Elegant and Effeminate

by Gloria Marshall

 

We all have our fetishes, and some of us have our subfetishes as well. One of my most powerful ones stems from a long-term fascination with my stepmother's dressy bracelet watch. And, in fact, now that I am building my own wardrobe, my jewelry collection includes several fashionable ladies bracelet watches. However, although I have looked all over I have never seen one like my stepmother's.

So—given that history, when I saw a dressy bracelet watch very similar to hers one recent weekend, I was fascinated with it. The sudden fascination didn't surprise me at all—but what did surprise me was that the ultrafeminine item belonged to a man.

I saw him at a friend's party and was immediately drawn to him due to the elegant and effeminate watch around his wrist. I very badly wanted to wear it. I remember thinking: I'd do almost anything. . . .

Gary and I had been chatting amiably for awhile. I kept stealing glances at the lovely piece of jewelry on his wrist, though, and finally decided to say what was on my mind. "That's an exquisite watch," I said. I immediately wanted to take back my words. Exquisite? Didn't that sound just a little over the top?

However, he didn't seem the least bit concerned at my choice of words. "Oh, thank you," he gushed. "It's a present from Mother. It a mat—" he began, but cut himself off. "It's, um, it was a college graduation gift," he concluded lamely, a bit flustered.

I hadn't meant to embarrass him, so I replied sincerely, "What a lovely present." "Yes, it was" he said, looking at me. His expression changed then, and he glanced around the room. "Would you like to—ah—try it on?" he asked quietly. I stared at him, not knowing what to say, but my transvestite side spoke for me before I could really think about it. "I'd love to," I said a little too quickly, then I blushed and glanced around the room as well. "Maybe—um, maybe someplace less . . . crowded?"

He blushed prettily, then walked from the room. I waited a moment, then followed him. He led the way to the stairs, then upstairs to the guest bedroom where the coats were all piled on the bed.

As soon as I walked in he quietly closed the door behind us, walked to the bed and sat down, and began to take off his watch. I was nervous, but what the heck? I'd gone this far, after all. And I really did want to try on his watch. I walked to the bed and sat beside him.

His expression had changed again, and now he looked rather amused. He looked down at the watch he was now holding in his hands, then gave me a sidelong glance. "I have a sixth sense about these things," he said. "As soon as I saw you, I thought you looked like a sissy. That's what this is, you know," he said with a laugh, holding out his watch. "This is my 'Sissy Watch.' That's what Mother calls—"

He stopped again, embarrassed, and looked down at his lap. He absentmindedly put his watch back on, then looked up again. "It really does feel sexy," he whispered. He took my hand and placed it on his wrist. "Oh," I said, looking down, "It does, it's warm and supple, and—" I looked up in time to see Gary leaning over to kiss me. I gasped, and just as our lips touched I felt him reach down with his other hand and lightly brush his fingertips across the bulge in my jeans.

My orgasm was sudden and powerful. I reached behind Gary's head with my free hand and pulled him to me, lustily French-kissing him. We kissed and nuzzled and fondled like dates at the prom. When we started dry-humping he finally came, and as we lay pressed together I could feel his orgasm spurting through the gauzy cotton material of his slacks.

The doorknob rattled just then and we froze. There was a pause, then footsteps walking away, and I let out my breath. I for one was not keen on being caught in such an uncompromising position, so I suggested we put on our coats to cover our stained clothing and leave right away. Gary quickly agreed, so we headed out the door. I got in his car, and we drove to his house, which was only a few blocks away.

Once there, giggling like schoolgirls, we washed up, and Gary lent me sweatpants and a T-shirt, then we went to sit on his living room couch and started kissing again. At one point when we came up for air he laughed a little and said, "I almost forgot about this. You still want to try it on, don't you?" He took off his watch and took my hand in his, then draped the surprisingly heavy item over my slim wrist and clasped it in place. My erection suddenly strained against the thin material of the shiny nylon sweatpants.

Just then the front door opened and Gary's mother walked in. She breezed into the kitchen, taking in the scene in the living room with one sweeping glance as she went by. "Hello dear," she said. "Who's your little friend?"

She set her groceries down and reappeared from around the corner. Gary blushed yet again—why did it turn me on so when he blushed?—and said, "This is Gordon, Mother. Gordon, my mother—I mean, Selena." Selena smiled and held out her hand, and I smiled and shook it. She glanced down at her son's watch on my wrist and frowned. "Is that yours, Gary, or does your friend just have the exact same taste in jewelry?"

