This is a work of fiction and the characters depicted are fictional. Any resemblance to real events or people is purely coincidental.

Brandi’s ‘Vette

Standing beside the road with my thumb sticking out, I watched the cars zipping by, willing one to stop for me. Little did I know the impact this day would have on my life or suspect the amazing journey of transformation I was about to embark on. After this da, everything would be different.

I had only been there for about ten minutes when a vintage 70’s Corvette signalled and slowed, pulling over onto the shoulder a little ahead of me. The metal flake candy-apple red paint glittered in the sun and the engine throbbed its low rhythmic pulse as I jogged up. The passenger window powered down and the lock knob popped up as I approached. Looking in I saw the driver’s plump tanned legs in loose faded cut-offs. My glance also took in bare feet on the pedals, toes painted to match the car and high-heeled sandals on the passenger side floor. I opened the door and got in, not believing my luck; chicks never pick up male hitchhikers. As I was settling in the driver addressed me in a low sexy contralto whose tone reminded me vaguely of Juliette Greco “Buckle-up sugar. How far are you going?”

Turning toward the voice confirmed my apprehension that the driver was in fact a man in drag. Then again, he radiated a patent femininity, and sex appeal or pheromones fairly dripped from him. The big blond hair was obviously a wig but I couldn’t help thinking of him as a girl. The red tank top she wore couldn’t contain her generous figure and every move revealed choice bits of smooth tan flesh. My face must have betrayed my stunned, conflicted feelings at finding her so instantly alluring in spite of myself. She laughed then, and stuck her hand out. “Call me Brandi.” She said, winking at me.

Taking the hand I replied “Hi, I’m Phil, thanks for the ride Brandi. Uhhhm long weekend off University; I’m going to Victoria to visit friends, you know? Do you pick up a lot of hitchhikers?” I was babbling now.

“Hmmmm well, I only stop for the cute ones.” Brandi laughed again, a bubbly, infectious sound. She signalled and re-entered the flow of traffic. “What’s your major, Phil?”

“English. I want to write for a living.”

I fixed my eyes on Brandi again. Surprisingly, despite the extreme divergence she represented from my habitual range of experience, I found myself really liking what I saw. She looked about twice my age, early forties but damn hot nonetheless, and that regardless of gender. She caught me watching her and giggled again, winking, and blew me a kiss with pouting red lips. I had to smile back. On one level I understood this was a man but come what may I was responding as I would to a woman.

“Ever get lucky hitch-hiking, Phil?” She asked then, “Anything wild ever happen?”

“Is that what’s called a leading question?” I laughed.

Brandi laughed too. “I guess that depends where you want it to lead you.”

I kept staring at her generous curves and that lovely tan skin, and my cock was definitely reacting. “I’ve never been picked up by anyone like you, if that’s what you mean.” Chunky, sexy, sluttish and under-dressed, hell, that’s just about exactly what I’m partial too in women. Nothing strange about craving what I liked, was there? For all its strangeness, the situation swiftly became rather compelling. “But there’s always a first time for everything, isn’t there.” I mused aloud.

“I have found that to be the case young man, more often than not.” She looked at me seriously then and I held her gaze until she smiled and turned her attention back to the road ahead. “First time for everything, indeed. There’s some grass and papers in the glove box, roll us a treat, dear boy.”

I found a bag of prime bud and rizlas and rolled us a nice fat spliff; lit it, toked deeply and passed it to her.

She took it and smoked. We drove on for a short while, smoking like this, before she broke the silence. “You like Martinis? I’m just crazy about them myself.” She sounded a little nervous, unsure. “I was gonna stop at the bar or at least pick up a bottle on the way down. Are you in any big hurry to get to Victoria, Phil. Perhaps you’d care to join a lady for cocktails, my treat of course.”

Cheeky. Well, I thought to myself, here is a smooth, self-assured lady. Clever, witty and tempting, she seduced and engaged my mind as well as my groin. “Nope.” Attempting to remain suave as I answered. “No hurry at all and a cocktail sounds tremendous right about now.”

