0 comments/ 77237 views/ 7 favorites The Training of Sissy Paula Ch. 2 By: submissive~pet~ Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was being to think you had. She replied back she had not forgot about me, but that it was a part of my training. I have a task for you on Friday morning, if you can get out of work slave. Yes Mistress i beleive i can get out of work. Great slave. Today you will go out and buy a slutty looking latex mini dress one that barely covers your ass. You will buy a pair of black panties also. The panties you will carry to a seamtress and have this sewed onto the ass of the panties, sissy paula (left cheek) and property of MISTRESS CAROLYN on the right cheek. Yes Mistress Carolyn i will do that. When you get to the seamtress have her call me slave. Yes Mistress Carolyn. i went to the store after work Thursday. The dress was easy to find and so were the panties. The hard part was the stemtress. Once i got there and told her what i needed done and gave her Mistress Carolyns phone number. She just smiled, picked up phone and gave her a call. i don't know what all was said. but soon i was between her legs licking her hot hole as she did the panties. Once she was done she sent me on my way. Friday morning i got my task for the day. The task was to get dressed in my new items, and then go to the adult book store, go to booth 7, then knock 3 times then 2 more, then 4 times. If i was late there was a penalty to be paid. A larger item ion my butt and another 2 weeks in the chastity belt. i headed out the door at 9 a. m. i had 1 hour to get there, i thought that was plenty of time since the store was only 20 minutes away. First the car would not crank, then after about 15 minutes it started. I was on the road and about 10 minutes pasted, the tire went flat on me. oh no there aint no way i will make it now. i hurried along trying to change tire. i had 25 minutes to get there. When a car pulled over. May we help mame. i tried to use my feminine voice to speak. i am almost done guys thanks anyway. You got us all horny with the way you moved your ass while you were fixing that tire. We need some relief and its your fault were this way you teasing slut. You have 2 choices. Suck all 3 of us off, or we will stripe you naked and take your car. i got on my knees, and opened my mouth. Damn my luck. i sucked them all off and they left me there on my knees. i was 20 minutes late getting to the store. my heart pounded as i did the code on the door. Slave your late, and i dont want to hear any excuses. Take down your panties sissy. Yes Mistress Carolyn. I am going to put this big fat dildoe up your sissy hole, it will remain there for 1 month. Yes Mistress Carolyn. Now weres that key? Got it, This is going to hurt like hell, I got an extra large one for your late ass. Please Mistress i tried to get here on time. To bad you didn't make it. Over now and reach back and spread them cheeks. After i lock the belt back on your going to be kneeling in front of this hole for 8 hours. Umphhhhh ummphhhhh ouch. Shut up sissy slut and take it all in. It will be in there for one month, i will be giving you enemas every other day to keep it clean back here. Plus I think you would be wise to go on a liquid diet. There its in now sissy. Ok its bondage time for you my little sissy. This will keep your mouth on the hole till i get back. Hands behind back sissy. there these will hold you just right. Now for some head gear and the leash. The leash goes throught the hole and you will be bound to this hole for 8 hours, no telling what will be touching your lips. Oh and i am planning a party for tomorrow night also This clip board will be in other room with instructions for invites and what all they can do with you for the next 8 hours. Ok my cock sucking sissy its time to serve all the horny men. I will be back in 8 hours, if i don't get held up in traffic, or find a stud that will keep me occupied, and cause me to forget about you here on your knees with big fat black cocks in your mouth. That right mostly black men come here my little sissy. I just may have to remove that belt tomorrow night if enough big fat cocks show up. Bye bye sissy. i could not see the cock as it pressed against my lips. my mouth opened to invite the cock in. It was a fat cock. My mouth stretched wide to accomidate his thick rod. He pumped his cock in and out forcing it all the way down my throat. i gagged some as his load filled my mouth. i was on my knees sucking cock after cock all day from around 10:30 a. m. till about 10:30 p. m. Mistress Left me there for 12 hours. My mouth was sore from all the hard cocks my stomach acked from all the cum i swallowed. I tried to keep a count of how many cocks went in my mouth that day. i averaged a load of cum every 10 minutes or close to that. My count was 72 cocks. The clip board had all the names and phone numbers of the men i had sucked. Mistress Carolyn showed it to me. There was 76 names on the list. Oh my sissy looks like that belt will come off tomorrow or should i say tonight? Better get you home and let you rest up for tonight. I will make the arrangements in the morning. We went back to her place, after a bath i was put to bed, tied up spread eagle on my stomach. Wake up sissy time