I'd become meaner and meaner to my girlfriend, Dilanna. It wasn't even her fault, but it started with something she told me.
Dilanna wasn't my first girlfriend; she's my second, and aside from knowing neither of us is an untouched virgin, we'd avoided talking about our pasts. That was my idea, actually. I told her early on, something like let's not worry about that. I meant it, I didn't want to explain my failed relationship, and I wasn't curious to know about hers either, if she would rather not share anyway. I still believe it's important to allow for new beginnings with new people untethered by painful memories.
We'd been together for about 13 months when Dilanna and I were at her apartment watching a raunchy comedy after fucking through the beginning earlier. She was sitting on her laptop working on stuff for her university courses, and I was lying back on her bed nude. There was a scene in the movie when a woman, distracted by her phone, stumbles into the wrong side of the gymnasium, into the men's locker room, and walks in on this pro-athlete dude while he's taking a shower and sees that he's beyond packing. The movie even shows the jock's slick six-pack and then pans down for a shot of his massive donkey dong for like 4 seconds, beads of shower water dripping off it. In the next scene, the woman character is whispering in giddy shock about what she witnessed to her girlfriends, raving about this guy's pendulous appendage. I looked over to see that my girlfriend had stopped typing and working; she was watching with a big grin. She briefly turned to me, her cheeks pink, with a snicker and returned to working, tap tap tap.
"That's fake." I blurted.
My girlfriend looked to me, smiling, pressing her lips together not to say anything, and shrugged.
I wish I had left it alone. Instead, I said, "Do you agree with her?"
Dilanna turned to face me again, still smiling, "Agree with her about what?"
"His cock is mag-nif-i-cent?" I imitated the female character's enthusiastic enunciation.
She shrugged, "It is a nice one."
Indignant, "Hanging down to his knee is nice?"
She cocked an eyebrow like that should be obvious, "Yeah? He's got a big dick; it's hot. That's the joke."
My tone turned accusatory, "You like it like... that big. You would go for that?"
Now she sat straight and turned to face me properly, "Well... I have. But I wouldn't now when I have you."
My gut sank. "What do you mean you have?"
She smirked, squinted, as if she didn't understand me or my problem, "Ian, before we met, I was sexual. I don't just hold hands and kiss, I like dick." She shrugged.
At this point, I could have stopped and probably have been OK, but I needed a reassurance I wouldn't get, "You like big dick."
She shrugged again, "I mean... yeah." She was catching on now that this wasn't a her problem but a me problem, and she did her best to save the conversation, or to save me from this conversation, and in a stroke of genius she said exactly what I needed to hear, "Ian, you're big. Your dick is big. You're in the big boys club." but she tucked her hair behind her ear. I took that for a tell of insincerity, a white lie.
And like a fool, I threw it back at her, "Come on, I'm not big like that." I opened my hand at the TV, the prize cock character was on screen, though clothed, getting awkward and intense cheesy attention from all the lady characters who'd gotten gossip about his endowment.
Dilanna did this nodding headshake, "OK."
There was an awkward pause, and then I asked what I had to ask, "You... um... saw one like that."
She laced her fingers together, submitting politely to my little interrogation, "Not that big, Ian."
I nodded, raised my eyebrows, nodded, "But bigger than mine?"
She nodded with me, "Sure."
I know it's dumb, right? But in the moment, it doesn't feel dumb. I just felt so... emasculated. "Alright. Good to know." I sighed.
And then she made it immeasurably worse, "Ian, baby, a relationship isn't all about body parts or great sex."
I hadn't made the connection between penis size and sex quality. Offhandedly, she did. She might as well have thrown a dagger into my groin.
"Oh? Not about great sex?" I stood and grabbed up my clothes, put them on, and didn't speak. "Not a relationship with me."
She closed her laptop, "Hey, don't be like that. It's such a stupid thing to have that kind of reaction to."
My head popped through my t-shirt collar, "Don't tell me how to react."
And I left. I really had shit to do, thank God.
She texted, trying to make light of it, joking, and rubbing my ego. Things like "I said you're big, I'm being honest," and "I'm going to choke on it when you're ready," and "You're too big to give off small D energy, it doesn't suit you," and so on.
And then we just didn't talk about it. Time went by, I guess like 3 weeks. Under the rug that episode was swept. But I kept thinking, and thinking, and thinking. I couldn't stop thinking about it, at work, driving, eating, with my friends, in my classes, there was only replaying in my brain her face, her voice, her reaction, her attempt to walk it back and soothe my jealousy or diminishment, and that giant cock on the screen, and those stupid-stupid women adoring it, and the imprint in my memory of Dilanna adoring it too, her big smile, gushing over another man's giant cock!
Dilanna would ask me if I wanted her to make me a snack, and I cut her off, "No."
She might ask if I wanted to go for a walk, "No."
She'd ask how something in my life was, family or a friend, "Fine."
She didn't understand why I was treating her like this, but I had come to see her like she had cut off my dick.
