Stretch Assignment Pt. 09

Since I'd deep throated Dildos much bigger under Pam's tutelage, I wasn't nervous. Honestly, I couldn't wait to get his warm soft skinned, but rock-hard cock, inside my mouth. Like the star pupil I was, just as my formerly innocent wife had taught me, I never broke eye contact with Pablo. I stared up at him as I batted my eyes and began by kissing his thick crown, leaving bright red lipstick prints all over. I then began using my tongue to take long wet swipes all around his circumscribed cockhead when I wasn't pushing the tip of my tongue into his pisshole. Now that I'd had my first taste, and his pre-cum tasted very nice, I pulled away and let four or five big gobs of spit drop onto his dick.

I used my spit to slowly jerk him off, not trying to get him off yet, but needing to spread the wetness all over his thick shaft. Of course, it did get Pablo even harder. Next, I resumed kissing the very warm, wet head of his prick. Once I had made sure he was really wet and ready for my next feat, I pulled back completely and looked him in eye and winked. Pablo looked a bit puzzled, but I knew right away he loved what I did next.

I immediately got an exceptionally long loud moan. I guess I caused it by dropping my head down and steadily swallowing his entire cock. I went from kissing his crown to tonguing his ball sack in less than five seconds. Wow, he was thick. I had maybe four inches in my mouth, with my lips against his ball sack, and at least three inches down my talented throat. I nearly dislocated my jaw, but opened up just a bit more, to allow me to tongue each of his big, shaved balls.

I now began to experiment, trying out all things I'd worked on last night when I sucked off eight guys to way back when I got kind of tricked and I'd gone down on my first Trans lover, Amber. But most of my tricks came from all the training sessions with Pam and her vast collection of dildos. I had found out, much differently than the Pam I married, the post-Lana Pam was a blow job queen, and she made sure I learned all the tricks of an unforgettable BJ.

So, first I began moving up and down very slowly, using my tongue and lips to caress and maintain suction as I moved all the way down his cock and then return to the top of my motion, letting Pablo's dick out of my mouth only to kiss and lick his crown. Then I'd do it again and again. I was now getting exposed to the full range of moans Pablo could generate. This deep throat rhythm went on for a few minutes, with both of us clearly loving what I was doing to his cock before I repositioned.

I had seen as we drank our wine that Pablo had a very sturdy coffee table. I now laid back on it, my head hanging off the end. Then I had Pablo get over me so, now that my throat was aligned, he could resume his oral fun. But by laying on the table my angle now let him go really deep down my throat in a single motion. Knowing that, I told him to fuck my face and do it fast and hard. He loved that idea.

He slammed his big cock over and over down my throat and I thought both of us were going to cum right then. I got the combination of oral, which I loved, and feeling dominated, something that Lana and Pam had brought out in my sexual desires. But this couldn't go on for too long. After a few minutes, Pablo was clearly about to flood my throat with a load of cum. That wasn't where I wanted his cum, so I stopped him again. Much as I loved the taste of a mouthful of young cum, I wanted his load much deeper in my hot little body. So, I told him to sit on the couch and get ready to enjoy the tightest fuck of his life.

Sammi was still like the boy scout of her youth, always prepared. I pulled my go to bottle of lube from my purse. With a big squirt of the liquid, I lubed up his wonderfully thick and hard cock. At the same time, I leaned over to push my tight ass up to his face. I pulled off my leather gaff thong while I was facing away from him and handed Pablo the lube. I told him get me ready, telling him to spread the lube all around my asshole but also as deep inside as he could reach. As I looked back at him, he grinned and was soon fucking my tight hole with two then three of his long fingers, spreading lube deep inside me. Now I was the one moaning telling him,

"Baby that feels so good, but now I need something better, I need your cock inside me."

I kept him sitting on the couch and lowered my ass onto his big thick cock in a reverse cowgirl position. He moaned even louder than when I deep throated him as I opened myself up and slid down that super wide rod. And while Pablo wasn't the size of some of Pam's biggest dildos, the feeling of a real cock deep in my ass was amazing, and so much better than a piece of plastic. Pablo liked it too, as this very vocal man let out another long deep moan as I bottomed out against his stomach.

