Well, this may not be terribly erotic, but it will be different. And after nearly 7 years on this blog expression of futile romantic plight, different is in short supply. So join me, will you, as I go on a journey of self indulgence.
How do we meet? Well, if it’s a dream, it could be because we happened to meet in the street at pure random, and you happened to like how I smiled, or my eyes, or the cut of my jib. Or maybe because you know one of my friends, who decided to introduce us because they knew you’d be perfect for me. But, this is a romantic fantasy, not science fiction. So how about the way in which would be most comfortable for me as well as cater to my ego, since it wouldn’t rely on random luck, or a friend, or even you, to do the heavy lifting for me?
So, we meet via an online dating website. I join it and upload the few flattering pictures I have of me. I examine the publishing criteria and write the best bio I ever have. I am honest yet witty; creative yet concise (now you know this is a fantasy). I input my measurements, which are hardly the worst but not terribly flattering (while shaving off about ten pounds, as one does online). I come off as both imaginative yet hard working; funny yet appropriately serious. In other words, I achieve the dream; I come off as more appealing than the guy with the mirror selfie and the guy making duck lips in a sweatshirt. I am, simply, your above average single dude in his late 30’s. And in the world of my dreams, being considered above average is all I could ever hope to be. I am a B+ Man and I know how to flaunt it. Heck, I am even honest about living with my handicapped mother, and because this is the world of my dreams, this comes off as a quality of tenderness instead of evidence that I am immature or broke.
And then we make our first interaction. My profile is barely up twenty-four hours when you instant message me. You give me five stars out of five. You give me a brief yet flirty greeting, perhaps mirroring that famous line by Mary Jane Watson: “Hey tiger, you just hit the jackpot.”
I read your own bio with bated breath, not quite believing I have gotten so lucky so soon even in my own dream. Of course you are physically my type, and I yours. But our bios are compatible, too. You have a professional job within the arts; perhaps as an editor of a major book publisher’s graphic novel division. You list similar interests in comic books, anime, media, and so on as I do. You also volunteer on occasion and above all, stress that you are looking for a sensitive man who can make you laugh more than one with abs of steel, a hypnotic smile, or a six figure bank account. You are down to Earth and value the little things and the tender moments more than big spectacles. You care more about an intoxicating brunch more than a star studded night on the town. And because this is my dream date, you even boldly proclaim that you have always wondered what it would be like to be able to take charge in the bedroom and groom a man not so “traveled.”
“Hey there yourself. Love the Spider-Man reference. Want to swing somewhere for coffee or your beverage of choice?” This is what I text back after perhaps an hour of hand ringing and anxiety about having gotten so lucky so quick. This is as clever as I can be in such a circumstance. Even in a dream, I am in a state of disbelief. But, you are patient and eager to meet the man behind the profile. You quickly agree and suggest a trendy yet inexpensive local place within the city which has both indoor and outdoor seating for the upcoming Friday evening.
For the days leading up to our meeting, I am a mixture of emotions and clashing thoughts in the vague shape of a man. I am excited that my bio has worked so well, yet terrified that I am somehow far more charming than I realized. I am giddy that a date with a woman who is so compatible in looks and interests happened so quickly and easily, yet also anxious that such fortune rarely comes without a price to pay. There is an extra spring in my step, more of a hint of a smile in my voice, and more of a sense of fulfillment and energy to my soul. At least for a week, I am no longer the Dateless-Man. I am a man with a date and a chance.
Yet there is also a tremendous pressure, despite my best intentions. I tell myself that this is only a first date, and that anything can happen. I insist that even if things don’t go well, the very fact I got a “bite” so quick proves I can be appealing and the effort was worth it. And I try to tell myself that this is only the beginning, and I should not pin all of my hopes and ambitions for an unfulfilled romantic life on this one seemingly perfect sounding date with a professional geek-girl. Unfortunately, despite all of my experience in sales, the one person I have never been able to “pitch” is myself. And as much as I try to tell myself to relax and play things cool, I also tell myself that I cannot afford to botch thing like I did all three of my other dates.
It is my dream date with my dream woman, and I am both eager and petrified.
So it is finally time for us to meet in that outdoor table at that local, trendy eatery. This naturally in a setting with seasonable weather and no Covid-19, which already sounds closer to a science fiction premise now than it should. I’m properly groomed and dressed, and since this is a dream date, I would be wearing one of my nerdy t-shirts under a sports jacket and some nice jeans, and this would be considered dress appropriate since this is supposed to be semi-casual, not formal.
