Next Step to Nirvana

As I sat on the bench at the mall, I tried to calm myself. I thought I had prepared myself and planned everything. But my breathing was fast, my hands were sweaty and my nerves were wired. I was home for holiday break from college and had decided to take the next step in cross-dressing.

Up until now, most of my dressing had been secretly taking my older sister's underwear. It started when I could no longer resist my curiosity. Finally, one afternoon when I was home alone, I snatched the first pair of her panties that I could find, ran to my room, and quickly pulled them on. It was electric.

As a teenager, my hormones were already racing. This sent them off the chart. My legs felt weak and I could barely stand. I couldn't keep my hands off the panties or myself. They were tight. They were soft. They were smooth. They were pretty. The smell was subtle, but overwhelming. My mind was muddled, but also hyper-sensitive. I was certain every little noise in the house was someone coming home who would discover me. Although I wanted this feeling to last forever, I managed to take them off and return them to my sister's room.

I collapsed on my bed and tried to sort through the rush of feelings and emotions. I was simultaneously scared, guilty, horny, exhilarated, and ashamed for being exhilarated. Mostly, I was confused. It had only lasted a few minutes and my frazzled mind didn't remember all the details, but I knew two things for certain. First, I would never forget my first panties. They were burned in my memory: deep green tricot fabric with delicate, lacy white trim. And secondly, I knew it wouldn't be my last time wearing woman's lingerie.

My dressing evolved from that life-changing first time. I became adept at sneaking my sister's underwear so I wouldn't be detected. Rachel was naturally messy, so it made things easier. I thought I knew her panties better than she did. How she folded and stored the clean ones and where to find her used ones. Which ones were perfumed, and might arouse suspicion. Which were her favorites, and would be missed. Which ones weren't, and could become my regulars. Most importantly, which ones were special and had to be avoided, because someone else wearing them could be easily detected.

I proceeded slowly. Fear of discovery and humiliation was a powerful restraining factor. But complete resistance was out of the question. I never felt as alive as when I slipped the panties up my thighs, snapped them in place and smoothed them over my bottom. Cocaine couldn't have had a stronger grip on me.

Sometimes, there were weeks between panty sessions. Other days, I was obsessed. It was all I could think about and the urges were impossible to resist. In school, I couldn't focus. My mind kept imaging the panties the girls in class were wearing and how they would feel on me. On those days, I rushed home to indulge and release the pent up energy. While I tried to be cautious, sometimes I had to take chances to get a quick fix. Occasionally, I would dress while Rachel or my parents were in the house and sometimes when they were in the room next door. If possible, the risk increased the pleasure.

With time, I expanded beyond panties to discover the pleasures of other female attire. First, other lingerie. Then, the entire feminine wardrobe. But always in private. Rachel was not clothes-obsessed, but to me her bedroom was a treasure chest of discovery and desire. I went through phases. For a time, I was obsessed with baby doll nightgowns. Their touch, their frills, their peek-a-boo shortness, drove me crazy. Once, when I was wearing a particularly feminine pink and black baby doll, I was overcome with the compulsion to go public. I wanted to go to the living room, or the park, or the school cafeteria and twirl around so everyone could see how pretty I looked and how glowing I felt. How could clothes have such a hold on me?

While I had friends and sports and hobbies and interests, cross-dressing became my secret passion. Rachel's bedroom was always my primary female closet. However, I dabbled elsewhere. Visits to my female cousins were no longer boring, but adventures. Summer jobs provided new opportunities. The mirror became my best friend. I experimented with make-up, but clothing was my love. On several times, it was almost my downfall. I became so enthralled in my fantasies that once I failed to notice Rachel arrive home. She was seconds from seeing me in her favorite above-the-knee, yellow sun dress, complete with bra, camisole, slip, panties and sandals. When she came into the room, I had barely pulled up my shorts (over the floral, high cut briefs). Rachel commented on how pale I looked. I mumbled about coming down with something. She mentioned it to my mother and I got the next day off from school. I used it for an all day dress-up.