“Lovely. You know, Phil baby, it being such a gorgeous day, we have a number of options before us.” My answer had eased her disquiet and her voice sounded steadier though still a little breathy. “And you must feel completely at ease voicing your opinion in our little discussion here. First option, we could stop at a bar and chitchat over a few drinks together. Second, I have a little mixing kit in the trunk complete with shaker, glasses and all, so we could get some bottles, some ice, find somewhere to park and have a private little tailgate party confabulation. Or else our third option, which, because it allows us to get as drunk, stoned and crazy as we like, in complete safety and utter comfort, is by far my favourite option. We get some bottles like I said. But instead of having a liquid picnic, I get us a room so you and I can get to know each other privately. Intimately.” She smiled seductively. “How vote you, Phil?”

There was some trepidation at the thought. After all, until then I had never considered myself gay. By then however I had a raging hard-on and my cock felt no indecision whatsoever. I looked her up and down again and formulated an answer my cock would like. “You make a persuasive argument dear Brandi. I vote we get a room where I’m quite certain we will enjoy getting to know one another.”

“Wonderful. So it’s settled then, dear boy. Now all we need to do is find us liquor and a motel.” Her hand dropped off the shifter onto my lap and rubbed my thigh, giving a little squeeze as she let go.

I felt hornier than I’d ever felt before. My head was swimming and my cock was rock hard.

About ten minutes later we spotted a liquor store, conveniently located beside a motel. She parked outside the office.

“You sure about this honey pie?” She asked as she turned toward me.

Rather than answer I reached out, pulled her closer and kissed her passionately. She seemed surprised but pleasantly so. Her lips were soft and parted slightly as my tongue sought hers. As the kiss broke, she pulled a wad of cash from her purse, handed me a hundred and said. “Here. Go to the liquor store and get us vodka, gin, vermouth and whatever else you fancy. I’ll get us a room.”

I made my way to the store. I found the requisite supplies including a bottle of coffee liquor and paid the clerk. We met beside the ‘Vette. “We’re all set. I got us a nice place. It’s got a hot tub, a waterbed; it’s got the works baby. Nothing too fine for a first time.” She winked at me and I could feel myself blushing. “I just wanna park a little closer to our room. Get in baby.”

“Sounds good to me, how long do we have?”

“As long as you like. We’re booked till the morning. There’s an ice machine down the hall; would you get us a bucket? Then I’ll fix us a couple of drinks and we can get down and dirty.” She grabbed the bottles and a small suitcase from the trunk and headed for the room. I went off to find the ice.

Brandi was sitting on the couch when I came back in with the ice. “Come here baby,” She said, patting the seat beside her “Vodka or gin?”

“Vodka please.”

Everything was laid out on the coffee table in front of her. I joined her on the couch. She took the bucket from me and proceeded to mix us a couple of martinis. “Cheers.” She said, handing me my glass and resting her free hand on my knee.

“Cheers.” I replied, clinking our glasses together.

She certainly mixed a kick-ass martini. “Nice.” I said.

Putting her drink down, she leaned forward and we kissed again. Any lingering resistance evaporated as I ran my hand along the smooth hot flesh of her thigh, stroking her gently. Her hand swam up my t-shirt front, caressing my torso before pinching my nipples playfully. She was so sexy, her legs spreading apart, moaning softly. The cadence of our kisses and caresses increased as we became more aroused. She tugged at my t-shirt and I raised my arms, allowing her to pull it off. Her mouth found my nipples and immediately started sucking and nibbling. She pulled at my jeans, undoing the button and pulling down the zipper. I stood to help her release my cock. She pulled my clothes off until she had stripped me completely naked. She made soft little appreciative noises, purring and cooing over my penis as she took it into her mouth. “Oh Brandi.” I moaned gently as I stood, my drink forgotten in my hand, transfixed by the pleasure her mouth and hands bestowed. “You rock me.”

“Mmmmmmm what an exquisite body you have, darling.” She slurred agreeably if slightly indistinctly, as my cock slipped in and out of her mouth.

The experience was absolutely fantastic; I couldn’t understand what I had been so uptight about. Who the hell cared if Brandi was a guy? She was a sex goddess whose manifestation somehow transcended gender. She had released a libidinous force I had unwittingly harboured until then. I found myself possessed of the zeal of a convert. “Baby you are utterly stunning and you fulfill needs I did not know I had. I just can’t believe I’m here with you.”

My drink joined hers on the table as my hands slowly and deliberately explored Brandi’s body, as she did mine. Her skin was smooth everywhere I touched, warm and supple. Kneeling between her legs as she sat, I reached behind her and pulled off her tank top. We caressed each other warmly and tenderly. Like the rest of Brandi; her breasts were amazingly feminine. I cupped one in my hand and took the other in my mouth, swirling my tongue around her nipple.

She knelt beside me and we kissed again, hungrily. My lack of scruples may have surprised her, but I couldn’t help myself. I caressed her belly slowly and slid my hand into her waistband. When my hand encountered hard cock it wrapped itself around it with unanticipated ease. My need overpowered all other thought or opposition as I undid the buttons on her shorts. They fell to the floor revealing a black thong tightly outlining her cock.

“Let’s get into that bed sweetheart.” She said breathlessly.

We stood together and picked up our drinks. Brandi stepped out of her shorts and we walked over to the bed, clinging to each other, reluctant to break contact for so much as a second. Her thong dropped to the floor, divulging the final bits of skin, free of tan lines or hair. Finally we were both naked and we tumbled into bed together.

“Babe, I can’t believe how natural it feels to be with you.” I told her between kisses and caresses. “I’ve never slept with a man and I truly didn’t expect it could feel so usual and somehow proper. Was it like this for you the first time?”

“I took to it as a fish takes to water, just like you darling boy.” Brandi winked and laughed. “You are a find and I will enjoy you.” We kissed tenderly. More or less exactly the way I would have kissed with a girl.

It was me that felt fortunate to be with this wonderful lady with a cock. She pleased me in ways I had never suspected even existed and I still had the rest of the occasion to look forward to I knew not what. The French have a word for love at first sight: ‘coup de foudre’ more or less signifying thunderstruck. That’s a fitting concept for the radical alteration of personal reality I had experienced. Whatever else she decided, I would definitely follow Brandi’s lead.

We finished our drinks and Brandi got up to fetch us refills. I watched her walk away, amazed again how much she turned me on. The lovely swing of her hips, the jiggle of her cheeks and even her cock slapping her thigh, all these things made me want her madly. My cock twitched and oozed a bead of pre-cum. My sexy partner returned with a cocktail glass in each hand, which she deposited on the bedside table before jumping into bed with a giggle. Her humour was contagious and I found myself giggling along with her.

We kissed again until she asked. “Would you like to fuck me, dear boy? I’d love to feel that handsome young cock inside me.”

“Mmmmmmm baby, right now I can’t think of a single thing I want more than your sexy ass.”

“You should find condoms and lube in the night table drawer, darling.”

There were. I quickly tore a package open and unrolled one over my penis. Brandi was crouched on the bed, presenting her gorgeous smooth brown ass to me. I grabbed the lube and slathered my cock generously then spread the rest in the crack of her ass. I rubbed my cock up and down between her cheeks, absolutely loving the sensation as she pushed back against me, moaning softly. Finally I guided my cock into her. She pushed back hard and gasped as my cock rammed all the way in. I grunted my intense pleasure and started pumping my cock in and out of her.

“Oh baby that’s it fuck my ass, yeah, fuck me like a slut.”

There was a strange familiarity about this novel experience, but whatever else, the immense pleasure was only accentuated by the transgression against previously held taboo. My hips were bucking like crazy, faster and faster until, much too soon for my liking, grunting and moaning, I pulled out, ripped off the rubber and came all over her ass. We collapsed together, panting and sweating.

“Sorry that went so quickly, baby.” I apologized.

“Darling, don’t worry about it. I loved what you did to me.” She said rising. “Besides, we’ve got all day and night. Let’s have a quick shower and then we can soak in the tub for a while.”

I followed her into the shower and she washed me quickly with gel soap. Cleaning my cock and balls, soaping up my ass and rinsing me off thoroughly. She grabbed my hand and pulled me out after her.

“Now grab your drink and join me in the hot tub. I’ll bet I can suck you hard again inside of five minutes.” She laughed.

Of course I joined her. Cuddling in the tub, we resumed our mutual exploration of each other’s bodies. I found her still hard cock underwater. Holding it was oddly satisfying, as were Brandi’s reactions to my touch. I enjoyed seeing the passionate expressions that my hands elicited. We played with each other’s cocks like this in the tub as we talked and got to know each other.

