The Real Raquel

The following is something I could never tell another living soul face-to-face. But I have to tell someone. I have to get it off my chest. So, I'm sharing it with you, my readers.

This story is mostly "Transgender & Crossdressers", but there's a little bit of "Gay Male", a little bit of "Fetish", a little bit of "Anal", and it ends with a little bit of "First Time". It's 100% the truth.

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I finally did it. I'll tell you what "it" was towards the end, but I want to first tell you how I got to where "it" is.

Recently (in the last year and a half, or so) I began writing a series of T&C stories here on literotica.com about a fictional character, Raquel. Believe me, I'm no Raquel. I'm a 56 turning 57-year old dude, about 5'10", 195 lbs. No one would ever mistake me for a girl. But, I've always been a little gender dysphoric.

Raquel's story and mine, however do share some similarities. I AM a closet crossdresser, the way Raquel's story started out. I began masturbating wearing my older sister's baby doll nighties very early on. Later, it was a pair of my mom's pantyhose, that she might have discarded because of a small run. With either, I would hump a pillow, my shaft hardening with the frictionless pressure between the nylon and the pillow. Sliding up and down on it, in and out, fucking it, until near the end, when I would pull back, grab a stack of tissues placed nearby, wrap it around the head and shoot my cum into it.

Other times I would lay back with my legs spread wide and let the pillow "do the fucking". I would grab it by the "ass" and pull it up against my crotch, then push it back down. I don't really remember thinking I was the woman in this situation, but looking back, it's clearly homoerotic. It ended similarly, regardless, with me rubbing my cock until I exploded, quickly grabbing the tissues to catch my cum in the end.

I'm extremely turned on by the thought of eating my own cum, but the experience never lives up to the hype, for me, at least. When the urge does strike me, I have multiple masturbation loads hidden in a pill bottle in the spare refrigerator, that I can sip from while I'm jerking off, because once I orgasm, the desire evaporates. So, I'm unlike Raquel in this department.

Once, before my wife and I met, in a drunken moment, a gay friend and I sucked each other's dick. Blowjobs aren't as easy as they look. It took a while before I could make him cum. That's the extent of my experiences with men, though. I never look at a guy in person and think to myself, "He's hot, I wonder what he's packing." Yet, I gravitate towards gay and transgender stories, here on Literotica. I obsess with thoughts of sucking a cock and being fucked in the ass. I don't understand it. It's the female genitalia, in real life, that has brought me the most sexual pleasure.

I've been faithfully married for over twenty-five years. My wife (who shall not be named; all the names in Raquel's stories are pseudonyms, by the way) and I share a great relationship. We almost never fight and it's almost always over little shit that we get over quickly. Like most dating and newly married, young couples, we had sex often in the beginning. The sex has grown less frequent, now, but whose hasn't after that many years together. When we do have sex, oral and the occasional anal are still in play.

I always looovvve to lick her pussy. And she likes me doing so. Going down on her is a huge turn on. Making her cum with my tongue and fingers gets me harder than just about anything else. Maybe it's the lesbian side of me that's always been there in the background.

She never hesitates to suck my dick, either. Usually, it's part of our foreplay. Sometimes, she really wants me to cum in her mouth, although I rarely do. It's a shame that I've never been able to cum easily that way. Most of the time, after a while, I have to tell her to stop, that I just want to cum inside her, which I have no problem doing and which she enjoys, too.

As for the previously mentioned anal, my wife and I have both bought numerous toys over the years for assplay (my ass, to make things clear). They've all been very non-phallic. She normally buys just the usual torpedo-shaped vibrators and such. And I purchased and wore out a vibrating buttplug. Don't get me wrong, anything is better than nothing. I use the toys on myself fairly often when she is not around. I recently purchased 6.5 inches of remote controlled, insertable, vibrating, silicone anal beads. They come into play, later.

And she likes me to fuck her ass, too. That only happens about once every three to six months, when we've had a bit too much to drink. But, hey, it happens. Her ass is sooo tight. I can usually only last a very short time, once I start stroking in and out. She usually finishes herself off with a clit vibrator.

I didn't have any panties when we married and hadn't worn lingerie in years, but about 5 years into the marriage, the yearning returned. I started secretly borrowing a pair of hers once in a while, then started acquiring my own.

