Stretch Assignment Pt. 07

Pam and Lana reminded me, as we enjoyed a cocktail on the patio, of my wish. They told me to get myself as ready as possible to seduce a hot guy, we were going hunting tonight. The girls told me that the best way to see if I was still Sam in some way or fully Sammi was to face the ultimate challenge, and fuck a cis guy who wanted to make me his gurl for the night.

Mission Accomplished -- Sammi Finds herself a Real Man

That evening, for my entire two hour long preparatory session, as I made myself as hot as I thought, then, was possible, I was debating what I was going to do tonight. I mean, yes, I had enjoyed having sex with Amber, but that was a gurl, just like me. A girl with a nice hard dick, but still someone who was pretty kinky to start. Could I really make small talk and seduce a very macho, traditional guy, hopefully with a much larger, very hard dick? Had I really asked Lana to make this happen? Could I grab his ass, feel for his throbbing cock and kiss him as if I was a woman? Could I wrap my arms around him and dance and nibble on him to tease and entice him?

Even more difficult for me to resolve, could I suck his hard cock and take his dick up my ass? Well for that last part I certainly had enjoyed Amber's cute dick, so that wasn't likely a dealbreaker. But most importantly, did I have the guts to tell this faceless guy that I wasn't like any woman he'd been with and face possible scorn and disgust, or scarily violence? I had no idea. But I was going to find out very soon, first, if I was able to attract someone to me, then if they wanted to fuck Sammi, and finally if I'd have the guts to go through with it, and hopefully at least like it.

And Pam made that all a lot easier for me. As I finished working on my nails, hair, and face she came into our dressing area. She insisted I try on a new black leather mini-dress. It was super sexy, definitely never to be worn to church. It barely covered my nipples and didn't even go half way to my knees. It showed off my big tits and tight ass, but since, like a tube top, it didn't go above my big fake boobs, the tight black leather really displayed my shoulders and slender arms. The dress was basically in invitation to take me home and not make love to me, but fuck me as hard you as you could.

Of course, I had gone all out with every part of my look, definitely anticipating the type of dress and heels Pam would select for me tonight. I was benefiting from almost two months of lessons on how to transform into anything from innocent young wife to slutty club chick. Tonight, I went fully for the darkly dangerous, boldly sexy look. I knew it was right for Pam's choices, our goals for tonight, and most unexpectedly, how I already most liked Sammi to look

When I was done, my hair was all coiffed so it was this wild curly mane going down my bare back. I knew it looked super sexy, but damn it felt so hot over my bare back. My makeup was perfect for the outfit, bright red lips and very dark eye treatments, super dark eye shadow, with extra-long, thick lashes. Even before I pulled on my dark stockings and super high spike heels, I knew I oozed sex. Once again, getting ready for an evening out, the makeup, the nail polish, the hot outfit and sexy shoes, all complemented by my massive head of dark curly hair turned me from this new Trans gurl scared of what lay ahead, into a confident, sensual, sassy creature. Looking in the entryway mirror, I was ready as I was ever going to be. As the girls and I, each of them nearly as hot as I was, climbed into our Uber, on the way to dinner and a night of clubbing, I had a feeling tonight would go great.

Dinner was fabulous, we split a bottle of wine after our cocktails, getting lots of attention from the waiter and busboys. If only they knew I had a nice, fully functional cock tucked away in my gaff panties. Pam and Lana were acting the total femme couple. Pam was all dressed up in a very sexy silk little black slip dress, looking like a very traditional cute girl. But Lana was all in leather like me. But her outfit was nearly a fetish ad, heavy buckles and tight corset top tight dress. With her tall boots and severe make-up, it was clear she was Pam's partner. Their behavior, and choice of dresses, definitely implied she was her domme tonight. It was almost like they were putting me out as available, the two of them clearly committed lovers.

We had eaten a late dinner, so it was nearly midnight when we made it to the club that Lana and Pam had picked out. I had heard of it, it was notorious for wanton behavior, pick-ups and generally crazy evenings. Pam had whispered in my ear when she saw my raised eyebrows when she told me our destination, that here at Club Wild it was likely no one would be upset when they grabbed my hard cock instead of a wet pussy. I guess that made me a little calmer, but maybe not. Would I feel ok feeling a guy, not a trans gurl like Amber, getting aroused, rubbing his hard cock on me?

