This is the third instalment in a series of short stories or chapters that detail a young man's encounter with a transvestite and the subsequent developments. I've received a few encouraging emails, so I know I'm not alone. I know a lot of people figure if the story is hot, why bother using proper grammar. But, this is meant as a thinking man's pornography. If you need to reach for a dictionary, consider that you are enriching your vocabulary. I've enjoyed writing this and I have more to say on the subject so you can expect additional submissions from me. This is a work of fiction and the characters depicted are fictional. Any resemblances to real events or people are purely coincidental. That being said I hope you enjoy.
Brandi's House
The semester was over and I was looking forward to the summer. I walked the five blocks to my apartment feeling jubilant. Looking ahead down the street I could see Brandi's Corvette parked across the street from my place. I had just written my last exam and would soon be on my way north; Brandi had arrived the previous night and was waiting for me. Aside from a lay-over on her way back to Victoria one night a few weeks before, I had not seen her since she had dropped me off after spending the weekend together.
Since then I had pondered my sexual emancipation. I had experimented with my new wardrobe. I had spent much of my time at home dressed as a woman. Becoming more familiar with the idea; I was finding the whole process rather thrilling. Otherwise, I hadn't gone looking for any new partners.
Brandi and I had kept in touch online with instant messaging and web cams. I had discovered an exhibitionist streak in me that incited me to put on some rather sluttish fashion shows that rapidly degenerated into pornography. Brandi seemed to like it and I know I did.
Now I was looking forward to a period of frequent physical contact and down home fucking. Brandi had let me know I was welcome to stay at her Courtney area home for as long as I wished. I planned to spend some time there this summer; naked and working on an all over tan like Brandi's.
On the kitchen table I found a sealed white envelope. Picking it up, I headed into my bedroom.
I had left her in bed about 3 hours earlier and when I came in that's where I found her gorgeous nude body. I stripped quickly and jumped into bed on top of her. We snuggled together like this, kissing deeply. "Hi Brandi" I said.
"Oh hi sweetbuns." Her gorgeous voice still made my knees weak.
"What's this?" I asked, showing the envelope.
"I've read some of your work Phil darling, I love your writing. I want to encourage you; I want to sponsor your studies. Call it a student grant. They're post-dated cheques, you make them out to your landlord and that way, if you want, you can spend the summer with me without worrying about this place. Come August you can resume your studies refreshed and regenerated. Everyone needs a break. Have a break babycakes."
"Well I can't say I don't need the help." I looked at her, digesting what she had said. I certainly could use some time off this summer. And my only other realistic option was a lousy job slinging burgers and fries. "And you have a point about my needing a break."
"Exactly! Besides, I can afford it and I am glad to do it. Isn't that what friends do for each other? By the way, how did that exam go?"
"I did great! Now I'm just pumped for the summer."
"Wonderful. I knew you would, darling." She beamed up at me, lying on her back.
Our cocks were rubbing together hard as I sat astride her groin lovingly caressing her exquisite tits. She held me lightly, hands on my hips, grinding her pelvis into me. I loved playing with Brandi; she always seemed to know exactly what I wanted. I leaned in for more kissing.
Brandi was as smooth as ever, thanks to electrolysis but I was starting to stubble up and she said she would wax me when we got to her place.
"Thank you darling, you're the best." I said to her. "You might spoil me if you keep this up."
She told me. "Darling, you deserve to be spoiled." I was starting to believe her.
I looked forward to a change of scenery, Brandi had told me her place was very private, 40 acres of rugged forested land with her house in the middle, clothing optional. The only people she allowed there knew the rules and behaved accordingly. Once a year she held a massive party cum orgy for her birthday. According to Brandi as many as 75 people of every possible gender or combination thereof, from all over the world would be present this year for Canada Day weekend, July 2nd 2006, being her 50th birthday.
I pulled a condom from the night table and slipped it over my lady mentor's glorious piece of meat. I coated her with a generous helping of lubricant gel. Then moving forward slightly, positioning my anus by feel, I rolled my hips and the head of her cock caressed its way around my rim. As I felt myself loosening up, I impaled myself with one swift move, taking all of her deep into my ass.
"Unnnhh! Damn Brandi, that's so. fucking. good!" I cried out. My words were punctuated by the thrusts of her cock in my ass. "Mmmmmmm yeah baby! Give me that juicy cock." Our eyes locked as we rocked in concert and a silent smouldering communication flowed between us. We were so good together, whatever we did. I loved my sweet tranny lady and I knew that she loved me.
I rode like no tomorrow, up and down on her wonderful hard cock. Brandi was such a pleasure to be with, I had missed her a lot since our time in Victoria. We gazed at each other with tenderness and carnal lust, a desire to give one another all pleasure known and possible; however, whenever or wherever such was desired. I couldn't get enough of this sweet lover of mine. Her tits were sweet, her mouth was sweet, her cock was sweet, and her ass was especially sweet.
"Oh, I love you Brandi!" I really meant it too. She had been amazingly good for me.
"And I love you Phil; you've given me so much joy, so much pleasure since I've known you, you wonderful boy. I've loved you from the first day we met."
I was rubbing my cock as I rode her; it was covered in pre-cum juice. Masturbating faster with her cock deep in me I swayed back and forth and soon came all over her lovely plump belly. I leaned forward, lying on top of her with her cock still inside and gave her a long wet kiss as my semen squished between our bellies. I loved to feel my cock sandwiched against her soft warm flesh. I had become very sensual of late. "Please darling, would you come on my face?" I asked her, dismounting and lying beside her.
"Ohh my sweetheart, I would do anything for those beautiful eyes." She kneeled on the bed; grasping her cock she pulled off the condom and started jerking off right over my face.
I loved it. She placed her sac in my mouth and I sucked gently on her testicles, rolling them around on my tongue. Her stroking got harder and I caressed the crack of her ass with one long finger, lingering over her anus, rubbing little circles around it. She went wild, hips bucking like crazy. I stayed with it and she moaned when I finally pushed my finger in to the knuckles and I was rewarded with a spray of hot jism all over my face.
She kneeled in front of me and we embraced and kissed, she licked her cum from my face and into my mouth where we swirled it around our tongues. Brandi had told me this was called snowballing; I thought that was a lovely word for a beautifully filthy act. I loved snowballing with my Brandi and we did it a lot. We both got up and went for a shower; Brandi took off the wig.
In the shower with Brandon, we lathered each other up, caressing each other with the water running over us. Even such a mundane thing as showering was much more fun with him involved. Once clean we stepped out and towelled each other off.
Brandon put the wig back on, becoming Brandi again. We got dressed quickly and Brandi applied a quick touch of lipstick and blush. I had packed my bags the night before; Fiona's entire wardrobe was in two suitcases.
I filled in the cheques and took them downstairs to Mr. Krasnoterovski.
When I handed him the envelope I said, "There are 3 cheques in here, post-dated and signed."
"B. Wells? Who is this is?" He asked in his thick eastern European accent.
"That's Brandi; you met her about a month ago when she visited."
"You find yourself a nice `sugar-mama' it look like." He burst out laughing.
I smiled, "She likes my writing."
"Oh yes! I'm sure she does." He continued with more laughing, coughing too now and knee slapping. It's all very funny to him.
I just say "Thanks Mr. Krasnoterovski. Have a great summer sir." And head back upstairs to get ready for the trip.
I looked around; making sure nothing was amiss before leaving for an extended period of time. I ushered Brandi out and followed her. Locking the door behind me I followed her to the `Vette. We put my suitcases in the trunk, climbed in and took off. I was learning to love being her little boy toy; paraded around in her vintage muscle car.
Brandi had told me she was taking me shopping again today. Unimpressed with my masculine attire she said she wanted Phil to be dressed as well as Fiona was.
We went to a sex shop first; she said she wanted some thongs for me. She bought me a dozen in assorted colours and prints once she determined my size. When she saw me looking at vibrators and dildos she offered to get me one of those. I found a nice thick 10" black latex vibrator. We exchanged meaningful gazes; I knew we'd be having fun investigating sex toys. She looked around and grabbed a few more things from the shelves. "Just for kicks, right?" She grinned wickedly.
I loved her naughty sluttish nature; it brought out my own streak of perversity. We went to the cashier and Brandi whipped out her card again.
