A Story Of A Sissy

When I was 22 I worked at a Target store in Orange County. A girl worked there, she was just out of high school, but she looked like an innocent and sweet girl, I mistook her for 16 or 17, she was actually 19. One day I was organizing the shoe department and was admiring a pair of patent leather red pumps lost in dreamland, believing I was alone. I must have been lost in this state for minutes because I was shook from my daze when she tapped me on the shoulder asking if I was ok.

At closing that night, we punched our cards and walked out together. Not so unusual, we'd become friendly. I was with my girlfriend Jacqueline at the time, but I'd be lying if I said I wasn't totally attracted to her.

"Come check something out real fast," she said as I was about to get into my car.

I walked over to her car and she used her fob to unlock the trunk. She opened it and pulled out a pair of leather, knee-high heels, red, with a gold zipper up the side.

"Do you like them?"

I could only smile from ear to ear. I was aroused immediately. She was so young and innocent seeming and with this little maneuver garnered my love immediately.

Nothing ever happened between us, but because of her I began having fantasies of cuckoldry and submissive devotion.

Shortly after Jacqueline and I had already broken up, made up, and broken up a couple of times already and when she finally made it clear she was done with me. I began stealing pantie and I simply turned my sexual desires inward.

I imagined I was Katherine's submissive. Katherine is the girl from Target with the boots. I didn't know what a submissive was at the time, but I imagined myself in service to her. I imagined I dressed her, bathed her, gave her mani pedis, and cooked and cleaned for her. She was off limits, too young I told myself. But I could fantasize about serving her.

Jacqueline got me started. I will never forget. We used to play this game, no using your hands, everything else was fair game. We'd play it for hours. That is not an exaggeration. We knew how to play. She knew how to play. She brought out the best in me.

One night during this game, she put on a pair of sheer-to-waist pantyhose. After putting them on in front of me she asked if I'd like to wear a pair.

"They'll make us both feel really good," she added.

I'll never forget this moment. I had to pretend not to know how to put them on, I'd done it so many times over the years, ever since discovering my mom's panty and hosiery drawers. She must have known because after fumbling to follow her instructions on the first leg, I gathered the silky hose into a ring, slipped it tightly over my pointed toes and slid them snuggly and effortlessly up my second leg. An impossible task for a first timer to have completed.

After we'd both slipped on and adjusted our hose we went to the bathroom and admired ourselves in the mirror. She got an idea, at least she was a good enough actor to make it seem like a spontaneous act, to paint my lips with lipstick.

"Just let me try, you try, see what it looks like," she prompted.

Of course it was a dream come true and my feigned resistance must have made her laugh inside. She painted my mouth and pointed my face to the mirror before she kissed my mouth the way I'd imagined lesbians kiss.

We played that night for literal hours. Grinding, scissoring, kissing, applying and reapplying lipstick, we were behaving like the lesbian porn actors in the films we both loved watching.

After that I began wearing her panties. I bought my own panties, nightgowns and chemises. I bought her stockings, panties, hosiery, garterbelts and heels and we made love like homosexual women not heterosexual couples.

She used buttplugs on me. I wore a buttplug to work at her request. Toward the end of our relationship, she was calling me her sissy, her pantyboy, her faggot sissy and I served her evermore fervently. I think it wasn't what she really wanted. She wanted a real lesbian not a man pretending to be one. And she liked men, and she wanted a man to fuck her, not a man to serve her. We were great together, and if I'd known then what I know now, I'd have proposed to her with a caveat that would make my proposal irrefutable.

I would have asked her to be my mistress dom wife. "You can go and be with a woman, be with a man, be with 5 men, I don't care, just always come back to me and let me live vicariously through you and be completely devoted to you." Is what I would have said if I knew then what I know now.

Jacqueline and I are both in our 50s now. She's happily married, and a swinger at that. Apparently she and her husband swing. I don't know the details, but over the years we've kept connected in some form or fashion. When we were in our mid 30s we met up in Vegas for 5 days. She's sent me photos of herself, I've written stories and sent her way more illicit photos of myself to her than she's ever shared with me. Hers are tasteful, mine are lascivious. Typical male-ego-driven stuff.

