so what are you a sissy faggot now?

Randy get the fuck out of my room before I call the cops on you again, I said.

He got mad and before I could even think he took two steps and punched me in the stomach. I folded like a cheap table and fell onto my ass holding my stomach. All I could do was roll on my side and fight to breathe again. Randy leaned down and said into my ear I did a god damn month in jail because of you, faggot. I couldn't graduate and my scholarship has been pulled because of you Randy growled into my ear again.

Randy stood back up then said it wasn't all bad though. I learned that I loved breaking little sissy faggots like you, then turning them out he said. I watched as he began undoing his belt then pulled his pants and underwear to the floor. His six-inch cock was hard and he said see what you did to me? You are going to take responsibility for this Randy said with a crooked grin on his face.

Randy I'm not gay I said.

Yes, you are faggot Randy said. You just don't know it yet. Now get the fuck up and suck my cock sissy he said getting mad again.

I got on my knees then just froze. Randy I can't I said and began crying.

Tommy oops, I mean Tammy you are going to suck my cock Randy said. That's going to happen and you just need to make peace with it. The only thing you get to decide, is how many times I'm going to beat the shit out of you before you suck it randy said.

I looked at the clock between the beds in my room. It was 4:30 PM. The convention wasn't over for another three hours and then my friends would go to the Q and A which would take a few more hours. In one punch he put me on my ass and I don't know if I could take another hit let alone make it through six hours or more of him beating me.

Randy if I do this will you leave me alone, I asked?

Sure, Randy said.

I got closer to Randy's hard cock and resigned myself to my fate. I've never done anything with anyone so my first sexual experience is about to be with man dressed as a woman. Get to it faggot Randy said. Okay I can do this I thought. Just do what you saw in the porn movies you jerk off to and it will be over fast I thought. I reached out my hand and gripped the hard shaft of his cock. He wasn't much bigger than me so it wouldn't be too hard I thought. I stroked my hand up and down his shaft noticing that his skin felt really smooth and soft. Randy grabbed the back of my head and said suck it faggot, then shoved my face onto his cock.

Okay, I said then then opened my mouth as wide as it would go. I felt him pull on my head and I directed the head of his cock into my mouth. I instantly tasted the precum and sweat on the head of his cock and fought the urge to gag. No, he will get mad and hit me again I thought. I have to do this right I thought and began trying to remember what I had saw all of those women doing.

I started stroking the shaft and caressing his large balls while moving my mouth back and forth on his cock. Randy moaned out and I knew I was on the right track. I got a bit daring and tried to get more of his cock into my mouth and felt my gag reflex kick in. Relax your throat faggot Randy barked. I tired but I couldn't get it to relax. Randy grew impatient and said I'll do it for you sissy then forced his cock into my throat. My gag reflex went nuts and kept trying to expel his cock from my throat.

Ignore it, ignore it, ignore it, I said to myself until finally my throat stopped fighting it.

That's it faggot, Randy said then began pumping his cock in and out of my mouth. He started going faster and faster saying that's a good little sissy slut. Take my cock just like that bitch. It actually wasn't as bad as I thought it would be. Yes, I was tasting his cock but it was better than being beaten up I thought. Soon he will cum and then leave my room. I was looking forward to this being over when someone knocked on my door.

You expecting company faggot Randy asked and pulled his cock out of my mouth.

It's probably the pizza delivery I said.

He smiled and pulled his pants up. A blow job and dinner? What a good little sissy house wife you are Tammy he said and went to the door. How much do I owe you he asked the woman?

You already paid over the phone the woman said.

Oh, in that case let me sign the tip Randy said. He signed the check then said bye sweet cheeks.

Sir that's sexist the women said.

And you're a fat whore Randy said and slammed the door.

Randy sat the pizza down on the table then said, where were we? Oh yeah you were milking my cock like a good sissy. He came back to me still kneeling and pulled his cock back out. Dinner time faggot he said then grabbed the back of my head. I opened my mouth already determined to do this and get him the fuck out of my room.

