#832- Sissy Story 21 - Until your ass turns into a pussy

Happy new year Sissies!!!
in this first sunday of 2012.. truly a fantastic story of submission..
Dominant gay man introduces virgin sissy to paradise..
In a slow process.. of awareness.. of her own gay tastes!
becoming a submissive slut.. has often some delicious steps..
and this story.. is so detailed.. to describe every single moment of slave role acceptance.
I confess you.. for me, it was so hard.. to resist to cum.. during its reading.
so enjoy the sissy story number 21! ;)


Anna Malice



Until your ass turns into a pussy


I had known Mitch for a while, he was this gay man some ten years older than me who hung out with the same people I did. I knew he was into this whole bondage and dominance thing. I had just never really given it a second thought until he asked if I wanted to try being a slave. At first I said no, and added that I had never been with a guy even though I was bisexual. Mitch told me we didn't have to have sex; he just wanted to play and didn't have anyone to do it with right now.
I thought about it and after making him promise I wouldn't be completely naked I said yes. The first time wasn't that bad and he cut me a lot of slack since I wasn't used to it all. The fact that I was the only thing he had to play with probably made him a little more patient too.
We agreed to meet and do it again at his house the next weekend. On the first session we had agreed on what words to use if I wanted to stop it all and that I was to wear a pair of tight jeans (nothing underneath) and a collar he'd given me. His outfit was different this time though. It was all in leather, with hooks and chains and looked pretty good on him.
I was led to the living room and he told me that as a slave I should always look down, never making eye contact. I naturally did as he said anyway, I'm a pretty shy person, but now I paid attention to doing it. Then he announced that I would be spanked since I was such a naughty boy.
He sat on the couch and I positioned myself over his lap. I got nervous as he pulled my jeans down and my breathing got heavier. There was a pause and I imagined he was checking my ass out, which made me blush. I felt the first slap. I sucked in breath because I wasn't prepared for the pain. I felt his hand linger, then slowly glide over my behind and thighs. This only makes me more nervous, but when the spanking continues I forget and focus on the pain. My skin felt very sore and burning hot when the last slap fell on it.
Afterwards I was told to pull my jeans back up. The first time he had instructed me to always thank him, so I did. He seemed pleased that I remembered and told me to do a few household chores. I've always hated doing chores but I find I don't really mind right now. Every time I walked or moved my legs, I felt the sting from the spanking however.
It took a while to get all the chores done to his liking. In the mean time he'd gone to get some take-away food. Asian by the smell. He sat on the couch and watched TV while eating, and I was to sit by his feet like a pet. He would feed me a morsel every now and then. I liked this, being submissive has its appeals to me even though being a "slave" might not exactly be my thing. Well, maybe it was. I just wasn't going to go along with anything.
After that session we talked on the phone and he asked me if I had enjoyed being spanked. I said that it had been painful and that I generally didn't like pain, but that I had. I also told him it was OK with me if he did it again. I guess he got bold, because after I said that he asked if I could wear just the collar next time since it would be easier spanking me if my ass was bare... I said no straight away, but after some persuasion I agreed to just wear a thong in future sessions.
The next session he told me to use his shower and to peel off any hair I had on my body with a cream he gave me. I was to show him I was completely hair free, then put on the thong he'd bought for me and the collar.
I felt nervous standing naked in front of him, bending over to show I hadn't missed any spots and had my heart been a car I would have been pulled over for speeding. He quickly ran his hand over my genitals and ass crack and then approved and told me to dress. I did.

After putting on the collar and thong I was ordered to stand on all fours. He corrected my position a little, his strong hands on my slim, almost naked body was making me excited. He knelt beside me and started spanking me with his one hand on my lower back. After about ten hard slaps he paused to caress my buns. I felt him move the thong aside a little and then a finger circling my rosebud. He spit and I felt the saliva land in my crack and his finger was soon smearing it on my hole.
"I'm going to give you an option slave", he said to me. "I will either put a butt plug inside your tight virgin ass or I will put my whole fist inside. What will it be?"
Was that really a choice? "I would prefer the butt plug Master", I said with a shaky voice. I was aware that he was leading me down a lane that would probably end up with me being a sex toy, but even though I was scare I was enjoying this and I wanted to continue, for now anyway.
