Chapter 5 - You have to beg

It’s been two weeks since my wife of several years informed me that she was leaving me for another man. Todd. 

She had offered me to stay a part of the relationship if I agreed to her terms, including (among other things I was to learn) being obedient to her will at all times and being a fool in love, without giving it a second thought, I agreed.

We had gone out dancing tonight, we had a lot of fun, and quite a few drinks. We had met Mike and Andrew, a couple of sweet guys while there. I had been ordered to have fun with Andrew and my wife did the same with Mike. 

When it was time to leave, my wife had invited them both to continue the party at our house. They happily agreed and we killed two bottles of champagne, while hanging out and listening to music. I had then been ordered to give Mike and my wife the living room, and Andrew and I had made our way upstairs to the bedroom, door closed behind us.

Andrew was taller then me by almost a foot, had long brown hair pulled into a neat man bun. He was muscular and had a goatee that hung from his chin seven or eight inches. He was I had to say pretty attractive for a man. He had told me earlier that night that he was bisexual, and his partner of many years had left him about a year ago. He had been single since then.

Without warning, Andrew had practically tackled me to the door, I tried to fight back but knew he was much bigger and stronger then I was. He pinned my wrists together high above me, with only one hand. He had me practically on my tiptoes, and there was nothing I could do about it. I was terrified and the alarms came back to life in my mind. Removing the champagne bottle I had just emptied from my hands, he set it on a shelf to the right of the doorway.

Heart racing, and still a little shook up, I tried to calm myself. Thinking about the actions that were transpiring as he looked deep into my eyes. He had such pretty eyes, I thought again. The alarms began to fade as I realized that though his actions were rough and forceful, his eyes were filled with desire, and not malice. And he was smiling ear to ear. 

He swooped down and quickly sealed his lips to mine, and began to makeout with me hungrily and passionately. 

Stars exploded in my head, and my dick got so hard I was certain the plastic cock cage would crack. Finally unable to hold his breath any longer, he pulled away slightly, gasping for air, I giggled and he smirked. I was glad he was pinning me against the door, as the room was now spinning, I probably would have lost my balance. Again his lips captured mine and my mind went numb. Maybe it was the alcohol talking, but this man was a better kisser then any woman I had ever been with. And I willingly opened my mouth further to his hot, probing tongue.

I could tell his cock was large and hard, as it pressed against my stomach, his pants barely containing it. I would have normally been mortified, but my cock was hard and throbbing, aching to be free of it’s cage. I don’t know why but I had the urge to suck it, it definately felt bigger then the dildo my wife had fucked my face with earlier in the day.

The key to my chastity hung from his wrist and I realized then, I was completely at his mercy for tonight. I made up my mind that it was fine by me, he had been a perfect gentleman all night, up until this point. After what seemed like an eternity, he pulled away again, and I was lost in his eyes once more. He let go of my arms and I wrapped them around his waist, pushing him gently towards the bed, he let me push him into a sitting position on the bed.

He chuckled and I pushed him back to lie down on the bed. 

I sank slowly to my knees in front of him and decided I would do for him all of the things my wife used to do for me. Reaching forward, I unbuttoned his pants, and slowly pulled down the zipper. His cock was huge, barely being contained by the silky fabric of his bright blue briefs. He lifted his hips and I slid his pants slowly down to his ankles. His legs I noticed were as hairy as mine had once been, I didn’t mind. 

Knowing it used to drive me crazy, I began to kiss up and down the length of it through the thin fabric. He shivered and shook and I could tell he was enjoying it. Finally I hooked both hands into the waistbands at his hips, and he once more lifted himself to allow me to pull them to his ankles too. His hard cock sprang out nearly smacking me in the face, no longer restrained.

I had never had a cock in my face before and this was entirely new for me. It was thick and veiny, and just as thick as Todd’s cock, but thankfully closer to nine inches than eleven. Throbbing veins trailed this way and that and his mushroom shaped head was a deep shade of crimson. Precum dripped from the tip and without a thought I licked it clean. It tasted sweet and salty. He groaned with pleasure and his hands gripped the covers. 

I couldn’t help but giggle, I had barely touched it yet and had him like this. Though, I remembered, he had been single for about a year. I couldn’t believe myself, but I ran my tongue up from the base of his bulging manhood, slowly up to the top. He groaned again and was clearly trying to keep his hips still, though I knew he would rather be fucking my face. 

I was enjoying teasing him and did it once more, this time when I reached the head, I sucked it into my mouth. I sealed my lips around him, tongue outstretched like my wife had taught me. I then began to swirl his hard cock head around my mouth gently. He groaned louder and told me I was doing great. 

His hips were wiggling back and forth, and I knew before long he would lose control. Finally I descended, careful to keep my lips covering my teeth, slowly I sucked four inches of his throbbing cock into my mouth. I tried to go deeper but my gag reflex wouldn’t allow it. He didn’t seem to mind, and I pulled slowly off until just his head was in my mouth again. Swirling it around again, before descending once more.