The place was packed and the music loud, strobe lights and swirling clouds of fake smoke setting the tone. I loved the crowd right away, diverse, yet sexy in their dancing and outfits. As we made our way to the bar, we got lots of attention from men and women. In not a big surprise, before we could even order a drink, a hot couple had offered to buy us some drinks. He was tall, with dark curly hair. She was a very slender, very hot Asian girl, her hair cut in this very cute bob cut. What stood out was she had an improbably large chest, from personal experience, I could tell those boobs were a marvel of science not biology.

I would have thought no one would have approached Pam and Lana, they clearly were a couple, and their tone was strongly dom-sub, but that wasn't how they played it once we hit the club. They split up immediately to look for other partners, not waiting to be approached. Lana chatted up the cute Asian girl with the big chest, Stephanie, while Pam began to dance with a series of hot guys. I was immediately being monopolized by my ripped, curly haired new friend. And that was actually perfectly fine. He clearly loved big tits; he was staring at mine pretty blatantly. And Steve, he had told me his name while staring down at my hard nipples, pretty obviously thought I was a very hot woman. And I actually was so totally Sammi now, I was getting aroused in so many ways by his attention and his actions.

It seemed so natural to be very close together, bodies tight against each other, our heads nearly touching, though I justified it to myself that it was necessary because the club was so loud. I was also relaxed by the two dirty martinis I had already downed. I did jump both in surprise, and from how fucking good it felt, at what came next. Steve, much taller than me, even in my six-inch heels, leaned even closer and ran his lips and tongue up my neck to just under my silver hooped earrings, whispering in my ear how me he loved my perfume. And I had to admit, that my Chanel was super sexy on my skin. I was loving that he both felt good and smelled really good too.

Steve was clearly totally trying to pick me up, and we'd only been in the club like twenty minutes! In a first real validation that my changes were more than physical, I was wondering if he and Steph had a place nearby, and if she would freak if I went there with Steve. I wasn't all that worried, she was kissing and playing with Lana as much as I was teasing Steve. Once again Lana had zeroed in on a very hot, apparently submissive young thing. I was betting that Pam was not the first nor would she be the last to fall under Lana's control.

It seemed like after this weekend I might easily end up in a crazy fuckfest with not just Lana and Pam, but also now Toni, Steve and Stephanie. Throw in Amber and Tommy from the poolside cocktail party and we'd have an orgy going. My other thought, as I wondered how to make that eight-person party happen, was had I really changed not just physically with my big tits and lips, missing ribs, and smooth body, but emotionally and sexually? Or was I just finally accepting who I was, a very hot gurl, reveling in all my body's very aroused reactions to Steve's attentions?

And I was aroused, our arms were already around each other's mid-sections, so it was almost natural, that as I turned to him, he leaned down and kissed my bright red lips. I didn't jump or get scared, I simply opened my big inflated lips and teased his tongue, pulling it into my mouth. Steve and I were like a couple of high schoolers, kissing each other for at least the next five minutes, hands moving over each other's body, caressing and stroking. We took a break to sip our cocktails and he slid behind me, pulling me against him, as we watched the hot action on the dance floor. Now his hands weren't on my waist anymore. He had pushed my hair to the side and was attacking my neck with his hot lips while he played with my big new tits with his other hand.

I didn't know what I loved more, his pinching and squeezing my sensitive breasts and nipples or him sucking on my neck with his little love bites. It was wild, my first weekend out I was perched on super high heels, dressed like a total slut, while a guy I barely knew was playing with my boobs and sucking on my neck. And, as Sammi, I totally loved it. I wanted to do this every weekend! I did stop him when he started to move his other hand from stroking my stockings up towards my crotch, figuring that surprise could wait. And to be clear, I also wasn't just a passive object of his affections, I was working my hips in time to the music, semi-twerking against his crotch. He seemed to like it, a lot; his dick felt massive between my ass cheeks. And that hard cock now made me happy, not freaked out!