When I say I'm a closet CD, it's not by choice. About 15 years ago, I did make an attempt to come out. I tried to ease her into it, to test the waters. I'd had my small stash of panties I'd kept hidden for years, and only wore to masturbate with when she wasn't home. It was around that time that I found and created an account on www.menwearpanties.com, a now defunct website and forum for and about, well, men who wore panties, d'uh. I even used "Raquel" in my user name back then. In case you're wondering, this is an homage to the gorgeous Raquel Welch, who I idolized in my younger days.

Some of the other members on menwearpanties.com suggested a way to broach the subject with one's significant other. I decided to give it a try and set my plan in motion.

After a shower one evening, I feigned running out of clean, boring, cotton, tightie whities (I had secretly thrown out a few pairs that were wearing out and buried the last few clean pair in the laundry hamper) and said, "Well, I guess I'll just have to wear a pair of your underwear." She didn't freak out. She just laughed, and said, "Okay." I thought to myself, "Oh boy! This is it, I'm gonna be a panty wearer!"

I distinctly remember the pair of Victoria's Secret, black, high-leg cut briefs she handed me from her panty drawer. Nothing special, but, OMG! PANTIES! IN THE OPEN! IN FRONT OF MY WIFE! I slipped them on, trying not to be too obvious in my elation. I put on a pair of baggy shorts and a t-shirt to hide my erection while we fixed dinner and ate. Then we watched a movie in bed. During the movie, I had stripped down to the panties and surreptitiously, slowly stroked myself under the blankets.

By the time the movie was over, I already had a big wet spot from all the precum that been leaking out. Before we turned out the lights, I reached over and took her hand and placed it on my panty-clad cock. She took the hint and began rubbing me through the panties. Then she started to pull the front of the panties down to expose my cock and I stopped her. "Just rub it some more," I said. She did so for a few minutes, then, I guess she got turned on, so she pulled them off, pulled me over on top of her and without saying anything, grabbed my penis and slid it inside her pussy. We both came pretty quickly, but no more mention was made of the panties.

Well, the next day, I went out and bought a five-pack of Hanes nylon panties with lace waistbands. That night, I knew she hadn't had time to do laundry during the day, so, after my shower, I went to her panty drawer and grabbed another pair of hers (I didn't want to show my hand too quickly and reveal that I had rushed out to buy my own). I didn't pick anything too girly. Again, the sex was hot and heavy, once she pulled my panties off.

The third night, after my shower, I put on a pink pair of the Hanes panties. When I went into the kitchen, she asked, "Did you see that I did laundry today?" I answered, "Yes." But said nothing more.

At bed time, I took off my shorts and t-shirt, revealing my new panties. She looked surprised. "I thought you said you saw the clean laundry."

"I did, but, I like the way these feel," I answered.

"NAME OMITTED, I don't know about this."

"What's wrong?"

That's when I got the dreaded, "Are you gay?"

"No. No, sweetheart. I just thought it was okay with you."

"Then why are you wearing panties all of a sudden?

"I just like the way they feel."

"Well, they're pink. They're women's panties. I don't think I like it. I'm not lesbian. It feels wrong." And a whole litany of societal crap she couldn't overcome came tumbling out. She expressed an aversion to crossdressing. She practically had a meltdown.

"Okay, honey. That's okay, I'll get rid of them." I returned to the closet, literally to get a pair of "men's underwear", and figuratively. It took a while for her to get over it. That was the last time she saw me in panties. Luckily I hadn't told her about the six or seven pairs I already owned (some of which were quite girly) or she would have probably totally freaked out and I don't know what would have happened. I can't blame her, though. I kept the panties, anyway.

So you see, Raquel and I are not that similar.

Over the years, I've been through the typical binge and purge cycles of many CDs, although, never throwing everything out, keeping a few pair of panties each time, telling myself I would only wear them occasionally, just to find myself with fifteen to twenty pairs again within a year. The urge was irresistible. At one point, I switched to lycra boxer briefs and would slip on a pair of panties before putting them on so I would have a double layer on nylon to rub against each other and against my dick, and to hide the panties.

It seems that, rather than getting over the urges, the desire burns brighter as time passes. I sneak a pair of panties on almost every day and am wearing them as I write this.

