Jon had invited me to spend another weekend at his place with another of his friends. I always find his friends to be interesting so I accepted. Jon had given me a garage door opener and a key to his home after my first visit. He met me as I parked my car in the garage. He was wearing his usual skimpy European swimsuit. “Hi Brad, you’re in the same bedroom as before. Get changed as quickly as you can. I can’t wait for you to meet Mai. Jon turned and disappeared into the house.
I carried my bag upstairs to the bedroom with the skylights. Jon must have had a plan in mind because there was an electric blue European style swimsuit lying on a note on the pillow. I picked up the suit and read the note. “Lover, please wear this. I’m dying to see you in it. Jon. P.S. Your thin running shorts are too tacky.”
The note made me laugh. I stripped then put on the swimsuit. It seemed to be even skimpier than Jon’s. I don’t consider myself to be extremely well endowed or heavily hung, but it took some doing to get my cock and balls arranged and comfortably tucked into the suit. I looked at my reflection in the mirror. The bulging pouch made it look as if I was carrying a very nice package.
I walked downstairs and through the house. I suspected Jon and his friend were in the sunroom. As I entered, Jon stood up and got out of the hot tub. “Gawd, Brad! You look so hot! Doesn’t he, Mai?”
“Yes, he does.” Mai stood up in the hot tub and extended her hand. “Hello, I’m Mai.” I took her hand. She had a firm grip. “Jon, after you tuck your eyeballs back in, would you be a dear and get Brad and I a glass of wine?” Mai still held my hand. “Please join us.”
I stepped down into the tub. Mai was a black woman in her early thirties. She was wearing a modest two piece swimsuit which didn’t hide the fact she had a nice figure. Mai had large dark eyes and what a smile! When she smiled, the room lit up.
Mai and I settled into the warm water. Jon returned with a tray with three glasses of wine. He set the tray down then slipped into the tub. He handed Mai and me our glasses then he took his and made himself comfortable . We sipped our wine and chatted.
Mai asked, “Brad, how did you and Jon meet?”
“We’re both in pretty much the same line of work. We met at a hotel while working out in the fitness center.” I didn’t tell her that part of the workout was a group sex session with Jon and two other men and that I had sucked each of their cocks several times, all three of them fucked me and I was drenched in their cum when we finished. “We hit it off and just became friends. How did you meet Jon?”
“I’ve known Jon for a number of years. We also met through work and became friends. I’ve had some serious issues in my life and Jon has been there for me and has helped me work through them. So Jon is a close and dear friend.”
As Mai and I chatted, Jon got out of the tub and sat on the surrounding deck. Mai ran her hand up the inside of his leg. She looked at me, “I understand you are able to do something that I’ve never been able to do and, certainly, something very few other people have done.”
“Jon tells me you can swallow him completely.”
I looked up at Jon. It wasn’t a secret that I could deep throat his slim eleven-inch dick, but I was rather surprised he discussed our sex life with his other friends. Jon smiled, “I get so excited when I think about my cock being all the way down your throat that I can’t keep it to myself.”
Mai touched my arm. “I’ve tried numerous times. Would you show me how you do it?”
I looked at Jon again. He was peeling his suit down. Then I looked at Mai. “Only if you help.”
Jon slipped out of his suit. His cock was rising in anticipation. I pushed his knees apart so Mai and I could get close to his crotch. “Jon’s eager to go, but I like to start with his soft cock. He gets hard as I suck and his cock extends itself down my throat. If we’re playing with friends, it always surprises them when I pull his long hard cock out of my mouth.”
Mai licked the underbelly of Jon’s cock. “It sounds like a magic act except you unswallow the sword.”
I laughed and leaned in to lick the side of Jon’s cock shaft. “Let’s get him slicked up and I’ll try to swallow him for you.”
Mai and I took turns licking up and down his cock and kissing and sucking his cockhead. I laid Jon back on the deck. I was still in the tub so I had him turn so I could line my mouth and throat up with his hard cock. Mai watched as I slipped my mouth over his cockhead. I tightened my lips around his shaft and began to pump my mouth up and down his cock.
My saliva lubricated his shaft so I could take a little bit more of him into my mouth and throat each time I pumped down. I took time to kiss, lick and suck his cockhead and ball sac. There was no reason I shouldn’t enjoy myself. Mai and I passed Jon’s cock back and forth between swallows.
