Stretch Assignment Pt. 04

Every day I was kept in that sexy lingerie and my super high heels around the house, only donning male outer clothes if I had to run errands or go food shopping. Even in the male jeans and sweatshirts Pam and Lana insisted I stay in my hose, garter belt, panties and bra, sometimes even with a silk half-slip on top of my lingerie. I had to be careful I had thick socks on to not show my stockings.

Today Pam had picked a simple black lace outfit for me. A bra that she filled with a cheap set of breast forms, a thong, garter belt and black stockings. This was finished off with some super sexy six-inch heels, easier to walk in as they had a one-inch platform. It was eerie and hot how even in my second week of training already how much Pam and I looked and walked alike. As I strutted around with my wife, we looked like a sexy pair of chicks, not a husband and wife, that was for sure.

After only two weeks with my lovers, I was changing almost daily, leaving behind that successful manager who returned from Australia for something else. I wasn't exactly sure what I would end up looking like. But with five months of no work in front of me to force conformity to male appearance norms, I was pretty sure I'd look extremely different.

I was even beginning to question my sexuality. I mean I still got as erect as ever, and loved fucking my lovers, but was also really loving being submissive to Lana and even Pam, and was really anticipating and then treasuring it, every time I was allowed to swallow a big load of my own cum. And to match my other forbidden thoughts, a few times as I swallowed, I wondered what other men's sperm would taste like. But as with my other very scary thoughts, I pushed that idea out of my brain right away.

The girls had held off putting me in an outfit to go out in public. I knew I was looking pretty good, but that step had me pretty freaked out. Going outside, I knew I couldn't handle being outed as a cross-dresser or Trans woman. I would die of embarrassment. Pam had not pushed it, beyond saying my ass would look divine in a tight skirt. We definitely built in some fun dress up games in our bedroom where I tried on so many outfits that I'd always loved on Pam. Other than my longer legs and flatter chest, I looked divine in them. A stone-cold fox was what Pam and Lana called me.

Training Like I'd Never Imagined.

So, each day merged with the next, with Pam and Lana's super busy schedule of my mix of exercises, learning and fun. Between two hours a day of hard-core exercise, and hour plus of grooming and make-up instruction, as well as another two hours of learning to strut in high heels and overall act like I was born with ovaries, my days were actually pretty full. I mean we still needed to ensure we had time to drink and smoke heavily as we fucked and sucked each other too!

But my days also had other instructional blocks, just not like any school I'd been to. This of course included the makeup sessions each morning, as well as hair styling tips, and of course continual coaching for my oral skills. But on Sunday, Lana introduced a new, unexpected, set of lessons.

Our dominant neighbor did so enjoy fingering all of Pam's holes and my ass, but for me anal play was hindered by the fact that until last week, nothing beyond a doctor's finger for a prostrate exam had ever penetrated my ass. And that had been a struggle, with typically an unhappy doctor and patient.

First, Lana noted to me that Pam had also not been ready for ass play. So, she told me that she had trained Pam very aggressively, as she was not going to be denied any of my little wife's holes. She then added, as if it needed to be said, that I was not going to be treated any differently.

Pam smiled over at me, confirming she had worked really long and hard, laughing at her pun, to get her ass ready for whatever Lana wanted to do. Pam beamed as she pridefully told me she had taken a three-inch-wide dildo up her ass after only ten days of training. Later she had even been simultaneously fisted up both her pussy and asshole. I looked over at her, shaking my cute little head left and right in disbelief. No way I was buying my tiny little wife had taken something that large up her tight ass.

As Pam recounted all this to me, she sat across from me, cuddled up against Lana while we ate brunch, clearly the sub in this duo. The contrast with this cuddly couple and the image of my wife having her lover's fists up both her holes was very difficult to reconcile. But then Pam smiled and absolutely leered over at me. My formerly innocent bride proudly shared with me some much more specific details,

"Baby, I took that thick dildo up my ass after only a short bit of training. Lana was able to fist me by the next week. And lover, during that orgy weekend I told you about, I had an eleven-inch, really wide, black cock up my ass...wait to you see the video of that big black dick buried in my little white girl ass."

