This is the second 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. Thanks rashell ;) 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 Condo
We arrived at Brandi's James Bay condo around 10 am. It was a nice little one bedroom on the third floor with a magnificent view of the Olympic Mountains across Juan de Fuca Strait. Brandi had told me she spent a lot of time at this condo in Victoria. She also had a house up island near Courtney, which she considered home.
When we came in the first thing she did was put on some reggae music. I sat in the living room enjoying the view as she mixed us a couple of her eternal martinis. She sat beside me handing me a drink and then pushed a box across the coffee table toward me. It was a lovely Native carved cedar box, which I had noted as I sat waiting for her.
"Roll us a joint darling boy." She said. Then she stood and started dancing around the room to the beat of the music. She shimmied out of her shorts and pulled off her top, carrying on dancing in nothing but a thong. I could have watched her sweet, plump body jiggling for hours as she danced. I had never met anyone who had so quickly and totally enraptured me.
I tore myself away from her captivating movements and turned my attention to the box, inside of which I found everything I needed to roll, including some fantastic weed. I set about rolling a fatty. She danced her way into the bedroom and when I'd finished rolling I followed her.
"I'm looking for something to wear to take you shopping, but I may be getting ahead of myself. I think we need to start from the beginning and that means losing a lot of body hair. Are you game, my sweet little slut boy?"
I had in fact anticipated this and had already decided I would follow my wise and sexy beloved's lead in all things transvestite. "Brandi darling," I said. "Whatever you think is best."
"Marvellous! Then we'll head for the salon and get you bikini waxed. Oh sweetheart you are going to be just gorgeous when you're smooth all over. You're going to love it too, it makes your skin come alive baby." She enthused. "What are you waiting for? Light that sucker up. Let's go to the moon."
I lit, toked deeply and passed the joint to Brandi. She took it and inhaled deeply. I approached her from behind as she checked herself in the mirror and wrapped my arms around her, hugging and caressing her. She rested her head on my arm and we looked at ourselves in the mirror. I thought we looked so hot together. I rubbed her belly and nibbled her neck, then pushed my hand into the waistband of her thong to pull out her cock. It was already hard. I turned her around to kiss her and she started pulling at my clothes to undress me. I helped and soon we were naked in her bed. I was flat on my back and she knelt astride my thighs. Our cocks rubbed together deliciously and she grabbed both of our hard shafts together. Wrapping both hands around them she spread our pre- cum around until we were slick with it and then stroked up and down slowly and deliberately. I looked down at our cocks slip sliding together like that in her hand and blew my load all over Brandi's hands.
"Well, we're definitely discovering the things you like, aren't we dear boy?" Brandi quipped.
I was a little embarrassed at my hair-trigger ejaculation. "Don't tease sweetheart, I couldn't help it. One look was all it took. It was just too damn sexy watching our cocks together like that."
"Oh don't worry darling, it's perfectly natural to ejaculate quickly in a new and extremely arousing situation." My lovely Brandi considerately explained. "We're going to be friends for a long time you and I. You'll see this will all work itself out." She was right of course but I still wished I hadn't come so fast.
"Would you fuck my ass for me baby? I want to make it up to you." I winked at her.
"You don't owe me anything lover boy, but if it's what you really want, that wish may well be realized." She murmured hoarsely.
I turned around and presented my naked ass to her. She got a condom and lube out when she saw this. I heard her tearing the package and slipping the condom on behind me. She spread some lube in my ass crack and slipped a finger into my ass. I had only felt this for the first time last night but it seemed so familiar and welcome. As she played inside my ass Brandi reached around to stroke my cock at the same time. My anus slowly relaxed and she pushed in two more fingers, stretching my tight little hole, but not unpleasantly. She judged me loose enough and this time she jammed her hard cock into me in one long smooth stroke. It was awesome! My backed arched and my cock twitched as she pulled back and plunged in again, deliberately. A moan escaped my lips.
"That's it anal slut boy, moan for me, tell me how much you love my cock in your tight little slut ass. Mmmmmmm I love to fuck you darling, to see your beautiful young body responding to my cock inside you, to hear your soft moans and grunts. Pleasure little treasure." Her voice was husky, her breath ragged as she pumped my ass.
I loved the way she talked so dirty; it made sex unusually exciting. "Oh yes Brandi, fuck me hard. I love your cock inside me." I couldn't believe the things I was saying. "Fuck me like a slut. I want you to come inside me. I want to feel your beautiful cock exploding in my ass" It was in fact quite startlingly unlike me but again I did not seem capable of helping myself. My mouth opened and obscenities poured forth unbidden. What's more, I absolutely loved it. I wallowed in it. I groaned and writhed as her beautiful cock ploughed in and out of my ass.
Brandi's rhythm accelerated until she gave a final tremendous thrust and groaned as she shook with her orgasm. She pulled out of me, discarded the condom and we lay together again, deliciously exhausted. She somehow found the joint we had forgotten and re-lit the thing. We finished it together lying in bed watching our reflections in the mirrored ceiling above.
Some indeterminate time later we got up and showered again. As we dressed I asked Brandi if she waxed. She told me she had before, but electrolysis had fixed that once and for all. "Does it hurt? Waxing I mean." I asked.
"No pain no gain. You have to pay the price if you want to be that sexy." She retorted. "And trust me, you do want to be that sexy. It may not be pleasant but it is well worth the discomfort. Electrolysis is worst than that but I'm so glad I did it."
"All right. I do trust you my beautiful, wanton mentor. Now take me to the beauty parlour and let's begin this metamorphosis."
"Yes let's go. We have a busy day ahead. Have you thought about your new identity yet? What kind of girl are you going to be?" She asked as we left.
"I still don't know Brandi. Any suggestions?" I replied.