When I felt I was relaxed and ready, I took Jon’s cock from Mai. After running my tongue around the cockhead a few times, I pushed it into my mouth as I began to swallow Jon’s cock. I slowly worked his hard length down my throat. Mai put her face down beside mine. I felt her breath on my cheek as I ate Jon. She lifted his ball sac just as my lips touched his pubic hair. Mai kissed my cheek.
I pulled back to his cockhead, then using my lips I inched his cock back down my throat. Mai continued to cup his balls. Jon groaned each time I reached the base of his cock. I didn’t want to make him cum so I finally backed off and let his cockhead fall from my mouth. Mai licked the length of Jon’s cock shaft then she kissed me.
“I wouldn’t have thought that was possible. You deserve a reward for your efforts. Stand up.” I stood. Sucking Jon had given me a hard-on and my cock was trying to escape the confines of the skimpy swimsuit. Mai tugged the waistband down and released my cock. She gripped my cock and looked up at me, “I can tell you enjoy sucking cock.” Then she pushed her lips over my cockhead.
Mai stopped blowing me just long enough for me to take off my suit and to sit on the edge of the hot tub. She licked her way up and down the shaft. She had a thing for sucking the cockhead really hard while she gently squeezed my balls. I didn’t want to cum just yet, so I touched her face.
“Let’s get comfortable some place. I’d like to eat your pussy.”
Mai took her mouth off my cock and looked at me, “You may when I have one.” She stood up and began to push her swimsuit bottom down her legs.
Jon grinned as it dawned on me. Mai was a pre-op transsexual. She stepped out of the bottoms and threw them onto the deck. She pulled the suit top over her head and tossed it onto the deck. She placed her feet apart and stood with her hands on her hips. I was gazing at a shemale. Mai had soft wavy hair, large eyes, a pert nose and full soft lips. Her breasts were cone shaped. Each pierced nipple held a gold ring.
Her hips were full and her tapered thighs disappeared into the warm water. There was a small triangle of curly pubic hair below her rounded belly. Mai looked straight at me. “Do you like what you see?”
“Yes. Very much.” Her thighs framed a nice uncut cock which hung above a dangling shaved ball sac. I slipped down into the water and got on my knees in front of Mai. I picked up her cock and pushed the foreskin back to reveal a brownish pink cockhead. I licked the pee hole then pushed all of her cock into my mouth. With my tongue, I pressed and rubbed her cock while my nose pressed into her pubic triangle.
I tipped my head to look up at Mai. She smiled at me then, placing her hands on my shoulders, began to fuck my face. I held my head still as her stiffening cock slipped in and out between my lips. Her nuts, in their shaved sack, dangled four, maybe five inches, below the root of her cock. Each time her pubic bone bumped my lips, her nuts would swing and tap me under the chin.
I took her cock out of my mouth and licked around the cockhead. I heard Jon say we should find a more comfortable place. Mai helped me to my feet. We got out of the hot tub and followed Jon out of the sunroom, across the patio and onto the lawn where he stopped by a chaise lounge.
Mai lay down on the lounge. Jon grunted as she grasped his cock and pulled him to her mouth. As she began to suck Jon, she put her feet flat on either side of the lounge and splayed her thighs open. Since I wasn’t finished with her cock, I kneeled on the end of the lounge and resumed sucking her. In my mouth, her cock swelled to a firm six or seven inches of comfortably thick meat. Her balls, in their long stretched sac, hung down between her thighs where they were sort of hidden and hard to get to.
I felt the lounge move. I looked up. Mai had taken a break from blowing Jon as she lowered the back of the chaise. She lay back and tilted her head. Jon straddled her, facing me, as Mai guided his cock into her mouth and throat. I watched as Jon slowly thrust about nine inches of hard cock down her throat. She pulled on her nipple rings as Jon pumped his long meat.
I returned to Mai’s cock. I did a lot of licking up and down her cock shaft so I could watch her swallow Jon. Jon pulled almost all the way out of her mouth. Mai took a deep breath then swallowed his cock again. Jon pushed as deep as he could then he braced his hands on his knees. His ball sac tightened visibly as he began to cum. Mai received several wads deep in her throat before Jon pulled out of her mouth.
I clamped her cock between my thumb and forefinger. She may have been ready to cum but I wasn’t ready for her to cum. Mai gasped for breath as Jon shot a few more wads. The first landed on her chin and the rest splashed around her breasts.