When I went away to college things changed. The new setting, high academic demands and the lack of privacy forced me to cut back. On my two weekends home, I binged. It was less than fully unsatisfying. Rachel was also away at school and most of her best clothes were with her. My mother's clothes would do in a pinch, but they were the wrong size and unstylish. My needs and standards were increasing.

That's what brought me to the mall. I had resolved it was time to move from panty thief to panty purchaser. I wanted something that was truly my own. Panties that were sexy to me because I had selected them, not because they were available.

However, sitting here in the mall, it was apparent that it was easier to resolve, than to act. As strong as my desires were, I didn't want my obsession discovered. But, I was determined. Over the last couple of days, I had thought about little else. I had chosen an average department store in a mall away from my home, to minimize the likelihood of meeting anyone I knew. It was also a weeknight and shortly before closing in the hope there would be few customers. The holidays helped with my "cover story". If anyone asked, I'd say the purchase was to be a special present for my girlfriend. I figured that if I looked nervous, that would be normal for many men purchasing lingerie as a gift. Finally, I had worked out back-up plans. At worst, I could simply walk out. Or, I could just buy anything, and be in and out in minutes. At least, it would pop my cherry and I would no longer be a panty-buying virgin. As I sat on the bench and went over these plans, I became calmer and more confident. I took a deep breath, said "Now or never" to myself, and headed into the store.

I stopped just outside the woman's department to check things out. As I hoped, it was relatively uncrowded. A few customers strolled around absorbed in their own shopping. The clerks were busy at the registers. The time seemed ripe. I entered at a slow walk. I didn't want to seem too eager or draw attention. A slow pace gave me a chance to furtively look around and get my bearings. I was in dangerous and foreign territory. The lingerie department was in the back. I hesitated. So far, I was just walking through the store. Crossing that threshold seemed to be something more. An inner sanctum. Forbidden. Taboo. But as much as the cautious, rational part of me was hesitant, a stronger, emotional part was drawn in. My thoughts had shifted from determination, to a strong and willing attraction. I entered.

Once inside, my perspective seemed to shift. My reluctance and fear were momentarily replaced with awe and excitement. I couldn't believe how huge the lingerie department seemed. The men's department had a few shelves for underwear. But, this seemed to go on for endless aisles and corners and cubbies. It must have covered half of the floor. As I took it in, I became dazzled. My eyes were awash with sensation. Everything was silks and frills, bows and lace. A rainbow of colors. The whole department seemed soft and pretty and girlish, and somehow inviting. My well-planned calm was in pieces. My skin was tingling, my hormones raced, my penis aroused.

I wasn't prepared for the choices. Where to start? I checked my watch. Less than 30 minutes until closing. I had to get to it. A quick look around revealed just a couple of women off at a safe distance and a single clerk at the register. Perfect isolation. I moved further into wonderland. I fought to keep a silly kid-in-a-candy-store grin off my face. The panties were spread throughout the department depending on material and brand. It dawned on me that I had no idea specifically what I wanted. The infinity of choices wasn't helping. If I was rich, I would have bought one of everything. But I had a very limited budget, so I forced myself to focus. I moved toward a display of panties against the wall, more because they were away from people than a decision they were what I wanted.

I quickly became engrossed. I touched some panties hanging on the racks and the air seemed to buzz. I hadn't thought I wanted plain white. But some of these were too gorgeous for words. Ruffles and trim. My mind imagined them slowly moving up my legs and I almost had an orgasm. I no sooner saw and touched and imagined one pair, then the next one beckoned. No wonder girls had so many pairs of panties. The miracle was that they didn't have more. So many styles – bikinis, briefs, thongs, tap pants, boy shorts. I drifted among the aisles. An ocean of colors – beige, black, white, pastels, hot red, mint green, baby blue, pale yellow, royal purple, metallic silver, rich gold, racy champagne. And pink. Everywhere pink! My favorite PINK! The design selection was even larger – dots, stripes, contrasts. Cute bunnies, lovable puppies and silly sayings. How was a girl to choose? My reverie continued as I soaked it all in.

"Can I help you?"

I jumped. Then turned, and then froze. A pair of frilly, sheer, pink panties were clutched in my right hand. I was so lost in my fantasy that I hadn't noticed the salesgirl approach. With the abrupt return to reality, all my fears came back in a wave. They were compounded by the surprise.

"I'm sorry I startled you." she said with a look of concern on her face.

"Th…that's OK." I stammered, trying to slow my hammering heart and regain my composure.

She looked at the panties in my hand and said, "Those are very pretty. Would you like them?"

Before I could think, I said with a little too much excitement, "Yes, very much!" Then quickly realizing how that might sound, I added, "I mean no. I mean maybe." Suddenly, this shopping trip seemed like a very bad idea.

She looked at me quizzically. I'm slight of build and a little shorter than most boys and she was just a little shorter than me. She looked to be in her mid-twenties, with shoulder length brown hair pulled together in the back. She wasn't stunning, but had a healthy glow and an overall attractive, girl-next-door appearance. None of this was going through my conscious mind. It was quickly beginning to think solely about escape. But in the tight aisle, I would have had to rudely push past her. I stalled for time until I could make a break.

"What I mean is, I don't know. I'm trying to find a special present for my girlfriend. For the holiday. I'm afraid I don't know very much about this and I don't know where to start." Telling the story I had planned helped me regain my balance a little.

"Oh", she said with a nod. "That's fine. Don't be nervous. That's what I'm here for. I'm an expert. My name is Donna."

Relaxing a little further, but still on guard, I replied, "My name's Chris".

"That's a very nice name," she said with a warm smile. "So Chris, let's get started. As you can see, we have lots of selections." Donna waved her arm toward the merchandise and slowly started to move me further into the store. Perhaps she'd dealt with nervous customers before and didn't want to lose a sale by letting me get too close to the exit. "We have some of the best brands. All sorts of materials and designs. Do you have any ideas at all?"

"No cotton." I said.

"Of course." she nodded. "For a special present, something a little sexier."

"Yah," I mumbled, "that's what I was thinking".

"Good, that helps. Let's look over here." We moved past rows of treasures, to a section that, if possible, had even more erotic panties. She started to show me the various selections. She had me feel some on hangers and held them up from bins. "These are all very pretty, aren't they?"

I just nodded my agreement. As my nerves calmed, I got more back into the business at hand. A little excitement started to stir in my belly again. I began examining the panties with a more critical eye. With Donna's willing help, I might just pull this off.

"So, no cotton. Any ideas on styles? Perhaps a thong or bikini?" Donna suggested.

Continuing to finger a pair of beautiful, midnight black panties, I said offhandedly, "No thongs. I was thinking more about high cut briefs or tap pants with some delicate lace trim".

Donna stopped and turned to stare at me. She seemed to ponder for a minute, and then did a quick scan of my body, as if focusing on it for the first time. "You said you didn't know anything about this. You sound like quite the expert."

I did a mental head slap. Why couldn't I keep focused? Of course most men wouldn't talk about panty styles so casually and with such knowledge. This lingerie, and the anticipation, and the pleasure were disorientating me. I tried to quickly recover, "I…I think those are styles she mentioned."

She still seemed suspicious. Most of her previous talk had been light and airy. Now she continued in what seemed a more determined and inquisitive manner, "What size are we looking for?"

This was one of the things I had prepared for, "Size 7". That was the size of one of Rachel's panties that fit me best.

Donna smiled a little. She eyed my waist and hips as if making a professional assessment. Then she nodded to herself as if confirming a theory. I began to worry. "Size 7", she repeated. "That's about the size a girl with your build would wear."

My throat tightened. I didn't like the way this was heading. I didn't know what to say, and before I could say anything, Donna pressed on.

She paused for a second, as if doing a mental calculation, then looked me in the eye and asked, "What's this special girlfriend's name?"

My eyes widened. "Excuse me?" I croaked.

"You're buying these panties for a special person. What's her name?"

I felt pole axed and began to panic. My mind was blank. I hadn't expected such a question and I'm sure my jaw dropped. I couldn't speak.

Donna crossed her arms, shifted her weight from one hip to the other, and tilted her head to one side. She seemed to enjoy my discomfit. She kept me in her gaze. Her smile almost said she had solved a puzzle.