The hunger continued to grow. Seven or eight years ago, when my wife put a whole bunch of boxes of clothes in the garage to donate to a charity thrift store, I sorted through them and found a few things that fit me. They might have been a little tight, but she is almost my height and has gained a little weight each year we've been together, so I could squeeze into them. I managed to put together a couple of outfits, that I hid away. This only made me want to feminize myself even more. Over time, I started going through her donation piles and added a few pieces of costume jewelry and some shoes, including heels she couldn't wear anymore because it hurt her knees to wear them. Her shoes are only about 1/2 size too small. I wound up with flats, Yellow Box sandals, ankle boots, platform sandals, 3, 4, and 5-inch pumps.

Five or six years ago, I began experimenting with her makeup. I found a multicolor palette of eyeshadow in the bottom drawer of her vanity along with several forgotten tubes of lipstick. I started checking her wastebasket for discards and picked up even more items. The appetite grew. I wasn't going to get everything I needed from her giveaways and throwaways. I would have to buy things.

I bought garter belts, stockings in black, white, and several nude or natural shades. I bought waist shapers. I bought bras. I bought a pair of black leather boots that came up nearly to my knees and a pair of light tan suede ankle boots. I even bought a couple of cheap wigs. I bought fake fingernails and nail polish. I bought false eyelashes. I bought a half dozen pairs of clip on earrings. I bought mascara, foundation, rouge, setting powder. I bought lipstick. I was becoming obsessed with looking like a woman. I had to buy a couple of tool boxes from the hardware store to keep it all in and hid them away with the rest of my stuff in the garage.

I dressed up only when she would be out very late with friends or overnight at her sister's or mom's or shopping all day. I would track her iPhone to know when to start dismantling all of my work. Twice, when she was out of town for the weekend, I dressed completely all day and ventured out, under the cover of darkness, to buy a pack of cigarettes at a convenience store or go into Walmart to grab something real quickly and use the self checkout. I mostly avoided interacting with people. It was still thrilling.

About two years ago, I decided to wear an earring on my left earlobe when I was away from the house. I even started to wear a simple one around a circle of my friends, with whom my wife never has contact. It kind of took them by surprise, but now it seems normal to them, even though it's still the topic of a joke or two sometimes. Little do they know.

Once I forgot to remove it when I got home and my wife quizzed me on it. I acted like it was nothing. Still, I don't wear one around her, lest she dig too deeply.

One major difference between my character, Raquel, and me, as I mentioned above, is that I am a smoker. In my psyche, smoking has always been taboo, and thusly, has always played a role in my erotic fantasy. This fetish, too, began at an early age. I am particularly fond of "feminine" brands, such as Virginia Slims, Misty, and Capri, menthol, specifically. I actually get aroused thinking about lighting up, and while smoking. The slender phallic expression of holding a skinny cigarette and placing it between my lips feels sexy. As a matter of fact, my very first encounter with literotica.com was a smoking fetish story I found while searching the internet.

Shortly after or coinciding with the decision to wear earrings in public (just not around my wife), I developed a compulsion to wear lipstick more often. I'd even put it when I was working in my home office, while she is in another part of the house, just to wipe it off thirty minutes later when I walked to the kitchen for another cup of coffee. A bright lipstick print on a glass or cigarette filter is a sexual trigger.

No, I don't wear it around my friends, either. But, before face masks, I would wear it in public whenever I thought I wouldn't possibly encounter someone I knew. Particularly whenever I'm behind the wheel, smoking a cigarette.

Sooo, just this past October, I had to drive to a nearby city about an hour away for work. Naturally, I put on lipstick for the drive over and during the drive back.

Well, I wiped it all off before arriving home, but my dumb ass forgot to wipe the rim of my travel coffee cup when I set it by the kitchen sink. She noticed the lipstick on the coffee cup

"Where'd the lipstick come from?" She asked. "That's not my shade."

Oh shit! I just kinda shrugged and said, "Huh."

She dropped it. It was a Wednesday evening and my wife was heading to the beach for a four-day weekend with her friend and her friend's daughter and the daughter's friend the next day. I hoped she would forget it or drop it. I hoped she didn't start thinking I was having an affair or something like that. She left with her friend and the girls Thursday morning.

Thursday afternoon I got a text. "Are you going to explain the lipstick on the coffee cup?"

I texted back, "I was wearing lipstick yesterday. We can talk about it later." How else could I explain it? What was I going to say?