"No, it—ah, it's mine," Gary murmured. Selena gave him a concerned look. "Oh, Gary, I'm sorry dear, but know I gave you very strict instructions regarding your jewelry. You know you'll have to be punished, don't you?" He looked down at the floor. "Yes, ma'am," he said meekly.

She then turned to me with an apologetic look. "I'm sorry," she said. "I don't allow Gary to lend out some of his things. I'll have to ask for that back." She took my unresisting hand and took her son's watch from my wrist. This was such a surreal situation I had no idea what to think or do, so just sat there mutely. However, I did notice Selena's watch just then. It was a perfect match to her son's—they were part of a "his-and-hers" set. That seems odd, I remember thinking. I thought only married couples bought such sets.

Selena put the watch back on Gary's wrist, then took his arm and started to lead him out of the room. She stopped, though, and turned to look at me. "Well, you may as well come along," she said. I found that I couldn't say no. I stood and followed mother and son down a long hallway, then into a large and very feminine bedroom.

"I believe you know the drill, dear" Selena said as she sat Gary on the bed. He nodded, and immediately began to take off his clothing.

"Now, while we're in the bathroom, why don't you amuse yourself looking through my armoire," she said to me. "If your fascination with my son's 'Sissy Watch' is any indication, you'll find a number of items that should, ah, interest you." She smiled in a faintly mocking way, then turned and led her son, now stripped down to his bikini briefs, into the adjoining bathroom and closed the door.

Was this a dream? I thought as I walked to Selena's large armoire. I opened the top drawer and moaned softly. Inside were several dressy watches which fit even my fussy criteria. I picked up one, then another, draping each one across my wrist. I finally picked up the first one I had seen, a dainty, elegant one with a baguette case. I gazed at it for a moment before slipping it over my hand and clasping it in place. I looked in the mirror, and felt the same sensation I had experienced twenty years previously.

As the first shudder went up my spine the bathroom door opened and Gary walked back into the bedroom. Still wearing Selena's watch I turned to look at him and my eyes widened.

He had a fluffy towel wrapped around his hair, turban-style, and was wearing a short-short pink satin kimono and matching high-heeled slippers with marabou trim. His legs and chest were smoothly shaved.

Selena followed him into the bedroom and glanced at me, then smirked at the item of jewelry on my wrist. "Oh my, you really are a priss, aren't you?" she asked. She walked by me, stroking my cheek with her fingertips as she passed. "Now watch, and learn what happens when I punish someone," she said.

Actually, Gary looked like he was looking forward to his "punishment." Selena sat him at her vanity and began to give him a thorough makeover. I just stood there and gaped. I have never been more turned on in my life.

I had never been attracted to a man before, but Gary was not really manly. Just the opposite—he stood perhaps 5'3" and couldn't weigh more than 100 pounds. He had flame red hair and delicate, even girlish, features. Even after a simple foundation and application of blush he looked more like a woman than a man.

Selena had already fitted Gary with long, curved glue-on nails and two coats of lipstick red polish, so to let them dry she now brought loving devotion to her son's elaborate makeover. Twenty minutes later, when she finally finished up with a thick coating of creamy red lipstick the illusion was complete. When I looked at him, instead of a swishy twentysomething man I saw a beautiful woman.

Selena was far from done, however. She stretched a nylon wig liner over Gary's hair, then settled a long, silky black pageboy wig into place. "Put on your lingerie, dear, and I'll get your dress and heels out," she said, going to the closet.

Gary contentedly complied, and expertly dressed himself in a black pushup bra, a black nylon padded girdle, and long black pantihose. I belatedly realized that the only really well developed muscles Gary had were his pectorals—he must do very specific exercises to develop them and still retain such thin arms, I thought. The bra actually gave him a little bit of cleavage, and strategic padding gave the illusion of a realistic bustline.

He then wriggled into a black satin camisole and a short white ruffled mini-petticoat, then looked up expectantly. Selena was holding up a black satin minidress by the shoulders, so her dainty son walked to her and gingerly stepped into the flared skirt. Selena tugged the skirt up around his padded hips, then helped him carefully guide his long-nailed hands through the puffy short sleeves, and then finally zipped him up.

As Gary put on high-heeled black patent leather pumps his mother opened a drawer of her vanity and took out a frothy stack of lacy garments. She had him stand, then tied a white lace apron around his waist, then put on the matching wide collar and cuffs. A lace cap completed his maid's outfit.