to get ready for your service to the many men i will be having you serve. To be continued... The Training of Sissy Paula Ch. 3 My eyes were blurry still from not getting enough rest. Mistress had me go shower, and make sure I was smooth all over. The outfit she had picked out for me was a wild looking mini dress. Black latex with half moons on each side that would be over my butt cheeks. She helped me with the outfit and bondage gear. Oh my sissy you’re going to have one hell of a sore ass and mouth in the morning. The doorbell rang; I went and got on my knees at the door. Mistress cuffed my wrist to the ankle cuffs, and told me to greet each man with 5 licks on their assholes with my slut ass licking tongue. Hello guys take a necklace from the box red is for cock sucking and pink in to fuck my sissy’s asshole. There are 40 of each necklace. Sissy licks his butt well, since he is only one here so far, lick till the bell rings again. The bell rang after about 3 minutes of licking his butt hole. Damn that felt good you asshole licking sissy. I may have to come here more often. Well Sir we will have to work something out. Thank You Carolyn. Hello and welcome take down your pants so my slave can see that your butt hole is clean. It is Carolyn. Let my slave make sure. O.k. Is he clean slave? No Mistress. Well clean him slave. Yes Mistress. Wow here comes about 20 for you to lick sissy. Ok now everyone is here line up in a straight line. My sissy is going to take each of you down her throat for 10 seconds. Then the fun will begin. Guys help her to take them cocks down her throat, feel free to pull her head onto your cocks. Mistress they’re so big I can’t swallow all of them big things. Oh but sissy you can and you will. Now to remove that belt and dildoe. Ok now open wide, this item will keep that mouth open wide, and keep your teeth off of they’re fat cocks. It looked like something a dentist would use to keep a persons mouth open. Try as I might the thing kept my mouth open wide and ready for the cocks to enter and penetrate my waiting throat. Slave on your knees now. I could not speak; I just did as told. The men all ready to give me a taste of their hard cocks. Mistress had a timer in hand. Ok guys begin. The first man was thick and about 10 inches long; he rammed his hard meat down my throat and held it there till Mistress said next. The second man was long, I just knew it would hurt as he pushed all 14 inches down my throat. This went on for a good while, until I had got to the last man. I had taken ever cock all the way down my throat. Now comes the fun part sissy. Guys you all had 2 beers like I instructed right? Yes came many times. Ok my sissy needs a long enema, and a lot to drink. I was placed on a horse with my mouth and ass level to their cocks. Slave if any of that pee comes out of your mouth, we will have this part again next Friday night and Saturday night as well. Well I guess you figured it out. There will be more parties. After about the 6th guy filling my mouth with pee I could not hold any more. My asshole was being penetrated and filled with pee as well. Ok now its time to enjoy my slaves mouth and asshole. Fuck her till you cum and if you want seconds go get at the back of the line. I would like about 50 of you to cum in that big tub over there. I need to make lots of ice cubes for my slave. From now on whenever he drinks something he will taste some of yawls cum. I was left on the horse, the weird device still in my mouth. They wore me out that night with all the fucking they did to me. Well this never really happened, but umm it would be so nice if some of it did. I have served 4 men at one time for real. I love going to the glory holes and have sucked about 20 cocks in one night. I hope you enjoyed my story. Sissy Paula. The end, or is it? Part 4 coming soon. Sissy Paula meets Big Max. The Training of Sissy Paula Ch. 4 Mistress Carolyn Found the biggest cock she could find. He had to be 16 inches and his cock was fatter than my wrist. He told Mistress it takes him around 4 hours to cum. Mistress told me she would not make me try to swallow his big cock, but it would be visiting my asshole that night. I was dressed in my red velvet mini, no panties, silicon breast as big as Dolly the singer lady. My butt well lubed from Mistresses fist sliding in and out of it for 1 hour as I licked her pussy to climax 3 times. The bell rang and Big Max came in. Mistress had me bury my face between her legs. Big Max slowly pressed his massive tool into my waiting hole. He is big isn't he sissy? Ummmmphhhhh yes Mistress to big. None since sissy no cock is to big for that asshole of yours. His massive pole started to burn as he pressed deeper and deeper. I licked at Mistresses pussy and clit as he pushed further in. Ummphhhhhh ohhhhhhhhhhhh it burns Mistress please have him stop. Shut up and lick sissy, that cock is staying were its at. After about an hour it started feeling good. He was slowly pumping his huge member into my hot hole. Mistress had gotten up and went to get some drinks. She suggested that max carry me to the couch and have me sit on his cock while we had some drinks. He picked me up and carried me over with cock still in my burning hole. We drank vodka, and sprite. I don't think