Category: Transsexuals & Crossdressers Stories

A Sissy's New Daddy Ch. 06

by sissyneko©

A loud crack of thunder broke the silence and Billie smiled in his bunk. Lights had been out for almost an hour and he couldn't sleep. The prison had gotten a new influx of prisoners. The first night was always the hardest and it was hard on Billie too, he could never sleep listening to the crying. Plus Billie had gotten a new cellmate in the process, a cellmate that Billie recognized. It had been a couple of years, But Billie recognized Randle the second he had seen him across the common room. Randle hadn't said anything to Billie, so there was a chance that he didn't recognize him.

As thunder echoed though the prison drowning out the cries of terrified and lost souls Billie was just about to slip into a restful sleep when he heard a quiet voice below him, "Hey Billie, Is it true that you gave Coach Conners a blow job. After you killed that guy Coach quit, Principle Blackthorn quit. Everyone was saying that you got caught sucking Coach and that he bribed her not to say anything is that true."

"Does it matter?" Billie asked back to the disembodied voice from the lower bunk. "How about this, you tell me why you're here and I will tell you about Conners and Blackthorn, and I promise it was a lot more than a simple blowjob."

"My story sucks, I got busted stealing baby food. My kid needed some formula and I had just lost my job I had another one but I wasn't going to get paid for two weeks. Food stamps wouldn't help me out so you know I did what I had to do."

Randle was stopped talking his story cut short by a nightstick slamming into the small cells heavy bars. Billie didn't know if he was going to keep going but he didn't start again so Billie honored his deal and started his story.


School was always my safe haven, I could spend all weekend in nothing but a pair of thong panties and covered in a thick layer of sticky cum, but come Monday morning I would shower, dress and head into school. I even dressed like a boy, at least on the outside. It all started with Coach Conners on a Monday morning, I had somehow managed to get Gym class for first period of the day.

Every day was the same I showed up to class slipped through the locker room and changed in a bathroom stall. At that point my panty collection was pretty massive and I was wearing sexy little silky panties to school every day. The problem was they would get all sweaty and gross after gym. So I changed more than just me pants and shirt. I had bought a few pairs of white cotton panties to wear during gym class. So every morning I would strip naked and get dressed for Gym. You can't just strip naked in a bathroom stall, so I was always early for class or the last one out.

About a week after Christmas break I was changing when I heard someone bang on the stall door. I started to panic and then I realized it was Mike. He hadn't bothered me since the night I was a party favor at his house (ed - See chapter 3) we had seen each other at school, but he was too afraid of people finding out what had happened between us. "Come on Faggot open the door everyone is gone."

I hesitated but not for long, I was pretty sure he didn't want to fuck me in the locker room. I figured worse case I would suck him off and head on to homeroom. I had slipped my stockings back on and had my panties in my hand when I unlocked the door. It had been a rough weekend so I was wearing a pair of orange satin boyshorts. Mike had a stupid grin on his face when he pushed the door open and stepped into the stall. It wasn't a handcapped stall so there was barely enough room for the two of us. It took me almost a minute but I was able to struggle into my boy shorts. When I turned around to grab my pants Mike took the opportunity to bend me over. I tried to talk but he clamped a hand over my mouth. Mike shoved his free hand down the back of my panties and tried to finger my boipussy. I never got used at school so I got out of the habit of being lubed during the week.

"What the hell, daddy said you sissy's are always ready for cock." Mike grumbled as he smacked my ass. Pushing his way out of the stall Mike called out to me "Come on Faggot don't bother getting dressed. I got some lube you can use."

I was reluctant to leave the stall but wanted this to be over quickly. Taking my time I moved into the locker area and found Mike looking through one of the larger lookers assigned to the football team. "You know ever since I showed Mandy your video, that little bitch knows I can replace her in a heartbeat she will do anything I say."

He pulled out a bottle of lube and tossed it to me. "Listen I need a letter and you're going to get it for me. I told Coach he could have you for an afternoon and he said he would get me a letter to state."

"I am not a toy for you to pass around, I don't know if you noticed." Before I could finish my angry rant, Mike grabbed me and slammed me into the lockers. He held my throat with one hand and gave me a vicious wedgie with the other.