He was already close and it only took a few more minutes of him fucking my mouth to finish. Fuck I'm gonna cum he said then rammed my head down on his cock and began spraying his seed down my throat. I began to panic when he didn't let me go for a bit and I was running out of air. I slapped his thighs and he said of fuck I forgot and pulled his cock back giving me the last squirt of his cum right onto my tongue. It was slightly sweet and salty with a weird flavor but I didn't hate it I thought. Show me what's in your mouth he demanded? When I did, he said good slut now swallow it. After that I was told to clean his cock and I knew he meant to lick it clean. He seemed pleased after a bit and said okay enough slut.

I expected him to leave but instead he sat down and opened the box of pizza. Randy you said you were leaving after sucked your dick I said.

I will, but I get hungry every time I get my cock sucked and I don't have the cash for food Randy said.

Okay I said then got up and sat on my bed.

Got anything to drink Randy asked?

In the fridge I said.

Randy grabbed a soda and popped the lid. You know you will make a damn good sissy wife someday Randy said. He took a bite of the pizza and said if I would have known you were this good at sucking cock, I would have been pounding your ass in a different way. He laughed at his own stupid joke while I just sat there. He ate the rest of my pizza then got up. Well that hit the spot now get over here and give me a big kiss goodbye he said.

Fuck why do I have to do this I thought but did what he said. Randy was a good six inches taller and I had to tip my head up to kiss him. I closed my eyes and thought get it over with and get the fuck out. Randy grabbed me and pulled me tight then reached his head down to mine and began kissing me. I felt his tongue go into my mouth and I closed my eyes tighter. Just dealt with it I told myself. When he grabbed my ass, my eyes sprung open. Oh god he's not going to do that is he?

You got a nice firm little ass here Randy said squeezing both of my cheeks then pulling them apart.

Randy you said just the blowjob then you would leave I said.

It's your fault for looking so damn sexy Randy said and then tossed me on the bed.

I tried to get up but was rolled over fast and he climbed on top of me. Randy I'm going to start screaming if you don't get out of here right now, I said.

His hand went over my mouth and he easily pushed me further onto the bed then spread my legs. He was our schools star wrestling champ and I knew I had no chance at stopping him. He wasn't just much bigger than me, he knew how to wrestle and had a scholarship to college to prove it. You didn't really think I was going to leave here before I took that black cherry of yours did you Randy asked? Now be a good little sissy and keep quiet and I'll spit on the head for you he said.

He pulled his hand from my mouth and I said lotion. There's lotion on the stand please use it I said almost begging for it.

Well since you asked so nice Randy said. He got off of me and for a second and I thought about running for the door. I was still in my heels and he was so damn tall I would never make it I thought. He pulled his pants off then grabbed the lotion and began stroking his cock until it got hard again. Ready bitch he said getting on top of me again.

No, I said and began crying. Randy please don't do this. If you stop and leave, I won't tell anyone what you did to me I said. I'll take it to my grave I swear.

You're not telling anyone anything Randy growled. You're my bitch now, and you will do exactly what I tell you to do from now on. When we get back home, I'm putting your ass out on main street to make me some money while I live in your house and fuck your mom he said. That pussy dad of yours is moving out too he said then lined his cock up with my ass and shoved it in roughly. My thong didn't help me in the least bit and was easily pushed aside.

Ahh I yelled out and he pulled a pillow to my face.

Bite it Randy demanded. Become a proper pillow biting sissy slut right now he demanded. I bit the pillow and he rammed more of his cock into me then pulled out and did it again forcing the entire thing into my no longer virgin ass. Oh, this is a nice tight boy pussy you got here. I bet it will fetch a pretty penny out there while I fuck your mom Randy said then just started fucking me like I was his hot girlfriend.

I was grunting and squealing into the pillow while he fucked my ass as hard as he could. It hurt really bad at first then my ass began to relax and it started feeling good. My cock got hard and as he kept ramming me it was being teased and caressed by the soft blankets under me. Stop Randy I moaned out. Stop your going to make me cum I said again. Please Randy I don't want to cum I pleaded.

Just fucking take it sissy Randy grunted. He kept pounding me for another minute then said he was about to cum.

No please stop Randy I don't want this I said. It was no use and he began flooding me with his thick warm seed. I knew that would be the tipping point for me and I couldn't help but cum myself and bit down on the pillow hard refusing to let him know he made me do this.

