A Learning Experience Ch. 06

"I know... I've talked to Cindy about this kind of thing happening. Because I've asked you to be my Mistress, you've been working your butt off to get through all of the Sisterhood's requirements. I've known that once you finished, I might have to share you sexually with others. B-but... I guess I was hoping it would never happen... silly."

"Oh no honey, that's not silly, I love you, and only you, forever and always, just as we've always said, remember? Please... let me make you one more promise?"

"W-w-what?" she was crying now.

"T-that I will ALWAYS ask you before I see anyone sexually, no matter the reason, whether it has anything to do with the Sisterhood, or anything else. You will always know beforehand, and you will always have the option of saying no for as long as we are together... w-what do you think... will that work for you?"

"Yes, hell yes!" she exclaimed, "oh God baby, that would make me feel so much better, I had been so worried because I never thought this through, that I... oh Honey, that I would end up losing you because of my own damned S&M needs."

"There was never any danger of that my darling, but hopefully this will keep our love alive by keeping everything honest... and Babe? It's an honest need I have with Smitty, he's been so down lately, and I know he feels like he should have been able to stop my rape by that policeman, no matter how much I protest. I think we need to somehow heal each other, and it's just the only way I can see to do it."

"You're right," she sighed, "shit... you're always right about these things my lovely Joscelyn, and you've been a woman for less time than I've been in college! Cindy has always said the same thing... she said you should have been treated as a female from the day you were born. Your feminine abilities, your fem 'soul' as she calls it, always seems to be able to help others."

"So what do you think about Smitty? ...I won't do this unless..."

"Its yes," she interrupted with a loud and certain voice, "my answer is yes baby."

"Thanks," I said fighting back my tears, "thank you my darling!"

"Tell Smitty he's a lucky guy,"

"No... besides he knows that," I laughed, "No - I'm the lucky one... for having such a love as yours that I can share with him... certainly any 'luck' comes from you."

"Goodnight then my love!"

"Goodnight sweetheart!"

I knew she hung up quickly to reduce the awkwardness, but I also sensed something else... pride. Mel was the most caring, loving, and sexy partner I had ever known. It was now time to use her pride in me to make my savior begin to have pride in himself once again.

Gathering my things and stepping outside, I locked the front door behind me, and locked some extra bounce into my biker-girl step, giving my 'ladies' their extra jiggle. My eyes were now totally focused on the man who had been my protector for so long, determined to expose a side of Josie he would never forget! As I returned, Smitty was fiddling with his bike, until I got close enough to grab his attention.

"Ahem!"

"Oh my God, Josie!" he exclaimed, turning to see me, he could now only cough, as his eyes wandered down my feminized body. My black fishnets and 5-inch heeled ankle boots were brought together with the absolutely tightest leather female biker pants I could find. These had silver grommets all the way down each leg, tied off with leather cord to give the best possible fit. The sight of my pink bustier under a skin-tight black leather jacket seemed to cause the greatest change in his blood pressure. And moody dark red lipstick with black sunglasses under a black police officer's cap on my platinum blond curls finished the look nicely. I'd also taped my most private privates back to make sure this little biker babe couldn't be fingered playing for the other side.

The coming sunset reminded my belly it needed filling once again. "There's a good roadhouse on the way over to your place isn't there?" I said as I put my bags into his saddlebags, and he then helped get them strapped down for me to sit on.

"You mean the 'Teq'... Good food? Absofuckinlutely, but... it can be a little rough," he mentioned while continuing to stare at my 'ladies'. They responded by getting their nipples hard as nails, showing themselves through the thin satin and lace of my bustier.

I quickly zipped up my biker jacket and said, "No problem, I got you babe!"

I then let out the perfect giggle to back up my Cher interpretation! Once more, a very enthusiastic engine kick-start got us going, and we drove over to the Tequila Sunrise Roadhouse. I saw some of the competition walking into the bar and I was really glad I'd put in as much prelim as I had. Now I needed my 'marines'. So I pulled off my sunglasses and hat, giving my Aqua 'marine' blue eyes complete access along with my platinum hair, together they always made a fun combo. As we went inside, I checked them out in the mirror as everyone else was checking me out from behind. We grabbed barstools to get things started, and hopefully it wouldn't be too long before we got our table and, of course, got to order our food.