She was single, a little older than I had thought and I soon discovered she was quite a fascinating individual. An accomplished computer programmer, she had managed to make a few astute investments while still young and had retired four years ago at 45. She still owned a few patents that brought in royalties too. She loved dancing and Caribbean music, as I already knew. She had dressed in women’s clothing at every opportunity since her mid-twenties but her retirement now allowed her the freedom to truly live as a woman as much as she wanted. Of further interest, she wrote pornographic stories for extra income, and traveled quite a bit, “for research purposes, wink-wink.”

“So are you going to write a hitch-hiker story now?” I asked her, smiling.

“Most likely.” She giggled shamelessly. “This is pretty hot even by those standards, darling boy.”

The thought of men getting horny and masturbating as they read my story was arousing as all get out. I smiled my complicity. “Yeah its hot alright.”

I told her a little about myself, where I studied, what my plans were for the future and the kind of girls I liked. I explained I’d never been with a man before and that, knowing myself, this experience would lead to intense introspection as I reconsidered my sexual orientation. Her advice on that topic was that sex was sex, whoever you had it with. Gay, straight or bisexual, if it made a body happy and it didn’t harm anyone else, what did definitions matter?

After about 30 minutes we climbed out and towelled each other off.

“Hungry yet?” Brandi asked.

“I could eat.” I replied. “What are you in the mood for?”

“Surf and turf.” Came her immediate answer. “I know a great place about 20 miles down the road. We can jet down for a quick nosh and come back for round two.”

The mere mention of food set my mouth instantly watering. “Ok sweet cheeks, let’s do it.”

We got dressed, got into her car and drove off. She bade me roll another joint from the glove box stash. On the way the steady bass thump of dub music accompanied our conversation. “I don’t suppose you’ve ever considered this Phil, but I think you’d look pretty hot in drag.” Brandi declared innocently.

My heart lurched at the suggestion; I sat stunned for a few seconds. “You really think so?” I lit the joint to cover my discomfiture, passed it over after taking a hoot.

She took it. “Easy enough to find out. I’ll take you shopping tomorrow morning.” She giggled and winked at me before taking a huge toke and blowing the smoke into my face and laughing uproariously.

I had to laugh as well. After all, only an hour ago I’d silently pledged to follow Brandi’s lead in all things.

I opened my mouth to say I’d give it a try but what came out instead was. “Would you like a blowjob, Brandi?” I had had no idea I was going to say that!

“Young man!” She looked at me with a mock shocked expression, which soon melted into uncontrollable laughter again. “That is an excellent idea!” She tilted up the steering, undid her shorts and pulled out her semi-hard dick.

I pushed my seat back all the way, knelt on the floor and took a penis into my eager mouth for the first time. I loved the feel of it hardening in my mouth. I tried to remember what had pleased me when girls had gone down on me. Holding her hips in my hands, I licked and sucked for all I was worth. She just sat there smoking as I pleasured her. Once again I was doing something I had never imagined I would ever do and totally enjoying it. Would wonders never cease? I had a feeling that associating with Brandi practically guaranteed the periodic recurrence of wonders. It would be futile to resist under those circumstances. Better to just go with it.

“A girl could easily get used to this, darling.” She said caressing the back of my head.

“Glab oo ee ov se’vice.” I glibly replied around a mouthful of her cock. Which made her laugh.

A little later when she came in my mouth I swallowed her spunk almost before I knew it. It really wasn’t anything nasty and it had given me a hell of a thrill, so again I had to wonder at my former reticence. My lady was well pleased and so was I.

It seemed the gay in me couldn’t wait to get out and I could no longer speculate how far I might be willing to go. Besides, there wasn’t much left undone, was there? I regained my seat and buckled up again.

Presently, we arrived at the restaurant. As a concession to form, Brandi wore her sandals and took a navy dinner jacket out of the trunk, to wear over her tank top. We entered arm in arm and were greeted by the hostess, who called her by name and said her usual table was available.

“Thanks Amanda.” Brandi said. “This is my new friend Phil.”

I felt myself blushing a little, but Amanda, who was about my age, only smiled and said “Hi Phil.” as she handed us our menus. “Margarita’s?” She asked.

Brandi looked at me quizzically. I nodded and Amanda left to get our drinks.

“You are too cute when you blush.” Brandi patted my hand.