You arrive wearing a nice jacket and appropriate top, a short skirt and boots. We actually both arrive at the same time, for maximum irony as well as because I can be impatient sometimes. We both have a good laugh about it as it turns out we were both on the same train, several cars apart. Some might call it a “meet cute” moment. We each order a drink and some food and begin our date. Like many dates it begins with some obligatory small talk. Just to confirm some of the information from our profiles and so forth. No one is really interested in it but it’s much commercials before a movie in a theatre. It can’t be skipped so let’s just grit our teeth and move on.
Once that is dispensed with, you get into some more meaty conversations with me, and since you are an intelligent and sassy dream woman, this also means you’re able to break the fourth wall quite a bit.
“My name’s Fantasia, which of course means ‘fantasy’ in Italian,” you say as you sip your drink through a straw, which I notice since it means an excuse to focus on your lips for a moment. “It’s not bad as far as names go.”
“Thanks,” I answer. “I was hard pressed for a while.”
“For a dream girl, I’ve noticed you really haven’t focused much on my physical looks,” you continue with a raised eyebrow. “I mean most guys would focus on my hair color, eyes, skin type, blah blah. This is a fantasy, you can’t be that partisan deep down, right?”
“Well,” I reply as I shift in my seat. “I can’t say I have that rigid a type. It’s not like I am only chasing after white women, or Asians, or so on. I could care less about hair color or so on. Many different types of women are attractive to me. I’m very flexible.”
“I’ll be the judge of that later on,” you tease with a wink. “But just so I’m not an amorphous blob in a skirt and sexy boots, is it okay if we just settle on some visuals? How about me being mixed race so I’m a little tan, with brown eyes. And I know you’re not hung up on hair color, I know you like more unusual dye jobs a little more than, say, blonde or brown. Right?”
“Um, yeah,” I reply, a little surprised. “But it’s not like someone who’s a brunette or whatever is a deal-breaker.”
“Of course not. So we’ll say I have black hair and some roots are showing but I died it purple, and it matches my lipstick and fingernails, alright, sweetie?” you state back. “I mean it’s your dream date, you don’t need a disclaimer on it, right?”
“Right, I guess,” I say back.
“I think it says a lot that this is your dream date and I’m kind of taking charge here,” you say, as you look down at your own body. “I’ve noticed I am a little voluptuous without being too lean. In fact Cosmo might say I should lose five or ten pounds but I don’t agree and neither do you.”
“Who really takes Cosmo that seriously, anyway?” I reply. “That is an awesome skirt, where did you get it?”
“Do you really care or are you just running with advice you read that said to compliment a woman on something other than looks so you don’t seem shallow?” You tilt your head and smirk.
I shrug. “Both?”
“Good answer. I got it on sale at this cool boutique I know,” you respond quickly to get it out of the way before moving on. “I also find it interesting that we share some interests but you didn’t just mirror all the stuff you like. Just at random I like Doctor Who, Sailor Moon and horror movies and you’re not especially wild about either. Why?”
“Someone who just mirrors me on everything isn’t a dream woman, it would get boring,” I reply bluntly. “I’m game to try some new thing so long as she willing to, too. Or even if she’s not. Maybe my willingness would rub off.”
You take a few moments to nibble your food as I do. “You’re pretty idealistic for a cynic.”
“Most cynics are frustrated idealists, ” I counter. “But this is becoming all about me. Your job sounds fascinating. I’ve love to hear more about it.”
“It’s one part creative and two parts hectic and full of deadlines. I have so many manuscripts to approve and edit, and then I have to contact the creators, and then help with the ad campaign for the books,” you answer excitedly. “But it’s all worth it to be on the cutting room floor of some great, fun stuff. I can be there to help nurture media for a new generation, and make it more diverse, y’know? Have you ever read YA comics?”
I nod. “Actually, yeah. I used to get review copies from a big publisher and I’ve reviewed a lot of them. I haven’t read one which was outright terrible.”
“That’s because they have better editors,” you say proudly. “And it has to appeal to more than old guys.”
“Yeah, definitely,” I reply. “I love seeing your passion about it.”
“You sure you want this kind of conversation on your dream date?” you ask, a bit curiously.
“Sure,” I reply with a shrug. “I like getting along with small talk. This is a dream date, not pornography.”
“Touche,” you respond as you finish your meal. “I just wonder if you want to skip ahead a little, is all.”
“Skip ahea–” It finally dawns on me. “We could do a montage. Is that okay with you?”