Now I was ready to get my prostrate worked over and show this random guy what a great assfucking felt like. I squatted over my lover, leaning back with my arms on either side of his ripped chest to begin to flex my hips and move up and down that incredibly happy lubed cock. I fucked him like a machine, for at least five minutes, loving the sensation of his long wide cock stretching my tight ass as I used my muscles to clench and unclench around him. I had never known what fun it was having a cock rub your prostrate four months ago, now it had me moaning almost as loudly as Pablo.

Just as my own cock was nearing the point of cumming, it seemed that Pablo was also about to bust his nut. My lover now started thrusting up off the couch even harder than before. I knew what was cumming next! He suddenly let out a moan that turned almost to a shout as he grabbed my hips and pulled me all the way down his cock. I now could feel him pulsing as he shot a massive load deep inside me ass. We lay on the couch, me lying back against his hard body, tired after working so hard on top of my partner. Now my long black hair was all over his face and shoulders as his cock gradually softened inside my ass and we got our breath back.

Before I went out tonight, I had really cleaned myself, going through three full enema bags. I wanted my ass to be super clean. So, after we cuddled for a while on that now quite wet couch before we went back to his bedroom, I wanted another taste of his tool. He was probably a little freaked that I swallowed his cock, just out of my ass and still recovering, licking it clean and grinning up at him as I swallowed little bits of his cum.

Then I cleaned out some of the steady stream of cum from my ass squeezing my muscles to push several big squirts of Pablo's cum onto my hand. I probably shocked him even more when, as I looked over at him, I slurped all the cum from my fingers, savoring the taste as I swallowed. He now knew that Sammi was both a very randy and raunchy girl. We then finally went back to Pablo's bedroom. I joined Pablo on his bed, not able to resist cuddling up with him as I continued to play with his recovering cock. Young lovers were the best, in only about five minutes he started to get nicely hard again.

Of course, Pablo wasn't shy, maybe he was a boob man, as he was playing with my boobs again. I wasn't about to stop that; my new boobs were super sensitive, so this was a total turn on for me. However now things got interesting. This big, ripped guy wasn't watching me playing with his hardening cock as I nibbled on his neck, or looking at my massive tits. He was staring down at my extremely hard cock bobbing below my big tits each time he sucked or licked one of my nipples. I felt a hand leave me tits and rub my corset as it moved down to play with my midsection, close to my hard cock. Was Pablo going to really do this?

He was. In a minute he was rubbing my dick. He swirled the large pool of precum around my head and stroked my shaft. Wow, this Latin lover was incredibly open minded. I wondered if he wanted to literally go all the way. I stopped nibbling and asked him if he really wanted to have some fun. I mean he was already stroking my dick. He was puzzled and looked down at me. So, I proposed a big step,

"baby, I cannot begin to tell you how good it feels to get your ass fucked. Please let me show you."

He looked a little uncertain, but then nodded yes after I kissed him and promised him this was only between the two of us and that he really would love it. Next, I grabbed a condom and got the lube ready, after all I doubt he had done any preparatory enemas today. Then, to keep his interest up, I propped a pillow under his ass and started sucking his beautiful cock again.

That was good for both of us. I loved a hard dick in my mouth, and as I promised him, he'd never had a blow job like I gave. After he was rock hard, I wasn't done with his dick, I moved down, taking each of his shaved balls in my mouth to lick and suck on them. Finally, I left his cock and balls alone and moved again so I reached my destination, a very tight, reddish-brown asshole. I now tongued all around it just like earlier, really getting him prepared as I tongue-fucked his tight ass for the second time tonight. Pablo might have been nervous about my dick in his ass, but he was loving my tongue up there, if the moans and groans were any indication.

After I got him started with my oral talents, I really took my time getting him ready using my long, slender fingers. I liked finger fucking a tight virgin ass almost as much as pounding it with my dick. I got him used to just one at first, but in the next five minutes slowly added fingers till I had three fingers sawing in and out of his ass. At that point Pablo was moaning in pleasure. He was as ready as he was going to be, especially as my cock was much more average sized than his. After I slid on my rubber and lubed up my rod, I slowly pushed at his sphincter now wearing nothing but my sexy leather corset. Once he took my direction to push down like he was pooping, just like I expected, I popped right in.