"Listen to me you little cock puppet. I need that letter So spread your legs, open your mouth, hell bark like a slutty little puppy if you have to. I don't care but get it done." Mike said as he released my throat and let me collapse to the ground. "Shit my dad was right you do need to be put down."

Hearing him say that didn't mean anything to me at the time, though it did later when I realized his dad was a cop. Getting up from the ground I took a half second to dig my panties from the crack of my ass and then grabbed the bottle of lube I had dropped. I slipped my panties down and used two fingers to get my boipussy ready for a pounding. I pulled my panties back up and handed the bottle back to Mike, "Ok then where is Coach."

"He is in his office. Knock three times and then head in. Tell him Mike sent you and that you are his as long as he likes." Mike put the lube back in the locker and closed it up. "Also tell coach I want the letter by the end of the week."

I stood there and waited for Mike to leave, I didn't want to whore myself out in front of him. I waited for the heavy thud of the door closing before I started towards coach's office. I could hear a game film playing, he watched them incessantly. I knocked three times and heard him bark out that I could enter. I opened the door and quietly closed it behind me. He didn't turn around so I just stood there for a moment watching him. He was fit, twenty years ago. Now he was bulging in all the wrong places.

After standing there for three plays he finally turned to see who had entered to waste his time. Coach's body tensed when he saw me standing there in just panties and stockings. I was just about to speak when Coach started to sputter and mumble, "Look young man this is not appropriate you are going to need to leave her right now and I will not say anything to anyone."

"Mike sent me." As soon as I said it Coaches whole demeanor changed. He paused the game film that he was watching and motioned for me to come over to him. As soon as I was within arm reach he pulled me onto his lap. His hands immediately poured into the front and the back of my panties. He shoved three fingers in my boipussy and started to move them around I moaned and he laughed at me.

"So here is the deal, my little sissy bitch, that letter is due Friday. So if Mike wants the letter I get you till then. Any questions?" I didn't have a choice so I nodded my head yes and Coach pushed me off his lap. He pulled his cock out and pointed at my ass and then his cock.

I considered peeling my panties off, but the satin always sent me over the edge when I had a cock buried deep inside me. I pulled my panties aside and my cheeks apart as I slowly and in one smooth motion impaled myself on Coach's cock. Once it was completely inserted I did a little spin with my hips that sent coach over the edge and he shot his load. I bounced up and down twice milking his cock for some more cum, but Coach pushed me off and reached into his desk pulling out a towel. "I can do that for you sir."

"Coach, call me Coach." He said as he tossed me the rag. I put it aside and took his cock into my mouth sucking it clean. I could feel his cock starting to stir again and so did coach, he pushed me away and quickly stood up stuffing his cock back into his white cotton briefs. "Alright slut get under that desk and wait for me there I will be back in about an hour."

My throat seized up and I panicked a little, school was my escape, I could let coach fuck me each morning if I got to go back to class and spend the rest of my day as a normal kid. "I need to get my clothes I need to go to class."

Coach looked at me and then returned to his desk. He pulled a pair of handcuffs out, he looked at them and then at me again. Shaking his head he tossed them back in his desk "Here is the deal sissy, when I get back from my next class if you aren't under that desk, positively salivating at the idea of me shoving my cock down your throat then not only does Mike not get his letter, but I call the school and tell them that I had to bench him for steroid use. Do you want to destroy your boyfriends career?"

"He isn't my boyfriend, but I will do what you say." I was only a few feet from the desk so I didn't bother getting up, I simply crawled under the desk. I listened as all the other kids filed out of the locker room after changing for second period gym. I peeked out from the desk and watched the clock. After 10 minutes passed and I didn't hear anything I bolted across the locker room. I opened the stall and let out a sigh of relief when I saw my bag and clothes sitting there. I grabbed them up and started back to Coaches office. I didn't want to waste any time in the open. I was almost back to coaches office when I heard a phone ring. "Mom seriously I am at school."