“Sure,” you say back before snickering. “It’s my first montage. Be gentle.”
We finish the rest of our food and drinks, and even have some desert. We finish our stimulating conversation about our work and hobbies, as well as other random assorted topics, such as gripes about mass transit. Both of us decide to go to a nearby bar for some more drinks, and to spend more time together. Neither one of us drink much, but nursing one or two drinks over the course of hours with food is fine. I am content nursing some general beer, such as Rolling Rock (TM), while you prefer a martini. I decide to introduce you to a bar which also specializes in arcade games that I went to once for a friend’s birthday party that I really enjoyed. You agree and after spending a few moments on your iPhone for directions, we walk several blocks to get there. We are so engrossed in our conversation that I barely notice you wrap your arm around mine and hold my hand.
When I do notice this, though, a tingling sensation rolls up my limb. I’ve never experienced this before, but I know I like it. The warmth and closeness to you makes me feel a happiness which I can’t quite explain. It increases the pressure to not mess this up, and I am trying not to showcase how giddy I am too much, since I always try to be aloof and cooler than I really am. Once at the bar, we both walk together with our drinks and examine the selection of arcade classics. Neither one of us are hardcore gamers, but both of us remember these quarter-eaters from our youth. I introduce you to three of my favorites from this location: X-Men Arcade, TMNT Arcade, and the rare Konami gem, The Simpsons Arcade. X-Men, in particular, I played a lot during my wasted youth in the 90’s and I know inside and out, which slightly impresses you. You enjoy some of the shooters, as well as Rampage and Street Fighter II. We spend a few hours there and many quarters, and we are both buzzing with shared proximity and nostalgia when we hit the street again. By now it is later in the night and the city is glistening with its lights.
“How was that?” I ask.
“Fun. A little geeky but I like that,” you answer back. “Hey, it’s getting late. Do you want to, um…”
“Uh, hang out more?” I smile and try not to show my anxiety. “Right?”
“Yes,” you answer confidently. “My place isn’t very far. I’m trusting you not to be an serial killer, okay?”
“This has already been the best first date of my life, so there’s no pressure. We can wait until another date or two for that if you’re more comfortable,” I offer. After all, I’ve waited over three and a half decades for this moment; another few dates or even a month or two is nothing more than an interlude.
“That’s sweet, I appreciate your disclaimer!” You chuckle, before patting me on the shoulder and winking. “But this is my dream date too, remember?”
“Of course. No pressure, right?” I smile a little awkwardly.
You continue to snuggle up against my arm and draw my face to yours. “None. C’mere.”
“Oh!” I gasp, as our lips draw closer.
The sensation of our lips connecting is another new one for me. It’s a first kiss so I keep things simple. I try to match your movements with my mouth, and share your embrace. For a moment I forget how I hated public displays of affection when friends or other people did them. Turns out it wasn’t just me be shy and was all about me being envious. Who knew? Me, deep down. I cup my hands on your cheeks as we kiss again, our noses side by side against each other. It feels so natural despite my eyes being closed for half of it. I can feel my own heartbeat increase and I actually think yours does, too. An actual woman feeling passionate about me for a moment? I never thought this was possible.
When our lips finally part, I have no idea how many minutes it’s been. We each take a moment to catch our breath, as your face is still cupped by my hands, and you stroke my hair a bit.
“I think we really need to get to my apartment,” you say in a soft and hurried tone.
“Yeah,” is all I can say as we walk, fast enough for it to be a near jog, down three avenue blocks and about four short short blocks to your apartment. Our hands are interlocked the entire time.
As an editor for a major book publisher, you actually earn a higher salary than I do. While hardly rich, it does mean that you live in an apartment building which is far more upscale than mine, with a doorman. However, you lead me to a back entrance that you also have the key for, which is a service entrance.
“I don’t need any side eye from the night watchman,” you tease.
It leads me to believe I am hardly your first one date conquest, and perhaps not the last. This hardly relieves my inner anxiety, but it helps me understand how you have been so quick to all this. You will know your body and best advise me on how to please it. We all but scamper to the elevator, which is empty as this is the ground floor and it is late at night. You hit the button to your floor as instinct before I even notice the doors closing, and then you are upon me for another embrace. This time our kiss is more exploratory; I feel your tongue touching my lips and while this does feel strange, I also know to reciprocate (or to at least try to). As always, my golden rule is to err on the side of gentle. We caress each other’s faces as the elevator moves, and my head bumps the wall of the car enough to make a sound.