After giving him a minute to get used to it, distracting him by telling him to play with my nipples as I kissed him a few times, I slowly pushed deeper. This was literally the tightest ass I'd ever fucked. Pablo groaned, I'm not sure in pain or pleasure or both. While I loved a dick in my ass so much, penetrating a super tight ass as I got ready to fuck it was also one of my favorite things now.

And I was relentless, slowing pushing deeper and deeper till I was soon balls deep in Pablo's ass. He was now officially no longer an anal virgin. At that point I decided that I'd slowly fuck him, gradually picking up my pace. At first my virgin lover wasn't sure if he liked it, he had this quizzical look on his face.

But after only a minute or two the moaning started again. Still playing with my big tits hanging above him, Pablo began to thrust his ass towards me, nothing tentative about his efforts anymore. I now really got moving, pistoning my cock in and out of the tightest ass I'd ever fucked. We both were loving this, and I smiled wondering how Pam and Toni would react when I told them I'd found an ass even tighter than their cute ones.

But all good things had to end. As aroused and frustrated as I'd been for most of the night, I was surprised I had lasted this long. Now as Pablo moaned below me, a silly smile on his face, I blasted a big load of cum into my condom. I let my cock soften as we kissed and I toyed with his, now rock-hard dick. Though we were both tired, Sammi never allowed a hard cock to be lonely.

As much as I was tempted to roll onto all fours and have him fuck me again, what I hadn't enjoyed tonight was swallowing a big load of cum. So, after I pulled out of Pablo's cute tush I moved down and once again worshipped his long thick dick. He had already cum less than an hour ago, so it took me quite a while to suck him dry.

But once again I used my full suite of tricks, worshipping every part of his tool, from the big mushroom shaped crown to licking and sucking on his large balls. As he clearly got close to cumming again, I stopped deep throating his dick. Much as it was special to feel a hard dick pulse in my throat as it shot a load straight into my stomach, I wanted to give him a final show that would stay in his mind. I wanted his cum in my mouth so I could taste it before I swallowed. So, I pulled his cock out, positioning us so his crown rested on my outstretched tongue. My lips were almost to the bottom of his crown, as I used both hands to jerk him off.

Pablo quickly came with yet another loud shout, shooting rope after rope of cum into my hungry mouth. Wow, the amount of cum he could produce on his second orgasm was impressive! Pablo seemed to love that he could see his own orgasm as he shot his load past my big red lips. I swirled his big load around my mouth, showed him a mouth full of his cum, and then swallowed it all. He tasted super delicious, not slimy at all, and definitely not bitter. I cuddled for a while but had no intention of waking up in this guy's apartment. I really wanted to be home with my two lovers.

So, I washed up and fixed my makeup before I pulled on my super-hot heels and tight leather dress and kissed my Latin lover goodbye. He had not been happy that I wasn't going to spend the night, but perked up when I told him next time it was all three of the boys and me, and maybe one of my girlfriends and we'd all spend the night for sure.

So, just before two AM, I stood on the curb outside Pablo's apartment complex grading my Friday night. My appearance, clothes and dance moves had been out of this world. I had to agree with my new blonde friend in the ladies' room, I was the hottest girl in the club. And I had rocked Pablo's world, giving him oral sex like he'd never had and anal sex like he'd only dreamed of. So, for all of those parts of the evening, I was a rather good Sammi. But that wasn't the real question tonight. It was how I would feel doing all those ultra-feminine and very sexual things. Would I have imposter syndrome and just feel like this wasn't natural? Or would I enjoy myself as I took Sammi out for her final exam?

As I thought about it, appearing to anyone walking past to be a cute girl reading her phone, now with a huge smile, the answer was unavoidable and fantastic. Feeling like I was in a very warm, happy place, I acknowledged the truth. While the cute outfit, dancing and hot sex had been a huge amount of fun, the best part of the night was actually being Sammi. I loved how everyone had looked at me, talked to me and saw me. I was far happier as a hot girl on the prowl, not hiding she wanted a one-night stand with some great no holds barred sex, than I had ever been as Sam the bland hetero guy. And I had loved taking the initiative, seducing Pablo, enjoying the intimacy as well as the oral and anal sex. I hadn't tried all the flavors of sex (yet), but as of now, I viewed myself as an emerging pansexual.

