Category: Transsexuals & Crossdressers Stories

Sissy Slut Ch. 02

by Scribler©

Tammy giggled before she said. "Lets face it Tom that butt plug isn't for a girlfriend at lease my boyfriend better not bring home anything that big for my bottom. He'll find it in his own bottom first. From the way your lisping that sounds like a new tongue piercing you have and since you're not wearing a wedding ring I assume you're not married. Now don't get embarrassed about this I understand how some men like having their bottoms played with and this is one way to do it. My philosophy is, if it feels good enjoy it if it doesn't feel good stop doing it."

I didn't know what to say so Tammy took this to mean she was right and steered me back to the register with the nightie in hand. Once there she showed me another box and said, "I think you should have this too. It's an anal cleansing kit you should use before you start to play. It will clean you out so nothing comes out nasty."

After ringing up my purchases Tammy walked me to the door and said, "Now you make sure you come back. I have a lot of toys and other things for someone as adventurous as you are. Remember I never judge." She then kissed me on the cheek before I walked out the door.

I know I been had as I went in for a forty dollar butt plug but wound up spending close to two hundred. I'm sure she worked on commission but I didn't care as she made me feel good about myself. I went home feeling good for the first time that week.

I laid out my purchases on my bed and looked them over. I knew my sphincter and shrunk down to its normal size and I also knew I was going to get fucked again this weekend. At leased that was what I was figuring on. I also knew I didn't want to go through the pain I did last weekend, well as much as I could avoid anyway. So I figured if I stretched myself out with the butt plugs I would be ahead of the game.

I took the cleansing kit into the bathroom where I gave myself four enemas to get myself very clean. I then went back to the bedroom were I picked up a medium size butt plug and after lubing it up I tried to push it into my ass.

I was right in the fact that my sphincter had shrunk back down. I felt a bit of pain as I tried to force my anus open for the plug. This was the same size plug I wore with the maid's uniform and I was sure I would have to wear it tomorrow evening or at the very latest Friday morning.

In the end I couldn't get it in with out pain so I switched to a smaller one. This one went in easily so I kept it in while I made dinner for myself. But instead of wearing a pair of boxers and a tee shirt like I normally would wear around the house I put on the nightie and matching panties. I told myself since I bought them I should at least wear them. After putting on the nightie and the matching panties I started making my dinner.

After dinner I decided to change the butt plug for a larger one. This time the one I had wore with the maid's uniform slid easily into my ass. In fact it felt quit comfortable. While I let my bottom get use to the larger plug I sat at my computer and check my mail.

I received one letter from Tally telling me she was thrilled to learn I had accepted her ownership of me. She also said she was waiting impatiently to have my lips wrapped around her sweet cock once more.

There wasn't any pictures attached to the letter. I figure she didn't need anymore threats to insure I would be coming back on Thursday. After all, my nipples were pierced with her rings, my tongue was pierced and my ass was tattooed claming her ownership of me. What more did she need. After I finished the letter I went back into my bedroom and removed the butt plug.

There were two more plugs that were larger than the one I had in me. The bigger of the two was the one that I had in me at the party. The second biggest one was a vibrating butt plug that had a slid control to adjust the speed of the vibrator.

I first inserted the larger plug. It went in though it really wasn't that comfortable. I figured I just had to get use to it so I went into my living room and started watching some TV. Even after twenty minutes it still felt uncomfortable so I decided to change to the vibrating one.

Since the larger one had already been in me the slightly smaller one went in easily. The slid control had a clip on the back so it could be hung from a belt. I clipped it to the waistband of my panties and went back into the living room to watch TV.

I really had no plans to use the vibrating part of the butt plug. I mean I was just putting the butt plug in to save myself the discomfort this weekend. I actually hoped this wasn't necessary as I hoped I could talk Tally out of the pictures and get away before anything really happen to me.

My curiosity got the better of me and before I knew it my fingers started playing with the slid control. When the plug started vibrating it felt like I was hit with a jolt of electricity. My whole bottom seemed to come alive with the vibrations. I was really surprised by how good it felt.