It was Marcus Latrell, everyone knew , Marcus. He was taller than most of the teachers in Junior high and now that he was a senior he was built like a wall. I froze and was about to turn and run when he came around the corner and saw me. He never skipped a beat and a huge smile broke out across his face. "Momma, I have to go. I told you I ain't sleepin with Trisha. I aint gonna get her pregnant. Now I have to go I have class."

Marcus flipped the phone closed and then tossed it down on the bench. He took my clothes and tossed them with his phone. "I wasn't lying when I told my mom I wasn't gonna get Trisha pregnant. Do you know how I know that?"

I shook my head no as Marcus spun me around and pushed me against a locker. "I am going to show you."

Marcus unzipped his pants and I felt his monster cock slip into my panties and pierced my ready opening. He pumped his cock in and out of my boipussy so slow that I could imagine him cumming, but it was more than enough for me. I came shuddered and came hard soaking the front of my panties. Marcus just kept up his slow pace, as my boipenis rubbed against my wet silk panties I was lulled into a state of pure ecstasy and filled my panties with a second load of my cum. As I felt Marcus start to shudder he pumped a huge load up my boipussy. It felt so good to have his cock in me that when he pulled it out I almost cried.

Rummaging through my clothes Marcus found my phone. He played with my phone for a minute and then snapped a picture of his soft, but still massive cock. He then tossed it down and picked up my shirt which he used to wipe my boipussy slime from his manhood. "That is how you fuck a girl without getting her pregnant. You got my number now honey."

I was still leaning face first against the locker so Marcus turned me around, he raised my chin and brought his lips to mine. He kissed me deeply and rubbed my boipenis hard again. Breaking our kiss he asked, "Can I call you some time sweat thing."

"Only if it is so that you can fuck me again." I whispered back to him. Marcus chuckled and reached behind me to wipe the little bit of cum that had gotten on his hand from rubbing my panties. He gave me a smack on the ass and left without saying a word. I grabbed my things and hurried to coaches office.

The most embarrassing part of that day was that I spent the rest of that hour scooping Marcus cum out of my panties and eating it. The rest of the day was boring, coach kept me under the desk and fucked me in between each class. After the final bell Coach fucked me one last time before shoving me out of his office. HE was about to slam the door when he stopped and motioned to my panties. "Give me those they are mine now. I expect you under my desk face down and ass up ready for me tomorrow morning. Keep the stockings but wear a thong tomorrow, something that is easier to pull aside."

Coach slammed the door before I could tell him that my clothes were in his office I was about to knock when he opened the door and threw my clothes out. I reached down to grab my clothes when coach said "And wear a bra, a matching bra."

I dressed quickly and then walked up the block to catch the city bus, to the porn shop. Were slow, so all I did was rant in my head at the injustice of Coach taking my panties, my priorities had skewed a bit. I didn't wear bras often so I only had a few matching sets, and didn't want to lose them. About half way through my shift a customer came in look nervous as hell. I saw a perfect mark and went for it. A quick blow job later and I had a matching set of bra and panties to wear to school the next day.


I got into school a few minutes after the janitors opened the doors. I didn't know when Coach got to school but I was going to take chance. I stripped down to my new bra and panties and climbed under Coaches desk. He had told me to wear stockings but all of my stay ups were dirty so I opted for a pair of pantyhose that had a large hole cut in them so that they looked like a garter-belt. I dozed off after a few minutes and was startled awake when Coach shoved two fingers roughly up my boipussy. I banged my head and coach laughed as he sawed his fingers in and out of me. I had lubed up before coming into school so I was ready for him.

After spending a few solid minutes fingering me I heard Coach unzip his pants. "All right pansy get out from under there and bend over my desk."

I crawled out from under the desk and laid down on top of it. Coach unzipped his pants and rubbed his cock along the crack of my ass. He let out a nice moan and then gave me a challenge. "In ten minutes I unlock the door to the locker room and the rest of your class files in. You are staying right where you are till second period. RIGHT WHERE YOU ARE. If you can make me cum before that bell rings I will close my office door, if not well then... everyone gets to see what a little slut you really are. I wonder how long that rumor will take to get around the school. Are you ready."

Coach stopped rubbing his cock against me and placed the tip at the opening to my boipussy. Coach rubbed the head of his cock around my opening and then slammed hard into me. He let out a moan as he pulled his cock back out stopping with just the tip left in me. "Alright cunt, time to make me cum."