You chuckle. “Sorry, you okay?”
I chuckle back. “S’okay, it’s good to know I’m not dreaming.”
“No, just typing,” you tease, as if the fourth wall were merely your plaything.
The elevator finally reaches your floor and we walk together to your front door. You have a keychain that features an exaggerated rendition of Luna the cat from Sailor Moon, which jiggles as you turn the key. Your apartment is cozy without being small; a large couch in the living room, a modest kitchen, and a fairly large “master bedroom.” The walls are painted a dark shade of purple with much of the furniture being leather bound. Several posters of rock bands and some films are in the bedroom.
“Nice place,” I comment. “Though if I’m honest I wouldn’t care if you lived in Scooby’s doghouse at this point. I mean, he even had a wine cellar somehow.”
“Dork,” you tease as you push on my chest with your finger to lead me to the bedroom. “We’ve both been out for hours, we need a quick shower. You first and then you’ll wait for me. Don’t take too long, stud.”
“Yes, ma’am,” I find myself saying automatically, a leftover from my call center job when I am not thinking clearly.
It feels bewildering, showering in another person’s apartment. But in the end, a shower is a shower and shampoo is the same even if it’s a different brand. I still make sure to lock the door behind me, perhaps as a leftover from seeing the film “PSYCHO” at a young age. I give myself a complete scrubbing, taking roughly 15-20 minutes. Out of instinct I partially redress, only without my shoes or putting my jacket back on. I had hoped the shower would calm my nerves, but it doesn’t. I step out of the bathroom and you are there with your towel and robe folded in your hands to jump in after me, giving me a quick peck on the cheek as we pass. Your room is darkened, but lit with a lava lamp and a scented candle. As you shower, I cannot help but pace across the floor for several minutes.
Do I tell you my secret? Even if you already know, is that a conversation I want to have on a dream date? How about my fetish? Is that also something I want to get into so soon? It is all happening so fast that my head is swimming. It is everything I wanted so far, and within a few moments my secret will be moot. I need to try to relax, and–
That is when I see a pair of eyes peeking at me from the doorway. They belong to a housecat; with black and white fur. You hadn’t told me about a pet, and I’d neglected to ask. I theorize that the feline had been in another room which I hadn’t visited yet, such as the kitchen (where the food likely is). Or, the cat had been elsewhere, perhaps under or beside the couch. At any rate, even though I haven’t owned a cat since childhood, I know how to greet one. I lower my palm to the feline’s eye level and make a motioning gesture with my fingers. It works most of the time and sure enough, the cat comes walking over and gives my fingers a good sniff. It begins to rub its face against my palm for a few passes and offers a soft “meow” up at me. I offer a pet across the lower neck and back. It turns out the feline is friendly and quickly bounds beside me on the bed for more.
After a few minutes I hear your voice in the room again. “I see you found Smithers. Or he found you. I wasn’t sure about saying anything because a lot of guys I bring here don’t like cats.”
“I love cats,” I reply as I turn back to you, clad in only a robe which is barely closed. “There’s a joke about a pussy and me playing with it that I could make, but I won’t.”
“I think you just did,” you say as you slink closer.
“Smithers,” I say, once again falling on a reference. “After Veronica’s butler from Archie?”
“You don’t miss anything, do you?” You chuckle. “Good. I like a man with attention to detail.”
A pause, as you play with the collar of your robe.
“So, are we going to undress, or do we need to play some strip poker?” you ask gleefully.
“We’d better undress. I can barely play blackjack, much less poker,” I answer as is hesitate before pulling my shirt over my head.
I’ve never disrobed in front of anyone, at least not since I was a child. I only see the flaws about my own body, especially my torso, back, and stomach. I remain silent, not wanting to ruin the moment with my own anxiety.
“Hey, it’s okay,” you say as you toss your robe on the bed, which also causes Smithers to jump away. “See, I’m not exactly an American Gladiator either.”
“Nice reference,” I say with a smirk; nothing calms me more than geek stuff. “You’re beautiful, though. I’m–“
You place a finger over my lips as you crawl onto the bed. “We’re here, no more self doubt, huh? Guys who obsess over their own bodies neglect mine a lot. Just go with the flow.”
“Right.” As you proceed to kiss me again, I undo my pants. A part of me regrets wearing them now, since it’s hard to concentrate on doing both at once. I wonder how musicians handle it so easily? Hell, many of them do that in a moving vehicle, to boot!