"I think nice girl, prim and proper in white undergarments. Your hair, long and black, serious looking glasses, squarish and almost stern. A skirt and blouse, perhaps with a lab coat or a blazer; you'd make a great bookish beauty. For kinks, I see you in a schoolgirl uniform if you know what I mean."
"I see you've given this some thought." I smiled at her. "Are we taking the car?"
"No dear, we can walk there from here. We'll come back here before we go shopping."
We walked down the street a few blocks and turned left onto a side street to a little beauty salon. We ducked in and sure enough Brandi was hailed by name and welcomed with open arms. My baby was a popular girl and I was made welcome by association.
"Hi girls this is my new friend Phil. Phil is an adventurous lad and today we'll be trying to help him contact his feminine side. Don't let me down girls, I know we can do this." Brandi declared
"Hi Phil. Welcome." The `girls', Beth and Ruth, were the beauticians. They were about Brandi's age, friendly and business-like. Fortunately the place was empty that day so they were available. Ruth told me to go behind a screen, strip, wrap himself in a towel and lie on the table.
I said hi and went behind the screen. Brandi told Beth she wanted a manicure while she waited for me. I stripped and climbed onto the table. I could hear the steady banter of Beth and Brandi beyond the screen. Soon Ruth, who said she'd been instructed to give me a bikini-wax, joined me. She asked if this was what I wanted and I told her it was. "What about your back, chest, arms and pits?"
"That too." I said.
"Well all right then, lets do it."
The first strip surprised me and I bit back a squeal but after three or four I understood the process and knew what to expect. It was just a matter of sitting through it now. Lying on my back she started with my feet and worked her way up.
We had reached the towel. Before removing it, she asked. "What shape would you like for your pubic hair, Phil?"
"Ummm I thought we were removing everything. Brandi! What about pubic hair?" I yelled.
"Get rid of it!" Came Brandi's reply.
"You heard the lady." I said.
"You're the boss." She said. She pulled off the towel, arched an eyebrow and smiled appreciatively at the size of my erection. I can't help it; the exhibitionist in me loves being scantily clad in front of someone. It has always aroused me.
I read the question in her eyes. "I must be bisexual." I said.
"Yes that must be it." She laughed.
"Don't be mackin' on my man, bitch!" Came Brandi's voice from behind the screen.
"I never knew you to be jealous, Brandi." Piped in Beth.
"Sorry Brandi. He's just so cute." Ruth winked at me. "Mmmmmmm nice thick cock, too." She gave my cock a friendly squeeze.
"Hey! Cut it out!" Brandi was laughing this time. "Damn, he knows how to use it too." The three women roared their laughter at that. I smiled quietly. Hey a guy likes to feel appreciated once in a while, especially about his penis, especially by a roomful of women.
After that she set about methodically removing all trace of hair from my groin. This area was more tender, but looking down at how sexy smooth my legs looked without hair encouraged me to persevere. I gritted my teeth and balled my fists.
"You're not that hairy for a guy." Ruth told me. "If you keep doing this regularly the hair grows thinner and easier to pull out."
"Is that so." I tried to sound aloof but that's hard to carry off through gritted teeth.
"Yeah, and I think it looks pretty hot on you too." She bent to whisper.
I looked down at my newly bald cock and sac. It was gloriously smooth and sexy.
"Yeah. You're doing great honey." I said to Ruth.
"How about you, doll? How do you feel?"
"I'm fine, keep going. It looks awesome."
This she did. Removing the hair from my stomach, then my chest and finally she did my pits. About an hour and a half had passed.
"Ok. Now it's time for a break. Beth! You got a joint rolled yet?"
"Yeah, yeah. Keep your shirt on." Beth answered.
Ruth looked around the screen. She gave me the towel again and called out to Beth and Brandi. "Since no one else is out there why don't we smoke back here, girls?"
I sat up on the table.
Beth and Brandi came in and got the joint going.
Brandi approached and ran her hand up my smooth chest. "Mmmmmmm that's lovely darling."
"I know. I love it too." I said.
"Has Ruthie been hitting on you, darling boy?" She asked.
"Only to make you jealous." I took her hand to pull her closer, slipped my arm around her waist and gave her a soft little kiss.
The joint came to me and I took a toke and passed to Brandi. She took a puff and passed to Beth. We smoked like this until the joint was done. "That was some good shit, ladies." I said in the aftermath. Beth asked if I wanted a coke or something and I indicated that a coke would be super.
Brandi gave me a quick kiss and headed back to Beth's work area. Ruth turned back to the table and me. "Ok on your stomach pretty boy. I'll be doing your arms, ass and the back of your legs. Your back only has a few stray hairs on it. I'll tweeze those individually."
I turned onto my stomach and let Ruth finish. Another forty-five minutes was all it took. Then she spread some lotion all over me, to help my skin heal she said. When I stood and looked in the mirror I saw my body was completely smooth from the neck down. Visually, it might take getting used to but I loved the feel of the air on my skin.
"Thank you Ruth, you made that surprisingly quick and easy." I told her. I got dressed quickly and stepped out to find Brandi.
"You have to come back and show us the results. I'm so keen to see what you will look like as a girl."
We said goodbye to the girls and headed back to the condo before going out shopping.
When we got back to the condo I immediately stripped to show Brandi. I couldn't believe the difference in sensation just from her touch. Even air flowing over my skin was a delight. If I had known how good it felt I might've done this a long time ago. Brandi stripped too so our skins could fully come together. It was electrifying, the smoothness of her lovely skin on mine. I kissed her thoroughly, ripping off her wig in the process. I threw it down, not caring and drew my man into bed with me. "Brandon darling you are completely transforming my life. Thank you." I kissed him again, our tongues wrapping around each other. "I want to fuck you baby. I want to make you squirm with pleasure and I want to see your face when I do it." I grabbed a condom from his night table.