It was clear we could stay and drink and dance, but both of us were much too heated for that. I wasn't resisting things, but knew I needed to make a couple of decisions on what was next. And the time was now, as Steve suddenly spun me around to hold my ass cheeks , keeping me tight against his sexy chest. He looked down at me, kissed me lightly on my lips and asked if I'd like to join him in their apartment, just the two of us, it was just around the corner. Wow the offer had been made, and after less than an hour in this meat market. I knew what I wanted to do, but also wanted to be fair to Steve and let him know what I was, for my own safety, before we left the club.

So, I kissed him several times, just as passionately as he'd been kissing me, telling him I'd love to fuck him all night long. Then I paused, and looked him directly, telling him I wasn't like any girl he'd ever been with before. He grinned, telling me he liked it kinky! I grinned back, telling him that while I loved to indulge in all my kinks, and I had a lot, that wasn't what I meant. It was time. I took a deep breath, grabbed his wrist and pulled his hand off my ass and around to go under the front of my short dress. I placed his fingers on my barely concealed, hard throbbing cock. The moment of truth had arrived!

Steve didn't pull away, but played with my dick with his hand, as he pulled me close again, kissing me again, with even more passion, making me moan loudly. Then pulling back his head, to look down at me, Steve told me something I was very happy to hear,

"Sammi, I've always wanted to try this, making love with a trans gurl. I just never dreamed I'd find a partner as hot as you are!"

He then kissed me a final time, open mouthed, as both of us enjoyed our tongues playing with each other. I was finally going to do it, fuck a hot guy, my very first-time clubbing as Sammi. Though this was certainly a big step in accepting and exploring my new identity, I was very confident in handling Steve physically. I was also, arrogantly, very sure I was going to rock his world, able to do things I hoped Steph couldn't.

With all my training and hard work practicing, I knew I could deep throat his cock, which happily felt like a very large package. I was pretty sure that would shock him, but would also get me the load of hot cum I had started already to look forward to from my partners. I also knew, after the dildos Lana and Pam had fucked me with, my ass could easily take his hard dick without any pain. I was wondering if he would be willing to suck my smaller dick and spread his cheeks for my tool too though!

But that would have to wait. I knew I needed to let Pam and Lana know I was leaving. I went over to the edge of the floor, Lana was nowhere to be seen, but I spotted Pam dancing in the arms of very hot guy. In no big surprise, she was grinding on him pretty good, and I noticed she was playing with his likely very hard cock when her ass wasn't massaging his rod. As the song ended, I went up to my sweaty, slutty wife and kissed her, surprising her partner. I told my very hot, very worked up partner that I was going to Steve's apartment, and would find my own way home. Pam just grinned and gave me a big kiss, telling me she was happy for me, but she was still figuring out her options. This was not a scene I could have ever imagined only a few months ago.

I was going home with a guy I'd just met, fully intending to swallow his cum and take another load up my cute little ass, while hoping he'd allow me to do the same. I was leaving my wife and her dominant mistress lover to play in a dance club, likely taking home some number of other partners to fuck all night long. And it felt fun and right and perfect for me as Sammi. I was literally dripping imagining how Steve's dick would taste and how that big cock would feel plowing my ass.

I was now totally Sammi, sexy, forward, daring, and continually horny. I was open, so far, to just about anything possible sexual, except Lana's cock cage of course. I strutted back over to Steve, enjoying his big grin and big bulge deliberately swiveling my hips as I walked into his waiting embrace. I gave him another big sexy kiss, telling him I was ready to rock his world. Then grabbing his hand to hold in my slender hand, with its bright red inch long talons, we left the club. We looked like a typical couple, off for a night of hookup fun, but we both knew that the night would be as kinky as we could make it.

A Night to Remember

Steve hadn't been kidding, in only about five minutes we were getting out of the elevator for their 16^th floor condo. It had felt different but very right to walk down the two blocks, snuggled up against this tall, very hot, guy. Steve promised, between kisses and playing with me in the elevator, that I'd love getting fucked looking out over the city lights. It wasn't a big apartment, one bedroom, as I was soon to find out, but it had that balcony, and the view was amazing.

Steve and I weren't more than glancing at the view though. We were kissing and groping as we got hotter and hotter. He did immediately pull my tight dress below my big boobs, and divided time between kissing my neck and sucking those massive new bolt-ons. It felt even better than when Pam or Toni had done it, something about the rough feeling of Steve's day-old beard as he kissed and sucked my boobs, was a huge turn-on. He had a mix of soft and hard kisses that was so arousing. I thought a couple of times he was going to pull my nipples off of my boobs, but that mix of pain and pleasure was amazing, I didn't want it to end.

