Part one: Exploring deepest desires with Candy
As far back as I can remember, I was attracted to shiny fabrics. It started with a shiny grey nylon bathing suit, which got me very excited every time I wore it. In high school, during a talent demonstration, I nearly had an orgasm watching a girl in my class perform her baton twirling routine in front of the whole school. I was in a fog of lust during the whole performance without actually knowing what I was responding to. It wasn’t the skill or the girl… it was her outfit. White satin top with a frilly skirt and shiny silver panties which were meant to be seen. If I could have had a chance to simply touch her I’m sure I would have cum in an instant. I never forgot her. Her name was Tracy.
My obsession with slippery, shiny, and slinky clothing was giving me instant erections. I was distracted by things on clotheslines waving in the breeze, catalogues with women modeling the latest seductive underwear, and a compulsion for taking things that didn’t belong to me. I stored much of what I pilfered in a box in our garage for a while where I could spend lazy summer afternoons feeling them in my hands while admiring their colour and texture.
Once I rented my own apartment I was free to explore, purchase, wear, and lounge around in a growing collection of slips, nightgowns, panties, stockings, and even the occasional bra. Periodically I managed to snag something interesting from the apartment laundry to add to my already wide variety of purchased teddies, panties, and half-slips. I even managed to shoplift a few basic items from some of the larger department stores, but their selection was not very enticing.
I shelled out for a dancers’ catsuit made of very sleek nylon which hugged my body from neck to ankles. I had to trim the crotch of the catsuit to allow my cock and balls to stick through. The catsuit made all the slips and gowns slide around my body in the most wonderful way. Thigh-high stockings were tricky to purchase until I learned my best size and fit. I found a garter belt which I learned to use to keep up the stockings. But, I never tried to pass as a woman, ever.
When I discovered charity shops and second hand outlets I thought I was in heaven. Not only was everything much cheaper, but there were lacy and slippery outfits I would have never been able to find anywhere else. The wide diversity of truly sexy underwear cast off from broken marriages or failed seductions expanded my collection in many new directions. Shopping in these outlets became a new source of excitement. I sometimes dared myself to venture out with some sort of slinky underwear under my jeans and sweater. It was thrilling for a while. But the thrill would wear off quickly so it didn’t provide me with the kind of shivering excitement I could get from just being at home wearing my newest acquisitions.
In order to keep any building management or repair people from discovering my collection I kept it locked in a suitcase. Over a year’s time that suitcase was stuffed to the limit. I also began a collection of magazines and catalogues featuring lingerie. Playboy was particularly enjoyable because they issued a special magazine exclusively featuring their models in sumptuous and stunning lingerie.
My early career was developing very well while my personal life was expanding with friends and colleagues; but none of them could have suspected I had a literal closet full of women’s intimate garments which allowed me to explore my sensual side without feeling ashamed. I was completely satisfied with being totally aroused by my outfits and stroking myself while enjoying the wispy nylon and silks flowing gently against my skin.
What was even more wonderful was to spend an entire weekend smoking dope and lounging around in various gowns and silk robes. I spent many stoned nights stroking my cock through wispy nylon and satin panties. Of course I toyed with buying online when it became popular but I did not want anyone tracing my purchase history, or to get ads for ladies’ intimates at work.
I did consider sharing my secret fetishism with some of my girlfriends over the years but whenever I got anywhere near having a conversation about men who crossdress their faces betrayed disgust and outright horror. Some believed it was a perversion. Needless to say my relationships with these women did not last very long. For the few who let me fuck them I was usually so distracted by their panties on the floor or their bra on the chair that my efforts to please them did not afford me the same kind of heady sexual arousal I could provide for myself. Sex with women — whose sexiest undergarment was shiny tap pants — could still get me hard enough to fuck them, but my heart was never in it. Their orgasms did not thrill me as much as they did them. If any of them knew about the suitcase in my closet they might have freaked out. If women like this knew who was sitting right next to them in the movie or at a restaurant they might have exploded with fright. But whenever I found myself fucking some eager young woman I was mentally dressing myself in some beautiful peach slip with yellow panties while thrusting my hard cock through her furry pussy lips. Eventually I realized I might never find a woman who could understand what I was so passionate about, so I just had to accept it might never happen.