"Model for us a bit now, dear," Selena said. She walked over to me (I thought she had forgotten I was there) and slipped an arm around my waist. "Isn't she pretty?" she asked me, gazing at her wisp of a son as he minced back and forth with practiced ease in the 5-inch heels. "He's gorgeous," I said truthfully.

She turned and leaned to whisper in my ear. "Would you like to be?" she asked softly. "Gorgeous, that is?" Her hand had wandered down to my nylon clad bottom. "Oh," I said, "I don't—I don't know." "Oh, go on—you're already wearing a pair of my sweatpants," she said teasingly. "Why don't we see what you look like in something less casual?"

I turned to her and she suddenly kissed me, quite passionately but for only a couple of seconds. "I believe I'll have my maid dress you," she said. "Take off your clothes. Oh, Elizabeth," she said, turning to her feminized son, "when he's undressed take Gordon to the bathroom and prepare him for a formal dressing."

Elizabeth's eyes widened with pleasure. "Yes, mum," she said, then curtsied, and stood by as I stripped myself of shoes, socks, T-shirt, and sweatpants. "She" then took my arm and led me to the bathroom. I noticed that Selena had opened her closet doors and was looking critically at a row of dresses.

I was bathed, shaved, powdered and perfumed, then fitted with a cunning little gaff that kept my telltale male bulge in check. I put on the same kimono and high-heeled slippers that Gary had been wearing, wrapped my hair in a towel, and carefully strutted back into the bedroom. I was trembling with excitement.

"Give him a makeover now, please," Selena said to Elizabeth. "I've set out an eyeshadow palette and lip color. And Elizabeth—do a . . . thorough job." Elizabeth curtsied again and said with undisguised glee, "Yes mum. Thank you, mum." She turned to me and smiled broadly. "This will be fun," she murmured, sitting me at the vanity bench and settling down next to me.

She wouldn't let me see the mirror for the longest time, but I didn't mind as I was quite content watching Selena. She had chosen several sumptuous gowns and laid them on the bed, and now she was critically eyeing them. Finally she seemed to have decided on one, as she began to select lingerie, then my heart skipped a beat as she began opening drawer after drawer of her armoire. She reached in and began to take out something, but I didn't see what it was as Elizabeth just then turned me to face the mirror.

"Oh . . . oh . . . oh," I said, trying to catch my breath. While I'm not as naturally girlish as Gary I am still effeminate. Expertly made up, I made a surprisingly convincing woman. Perhaps it wasn't the face of a cover girl, like my sissy friend—but I was very definitely pretty. I reached up with one long faux nail and brushed a hair from my eye and sighed contentedly.

The wig that Elizabeth now put on me and began to arrange was a lovely honey blonde. It was prestyled in an formal hairdo, with soft ringlets that brushed my cheeks. She fussed with it for the longest time, making sure it was just so, then had me stand up and turn around. Selena was holding a bra.

"Take off her robe," Selena said. Soft fingers slipped the satin kimono off my shoulders, then I felt myself pushed gently forward. "Hold out your arms, dear," Selena said. I did so, and allowed her to dress me in the black satin boned longline bra. She started to lace up the back, but snugged weighted breastforms into the cups of the bra before lacing up to the top.

Next was a waist cincher, which also laced up the back. Like Elizabeth, I was also fitted with padded hips and bum.

I then sat on the bed so Elizabeth could roll a pair of nude stockings up my silky smooth legs, hooking them to the garters on my girdle. The feel of her dainty, long-nailed hands brushing against my inner thighs was delicious, and I gave her a burning look. She returned it, but then remembered her training and demurely turned to Selena. "He—I mean, she's ready for her slipgown, mum," she murmured.

Selena smiled at our expressions. "Good," she said. "Stand up please—if you think you can," she said to me. I did so and, as instructed, raised my arms so that she could dress me in the floor-length black silk satin slip. It flowed against my silk-clad legs in a delightful way.

I turned then to see mother and son holding up the dress Selena had chosen, each one holding a shoulder. I stepped into it just as another deep shudder ran up my spine. It was a long column dress in royal blue satin jacquard with long fitted sleeves. It was a dream to put on, and when Selena reached down to start on the numerous faux pearl buttons running up my back I found myself sighing with every button.

It slowly formed itself around my now-curvaceous frame, and when the top button was fastened I saw that it fit almost as though it were made for me. Oh, I'm so glad Selena and I are both size 8, I thought dreamily.

Selena took my arm then, and helped me stand as Elizabeth knelt and slipped matching pumps onto my feet. They fit, but were a little tight in the toe. I didn't mind.