His breath had become short and ragged, his groans becoming more frequent as I built up to a steady rhythm. His hips were beginning to buck around wildly, and I knew was quickly losing control. That’s exactly  what I wanted, I thought, I want him to fuck my face with wild abandon.

After several minutes of this I tried again to take more of his hard cock and found I could now take closer to seven inches of his cock deep into my throat without my gag reflex bothering me. His groans turned to moans of pleasure as I was now rapidly pumping seven inches of his cock in and out. I reached forwards and began to play with his balls with both hands, not slowing my pace on his cock.

He lost it. He sat up and both his hands moved to the back of my head. He began fucking my throat hard, pushing deeper every time. I felt like a pretty little cockslut, and that’s exactly how I looked too, I was sure. But to be frank I was beyond caring. I was having a blast.

At this point my nose was rubbing his pubic bone on every thrust, and I had started to moan around his cock myself. My cock cage still held tight, though I was sure at any moment it would burst. Finally he exploded down my throat and moaned loudly as his cock emptied what felt like gallons of semen into me. I did my best to swallow us much of the sweet and salty liquid as I could, but still quite a bit dripped down my chin. 

He pulled back, removing his cock from my head with a dazed look on his face. His hands dropped to his sides and he laid back, panting softly. Eagerly I smoothed all of the semen I spilled into my mouth. Sucking the delicious liquid off my fingers. It was my first time, I told him. How did I do Sir? I asked, biting me lip and eager for his review.

That. Was. Amazing. He gasped, and I turned red, giggling. He sat back up and regarded me with a wicked grin. I was beyond excited to see what he wanted to do next. He jingled the chain he had wrapped several times around his wrist in my face. Leaning forward he again kissed me deeply. After, he told me to go lay down on the bed on my back. I did so, replying sexily with, yes Sir. He grinned ear to ear and asked, do you have any rope? An innocent look on his face. I told him the top right drawer was where we kept all the sex stuff. He grinned and told me to remove my panties, I did so, replying yes Sir. 

That’s a good girl, he said, now reach for the corners of the bed with your hands and feet. 

I did so and he quickly returned with a spool of the pink nylon rope and a pair of scissors. He began measuring four lengths of rope and then set about expertly tying me down to all four feet of the bed. When he finished, I could barely even wiggle. I thought vaguely that I should be concerned, after all a man I had just met tonight now had me tied to my bed, spread eagle, and completely helpless. I wasn’t at all concerned to be completely honest, and the fact that he was a guy didn’t bother me anymore.

I was so horny, and my heart swelled when he began unwrapping the chain around his wrist. He fitted the key to the small gold lock and unlocked it. He unclamped it and it sprung open with a snap. He finished pulling it off, and then sat back to admire his prize. I was fully erect in a split second. My cock raged and was red all over and sensitive to the touch. Fully erect, it stood just barely six inches straight up. He giggled and sat between my outspread thighs. 

So, he began, playing around gently with my balls, I did hear your wife tell me that you were to obey my every command, isn’t that right Annabelle? Yes sir, I replied. My brain fogging as he continued to play around with my swollen balls, careful it seemed not to touch my cock. In growing need I tried without success to lift my hips and get him to touch my throbbing cock. 

Sit still, he ordered curtly. I complied immediately, and he chuckled. You sure are a good obedient girl. The words coming from this stranger were almost as nice as them coming from my wife and a giant smile filled my face.

So here’s the deal, he began, I intend to torment you until I have you begging for release. You will obey my every request, and if I approve of your performance, I may be inclined to help you with your little problem.  Immediately I replied, yes Sir, once more. A shit eating grin lit up his face and I wondered once more what I had gotten myself into. Either way though, my cock was free for now, and I might just be able to earn satisfaction tonight if I played my cards right.

I was filled with glee when he moved over me, placing a knee on either side of my head. His cock was fully hard again, and the head sat against my lips. I knew what to do without being told, and opened my mouth wide. I sat there lips folded over my teeth and tongue out like a cumslut. He said, Annabelle you sure do know how to please a man. I began to giggle.

My giggle was cut short as he pushed forward, the first six inches of his throbbing erection filling my throat. He paused there, making eye contact.

You are loving every moment of this aren’t you Annabelle? He said teasingly. I tried to  respond but after the third time of trying to say yes Sir around his massive cock, I gave up. I settled for shaking my head vigorously up and down.

His eyes rolled and his head fell back at that. I sped up at his reaction, waving my head around like a moron. He however had begun moaning softly, and I knew I was doing the right thing. After a few moments, he lifted his head back up, eyes capturing mine.

A fire burned in his eyes of pure desire, he put both hands on the wooden headboard and began to fuck my face hard and deep. He was burying his entire cock to the hilt into my throat on every thrust, gaining speed on each stroke. I was starting to moan myself, around the cock filling my throat, I felt like a total slut. It felt absolutely wonderful to be used like this, and I felt that I needed to taste his salty sweet semen coat my mouth once more.

It seemed I would have to wait a while longer for that, as after about five minutes of this brutal face fucking, he pulled out. Though he still hadn’t come. I sighed in disappointment and he laughed. I have other plans, he explained, and I replied, Yes Sir. Eagerly awaiting his next request. 