I have ever drunk that much before. They each had 2 serving and I drank the rest, I was famished, and I thought the whiskey would help with the fucking I was getting. Sissy I invited another man over for your mouth. Now I want to see you lift up almost off that cock and then all the way back down on it slave. Yes Mistress. Do it until I say stop. Yes Mistress Carolyn. Ahhhhhhhh I hear a car door. Hello Carolyn I brought 2 friends along they asks if they could watch. Sure they can watch, and join in also. Let me fill that cock in my pussy honey, I am so horny now. You got it Carolyn. Hey guys her mouth is yours take turns. Carolyn I want to fuck her likes a woman can I carry her to the bedroom> Sure Max. Guys you can fuck her mouth while I work this little asshole over. I bet she wishes I would cum. The guys all got in the bed, I was placed on my back with legs on Max's shoulders, and he pushed in hard. The other 2 men were at my mouth, rubbing their cocks on my lips. Sissy I can cum now if you like, but if you say yes, I will be using your mouth as my toilet. Yes Max please cum. Let me get Carolyn so she can know what you agreed 2. When I say toilet, I mean toilet. I have never had that done before Max. Well if I cum you will have to be my toilet. Please don't cum Max. Keep fucking me. I thought you would change your mind. I was fucked all night long by all 3 men. After Max had been in me for so long, I now have to wear diapers all the time. My asshole want closes back up. Mistress has him over twice a month. Well that's all for now. To be continued... The Training of Sissy Paula Ch. 5 After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he wanted to do some role-playing. He gave me a made up report card and had me dress in an outfit for a toddler. Frilly pink panties, over my diaper, and pink rubber panties, a pink dress with puffy sleeves and white lace all over, pink buster brown shoes and little bootie socks which were pink with lace. I went up to him with the report card. Oh my sissy Paula, what will I do with you? F - in every class. Honey bring me the big paddle for our little sissy. Yes dear. Mistress Carolyn was playing the part as honey. Here you go dear. Down with them panties sissy. Yes sir. Call me daddy, you naughty little sissy. Yes daddy. I think 100 licks for each f- should get you acting right in school. Let’s see 6 classes all f-. Oh I just thought of another punishment to go along with the spanking. Carolyn please get me a big bowl of ice cubes. You got it dear. O.K. sissy I am going to insert all the ice in your asshole, and by the time I am done spanking you it should be melted. Get the penis gag Carolyn. Here you go. Remember this sissy, I used it on you the first night me met. Now look at you, your a pro at taking it all down your throat. The panties came down, along with the diaper, and plastic panties. He slowly inserted one cube at a time having me count out loud and thanking him for the attention he gave my asshole. The ice was packed into my asshole. Bet that’s cold. Yes daddy it is. Well after this paddle starts you want be thinking about that asshole full of ice. He tied my ankles to the stool he was sitting on, then he tied my wrist to the hook in the floor. My ass was high in the air as I lay over his lap. He didn’t hit hard at all, but after 600 licks it did sting some. He put my diaper back on me, then he told me to go make Carolyn feel good with my tongue. He rested for a while as i licked Mistress Carolyn to orgasm. My tongue got a long work out as I licked and sucked Mistresses pussy to 3 climaxes. He slipped his hand into my diaper and started fingering my butt hole. The session was not all that bad, and he even made me cum in the diaper. He worked his hand up my anal passage with ease. Soon after he managed to move around so that his cock was at my mouth. I sucked on the head of his cock for about 5 minutes, then I began licking up and down the base to his balls. Umm sissy paula that feels wonderful. I didn’t say anything,my mouth continued to pleasure his hard rod, bringing him nearer to his goal of feeling my mouth with his sticky cum. He thrust all the way down my throat and started humping my face as if he were fucking a wet pussy. His cum went in my mouth, and on my face. Mistress came over and gave me a big kiss on the lips. She and I kissed for about 5 minutes, exchanging the cum back and fourth between us. Daddy went to get something from his car. It was the most beautiful dress I ever saw. Pink and frilly lots of petticoats, and puffy sleeves. He also had matching shoes for the outfit. O.K. sissy were going out to dinner tonight. Yes daddy was all I said, I knew there was no need in protesting the idea he had in mind. I put on the outfit. Mistress Carolyn helped me with makeup. The diaper and plastic panties still on me also. Once we sat down 3 friends of his took a seat. Paula your meal is under the table dear. O.K. daddy. I slipped under the table and unzipped the first man i got to, pulled out his cock and began sucking him. He started peeing before I knew what was going on, I gulped and gulped to swallow it all, Didn’t want to smell like a toilet. He pushed me away. I had an idea that i would be drinking all their piss. I unzipped the