From then on, sex with Dilanna sucked. Not for lack of effort on her part, but because I was not mentally there. In one instance, she initiated, and I couldn't get hard. The more attention she tried to give it then, the more flaccid I got. It was the first time a woman had sucked my wiener that it just rolled around in her mouth all soft. Another time, I was initially into it, as I had been in a great mood all day, but halfway into fucking her, I watched my cock pounding into her pussy, and it occurred to me how much smaller mine must be compared to what's been in that very same orifice. Inside her, I became weak and floppy as a cold stick of string cheese and couldn't finish. It slipped out from pure shrinkage, a retreat. She asked me what was wrong, and I brushed her off with no clear answer.
Then, yet another time, I consciously tried to reframe it to myself that I should step up to the challenge. Fine! If the other boyfriend had more meat, I would put in more fuck. It's not the size of the dog in the fight but the size of the fight in the dog, I told myself. I was able to perform with this motivational mind trick I played on myself, but it also made me hyperaware of her response. I checked Dilanna's face, her voice, and her posture for signs she was loving it, that she was getting serious pleasure. That backfired; I simply didn't hear or see what I was diagnosing for: the hot moans, the eyes rolling white, the writhing, the spasming, nothing. And then she scratched an itch on her nose like one might do when they're having an empty-headed cigarette break in the parking lot. I was done. No nut. I pulled out and got dressed. She sighed in frustration, "Ian, what is it?"
I grumbled and went for a drive.
Dilanna did what she could to bond with me; she praised me for all my many good qualities: funny, clean, considerate, handsome, fit, musically talented, attentive, gentle, interesting, interested, cuddly, good-smelling, whatever. She said nobody understood her as I did. She said I'm the first man she imagines having a life with, with a tear forming before she wiped it away on the back of her wrist.
Fuck all of that. I don't want to be her Mister Perfect all-around man; I want to be her greatest fuck. Maybe she's fine with having checked off the get stuffed by a giant cock box, and now she can settle with a safe, stable, better personality match who gives satisfactory OK dick... but I'm not fine with that.
Dilanna came over to my place, skipping one of her classes. She sat beside me on my bed, took a big deep breath, and said, "I know what the problem is. I need you to get over it."
"You know what my problem is? Tell me." I muted the TV.
"I was careless with my words and my reaction. But I'm not going to apologize too much because I didn't do anything wrong beyond that." Dilanna said in a reasonable voice.
"I didn't say you did anything wrong," I said in my reasonable voice.
"But you're treating me like I did. It was before we met," she took hold of my hand.
"I get that." I nodded.
"Then let it go," she squeezed.
I didn't know how to, "No."
"Why not?" she scooched closer.
"I don't know. I hate it." I said, and we sat quietly.
Dilanna and I started making out. She got my pants off, and then, whispering as she gave me a hand job, "Ask me anything, get it off your chest. I'll tell you everything you want to know."
I was embarrassed to ask anything having to do with it, but her invitation gave me permission, so I asked.
"How much?" I could barely say it.
Stroking my dick and looking me eye-to-eye, she whispered, "How much what, baby?"

I swallowed, cleared my throat, "How much bigger?"
Her eyes widened, she stopped stroking, her mouth popped open, "Huh? Oh."
Leaning back, she positioned herself to really look at my privates. She eyed them for a moment, and the feeling of having her inspect me with such intent sent my member inflating to its max. It bobbed and bobbed as she leaned in for a closer look.
With me lying back pantsless, she held my erection upright and vertical. Then, with her opposite hand, she touched the tip of my dick with the tip of her index finger. Swallowing and eyeing it carefully, she raised her finger over my dick an inch, then higher until she stopped hovering above it with about two inches of clearance.
I had a vision then, looking at her beautiful face and shining, intense eyes, of her regarding that big cock when she saw it first. I could see it clearly as if it were there. I imagined what she must've felt when she first saw that enormous man meat, versus what she must've felt when she first saw my average-ish penis, and silently compared.
I couldn't breathe. And against myself, gritting my teeth, I spurt, and spurt, and spurt. It was all over her shirt, on her arms, on her wrist, running down over her knuckles, on my thigh.
I wanted to vomit. I felt the blood leave my face. I turned to roll off, but Dilanna threw herself over me, grabbing me by both wrists without care for the mess. "Stop. You like it!" She blushed and nuzzled her mouth into my neck, "You do!"
Thus began the second phase of my implosion. Our relationship improved, we were happily walking and holding hands again, going on fun dates, and I felt a weight removed, at least for a while.
Once Dilanna understood I was, reluctantly and against myself, getting off to this inferiority contrast, she dove into it. No more filter, no more polite comforting context or softening of cruel truth, she let me have it.
When fucking her, she volunteered, without my prompting her to, dirty talk like "It's sooo nice to be stretched, the more the better.... ooohhh!"
And I just lost any ability to keep from ejaculating when she said things like that.