"Oh Phil, take me, please." His voice was hoarse and low. He rolled over onto his back, propping up his hips with a pillow. I spread his legs and kneeled between them, pulling closer to him. I grabbed our cocks together as Brandi had done earlier. Without hair the pleasure was almost unbearable as our most sensitive skin made total contact. Not wishing to shoot my load right away like the first time, I quickly let go. Instead I ripped the package and rolled the condom down over my cock. Brandon was looking up at me, legs spread out waiting for me to fuck his ass. I lubed him up and slid my cock up his ass in one smooth pump. His face seemed to melt and he almost purred with joy. "Oh yes! Give it to me. Sock it to me. Oohooh fuck my ass baby."
His lovely smooth ass felt amazing against my own smooth thighs, belly and balls. I fucked him slowly, holding onto his thighs for leverage, pumping my cock in and out of his slick hole. Watching his pretty tits and cock bounce around to the rhythm, I had to admit once more that homo sex could be every bit as rewarding as hetero. If I hadn't taken a chance I might never have known. I reached down and took hold of his cock. I rubbed my thumb over the head. "This is so fucking hot Brandon. I can't believe how much I'm enjoying being gay." I was breathing hard now and slowed my tempo a bit to prolong the pleasure.
Smiling a knowing little smile. "I'm so not surprised. The pleasure is also mine, my lovely little slut. I truly am happy you have no regrets about our encounter." He replied.
"Not the least regret and still looking forward to my drag lessons." I speeded up again, both my cock in his ass and my hand on his cock. Pumping us to a mutual climax, I hoped. I wanted to see Brandon's semen shoot as I creamed in his ass. His hips started bucking and I could tell he was close to coming. "Come for me baby. I'm about to shoot in your ass." I plunged my cock as far into him as I could and held there as I jacked him off. All of a sudden he stiffened and shot his hot spunk all over both of us, some even spurted onto my face. This instantly triggered my own orgasm. My hips bucked against Brandon's ass and we moaned and sobbed together. Pulling out, I crawled up the bed and collapsed in his arms. We kissed deep and lovingly, holding tight to each other. We rested like this a moment, a tangled, sticky, ecstatically happy mess, until we could catch our breath and go have yet another shower.
We woke up an hour later and quickly showered, dressed and headed out. "First stop wig store." Brandi said. We hopped into her `Vette and drove off.
At the store I tried on about a dozen different models and colours. I didn't really like myself with black hair, and finally I settled on a lovely wig with loose auburn ringlets that came down past my shoulders. Brandi said it looked pre-Raphaelite. I liked that.
Then we went to a lingerie shop that specialized in ladies underwear tailored in men's sizes. "This way you can wear the daintiest of panties and still have room for your boys. Know what I mean, jellybean?" With Brandi's guidance I acquired a lovely white lacy bra, thong, and garter belt set, along with silk stockings that felt absolutely incredible on my bare legs. Brandi then insisted I take the same outfit in different colours, one black, and one green to match my eyes. I also picked up a divine little green merry widow girdle. She had brought me some extremely realistic silicone falsies to boost me up to a D' cup. Brandi picked up a few articles as well, including outfits that matched my own, so we could be sisters'. I found myself enjoying the experience; Brandi really made shopping so much fun.
"Next stop: shoe store!" She declared after she'd paid for our purchases.
According to Brandi this was where Victoria's strippers and hookers bought their shoes. Like the lingerie place, they also had women's fashions in men's sizes. I began to wonder just how many cross dressers there were out there. I found some nice white sandals, with a low, wide heel that I could walk in easily.
High heels take work, I found out when I tried a pair. Brandi was helpful as always, giving critical advice from her long experience. She said she would help me learn to walk in heels if I wanted.
Again Brandi insisted I take a pair in black and if they had had them in green I would have had those as well. I wasn't familiar with such generosity and I began to protest. She simply said this was giving her so much enjoyment that she was more than happy to treat me. "Besides," she said, "I can afford it. Just let yourself be spoiled by your rich bitch girlfriend. Ok?"
"Well, alright then. If you insist." I let her buy me the shoes.
"A couple more stops sweetheart. Then we take it all home and put it together to bring about your transformation. Can you feel it yet?" She asked on the way out.
"I can. It feels like a tremendous potential building up around us. Like what we're assembling will be greater than the sum of its parts."
"Have no doubt my darling; you will be stunning."
"I've never really enjoyed shopping before but I'm loving this."
"Wonderful, dearest." She said. "Now lets get you dressed."
We got back in the car and headed for the mall. "We'll be needing the bra and falsies to try on some tops. You should wear the wig too, so don't forget this bag when we go in. And take those black shoes too. It's always best to try clothes on with shoes." She advised.
Until now we had been shopping in small boutiques that catered to, shall we say unusual, clientele. The mall however was a more conservative environment and Brandi's flamboyant manner was attracting attention. We headed for a plus size store. Heads turned as we walked hand in hand through the halls to our destination. "I love these places." She said as we entered. "They've made life much easier for so many of us queens. You have a lovely slender figure but six feet two inches is way taller than most girls and this place provides for tall girls too."
I was feeling a little self-conscious about buying ladies clothing; I could see women in the store looking at us furtively. "Ok babe, find me something to wear. I trust you implicitly."
"Ok you're a 34" waist, right?" She held a black skirt in front of me to check for size. She pulled three others in different patterns and colours, repeated the procedure and handed the lot to me. "Go to the change rooms. I'll bring you some tops to try on too."
The attendant gave me a strange look when she saw me arrive with my armload of skirts but she let me in. I had stripped and was putting on my bra in one of the cabins when I heard the attendant outside say "Oh hi Brandi. How are you sweetie?" That woman knew everyone. I had to laugh. I adjusted my falsies and put on the wig
"Here you go darling, try these on." She handed me some tops over the door.
