Chapter. 3 - A whole new me

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.

I followed her up the stairs, in love with the way her ass was outlined in that gorgeous sun dress. She wanted to show off all of the new clothes and stuff we picked out together. A fashion show, how sexy. 

We rounded the top of the stairs and I couldn’t help but give her ass a playful smack. She giggled as she opened the door and we both stepped in to sit on the bed, the bags from our earlier shopping trip covering most of it, we both sat down on the bed.

What should we try on first she asked? I told her to pick. She reached over to the bag of lingerie and said I should try them on for her, since I was already wearing a pair of her panties. I was disappointed but agreed.

She handed me the pink panties that said pretty princess across the crotch and told me these ones, and take off those clothes silly. I stripped down to nothing and slid the new panties up my legs, pulling them into place around my hips.

They felt amazing, rubbing in all the right places. She pulled out the lacey pink garter belt and stockings set and handed me these next, saying these too. I slowly pulled each sheer hot pink stocking up my smooth freshly waxed legs and that felt really nice too. Next I fixed the garter belt to my waist and snapped the clips onto the stocking to hold them up. 

She squealed happily and said you look so sexy sweetie. I laughed and made to start removing the outfit and she stopped me, handing me a pink dress that had an attached miniskirt and was made of a smooth satiny fabric. This one matches well I think, put it on, she said.

I groaned but pulled it over my head anyways, the chest was tight but stretchy, the fabric meant to have breasts pop out in it. I however had no breasts, so it just clung to my chest and felt amazing. I turned around and she tied the straps behind my neck and zipped up the back. Even tighter now, but it still felt so wonderful, it all felt so wonderful. The dress barely covered my panties and I got hard just thinking about her wearing this out in public.

She noticed and giggled, you seem to be enjoying yourself. I nodded and made to start removing the outfit to try the next one and again she stopped me, telling me to spin around a few times so she could see. I did my best version of a pirouette and she laughed, the wind on my skin made me shiver in excitement. She pointed to the chair by the desk. Sit down sexy, she said. 

I did so and she walked up beside me, caressing my shoulders and then my chest before gently pulling my hands behind me, my eyes rolled at the sensations she was causing and my dick throbbed with desire. My eyes snapped open at the sound of handcuffs clicking into place on both my wrists. I jiggled my hands only to find they were securely fastened to the back of the chair. 

I looked at my wife, eyebrow raised in question and she said nothing. 

Reaching forward, she pulled the front of the panties down under my balls, my cock springing free, hard and ready. This won’t do she said frowning and began to strip off her sun dress and removed her lacey black panties. Again my jaw fell, she was completely smooth too, freshly waxed just like I had been this morning.

her pussy was free of hair and dripping already. My cock got even harder. She giggled and her perky tits jiggled at the motion. You are drooling sweetie she said, and climbed onto me. Her steaming pussy mere inches from raging hard on, again my mind went numb. 

She hadn’t had sex with me in months and I couldn’t contain my desire. I bucked my hips up and the head of my cock plunged into her slick pussy for a brief second before pulling back out. She let out a gentle moan and slowly started lowered herself onto my cock, inch by agonizing inch. Finally she sat down fully on my lap, burying my cock into her hot wet pussy. She kissed me like she hadn’t in ages, tongue eagerly ravaging my mouth. She lifted her self up until just my head was inside her and then dropped, letting out another gentle moan. 

She did this a few more times and already I was panting like a dog. Before long I was on the edge of a tremendous orgasm. I told her so, and she  pulled off. Standing up and then moving to her knees. She began to suck my cock and her mouth felt even better then her pussy, and she was an expert at blowjobs. Within seconds I shot my load into the back of her throat, letting out a satisfied groan.

She laughed and said that’s all? That wasn’t more then five minutes love. I blushed deeply again and hung my head down. That’s ok she said, that’s why I have Todd. Again she disappeared behind me rummaging around in her dresser.

We had dabbled in bondage quite a bit when we were still together, and when she returned I recognized a leather blindfold and a pair of leather thigh cuffs both attached to a two or three foot pink nylon rope. I had many fond memories of using these pleasure implements on her, and now it would seem they would be used on me. She strapped the first thigh cuff to my thigh right above the knee and then did the same with the other. Moving back behind me she looped the ropes both through the center of the chair back and started to pull them tight. 