My cock came to life as well. It swelled rapidly to full erection and it seemed to vibrate along with the butt plug. With in minutes the TV show I was watching was forgotten. I was slowly stroking my cock though the satin panties with my right hand while my left hand manipulated the slid control.

I never used masturbation for recreation like some men do. I only used it to relieve sexual tension between girlfriends. But what I was doing now was so different I couldn't stop myself. It felt like nothing I ever experienced before. After a few minutes of this I wanted to get comfortable. I wanted to really enjoy this new experience so I decided to go to bed.

I lay down on the bed and quickly turned the vibrator back on. I immediately felt that wonderful feeling fill me once more. I closed my eyes as my hand slowly started to stroke my hard cock thought the satin panties as my mind drifted.

My mind went to the last time Tally had fucked me. Thought I didn't want my mind to go there I didn't fight it either. Quickly I saw Tally above me thrusting her hard cock in and out of my tender asshole. Murmurs escaped my lips as she drove her cock deep.

I don't know how long it lasted but all to soon it ended. Just as Tally started to fill me with her cream in my dream I started cuming. I came hard and it seem to last forever. When it was over I fell into a deep sleep.

When I awoke it was six thirty in the morning, my normal time to get up. At first I wasn't sure where I was or what happen to me. The butt plug was still firmly imbedded in my anus but the vibration had stopped. When I remembered the wonderful experience I had the night before I just wanted to do it again. But the batteries in the slid control were dead and I didn't have another set so I got out of bed to face the day.

When I was standing I saw the pale pink nightie was stuck to me in spots and my cock was out of my panties. I knew I had to wash them, as I was sure I would repeat the episode again.

I couldn't shower due to the tattoo so I gave myself a sponge bath making sure to get every inch I could clean. After pulling out the butt plug I used the cleaning kit again before washing the nightie in the sink. I hung that to dry in the shower before getting dressed.

Work was abysmal, as I had to get six reports done before I could leave. I wanted to get out early so I could be at Tally's with plenty of time to spare but that didn't work out either. In fact I wound up leaving work late that day.

I rushed home to get clean and change before going to Tally's. I used the cleansing kit again, as I was sure Tally would want that. After inserting the butt plug into my ass I dressed in a pair of jeans and a pull over, as I was sure I wouldn't need anything dressier.

As I was driving to Tally's I wound up in a traffic jam that cause me to drive at a snails pace. By that point I knew I wouldn't make it to Tally's on time. In fact I was a half-hour late when I pulled my car to a stop at her door.

I quickly disrobed and threw my clothes into my car before running naked to her door. After getting on my knees I knocked on her door and lowered my head to the ground. After a few minutes I knocked again.

Tally opened the door and shouted, "You're late I told you I may not let you in if your late now you just wait there until I decide if I want you at all."

Before she could closed the door I said, "I'm sorry Mistress but there was a traffic jam that caused me to be late."

The riding crop came down on my ass like a shot before Tally said, "I didn't ask for an excuse. There is no excuse for being late now wait there and I'll think about letting you in."

I waited on my knees with my head on the floor for well over an hour. I had thought about going home several times, but I knew I couldn't. I had to find out what she would do with those pictures. I thought this was the most humiliating thing I ever did, but then I heard a car drive up behind me.

I had to make a quick decision. Did I hide until the driver was inside or did I hold my place and wait for the ridicule? I was struck with a fear when I thought it could be the cops though I don't know why they would come, seeing Tally lived in virtual seclusion. I figured my best bet was to stay where I was and see what happens. Surely Tally wouldn't let anything happen to me.

I heard the car stop and someone get out of the car. A few seconds later I heard a man chuckle as he stood above me before ringing the doorbell. I could only see his shoes so I knew it was a man.

When the door open I heard Tally say, "Good evening Scott, my you look good tonight. Just kick that worthless sissy aside and come in."

Before he could kick me I started to move. I still caught some of his foot in my side before I could scurry out of the way. Tally and Scott went inside and once more I was left kneeling outside.

About twenty minutes later I heard the door open once more before I felt the whip on my ass one more time. Once the whip got my attention I heard Tally say. "Alright Sissy you can come in now. I warn you now you had better do as your told. I will not stand any insolence from you. Now get inside."