I came out with the first skirt and a nice little green satin sleeveless top. I looked at myself in the mirror and was surprised to find Brandi had been right. I did look good in drag. "Ok here I come." I opened the door and stepped out.
"I knew it. You look marvellous, darling." She clapped her hands and signalled me to twirl and give her an all around look. "Get back in there and show me how you look in those tight little baby-T's."
I gazed at myself in the cabin mirror again. "Fiona." I murmured. "Hmmmm." I took off the top and slipped on a black baby-T. Sideways in the mirror it really flattered my new tits. I stepped out and Brandi whistled her appreciation.
I smiled and giggled. I was startled though not disturbed to find that my comportment and manners were acquiring a distinctly feminine attitude. It was really working.
I curtsied and said, "You know what I'm thinking, Brandi? I'm thinking Fiona. What do you think?"
"Welcome Fiona. So good to finally meet you, darling." She embraced me and we held each other for a minute. "Ok. Go try the other top and another skirt. I'll be right back with more stuff for you to try on."
"Yes, go ahead." When I looked around, some shoppers had been staring at the odd couple, but they quickly found something to occupy their attention when they saw me looking. I really did not care anymore though, I wouldn't allow anyone to mess up the lovely day I was having. I turned and re-entered the cubicle with a bounce in my step.
Inside I changed into a short pleated skirt in black watch tartan. I loved the way it felt when I twirled with it, the wind and fabric brushing my skin was very arousing. I switched tops as well, pulling on a muslin long sleeve peasant blouse. The girl I saw in the mirror was definitely hot. Tall, athletic and stacked; I might have hit on this girl last week if I saw her around the campus. Now I was this girl. How crazy was that? After adjusting my wig, I stepped out again.
"Fiona darling, that is lovely." Brandi said when she saw me. "Didn't I tell you? You're "drop dead" gorgeous. I bet you could pull straight guys looking like that, and without make-up even. Wow!"
"Thank you Brandi. You're the one making it all possible though." I said effusively.
Brandi had a great little black dress for me to try. "Every girl needs one of these, darling. Hand me the ones you've tried already, and go try this and the other ones too."
I gave her the things I had tried already, and re- entered the cabin. I took off the skirt and blouse. I admired my smooth body in a lacy white bra and thong before shimmying into that little black number. Sleeveless and snug as a glove, hemmed at mid-thigh, it was perfect. "Nice." I said catching sight of myself in the looking glass.
"You have to zip me up." I called before exiting.
"I'm right here." She said as I opened the door and turned my back to her. "Damn! Don't you look fine baby doll?" She sounded so pleased, as she zipped me up.
I stepped away and twirled around for Brandi to admire. "You have a talent for dressing me sweetheart. Everything you've brought fits and flatters me." I was beaming.
"Next." She said. And I went back to the change room.
A little green sundress with a delicate floral print was the next thing I tried on. I didn't bother going out this time since it obviously fit. The final item was a black leather mini-skirt that I really liked. With it, Brandi had brought a sleeveless white shirt and a red bow tie to wear under a leather perfecto jacket. I loved the juxtaposition of formal and counter-culture street wear. Looking at myself in the mirror, my auburn hair cascading over that leather, I decided I wanted to wear that one home. I came out with the rest of the clothes, including what I had worn to come here.
Brandi whistled appreciatively. "Once more you look stunning," she said. "I am one lucky girl."
"Well, we're both lucky I think; both fortunate that our paths should have intersected so serendipitously. I shall forever remember the day of our encounter Brandi, my lover and mentor." I took her face in my hands and kissed her sweet lips.
"Ok that'll do for a start Fiona, we're out of here." Brandi told me.
"I want to wear this now. Do you mind?" I asked
"Of course not. Here, let me take these tags off for you."
We headed for the cash registers together. I was already becoming accustomed to being dressed as a girl in public. It was a little thrilling, my cock wasn't hard but it had been steadily leaking pre-cum lubricant since I had started trying on these clothes. Brandi put everything on her card and we walked out together, carrying our bags full of clothes, happy and oblivious to the gawking shoppers in the mall. We strode across the parking lot to the `Vette and drove back to Brandi's.
We arrived back at the condo around 6PM. Brandi bade me roll another joint, which I did. She stripped again, explaining that at home she wore as little as possible. Turning the stereo on again she put on Althea and Donna, truly seductive reggae music. She asked. "Are you hungry beloved? I know I am."
"I'm famished darling. What do you suggest?"
"How about we order in some pizza?"
"Sounds great, go ahead."
"Oh I wonder if Jimmy is working tonight. He's the delivery boy. I usually tip the kid a BJ." She winked at me. "Yeah, yeah. I know. I'm a cheap slut, but hey, we both enjoy it." She laughed.
"You amaze me. I've never even heard of anyone like you. Not outside the realm of fiction anyway." I replied also laughing.
"That pleases me Fiona."
Hearing my new name was still a kick. I was Fiona now. I stood with the joint, puffed it alight and danced over to Brandi. "Shotgun, baby?" I asked her.
"Oh yeah!" She whooped. I reversed the joint in my mouth and blew a stream of smoke into her lovely mouth. Brandi took it like a pro. She signalled enough with her hand and I pulled the joint out of my mouth. "Thank you." She said hoarsely as she blew out a phenomenal stream of smoke.
She returned the favour, blowing me a shotgun in turn. Then we passed it back and forth between us until it was cashed.
"What do you like on your pizza?" She asked when we were done.
"Pepperoni mushroom with extra cheese." I answered without hesitation.
"So be it." She picked up the phone. "Oh hi Jimmy, it's Brandi. I was just wondering if you were on tonight." She winked at me. "Yeah baby, can you bring us a large pizza with pepperoni, mushrooms and double cheese?" She listened for a moment. "You'll see who `us' is when you get here." She listened again, laughed and said. "Of course dear boy, you know I always take care of you. Now hurry, we're hungry and horny." She hung up. "He wants it. Bad." She said. "Let's get you ready for him. I'm gonna do your make-up."