I ask if you want a back massage, and you agree. Now this is something I have done, albeit not with a stranger. Again adhering to err on the side of gentleness, Your back feels smooth as silk, and it is amazing to even touch another woman here. Every positive sound and motion you make fills my soul with anticipation. You reciprocate, and comment on how “stiff” I am. I am not sure if you mean my back or somewhere else, and I don’t care. You are the one who starts to shift your caressing to below my waist, and I get nervous for a moment. You ask if it is okay and I nod, asking if I may touch you as well.
I decide not to tell you of my virginity, or of my fetish. I am anxious enough and I just want to enjoy the experience and do as well as I can with it. This is my first time and I want to explore. I gently go from kissing you on the lips before moving onto your lips. I gently caress your breasts, gently and softly, treating them as delicate pleasure zones. I move my fingers down the sides of your torso, and am simply enjoying the sensation of touching a woman. You tell me that I am going to drive you crazy if I don’t start going somewhere lower. This is my first time seeing a vagina in real life and while I have certainly seen pictures and diagrams, they do not compare. My heart is beating so quickly with anticipation and excitement mixed with fear that I worry about vibrating through the floor. So with no other options or experience I resort to asking a question. As always, I try to use humor as a mixer, but I do not know if it will work.
“This is sex by numbers and I’m the brush; just show me the numbers, baby,” is the best I can do on such notice.
Its lame; bad porn writing. It’s the biggest moment of my life and that’s the best I can do. But this is a dream date, so it’s good enough for you and you begin to guide my hands. Once again, I begin with soft and gentle strokes, as if caressing a flower. When you want it firmer and harder, I do so. I do my best to not go too firm too soon with my hands. By now, my own genitals are throbbing, but I am not in a rush. My orgasm is pretty much guaranteed; I’ve made myself cum rubbing off against furniture or the side of my own leg. I did not wait over thirty years to rush things now. In fact, if I could relive one moment endlessly for the rest of my life, it may be this one, or this date.
In time you become wet, and then I ask if you are ready or if you want more. After some more caressing of your sides, you nod and motion for me to initiate. I fumble for the condom I would have brought, as I always do for every first date. I try to open the thing and roll it on as fast as I can; I am thankfully I did not have to undo a bra tonight. After so much anticipation, it feels as if my manhood is about to fly through the roof, much less enter such a wonderful woman. Once more, I begin gently, only increasing pressure when guided too. By now I have confidence to ask, if only in one word questions.
It is nothing like masturbation, and not because of the physical sensation itself. The evening leading up to it, the conversation, the laughter, and the pure happiness…there is no self session which can match that. Your body is a living pleasure zone and I practically want to touch every inch of it. It feels so warm, but not uncomfortably so. And after it is finished, if you are up for it, I return to caressing your body where you want it. I have never tested my erections for distance but I know I can return to rigidity with some more stimulation, and your entire being is stimulating. Time blurs. The clock does not exist. I may forget my own name at some point. None of that matters. What matters is the two of us in this bed, having sexual fun until we both are about ready to pass out from pure sexual ecstasy.
Even when it is over, I want to be close and together with you as we sleep together — actual sleep. My last thoughts are that this is all I have ever wanted since I was about 16 or 17 years old, and that after so long I have finally achieved it. I am no longer a virgin, and no longer the Dateless-Man. In fact I don’t know what I am now. And while there may likely be a twinge of regret for not getting there sooner, I am satisfied that I got there with you, in this way, tonight.
And I hope to take this journey with you again another evening, and an evening after that, as we continue exploring what our lives are like together. At least for a little while, so long as we are both happy together.
I try not to think about Smithers watching the entire thing.
So, that’s it. A completely fictional, mildly erotic and completely amateurish account of what I would like my first romantic experience to be, under completely ideal and optimal circumstances (not realistic circumstances). There is a bit of a bittersweet taste to it, as I suspect I may never experience anything close to this. It is a pandemic era, I am fighting an eviction, and age is against me. And considering all that, there are worse things than never having sex. Being homeless or either dead or disabled from Covid-19, or heck, a speeding car, are worse.
But a fantasy has to start somewhere, so this is it. I want to meet someone wonderful, who is at least half as into me as I am into her, and I get her off as she gets me off. That’s it. I don’t need the moon. I never did. Am I really asking for so much? Is it really so difficult? It has for me. The perfect set of circumstances has never fallen into place to make the above anything less than a lonely man’s fantasy.
It’s not a bad fantasy, though.
For another month, I remain the Dateless-Man. Thanks for reading.