Then I met Candy. I was introduced by a colleague when we were casting a part for a music video. She was lovely and sweet. We had her performing as a skater girl at a roller rink shortly after the “death of disco”. It might have been the outfit she wore, or the way she fell into the role of seductive vixen, but I was immediately taken by her skill and her beauty. The satin outfit triggered some of the same feelings I’d had when watching a girl twirl her baton long ago. To say I had a hard-on for her would be an understatement. All during shooting I was stiff. Her smiles while waiting for the next shot tickled me inside. Her lovely voice and wide eyes sent chills through me.
After shooting finished I pursued a friendship with Candy so we could keep in touch. Outside of work we had some nice lunches where I got to know her better. She had a loser boyfriend when we first met. She was very up front about their sex life, not the least bit embarrassed to describe their nights together. She complained that he was only interested in his own satisfaction. Her blow jobs, hand jobs, and the endless number of fucking positions the guy insisted on did nothing to get her aroused. She had been brought up believing it was her role to make him happy.
She told me she really appreciated the way I listened without judgement. Then she confessed her name wasn’t really Candy, it was Amanda. Her friends called her Mandy when she was younger so it was easy to come up with Candy and respond to it naturally. She used the name to keep her acting profession separate from her personal life. Guys were always hitting on her, which made her boyfriend furious. Whenever she felt it was important to keep her working life separate from her “real” life she adopted the Candy name. As soon as she told me her real name I knew she had allowed me to cross over into her personal life. She was moving me from the untrustworthy category to the trusted category so I let her know how honoured I was to be trusted with her little secret.
It took a long time for me to help her recognize she did not have to put up with her boyfriend’s unreasonable demands or his jealous need to control her every move. Two months later she finally realized she was not his possession. I encouraged her to ignore his invitation to move with him to another city. It was purely in my own self-interest for me to talk her into staying. She broke up with the guy, and we began seriously dating. It wasn’t a wild romance or a rebound thing. I was thrilled to be with her under any circumstances.
Amanda was very stylish and keenly aware of her appearance so she invested a lot into hair, makeup, clothes, and shoes. She’d confessed before about how her nasty boyfriend insisted she dress like a tramp to get him excited. A quick exploration of her underwear drawer confirmed the story. I was delighted to find a seriously sexy wardrobe of skimpy and lacy things there. My beating heart was difficult to conceal once I knew the kinds of things she liked to wear. I was very tempted to take a souvenir for my own collection because I wasn’t yet sure where things were leading, but I held back thinking there might be another time to explore more thoroughly.
I was happy to be able to talk about Amanda’s intimacy problems which, I hoped, might open up opportunities for her to consider me somewhere down the line. The more time we spent with each other the more of a hold she had over me. For the first time in my life I felt like this might be someone who saw me differently. She appreciated my concerns, advice, encouragement, humour, and patience with her.
After our first kiss we quickly moved from being just friends to something more intimate. It wasn’t long after when she invited me to take her to bed. The first time she slipped out of her dress in her bedroom I was smitten. I was unable to think about anything else. The stockings were fabulous, the matching bra and panties were touched with just a hint of lace while accentuating her perfect body. Amanda may not have had great taste in men but she had great taste in underwear. She let me run my hands all over her that first time. I nearly lost control just touching her. Here was this wonderful woman — wearing the most beautiful underwear a man like me could have wished for — asking me to let her feel my hard cock. The tone implied more than just a simple request. It had overtones of her desperate need to touch my erection while I was stroking my fingers against her panties.