"Does he know you're really a guy?"
"I'm pretty sure he does. I know he loves the fellatio though, and he's never said anything about it. Either he wants to preserve the illusion or he doesn't care. I've never had anyone with me when he came over but he sounded pretty keen. Will you join us or maybe just watch me blow him?"
"I don't know. I guess I'll just play it by ear when he gets here." I answered.
Brandi had a small make-up case in her hand. "Sit down, Fiona." I did and she started on me. Foundation, blush, eye shadow, mascara and finally lipstick, it took her about 20 minutes to do it all. When I looked in the mirror she handed me I could not believe how sophisticated and sexy I looked.
"Oh Brandi, I'm beautiful." I was stunned. "You are a regular cosmetics magician." I couldn't take my eyes off the mirror.
"Ok we're ready for Jimmy. When he comes, you go to the door and invite him in."
"I'm going to change." I said. "The tartan skirt and a white baby-T."
"Yes. Whatever feels comfortable, darling."
I was just finishing when the doorbell rang and Brandi buzzed him in and headed to the living room. She had put on a different CD, this amazingly hot make-out music, Euge Groove. I took a deep breath and checked myself in the hallway mirror. Satisfied with my appearance, I waited for Jimmy's knock. Which came momentarily.
I opened the door and saw a guy, about 5'4", who looked about 18 years old. I took the pizza from him and invited him in. "Hi I'm Fiona." I said. He looked at me uncertainly but I could see his erection through his jeans. As he walked by me his head didn't quite reach my shoulder.
"Jimmy." He said.
"Brandi was hoping you would stay a while." I told him. "She's in the living room. Care for a drink?"
"Yeah I'll stay for a bit; you got a coke? I can't drink and drive."
We left the pizza in the kitchen on the way and I gave Jimmy a coke from the fridge. I took his hand then and led him into the living room where Brandi was sitting on the loveseat.
"Hi Jimmy, you've met Fiona." Brandi said as she hooked the waistband of his pants and pulled him closer. Then proceeded to unzip and pull down his trousers. "I'm so glad you could hang out with us for a while. I told her I usually gave you a little gratuity when you delivered here." She said holding his cock in her hand. "I think she wanted to watch. You don't mind, do you?"
"No. I guess not." He was blushing a little and his voice was shaky but his cock was nice and stiff. Brandi gave it a little lick and he shuddered as a bead of juice seeped out of the tip. Jimmy groaned softly.
"Glad you're so open-minded Jimmy." She said and swallowed his cock to the hilt.
I sat in the armchair beside them, watching Brandi go down on him. She had taken off her top and Jimmy was fondling her pretty tits as she sucked and licked his penis. It was incredibly exciting and I was getting so keyed up I had to surreptitiously rearrange my own erect member. I watched them for a few minutes, getting more and more aroused.
"My friend is a little shy but I think she'd like to join us. You wouldn't mind if I shared you with her, would you?" Brandi asked.
"Of course not, Fiona." He turned toward me.
I stood and walked around Jimmy to sit beside Brandi on the loveseat. "Can I have a lick darling?" I asked. "Mmmmmmm nice cock baby." I said looking up at Jimmy as I took him into my mouth.
He looked down and said. "Nice lips Fiona. My cock is in heaven."
Brandi was caressing his buns as I stroked and sucked Jimmy, cupping his balls gently. I felt proud of the great strides I had made in such a short interval of time, adapting to my newly discovered homosexuality. "Fiona is a secret slut Jimmy; worse slut than me even. She would never have said anything herself but I know her well enough to know what she wants." Brandi told Jimmy.
"It's true." I said. "I love the cock."
"It's ok Fiona. I'm a slut too." Jimmy answered
"Well your in good company with us, slut." Brandi said, slapping his ass playfully.
"Are you kidding, I love delivering here." He laughed. "You give the best tips ever."
Brandi joined me and we ganged up on his cock, licking and nibbling from the sides. Jimmy stood there and took it like a man; a smiling, happy man. My own cock was throbbing and I could see Brandi was squirming too. I was wondering what it would take to get this boy to fuck our ass and then how to get our own cocks into his ass. There was no way he didn't know we were guys. He'd have to be the stupidest male in the universe. "What time do you finish work tonight, Jimmy?" I asked.
"9 o'clock, why?"
"It's Saturday night Jimmy, we're looking for someone to do us." Brandi winked. "Why don't you come back and party with us after work."
"That sounds like fun ladies." He answered licking his lips. "Should I bring anything?"
"Just yourself." She answered laughing.
Jimmy knelt in front of us and my heart leapt when he put a hand on each of our thighs. He was looking right at me and his hand was sliding up under my skirt, where my hard penis strained against the thong I wore. I could not move, I could not breathe; I was about to be discovered. His hand found my hard cock under there and wrapped around it.
"How long have you known, Jimmy?" Brandi asked.
"Are you kidding? I've always known. I thought you were hot from the start but I didn't feel secure enough to make a move." He answered. "Fiona, you tipped it for me. I have to get back to work now but I'll see you both about 9:30, right?" he asked.
We nodded, a little stunned.
Standing and pulling his trousers back up, he said. "At that time I'll be pleased to fuck you both."
"Ok that works." Brandi said.
"Yeah, I'd like that too." I added.
"Bye."
"Bye." We said together.
Jimmy left and we went to get the pizza from the kitchen. We'd been fooling around with Jimmy for about half an hour and it was a little cold by now but we were famished. We fell to and devoured it, chatting and laughing the while about Jimmy.
"That little shit. He knew all along." Brandi was laughing uproariously. "I've been blowing him for 3 months."
"Fancy that. Well better late than never." I laughed with her. "You know I kept trying to find something to say to get him to fuck us but I couldn't think of anything."