Jon straightened up. I arose on my knees so I could lean forward. Jon held his cock still as I took him into my mouth to suck him dry. When I couldn’t get anymore cum from Jon, I looked down at Mai. She was watching me. I licked his cum off her chin and kissed her. She sucked my tongue into her mouth. I lay down on top of her.
We pressed our hard cocks together and began to grind our hips as we sucked each other’s tongue and explored each other’s sucking mouth. Mai and I broke the kiss. Jon was gone. She wrapped her legs around mine and we were exchanging little kisses when Jon returned with a tray of cold drinks.
“You kids better slow down and take a break.”
Mai and I untangled ourselves and sat up on the lounge. Jon seated himself on the grass. I rubbed Mai’s back and she leaned against my shoulder as we sipped the drinks. I kissed her cheek.
“I’d like to be your friend. May I?”
She smiled her bright smile. “Yes, you may.” She put her hand on the back of my head and kissed me. Her tongue slipped into my mouth and we began to suck tongues. Jon stood and put his arms around both of us. His face was next to ours and soon all three of us were sucking each other’s tongues like they were little wet cocks.
We sucked and kissed until Jon announced we should break this off because it was time to change for dinner.
We looked at him “Change for dinner?”
“Yes, I thought we should dress for dinner. In each of your rooms you’ll find a selection of dinner wear. Jon was smiling as he told us this. “Dinner is in one hour.’
He picked up the glasses and trays and Mai and I followed him into the house. We picked up our wet suits as we passed the hot tub. When I got to my room, I rinsed the suit then decided to take a shower. I took my razor and lather in with me. I shaved for the second time during the day. And I gave myself a tremendous hard-on while shaving my cock and ball sac. After drying off, I put my shaving gear away in a bathroom cabinet. Jon certainly was prepared to take care of his guests.
There were new toothbrushes, combs, razors, shaving cream, toothpaste, after shave, cologne, and deodorant carefully arranged on a shelf. A drawer in the vanity contained an assortment of packaged condoms. Another drawer contained several pre-packaged enema solutions. Jon seemed to make sure his guest rooms were equipped for all contingencies. There was also a coiled tube with a nozzle on one end and an adapter that fit over the bathtub waterspout. A so-called male douche.
I closed the drawer and looked at my reflection in the mirror. My hard-on had subsided to half-staff. It was just at the right stage to dangle over a kneeling lover’s face and slowly feed into his or her warm wet mouth. I sighed. Maybe later.
It was getting close to dinnertime and I figured I’d better get dressed. There was nothing in the closet so I checked the dresser drawers. One drawer was filled with an assortment of underwear, thongs, g-strings, pouches, etc. This was Jon’s idea of dressing for dinner. I tried on a thong, which was uncomfortable, and settled on a yellow g-string that was set off by my tan.
Mai and Jon were in the dining room. Jon had his substantial tool tucked into a maroon velvet thong. He had a jeweled pendant clipped to one nipple. Mai was wearing a pair of beaded fringe black panties. She had a thin gold chain around her waist and she had connected her nipple rings with a second thin gold chain. We were the most decadently dressed dinner party I had ever seen.
During dinner Mai talked about how she had struggled with her gender identity for years. She was an only child. When she was little she liked playing house with the girls but she equally liked playing cops and robbers with the boys. Her struggles really began when she was a teenager. She went out for all the high school boy’s sports but really didn’t enjoy them and she discovered she enjoyed experimenting with make up and wearing her Mother’s under clothing.
“One weekend, when I was a junior in high school, I had the house to myself. My parents left early on a Saturday morning for a weekend retreat with our church. I went upstairs and showered, dressed, then went into my parent’s bedroom. I looked through Mom’s lingerie drawer. It held the usual panties, bras, panty hose, slips, and other under things. There were some sexy silk and satin panties and a couple of sexy bras, but beneath it all I found a small plain envelope which contained a single key.”
“It looked like a key for a suitcase lock. I went to the basement. All of the luggage stored there was unlocked. So I went back upstairs. I looked in my Mother’s closet and found nothing. I looked in my Father’s closet. Way back in the corner, under a pile of old shoes, I saw a large suitcase. I dragged it out and hoisted it onto the bed. The key fit the lock.”
When I opened the suitcase, there was a French Maid’s costume right on top. I took it out. The suitcase was full with costumes and sexy under things. There were bras with nipple cutouts, crotchless panties, net stockings, body suits and so on. I also found a red leather pouch with a hole cut in it and all sorts of cock straps, nipple clamps, several vibrators and dildos, and a vacuum pump. I was looking at my parent’s toy chest.”
“There were several manila envelopes at the bottom. I picked up the thickest and opened it. It was full of instant photos of my Mother. In the pictures, she was wearing the costumes and underwear in the suitcase. She looked cute and sexy in the French Maid costume. There was one series of her in a nurse’s outfit. In each picture she takes off one item of clothing until she is wearing only the nurse’s cap, a white garter belt, white stockings and white shoes. She looked so good with her brown skin being set off by the white under things. And she looked hot!”
“I found the nurse costume. I hurriedly undressed and put on the garter belt, nylons, panties and bra. I looked in the mirror. I thought I looked sexy, but not nearly as sexy as my Mother. There were several more envelopes of pictures. One was full of glamour shots of my Mother. Most were discreet nudes. Some were shot outside and others looked like they had been taken in motel or hotel rooms. A lot of them were full frontals of her standing, sitting and lying down. There were several raunchy split beaver shots of her with her fingering herself and others with her pussy, ass and mouth stuffed with various dildos, vibrators and plugs.”
“A second envelope was shots of my Father. He was in his underwear or swimsuits in some of them, but most of them were nudes. He had a hard-on or was stroking his cock in many of them. There was a series of him wearing the red leather pouch and various cock straps and rings and using the pump and various plugs. “
“The last envelope contained pictures taken in a hotel. There was a series of my Mother and another woman. They were kissing and going down on each other and 69ing and sharing a double dildo. There was a series of each of the women sucking and fucking the two men, individually and together. The last series was of my Father and the other man. They are lying on the bed and jacking off.”
“I had a tremendous hard-on from looking at all this and when I came to the last picture ser, I shot my load into the white nurse’s panties. My Father was standing and the other man was sucking his cock and licking up the cum from the jack off session.”
Mai paused in her narrative. All of us had stopped eating as she talked and Jon and I listened.
“What did you do?”
Mai laughed. “First, I washed and dried the nurse’s panties, then I spent the rest of the day trying on the costumes. I loved the net stockings. I also worked on my makeup. I hadn’t eaten all day. And by the time I fixed something to eat, I was exhausted and I crashed, makeup and all.”
“The next morning, I put everything away. Then I showered and shaved, including my legs and underarms. I didn’t have much body hair so I didn’t worry about shaving it. I felt like I was being crazy, but I wanted to dress up as a woman and go out of the house. I was slim and about my Mother’s size. I put on a jock strap to hold my cock and balls up and then a pair of her panties and a bra. I stuffed the cups with nylons. I got out one of her wigs, a short curly one.”
“I did my makeup. Just a light color of lipstick, some blusher and eye shadow. I put on a pair of her shorts and a blouse and sandals. I adjusted the wig. I thought I looked good but something was missing. I decided to paint my toenails. I ended up doing my fingernails too. When the polish was dry, I got one of her little clutch purses, my car keys and money and dark glasses. On the way out I checked myself out in the hall mirror. I decided I looked good with breasts.. After undoing the top button on the blouse, I took a deep breath and walked out the front door.”
“No one was watching. I backed the car out of the garage and then decided where to go next. I drove across town to an area where I was pretty sure I wouldn’t see anyone whom I knew. I stopped at a self-service gas station and filled the tank on the car. No one paid any special attention to me. The cashier called me ‘Miss’. Next I went to a mall. I got a little hard-on shopping for woman’s underwear.”
“When I was walking out of the mall, I recognized some boys from my high school. They were hanging out around a car parked at the curb. It was too late to change direction so I just kept walking. One of the boys, who was in several of my classes, whistled, ‘Hey Baby, Watcha’ doin’ tonight?’ I smiled at them and kept walking. There was laughter, but I heard one of them say something about nice tits and another said something about fine legs and ass.”
“When I got in the car, I had a major hard-on. I felt good. On the way back across town, I stopped at a super market and picked up some orange juice and other things. I flirted a little with the bagger when I checked out. As soon as I got home, I undressed, except for the bra and my ‘tits’, and jacked off into the bathroom sink. My parents were going to be home later so I washed all of my Mother’s clothing and put it away. I made sure the suitcase key was where I found it. While the clothes were washing I removed the nail polish and make up. And that’s how I discovered I liked being a girl.”