I could have just stayed this way for the whole night, I was so wordlessly happy, Her hand on my erection felt wonderful while my fingertips against the smooth curve of her pussy was giving her just the right kind of stimulation. Needless to say Amanda had to ask me to stop my explorations so we could get on with fucking. I laid her back, slid down those glistening panties, and stopped to admire the carefully trimmed fur of her pussy. I channeled all my sexual arousal into delivering her very first oral orgasm. With my hands on her stockinged legs I wormed my way into her soul using every part of my tongue.
Wearing the entire outfit, except the panties, she cried out with a shout of primal release. The power of her orgasm seemed to catch her off guard but I was basking in the glow of being able to give her what no other man had. I was beaming with pride when I lifted my head from her slippery cunt.
Once Amanda stopped panting she demanded I fuck her immediately. Although the tone might have been interpreted as sexual desperation I distinctly heard overtones of her need to direct my actions. I got totally naked and climbed on top. She was hot and glistening in the most beautiful way. Our kissing turned to stroking which led to guiding my stiff length into her with her hand. At that moment I think I finally understood what consummate really meant. I felt like we had passed from the vestibule of anticipation into the main house of sexual pleasure. Vast stairways of possibility opened up. It was a beginning unlike any other in my life.
As I slid deeper her hand fell away. I became totally devoted to giving this wonderful woman whatever she wanted. Everything she truly deserved. I had not been able to give anyone else my total attention before. The feeling of my cock inside her caused all other thoughts to leave my mind. I spent the next twenty minutes fucking her as gently as I possibly could. I was determined to feel my cock touch her in places no other cock had been. I stayed keenly aware of every flinch or squirm my cock produced. I waited her out until I sensed a change in her breathing. Amanda was climbing the mountain toward her next orgasm, her first with my cock inside, while I slowly increased the speed of my thrusting. Eventually she exploded with a whine of pure delight as the walls of her cunt closed tighter around my rippling shaft. It felt like a full-body thank you. I kept my slow fucking on track as she tried to calm herself. But it was no use. This constant humping uncovered another orgasm waiting to be released. My very excited cock enjoyed the warm smooth channel of her delight while Amanda came two more times.
When we finally laid back to rest, Amanda expressed some shock at experiencing multiple orgasms in rapid succession. It was another first for both of us. During our cuddling I complimented her sexy underwear. Even with her stockings a rumpled sleeve at her ankles, her bra abandoned nearby when I decided to lick and fondle her tits, her panties nowhere to be found, I had found my dream girl and fought the compulsion to tell her how I liked to get off on my own. Until I fucked Amanda that first time I’d never experienced a multi-orgasmic woman. I didn’t know they existed. But Amanda didn’t know she was capable of coming more than once, or twice, or even three times. No one she’d ever slept with before had provided her with such totally consuming orgasms.
After another month of increasingly regular invitations to her bed I worked up the courage to bring up the subject of my fascination with her wonderful collection of underwear. I’d given her so many compliments about what she wore it must have made her wonder about me. Some of our conversations included which pieces were her favourite, which item had been a gift, or which ones went well with others. I felt like a prince whenever I slid my fingers over her smooth ass covered in purple nylon. I loved feeling her breasts inside her bra or touching her legs as they held my waist. I don’t think I could have ever believed how much stimulation her underwear would provide me. I loved to touch her all over but soon I felt a desperate need for Amanda to touch me in much the same way.
As much as it thrilled me to feel my cock sliding through three layers of silky smooth nylon, while my legs were firmly encased in shimmering stockings, I began to sense there might be even more excitement if I just took a chance with Amanda. My rational brain added up the costs and benefits of her freaking out. I was truly in love with her as much as I was reserving my strongest desires for her. I spent a week deeply torn between expressing my true nature or losing her altogether. If I didn’t share this with her I knew our relationship would be over anyway because it was not something I could remove from the dynamic of my feelings for her. The strength of my arousal was directly related to the way she looked when wearing sexy underthings. I was convinced she would eventually sense I was not being entirely honest, which would erode the feelings we had for each other. As easy as it was to keep this kind of thing a secret from people outside my world I would be even more stressed out to keep it a secret if this relationship was to go further. But I felt it was becoming a mental wall I desperately needed to knock down if I was going to continue to be honest with her.