next mans pants and soon he was filling my mouth with pee as well. When I got to Mistress Carolyn she told me to go to the restroom. I was nervous as I went to the restroom, seemed like all eyes were on me. Paula you will put this sign on once you get in the men's restroom and kneel in the stall and wait for your first golden shower. For now thought I have to piss also, and your mouth is the toilet tonight. By the time we get home that diaper should be full. After drinking her pee, I went to the men’s room and put the sign on. It read : sissy paula needs a bath and a snack. Piss on her and cum in her mouth. Daddy came in and put a hose down my diaper and ran it over to the urinal, he put a funnel on the hose and hooked it to the urinal. Now don’t let know one get any pee in that diaper sissy. He laughed as he went out of the rest room. Soon a man came in and started peeing on me. He pressed his cock to my lips and pushed all eight inches down my throat. Umm I have not cum in about a week. He gave me the biggest load of cum I had ever had. Well this went on for about 4 hours. I walked out of the toilet dripping wet, with a soggy diaper. I had to ride in the trunk. That was a wild experience I will never forget. The Training of Sissy Paula Ch. 6 My Mistress goes to a lot of trouble to fix my nails, hair, and makeup. Once she is done she tells me to follow her. I follow her to the car as instructed. Paula take off the panties. Yes Mistress Candy. Now for a very special long trip Paula. Where are we going Mistress Candy? You will see in about 3 hours sissy. O.K. Mistress Candy. Now I want that asshole loss once we get to were we are going. Sit down on that big dildo sissy Paula. Then I will fasten your seat belt. Wouldn’t want my sissy getting hurt bow would I? Mistress that is huge i don't think it will fit in my asshole. Nonsense sissy. Now no back talks start stretching that ass over the dildo now sissy. Yes Mistress. i slowly began trying to slide onto the rather large dildo. It was at least 12 inches long and 10 inches round. (Actually my asshole is stretched over the large dildoe as my fingers write this story) Paula sit down on it now are I will be using the cane on your ass later. Yes Mistress Candy. . With a grunt my asshole slammed hard down on the dildo it began hurting. Good slave now let me fasten that seat belt. There that will keep you safe and packed full of cock for the next 3 hours. Mistress it hurt, My asshole can't take it for that long. Yes you can paula, and to make sure you stay on that fat dildoe, I had a seat belt made just for this trip. She reaches under the seat and pulls a belt between my legs, then a second belt is pulled between my legs, she puts them over my shoulders and attached them to a hook on the back of my seat. Umm my little sissy that will keep you occupied for the trip. We headed down the road. Mistress Candy said she was going to take the scenic route, sense there were lots of bumpy roads to travel down. I bounced up as she hit a bump only to find the dildo all the way back in my asshole. She would stop and go just to make it jar me a little. Paula I had something neat done to the car. What is that Mistress? Let me show you. Please do Mistress. With that said she pressed a button and the car started bouncing up and down. Umm Paula you will grow to love this. She let the car bounce for 15 minutes. O.k. now off to see my friends. You will entertain all 30 of my male friends tonight paula. With your mouth and asshole, your hands will be getting a work out as well. Yes Mistress. How is that butt feeling paula? It feels a lot better now Mistress. Good now I know you will love sliding up and down on 3 cocks at the same time? How will i be able to do that Mistress? You will see in about 2 hours. Now reach over here and stroke my cock. Yes Mistress. Its just too bad that chastity belt has to remain on you for 3 more days paula. However you brought it on yourself. Yes Mistress i did and i am sorry. After the party I am going to put the dildo in your ass for the remaining punishment period and put you on a liquid diet. Once we got inside the big Mansion, Mistress had me get on my knees. All the men came up to me and gave me a taste of their hard cocks. Guy’s paula’s asshole is ready for 3 cocks at a time; there are 30 of Yawl. So it looks like paula here will be getting 10 good butt fuckings tonight. Three of the guy’s got in the special made contraption that made it possible for them to all get their cocks side by side. O.K. paula go over there and ride them hard cocks until they all cum. Yes Mistress Candy. Lick my asshole while you slide your sluttish asshole on them hard dicks. Yes Mistress Candy. Their cocks burned a little as i slide up and down on them. Mistress fed me her ass, and had the others feed me their assholes as well. After i had taken all 30 cocks in my asshole, i was put in the bathtub. Open wide sissy its time for a long golden shower, you don’t have to swallow it but you will have to taste every drop. They all gave me a mouth full that trickled into the bathtub. Mistress candy helped me get dressed, then we headed home. After the party i was told to put the dildo back in and it was locked in place with the use of another chastity belt. The End.