I went to stand but a slap from her riding crop dropped me back to my knees before she said. "No one told you to stand now get your sissy ass in the house." I crawled on my hands and knees as I felt Tally right behind me.

Once inside Tally closed the door before telling me to kneel up. She quickly put a collar around my neck and slapped my face hard. I was then told to go to the playroom and wait for her.

I had thought she left me as I crawled on my hands and knees to the basement stairs. I thought it would be all right to stand while I walked down but I soon found out that Tally was still close at hand and standing wasn't an option.

As I got up I was hit several times with the crop before Tally shouted. "I told you not to stand sissy. Slither down on your belly if you have to." I slithered down like a worm to the basement and then crawled to the other end and into the playroom.

Tally didn't follow me down but I didn't have to wait long before she and Scott came into the playroom. I watched as they kissed deeply and I watched as Tally groped his manhood. He played with her beasts and I saw him reach behind her to feel her bottom. Tally moaned sweetly while their lips stayed connected.

When their lips separated Scott nodded his head toward me and asked, "What are you going to do with that?"

Tally sighed as if I wasn't worth the bother and said, "I'm not sure he was a half hour late when he got here and to top that off he knocked on my door twice like he was impatient for me to answer it, really the nerve of him. I guess I could always sent the pictures I have of him to his boss and ruin him for life. Lets not worry about that tonight. I want you to make love to me."

Scott was tall about six feet six at the least. He had very broad shoulders and from what I could guess was very muscular. His skin was rich ebony and his head was shaved bald which caused it to shine.

Tally looked small standing next to him and her skin seemed ghost white in comparison. Her hand moved rapidly over his manhood and I could see he was already hard by the huge bulge in his leather pants.

In short order Scott had removed Tally silk white blouse and his hands cupped her white breast. His hands were huge, as they seem to dwarf her D cups breasts. Tally moaned when Scott pinched her nipples between his fingers.

Scott pulled his mouth from Tally and said as he nodded to me. "Look at the little pervert he's staring at us and his tiny dick his hard."

Tally laughed as I looked away before she said. "What do you expect, he knows a beautiful man when he sees one."

"I understand that," Scott told her. "But he should know better than to stare like that. What kind of manners do you teach him."

"I've only had him a few days so I really didn't teach him much except to love sucking cock and have his sissy ass filled. He really likes that don't you sissy," Tally asked as she walked over to me wearing a plaid mini skirt and heels.

I didn't answer her, as I didn't want to tell either of them I like sucking cock and getting fucked. I didn't want to answer because I knew if I told her I didn't like it I would be hit for lying even if it was the truth.

But a non-answer was as bad as telling her I didn't like it as I received several slaps across my face before Tally said. "You ungrateful slut how dare you not answer me." She turned to Scott and said, "Strap him down to the horse and we can teach him some manners."

Scott came over, grabbed me by the hair, and literally yanked me to my feet. I thought he was going to pull my hair out by the roots. I screamed as the pain shot through my head, but that wasn't enough for Tally as she picked up a riding crop and slapped my balls with it.

Nausea flowed though me as Tally said, "Wait Scott I don't want this worm getting any enjoyment out of this. And I don't want him squirting his sissy juice all over the floor like last time." Tally bent over and put a cock and ball harness on me.

Once the cock and ball harness was locked on Scott pushed me over to the pommel horse and held me down while Tally strapped my hands and legs to the feet of the horse. In stead of being bent over the horse length wise like the last time I was bent over the horse width wise. It was more uncomfortable this way than the other way for me.

Once I was strapped down I heard Scott say from behind me, "I see you already marked this one."

While she was still standing in front of me Tally yanked my head up by the hair and said while looking me in the face, "I though this one had real potential after the way he made love to my cock on Sunday. I may have been premature in my acceptance of him."

In Tally's hand was a long red wooden paddle like you would see at Frat initiation. The paddle part was eighteen inches long and the handle was long enough to use two hands on it. She handed it to Scott and said, "There you go my love your favorite paddle. Make sure you give him a few extras for being late though I will make him pay for that later this weekend."