Finally removing his dress shirt, and his boxers I got to admire his fully nude form. He was tanned from the waist up, and from the knees down, clearly he spent plenty of time outside in only shorts. He was muscular all over and hairy. Finished undressing, he sat next to me. Then he leaned over, resting his head head on my thigh.

I shivered at the closeness, I felt like hugging him, but tied as I was, I could do nothing. Leaning further over, he sucked my head into his mouth, swirled it around thoughtfully for a moment, and then spit it out. The action made stars explode once more in my head, and my brain stopped working.

He giggled and looked at me with an impish smirk. How much do you want it, he asked. So much Sir, I want to cum so badly, I whined. He laid his head down, so closely to my cock I could feel the warmth of his breath. Well, he started, you’ll have to beg. I understand, he continued, you have been being taught how to be an obedient cumslut princess, and you have preformed well so far, but I need to hear you beg.

I felt like a dirty slut, but I didn’t care. I begged and begged for him to give me the release I so craved. At this moment I would do anything to come, and I told him so.

He didn’t listen. He told me I had been a naughty girl and I would get to come when he was ready for me to, and not a moment sooner. I groaned, and began to beg once more, desperate for release. He only laughed. He leaned forward once more and gave my head a gentle kiss before hopping up. I groaned in disappointment.

He began to untie me and told me I was not to touch myself. Once my arms and legs were free, he told me to roll over onto my knees, face down and put my hands behind my back. I was becoming an obedient little slave and I quickly did so, my yes, Yes Sir coming out instinctively. I felt the handcuffs from earlier click into place around my wrists and knew I was once more helplessly bound to his will. I loved it.

The metal butt plug had been in my ass for hours and I had practically forgotten it was there until he swirled his finger around it. Stars began to fill my vision once more. He pulled on it gently, and my cock throbbed harder. It didn’t hurt until he began to pull it out, but after a moment or two, the pain faded, and it popped out easily.

With the plug removed, I realized how empty I now felt, and wished he would put it back. I heard the squirt of the bottle of lube and my mind raced in excitement of what I knew was next. You want my cock don’t you Annabelle? You long for me to fill you completely and use you as the sissy slave you are I bet? I replied, yes Sir, oh please Sir, please fill me with your giant dick Sir, I need it!

Not being able to refuse such an offer, he positioned himself between my legs, and gently pushed his head into my virgin ass.

He met little resistance and the plug had done a great job of preparing my tender little asshole. He sat there for a moment, rubbing my back and giving me time to adjust to the size. I had to have more, and pushed back, desperately trying to get more of it inside me. He felt like fire, and my mind fogged, all I could think of was getting pounded by his throbbing hard dick. My desire to satisfy my own erection gone, I thought only of having his cum fill my asshole.

After what seemed like forever, he began to slowly push further, easing his hard cock inch by inch into my willing ass. He stopped at six inches and for a moment I was filled with sadness, I wanted so badly for him to bury himself inside me. I felt so full, but knew I could take his full length. As he began to slide out, I groaned in ecstasy, quicker then the first time, he slid back into my well lubed butt. Drawing moans from my lips. He went deeper this time, less then an inch from having the whole thing inside me.

I felt amazing, but I wanted more. Please, I begged, please Sir, use me, fill me to bursting and pour your seed into me. Without any further hesitation, he pulled out to the head, and then buried himself to the hilt in my tight asshole, then without pause, pulled out and pumped into me harder. He began to thrust faster, building up a steady rhythm and bottoming out on every thrust.

Stars filled my vision and pleasure raced through my veins, I was now moaning like a filthy slut, begging him between moans to go faster and stop taking it easy on me. He obliged and began to fuck me roughly, his balls slapping into mine deliciously. 

I had lost all sense of time, but I was sure he had fucked me for at least an hour. To my disappointment, he smashed into me one last time and let out a mighty groan. My mind went numb as I felt his seed explode deep into my ass. It felt like molten lava, and as he slowly pulled out, I could feel it begin to drip from my gaping asshole.

He gently reinserted the butt plug, and the precious liquid was stuck in my stretched ass. He told me to roll over onto my back, and I managed to with some difficulty, wrists still trapped by the handcuffs. My cock quivered with need and I lay there hoping he would give me the release I desperately needed. 

The blowjob he gave me next, was by far the best one I had ever received. He was gentle and giving, in minutes he had me riding the edge, about to explode. He sped up his pace, making eye contact, I squirmed and moaned like a banshee, his efforts finally pushing me into an earth shaking orgasm. Pleasure exploded from every corner of my body. 

Quivering still in the after glow of the intense orgasm, he snuggled up next to me, his head laying on my chest and within moments we had both passed out cold.

The first thing I noticed in the morning was the sunlight warming my skin. It felt wonderful and as I opened my eyes, they beheld a sight I couldn’t explain, confusion swelling in my mind, alarms going off in my head, I frantically tried to stay calm.

Continued in My new life as a sissy, Chapter. 6 - Filling my new role