I was shocked, but also kind of aroused and intrigued. So now the girls initiated my anal training. Just like had been done with her, Lana had Pam start me off with wearing a slim silver butt plug all Sunday morning. That afternoon, after wearing the smaller plug for six hours, she moved up to one that was an inch or so wide. It just felt like it was six inches wide. Sunday night I slept plugged for the first time.

Monday morning our routine added another new experience. Pam showed me how to give myself an enema. I did two, Pam had said I needed to be super clean. That morning, again all made up and wearing my new favorite stockings and lacy black garter belt, Pam and Lana started my real anal training. But in yet another new step, first Lana had me caged in a silver metal cock cage.

My poor dick, limp and soft after Pam had sucked me to orgasm, was locked in a little silver metal cock cage. While the blow job was typical of Pam's hot, wet and amazing, I was so not a fan of that horrible cage. I didn't like it that day and never did, no matter how much my lovers transformed the rest of me. For once Lana had gone too far.

I told her that the one thing I wasn't going to endure was the pain of that cage against my cock trying to get fully erect. And, crazily, I now got harder, more often, in my rapidly feminizing state, than I ever had as a traditional guy. So, after that first caged session, although she would threaten me with it, Lana never used the cage again. As I look back at my new life, this was, I think, the only time I absolutely refused my lovers' efforts to modify and transform me.

But back to what my training sessions really entailed. For the next two weeks I was given a set of plugs and dildos and even some anal vibrators. I had to practice each day, twice a day, to expand my anal passage, develop my muscles, and learn to take any size item up my ass. I soon realized those toys meant I was hitting my very sensitive prostrate over and over. That kind of made up for the extreme pain that some of the wider toys caused the first few times they stretched my ass. At first Pam worked with me, but soon I was given the freedom to train alone, as well as with Pam. What helped to relax me is I was at least tipsy for each session, if not moderately drunk and stoned. In that state nothing seemed to freak me out.

My sessions were always some variation of the same activities, and were never less than an hour long. I would pull out the plug I now wore nearly all the time. That second plug had been easy to manage, not even an inch wide, with a cute purple jewel design at the end. And over the course of that first week, I was soon accustomed to its bigger siblings, getting up to almost two-inch-wide plugs, the jeweled end winking from inside my ass. But inserting those silver plugs brought quite a bit of pain, till I trained my sphincter muscles to open up to get them up inside without any issues.

Then, at first with Pam guiding me, then alone, I would learn to take various items up my rear. There was always a list with the item and how long or deep I had to take it. Some dildos and vibrators were slender, but gradually over time they got thicker and more realistic. And also, I was taught that you can never use too much lube. We seemed to go through a bottle every few days.

To help make all this work, many of the toys had suction cups so I could either ride them or stick them on the bathroom wall and practice taking it doggy style. This was yet another odd aspect of my training, wouldn't the girls always use a strap-on? To make it a real training program, in a surprisingly difficult drill, often Lana would have me switch from a new, much wider toy, to a slim vibrator or some other slender item.

I was graded on how well I could use my anal muscles to clench and keep that much smaller toy deep inside me, after I had been stretched out with a much wider item. Lana called it 'asshole tug of war'. Sometimes Pam was told to either use her hands to try to pull it out, or when using a strap-on and see if I could keep her deep inside, unable to pull out. Lana was devilish in her tasks for sure.

But on that first morning, Lana had scarily shown me all of a huge collection of training items that I was going to learn to use. I was aghast, I told my lovers that not even half those would fit up my tiny little ass. But Lana and Pam laughed at me, telling me that Pam had the same reaction, and within three weeks she was a master. As if to scare me even more, Lana then showed me a training set she called the dinosaur dicks. When I looked at her wide-mouthed, she said she also called them her dragon cocks.

They were a set of four suction cupped devices that started "only" eight inches long and an inch and a half wide, with the final one a daunting eleven inches long and over three inches wide. The largest three had a cool bulb arrangement where they could shoot simulated cum up your rear. That was disconcerting, what were they getting me ready for?

But Pam said her favorite, after she mastered the most massive dragon dick was a dildo made from the cast of a real stallion's erect cock. At thirteen inches long and well over three inches wide, it was even scarier than the biggest dinosaur dick. I kept on shaking my head from side to side, telling my wife that the huge horse cock could not fit inside anyone.

But to make me realize this was doable, Pam stared over at me, with another one of her sexy but evil little grins, and told me to watch and learn. She on the spot stripped, teasingly pulling off her outfit, yanking and toying with her nipple rings, so all she was left with was her fishnet thigh-highs and spiked stripper heels. I was about to see that my once demure wife didn't just look like a randy slut, she had embraced that lifestyle in every way. To prove that point Pam now preceded to rock my world.

She first dumped a huge amount of lube over that fake stallion cock, working it all over that massive rubber dick like she was jerking it off with both of her slender wet hands. Pam also squirted a huge amount of lube up her ass with an odd syringe looking tool. My wife's only reaction to shooting a huge load of lube up her ass was to giggle at Lana and I, wiggling her cute butt. In another mark of the new Pam, she looked right at me, making it very clear why she was giggling,

"Baby that lube is really fucking cold up my ass. I like a hot thick cock or toy so much better than my ass prep. But you will learn that ass prep is key to enjoying anal sex."

All this from the girl who wouldn't let even my finger near her brown hole before my trip down under. I wasn't all that surprised; the last week had shown that Pam's ass aversion was long gone. But I was still wondering what Pam would do with that huge fake cock. It didn't seem possible it would fit up her tight little rear end. Her ass was so tight when I tongue fucked her. That massive fake horse cock would surely rip Pam's ass and leave her bloody on the way to the ER.

But my once innocent wife wasn't at all concerned by the massive dildo she was going to insert up her ass. Pam next stuck that very wet toy to the tile floor with the suction cup bottom and laid another large rabbit vibrator on the floor nearby. Then Pam showed me how much she had changed and learned while I was gone. She squatted over the big toy, still in her seven-inch heels with the sexy clear two-inch platforms. Pam began by slowly pushing end of that massive fake dick against her dripping asshole, rubbing it all around her asshole, guiding it with one hand. It was clear both the wide end of that massive rubber cock, and her wrinkled little butthole were very wet.

Smiling at me, with almost a "watch this shit" look, she then pushed the wide head of that fake cock against and then right inside her tight little asshole. Sighing loudly and grinning at me, Pam never paused after the end of that massive knob went past her sphincter. She lowered herself, slowly taking the big cock up her ass in one long, slow, smooth motion.

My tiny wife now had an eleven of the thirteen inches, and all of the three-inch-wide widest part of that dildo, all the way up her ass. Amazingly, she wasn't hating it, she was loving it! Though her eyes were closed as she descended, she had a huge grin on her face. What was crazy is this had taken less than a minute, and there was no pain, no blood, no drama.

As the horse dick disappeared all the way inside her, Pam began to moan loudly. She wasn't in pain though; her pussy was so wet she had pussy juice running down her thighs and up top her pierced nipples were hard and so damn large. Pam didn't once stop moving or moaning. Once that whole big horse cock was up her tight ass Pam never hesitated. Soon she was riding that big toy as if it was the size of my pinky.

Totally focused on herself, eyes closed, she next began to use her free hand to tease her clit. Pam kept on riding that huge cock up and down as she pulled and played with her clit and her pierced hood. My wife, totally focused on her own pleasure looked hotter than the hottest porn star. But Pam wasn't done, she opened her eyes and looked over at me as she reached down to that other toy on the floor,

"Baby, I've come to love what I'm going to show you next. I learned that I loved to be totally filled up in all my holes, and yes, it's much better with big, thick, real cocks. But this time I want you to just watch, so I'm not going to ask you to fuck my face."

Jesus, what had this foul mouthed, hot slut done with my repressed little wife? Then again, I didn't really want that boring woman back. This Pam was so hot and sexy, she was a vast improvement. Anyway, as Pam had laid that purple rabbit vibrator on the floor, I had an idea what was coming.

Still sitting with all eleven inches of hard plastic deep inside her ass, Pam casually lubed up her second toy, though not her pussy, I could see it was dripping like a faucet already. She held the grip on the end of the rabbit, turned it on to both rotate and thrust, and forcefully shoved it deep in her shaved and ringed pussy.

Pam was focused and resourceful in maximizing her pleasure. She used the ring on her clit hood to pull her hood out of the way so the little clit stimulator was right against her hard clit. Then my slutty partner began to ride the ass toy hard as she fucked herself in a rhythm with the big rabbit vibrator.

Now with both toys buried in her holes, she was even louder, moaning and voicing occasional loud comments, out of her not so innocent mouth, starting with a lot of "oh fucks" and "gawd I love having my ass so full". Or in the clearest sign the old Pam was gone, "Fuck this is almost as good as those three huge black dicks". That last one was deliberate, she was looking right at me as she said it, and winked.

Pam only lasted about five minutes before she had a massive orgasm, spraying a huge amount of pussy juice all over the floor. Wow, what a demonstration. Now that she was done, Pam had to recover. First, she pulled out and turned off the rabbit vibe, tossing it down. Next, she slowly rose up, showing off truly how long and thick that dildo was, buried deep in her bowels. As she rose up to stand tall on my new favorite stripper heels, there was a loud plop sound as that massive toy came free of her ass.

She left that huge dildo sticking up from the floor, slowly waving back and forth, wet and dirty with the lube and the contents of her ass. Pam then walked over towards me. But before she got to me, shocking me again, she turned away and bent at a ninety-degree angle. Pulling her cheeks apart, Pam asked me,

"How big is my gape honey?"

I stared in total shock, that big cast of a stallion's cock had left her asshole gaping at least two inches wide, wow. I told her ass was wide open! She stood up and turned to face me, huge smile plastered on her face. Pam hugged me, kissing my neck as she whispered in my ear,

"Honey, see, not so hard to do. I'll have you riding those dinosaur dicks and then that horse cock in only a few weeks."

And I learned that Lana had taught Pam not just how to be fucked up the ass, but how to assfuck too. Even after I got good enough to practice my ass work solo, working my way up the progression to that goal of fucking myself with that massive horse cock, my little wife loved take control of my ass. She would strap a big dildo into her harness and have a blast pegging my ass.

I had to admit, being fucked that way was truly different, and I came every time, spewing my seed either on the floor or all over myself and Pam if I was under her in the missionary position. And looking over at our mirror was so sexy. There was my cute little wife, often in some very raunchy outfit, fucking me, in a lacy or silky set of lingerie, full dolled up, usually with my leather training corset on, very aggressively. The hottest part was to notice my hard cock sticking down, just dripping pre-cum.

So, between the different lessons, our practice session, and our carnal play, I soon realized I'd been home two full weeks. I had already, in only that first week of butt training, taken the two-inch-wide mid-sized fake dinosaur cock up my ass, and was accustomed to being plugged with the slightly smaller silver plug all day long. I realized Pam had been right, in less than three weeks I'd surely be ready to enjoy fucking my own ass with that massive fake stallion dick. I also realized I wasn't dreading that; I was so horny anticipating it!

Beyond my ass being trained to take massive cocks, like Pam had shown me, there were so many changes. I was more and more looking like my wife, both of us dressing like sluts and fucking and sucking like porn stars. I was seldom sober, but even if I had been stone cold sober, I believe I would have loved the emerging gurl called Sammi. And in the most important part of my transformation, I was now fully under Lana's control, which she demonstrated on that third weekend home.

Next...after these substantial changes, Pam and Lana next both accelerate and intensify Sammi's emergence