"He beat us to the punch alright." She laughed raucously. "I wonder if he sucks cock."
I imagined my cock in his mouth; it made me feel butterflies in my stomach. I added. "Mmmmmmm yeah that would be awesome, and doesn't he have a cute ass; I bet that's nice and tight too."
"Wow aren't you the little homo slut? You've come a long way in a short time, Fiona. I'm so proud of you."
"Thank you so much my darling, but I owe it all to my queerness mentor." I rejoined.
We smoked a joint and Brandi mixed us some martinis. Then we smoked another joint and more martinis. We decided to get dressed for him. We headed for the bedroom together, slightly tipsy. I changed into the green merry widow outfit with those sexy silk stockings. The thong I wore had hooks that allowed it to be removed very easily. Brandi wore matching red bra and panties, garter belt and fishnet stockings. She looked so hot like that. I came up behind her as she watched herself in the mirror, encircled her in my arms and snuggled up.
"You are the most amazing thing that has ever happened to me. I am a different person since I've met you and I love it." I said tenderly.
She stroked my arms as I held her. "Fiona baby, I'm just as happy to know you." She answered. She turned and gave me a kiss.
When Jimmy showed up later we were both nicely toasted. Brandi went to the door and brought him back to the bedroom. Maybe it was the liquor but I found him even cuter than before. I walked over as he came into the room on Brandi's arm. "Hi Jimmy," I said, taking his other arm. "I'm so glad you decided to come back."
"No chance of me missing out on your sweet ass, hot stuff." Jimmy said. "You look deadly in that outfit." He slipped his arm around my waist, his hand dropped to my ass and he gave me a friendly little squeeze. It felt wonderful.
Brandi turned Jimmy's face towards her and gave him a soft kiss. Jimmy responded, embracing her affectionately. We walked together to the bed, Brandi and I undressing him as we went. "Have you ever done anything like this before?" I asked.
"The first time I had sex with a boy I was 12. My neighbour Billy, he was 15. He fucked my ass and I loved it. I still sleep with Billy once in a while when he comes back from University. I've never slept with a cross dresser, but I have really wanted to."
"Where does Billy go to school?" I asked interested.
"SFU." He answered.
"Oh well." I said.
"And now you're how old?" Brandi asked.
"18"
"Good. I'm happy you could join us Jimmy. You need to know that you can be at ease with us."
"I know that. I never said anything before since I liked the play, the unmentioned, open secret between us. It was all so sexy and you seemed to enjoy it too." Jimmy replied. "But tonight, with the two of you. Well that was too good to pass up and I wanted you to know that I knew."
Brandi pushed him backward over the bed and we pulled his pants and briefs off. He was naked on the bed in front of us, pulling his socks off.
I undid my thong and pulled it off, releasing my cock. Jimmy licked his lips as he looked at it. Beside me Brandi was also taking off her panties. Jimmy was in for the ride of his life.
"I had never touched another cock before yesterday, Jimmy. Brandi picked me up hitchhiking and we just really hit it off." I said to Jimmy. He stared at me.
"No shit?" He asked. I nodded once. "Wow! Fiona baby you got some balls. And you, Brandi, are one persuasive lady." We all laughed at that one.
"I keep surprising myself, but the truth is I must have been bisexual all along without knowing. Brandi just opened my eyes, the minute I saw her I wanted to jump her bones. I'm not one for self-delusion. Once I realized I was attracted to her I had to re-evaluate. Brandi has been remarkably helpful. She's my mentor."
Brandi got into bed; positioning herself between his legs she spread him out and tucked a pillow under the small of his back. She put a condom on and squeezed some lube into her hand, basted his ass and started fucking him. He just let her have her way, moaning gently under his breath as he looked up at her. I put on a condom and climbed into bed too. Jimmy signalled me to come over. He grabbed another pillow and put it under his shoulders. He lay back down and arched his neck. Taking my legs he guided me so his head lay between my legs. He pulled me closer, opened his mouth and took my cock into it. It was amazing how much of my cock he could accept in this posture, almost the whole thing. "Oh Jimmy! You are a naughty boy and I love it. How is his ass Brandi?"
"It's to die for sweetheart. We've got us a little treasure here." She answered.
This was the sexiest thing I could ever imagine, and I could scarcely believe what Brandi and I were doing. Jimmy was moaning slightly as my cock filled his mouth and throat, his body arched. Looking down at him like this I resolved to try it myself.
Mmmmmmm the thought of a cock in my ass AND one in my mouth took my breath away. I leaned toward my beloved mentor and she bent forward for a kiss. Jimmy's hands were caressing her tits and she was stroking little Jimmy's dick as she fucked his ass. Beautiful. I bent further and started sucking the tip of his cock as she stroked it.
Brandi was fucking him hard now so I slipped out of his mouth and gave him a nice long French kiss as he grabbed my ass and massaged my asshole. I wriggled my butt for him, "Jimmy darling, that's lovely." I moaned into his mouth. "Where's the lube Brandi?" I asked.
"Here you go love." She said to Jimmy as he held his hand out and she squeezed a blob into it. He returned to my ass, greasing me up and probing with a finger. My sphincter muscle relaxed and let him in. He soon had me squirming like a worm on a hook. This kid certainly knew what he was doing. As he massaged my prostate, he reached out for my cock, slick with his spittle. His method was wonderful and utterly satisfying as he gently forced two more fingers into my ass and pumped my cock at the same time. I groaned and writhed as he finger-fucked me until I showered him with my hot creamy load. I cried out and my hips bucked uncontrollably until my balls were completely drained. I could not believe the sensations he had induced.