I started to push back but coach slapped my ass hard. "Beg me to fuck you."

I knew I didn't want to be put on display so I started begging like a wanton whore "Please coach, please cuck my naughty little boipussy."

It worked coach slammed hard and started to pull back again, "Oh god your cock is heaven please fuck me harder."

He was barely half way out before he slammed it back in. "YES YES PLEASE USE ME HOLE, fill it with your massive godlike cock. Don't stop keep fucking me like the useless little whore that I am. Put me in my place make me your bitch. Fill my body with your hot sticky man cum. Oh god please bury your cock deeper and deeper in my boipussy."

Coach came with almost a minute to spare, I came too pumping a load into my panties. My load got smeared around between my stomach and the desk. Coach pulled his softening cock from my backside and hurried to pull his pants up. He didn't even bother to clean himself up. When I rolled my gaze to the door my whole body spasmed as I realized why, stand in the door way was the schools principle, Mrs. Blackthorn. "Just what in the hell is going on in here?"

Coach stumbled for words but was cut off by the principle. "You get to class."

I started to stand but she stopped me in a scathing tone. "Not you, you little tramp. Get to class Coach I will deal with you later."

Coach finished zipping his pants and scurried out of the room. The principle closed the door and walked around the desk behind me. "I have worked very hard to get where I am. I am a good person I do what is right, most of the time, and now all that will be ruin because one little sissy tart wanted to skip changing out so she fucked her coach."

"That isn't what is happening. I promise." I was going to explain but Principle Blackthorn smacked my ass so hard I jumped.

"When I want you to speak, I will put the words in your stupid little mouth." She then smacked me again harder than the first time. She then picked up the phone and punched a few numbers. "Caroline, connect me with Billie Winters parents. No wait his mother. Yes I will wait."

I couldn't hear the other end of the phone but I saw my whole life crashing around me. I begged even as she smacked me telling me to hush. "Please, please please don't say anything to my mother I won't cause trouble I won't say anything to anyone. I won't get caught I won't cause you any trouble I promise. I will do anything just hang up the phone."

"Hello Mrs. Winters, I apologize someone just walked in my office. Can you hold a moment." I looked over my shoulder and watched Principle Blackthorn cover the mouthpiece of the receiver. "Did you say anything?"

I nodded yes and she flashed a wicked smile. "Sorry about that Mrs. Winters people just pop their heads into my office all the time. I wanted to ask you about chaperoning some upcoming after school events. The PTA is having the hardest time getting volunteers."

Principle Blackthorn rolled the coaches chair closer to me and sat down directly behind me. She reached up and took a hold of the back of my thong panties and pulled them to the side. I watched over my shoulder as she lifted her leg and pressed the tip of her heel to my boipussy. "I have got to tell you I have heard very good things about that boy of yours."

She pushed the heel in and snapped her fingers. I didn't know what she wanted me to do at first but then she started to push in and out of me with her heel and I got the idea. I spent the next hour fucking myself with the heel of her shoe while she talked to my mother. I came three times and actually held my hand over my mouth so that I wouldn't cry out. Finally a few minutes before the lockerroom filled with sweaty teenagers she pulled her heel from me and hung up the phone. "OK, Sissy boy here is how this is going to go down. You will wait here until the next class has gone out to the field and then you will make your way to my office. You are only allowed to wear what you are wearing now. If you are late you will be punished. If you don't show up, I will call your mother horrified at what I have found out."

Once she was at the door Principle Blackthorn turned back to look at me. "Do you have any questions?"

"Can I please wear some clothes." I begged her, my voice trembling. She walked over to me and pulled me up from the desk. She looked at the puddle of cold cum I had left.

"Clean that up, quickly now." She said her voice a mixture of sweat caring mother and vindictive mistress. I didn't ask or question I dropped to my knees and licked the puddle clean from the desk. "Well aren't you just a perfect little sissy pet. Ask coach if he has something you can wear. But you still must be wearing what you are wearing now. Whatever he gives you goes OVER this."

Category: Transsexuals & Crossdressers Stories