My legs were pulled up to my chest, knees bent, and was completely immobile now that she had tied the ropes off. I could see the bed from here and saw her start to pull out several of the sex toys and bondage instruments we had used in the past and arrange the neatly. She had dildos, nipple clamps, several vibrators and also an assortment of anal plugs in different sizes laid out. She had been out of sight for a while when the blind fold was lowered over my eyes and everything went dark. I was quite concerned and was about to say something when she affixed my favorite gag to my face, fastening the strap behind my head. 

The gag had a thick ball that went inside my mouth, attached to the other side was a squeeze pump that expanded the ball to fill your mouth. It was a quite effective way of silencing my objections.

You always did like using this gag on me didn’t you hunny, your turn. She began inflating it until my jaw couldn’t open any further and then a few more times to make sure it was tight and my mouth was completely full. 

Feels nice doesn’t it sweetie? I shook my head no several times, unable to speak and she let out an evil sounding laugh. Well too bad, I have a lot things to say and do to you today and I don’t need your silly opinions getting in the way my pretty princess. I realized those words were also printed on the panties I had picked out for her, the ones I was currently wearing.

I felt what could only be a nipple pump slowly tugging on my nipple, tighter and tighter, then it clicked in place and I groaned as I felt the pump descend on my other nipple, pump pump pump pump click. I groaned as the tugging sensations turned to pain and she giggled. 

I heard the snap of a pair of latex gloves being pulled on to my wife’s hands and then a loud click followed by a squirt. I squirmed when I began to feel her massaging my asshole the lube cold and awkward, but my cock had a mind of its own and was fully erect once more. The sensations stopped and I groaned through the gag, I knew a butt plug or toy of some sort must be next. 

She started pressing a dildo about the size of my thumb against my asshole and I clenched tightly trying to fight it. She laughed again and said it would be awfully hard to clench here soon, and informed my the lubricant currently all over my virgin anus was actually Oragel, and pretty soon I would lose control of those muscles, I groaned again in frustration and tried to squirm around, but tied like this I could barely move.

Completely helpless to her desires, I hung my head, defeated. She placed her finger on my chin and lifted my face back up, at that moment she also affixed to my throat a posture collar. It was rigid leather dyed pink and studded with pretty gems, across the front it also said pretty princess I knew without seeing it because I had secured it many times to my wife’s throat.

I felt the straps tighten into place and wife said listen princess, you are mine now, you will obey or I will punish you. If you are a good girl, you might even get a reward from time to time, she said, rubbing my cock for a moment. 

My cock sprang back to life and I couldn’t believe I was actually enjoying this a tiny bit. Oh no hunny you are gonna need to put that away, you are done with it for now she said. And she pulled the pumps off of both my nipples at the same time roughly. I grunted in pain. Then she affixed a metal nipple clamp onto one of my now swollen nipples and then the other. I tried to cry out in pain but my mouth was too full. The pain and discomfort quickly shrank my penis back and she said I was a good girl. 

My mind was racing, what had I gotten myself into. She had lost it I was sure of it. I felt an odd sensation surround my now soft cock, and a little snap then a metallic quick. When I could see again, she explained, I would notice the chastity device now locked onto my cock. It she said was fixed around my balls and locked with a small padlock that only she had the key for. If I behaved, she continued, I maybe allowed to use it on occasion, it even had a pee hole. Getting hard however, that’s was going to be, well hard. It’s only three inches long and not very wide. I groaned, but was helpless to object.

I felt her moving around below and couldn’t place the sensations but as the oragel began to fade, pain blossomed from my asshole and I felt what must be a dildo pumping in and out of my ass. As I started to groan with each thrust she noticed that I could feel it now. The dildo she was using had to be almost as big as Todd’s cock and she started to speed up her thrusts. I was helpless to stop her and after several minutes I began to enjoy it to my disgust.

As she sped up the pace I started to moan, feminine moans that didn’t sound familiar to me. The pain had begun to fade and the pleasure replaced it. I began to squirm what little I could, and my breath had gotten ragged.

Wow princess you are enjoying this aren’t you she asked mockingly. I shook my head no furiously, but couldn’t stop the moans from coming. Louder and louder I got, my cock had hardened as much as the cock cage would allow and was throbbing painfully, but still I moaned like a dripping wet slut as she rapidly plunged the dildo deep into my ass. 

Without warning she snatched the dildo out of my ass and I was appalled that I was sad she had stopped. Next I felt her push a big plug into my sore asshole, bigger then the dildo she had been using. It was quite painful for a moment, then finally it settled into my asshole, stuck there, and I moaned again. Feeling quite full.

I wished she hadn’t stopped but sadly she pulled my panties back into place, covering the cage and began untying the knots holding my thighs up in the air. They were tingly and my toes had gone a little numb. I felt her attaching my ankles to the chair legs with rope carefully tying them to the back legs, forcing my to stay spread wide open. 