I've had one good relationship since her, plus a marriage come and gone. The marriage only lasted 5 years and it was a terrible relationship. In between the one good relationship and the marriage I had an online, digital affair with a woman overseas, her name was Joan. I'd moved to Europe and she was an old colleague. One day she sent me an email asking if I'd read a story she'd written. It was erotica. Ok stuff, pretty tame by my standards, but that little email led to me fulfilling my ultimate fantasy.

Let me start with the one good relationship I had after Jacqueline dumped me. Maria. She was a pansexual, Ivy League, totally leftwing radical who let me fly my freak flag. She was young, 23, and fresh out of undergrad. She found my lingerie. When I met her it was so totally unexpected and almost a year since I'd broken up with Jacqueline so I had built up quite a collection. Jacqueline leaving me left a huge emptiness that I filled pretending to be a woman. I would dress up and basically have sex with myself. I had dildos, vibes, plugs, lubes, lingerie and a huge mirror that Jaqcueline had insisted I buy that I spent whole nights in front of masturbating. The first date with Maria, I had absolutely no intention of taking her back to my place and yet, that's how it went.

We fucked and then we spent the weekend together. I was on alert. I knew I'd have to hide my stash and in my sloth had let that stash permeate my whole apartment. I had panties in my regular chest of drawers with my male boxers. I had my hose in my sock drawer. I had vibrators in the bedside tables, not just one or two, but three, plus two buttplugs. I wasn't worried if she found those, I could explain it simply enough and not seem like a total freak. I had LegShow magazine, two years worth of them in the bathroom under the vanity. I thought if anything, having them in the bathroom would seem ok, and that I didn't attempt to hide them I thought would come off as macho. But they were LegShow. If you know or knew what LegShow magazine's focus was then you might think twice, it was a submissive men's magazine. I'd actually had several letters published by them. But I also had heels under my bed, gowns in between the boxspring and mattress, and chemise hanging in the back of my walk-in closet.

Like I said, I was on high alert, but she never snooped around, just hung out and fucked, drank, fucked some more and then it was Monday and I went to work early, told her to lock the door on the way out, and I'd call her to see if we could hang out later.

I got home Monday after work and she was laying on the bed watching a sissy DVD on the tv, laying on my bed on a pile of panties, hose, and lingerie.

So, after Jacqueline, I never thought I'd have that kind of sex again, and along came Maria. We had fun. But she was volatile. I realized after we broke up, she wasn't as "liberally-minded" as she presented herself to be. She was ok with women being pansexual, but deep down, it bothered her that I liked cock and cum as much as I liked pussy and cream.

We had fun. I loved her, as much as I thought I'd never love anyone like Jacqueline, I did love Maria as much. Of course it was different. Everyone knows that. But I asked her to marry me, but it was too late. She was moving on, going to law school and I was left in her wake. Surprising to me was that she kept in contact. Since we broke up, we've gotten together for sex twice, separated by ten years, the next one should be coming up soon, lol.

Maria fucked me with a strap-on. I sucked her strap-on. It was while we were together I found shemales. I would go to this porn shop that had closets with two-way windows. You could watch porn and open your window so the person in the next closet could watch. They could open theirs or you could both have them open. I would dress up, put my male clothes on and go to the porn shop. I'd strip down to my lingerie, put on shemale porn, and open my window.

I loved it. I tried telling Maria about it and she was furious. I was humiliated, but not the way a new-born sissy can handle. If I'd known then what I know now I would have played it a lot better. Would have accepted it and let her have her way with me.

That was the beginning of the end. After she found that out, she never recovered. She went off to law school and within the year we'd broken up.

After that I bore headlong into being a sissy. I moved to Florida for work, and had a condo at a snowbird complex which meant I had remarkable privacy. The complex pool was always vacant. I had the place to myself. I began going on long weekends up to Tampa where I'd get a room and shop all weekend. Panties, hose, shoes, everything. Those were the early days of the internet and I would go into yahoo adult rooms and show myself off. I began dating myself. I began shaving. Not my legs, but I kept my ass, balls, and cock, clean-shaven. Basically, as long as I wore a long pair of shorts, no one could tell I was a sissy. But if I went swimming, everyone would have known.