As she finished ringing through our purchases, the cashier asked. "Will you be wanting any lube with that?"
We looked at each other quizzically, Brandi and I. Shaking her head she answered. "Nope. We're fixed up pretty good lube-wise."
"Thanks have a nice day." She said.
"Bye." We said together, giggling.
"Now we go to the mall. You need some new duds, baby. Nothing wrong with bohemian chic around the campus but I really want you in something more dressy for polite society and times we want to go to nicer places. Know what I mean?"
"Yes dear." I said, meekly.
She laughed at that. "Come on. Let's get you dressed."
At the mall we drew a few glances but the place was fairly quiet. We found a haberdashery and she did for Phil what she had done for Fiona. She was such a whiz about clothes; talk about a queer eye. Personally fashion was not a thing that came to me naturally. Once again I was in and out of the change room for about an hour at the end of which I had several outfits; flattering and interchangeable which made me look everything from young euro-trashy to GQ. She transformed me completely; I could not recognize who I saw in the mirror. Even the jaded store clerk seemed impressed with her flair and chic in putting together ensembles.
The shoe store was even faster. When I left there I owned a half dozen pair of shoes that complemented my new wardrobe.
That done we drove north to her house.
Situated on a mountain slope her house was a largish, rather plain, four bedroom rancher. What made it great was the land. About an acre around the house was cleared, with lawns and gardens surrounding it. Trails ran through the forest, some leading to lookouts and interesting views, others to meadows and clearings. Some simply looped through the forest returning to the house. I met her dog, Sappari Shita, which Brandi told me means `frank' in Japanese. It was a big, wolf looking dog, Malamute maybe? I don't know; I'm no dog expert. Brandi said he kept the wildlife in check and the property safe, and looking at him I believed it.
Brandi and I were alone for the whole month of June and I don't think I got dressed one single time. Brandi went out and did all the shopping on her own but even that was only three or four times. My all over tan was coming along just great. Brandi didn't wear anything either and we were constantly fooling around.
I spent some time learning to walk in heels with Brandi coaching me. She soon had me rolling my hips like a trollop. My growing femininity pleased her I knew. Even just walking around the grounds she watched me closely with an expression of equal parts pride and lustful desire.
I was fully aware that some might conceive of me as a kept man. The slight twinge I felt thinking about this meant there was at least some truth to that. It was however, more complicated.
Isn't it always?
With Brandi you had to consider the whole package and to me the package was simply irresistible.
Having accepted Brandi's financial help I knew I was committed, come what may. She had facilitated an exploration of a previously unknown. What? Lifestyle? Personality? Whatever you cared to call it. She had made it not just possible but downright easy. She was a singularly powerful individual, an almost irresistible force. I could not rightly compare her with any other person I had met and not just because of her gender bending. To my own great surprise I appeared to be falling in love with her. Indeed I could scarcely imagine being without her, especially after this month.
She was serious about encouraging my writing. When we arrived she had shown me my study. It was a great little space with a view on the little orchard. A futon, bookcases and a computer desk with a macbook pro and a mini stereo on it furnished the place.
"The Wi-Fi network extends over most of the landscaped grounds. You can take this laptop anywhere you like, but this is your space. Do you u.nderstand? Whenever and however, you have a place to sit and write, or think or read or just if you need a little privacy."
"Wow! This is a beautiful place Brandi. Thank you so much for making me feel truly welcome."
"Oh but you are welcome. So very welcome Phil, but don't ever feel like you're obliged to stay. If you ever want to leave let me know and I'll drive you home right away."
"Ok Brandi, I understand." I had replied.
Evenings we went online; contacting friends of Brandi's to invite them to her big bash. We got into it pretty hot and heavy a couple of times with some of them. That exhibitionist streak turned out to be about a mile wide; Brandi and I did a few live sex shows for some friends using her webcam. Those were fun and I thoroughly enjoyed the attention.
Brandi said I should consider these webcam shows a sort of rehearsal for the party. She had hired a couple of porno videographers to capture the event for posterity. The thought of being in an orgy made me squirm. Anticipation, dread, arousal and something akin to stage fright warred within me.