Selena now walked to her armoire and opened a deep drawer. She took out a pair of oversized gold-and-sapphire earrings and handed them to Elizabeth. "Put these on her," she said, "then hold her ringlets up." Elizabeth clipped the earrings in place then I felt her cool, dainty hands brush against my cheeks as she held my plethora of ringlets out of the way. Selena then draped a wide supple brushed gold-and-sapphire choker necklace around my throat and clasped it shut.

"It's the perfect final touch," Selena said, beaming. "You may look in the mirror now."

I glided across the room to stand in front of Selena's full-length oval stand-up mirror. I ran my hands up and down the sexy gown, and fondled all the lovely jewelry I was wearing. Oh my. It was all quite distracting.

"Doesn't it feel . . . wonderful?" Elizabeth asked, coming up behind me. She stepped up to me and snaked her hands around my waist, then proceeded to kiss the nape of my neck as her delicate fingers tickled and caressed my satin-covered stomach and thighs.

I squirmed with delight, but then I quickly glanced over Elizabeth's shoulder in Selena's direction. "Are we allowed to . . .?" I whispered, but Selena overheard me and chuckled. "Of course you're 'allowed to,' dear," she said. "I will have to insist on supervising, however," she added with a smile.

"I don't mind at all, ma'am," I said, turning around in place to face Elizabeth. I took her face in my hands and began to kiss her on the lips, softly and quickly, for a long minute before sinking with her into a long, soul-searching French kiss.

We somehow got seated on the bed, but as we continued our torrid make-out session I found myself eased onto my back, and then Elizabeth was on top of me, dry-humping me like mad as we continued to kiss.

At some point I noticed that Selena was now sitting on the vanity bench, legs spread, playing with a large and strikingly realistic penis-shaped dildo. She saw me looking at her, and responded with one of her slow smiles. She held up the jar of lubricant and gave me a suggestive look. My eyes widened at the thought.

Selena stood and walked to the bed. "Elizabeth," she said. "Don't tease the poor thing with all of this dry-humping nonsense. Fuck her properly, for goodness sake."

She helped Elizabeth up, then without ceremony rolled me over on my stomach. She hiked up my gown and slip, yanked down my padded panty-girdle, and slathered a wide swipe of K-Y jelly over and around my asshole. I could feel her long fingers probing me, then she said, "Oh, my—are you a virgin, dear?"

I realized she was talking to me. "No," I said, confused, but she continued impatiently, "No, no, not with a girl . . . I mean, have you ever been fucked?" Understanding dawned, and I shook my head. "That's what I thought," she said. "Well, we'll start small, then. Take off your dress, please. Elizabeth, fetch the vibrator with all the attachments—you know the one I mean? Oh," she said, laughing as Elizabeth predictably blushed, "of course you do."

Elizabeth walked down the hall and returned momentarily with a large flat box. Inside was a vibrator with a set of various interchangeable appendages, from the pencil-thin one that Selena was selecting to a large penis-shaped one that was close to the size of the dildo she had been playing with.

Selena picked the vibrator up, then almost without my realizing it had happened I found the flexible device halfway up my ass. I started to say something, but then she turned it on and I moaned instead.

It felt so good . . . why had I never done this before? I smiled crookedly over my shoulder at Selena as she continued to wiggle the dildo around, in and out of my anus for a delightfully long time. "Elizabeth, bring me the next biggest one in the set," Selena said. She withdrew the device for a moment, then I felt a different, larger shape bumbling against my bum. This time when Selena fucked me it was with slow, short, regular strokes, with lots of extra lubricant. She gently reamed me for perhaps ten minutes or so. It was pleasant; I was sorry when I felt her pull it out.

She put even more lubricant in and around my asshole, and leaned down to whisper in my ear as she did so. "My son's going to fuck you now," she said. "I think you're going to adore this."

First she had me get off the bed. She slipped out of her heels and took off her dress, then laid on the bed on her back. "Come get on top of me," she told me. I hiked up my skip and clambered onto the bed. I straddled Selena and she pulled me to her, kissing me lavishly as our satin-clad bodies writhed against each other. "All right, Gary," she said.

Gary crawled on top of me, and I felt a slick, rubbery dong tickle my inner thigh. "Oh," I remember thinking as Gary/Elizabeth penetrated me. Just that: oh. A sudden understanding that I have always wanted to be fucked in the ass.

I sank on top of Selena and we began to make out again as her son buttfucked me. The poor thing must have been terribly excited, because he hadn't been humping me for long before coming, in quick excited spurts that tickled my bum from the inside and then from the outside as he pulled out.