I think we both knew that our kissing and petting as we got a bottle of wine open and some sexy blues on the Sonos speakers was only the beginning or our carnal fun. And I was no longer conflicted or confused about being Sammi. I so wanted to get a mouthful of his obviously big and hard dick, before I got my ass plowed by this cute guy I'd just met. I was almost on fire; I was so horny.

At this point I was so ready to be everything Steve wanted. I wanted to worship his hard dick, as I played with his cute abs, before I showed him what real ass muscles could really do. But I needed something right away from Steve, before he got my ass, and I had a feeling he'd not resist me taking it. Because I didn't want to run away or scream in fear of what was next. What I wanted a mouthful of hard cock and very soon after that as much hot cum as I could coax from his dick. Sam was gone, I was now Sammi, physically, emotionally, and sexually. Pam and Lana may have thought they created me; I knew they had simply unlocked who I really was and pointed me towards what I could be.

So, with my hot leather dress pushed down below my big round tits, yet still tight around my hips and thighs, showing off my legs, but hiding my hard cock, I pulled away from Steve, to slide slowly down in front of him, rubbing my wet nipples on him the whole way down till I was kneeling on the plush carpet. My hands played with his tight buns for a minute, as I kissed the outline of his hard cock through his tight jeans.

But I wanted more. I unbuckled his belt, unbuttoned his pants and pulled them down. Barely hidden by his tight silky black briefs, was a huge rod, nicely with a big wet spot at the end. Again, it seemed I was turning into quite the tease, I kissed and sucked his rod through his briefs, down that impossibly long way from his crown to his big balls. That got even more moans from Steve. Now my first goal was so close.

When I pulled down those sexy briefs I got literally a big surprise, an even better one than I had anticipated. Steve's cock, was massive, larger than I had guessed and the biggest one I'd ever been near. It had to be at least eight and a half inches long, maybe two inches longer than mine. It was also much thicker, maybe half as wide as a coke can. And to add to the fun, his glans was so hot. It was big, very red, with a cute flange, even wider than his shaft. And the end of his shaft was nicely exposed, my new lover was thankfully circumcised. I could tell he was ready, his knob was already wet with pre-cum.

Before I got to work, I decided one last tease was in order. I leaned in, and while looking up at him, with a big grin, licked up all his pre-cum with a long circular movement of my tongue. I then gave his tip a nice little kiss, leaving just a trace of my lipstick there. As I stared up, he rolled his eyes, smiled again, and pulled my head back to his midsection. Clearly Steve was in the mood for no more teasing. He wanted his dick sucked, even though he knew I had one also under my dress.

And I wanted so much more than just a taste of that hard dick. What was the most affirming part of this evening fun, is Steve had gotten just as hard, and leaked pre-cum in the apartment, as at the club. He got super aroused, long after he knew I was Trans. I turned him on in both cases. That reinforced that I was going to love being Sammi, and would be able to find plenty of partners who would only judge me on how hot and slutty I could be. So, taking a deep breath I went to work.

Though something I wanted so much, and was already enjoying, could never be called work. Over the next few months, no matter how many dicks I sucked, and cum I swallowed, I was never able to think of it as hard work, it was too much fun. So, I started with some techniques I had used before, learned from Pam. Those little tricks and routines would soon become some of my signature moves as much as Pam's.

First, I wanted to take Steve's measure. I had a way to do that not involving a ruler though. I pulled down on his balls with my left hand, long red nails wrapping around the bottom of his warm shaft. Then starting at the balls, I traced up the sensitive vein running up the bottom of his rock-hard cock, finishing at his big red crown. It was a slow and very wet lick, and if Steve's dick hadn't been rock hard before, it was now.

I knew his long dorsal vein was likely very sensitive, and it felt different under my wet tongue than the rest of his shaft. And what a shaft it was, so big and thick. It was so warm, rock hard, and yet somehow, his skin was super soft. And pulling those big balls down just reinforced how fucking huge Steve's cock was. I LOVED it. When I got to the end of his shaft, I pulled away though. I wanted to focus on and play with the end of that huge dick next.