When he was done cumming he slammed his cock back into me one last time and got up. I was crying again and I heard Mandy say what the fuck are you doing Randy?

I turned and saw Mandy and a few of my other friends standing in the door. He fucking raped me I said still crying.

You mother fucker I heard Matt my rather big six foot three hundred pound friend say.

What are you going to do fat boy Randy asked? Matt tackled him and my other friends including Mandy began beating the shit out of him. The big bad bully Randy was screaming for help pretty quick not able to handle five large people kicking his ass at once. Security got called and when they got there Mandy covered me up with a blanket.

An hour later Randy was in hand cuffs and I had to explain it all to the cops and have my mom email over a copy of the restraining order. I spoke to the manager of the hotel in the hall way who was seriously scared I was going to sue since Randy wasn't even staying here yet got right in with no problem.

An older detective came up and said I'm sorry I have to do this but he said that you two are lovers and that you enjoyed this type of thing. He said that you even ejaculated on the blanket while he was doing it the detective said.

I began crying and Mandy said we all walked in as Tommy was begging him to stop and not do this to him. But if you don't believe me check the blankets for yourself Mandy said.

A forensic team collected the blankets and said even if you had an orgasm it doesn't mean he didn't rape you. It's an involuntary reaction and not your fault Ma'am. He took down my statement then said he was sorry that this happened to me. He's going to prison for a very long time and by the way he keeps calling you a faggot he might just go to federal prison for a hate crime the detective said then excused himself.

After everyone left Mandy crawled into bed and held me. Tommy I am so sorry this happened to you. We will never ask you to dress like that again.

Mandy they are going to find my semen on that blanket I said.

No, they aren't Mandy said.

Yes, they are I said. I couldn't help it I said. It just felt so good and before I knew it, I was cumming I said and began crying.

No, they aren't Tommy Mandy said. Before they got here, I felt the wet spot and knew what had happened so I switched the blankets out with the ones in the closet while you talked to the hotel manager in the hall Mandy said. The only thing they are going to find is his semen and your blood from when you sat down, she told me.

Thank you I said.

***

I spent the next week in my room depressed and confused. My overly liberal parents kept trying to get me to confess I was transgender but I just wasn't ready to face that yet. One morning my mom came into my room and sat on my bed.

Sweety you need to get up and out of this room Mom said.

Mom I'm not ready to face the world yet I said.

Sweety there will never be a good time to face the world after something like that happens Mom said. But the longer you wait the harder it is.

Mom I liked it I said and began crying. Why did I like being raped I asked and the tears just flowed?

Oh, sweety Mom said and began holding me. Sweety you didn't like being raped Mom told me when I calmed down a bit.

Mom I came harder than I ever have in my life I said.

Sweety that's because a man was fucking you Mom said. You don't enjoy being raped you enjoy being fucked by men Mom said.

I just stared at her for a minute. In all of my 18 years on this earth I have never once heard my Mom curse, but she just said fuck twice in less than a minute. Mom I said.

You think I don't know what it's like to get fucked by a man Mom asked? Your Dad has fucked me at least once a day for the last twenty years and I love it every damn time Mom said.

Language I said.

Tommy you aren't a kid anymore Mom said. Time to face the fact that your Mom not only says fuck but gets fucked all the damn time. Sometimes by men other than your dad while your dad records it Mom said.

If I get out of bed will you please stop talking about your sex life, and never say the word fuck around me ever again I asked thoroughly grossed out?

Deal Mom said.

***

An hour later I was shopping for new clothes with my Mom. She insisted she come along and help me find clothes that fit right. I was embarrassed and scared but everyone was really nice to me. They got me all the things I needed and some I didn't like bra's for breasts I didn't have yet but my mom said she would gladly pay for. For now, I got breasts forms. After we got clothes, she said girl's day and took me to the salon, then a nail parlor for a many petti, then to a high end makeup store to get and learn how to put makeup on correctly. The last one was a huge surprise as I had no idea what women went through for something, I used to think was so simple.

When we got home, I was dressed up like a woman in a cute flower print sundress and had a 30C cup bra on filled with breast forms. My dad saw me and said hi baby girl and kissed my forehead. Glad to see you out of bed.