Gary then began to worry about he mess. First he helped me up and cleaned the semen off me as best he could, then he pranced off to clean himself up and to fetch cleaning supplies.

I was still standing when he left, so turned around and found myself face-to-face with my reflection in the mirrored closet doors. Mm, I thought, I really do love black satin lingerie . . .

Selena was suddenly next to me, looking at the reflection in the mirror. She was still wearing her long black satin slip, and when I looked down at it I found myself getting erect again.

She took me in her arms and fondled me till I was in danger of soiling even more of my outfit. But then she suddenly stopped. She took my face in her hands and gave me a serious look. "I want you to do one more little favor for me," she said. "Will you do it?"

"Yes," I said. "What is it?" She smiled sweetly. "I'd like you to give my son a nice blowjob."

I looked in the mirror again and had a sudden vision of myself on my hands and knees, wearing only black satin lingerie, with Gary's dick— "Oh," I said, as a bit of precome spurted onto my stockings.

She looked down and laughed out loud. "You're just like Gary," she said, amused. "So easily excitable." I blushed. "And so easy to embarrass," she whispered, reaching up and stroking my cheek with one long fingernail. "I like that." I looked down and blushed even more.

Gary flounced back in, naked and clean. Selena smiled indulgently at her prissy son. "Sweetie, we have a nice surprise for you," she said. "Here, sit on the bed." He did so, then Selena went to her dressing table and opened a large, flat jewelry box and I saw that it contained three sets of his-and-her bracelet watches, each one more femme than the last. I felt a little dizzy.

She handed the box to Gary. "If you let her wear one of these,"she said, giving me a small smile, "she'll give you a nice, long, luscious blowjob. Would you like that?" Gary's eyes lit up. "Oh, yes, Mother," he lisped. He gave me a look, and I rather helplessly fell to my knees, gazing at the pretty jewelry.

"Which one would you like to wear?" he asked, absently fondling the contents of the box in his lap. I gulped. "That one," I whispered hoarsely. "Mmm, yes, of course," he said. He picked up the 'hers' version of the watch I had worn earlier. "Hold out your hand," he said. Idid so, but he shook his head. "No, hold it out limp—like a fairy," he teased, lisping provocatively.

I held out my left hand, limp-wristed, and he took it in hisdelicate hand and draped the elegant piece of jewelry in place. He gazed in my eyes as he clasped it shut, then he gently took the back of my head and guided my face to his crotch. I felt Selena's watch slip slightly on my wrist as Gary's engorged cock slipped into my mouth.

The creaminess of my lipstick and the slickness of his precome made me literally smack my lips. I had a sudden appreciation for Selena's use of the word "luscious" to describe the blowjob she had procured for her son. I began to sloppily kiss and suck and lick, then without thinking I plunged down and took it all in my mouth. I could feel the tip of his penis bumping against the back of my throat. Oh my god this is wonderful, I remember thinking. I wanted to prolong it as long as I could, though, so I pulled back. I nipped him a bit, then tickled his hairless balls with my long fingernails, then went back to licking and kissing.

I tormented him for a half hour before I was finally ready to let him have his release. First I stood up and went to the vanity. I gave myself a nice lipsticking, then went back to him, gave him a sloppy kiss, then sank down and hungrily sucked him off until I was rewarded with thick spurts of warm, puddinglike come. I slurped and gulped, frantically wanting every drop. I finally stood up again, straddled him, and pushed him onto his back, where I sank on top of him and kissed him again, forcing him to swallow a mouthful of his own come.

By then I was hard again, so kissed him with more and more passion as I languidly dryhumped him till finally ejaculating all over Selena's slip. And then of course we had to clean up, then re-lipstick each other, which of course led to more kissing . . . it went on and on and (mmm) on. We switched positions in a number of creative ways, with Selena making suggestions and rearranging us at will.

Our long, luscious evening finally ended with Selena dressing her son and I in lovely satin nightgowns and tucking us in bed, where we fell into each other's arms and slept like babies.

***

Selena and Gary are far too close for her to allow him to have an exclusive relationship with any one man, but I have become one of his "regulars." I visit the mother-and-son couple at least once a month for dress-up sessions and lots of sex, and every time I leave I am sore, tired, and absolutelysatisfied. I am so glad that my "quirk" led to my first experience with gay sex. My only regret is that it didn't happen sooner.

Oh well. Nothing like making up for lost time!

 

The End

   

  

  

*********************************************
© 2003 by Gloria Marshall. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.