"Good. Stay still, slave", he said and pulled my thong down. He moved away, not far though, and when he returned he used both hands to spread my buns apart to expose my hole. They still stung from the spanking. I felt him licking my ass for a while, then he moved to my head and told me to suck on the plug. I did. The taste wasn't unpleasant. When he decided it was enough he placed the plug against my hole and commented on how my ass looked ready to get fucked. He pushed most of the plug inside me hard, making me scream in surprise and a little pain. He moved it out a little and then back in, mimicking a fucking motion, and getting more and more of it inside me with each push in. It hurt a lot when the widest part passed through my now tortured anal ring, but the plug narrowed down right above the base plate so my anus closed up rapidly on the narrow waist locking the butt plug securely inside my asshole.
He immediately stopped moving it when it was all the way in and pulled my thong up. One hand was again placed on my lower back and he started spanking me again. This time I not only made sounds because the hard slaps hurt, some made the butt plug push deeper and made me sound like a girl getting fucked hard. The spanking wasn't over until my ass was so sore I was sure I couldn't sit down. Ever.
I was told to stand up and walk over to the kitchen and get my master some ice. I did, but not only was it a new experience walking with a butt plug up my ass -- I also had to deal with the pain from the hard and long spanking session. I'm pretty sure it amused him watching me though.
The ice was for his drink. Which I had to make, of course. The rest of the evening was fairly uneventful, apart from the fact that I was told to keep the plug inside me until I got home and that next time I had to use an enema to clean myself before I came.
The enema wasn't really unpleasant, just odd. I actually did it twice to get some practice. I was still smooth as a baby and equally hairless so I just showered before I headed over to my masters house. Once I was out of my clothes and into my outfit I was told I wouldn't need the thong today. I reluctantly removed it and nervously followed him into the living room, just wearing that collar. I felt really vulnerable and I had butterflies in my stomach.
I was told to bend over a table and spread my legs wide. My arms and legs were quickly tied once I had done so. I was then left there for a while. I was rather comfortable where I was so I had closed my eyes for a time while waiting for my master to return.
I screamed out as something cold and slippery was quickly pushed inside my ass. Once I had recovered from the chock I realized it was just a finger, and when I relaxed it started pumping in and out of my tight hole. I moaned a little, there was no pain and I quite liked being used as he pleased. Soon I had another one joining it, and then a third. I was really stretched, I hadn't had anything big in my asshole ever and it had been a few days since the incident with the plug. It didn't help that my master had big fingers that seemed to want to split me in two. He removed them and inserted both middle fingers, trying to stretch me as wide a he could but not really being forceful about it. Two more fingers joined. I now had four fingers in me and I was begging him to stop. Instead of stopping he spit right inside my open hole to make his fingers move easier. The pain made me eyes tear up and I must have sounded really pathetic.
The fingers were pulled out quickly, another chock for me. He told me I was so tight it made him want to just fuck me hard, but since I was a virgin he was going to make things last. It scared me a bit; I was after all tied up and pretty helpless. He came around the table and held up a dildo in front of me which was actually fairly average in size, but I knew I was still very tight. He made me watch while he coated it with lube and then walked back behind me. I felt the tip of the dildo make contact with my rosebud and stay there for a second before he pushed it in a good two inches. I had relaxed to make it easier, but as the pain hit I tightened. He held still until I relaxed again and then pushed slowly. I thought it would never end - it just kept coming further and further in me. When it did end I felt so full all I wanted to do was get it out.
Then he turned it on. The vibrations felt odd and I was still feeling like I had a tree trunk up my ass. If I hadn't been tied up I would have pulled it out, but as it was I could only go along with the ride. He started moving it and told me how my ass looked from his view, how it wanted to swallow the dildo and that he was going to make me scream and beg.
The pain already had me making noises so I imagined it wouldn't take a lot... The dildo plopped out unexpectedly. He seemed to like that - surprising me with what was going in and out of me and when. Like I had absolutely no control. It was quite some time before I felt something starting to push into my hole again.
I turned and looked behind me. I immediately wished I hadn't. He was pushing a huge dildo inside me. When I say "huge" -- I mean huge! It was like a giants cut off penis and testicles. I screamed as it plopped in, and instead of stopping he very slowly kept pushing. If it hadn't been lubricated I'm fairly sure I would have gotten hurt.
Bent over that table, tied down and feeling this huge dildo slowly slide further into my bowels I considered using that stop word, but I didn't. It hurt a lot, but strangely I also felt so good. I sure as Hell had never had such a hard on in my life.
When he started fucking me with the dildo I wasn't sure if I was screaming because I was in pain or if I was just really enjoying it. After a while he started using deep, hard thrusts that really made me feel good. He must have noticed a change in my screams because he started telling me what a little slut I was who liked being raped by a toy much bigger than a normal dick. I blushed and stared down.
"You know slave, this is actually a model of my own cock", he said and my eyes widened. Mitch was a big man and it sure would have looked odd if he'd had a small dick, but this...?
"Once I'm done with watching you squirm around the toy you're going to go home and then meet me in the forest clearing, where we had that barbeque last year, in two days at ten pm." With that he slapped my ass and fucked me faster with his toy. I was so hard, I really wanted to jerk off. I started moving my hips since my hands were tied, getting dirty comments from my master who seemed to really enjoy the show I was putting up under his hands. I was coming closer and closer until I finally came hard. It hurt badly when my ass clenched around the huge dildo which forced me to scream louder still. My master had pushed it all the way in and held it there until my climax was over. Then he pulled it out slowly. I felt empty as he untied me and repeated his instructions.
I was to wear clothes that I wouldn't miss if they were ripped and wait for him in the forest, of course I had to use the enema and clean myself too. I knew that clearing since Bob and Anne usually held a barbeque there in the summers, but it was rather far in and at nine pm when I started walking it was almost dark. I got there some twenty minutes later and sat down on a log waiting. I was nervous for two reasons - no one would come to help me if I screamed (I did trust Mitch, but things can go wrong) and I wasn't sure what he'd really planned. I suspected he would fuck me with that monster dick, but then again he might just put me on a leash and pretend I was his dog.
I was excited by the idea of having his dick dominating me. I still wasn't comfortable with having him seeing me naked or him touching my bare skin, but when I had replayed last times events in my mind after coming home from work yesterday I had gotten a really persistent hard on.
I heard someone come up behind me and turned to see Mitch carrying a basket. I greeted him and he greeted me. He took out my collar first and put it around my neck. Then he got a blanket out of the basket and laid it out. I could see he had some toys in the basket too, but he left them there and told me to unbutton my jeans but keep them on. Once I had done it he took a knife out of his pocket and told me to stay still.
"We're going to play a little game, slave", he said as he started making cuts in my t-shirt. He put the knife away and put his hands under my t-shirt, caressing my bare skin. "I'm going to rape you." His fingers were playing with my nipples now, making me blush and moan. "You're going to stand right here with your eyes closed and I'm going to come up behind you, wrestle you down on the blanket", he let is words die out. I knew what came next. He pulled me close, let his hands go around my body so they could squeeze my ass and whispered in my ear: "then I'm going to rape you. Again and again, until your ass is so sore and so filled with spunk it turns into a pussy."
I don't recall ever having blushed so bright red. I got butterflies in my stomach thinking about it as he moved away and told me to close my eyes. I took a few deep breaths to calm down. I wasn't planning on being an easy victim.
I screamed in surprise when I was pushed down on the blanket. I landed on my back with him on top of me. I tried to hit and kick him, but I wasn't really fighting for my life, just putting up a show. He slapped me across the face and wrestled me over on my stomach. I tried to get away, but he held me in place with a hand between my shoulder blades while sitting on my rear. He was twice as heavy as me so I really couldn't go anywhere when he was sitting on me. I felt him rip my t-shirt off and then holding the knife to my neck. I was told not to move. He quickly got my pants off.
He still had all his clothes on. His strong hands split my legs further apart and I screamed again. I felt him caressing me roughly while he told me again to be still if I wanted to live. Two fingers were pushed inside me hard. There was no lube on them so I screamed fearing he was going to fuck me raw. He ignored me and made my tight hole open up using his two fingers. I felt something being poured into my ass. Lube. Lot's of it. He got his fingers out and laid on top of me, positioning his fat dickhead at my virgin hole. His right hand guided his dick and his left covered my mouth. I was breathing heavily through my nose while I waited for that fatal thrust to come. He let me wait.