I spent the next three days agonizing over what I would tell her. I also spent it painting my fingernails, wearing makeup, dressing up and masturbating. Sunday morning came and I threw out just about everything. I thought this was the end.

Sunday evening, after she arrived home and settled in, she, asked again about the lipstick. I was dreading this, but I had decided I would just tell her some of the truth. I had tried some of hers on a while back to see what it was like and had developed a fetish for it. I often played with my dick to pass the time while driving on trips and wearing lipstick was arousing. I told her I couldn't explain why it was so, it just was. That's all it was, a weird sexual fetish.

She seemed satisfied. Maybe she suspected it was more. Maybe she didn't want to know more. We haven't spoken of it since.

I recovered a lot of what I had thrown out, before garbage pickup day and hid it back in the garage.

I had shown her the other side of me three ways over the years, panties, earrings, and now lipstick. She either couldn't admit it to herself or knew, yet chose to let me be who I was, as long as she wasn't confronted with that part of me. I know she loves me. I just wish she loved all of me. So different from Raquel.

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We, you and I, dear readers, are now to "it".

Last week, I had to travel to North Carolina, on business, for three days. My first such trip since the pandemic began. I packed for work and play. I was a little apprehensive about what the TSA might do if they screened my checked baggage where all of my nighttime supplies had been packed under everything else and they selected it for a random inspection. Luckily, everything arrived untouched at my final destination.

When I was done with work for the day, I checked into a nearby hotel. In my room, I Googled gay bars near me. I read the reviews and selected a bar about 20 minutes away, Jack's Tap, in Fayetteville, NC, described as a dive bar. I hoped I made the right choice. I hoped no one would notice me. I hoped I would be noticed. Not as in, by someone I knew, just by anyone. I hoped it didn't turn disastrous. I showered and shaved and rubbed a powder-scented deodorant in my armpits. I was already nervously anxious enough and didn't want sweat stains to ruin things.

I looked at myself in the mirror. From the waist down, I didn't look too bad. I'm generally fit. My legs and ass are still my best assets, shapely and firm. My abdomen was not as tight or defined as it once was, but I didn't have a gut. My chest was moderately hairy. There's nothing I can do about that without giving everything away. My arms and shoulders ... well let's just say, while I'm no linebacker, they aren't womanly. My neck and face say, "dude". My hair is short and graying slightly around the edges. Which didn't matter, I was planning on wearing a ball cap tonight. I just wish I had thought about shopping for a ponytail extender I could pull out through the back of the cap.

I laid my suitcase on the bed. I unpacked everything thing on top and set it aside on the bed. I came to the nude stockings, skinny jeans, long-sleeved maroon t-shirt, black 38C bra with off-white cups decorated with black lace, matching off-white bikini bottom with black elastic trim and the same lacy pattern on the front triangle and black see-through sheer mesh triangle in the back, black camisole I would wear over the bra, and my homemade breasts.

The breasts consisted of a small amount of uncooked rice poured into the toe of a stocking, twisted a few times, turned inside out and pulled tightly back over the toe, where I tied a small knot and cut off the excess material with scissors. The knot forms a nipple about the size of a pea. Not truly realistic looking, but they fill out my bra cups and the added bonus is the stocking nylon constantly rubs my real nipples, sending shocks through my body to my crotch.

The first thing I did was apply my lipstick, Revlon Super Lustrous Crème, No. 725 "Love That Red". I started by outlining the perfect kiss and then filled in the rest. I felt an immediate transformation.

I slid the bikini panties up my legs, kept smooth as part of my manscaping. Nothing ever said about this by my wife. I rolled my semi-flaccid penis to the left and tucked it between my legs, so the frenulum faced out and the panty gusset would absorb my precum and hold me in place. I pulled them up snugly and pulled the side straps up over my hip bones.

Next, I rolled the stockings up my legs, as I'd done many times before. The nylon on my smooth flesh causing my tucked manclitty to stiffen and throb. I wrapped the bra around my chest and tried fastening it behind my back, again, as I'd done many times. My hands were trembling and I couldn't do it, so I had to fasten the three hook-and-loop devices in the front and spin the bra around old school. I slid my arms through the straps and inserted my "breasts" and adjusted the cups. I gave them a squeeze and rubbed them up and down and side to side making my natural nipples harden.