When the first smack of the paddle landed on my ass it hit both cheeks at the same time. It drove all the air out of my lungs as I screamed out in pain. The pain was like nothing I ever felt before and it nearly caused me to pass out. At the same time Tally smacked my face with an open hand and that only added to the pain I was feeling.

I was hit over and over again with the paddle and the pain only seemed to get worse. This time there was no euphoria to over come the pain. Tears poured down my face and screams leaped from my throat.

Finally Tally called a halt to the paddling and asked, "What are you?"

I swallowed a few tears and said, "I am a sissy slut an ass fucking cock sucking sissy slut that only wants to please."

I heard a giggle in her voice as she said, "Very good sissy slut now tell me do you like sucking cock and getting you sissy ass filled?"

"Yes Mistress I love sucking cock and getting my ass filled with cock, Please may I suck your cock," I said humbly.

Tally laughed and said, "No sissy you can't but you can suck Scott's cock. He loves having white sissy boys like you suck on his big black cock. You're in for a treat now sissy. Asked Scott if you can suck his cock."

Scott was now standing to my left and his pants were open. His cock was hanging out side his pants. I know my eye must have bugged out of my head at the sight of his cock. I was well over twelve inches long and as thick as a beer can. I could see it was already hard but it was so big in couldn't stand up on its own.

I was shocked by the size of his cock and I'm sure Scott knew I was. I heard him chuckle before he said, "Come on bitch beg me for my cock. You know you want it. You know you want me to fuck that sissy mouth of yours."

I didn't want to beg him for it but I knew I had no choice. I didn't want to get beat again, as my ass was already on fire. I had to play their game. I had to beg for it. In a very pleading tone I begged, "Please Master Scott please may I suck you big beautiful cock."

Scott moved closer and raised his cock to my mouth. I tried to get my lips around the head but he pulled back just enough so I wound up smacking my lips together.

Scott laughed and said, "I guess you really want it, the way you're smacking your lips. But first you can start by licking my balls." Scott moved closer and raised his cock out of the way so I could get my tongue on his balls.

His balls were hairy with tight little curly black hair. The mix of his leather pants and his manly odor made his scent strong. At first the smell was unappealing but after a few seconds it wasn't that bad. In fact it was rather erotic.

Like the rest of him his balls were big as well. They felt like they were the size of a small lemon. When I tried to take one in my mouth it barely fit. I licked and sucked on his balls and his nut sack for about ten minutes before he stepped back and leveled his cock at my mouth.

This time he didn't stop me as I encircled the head with my lips. I was actually surprised I could get my lips around his cock head. I sucked on the head for a few seconds before Scott started to push it into my mouth.

My mouth filled quickly and when I thought I couldn't take any more Scott pushed hard with his hips. This sent an inch or two into my throat. I had thought I didn't have a gag reflex any more after last weekend but Scott's cock proved me wrong. I gagged around his cock and choked on the head a bit before he pulled out of my throat.

Scott laughed at me and said, "You better get used to it sissy. I'm not stopping till your sissy lips are tickling my short hairs." Scott then pushed his cock back into my mouth and into my throat.

Scott continued to fuck my mouth and slowly he worked in more of his cock. My gag reflex went away and I was able to handle his meat better. At the same time I felt the butt plug being pulled out of my ass. Once it was gone I felt the head of Tally's cock slide into my ass. At least I thought it was Tally.

Tally's cock slid easily into my bottom. When she was half way in she said, "You've been keeping you sissy ass open for me haven't you. Now tell me you don't like having you sissy ass filled with cock." With her last word Tally slammed her cock all the way into me. All I could do was moan around Scott's cock.

They fucked me like this for a few minutes until I felt something tickle my lips. It only took me a second to realize it was Scott's pubic hair that was doing the tickling. I was amazed I could take it all.

Scott didn't seem too impressed when he said, "That's it bitch I knew you could do it. All you sissy's can take a big cock. Now start moving those lips and act like you loving this."

Category: Transsexuals & Crossdressers Stories