Things did not go back to normal after I was put into anal chastity. I grew to love the locked plug, as it wiggled around in my butt all day. It was just so comfortable to wear and kept me constantly horny. Sometimes, a little piece of my ass skin would get pinched between the lock and the base of the plug so I usually had a purple bruise on my right ass cheek on inside of my crack. This was a small price to pay, to be back in Elizabeth’s good graces.

The main problem was that Jake was struggling to unload in Elizabeth. He called me up one afternoon and in confidence told me that he just didn’t enjoy her pussy as much as my tight ass. He also said that he had just become kind of bored with Elizabeth. She was fat, and he was not that attracted to her. He told me that he was infatuated with me. He said I look as good as any girl. He loved fucking my tight ass, and I came without drama. I kept our conversation a secret, but Jake slowly came by less and less to please Elizabeth.

Within a few months, Elizabeth was letting me out of the cage, on an almost weekly basis, on Friday nights, since Jake was not coming over on Saturdays much. She never let me fuck her again. I was only allowed to stroke off into her thick bush and then lick it clean. I missed sex so much.

Our relationship dynamic also changed, Elizabeth just became so bossy and we were not spending as much time together. I still pleasured her to multiple orgasms every night with my mouth. We just didn’t make out and play together like we used to. Elizabeth started going out to bars alone and would sometimes come home, with an extra juicy cunt to clean. I enjoyed these nights. They were the only times when Elizabeth ever showed me any affection.

None of these men were interested in involving me and usually stopped seeing her when she told them about me. A couple came over, but were not comfortable with me around.

Almost a year later I ran into Jake while eating lunch. I was sitting alone eating at a bar and grill when he walked up, patted me on the back and said, “Hello.”

Unconsciously, I wiggled my plugged, panty covered ass, as he asked if he could eat with me. We were alone at the bar so we were able to talk freely. He asked about Elizabeth. I told him she was fine, without divulging anything personal. He let me know, that he had been dating other women, but that it was hard finding a good woman when you are sixty-one years old. He also said, that I was a better woman than anything out on the market. I knew he wanted me, by the way his eyes devoured my corseted midsection.

By the time we finished lunch and he paid for the bill, my panties were soaked with precum. I truly missed Jake.

The next few weeks were not good with Elizabeth. I was just feeling lonelier and hornier than ever. I don’t know why it took me so long, but five weeks, after we had lunch, I called Jake. I told him that I wanted to talk to him. We decided, to have lunch again, the next day.

I had butterflies in my stomach the whole rest of that day and the next morning. I was afraid Elizabeth would notice but she didn’t pay me much mind, except for when I ate her to four orgasms, while she watched some porn.

I unburdened my heart, to Jake at lunch, and told him what was going on. He listened and said that he was also living a lonely life. He was not able to find a woman that he loved, or wanted to live with. He told me that he would love to have me move in with him, but if I were to do so, I would have to be made-up, as a woman, at all times. He was just not attracted to me when I was my male self. I let him know, that I would love that. I now loved being feminine and submissive, and was wearing panties, under my male clothes right now.

The fact that I was wearing panties, turned Jake on.

“Let’s go out to my truck. It has tinted windows. I want to see your panties, and would love to get one of your famous blow-jobs!” Jake suggested, with excitement.

I agreed immediately. We finished eating fast. Jake paid for the meal, and I followed him out to his truck, where he got in the back seat. He was right, his windows were really dark, and you could not see in, unless you put your face right to the glass, with your hands over your eyes.

I followed Jake into the back of the truck.

“Let me see those panties, Baby.” Jake demanded, as soon as the door was shut.

I removed my shoes and slithered my pants off. This exposed the sheer, dark purple, satin panties, with black lace trim, that I was wearing.

“Get on your hands and knees, with your ass facing me.” Jake commanded.

I did and jake immediately started feeling my ass. I was smooth all over from the Nair cream and Jake love the feel of my skin.

Jake fondled my cock cage, and pulled on the lockable anal plug, giving me some nice movement, in my boi pussy.

“I can’t believe that you are wearing these all the time.” He stated, as he grabbed and fondled my ass cheeks, “I wish that plug wasn’t locked in, or I would fuck you right now!”

I felt so gurly at that point. I needed to get his cock into my mouth. I got down on the floor and opened his belt and fly. Jake pushed them down around his ankles as fast as he could. Once again, I was facing Jake’s big cock and I had it all to myself! I leaned in and took its head into my mouth and stroked it so gently with my tongue. Jake moaned and I knew I was where I was meant to be, on my knees pleasuring a real man.

He was musky and sweaty from work that morning and I loved it! I worked on his cock and large furry balls, like a woman possessed. Ten minutes later, he unloaded into my mouth and I swallowed his gift with relish. Oh, how I had missed this!

I told Jake I would talk with Elizabeth that evening and if the talk did not go well, I would like to try living with him.

He said that his house was waiting for me. Despite being in male clothing, he kissed me fiercely on the lips, and we both went back to work.