Here I was, tied up to a chair by my wife. Blindfolded and wearing her lingerie and dress, gagged, plugged and helpless. 

And I loved it.

My wife said things were about to change drastically for me. She said from now on I wouldn’t be working, Todd made more then enough money to support the three of us. In addition, I would now be required to have an anal plug in at all times unless told otherwise by her or Todd. It would also be a requirement that I dress in only the clothes that we had purchased today and she said they were actually all for me. Next when leaving the house, makeup and heals would also be required. 

I couldn’t believe my ears, and again shook my head no. She giggled and squeezed my balls hard. You don’t really have a choice princess, you have already agreed. I groaned in pain and accepted my fate. She was right I had agreed and with the cock cage locked securely in place, I was in no position to fight back. She removed my blindfold, the room coming back into focus. 

There’s one more thing princess, you will have to start addressing me as Ma’am. Understood? I nodding my head yes and her face lit up. I’m glad we came to this agreement, I know you will fill your new role well. Are you happy with this role princess? 

Conflicted, this all felt so wrong, but so right. And I did agree. Yes I decided, I can be ok with this for now. Yes ma’am, I tried to say through the gag, but failed. My wife giggled and deflated the gag to my relief, unstrapping it and removing it.

I weakly said again, yes Ma’am.

I couldn’t hear that princess, what was that?

Yes Ma’am, I said more confidently. Yes Ma’am I am happy with our agreement. 

Good, she said, just remember obedience will keep you from being punished, and then she squeezed my balls tightly for emphasis. I groaned and replied, Yes Ma’am I will remember. 

My beautiful wife and now it would seem master disappeared behind me again and I breathed a sigh of relief when I heard the jingle of keys as she removed my handcuffs. Free to move them again, I massaged my wrists, sore from being behind my back so long. 

Then she disappeared again returning after a moment with a 10 inch silicone dildo about as wide as my own cock. Again she sat down on my lap, my cock hardened painfully in its cage once more and I winced slightly. 

I want to test your skills she said winking devilishly. I groaned and responded, Yes Ma’am, how exactly would you like to do so? Already suspecting her plan.

Open your mouth wide and stick out your tongue like a good girl, she ordered. I replied yes Ma’am, and quickly complied.

She first licked up and down the length of the dildo like she had my cock this morning, my cock painfully strained against the cage at the sight. 

She then ordered me to fold my lips over my teeth like a good girl. I don’t know why but my heart fluttered every time she called me that. She started to ease just the head into my waiting mouth and told me wrap my lips around it, making sure that I kept my teeth covered. I did so and and she began pumping the head in and out, it made a small pop each time she pulled it out. She told me relax my throat, which was not easy with the rigid posture collar in place. 

When she noticed I couldn’t move my neck much, she thankfully removed the collar straps and hopped off my lap, disappearing again behind me. After a moment she held out a cute pink collar with diamonds and the word inscribed in the center Princess on a square silver plaque and instructed me to put it on. 

Yes Ma’am I replied and set about putting on the collar. She squeezed my balls again harder this time, and in a stern voice reminded me that I had been instructed to keep my mouth open and tongue out with my lips folded over my teeth. 

I quickly complied and she again called me a good girl. Again it filled me with happiness to be commended. Once more she sat in my lap and instructed me to rub her clit. I happily did so, slowly at first. She began to let out soft moans and again held the dildo to my open mouth. Suck on it she instructed, I grunted yes ma’am through the dildo in my throat with some difficulty and sped up my assault on her clit a little. Her breath was beginning to quicken and I could feel the warmth emanating from her freshly waxed pussy.  

Getting turned on, she sped up her thrusts into my throat, now shoving about four inches of it into me. I began to moan myself as she fucked my face faster with the dildo. 

Her soft moans were getting much louder and she panted, faster princess, faster. I happily obliged. Reaching my other hand under her, I began to pump my middle finger into her dripping pussy and she just got louder. 

In response she began to shove the dildo deeper and deeper down my throat pumping it rapidly, seven inches of it roughly smacking the back of my throat. I was gagging on every thrust now and struggling to keep my composure. Tears streaked down my face. And she to me to relax again. 

I added my ring finger to her pussy and started relentlessly stimulating her g-spot while speeding up my attack on her tender clit. She cried out like a banshee and started humping my hand like a slut and started pounding the dildo all the way to the hilt. I felt the gag reflex begin to fade after a few minutes of this and my cock felt as if it would explode. 

She buried the dildo in my throat, all ten inches, and screamed, YOU ARE SUCH A GOOD GIRL! My cock throbbed harder at that.

Holding the dildo in place, she hopped off my lap, told me to start fucking my own mouth, in long slow strokes, from the top all the way to the base. I did as I was asked: She bent down and slowly untied my feet from the back legs of the chair and told me to stop fucking my mouth and come fuck her. Spreading herself out legs lifted into the air, a thin sheen of sweat made her breasts and smooth skin glow. Her pussy was flooded with her desire. 

I jumped between her legs in a split second, ripping the dildo from my throat, ready to fuck her brains out. Then I realized I couldn’t, my cock was trapped in the pink hard plastic cage, secured with a small gold padlock with a heard on it. 

I sighed in disappointment and said, I can’t Ma’am. 

Yes you can, she grinned and handed me a thick white dildo about eight inches long. fixed to a belt, fit with straps to tighten it in place. A strap on? Just great. I obediently strapped it on and once it was fully tightened. Leaning forward again I began rubbing the head in circle against her sensitive clit. 

After a few moments of this she passionately growled, FUCK ME! 

Happy to obey, I lined the strap on up with her dripping wet pussy, and in one move I buried all eight inches deep into her. Her eyes rolled at this, and I paused a few moments to let her adjust to the size. Then I remember that this was still small compared to Todd’s horse cock. Feeling dumb, I began to pull out, all the way to the tip, the I slammed it deep in her pussy. Repeating this over and over, until her breath had gone ragged. Harder and harder I pumped her moans began to fill the room. I reached over to the side of the bed, where all the toys were still laid out and I grabbed her favorite vibrator. It was a small but powerful silver bullet. I held it hard against her clit and she began to buck around wildly. Her moans just kept getting louder, and I just kept pumping faster and faster. 

Normally you would have came a while ago, and I would have been left to finish the deed myself, she panted. Not anymore princess, she moaned. From now on you with fuck me for as long as I want whenever I want. Do not stop till I soak the bed she ordered. I willingly obeyed, I had never been able to please my wife like this before, and it filled me with joy. I kept pumping for another 20 minutes or so, my cock still on the verge of exploding and I could barely handle it. 

Finally, she let out a blood curdling scream and collapsed, cum exploding from her pussy, soaking the bed thoroughly. 

I kept going without mercy, turning up the vibrator a click, she took it from my hands and held it to her clit herself moaning wantonly. My hands now free, I held both of her ankles high in the air and pumped deeper still, speeding up my strokes. Within minutes, she screamed, YOU ARE SUCH A GOOD GIRL! And came again, drenching the bed even more. I was amazed, I had never made her squirt before, and twice in one sitting and her praise filled me with joy, the thought was cut short as my brain went numb and I came hard. I moaned like a little slut, trapped in my cage, it was intensely painful and orgasmic at the same time. 

I faltered for a moment, lost in the pleasure of my orgasm, and she told me I could stop now. I happily replied, yes Ma’am, and backed up, collapsing on the bed next to her. That was great she sighed in contentment.

Thank you Ma’am, I said. Breathing out a satisfied sigh. Several minutes we laid there, catching our breaths. Let’s get you cleaned up, she said after a while, pulling a key out from a chain around her neck. She reached down and click the key in place and removed the lock from my cock cage, then unhooked it. My cock was sore and red and covered in thick white cum. She handed me a towel and I wiped myself clean. Afterwards, she refastened the caged and clicked the lock back into place. 

Only Todd and I will have control over when you come, ok princess? She reminded me, and let the key fall back between her luscious perky tits.

I said Yes Ma’am, and she again called me a good girl. My cock swelled at the praise, filling the cage once more. She giggled and said maybe you can come again tomorrow. I groaned and laid back, getting more comfortable.

She curled up next to me and turned on the tv, putting some chick flick about a guy who had become the third wheel in his own relationship. They came to an agreement similar to ours, and he ended up living out his days happily serving his wife and her new man. Maybe this was where she got the ideas, I thought with a grimace. 

Though I noticed this man had been allowed to keep his wardrobe much more masculine. When the movie finished, my wife said wasn’t that a nice movie?

I quietly replied, yes Ma’am. Lost in my own thoughts.

She rolled over and said she wanted to go dancing. I groaned but replied, when, tonight Ma’am?

She giggled and said we would have to get ready, and that might take and hour or two. So we headed to large master bathroom to begin our preparations. 

Continued in My new life as a sissy, chapter 4 - A night on the town.