I can’t quite describe the sense of fear which filled me when I contemplated talking to Amanda about my own collection of fine things. She hadn’t been into my bedroom yet to perhaps discover my secret by accident. The day I started the discussion was a lovely sunny day after we’d been going around having a wonderful time. By evening I was serving dinner at my house and a kind of tingling rush went through my entire body. It was unlike any other sensation I’d felt before. The calm which followed gave me permission to take the plunge.
We took our coffee onto the back deck where we chatted quietly about how she was having special feelings for me. It was the perfect setting for us to talk about where this relationship was going. When things turned to the subject of a long-term or permanent relationship I saw my opportunity to clear the air so as not to lead her on any further. I can’t even remember how I started out. I don’t recall anything I said, or how I managed to explain myself, and I can’t even recall much more than how scary it felt to be putting this out there.
Everything I told Amanda, before she gave me her response, was wiped from my memory the moment I heard her begin questioning me about how it made me feel or what I liked best about dressing like a woman. Amanda seemed completely comfortable talking with a guy who had just declared he liked cross-dressing in sexy lingerie and underwear. I felt like I had the wind knocked out of me. This was definitely not the reaction I expected. I had convinced myself this would be the end of our passionate affair. I hadn’t prepared myself for Amanda’s unblinking acceptance. At one point her arms were around my neck as she continued to pepper me with questions. My brain cleared enough to realize the joy which was emerging from deep within my soul. I was truly liberated from the shame of being a social outcast. I caught myself wondering if this is what gay men felt when they came out to a friend or a family member who accepted them.
Well, the following month or two was truly a rebirth for me. We spent even more time together while she learned more and more about me. She seemed fascinated at first, but genuinely impressed with how well I handled my sexual fetish. Amanda would look things up then arrive with more questions for me. But more than anything else, during that first month, Amanda admired my taste. She became very adept at helping me dress, and showing me things only a woman can do to enhance my enjoyment.
What also emerged, from our new level of intimacy, was a side of Amanda no one had ever seen. She confessed one afternoon how she harbored new feelings for domination over a man which had lain dormant, or suppressed, until I helped her find her true feminine self. She had been trying to find a way to bring her new self into our relationship without scaring me away. Once I realized she truly embraced my feminine self I told her it would please me no end if she would explore her own sexual fantasies right along with me.
Not only did she encourage my fetishism but she found herself wanting to order me around, give me rules, make me her slave, or take control of my orgasms. What had only, during our first fuck, been the slightest tone of demand in her voice slowly became a full-throated commanding voice after we opened up to each other. The confidence which accompanied her discovery impressed me.
Together we seemed to have unshackled from the people we were “supposed to be” only to discover two entirely compatible people under the surface. I had trusted Amanda with my deepest desires by demonstrating my willingness to risk everything when I revealed them. She felt she could trust me to let her explore this new side of herself the moment I drew my tongue along her slit that first night together.
Our lives changed nearly overnight. Within only a few weeks her increased confidence allowed her to advance in her career. By the end of six months Amanda was earning much more than me. Her responsibilities allowed us a lifestyle I never expected to enjoy. Our shared liberation allowed us to take risks which rewarded both of us rather suddenly. After only a year together we had become a force of nature. Her yang and my yin were in perfect balance to produce a sexually charged private life unlike anything we ever could have achieved on our own.
After our first year together I became totally devoted to Amanda’s pleasure as she did to my own. The only time we ever had any kind of argument or fight was when I called her Mandy. She got pretty worked up about it, telling me she did not want to be reminded of her teenage life ever again. So, the only taboo I was ever told NOT to cross was to call her Mandy. I never did after that.
Thanks to Lara Sterling for the inspiration and information: