Randy’s Grand Reveal

May 1, 2024 // By:analsex // No Comment

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I’ve known Randy since high school. We rode the same bus, lived less than a mile apart, were assigned to the same study halls and shared the same lunch period. This is not to say we were ‘buds’ back in the day but we were in shared company hundreds upon hundreds of times over a span of four years so we knew each other for sure. What I didn’t know, had no clue about, is that Randy was a crossdresser and occasional impersonator.

This was not a full-on lifestyle choice for him by the way, but more of an occasional ‘when I feel like it’ thing, so he told me. To me he is a pretty interesting guy and I’d like to share a story about him. I have his permission.

I would run into Randy at a local store or restaurant every once in a while and we’d say hello, exchange pleasantries and that’s about all. That is until our 10th high school reunion.

We are from a town of about 25,000 when everybody’s home. There is one public high school and back then there was also one parochial high school. We both went to ‘pub high’ which is now a large regional high school and has maybe three times the student population than when we went there. That’s only relevant because now days it’s unlikely Randy and I might have become reacquainted at a reunion gathering of some 550 alums. For us however, now some 15 years ago, it was 130.

I left home right after graduation to attend nursing school at a well known teaching hospital, Grant Medical Center, in downtown Columbus. Ours was an immersive program and first year students were required to live in dorms on campus. I shared a dorm room with a girl named Amber and then shared an apartment with her for our second year. I came back home to work after that and lived with my parents for nearly a year until I got set up.

Randy had gone into the Army Air Corps and was a licensed commercial pilot but hated to travel. That was and still is a conundrum for me but it’s his life. He flew charters out of the nearby regional airport, could be home most nights and was happy with that.

Randy was one of many alums that still lived here and was on the planning committee for the 10th. I too was still living in town, though I had left and come back, and was one of the first to respond when the invitations went out. Just by chance, I ran into him that week and he told me I was one of the first and also told me how he knew it. We shared a little laugh at that and it was a pleasant encounter.

The reunion itself was fun. Ours was a pretty small class and many of us had been together through grade school. Our beloved coach was there and was celebrating his final year at ‘pub high.’ What a huge ovation he got when that was announced. Our principal had retired but she too was there along with a few favorite teachers who, interestingly, seemed aware of that dynamic. Makes you wonder a little.

Randy and I talked and got swapping bus stories with a few of the others on our route, bus 81. Mr. Denver drove that bus all 4 years and we eventually came to accept that he didn’t have actual eyes in the back of his head. He made excellent use of the mirror above his head.

We’d gotten into a card game at the back of the bus one day and I won a pocketful of quarters from every one of those boys. They never let me forget that and we laughed about it that night.

Randy and I agreed to meet for drinks a couple of weeks later and we each had a few too many. I guess there is a certain level of trust and comfort baked in when you are with somebody you’ve known as a friend for that long but at any rate, we began revealing things about ourselves that were well into the realm of private.

Among other things I told him that I wrote erotic stories for online publication and he told me that he was a crossdresser. At that, I told him I was a closet exhibitionist which prompted him to reveal that he liked the nude beaches. I think that within the span of an hour, we each revealed enough to socially cripple the other. For myself anyhow, I was unafraid of that.

I hadn’t known anybody who was a crossdresser and I began asking him about it. He was open and candid and through the whole conversation I never felt like I was talking to an odd duck. He told me it started very early for him as a young boy and he would sneak into him mom’s bureau drawer and try her things on. The more he told me, the more questions I had and was impressed with how normal and down to earth he was, the subject matter notwithstanding.

I’m not sure what I expected in a conversation with a crossdresser but in Randy’s case he was…not sure of the right term but I’ll just say he was a pretty normal dude, maybe a little cool even. It started to get late and we both had to work the next day but agreed to stay in touch and maybe try getting together again sometime soon.

We went out about a week later and again after a couple beers got comfortable talking about our private lives. It was his turn this time to be the quiz master and he seemed particularly interested in my exhibitionism. I told him I had gotten hooked Kurtköy Öğrenci Escort as a young person while I was out waterskiing with girl friends. One of them issued a dare that we each make a topless run around our end of the lake. There were only two men still out fishing by the time my turn came but as I circled their small boat and got such smiles and waves from them, I was immediately thrilled and smitten with the experience. An exhibitionist was born that afternoon.

I think it was true for both of us that the more we talked the more comfortable we got and I had begun to see real compatibility. He kissed me that night and it was good.

He called me the following Thursday and asked if I was available on Saturday for an outing. As it happens I was free and I said so and asked what he had in mind.

“I’m headed over to Cross Creek for a couple hours. There’s a used clothing store there I like and I want to pick up a few things,” he said, “I’d appreciate some company if you’re interested.”

I knew Cross Creek pretty well. It was only about an hour’s drive to the east and I’d been there or through there more than once. It was more a village than a town actually and had the feel of an artist’s enclave. We’d joked many times when I was a high schooler that Cross Creek was where all the hippies went after they got old.

“Are you shopping for women’s clothes?” I asked.

“That’s exactly what I’m doing,” he responded. “Does that bother you?”

“Doesn’t bother me at all. Might be interesting,” I replied.

And so the date was set and he picked me up at noon. We had lunch on the way and got to Cross Creek just after 2:00.

Randy explained on the drive over that he was a frequent shopper at “Who Says” and they knew him there. They never judged him and had, on a few occasions, helped him select and try on various items. Today that’d be my job if I felt up to it. I said I’d give it a try.

Well, it turns out that Randy was more than just recognized there, he was something of a celebrity. He was warmly greeted by name and introduced me as a friend since high school. At mention of that I was almost instantly granted ‘insider’ status, or so it felt.

“We’ve set aside a few things for you to look at since you called the other day, Randy,” he was told. “They’re waiting for you back there.”

He took me my the hand and led me to one of the fitting rooms at the back of the store. “It’s totally normal, even expected in a place like this for you to come with me Connie, so here’s your last chance to stay back. I’m not going in there only to have to pretend modesty just because you’re in the room.” He looked square at me.

“Nope, I’m good,” I said in reply and in we went.

There were a number of garments waiting his inspection and prominent among them was a silky black bustier. He held it up. “What do you think of this?” he asked.

“It’s beautiful but it’s used,” I said. “Are you comfortable buying intimate apparel that you know is used?”

“Comfortable? That’s the whole idea Connie, for me at least,” he continued, “particularly as it concerns intimate apparel.” He slid out of his shirt to try on the bustier. “Help me on with this,” he said, lifting his arms straight up in the air.

Something akin to a purr escaped him as I helped slide the garment over his head and on down over his torso. I’ll have to say that got me going a little.

“Ok, now hand me that red skirt,” he said and I reached for it.

He dropped his shorts to try the skirt and I was immediately dumbstruck – foolishly so, but dumbstruck nonetheless. Here I am at a used clothing store, shopping for women’s apparel in the changing room with an admitted crossdresser and I was caught off guard at the sight of him in his silky lace bikini briefs. They featured a sissy pouch which I’d never before seen in person and I must say, it was rather well filled out. They were opaque white.

I drew that breath so suddenly and so spontaneously it surprised both of us. He looked at me with raised eyebrows. “What?”

“Well I feel a little stupid,” I began, “but it surprised me to see you in those girlie underpants…even after you gave me fair warning. Sorry Randy, no offense taken I hope.”

“Ok, fair enough,” he said, “I’m not offended but I’m also trying not to laugh at you right now. You know you’re blushing, right?”

“Yeah, that’s going to make me feel better, dumb ass,” I said, showing him my middle finger. We both laughed. I picked up the red skirt and handed it to him.

This would take a little getting used to for me. Seeing these clothes on a guy felt a little off at first but seeing that bulge in the front wasn’t so bad. I had a sneaking hunch that maybe I could like this.

Variously over the next half hour or so he tried on a white satiny camisole, a short red plaid skirt with mini-pleats, two pair of black leather hot pants, brick red and jet black fishnet thigh highs, three different leather vests and assorted bikini panties. As Kurtköy Çıtır Escort he prepared to try on the first of these he asked me to avert my eyes.

“Avert them where? We’re in a fucking five foot closet for chrissakes.” Again we laughed but it was nervous laughter

This first pair was a high cut French style panty of a nearly sheer cream colored material. He was really nervous I could tell and switched into these in about the time it’d take a normal person to draw a breath. We were, I reminded myself, way fucking removed from any normal I ever heard of.

As he snugged these up on himself it was more than plainly obvious why that sissy pouch had been so well filled out and the fact that he was fully shaved was also entirely obvious. He caught me staring, I couldn’t help myself.

Again with the raised eyebrows.

“C’mon Randy,” I said with a chuckle, “cut a girl a little slack here.” Trying to keep it light, I continued, “I’ve never even seen you in swim trunks and now, in the span of less that an hour, you’ve gone from normal street clothes to nearly naked, your junk on display and it’s a lot to take in,” I concluded. I was feeling a little exasperated.

“Alright, I get it,” he said in response. “I’m used to this, used to these clothes and used to the people here helping me try this stuff on. But it’s brand new for you, so I get it Connie, honest. No more funny looks, ok? I promise I wasn’t meaning to make fun of you.”

I nodded and offered a smile and I meant it. I signed on for this after all, he’d been honest about it and beyond a little initial shock, I was ok. That lasted about 10 seconds.

“Well ok then, I guess that’s settled but all this talk has had its effect,” he said, looking down.

Sure enough he’d gotten a hard-on.

“I guess it’s my turn now,” he said.

“Your turn what?”

“My turn to say no offense taken, I hope.”

“Ok, none taken,” I responded flatly, “What’s your next trick? You going to make lightning shoot out your ass?”

“Hey, hey! Woah there.” He just stared at me. “Shit, you’re really pissed aren’t you?”

I stared back.

“Ok, I yield,” he began. “I shouldn’t have drawn your attention to my erection like that. It just happened and I can’t apologize for that part but I responded to it like a preening teenage boy showing off. ‘Oh, oh look at me. I’m such a stud.’ I was an asshole, Connie. I apologize, really.”

He looked so forlorn, crestfallen even. I could tell he was sincere and trying hard to make it right. I felt my anger ebbing quickly away. Again I reminded myself that 95% of this was predictable and I just couldn’t stay mad. Besides, his mighty atlas rocket had slumped back down onto its launching pad by then.

“Ok mister, apology accepted. Let’s just move on. I’m ready to put that behind me.”

He gave me a funny look. One eyebrow went up. He grinned at me and I suddenly realized what I’d just said. He knew what I’d meant but it was funny.

I grinned back, slapped him on the arm and said dismissively, “Alright, enough.” I offered my hand, he shook it and the moment was gone.

It took only another few minutes for him to try on the remaining underpants and having made his selections, he paid for them and we left.

I think it very odd but we didn’t talk about the events of the changing room all the way home. He wanted my opinion on the things he’d gotten, of course, and I freely shared my thoughts. I have to give credit where it’s due, the man has taste in women’s clothing.

We stopped for a beer before he dropped me off at home. All in all, save a couple queer ass moments, it had been a pretty fun day and I told him so. He agreed, gave me a quick hug and off he went. He got busy and I guess I did too because neither of us called the other for a week or more. I thought about him several times and smiled each time. I think I kind of liked the guy. It felt good.

There was a note on my door the following Thursday when I got home from work. It was from Randy. It read, “Connie, Sorry to miss you but I wanted to bring this by in person. Check it out. It’s an invitation to a crossdress party Sunday afternoon. I’ve been to these before and I’ll know most of the ‘dressers’ there. It’ll be a real hoot. There’ll be plenty of straight people there too. I want you to come with me, Connie. If it gets too over-the-top for you, we’ll leave, OK? Please say, ‘yes.’ I’ll call you tomorrow.”

He did call and he did convince me to go with him to the party. We agreed if I wanted to leave that we would, immediately and without discussion or protest. In turn, I agreed to keep an open mind.

He picked me up just after noon and we went downtown for brunch. The party was to start at 3:00 and we had time to do some window shopping before heading over there. No surprise that most of the window displays we stopped at were women’s fashions. That suited both of us.

Randy assured me on the drive over that he totally meant what he’d said about leaving immediately Kurtköy Elit Escort if I got too wierded out. There were very few rules he explained, but one of them was no nudity. “There are only 3 or 4 of these ‘dresser’ parties a year and it’s a highly coveted invitation. You screw up like get naked or start a fight or bring in hard drugs, you’re out for a year.”

I told him again that I was going in with an open mind. That made him smile. This was obviously a pretty big deal for him and I really wanted to give it an honest try but I was a little nervous and admitted to that much.

The party was in a 3rd floor walk-up in a nice looking neighborhood on the west side. I had visited some clubs in that area before and I felt safe. As we rounded the 2nd floor landing he asked me if I was ok. I smiled and nodded. He took my hand.

We arrived at the door just about on the hour. It was open and the apartment was already crowded. I was immediately and powerfully struck by the spectacle of what I saw. It was like a pie in the face. I didn’t see it coming and the impression was full on me in the span of a lightning strike. It blew me back a little; a room full of men, men who were obviously men, dressed head to toe in women’s clothing. It was just crazy, like seeing a pig fly past your window. I’d never seen anything like that before in my life. I think maybe my jaw dropped open but I hope not.

I don’t know what precisely I thought I’d see but this wasn’t it. I guess maybe I thought I’d see mostly singles, perhaps some of the men noticeably effeminate but not so. They were in couples, man-woman couples, mostly middle aged and outfits aside, appeared otherwise normal and unremarkable. The women especially, while stylishly dressed, looked like anybody you’d see in line at the grocery.

Randy took me around to meet the men he knew, which was most of them. I met a banker, two lawyers, a very large biker looking dude loaded up with tattoos and facial hair, a high school math teacher and a some others I don’t remember much about. It was surreal.

These men and their partners, wives mostly, greeted us so warmly and so conversationally I had trouble fitting the sound with the picture. I fought to process what I saw with my own eyes. These were men with men faces and men voices, smiling and talking so earnestly with us like it was all completely normal and yet they wore skirts, blouses and dresses. It was dizzying.

The disorienting effect was short lived thankfully and I was quickly becoming more and more comfortable. And I have to add that I was also finding the whole experience rather fascinating. There was every size, shape, skin color and age group represented.

I said earlier that I thought Randy had pretty good taste in women’s clothes and I can tell you he wasn’t alone in the room on that score. The fellow I remember as the math teacher, for example, was the very picture of evening fashion. He wore a plain black shift, just below the knees and was slender enough to pull it off. His necklace, white pearls in a strand long enough to be doubled up on itself, created the appearance of two strands. His earrings, pierced of course, featured a single pearl on each side hanging from a thin gold chain.

He wore close weave black fishnet hose with open toe, two inch black heels – spiked, naturally. A thin gold chain hung loosely around his right ankle. If there was any symbolism there, left vs right, it escaped me entirely though I’d ask Randy about it later. His left wrist was adorned with a set of three round ring bracelets in colors I’d describe as gold, rose and sterling. He carried white gloves, didn’t wear them but carried them in his left hand. Interesting I thought.

And one of the lawyers was a standout also as he seemed dressed for the captain’s cocktail reception on a Caribbean cruise. He wore linen trousers in Navajo white and they complimented his long slender frame. His color-matched, long sleeved tunic came to below his waist and was embroidered at the wrists with small flowers of a brighter white to set them off. He wore a strand of tiger eye golden beads around his neck and a matching bracelet. He wore dressy white sandals. Stunning, really.

While those two stand out in my mind, virtually all the other men’s outfits were thoughtfully put together as well. I admired many of them and laugh at myself now for wondering how I might look in any number of them. I was soon to find out, however, that the comely, tasteful and sometimes even bold appearance of those outfits was not to be outdone by the garments hidden beneath.

The persistent murmur of conversation in the room took on a different character in rather an abrupt fashion, I thought. Where there had theretofore been a dozen or more pleasantly muted conversations underway, there was now a more than obvious exchange of expectant glances here and there among the guests. Randy took me by the elbow and whispered that the evening’s grand reveal was about to begin. When I asked what that meant he just told to watch and enjoy.

The host took a position atop the stepped fireplace hearth and spread out his arms toward the crowd until everyone fell silent and turned their attention to him. He told us to freshen our drinks and take seats in the great room as the evening’s ‘Grand Reveal’ was about to begin.

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