Meanwhile Jimmy was rapidly approaching his own climax under Brandi's tender ministration. I watched them attentively, desirous to add to my fund of `gai savoir' as I still considered myself a novice. Jimmy's cock looked ready to burst and I determined that I would catch his spunk. I took the head of it in my mouth and slid the tip of my tongue into the crack thereof. Substituting my hand for Brandi's I pumped him gently until I felt his sperm rush up his shaft and into my waiting mouth. Jimmy cried out his delight, mmmmmmm what joy we gave each other. What could be better? Soon after this Brandi pulled out, and removed the condom. I bent and took her lovely cock in turn into my mouth. When she shot her wad I swallowed every drop.
We rested for a few minutes, spent and content. Then discarding our accoutrements and wigs Brandi and I, we headed for the shower together to clean up. Once finished I was plain old Phil again, only smoother. Brandon found us some robes and we repaired to the living room for drinks and a spliff or three. Jimmy sat beside me on the love seat as I rolled. We three had become exceedingly familiar with one another, close. It seldom happens so quickly, but how rewarding when it does. I gave the joint to Jimmy and told him. "Spark it up." We passed it around.
"So, how did you like sex with a couple of transvestites?" Brandon asked Jimmy.
"That was the most amazing sex, guys. I especially loved when you were both doing me together."
"Yeah, I want to try that myself. Myself, I loved how you made me come, you are a very talented young man, Jimmy."
"Thank you. Can I ask you both something?"
"Of course." We answered.
"What are your real names?"
"I'm Brandon."
"And I'm Phil."
"Alright. Brandon I loved your tits from the first time I saw them and I've often wondered. Have you had work done, hormones or something? I haven't seen many girls with breasts as nice as yours, much less men. What's your secret?"
"I have no secret, I've never had anything done or taken anything. I'm just lucky." He smiled sweetly.
"Really?" Jimmy asked.
"Yes."
"That is absolutely amazing."
We made conversation like this and I rolled another joint, lit it and passed it.
"So you'd like Jimmy and me to fuck you together then." Brandon said.
"Oh yeah. I think it would be so good, a cock in my ass and another in my mouth. I want that very much."
"We can make that happen for you, baby." Jimmy winked.
"I'd like something too." Brandon said then. "I'd like both your cocks in my ass together. Can we arrange that?"
"Wow!" I said. I'd never even heard of that. My cock stirred at the thought.
Jimmy just grinned.
"Yes I think Jimmy and I are up to it. Right Jimmy?" I answered Brandon.
"Definitely."
"Good." Brandon said. "Very, very good."
"So you guys really just met yesterday?" Jimmy asked. "And you had never had sex with a man?"
"Yes. That's right." I answered. Brandon nodded silently.
"Wow. You really operate Brandon. Have you ever sold used cars?"
We burst out laughing.
"Excuse me I need another drink, anybody else?" Brandon asked.
We both said yes.
When Brandon returned, Jimmy was astride me and we were necking, robes open, rubbing our cocks together. He put our drinks down and sat watching us, playing with himself. We paused momentarily, and I held our cocks together in one hand while Jimmy turned around to grab our drinks. I caressed his lovely body with my free hand before reaching out for my drink.
"You boys are beautiful together." Brandon said.
"Why don't we go back to bed?" Jimmy said. "I want to help fulfil Brandon's fantasy."
I shivered at the thought of our cocks stuffed into Brandon's sweet ass. We finished the joint, drained our drinks and headed back to the bedroom for round 2.
I lay down on the bed first and Brandon straddled me, our cocks rubbed together momentarily, the total skin contact sending a jolt through me again. He put a rubber on my cock and lubed it up and then guided me into his ass as he lowered himself onto my swollen member. I played with his cock as he bent down to kiss me. Jimmy got into bed and crouched behind him, he grabbed Brandon's hips and slowly forced his cock in with mine. We fucked him together, long and slow. Jimmy's cock felt amazing against mine and it was so tight in Brandon's ass.
Brandon groaned and his eyes rolled back. "Mmmmmmm delicious. Oohooh fuck that's good!" He moaned. A shiver ran through him. I looked up from under him, watching the intense bliss. His ecstatic happiness was contagious and I felt waves of intense pleasure and affection for my new friends. I had never imagined such deep bonds being established so quickly. Time passed but I know not how much. We rode the waves of elation together, taking and giving freely. The music was perfectly suited to our lovemaking; it seemed to accentuate the intensely sexual atmosphere that reigned.
Eventually, Jimmy's fucking became more urgent as his climax approached, his breath chuffing and blowing hard and rough. Soon he pulled out, whipped off his rubber and spurted his load onto Brandon's big beautiful butt.
Brandon continued riding my cock while we frenched together again. I said. "Get on your back, slut. I want to fuck you properly."
He did this and Jimmy who had just cum, stuck his penis into Brandon's mouth to clean. I got between his legs and slipped my condom-covered cock back into his loose slippery asshole. I held his legs apart and Jimmy straddled his face to get into a 69 with him, licking and sucking as I fucked Brandon's ass. As I felt myself close, I pulled out, took off the condom and pumped my jism out all over his groin and Jimmy's face. It was a very sexy thing to watch. I brought my own prick closer and rubbed it against his.
Jimmy got up onto Brandon's belly, facing backwards and brought his penis into contact with ours. Wow, what a feeling; cocks just seem to love rubbing other cocks. He was right up against me; I had both my hands around all three of our cocks. He still had some of my semen on his face so I licked it off and frenched him with my own cum on my tongue. I had truly become a filthy slut and I loved it so much that I felt sorry I hadn't started earlier.
Brandon bucked and humped under us and a gush of sperm spurted onto my hands and mine and Jimmy's bellies. We rubbed the sticky mess around and then both drew nearer, lying next to Brandon on either side, coming together for a three-way kiss. Jimmy and I wriggled our cocks up against his thighs and bellies as our tongues licked and probed in one big sexy jumble. We dawdled like this slowing gradually and lay in a big sloppy pile. We felt such a deeply shared contentment as we slowly stroked and caressed, my lovers and I.