I was amazingly comfortable that Sam was now going to be just a memory, increasingly faint for me. But that didn't mean I wanted to leave all of my old life behind. I still deeply loved Pam but knew that our mistress had been right when this had started four months ago, I really was destined to be Sammi. And since Pam had been pushing for me to embrace my new identity and life, I knew she didn't want to end our marriage either. And at no time since I'd come back had I wanted that. Seeing Pam as Lana's submissive slave had been a shock, but I'd never wanted us to end things.

Of course, with all that had changed in the last four months, it certainly wasn't the marriage we had thought we'd enjoy when we walked down the aisle in church in front of family and friends. But our new, very modern marriage, involving our mistress and lovers of all types was so much more fun. I also didn't know how I'd break the news that I was now Sammi to my family, but if they wouldn't accept her, that was their problem.

As I rode back to the house, tired but very relaxed, I was finally ready to tell the girls my decision. I wasn't going to go back to work as Sam. I was going to be Sammi forever. I also needed to warn them, Sammi wanted much more sex, preferably raunchy and raw. That meant those boxes of Sam's clothes and shoes in the garage could now go to Goodwill. And since my old company would never truly accept Sammi, I'd have to figure out a new path.

But I had two months to do that. I had a thought that I could use my transition to bargain for some kind of enhanced severance package too. And, as Sammi, there were certainly career choices open to me, as long as I was willing to embrace them, that were just not possible for Sam. Despite my recent orgasm, the thought of earning a living as some kind of sexual hybrid and adult performer somehow got me hard again.

Because I was going all in as Sammi, I also realized I had no reason not to make an appointment and start to match Pam in another area. I wanted some serious body jewelry, starting with my nose, tongue, and nipples. But it was way too late tonight to make those plans. My Uber arrived and I climbed in, ready for some sleep. I finally got home and joined my lovers in bed, they were fast asleep already. I slept like the exhausted woman I was. In the morning, before I even made my coffee, I had a text. It was the blonde hottie.

Tania had wasted no time, which boded well for adding another lover to my circle. She didn't just want to text and get to know me either. This direct woman wanted to grab a coffee that afternoon. Remembering that comment about rocking my world, I was getting hard just thinking about Tania's luscious bod, so replied yes, as long we weren't limited to just coffee today. I got back some laugh and kissing emojis, thank god no eggplants, and an offer of how about 2PM. Not even concerned that she thought we both were born girls, I replied with four kissing and thumbs up emojis.

We agreed on a Starbucks and then I had a minor crisis as I glanced at the time on my phone. Due to my late night, I realized I only had an hour or so to get cleaned up and dressed before I drove over. So, I turned to the girls, both up before me, sitting in the breakfast nook enjoying some coffee and petting. I smiled and told them that I had another date in about an hour. But I promised some great news for them afterwards. They looked puzzled but laughed at my antics.

As I ran upstairs, my short silk robe so loose it nearly exposed my ass and already hard cock, they yelled at me to not do anything they wouldn't do. That made me almost trip as I laughed, I had yet to find anything my two lovers wouldn't do. And as Sammi I was already following their path to not having any sexual boundaries. Wanting to take advantage of my new wardrobe and also arouse and entice Tania, I laid out my outfit for my coffee date. I decided to be casual, but sexy. I grabbed my skintight red leather jeans, a white cashmere sleeveless turtleneck, a black leather bolero jacket and some Doc Martens with staked three-inch heels. Sammi was ready for some afternoon delight.

At first, I was going to cover the whole weekend in one chapter, but as this is over 10,000 words just covering Friday night, I'm splitting it up. Very soon I'll upload the fun Sammi and Tania have and how Pam rewards her husband (or is it wife now) for committing to a life as Sammi. And yes, have not idea of what Sammi looks like or becomes at the end of this, and especially not who she fucks.