On weekends at home I spent cleaning my condo, sipping cocktails, taking an oxy or perc, smoking some weed and playing dress up. By night time I was going online and showing whoever wanted to watch. I made it so the camera never showed my face, it was totally safe and fun as hell.

I started on Craigslist. I made a profile, back then it was so easy. At first it was just for fun. I never intended to follow through. Then on my first summer in the condo, the whole complex was empty because all the snowbirds were up north, and I took a risk. I answered one of the ads.

I invited him over.

I wrote, "I'll be at the pool. I live in a snowbird condo complex and it's totally safe and private. If you show up, we can go to my condo after we smoke."

I'll never forget it. I was totally jacked. High on percs, weed and Jack, I paced, and waffled, he'd never know who's condo it was, the place was huge, I just won't go to the pool. No, no, I'll go, what the hell, just go, you're fuckered up enough. No, man, you do this and you cross a line.

Back and forth I went. I popped another pill and poured myself a triple jack and coke, rolled a joint and steeled myself. I had a pair of powder-blue Vanity Fair, full-cut panties on. I wrapped my beach towel around myself and strode confidently down to the pool, through the gate and pool house, dropped my towel and slid into the warm summer pool night.

I was 40 minutes early. I soaked and felt the night air and water. I looked at myself in my wet panties. Before I knew what was happening I heard the metal hinges on the pool gate squeak and a black man walk through the pool house.

I was stunned. I had no indication. I just let it all go and smiled. I was actually coy when he told me he liked my panties. We smoked and then, shyly I got out of the pool and wrapped myself up and we walked back to my condo.

As soon as I closed the door, I turned around, got on my knees and took out his cock for him. It was huge. Bigger than any dildo or vibe I'd ever owned. I hesitated not. I took his cock into my mouth and let instinct and years of fantasizing do the rest.

I remember my eyes watering, as if the sheer size and length of his cock was squeezing it from my eyes. I remember how proud I was to be able to take all of his gorgeous cock down my throat as if I were a seasoned pro.

He came down my throat. I remember recognizing the point of no return and the moment in time wherein I contemplated what to do, get off his cock or let him cum in my mouth. I doubled down, forced his cock down my throat and rode his bucking cock as it jerked orgasm down into my stomach. I didn't even taste it, I'm glad I chose this route, because it was like it didn't even happen. I let him slip out my mouth, chugged the rest of my jack and coke and it was like i didn't even do it, like I hadn't just made a man cum.

But I did. And I wanted more.

I did find more. Over the next few years I sucked 7 cocks. I also had 3 girlfriends, one from Japan, one old lady 20 years my senior, and one Albanian. None of them meant anything other than fulfilling some wild kink or fantasy. I didn't have any interest in love, only making my fantasies a reality.

That's when I moved to Europe and started that digital affair. Joan was a fellow teacher and friend. We were just friends. She was married, I was having gay and hetro sex with whoever would do it. No one knew what I was doing at my work. I never told a soul. I was totally anonymous. The gay sex I was having was with out of towners, the girlfriends I had were locals and it made it look like I was some kind of player. Joan had no idea. And I had no idea she liked me. We were good friends, hung out a lot, even collaborated on school stuff, but I never imagined.

In Europe I drove deeper into my fantasies. I bought the finest lingerie from the finest department stores. I would take the metro across town as to minimalize risk. I made a whole day of it. Wake up early, bathe, shave, smoke a joint with some coffee, dress up like a sissy and put my male clothes over top, then head out.

Karstadt was my favorite store. I absolutely adore the smells and colors of a department store ladies section. I would browse for as long as I could so as to not seem awkward, and I'd ask the sales women for help on sizing to make it seem like I was shopping for someone else. I always wondered if the women suspected me of crossdressing. But it was a thrill to imagine they knew. I was in a constant state of arousal whenever I went shopping for my sissy paraphernalia.

I became a lingerie expert. I bought only the best. I would make my purchase in the lingerie department, migrate to the makeup and perfume section, buy a tube of lipstick and some cologne, then migrate to the dress section and browse looking for the perfect outfit. If I didn't like anything, I had no shame, I would simply leave without a purchase and go to another store. I would look at the shoes. I love the women's shoe department. The smell of leather and nylon is intoxicating. I never bought shoes, I had to do that online. It would have been too obvious I was shopping for myself. In hindsight, and knowing what I know now, I would have no problem shopping for shoes now.