A lot of keeping the peace in a place like that is making sure you stay glued to your man's side, and don't go starting up 'interesting' conversations with other bikers. Trust me, nothing good will ever come from that behavior. Sure enough, just two stools down, Ms. Biker chick with her way over saturated gonads, left the guy she came with to strike up a conversation with a lonely looking Hell's Angel. Loud voices followed by loud bouncers were the simple result there. In the meantime, I laughed at all of Smitty's jokes while gripping him firmly around his waist, and making 100% sure that every limp wristed action was seen as 110% feminine, and for Smitty's benefit ONLY.

Finally we got our table, and boy was he right, this food was worth waiting for, but the wait had me awash in 7&7s and soon enough... a friend of Smitty's stopped by our table, bringing his redheaded bitch WAY too close to the man I had every intention of having serious sex with later. Before I could even think... one bad-assed green-eyed monster came popping out of little Josie.

"I know he's stepped in crap like you before, but I'll make damned sure he knows better'n to stick anything else in there!"

Did I mention keeping the peace? Well, when it came to one female intruding on another's man, all bets were off! Fortunately, for her and me, Smitty's protection went both ways, and he knew it was time to go! He helped me stand and got me walking away, but the redheaded bitch used the opportunity to try a quick peck to Smitty's cheek... instead, she fell flat on her face! Looking at Smitty just then, I saw the biggest little-boy grin explode all over that stoic face... and then he winked at me! So this is why he does it, I thought, he really does love playing the protector. It was a nice thought, and the last one I remembered as I fainted dead away just as we got outside.

"Josie?... Jo!... hey, c'mon now honey, need ya to wake up!" He was saying as he lightly slapped my face and waved a piece of cardboard at me, to get me a little extra air.

Gradually all the alcohol started combining with the incredible food, and a wonderfully good feeling got me up and rolled through me. Then, as I reached both hands around Smitty's head, the first thing I did was let him stand me up. But that allowed my lips to finally reach their primary target, pushing my tongue deep into his mouth, he began to lovingly give it quick sucking motions, building the heat into an unscratchable itch that left me aching for even more. No doubt about it, I wanted this man as much as anything I'd ever dreamed about!

"Take me home and make love to me or lose me forever!" I said as seriously as possible, but the alcohol slur made it sound just as funny as we both thought it was.

Smitty laughed really loudly, which combined with my giggles made the moment lose a lot of its romantic content, but then he said quietly, "As you wish my darling."

Gently picking me up as if I was made of fine china, a tear raced down my cheek while giving my hero the sexy look he deserved. Then he placed me sidesaddle on his fuel tank so he could keep a good hold on me. After he got on and started the bike, I had slipped down towards the seat and his crotch. Lying there, I could see the black sky filled with sparkling diamond points, and his face at the center of it all. As we drove back to his apartment, I memorized every crack, scar, and age line, he was beautiful in his own unique way.

By the time we arrived, I could walk, albeit with an arm around his shoulder, and while I knew my lover would have been just as happy to simply take me naked in our present drunken ardor, I still insisted we get my bedclothes out of his saddlebags. Smitty lived in a small apartment on the second floor of an auto dealership and junkyard, and wasn't so much a renter as he was a built-in security force. After cuffing and tussling with two of his favorite guard dogs, he said a couple words in German to get them to go lie down in the showroom.

"So, am I safe with those around?" Almost as soon as I'd asked, he responded.

"Safe as in your mother's arms!" He shot back.

Once inside, I asked where the bathroom was and then kissed him hard to help him remember why we were doing all of this! Of course, I giggled all the way into the bathroom. It took awhile to get out of all that leather, but I sure felt better afterward. I put on a white silk and nylon baby doll along with a pair or gaff-type panties... leaving my black fishnets, garter belt, and CFM pumps on for contrast.

Then I carefully titivated my make-up and brushed my hair out to get it as full as possible. I'd had a pair of grape clusters tattooed onto the edges of each of my 'ladies', making sure they were just barely visible above the cups, where I knew it would drive Smitty wild as soon as he saw them. As I gazed into that bathroom mirror, I saw a different Josie come into being... this one was positively aglow with the anticipation at the evening to come. Her large sparkling blue eyes saw the flush of excitement building on her own pale cheeks. NOW I thought, this... THIS is what it looks like when what you have been wishing for... hoping for... DYING for all your life is incredibly about to happen. When you know that you are finally being given a chance for your inner, or true, self to be released... a chance to express that deep emotional need, to give yourself fully... completely... absolutely to the opposite sex.

I then removed the tape holding down my boiclit, or penis, and tucked it into the gaff panty, having no intention of Smitty ever dealing with it. It was one of those strange limits that popped up when I first realized I wanted to make love to a man, I didn't want him touching my currently male genitalia, and it made me cringe to think of it.

After a few months of hormone treatments, I now critically looked at the girl I saw in the mirror's reflection and finally realized that the male-to-male date idea had been a horrible mistake from the beginning. Why? Because I'm NOT A MALE dammit! How many times... dear lord... how many times would I have to remind myself of this, in order to break the terrible habit of trying to hide the true gender I had been born with.

I wanted Smitty as much as anyone I'd ever had sex with, but NOT just because he was a virile man, and NOT just because he had a sexy body. What set me aflame that night was the absolutely pure love that I saw in his heart. Even though he knew this was to be a one-time thing, he was still willing to offer that love to the crazy transgendered girl standing in his bathroom... and share it with no reservations, or strings attached.

I opened the bathroom door and saw him sitting nearly naked, save boxers, on the end of the waterbed, staring out the window until he noticed me and turned his head.

"Oh God Josie! You... you are so beautiful!"

As he stood and took in my vision from head to toe, I was sure my face blushed as pure a red as possible. Meanwhile... stepping closer, he was gripping my shoulders tightly, and it felt as if I was in the most absolutely perfect place... and consequently doing the most natural thing... in the world. He slowly leaned down, pressing his lips against mine, giving a deep initial kiss. Before I knew it my lips were opening instinctively for him to possess me, responding eagerly to the fierce passion now building between us. I was in paradise, closing my eyes to give a soft, profound sigh, as our kiss ended.

Smitty gently pushed the robe back from my shoulders to get a better view of my ladies and it dropped to the floor in a whisper of lace. I moved closer, entwining my arms around his neck, and as he took me into his arms I suddenly felt myself totally enveloped by his masculine presence. My ladies pressed into his bare chest, making me shiver. His strong firm hands slide around my back, exploring the ruffle of frills at my waist, caressing my bare thighs, and finally cupping my lace-clad bottom.

For a few moments I lose all sense of self, reveling in the sensation of a man's tongue exploring my own lips and mouth, enjoying the total pleasure that Smitty is giving me. When he holds my chin between his fingers, I find I'm melting inside like a young girl to her first sweetheart's touch. I run my hands across his broad chest and press against the hardening cylinder of his cock that I now find myself wanting inside me... penetrating me... invading me... making me completely feminine, sexy, and desirable.

I squirm slightly so he can't feel the evidence of my own arousal pushing itself up from under my gaff panties to meet his own wonderful stiffness. I find myself wishing this moment would never end. My confidence grew stronger as his beautiful cock pressed against me, and when he finally broke our kiss, I was looking up into those beautiful, hungry eyes.

"Oh baby," he moaned, "I need you, so much!"

This dropped me into action faster than a slingshot, falling down to my knees immediately as I pulled his boxers out of the way, bringing his 'artillery' directly into line. His cock gently slapped me in the face once as I wrapped my soft pliant lips around that rock hard shaft, there was nothing more that needed to be said for either of us. He began a slow loving massage of my scalp, by gradually pulling my hair into his hands, he was able to steer my mouth around his cock, as he literally fucked my face with as much control as he could put into this gorgeous task. Slowly, while quietly moaning my name, he became insistent with his needs, pushing his cock straight down into my wet mouth, and deep down my throat. Tears were forming when I knew I could hold back no more, instead I remembered what Mel had said:

Breath through your nose darlin', that lovely mouth has other duties right now!

So far, I was keeping up well, allowing him to be deep-throated, and then I could take quick breaks to get my breath back. But very suddenly I had to take him completely as he said, "Josie... oh lord girl, I'm gonna cum!"

He now grabbed the back of my head and came with as much loving force as I could ever remember feeling! Each spurt streaming onto the back of my eager throat as I at first tried to compensate, but then relaxed and just let it happen. But in the end I was simply overwhelmed, falling at his feet with small drips of cum running down my chin. With my long arms wrapped around this mountain of a man. he rewarded my efforts with one of his gorgeous grins, easily picking me up and gently placing me on his king-sized waterbed.

We cuddled for several minutes until we had both recovered. I inched closer, kissing and nipping his member to restore him back to the hardened shaft that I knew I'd never forget after this night.

Finally, with feelings far beyond anything I'd ever known... I placed a trembling hand on each side of his loving face... and gasped through my tears, my one and only wish, "Please my darling... please... take me as a woman!"

The look I received from this gentle giant was nothing less than total shock at the fact that I'd chosen him to take what, at least I felt, was my anal virginity and to do it now, after what I'd recently been through, it was obvious that he seemed concerned. He moved with purpose now, carefully getting out the lube, watching every look I gave for any hint of reluctance. He started gradually, slowly putting lube on his fingers, and then placing them one at a time into my puckered little asshole. While Mel had once taken me with a dildo, this would be far different, not only from that exercise, but my main thought was that this would hopefully over-ride the terrible memories from a few nights ago when only pain was forced to occur at that spot.

Once he had four fingers inside of me, he gently rotated them all around and finally said, "Ok... that's it baby, it should fit now, but you just say 'stop'... and I guarantee I'll stop as fast as you can say it."

He now flipped me onto my back. This effort was about making love, so only missionary would do. "Here babe, point your toes, and keep your legs as close to your body as you can, he then carefully pushed a small pillow under my ass and lubed his cock. My mouth watered remembering him inside of that opening earlier, when it felt as if my sexual world had changed completely. Now that world was being redefined once again, as I had been in this position once before, but the pointed toes of the "come fuck me" pumps belonged to the woman I was about to fuck, not me! He asked if I was ready... which I responded to quickly, and then suddenly... he was in me... he tried to do it ever so slowly, but within a couple of seconds I wanted all of him and pushed back as hard as I could. It was an absolute of absolutes that would force me to delve deeply inside my own psyche.

Unprepared, I cried out at the sudden penetration, even though the invading member slipped into my slippery hole fairly easily... totally filling me. Independent of my control, my head shot back and my eyes closed with the intensity of the feelings within me. The muscles on the top of my legs began to tremble but strong hands hold me down firmly around the waist, preventing any escape. I manage to pull up and away from him slightly but I'm quickly pulled back down onto the slow, steady pressure that signals his advancing cock. I give myself up to the sensations inside me and softly moan, beginning to breathe harder in my excitement. Smitty allows me to raise my bottom up a little, only to push me back down again... to be penetrated a little further, fucked a little harder.

Then I feel the naked flesh of his thighs against the warm cheeks of my behind. I carefully ease myself back onto my little pillow, now extremely aware that my poor bottom is tightly clasping his entire length inside. Staying very still for a long time, I let my eyes re-focus and the intensity of the feelings inside me gradually begin to calm. I angle my head up and see that he is doing exactly the same thing, his eyes once more focusing on my face and his mouth spreading into that handsome smile.

"Smitty, I..." I try to speak.

"Ssshh," he whispers, "You're beautiful... allow yourself to be fucked."

He was right... hell... it was one of the reasons I'd done all of this tonight, to be fucked by this gorgeous hunk of a man. I sighed as he raised his thighs slightly off the bed, sliding them underneath me until they are resting against my lower back. I let myself be almost rolled up into a ball, unable to concentrate on anything except the penetrating fullness radiating through my bottom. The grip around my waist was now fierce as his hips came up and off the bed once more, pushing his throbbing manhood even deeper into my rectum. Suddenly the situation becomes clear, I am facing my own pulsing cock as it is pushed to a point just over my head. Gasping in my helpless position, I realize I am no longer in charge, and only now can I understand exactly what that means.