Then I felt the sharp pain as his dickhead breached the barrier. He started pumping right then and there with just the head in, slowly getting more inside me with hard thrusts. I screamed even though he had my mouth covered with his hand, the sound was muffled but the pain in my throat was telling me I was screaming loud. It hurt. I had tears in my eyes. He sat up halfway to get better leverage and really pounded into me. As he did so my screams became audible again. When I became quiet to catch my breath he told me he only had half his dick in me. To prove that point he pushed the rest inside. He lifted my hips from the ground and wiggled to really get every millimeter inside my tight ass.
With his monster dick still buried in my ass he lifted me to a doggy-style position and grabbed the back of my hair. He experimentally moved in and out a few times before he started slamming into me like I was nothing but a ragdoll. I was on my hands and knees getting thoroughly fucked by a dick that was bigger than any I had ever seen.
That's when my blood froze, because I saw another man standing a few feet away. Watching. Mitch had either not seen him or he didn't care.
Or he knew.
The pace changed, the thrusts got deeper and harder and more regular. I had to moan. I had to scream. I started moving my hips to make him go deeper. I felt a few hard slaps on my ass and I felt his dick swell inside me, making me wonder if that monster could really get any bigger. He slammed his dick as deep in as it could possibly go and came. It was like hot lava was being spewed into my bowels. He pulled me back so I was sitting on his dick. It didn't go limp.
The man I had seen had a wicked smile on his face. He made a comment about how pretty boys like me should be fucked on their backs, like girls. I blushed as my master caressed my inner thighs and played with my nipples. I was really close to coming, but I needed more.
Mitch pulled out and pushed me on my back. Before I could get up the other guy was on top of me and got his dick out of his pants. It wasn't as big as the one that had just taken me, but it was still big. He held my legs up and pushed his hard dick all the way in. He positioned himself on top of me and started fucking me like I was a girl. It didn't hurt as much so I was moaning in no time. My own dick was aching to come. I was writhing under him, but he came in me before I could come and he pulled out and got off me.
"Not enough?" my master asked me as I lay alone on the blanket. I shook my head. "Maybe you need more dick inside you then?" he said and got on top of me. He pushed his dick up my abused hole and fucked me slow. I moaned and moved my hips. His left hand played with my nipples, then his mouth started sucking on my left nipple. All the time he was slowly fucking me. Too slow. I was moaning like a bitch in heat and I was desperate to make him fuck me harder so I could come.
He stopped sucking on my nipple. It felt sore when his mouth left. "I'm going to pull out, get on your hands and knees." Hoping he would take me hard I did as soon as his dick was out. He got underneath me, pulled me down on him and kissed me. I felt a dick slide inside my sore ass, but I knew it couldn't be him. The angle was wrong. He ended the kiss and started pushing at my already filled hole.
Shit. They weren't really gonna do that, were they? I pleaded for them to not do it, but I just got chuckles in reply. The pain when both their dicks were inside me made me pass out for a second. As I came to I felt them starting to thrust.
"Such a slut. Fucked by two large cocks at the same time... I bet he likes it too", the strange man said.
"His little cock sure looks hard", my master replied with a chuckle. He was squeezing my ass and holding cheeks apart at the same time. Each time they would thrust into me I moaned. I hurt, but it felt good too.
"Listen to the slut, probably has the time of his life getting his ass split in two."
I was blushing again, because I couldn't stop moaning and I had no chance of getting away. My dick was being rubbed between my stomach and my master's stomach, and I was starting to moan louder and louder with each thrust of their dicks. When I hit my climax I clenched my ass muscles tight, which hurt like Hell, and both men moaned and came with me. When they pulled out and left me alone on the blanket I felt hot sperm trickle out of my sore hole. I tried to get up but it hurt so much I just lied down again.
The next time I met my master was two and a half weeks later. He had told me I needed to rest, and I hadn't complained about that. I had been really sore, but I hadn't bled anything so I thought I didn't need anything other than some sleep and maybe some ice...
I had bought a thong, which I was wearing under my jeans. When I stripped down my master told me to keep it on me. He put the collar around my neck and then made me crawl on all fours beside him as he walked around in the house and did some things. When he sat down in the couch to watch TV I curled up on the carpet by his feet and closed my eyes.