I would go to the drug store and buy shaving cream, razors, and depilatory cream, all in the women's section. I'd pick up candles by the dozen, all feminine scents. I bought bath oils and body lotion. I made my purchases without shame or embarrassment. I loved watching the reactions of the clerks sliding my purchases across the scanner, glancing up at me, and back down at my purchases.

Then I'd treat myself to a lunch at some fancy cafe or bistro and sit out in the sun on the sidewalk with my women's department store shopping bags piled up on the chair next to me, like a date. I used to laugh to myself about it. It was during this period I realized what I was actually doing was having a date with myself, my alter-ego. I called it my metaphor.

During lunch I'd go through my purchases, fingering the fabric, reading the instructions on the makeup and lotion bottles. I didn't care who saw me.

Usually by afternoon I'd be back home and I would begin my ritual. Lace the room with candles, open a bottle of bourbon, smoke a joint and by the time the sun was setting and Coltrane was playing on the speaker I would begin. Depilatory cream; everything below my neck. I was coated in fiery hot white cream and just like that my male was washed down the bathtub drain. I'd prance around sipping my ginger ale and bourbon smooth as a woman. In various reflective surfaces around my flat I'd catch glimpses that reflected back the image of a woman, not a silly man. My flat, only brightened by flickering candlelight, I'd go in the living room and prepare. I'd convert my work desk to a vanity equipped with vanity two sided mirror, makeup, makeup remover, brushes and sponges, and nail polish.

I would slip on a favorite pair of panties. I always wore Vanity Fair full-bottom briefs for this part. A nice comfortable swishy pale blue, or pink pair for the full effect. I'd paint my nails, fingers and toes, a labor of love as I sipped my drink and toked my joint. Then I'd try my hand at makeup for a while. I was terrible and never got the hang of it. I am always stunned by how much practice it takes. Every woman you see has literally spent hours and hours practicing their makeup.

Once I knew the nails were dry, I'd slip on my hose. Either thigh-highs, or sheer-to-waist, however I was feeling. Thigh highs if I wanted a girdle or garterbelt and exposed pussy and ass, or sheer to waist to give me that all-over-womanly feeling. Whatever the case, I only wore Wolford's.

Then, depending on whether or not I wore a garter or girdle, I picked out a chemise. I had a dozen elegant chemises to choose from. I'd go to my closet and fondle the silky material, placing it in front of myself and twisting and turning in front of the full-length mirror. Then my wig and finally my shoes. I had a pair of black knee-high leather heels with a zipper up the inner calf.

I'd do this just about every weekend. Sometimes I'd do all this, except the makeup, wig and heels, and I'd put on a suit and go to the theatre or symphony. Make it a real date.

Invariably, at the end of the night, I'd be lying on my bed with my vibrator and my cam open to whomever wanted to watch. I kept my face out of it so it was totally safe. I had a fake digital person online that was impossible for anyone other than a hacker to connect back to me. I would tease the boys so viciously. They would berate and humiliate me, calling me every slanderous name you could imagine, and I just teased and teased. Only ever ejaculating after an entire evening of teasing so that only the truly devoted viewers would get the reward.

That's what I had become when Joan wrote me that email and shared with me her erotic story.

Joan had no idea, at least that's what I thought at the time.

Let me go back to Jacqueline. She got me started in all this. Technically, I got myself started when I was just a teenager and found my mom's lingerie and stockings. So, ever since I was 13 years old I have loved silky panties and hosiery. I kept it in a securely locked safe that no one would ever discover. I thought it would remain that way until I met Jacqueline.

She told me something that I'll never forget and also have come to believe through the years to be absolutely true. Everyone wonders what it would be like to be the opposite of their sex. The one caveat I'd add would be that "everyone" meaning anyone self-aware and open-minded enough about their sexuality has wondered about being a member of their opposite sex. I've been with women, my ex-wife for one, who have no clue about their own sexuality. They are happy being a woman and never curious about the opposite, this kind of lover has absolutely no idea how to please a member of the opposite sex. I realize that if you are curious about what it's like to be your sexual opposite, then you are a good lover, at least open to the potential of being one.