18 Yo Sissy Alone With Grandpa

*This is the continuation of a sissy boi with his grandparents*

It had been a few weeks since I had seen what grandma and grandpa do during their alone time. It had been a few weeks since I had seen grandpas big cock. There had been a lot of winks from grandpa and hints about sissies and what they should aspire to be more like. Grandma, still blissfully unaware, carried on like nothing had happened. Many nights, Jason could hear grunts and pants coming from the living room or bedroom at nights. But I did not come out to watch. He would stroke his little cock wishing it was him making the grunting and panting noises. Imagining himself imitating all the women in the nude magazines his grandpa used to show him, growing up.

It was a Wednesday night when grandma talked about a sudden trip to a lifelong friend of hers. In the daily life of grandma and grandpa, this was not out of the ordinary. She explained all the details, that tickets were already purchased, that she will be leaving tomorrow night, and that she would be gone for a week. Grandpa was smiling and encouraging her. She went into the bedroom and started to pack her clothes. While I sat with grandpa in the living room. He told me he has a surprise for me tomorrow night. Then he informed me that I would be taking grandmas place in bed while she was gone. I nodded in agreement and smiled at grandpa. i couldn't keep my eyes from drifting towards his groin. I could see it had stiffened in his pants.

"That's right. You'll get to see it up close tomorrow night." grandpa said

We took grandma to her flight Thursday night. Grandpa still had a business to run. But just like grandpa said, when we got back home from the airport that night. I slept in the spot normally occupied by grandma. That entire night Grandpa spooned and caressed me. I really began to enjoy the attention. Grandpas big hand softly and slowly rubbing me. I fell asleep to this. When the alarm went off, I woke up, fully embraced and tucked into grandpa. I could feel something just between my legs. Long, hard and very warm. Grandpa opened his eyes still holding me tight.

"I have a short day today" grandpa was saying as he began to rock his hips back and forth. Rubbing his hard cock between my butt cheeks. "We have some things that need to be done in the yard so we can have all weekend to play and explore what it means to be a sissyboi."

By this time grandpa was rubbing his cock faster and harder. Then he just stopped, got out of bed, and began getting ready for work. Before leaving he asked me to cut the grass, so they would have less to do when he got home. However, once grandpa was out the door. I quickly stroked myself to an orgasm thinking about where grandpa had his cock. I caught it all in my hand, something I had started to do during my masturbation sessions, then I licked my hands clean of all the cum. Sucking on each finger to ensure I had gotten every drop. Eating my own cum had made clean up afterwards, very easy. Once finished, I set out on the task of cutting the grass. Not only did I cut the grass, I trimmed the entire yard, gathered everything up in the burn pile, and did a few extra things that I could see needed to be done. Time was flying by and nearly all of the yard work was completed. Before I knew it, grandpa could be spotted coming down the road.

Grandpa drove down the drive way and parked his van in its normal spot. Exited the vehicle. Smiling and waving at me, as he always did. I came to him and told him all the things I had gotten done that day. Very excited. Grandpa wrapped one arm around me, picked me up, and held me so close our faces were only a couple inches apart. instinctively, I wrapped my legs around him.

"You've earned yourself an extra special reward for tonight" as he was saying this I could feel myself sliding down his waist. as if programmed I stopped once I could feel the unmistakable bulge of a hard cock nestled just beneath my own little balls. Then grandpa came in for a hard and rough kiss. Without thinking I just allowed it to happen and began to reciprocate the intensity. When grandpa released his lock on my lips. I could feel my heart pounding as I was panting from the sexual stimulation.

"We can save the rest for later, you hungry sissy. Come help me with a few things. I spent a few hours cleaning up around the house. When it started to get dark grandpa suggested we go inside and have something to eat, perhaps lay down in bed and watch some movies. I had no idea what was in store for me that night.

Grandpa cooked a small dinner for me. Suggesting how important it is to save room for desert. We ate while talking about the day. After I had finished my plate, grandpa then asked me the question that I was waiting for. "So, have you been thinking about my cock all day, sissy boi?"

I looked directly at his grandpas crotch again.

"I thought so. Would you like to see it again, sissy?" Cal asked, starting to rub his crotch through his pants.

"Yes, grandpa, I would like to see it again." I said in an almost girly voice.

Grandpa stood up from his chair and walked over to me. He leaned in to my ear and said very commandingly. "If sissy boi wants to see it again, he has to clean himself all over. But don't worry grandpa will help."

He put his hands around my waist. Helping me stand up from the dinner table. Without a thought, I let grandpa guide me through the living room and down the hallway. We went all the way to the master bedroom. There grandpa set me down on the bed.

"Before we can shower we have to lay out some clothes for you to wear." grandpa said while rummaging through grandmas underwear drawer.

After looking through the drawer for a few seconds. Grandpa finally settled on a pair of light pink panties with lace designs on them. They were very cute. At the time, I didn't notice that the back of the panties opened up to allow easy access to the asshole. He set them on the bed and went into a different drawer. This drawer was filled to the brim with stockings, pantyhose, and garter belts. Selecting a pair of black thigh high stocking with the seam running up the length of them. Then a black garter belt to ensure they stayed up my legs. Once those were selected, grandpa went into the walk-in closet. He didn't take long. When he came out he was holding a big box and a tight, light pink t-shirt. Cal set the box on the bed without a mention, then held out the t-shirt so the words 'Sissy Slut' in hot pink letters could be plainly read. "I got this shirt for you. I want you to wear it tonight for bed." he said while carefully laying everything out neatly on the bed.

Then grandpa extended his hand to me. I took his hand and was gently lifted up off the bed. Grandpa led me towards the bathroom, where he helped me remove all of my clothes. First my pants. Grandpa stared at my legs and said "You have very feminine legs. so smooth, it looks like we wont have to shave your legs. do you have hair anywhere, sissy?"

"No, I don't." I said in the same girlish voice.

Grandpa smiled and continued by removing my shirt. Staring at my near naked body with approving nods. Grandpa then walked behind me and began removing my underwear. As he removed my underwear, grandpa lowered himself level with his my ass. For a minute, I just stood there. Nervously naked in front of my grandfather. Then I felt his hands begin to caress my legs. They kept rising up my calves, then to my thighs. My breathing was quickening at this point. A sort of electric feeling began to cause my breathe to skip and stutter. Then grandpa ran his hands across my ass. "Its smooth just like a sissies pussy should be" grandpa said soft and seductively. I could feel him pushing my legs apart. Compliance is all I had in me. Grandpa begin tracing my asshole with a finger. Then he began to poke at my hole. Reflexively, I began bending further over at the waist. Then I felt grandpa's hand cup my soft, hairless balls. I moaned out loud at the barrage against my senses. He released my balls and put his hand around my cock. While still poking his finger in and out, deeper and deeper. He started to stroke my cocklette.

"Oh my god, it feels so good." I said in one breathe " I want more" I said in another.

Grandpa pulled his finger from my pussy. Focusing more on stroking my cocklette. I could feel a building urge coming from my balls. "After tonight, you will never be able to refer to this as a cock or penis or dick. After tonight, when we are alone, it is a clitty. Because sissies don't have cocks, they have clitties." speaking while stroking my clitty, he let it go when he was ready to put me in the shower.

"Look at your clitty, it's leaking." Grandpa said.

I look down and could see a string of clear fluid attached to the hole on my clitty.

"It's time to clean up this sissy pussy." He shoved his finger in my pussy one last time. But he added extra force and depth to it. My head shot up and backwards "Now get in the shower. We are gonna clean you inside and out." Cal said softly ushering me into the shower.

Once in the shower Cal brought a hose with a nozzle at the end. The nozzle was in the shape of the head of a cock. Grandpa attached one end to an extra spout on the shower wall. I always wondered what that was for. Grandpa told me he uses this for grandma's asshole. to clean her up before a huge anal pounding. Cal then bent me over and told me to try to relax and not to panic. Just then I could feel the head of the nozzle enter into my anus. I moaned and tried to adjust. But grandpa turned the warm water on and filled my rectum. I could feel my insides swell up. After a few seconds, he removed the nozzle. Telling me to hold it in as tight as I could. Then he let me empty my bowels over the toilet.

Grandpa was very experienced at giving enemas. He did it gently and with words of encouragement. "You are doing great. Once your asshole is clean, I am going to turn this into your pussy. I just know you are going to love it and beg for more"

Cal instructed me on the entire process so I could do this on my own later. Its very important that a sissy keep her pussy clean, especially if she going to get fucked. repeating the process of filling my rectum up and evacuating my bowels in the toilet. It started off dirty, but before long it turned clear. Throughout the entire process, I always had a steady stream of precum dribbling out of my cocklette. "I see a sissy who is enjoying this." grandpa said as he wiped the fluid off the head of my clitty and put it to my mouth.

Without any instruction or a thought, I opened my mouth and took his fingers in. I licked and sucked his fingers clean. After a few flushes, when I repositioned myself, I could feel grandpa playing with my pussy. he easily slid one finger in, then went for two. I could feel the change in pressure when two fingers went in and he went for a third. I started pushing back this time.

"I think we are finished with this, lets get the rest of you clean." he said putting away the enema nozzle and hose.

Grandpa joined me in the shower. He began to turn and twist me. Scrubbing everywhere. From head to toe. Looking for any unwanted hair. But I was hairless from my face, down to my toes. Every now and then, grandpa would put his face just an inch from mine. I started looking at grandpa's cock. I was watching it grow longer and thicker. Almost intentionally grandpa would turn me in a way so that his cock would rest between my ass checks. Wrapping his arms around me like I was a woman.

Once grandpa was sure that I was clean. He had me scrub his entire body.

I was only allowed to clean him. Our fun would come after. Once finished he instructed me to step out of the shower and that he would dry me off. I could feel that the ring around my anus was stretched open from the enema. Grandpa took a white fluffy towel and began to pat me dry. I was told to move this way and that. Then he told me to spread my leg and bend over. Grandpa started to dry my pussy. Patting it gently. Once dried, I could feel him squeezing both my checks. He began to lightly rub his finger tips up and down my thighs. Back to my ass. Then I felt him pull my cheeks away from each other. I could feel the air hitting my exposed asshole. And I liked it. That's when grandpa buried his face into my ass and began licking and probing my ass pussy. Tracing his tongue around the ring. It felt so good. Then I could feel the tongue force itself inside my pussy. Gasping with surprise from the sensations ive never felt, I yelled "Oh god. That feels so good"

Then the tongue fucking stopped. "Don't worry my beautiful sissy. With what I have planned for us tonight. Its going to feel even better."

Grandpa was completely naked. I was staring intently at his hard cock. He was correct, I have no reason to call my clitty a cock. Out of nowhere, grandpa took my hand and wrapped it around his cock. There was no shock in my actions. This is what I wanted. I lightly squeezed my hand, testing the thickness of it. It felt like holding soft, squishy wood.

"Come with me sissy" he said then he grandpa started walking.

I don't know why, but I never let go of his cock. I held on following him into the bedroom. He shuffled me around and sat me on the bed. I still had my hand around his cock. It felt safe. As long as I was holding this 10 inch cock in my hand, no harm will come to me. Only pleasure.

"It's time to get dressed sweet heart" he said to me.

I let go of his cock. Grandpa reached over and grabbed the stockings. he rolled one up, then lifted my left leg. He unrolled the stocking up my leg. Then the right leg. Once they were both on, he caressed my legs with his fingers. The sensation mixed with the fabric of the stockings was magnificent. Then he took the garter belt and placed it around my waist. He then commanded me to stand. Once up, he began to fasten the stockings to the garter belt. He had me spin around a few times, observing my legs in the stocking. Next he took the panties. One foot after the other he had me step into them. He brought them to rest around my hips and that's when I realized these panties had no back. My sissy pussy was completely exposed. Last he had me raise my arms over my head and he slip the light pink shirt over me. Once he was done, grandpa took a step back to see.

"Go into the closet and look at yourself in the mirror" he said with an approving tone.

I walked into the closet. The feel of the stockings on my legs, how the panties cradled my clitty. It was liberating. I turned to look at the mirror and the reflection looking back at me. I was speechless. I was entranced. I was in love. I looked like a typical slut, but I felt sexier than I could have ever imagined. I began to caress myself. I put a finger on my pussy. Feeling the lips around my asshole. I could tell my ring had been loosened. I wondered if it looked like grandma's. I played with my clitty through the panties. The feel of the fabric against my clitty was exquisite. I don't know how much time had passed but I heard grandpa say "Don't get lost in there sissy. We still have all night" snapping me back to where I was. Cause I was, in fact, lost.

When I walked out grandpa had opened the box. He was taking the contents out, one by one. On the bed he already had several realistic dildos of varying sizes. One in particular stood out. It was black with veins tracing the length of the shaft. It must've been over a foot long and thicker than my skinny sissy wrist. He pulled out a pair shackles, a leash, and a collar. Then came a pair of hot pink heels. They were strap heels, with a 4 inch spike. Each heel had one large band that could wrap around the ankle and fasten together, to secure the heel to the foot. He took both heels and brought them to my feet. He lifted the first leg and placed it on my foot. He let me put my foot down and started lifting the other leg. I had never worn heels before so my balance was not good. I put my hands on my grandpas back to support my self as he put the other heel on me. When he finished, I still had to continue to support my balance on him. He wrapped the strap around my ankle and fastened them. I was starting to get my balance in them when he reached back into the box and produced two little locks with keys. The straps had a buckle so that a lock could be put on to keep the heels on my feet until the locks were removed. I didn't care. I thought they were sexy.

Grandpa stood up and asked me to walk around the room. I did. I nearly fell over on the first few steps, but once I realized how to balance my self on them. I felt like a natural as I was starting to strut around. I could feel how they made my butt feel tighter

"I'm going to turn you into the sexiest sissy slut. Will you let grandpa turn you into a sissy slut?"

"Yes please turn me into a sexy sissy slut. I want to do what what grandma does for you" I replied in my best sissy voice.

Grandpa looked at me with a hungry smile "You are gonna do that and more" he said as he stood up.

I walked straight to him. He took me into his arms and we locked lips together. I was operating on pure animal instinct. He plunged his tongue into my mouth and I reciprocated. We made out like teenagers for dozens of minutes. His cock pressing hard against my panty clad clitty.

"Sit down on the bed sissy" grandpa said "we have much more to do. But first let me put on a video." he reached into the box and pulled out a DVD.

The DVD was a burned DVD. Not a store bought feature DVD. Grandpa placed the disk into the DVD player and pressed play. He walked to the bed side to retrieve the remote. After clicking through some menus, the video began playing. On the screen was a beautiful sissy whore. Dressed in all pink lingerie. She was well practiced at walking in heels. She walked into a room and the lights came on. It was a room full of naked men. The shortest cock in the room must've been eight inches in length. She turned and twirled. Striking poses that completely exposed her sissy pussy. That's when I noticed, the sissy in the video had something in her pussy. All I could see was that it was in the shape of a pink heart.

"mhmm!" grandpa coughed.

I turned to look at him and he was showing me what the heart was. "This is a butt plug. Sissies need to get used to the feeling of having their pussies filled. This is yours now. I want you to start using this often"

all I could say was "yes daddy." I don't know where the daddy part came from, but it felt right to say

He patted at the spot next to him. I came over and was beginning to sit down when he stopped. "No sissy. Bend over and put your hands on the bed."

"Yes daddy" again I said it. I don't know why.

As I was bending over, grandpa put the big bulb end of the buttplug at my mouth. I opened up and let him place it there. He then got up and walked behind me where he knelt. I could still see the video playing. Then I felt grandpas tongue licking my pussy again. There was no holding back this time. He was diving his tongue in and out of my pussy. He would spit on it, then push the spit into my anus. A couple minutes go by and as I'm looking between my legs I could see a wet spot forming in my panties. My clitty was leaking so hard. Then I felt a finger slide in. back and forth for a few minutes, then he added another finger. Once his two fingers could easily plunge in and out of my pussy. He took the plug out of my mouth. A string of saliva stretched from my mouth until it became to much and broke. He took the butt plug and traced the ring of my anus with it. Then I could feel it being pushed into to me. I braced myself. Then I felt the pop of it penetrating me and being sucked into position.

I moaned for minutes. I was starting to sound like grandma. "Oh fuck yes!"

Grandpa stood up behind me. He reached into the box again and pulled out a couple bottles and a few extra things. While still bent over grandpa put a hot pink collar around my neck. Then attached a leash to the collar. When he pulled it back, I stood up. He then attached some pink fluffy cuffs with heavy rings worked into the leather. The room was filled with hoots and hollers from the video.

"For the rest of the weekend. You will be leashed and collared. You will do what I say without question. You are now my sissy slut. I will dress you. You will wear those heels until I say otherwise. As long as you are in my presence, you will always have your pussy clean and plugged. Is that understood sissy?"

With the leash in his hand, I looked him straight in the eyes and said "I am your sissy slut, daddy. I will do what you say. I will wear what you want me to wear. I will always clean and plug my pussy." I wasn't even thinking anymore. I was just lost in the moment as I was repeating what grandpa had said.

Grandpa began leading me around the bedroom. He had me repeat over and over "I am a sissy slut. Sissy sluts need to get fucked."

I must've said it two dozen times, as I was paraded around the room.

"That's enough slut. Its time to taste grandpas dick" he sat down on the bed with his back on the pillows against the head board. "Crawl onto the bed sissy. Come over here and see a real cock"

I didn't hesitate. I crawled onto that bed. Feet still locked in heels. I crawled between his legs, right to his cock. I no longer needed instruction of what to do. I had the sissy in the video to emulate.

I laid next to his cock. Wrapped one hand around it, then the second. His dick was still longer than my both of my hands.

"Go on sissy. Taste the cock you will learn to worship. Lick it, suck it, let it fuck your mouth"

I did just that. I looked at the shaft. I kissed its head. I stroked him while sucking it. I was getting into a rhythm when I felt grandpa place his hand on the back of my head and start to gently push down. With my mouth wide open, I let him take control of me. He had me bobbing my head on his delicious dick. Every now and then, going deeper than the last time. I was making great progress. Sometimes he would go really deep and I would gag and cough. When I did he would tell me that I will get used it and eventually be able to take the full length down my throat. In the corner of my eye, I could see the sissy in the video take a cock, similar to my grandpas cock in size, all the way down her sissy throat. I wanted to be her. I wanted to be just like her. I wanted to be in a room surrounded by multiple large, long, thick, hard cocks.

I accepted the challenge. I put my arms around him and pulled myself onto his cock. I was determined to take the full length. But I would reach a point and begin coughing and retching.

"You are going to be a beautiful sissyboi." he said to me. Trying to comfort me through all the gagging.

The scene in the video had ended. Grandpa lifted my head off his cock, "Don't worry slut, we have all weekend to practice. Now its my turn." he stood up on the bed and picked me up. He laid me back down on my back and positioned me so I could watch the next scene in the video.

As it began to play, grandpa spread my legs and nestled himself between them. On the video there was another sissy boy. This time he was shackled with his hands behind his back and he was in some kind of device that suspended him in such a way that her head was held up and she was bent over. Pressed between her lips was something that kept her from closer her mouth. Drool was oozing out through the opening. The camera panned in closer so you could see her tongue darting in and out as she tried to swallow her spit.

Then I felt grandpas hand pull my panties to one side. Exposing my little five inch clitty. I was hard as a rock and leaking like a faucet. Grandpa wrapped one hand around it and it nearly disappeared. He started stroking me. I was moaning like a whore. Then I see the screen again. The camera had repositioned itself behind the sissy. You could tell her sissy pussy had been fucked non-stop. It had a natural gape to it that only comes from being fucked by enormously large cocks, constantly. The camera began to pan down to the sissies clitty. Only it was encased in some kind of pink cage. Grandpa had to be timing his strokes with the video. When the clit cage filled the large screen he began stroking my clit faster. I started squirming.

Grandpa started to explain what was on the sissies clitty, "That's a chastity cage. Really good sissies get to wear those. I have one just like that, for you. Maybe we can see if it fits you?" then I felt him lick my clitty.

Grandpa handed me the pink chastity cage. I stared at it. passing it between my hands. moaning in ecstasy. Grandpa stopped licking my clitty. with one hand he continued to stroke me. Then the other hand disappeared. I could feel a finger poking and prodding at the buttplug in my pussy. Then he began to push and pull on it to the same beat as his stroking. I had dropped the cage to grab the sheets. Grandpa's strokes were causing a pressure to build that I knew would end with a cataclysmic orgasm.

I shouted in the most girly voice I could "I'm going to cum."

Grandpa let go of the buttplug in pussy. Then grabbed my legs and lifted them over me. I was staring at my clit. I was watching grandpa's hand as he began to milk me like a cow to orgasm.

"Cum you sissy. Cum all over that sissy face. Mark yourself with your own sissy semen. You love this. Cum in your mouth." grandpa said. he was supporting my body over my face. With my clitty as close to my face as it could get. I could almost lick it. Maybe with practice, I can suck it.

Just like a good sissy, I exploded onto my face. my mouth was open and much of it landed on my tongue. grandpa milked my clit until every drop had landed in my mouth or on my face. I came so hard, so much. I just laid there with my eyes closed, covered in my own cum. With the load that landed in my mouth waiting for directions on what to do next.

Grandpa laid my legs back onto the bed. I laid obediently. i could feel the bed shift as grandpa crawled around on the bed. I could sense the he was beside me now. I opened my eyes to see his face above me. Then he came in for a kiss. There was an intensity to it. He locked his lips onto mine. His tongue pushed aggressively at my own. I was lost in a post orgasm glow. I could feel grandpas hand slide up and down my crotch. He was handling my clit and sliding his fingers in-between my ass cheeks.

I know he was drooling into my mouth. It mingled with the cum and completely filled my mouth. Once he knew my mouth was full, he released the lock he had on my lips.

"Swallow it all sissy" he commanded.

It took several attempts, but eventually I had swallowed it all. Once finished I opened my mouth to show him that I did what he commanded. I was so proud of myself. I could still fell grandpa's hand still rubbing my crotch and asspussy.

"Now make sure you get all that cum off you face and in your mouth. Grandpa has to finish getting you ready for your training. Your sissy pussy wont be able to take grandpa's fully erect cock the first time. I don't want to hurt my little sissy. So we are going to have to prepare it for my dick." I was listening to him while wiping my cum off my face with my fingers and sucking them clean. All while grandpa was shifting around the bed. He continued his speech "So tonight its going to be all about breaking in your sissy pussy. Tonight I'm going to make sure you will always be hungry for dick. Tonight, I'm am going to turn you into the cock hungry sissy slut you obviously are. Don't worry, grandpa's is going to take extra special care of his new sissy granddaughter. Just let him do what needs to be done"

I had finished cleaning off my face. I turned my gaze to grandpas cock as he was standing over me. There was a clear fluid drooling from his semi-erect cock. Then grandpa looked down at. "Yes grandpa, this is what I was meant to be. Teach me. Show me. I want more." I spoke to him while still shuddering from the rush of all the sexual excitement.

"Good sissy." grandpa said accepting the words of this pathetic sissy faggot, waiting to be turned into a cockwhore. But it's his pathetic sissy faggot grandson

Grandpa grabbed my left arm, stretching it toward one corner of the bed. He clipped a strap to it. taking away my ability to move it. Then stepping over me he did the same to my other arm. Once my arms were secured and tightened into place. Grandpa walked down and off the bed. He picked up the chastity cage I had dropped. Then walked around to the foot of the bed. I watched him, mesmerized by his every action. The video on the TV had changed scenes. This time it showed a heavily lingered sissy with artificially thick lips covered in pink lip stick, she had huge breasts, and the expression on her face was completely blank. The Scene looked like some kind of dungeon and she was strapped to a device that kept her immobile and bent over. As I was watching the scene unfold. Grandpa had been attaching my new pink chastity cage to my clit. Once again just like the one on this bound sissy slut.

I quit watching the movie again. My attention was now on my clitty as I watched grandpa install this strange apparatus. I was completely naïve and had no idea what this device was used for. But that sissy slut in the video didn't mind, why should I. Once grandpa had the cage in place he produced another lock. Clicking it in place, he tucked my caged clitty back in to my new panties. Grandpa's eye were locked onto mine. He could see the sexual excitement I was getting from all of this. He watched as my eyes would go from the video of the sissy and back at my locked clitty.

"I cant wait to hear you moan in frustration you sweet sissy girl. You may suffer some discomfort at first. but the reward for wearing it will more than make up for it." as he was talking he was lifting my legs over me again.

I don't know how I could've missed the straps coming from the head board of the bed after all these years, but before I knew it. He had my legs suspended over me. My sissy pussy completely exposed. He started tapping the buttplug and playing with it. I would moan and squirm. It was the most pleasurable torture ever. He would tug on it and let it go just before it could come out. It would quickly get sucked back in and he would pull on it again. Repeating this over and over again. Constantly I could hear the moans of the sissies on the video. Proclaiming how she wanted to be fucked by great big dicks, at great lengths of time, over, and over again. Then without warning he pulled the plug completely out. Before I could beg him to put it back in, he pushed it back into my asspussy. Then he would pull it out. Then back again. The intense pleasure of being fucked by this buttplug was something I never wanted to end. After a few minutes of this, he pushed the buttplug back in and turned to grab something. I couldn't see anything he was. My only view was my little clitty as it was locked away in the pink chastity cage.

We he turned back to face me, he was wearing a comforting smile, "This may hurt a little bit. I'm gonna use a lot of tube and take it slowly. Just tell me when you let me know when you begin to enjoy it." and with that being said he plugged to buttplug out hard and fast.

I let out a huge gasp. I could feel the air conditioned air hit my hole and before I could register anything he began to replace it with something larger. With slow and practiced hands he slowly and gently would push it in until I started to wince and then he would withdraw it. Then he begin to push it back in slowly. this time a little deeper. I don't know how long the phallic device was that he was stretching my pussy with. But the process went on. It wasn't too long before I started to moan as he would push it in deeper and deeper.

"Are you enjoying this?"

"fuck yes!" my instant reply

"Good. Its time to step it up" He said as he began to quicken his pace.

My moans become faster and louder. His pace started off slowly but would pick up pace. He was driving that phallic device in and out, in and out, in and out, with such a pace that I couldn't think breathe or even register that he had pulled it out of my pussy. With my mouth open, tongue out and my eyes rolled behind my eyelids. He placed the dildo he had been fucking me with in my mouth and took a larger one and repeated this process in nearly the same fashion. Only this time he didn't take it slow or easy. This one was considerably larger than the last and even though it did hurt, I wanted him to continue. I would moan loudly through the dildo in my mouth. For minutes or possibly hours, I didn't care, he fucked me with this larger dildo. then took the one out of my mouth and ask me what I want.

"I want to get fucked by large cocks!" I screamed in-between moaning. "Oh god it feels so fucking good!"

He then yanked the dildo out of me and forcefully shoved it back in. I couldn't moan, only gasp, as this large dildo penetrated deep inside of me. Time didn't exist. Only this pleasure. Only the feeling of emptiness then fullness.

"I fucking need cock!" I proclaimed. Then felt something hit my face. I hadn't been paying any attention to my own clit. But it had been leaking throughout all of this. This wetness I felt was my first sissygasm and certainly not my last.

I licked at my lips. Trying desperately to taste it. But the fucking continued. Normally I would come and a sleepiness would envelope me. But not this time. Instead, I was bucking my hips at the dildo. A pathetic display of a bound sissy faggot trying with all of his sissy strength to get more.

"You really are loving this, aren't you sissy?" He asked.

I couldn't respond with words, only actions. Then he yanked out the dildo one last time. I continued bucking the air. Oblivious to the fact that he hadn't put the dildo back in. He stepped away from my sissy pussy. As the bed moved I opened my eyes and could see him return with an eight inch long dildo that was easily 2 inches thick.

"Fuck my fucking pussy. Stretch it open. Please shove it in!" I exclaimed

He knelt back down at my pussy and spoke. "As you wish my little sissy boi."

With that he drove that thick long dildo back into me. After only one thrust I squirted my sissy load again, all over my face. The only words I could say anymore were "more." I had fully given in to this new aspect of life. I would never turn back. This is who I am now. Grandpa kept pounded my pussy. My clitty drooling and squirting over and over again. As grandpa fucked my boipussy he would wipe all of my squirts up and into my mouth. Where I greedily sucked and slurped all my cum. I didn't need direction at this point. I was completely lost in my new role. Sucking, slurping, swallowing, and getting fucked.

That was when grandpa pulled this large dildo out of my pussy. He stood over me, showing this large dildo in comparison with his on cock. There was a noticeable difference between the two. Grandpas cock was still longer and thicker. He wiggled his hips to make his cock swing back and forth.

"I want you to know I had always hoped for this from you. Your sexy legs, your thick ass and you feminine body. I had hoped this was the real you underneath it all. I want you to beg me to fuck your sissy pussy. I want you to tell me what you need and where you want it." he said to me as he flung the dildo to the side of the bed.

"Please, please. Grandpa I want you to take your cock and shove it in my sissy pussy. You are right, this is who I really am. I'm a sissy that needs to be fucked and feminized. I need your cock in my sissy pussy so bad! Please, shove it in me." I said in the most feminine and desperate voice I could muster up.

I stared at his cock and then his eyes. Back and forth. I saw as he knelt down and rest his huge cock at my probably gaping ass pussy. He rested the cock at my rosebud. Teasing my hole. Making me beg for it.

And I did. I begged him for his cock. I told him how much I needed this. That I will always be his sissy slut. just please fuck me with that cock.

After he felt he had teased me enough. He drove that cock right in.

"Oh God! Its so fucking big!" I yelled out loud

Then he started to fuck me. He was thoroughly enjoying the events that were transpiring. I was leaking all over myself. Just a steady stream of my sissy juices were leaking from my pink chastity cage. Gasps, moans and proclamations of needing more.

He fucked me for thirty minutes straight. I could barely hear the video anymore. Completely drowned out by his powerful fucking and my desperate pleas to get fucked harder. Then he pulled out and stood over, jerking his enormous cock. My eyes locked on to this powerful tool of lust. I knew what was cumming and I wanted.

"Shoot your load all over me. Cover me in your cum. Make me your sissy faggot slut slave!" I said as seductively as I could.

Without a thought he blew his load on my face, in my mouth, and all over my chest. It was a far bigger load than anything ive ever produced. I loved every moment. When he was finished he unbuckled my legs and then my hands. My body collapsed onto the bed in exhaustion. With all the tenderness he had for me he positioned me onto my stomach on the bed, tied the leash onto the headboard, and pulled my hips up into the air. Grandpa was still hard for me and he wanted more.

Plunging his dick back into my pussy he was telling me that this is what i was always meant to be. A cock puppet. A sissy faggot who will crave cock all the time now. There is no escaping this pleasure. Just embrace it and bloom into the sissy gurl you know you are.

I could hear every word as it sunk into my brain. I let him fuck me to multiple sissygasms. My voice was gone. My manhood was gone. All that was left was a sissy cock receptacle.

I don't know how long he pounded me into sissyhood. But he came in my pussy and shoved a much larger plug in. I was absolutely spent. I wasn't squirting anymore. I was just having dry orgasms over and over again.

He then unlocked my heels and slipped them off my feel. He took me in his arms as we lay in bed. My pussy plugged and filled with his cum. My face covered in his drying semen. This is where I wanted to be. Dressed as a slutty sissy whore. Covered and filled with cum. As I drifted off to sleep grandpa kept whispering in my ear how great I was and how the weekend has only started and that there will be much, much more.

All I have to do is ask. Then the exhaustion finally took me and I passed out.