Jimmy was the first to get up and head for the shower. Brandon and I stayed a while in bed. "Did you like that, two cocks in your ass? How did it feel?" I asked him.
"Oh my God! Yes! It was terrific. I love getting stretched out once in a while. It feels like. I don't know. it's such a singular sensation. I can't really explain but it is deeply satisfying."
The expression on his face had awakened my curiosity and now I knew it would need to be satisfied. I had to know what it felt like. I also knew that I had two cocks with me now and who knew when that would happen again. I had to seize the opportunity. Round three would have to involve Jimmy and Brandon fucking my ass together. "Will you do me the favour, lover of mine?"
"Of course and I'm sure Jimmy will be just as eager."
"I'm so happy about all that's happened since we met. We've done so much and I've changed so much that it seems like years have passed since yesterday. I know I keep saying it but I can't believe the effect you've had on me. Thank you Brandon." I kissed him deeply and passionately, showing him the affection and respect I felt for him.
"You are very welcome lovely boy. I am pleased and surprised at the alacrity with which you've progressed. I've enjoyed myself tremendously and not just for the sex. This could be the start of a beautiful friendship my dear Phil. I want to keep in touch with you and I want you to feel free to visit."
"I want the same thing. Whenever you're in Nanaimo you can stop in and see me as well. I live on my own so you can stay as long as you like." I told him in turn. We got up then and headed for the shower too. Jimmy was just getting out when we got there. I gave him a soft kiss and gently fondled him before getting in the shower myself, as I closed the curtain I saw Brandon and Jimmy were kissing.
I lathered up under the spray from the showerhead, loving the hot water's soft slippery caress. Brandon joined me and I washed him gently, paying special attention to his ass. Raising his foot to the side of the bath and turned away as he spread his generous cheeks. I gently stroked his anus; it was still soft and loose from before. It parted easily under my finger and he shivered as I fondled him soothingly. "I love to feel your hands on me. You make me feel so good, Phil." He said softly, turning to kiss me again. My lips parted as I felt his tongue. The water raining down on us, it was all so sensual. We rinsed off the suds and stepped out of the shower to towel off.
We strolled out to the living room, naked as jaybirds, where we found Jimmy, also naked, rolling a joint. Brandon sat in the armchair and I sat in his lap, wrapping my arm around his neck. We kissed ardently as his hand found my penis and massaged it into life. Jimmy watched us as he rolled, his own cock hardening between his legs. I loved to be watched, it made me feel deliciously dirty. I stood, moving over to get my cock lined up with Brandon's mouth. His hand slid between my legs, cupping my ass to pull me close, his middle finger, sliding into my crack. "Mmmmmmm that's fabulous darling." I said.
"Well dear boy I love to do you. Any way you want to be done." He answered.
Jimmy had lit the joint and passed it to me. I toked and passed to Brandon. "Would you fix me a martini darling Brandon?" I asked.
"Of course Phil, anything you want baby." He set about doing this. "Jimmy?"
"Please."
Brandon nodded and soon produced three cocktails. We toasted our beautiful closeness and drank together.
With all three of us sitting around naked things soon heated up again. I bent over to suck Jimmy's cock, presenting my ass to Brandon; hoping he would take the hint; I wiggled it around a little and spread it out with one hand. Sure enough I felt his hands on my ass, spreading me wide open, he licked my anus, pushing his tongue into me. I gasped at the sensation. My hips bucked and I shuddered from head to toe. He grabbed my cock from beneath as he kept tonguing my ass mercilessly. I could not believe what he did to me. His fingers soon joined his tongue as he probed my asshole softly but firmly. I felt myself loosening under this magnificent tongue-lashing.
After that his cock slid home with ease and I found it was every bit as enjoyable as I had hoped earlier seeing Jimmy in this position with a cock in his mouth and another in his ass. I still wanted to experience two cocks in my ass though. "Brandon baby, would you sit on the loveseat so I can ride that beautiful cock of yours? Then Jimmy here can get behind me and stuff his own cock in there with you. Hmm?" I asked.
"Of course sweetheart." Brandon said. We broke apart momentarily and after Brandon was sitting I straddled him and lowered myself onto his penis. He slid right into my loose slippery asshole.
"Jimmy baby, I'm ready for you." I said.
He positioned himself behind me; I felt his cock sliding along the crack of my ass. Then I felt him pushing his cock in with Brandon's. At first I thought my anus wouldn't stretch anymore but after a few seconds I felt his cock pop suddenly into my ass. It was wonderful, here I was sandwiched between these two sexy men and both of them were fucking me. Jimmy's cock started pumping and it got even more intensely satisfying. I'm not sure if I said anything coherent at this point, I simply lost control as waves of pleasure washed over my consciousness. I could feel pre-cum juice just flowing out of my cock, like a prolonged orgasm. Brandon and me were slippery with it where our bellies rubbed together with my cock between them. In the end I cried out as I came again from their fucking me. It was the most intense orgasm yet. They kept pumping me though, both of them and I soon came again, I could not believe what they were doing to me. Then when I thought I couldn't take anymore, I felt Brandon stiffen and come under me, soon followed by Jimmy behind me. We were all panting now, covered in sweat. We caught our breath slowly and Jimmy's cock plopped out of my loose anus. I sighed contentedly.
"That was amazing, boys; the monster-fuck of my life. You've made me feel like I've never felt before. Thank you so much." I told them.
"Anytime darling." Brandon said.
"Yeah, that was fun." Jimmy chimed in. He sat in the armchair.
I stayed on Brandon's lap. His cock had slipped out of my ass. I snuggled up to him, my head on his shoulder with his arms around me. I would never have imagined feeling this way about a man but I wanted to stay there forever, in the comfort of his arms. I felt a delightful lassitude combined with a much deeper understanding of my unconventional behaviour. I was at peace.