I knew hundreds of girl's names. But they all seemed to disappear. As the seconds stretched, my deception seemed more and more obvious. In desperation, I glanced around. My eyes fell on some panties with a floral pattern. My lips moved before my mind could think. "Rose", came out in a weak squeak. "Her name is Rose." As I said it, my face involuntarily squinched, as though even I didn't believe it.

Her eyes followed mine to the floral panties, and then returned to my face. We both knew she had caught me in a lie. We both knew I was trying to buy panties for myself.

I flushed beet red. My shoulders drooped. I was certain that she would call security and have me removed or arrested as a pervert. I glanced toward the exit and started to step away.

Donna moved to block my departure. "I think I better go." I mumbled.

She touched my arm gently and it was enough to stop my flight. She whispered in a low voice, "There's no need to leave. Everything will be alright."

I looked at her face and some hope glimmered in my despair. Her face seemed open. No trace of anger or disgust. Still, I was torn. Part of me wanted to leave and avoid further risk and embarrassment. Another part felt I had come too far to leave empty handed. I glanced again at the exit.

"I'm certain I can help you." Donna continued. Then she smiled and winked.

It tilted the balance. I decided to stay. "OK." was all I could muster.

"Great," she beamed. "Now Chris, why don't you go look in those bins. There's no one back there. I'll take care of these last customers and then we can spend some time together." I still didn't move. "Go on now", she said. "I'll only be a minute". She gave me a gentle nudge toward the back of the store. I walked off in a docile daze.

Donna waited a second to make sure I'd keep going. Then turned and moved off to the cash register. As I glanced back, I noticed for the first time her black patterned pantyhose. I also followed the gentle sway of her hips under the short, pleated skirt. My penis stirred. Amazing. Even under extreme stress, primitive urges emerge. I shook my head and checked my watch. Closing time. I didn't care. I was putting myself in Donna's hands and just seeing where it took me.

True to her word, she was back very quickly. "There," she exhaled in a friendly and reassuring voice as she rubbed her hands together. "It's just the two of us. The store is closed. No one will back come here. We can get down to some serious shopping."

Her casual manner and talking like this was a normal, everyday occurrence drained my tension away. In fact, it relaxed and excited me.

She looked at me and said, "Let's buy that special present for a special person."

It warmed my insides. I smiled and nodded.

"You said 'no thongs'. I can't blame you. They're a pain in the ass", she said without a trace of irony. "And 'no bikinis'. Let me guess. Not enough coverage." She glanced at me for confirmation.

I expected to be embarrassed by such a question from a stranger. But she was so professional, it seemed perfectly normal. I simply said, "Yah, that's right."

"No problem. We still have plenty of choices. First, we have to get this size thing down. How did you decide on a size 7?"

I was relaxing, but I didn't want to go into a long story about filching Rachel's panties. I gulped and shrugged and said, "They just seemed right."

Donna took it in stride. I liked her more by the minute. She started to instruct me in the mysteries of lingerie. "You see Chris, there are no standard sizes. Each company sizes their panties and bras differently. With panties, some companies label larger sizes a little lower, because every girl wants to feel smaller. It's the opposite with some bra manufacturers. It makes it all very confusing, even for experts. You just have to try them on for comfort until you learn how the brand fits you. Let me show you." She moved around the bins and racks expertly snatching up a variety of racy, high cut briefs.

She laid them out on the counter. "These are all size 7's. But they are all different." She held a couple of pairs together by the waistband and put them right in front of my face. "See. The front ones are much smaller."

I noticed the difference, but I was looking more at how pretty they both looked and getting more aroused by their proximity. I'd be thrilled to own any of them regardless of the slight variation in size. I licked my lips. Donna noticed my excitement and said, "Easy girl. Try to stay focused."

I giggled. This was becoming fun. In all of my worry about my first shopping trip, I never imagined it could be fun. Donna returned to sorting among the panties. I looked at her more closely. Maybe it was because she was so kind and non-judgmental, but she seemed to emanate an energy and intelligence. She was different from your garden-variety sales clerk.

"Do you work here full-time?" I asked.

"No. This is part-time," she said absently, engrossed in the business of finding merchandise. "I'm a grad student at the university. This helps pay the bills, and I get a great discount on my clothes."