That evening, after I had licked Elizabeth to a bunch of orgasms, with no returned pleasure, I let her know that we needed to talk.

As I had done with Jake, during lunch, I let everything off my chest. I told her, that I did not feel loved by her anymore, that we didn’t do things together, like we used to, and that I missed having someone else give me orgasms.

Elizabeth told me that she lost respect for me as I became more and more feminine and submissive. “You are just a pussy boy now.” She stated.

“I have been keeping you around, because you bring me off so well every night, but I don’t have love for you anymore. You are just convenient.” She explained.

I was devastated. I told her that I would be moving out and asked her for the keys to my cage and plug.

“Fine!” Was all she said, as she removed the chain containing the keys, from around her neck and handed it to me. “I don’t want you sleeping in my bed anymore.”

I had given her my whole heart, and this was how she thought of me! I didn’t want to be in her bed anymore and slept on the sofa that night. The next morning, I loaded a large portion of my clothes into the trunk of my car and left for work. I called Jake and let him know that I would be moving in with him. He was so excited.

Work dragged on that day. I was a bottle of mixed emotions. The woman that I loved, thought nothing of me. The man I was so attracted to, was excited to have me move in with him. I knew that my life had changed drastically and I was scared.

When work was finally over, I drove to Jake’s house. I had never been to it before. It was a well-kept house in a solid blue class neighborhood. It had three bedrooms. Jake let me know, that I could take one of the bedrooms and make it into my dressing room, since he required me to always be dolled up for him. However, I was to sleep with him every night.

We carried my stuff into that room, which was empty, except for a large dresser, with an even larger mirror on top of it. Jake left me, to get dolled up. He closed the door as he left.

I spent forty minutes, removing my male clothing, showering, and dolling myself up. I wanted to be the best woman possible for Jake. I expertly made up my face and donned my wig. I put my tightest corset on, pulled up my thigh high stockings and attached them to the corset garter straps. I pulled my panties up over the garter straps and put on a sexy silky robe. I did not expect to be dressed for long! I also put on my highest heels. Five inch stilettoes. I loved them. When I wore them, my butt seemed to pop out so much more! In addition, they raised it so it would be easier for Jake to grab.

Jake did a double take when he saw me.

“You are gorgeous, Sweetheart!” He praised, in real admiration. “Such a hot, tight, young body! I am going to pop off in no time tonight.”

Jake grabbed me around the waste and kissed me passionately. I loved how powerful he was and how he owned my body. One strong arm held me firmly into his beer gut, while the other hand fondled my ass. Oh, how I loved it!

“What are we to do about these?” Jake asked, while yanking on my locked anal plug.

The feeling was quite nice. I wiggled my ass seductively in his hand and gave him the necklace.

“Daddy, you will be Keymaster now.” I told him in the most submissive, feminine voice.

“Oh, Sweetheart.” Jake soothed, “You don’t have to wear these anymore.”

I was so touched that he wanted to free me. Deep down, I yearned to be free, and to be able to play with my dicklett again. Yet, I knew it wasn’t right for me to be free. I had realized with Elizabeth, that I needed to be owned and controlled. It was how I was meant to live life, and I had accepted my fate and loved being owned.

I explained to Jake, how to much sexual release, decreased my drive and desire to pleasure. I told him how Elizabeth only let me out of the cage on Fridays. I also told him, that since I could now get sissygasms, when he fucked my ass, that it was no longer necessary to be released.

I also explained, that Elizabeth freed me from the lockable ass plug only in the mornings. I showed him the locked box, with the extra key, in case of an emergency and its coded disposable lock. I told him, that obviously he would have to release me, so I could poop, and so that he could fuck me, but otherwise I wanted him owning my pleasure hole.

“I get it Baby.” Jake said, with understanding. “Right now, I need to fuck that tight ass of yours, So I am unlocking it.”

I bent over and pulled my panties down to the back of my thighs. Holding my ass cheeks apart with my hands, I exposed the plugs base with its ring and lock. I explained to Jake that after he unlocked the plug, he could close the interior petals that prevented removal, by turning the ring.

I kept my smooth ass spread with my hands as Jake did so. Soon he had the plug out and inspected it closely. He turned the ring back and forth, admiring how the petals opened and closed.

“This is a great piece of engineering. I will inspect it a little more closely before I lock you up again. However right now, I need to pop that hot ass of yours.” Jake declared, as he gave me a loud spank on my right ass cheek.

I squealed in girly delight, as I popped up and dropped to my knees in front of him. I was dying to release his huge cock, and to get it in my mouth.

Jake pulled me up off my knees by my arm, and pointed towards the bed, saying, “No need for any fluffing tonight. I am already rock hard.”

I finished pulling off my panties, and climbed on the bed, wiggling my ass, towards my Daddy.

Jake stripped out of his clothes, grabbed a bottle of lube, and smacked my ass again. I loved it when he spanked me. It is just so gratifying feeling the hard slap of a palm on my ass. It shows the wanton lust of the person meting it out.

What shocked me was the touch of Daddy’s beard on my ass cheeks, and his tongue attacking my hole. I had never had my ass eaten before and this was divine. I squealed in delight, reached back, and pulled my cheeks apart, giving him easier access. I could get used to this!

Daddy ate my ass for a couple of minutes and I was panting with desire. He roughly kneaded my cheeks as he got up and opened the bottle of lube. I reached back and felt my caged cock. My fingers got coated in the sticky precum. I licked them off with relish as I felt some cold lube dripping into my crack. Daddy worked the lube into my hole with a thick finger. His finger, sawing in and out of my hungry hole, felt even better than his tongue and hinted at the pleasures to come. He then applied lube onto his cock.

I felt his slippery lubed hand grab my hip as the blunt head of his cock lined up with my unplugged pucker. His cockhead was so fat and velvety soft. Daddy just stood there and I started pushing back with need. I felt the pressure of that big head on my pucker, and rocked back a little more. The head popped in and I felt the sharp pain of intrusion. I clenched my sphincter around that big head and heard Daddy moan. I still remembered, how great it felt, to have my late Wife’s tight ass, gripping my cockhead. Those days were forever gone. Now it was my asshole’s duty, to give that same pleasure. I felt a sense of pride swell in my chest, knowing that I had become a beautiful, cock pleasurer.

The pain slowly faded and I started rocking back more. Daddy slapped my ass again and grabbed both of my hips and pulled me back. When he bottomed out, I felt that exquisite pressure on my prostate, and felt more precum ooze out of my caged dicklett. I let out a deep throaty moan, as the wave of pleasure and the feeling of fullness washed through my body.

Daddy pulled out now leaving only the head in my hole. The emptiness left a craving in my bowels, that was only alleviated, by the sweet friction of Daddy’s helmet rubbing back over my prostate, and the delicious friction of the shaft, on the walls of my pucker. My ass shuddered in intense pleasure, and my hole clamped down on the cockhead, lodged just inside my sphincter.

Daddy just held it there for a few seconds enjoying the tightness. I moaned in my yearning to be filled again. I felt a craving, so strong. I needed to be filled again. Daddy gripped my hips tighter and slowly pulled himself back into me. As his cock filled me, I breathed out with another throaty feminine moan. I felt his head, when it hit my prostate and travelled over it, giving me the most delicious pleasure. I felt Daddy’s hips push into my ass cheeks. I wiggled them, grinding back as hard as I could, while Daddy just held it in at its deepest. I luxuriated in the fullness. I thought to myself, this must be heaven.

Daddy Jake slowly started increasing the tempo. He sawed in and out of me. My prostate was going to get battered and bruised but I didn’t care. The friction and pounding were just too good. Sometimes, Daddy’s head would pop right out and then I got a little added pleasure of being stretched anew as he shoved that thick head back in.

This hard fucking went on for almost fifteen minutes before I had my sissygasm. I thrashed around on the bed, and squealed in gurly pleasure, my asshole clamping and unclamping, around Daddy’s cock. This set him off, and I could feel the increased warmth and wetness and he unloaded in me, and growled like a bear.

Daddy held his cock fully in me for another minute. He brutally pulled himself in by his powerful grip on my hips. They were going to be bruised and I would wear those marks with pride.

When we had both calmed down some, Daddy pulled out of my ass, with a loud plop, and fell onto the bed, next to me on his back.

“Clean me off Sweetheart.” He politely asked.

I looked at his slimy cock and really wanted to lovingly clean it off with my mouth. I just couldn’t bring myself to do it. It had been in my ass. My stomach churned at the thought of tasting shit, even though I craved that slime.

Thinking quick I picked up my panties and wiped his cock clean with them. This way, his seed would be on me. I put the now sticky panties, back on, over the garter straps. I enjoyed the wetness of his slime, that caused the panty material to stick to my skin. My own precum, and some of my seed also soaked into the material, making it stick to my scrotum. So slutty and so intimate.

I had made a mess on the bed cover. I quickly bent down, to suck my own seed, out of the cover. I wish it were Daddy’s seed but this would have to do. When I was done. I laid on top of Daddy’s broad chest and just enjoyed his warmth, as I felt his load, begin to ooze out of my wrecked hole, and create more of a mess in my panties. That sticky wetness was proof, of what a slut, I had just been. I savored it.

We both snoozed for half an hour. Then Jake woke up and showered. I did not shower. I wanted to enjoy my sticky panties. When jake came out of the shower, he brough the cleaned plug with him. He had me bend over and pulled down my panties. He then inserted the plug and locked it. I felt a sense of tranquility come over me, knowing that I was once again locked, and owned by my Daddy.

Jake sat down to watch the evening news and some sports shows, with a few beers. I just cuddled on the sofa, with my head on his lap. I loved how he lightly stroked my head and fondled my ass occasionally. I could get used to this life.