When our drinks arrived, Brandi ordered surf and turf, the steak rare and I ordered the same. We nursed our drinks and played footsy under the table to pass the time. Brandi told me she stopped in there frequently on the drive to or from Victoria. The staff was friendly, the food was good and Brandi could be herself here.

We were on our second round of margaritas when the food came. After the day’s exertions and excitations I was ravenous so I demolished the steak and lobster. We stayed for a third drink, and then left for our motel room. Not quite replete, I convinced Brandi to stop at a service station for some beef jerky and pop. The ride back was otherwise uneventful as we listened to dub music while I snacked on the jerky.

Back in our room, Brandi asked. “So, have you considered my shopping expedition?”

I had. “I was about to tell you earlier, but instead I ended up sucking you off.” I answered. “I will follow your lead; in all things homosexual and the like, I trust you implicitly. You can be my guru Brandi, my gayru as it were.” I did love to make her laugh.

“Splendid! Oh sweetheart trust me, you will look absolutely fabulous. We’ll shop in Victoria tomorrow. Ohh this is so exciting, I can’t wait.” Her anticipation made her jiggle delightfully. She bounced over to the table where she had mixed our drinks. The ice had melted so she emptied the bucket into the sink, and batting her eyelashes, handed it to me. I planted a kiss on her lips and headed out to get more ice. “Thanks darling.” She said as I headed out the door.

On the way to the ice machine I reflected on the day’s events. Here I was in a motel, spending the night with a man who wore ladies clothing and this morning when I set out I had believed myself to be straight. You just never know, I chuckled to myself. My bucket full of ice, I returned to the room, where Brandi greeted me with a kiss. She had turned on the radio, found some reggae music and was dancing around the room. I handed over the bucket and she immediately began mixing martinis. I made my way to the couch and watched her, loving her carefree attitude. Finished, she stood in front of me with my drink. Rather than take the drink, my hands caressed her legs and hips, pulled her closer and I kissed her lovely brown belly. She giggled as I undid her shorts and let them fall down to her ankles, soon followed by her thong. I took her soft cock and felt it harden in my mouth. I looked up at her and she smiled down at me, brushed my hair with her hand.

“So now you like to suck a lady’s cock?” She asked.

“Who would’ve thunk, right? Thanks to you I’m discovering much I’d never suspected about myself.”

“Well as long as you’re pleased with what you find.”

“I’m pleased at finding you my beautiful, sexy lady with a cock.” I smiled.

I stood and we embraced. She began pulling my clothes off and soon we were naked together. We kissed and caressed like this, our cocks rubbing together delightfully. So many unexpectedly pleasant sensations that I would never have experienced otherwise, it left me wondering.

“Carpe diem.” I breathed softly.

“How about I carpe your dick instead?” She laughed as she grabbed my cock.

“You’re so cool.” I laughed back.

We made our way over to the bed by mutual accord. We flopped into it and continued our caresses. By now I was pondering anal sex, curious. I had never thought seriously about it before but now, especially after seeing how much Brandi had enjoyed my cock in her ass, I wanted to know what I had been missing all this time. Finally I had to ask. “Did it hurt, the first time you had anal sex?”

“It could have but it didn’t. If you have a gentle partner, take it slowly and use lots of lube it doesn’t need to hurt. In fact it can be very nice. Would you like me to play with your pretty ass, my darling boy?”

Our eyes locked as I answered. “Please Brandi. Show me.”

She spread my legs and started gently caressing my inner thighs, my cock and balls, my ass, murmuring softly as she did. She started sucking my hard cock then took my balls in her mouth, which was absolutely amazing. Positioning herself with my legs on her shoulders, she probed and stroked slowly between my cheeks. “Turn over baby and spread” She winked at me.

I did as she told me, crouching with my ass spread wide and was rewarded with the amazing sensation of her tongue licking the length of my crack. My body thrummed with pleasure. “Oh baby, that is so fucking good.” I was breathing hard, panting the words out.

“You like that sweetheart?” She asked.

“Oh my god yes. So good.”

“Good. Enjoy.”

Her tongue was slipping in and out of my asshole and it was the most amazing sensation yet. Brandi got the lube out and spread some between my cheeks. She slipped a finger into my ass and once again I was surprised how pleasurable the experience was. Brandi asked me to turn over onto my back again and I complied right away. Still fingering my ass she took my cock into her mouth. The sensation was indescribable and left me babbling incoherently. We maintained eye contact as she did this to me; her look was so gentle and loving. I could feel my sphincter loosening under her tender, probing massage and then she pushed a second finger in. There was a little pain but as she stretched my ass to insert yet another finger the gratification was overwhelming.

“Oh yeah, aren’t you the sexy little anal slut. Surprise, surprise, surprise.” Brandi cooed to me. “Are you ready, baby?”

I couldn’t speak but I nodded my agreement as I jittered and panted in the extremities of bliss. She grabbed a condom from the night table and slid it over her cock. “Lift.” She said, indicating my hips.

I did and she slid a pillow under the small of my back. Positioning herself between my legs, She rubbed her cock along the crack of my ass, sending a thrill of delight up my spine. Slowly and deliberately I felt the head of her cock, push into my anus. I gasped at the sudden pop as the tip slipped inside me. I looked up at my lover and she smiled back knowingly. She popped her cock in and out of my ass, each time it went a little deeper into my ass and soon it was sliding freely. Jamming her cock all the way in, she grabbed my cock and started masturbating me. About two-dozen strokes were all it took to get me off and I came all over my belly. Brandi pumped her cock faster for a bit and then pulled out to shoot her own load all over me shortly thereafter. I was taken aback by the peculiar emptiness I felt after she pulled her cock out of my ass. She lay down beside me, breathing hard.

“Brandi baby, my ass is yours.” I sighed. “Do with me as you will.”

“I take it you enjoyed the experience, slut boy.” She whispered in my ear. I held her close as she gently stroked my chest and belly.

“You’ve made a believer out of me.” We drifted off to sleep holding each other.

Sometime during the night I woke to find Brandi sucking my cock. I manoeuvred into position to return the favour. As I sucked her cock, I caressed her ass. She spread her legs and my fingers found her anus. I reached for the lube to give her a finger job.

“What a great idea, I want some too.” She held out her hand and I squeezed some lube into it for her. The playful way she had of inciting me as we discovered each other’s body held tremendous appeal for me. We played for an hour or so, attentively learning our mutual sensitivities until each of us had come once more. Satisfied, we lay together until we fell gently asleep again.

Morning found us entwined with Brandi holding my cock lightly in her cupped hand. She had been observing me quietly as I slept. I smiled at her. “Morning” I said.

“Good morning beautiful.” She kissed me.

“I’m going to have a shower. Care to join me?”

“Go ahead, I’ll be there shortly.”

I headed for the bathroom, whistling. I was lathering up when she came into the shower. Her arms encircled me from behind and she kissed my neck. When I turned I saw she had taken the wig off. “Hi darling.” Brandi said tentatively.

There was no kidding myself anymore. Brandi was a guy, a cute, chubby, older guy, 5’5”, with beautiful tits and short thinning hair. That’s when I realized it really didn’t matter since I’d already discovered I loved sucking cocks. I could hardly complain about the fact that they were attached to men. I smiled at my new lover. “Hi gorgeous.” I kissed him tenderly and passionately. Then, still holding him I looked at him closely and asked the question I hadn’t asked yet. “Is Brandi short for Brandon?”

I was rewarded with a lovely smile. “Good guess sweetheart. You’re so clever.”

“With the wig I’ve always thought of you as a woman; a sexy, sluttish woman with a cock, but a woman nonetheless. Without it though, I find I can only see you as a man. I think I should call you Brandon when you’re not wearing the wig?”

“Of course dear boy. And what shall we call you when you’re wearing your own wig, darling?” He smiled wickedly.

“I haven’t given it much thought. Not Phillipa, that’s for sure.” I laughed.

“We’re gonna have so much fun together, my dear, sweet boy.” He took the soap and began to lather me up. Wrapping up our morning ablutions we exited the shower and briskly towelled dry. Then I sat and watched Brandon re-apply the make-up that revealed the Brandi in him. With the wig the transformation was complete.

“Brandi!” I exclaimed. “Welcome back, girlfriend.”

“Am I your girlfriend?”

“Definitely.”

“Wonderful darling. Lets go shopping. We can catch breakfast on the way.”

We collected the liquor and bar tools, signed out, then got into the car and headed south in search of breakfast and my new feminine identity.