Another time, when I was pounding her from behind, she reached a hand back, grabbed my ass cheek, and pulled me into her as tight as she could. With me pressed as tightly into her as possible, she moaned with need, "Deeper, only a little deeper!" as if I was almost long enough to hit the spot... but not. I would cum so hard hearing her say that it must have looked like a kind of seizure.
But the absolute killer was when I was in class, and I got a text from her. It was a link to an online sex store. The item, a kind of penis extender, like a realistic dildo, a guy wears over his own penis to fuck a woman with. Essentially a cock prosthetic. She had typed, "I want to get this for you, so you can see what I'm like when I get that complete fullness from a man. Oh my god, will you wear it for me?"
I texted her back, my hands shaking, "Isn't that too fat and long, though? Could it fit?"
I watched for her reply. Typing... typing... typing... and then, "But that's the size I wish you were. You would be so good in bed, then."
I couldn't leave class; instead, I sat deaf to anything the professor was blabbing about and sported an impossibly stiff erection through to dismissal. As soon as I could exit, I went straight down the hall for the public restroom and with 3 strokes let it fly in a stall.
Then happily ever after with Dilanna, right? Not a chance. The novelty of sexual humiliation is a potent kink, but when she became this woman who teases and debases me, she also exited from my vision of a forever woman, a wife, a soulmate.
You might say that a woman's best sexual partner and the love of her life need not be the same man, and it is rarely so. I know. Yet, it's not for me.
You might say dick mass isn't synonymous with female sexual satisfaction; the clit is on the outside, too big can hurt, it's how you use it. Technically true, and in sum, a bunch of feeble cope.
Did I love Dilanna? If I didn't, I wouldn't have felt this way about that. If I'm not the woman-I-love's best, biggest sexual experience, then who am I? Someone I don't want to be.
I broke up with Dilanna. It went smoother than I thought it would. I suspect she also lost some respect for me, or darker yet, maybe she was happy to be free to find heftier material. How silly would it be to break up with someone over cock size mind-fuckery? How silly would it be to lie to yourself that it was actually about "other stuff"? Yes, it's not like we broke up because we didn't share enough hobbies or our friends didn't sync or something. No. I was over feeling sexually small as a man, insufficient inches, the less than best, the fine-not-incredible. I don't want a woman who can compare my manhood to another unfavorably and make the decision to love me because I guess love is about who's attached to the dick, not whose dick bangs her pussy to hell and delivers her an orgasm like heaven.
I'm actually glad she told me when she did. If that dumb comedy scene hadn't flashed that thick donkey dick at us, I would have gone forward in our relationship ignorant of what she had... had. I would have been stupidly unaware of what my dick was to her in her experience, where it ranked. And then maybe it would have come out some other way, much later, after we were married and had a kid, and I would no longer have such a swift, uncomplicated exit as I do now. I might even have to just swallow it. Thank goodness I'm spared that.
My bind, having broken up with Dilanna, is that I still crave women. I still crave romance. I still want to do the dating-into-marriage script. But I'm afraid any woman I meet will be the same story rerun. What are my odds? Yes, I did research, in my many spirals, and found that one-in-two dicks are larger than mine. One-in-twenty dicks is much larger than mine. If a woman I meet has done the deed with even a handful of men before me, it's pretty well guaranteed I won't be her biggest, and in our sexually liberated age of high body counts, there are virtually no women after their freshman year of university who haven't gorged on a diverse buffet of various cocks.
It's enough to make me want to detach totally and have uncommitted sex without regard for any woman's past or future. But that's so bleak and against my values that I begin to think of becoming a celibate kind of monk.
Though I've mostly jacked off, I also messed around, just hook-ups. It was great to get some sex without the insecurity cramping the experience. None of those post-Dilanna girls mentioned hog dimensions, but if they had, I wouldn't care, because unlike with Dilanna, I wasn't invested in how these women judged me down there or anywhere. It was fun, I checked off some boxes on my bucket list: my first foreign girl (from Caracas), my first Goth (who was covered in black ink), and my first social media thirst model (gorgeous and vapid). I was able to pressure wash Dilanna off the concrete walls of my mind each time I made one of them cum.
Then I met a gorgeous redhead named Aisling. A dating app, standard, I know. But she wasn't standard. If men aren't created equal, neither are women. She had the tightest, sweetest, fiery cunt on this damned Earth. The difference between her hole and Dilanna's in snugness, grip, texture, and intensity of sensation was amazing, purely amazing. On driving my dick into this ginger, I had to press extra hard to get the last inch or so of my length into her to go fully balls deep. It almost felt like her pussy was swelling up and trying to spit my dick out, and couldn't. I found paradise between freckled legs. Firmly pressing my pubic pad into her clit, stirring my cock around, the ridges of her G-spot rubbing my dorsal shaft, I let it go into her, washing her cul-de-sac and cervix in my sperm.
But Ainsling was on a break from her cornfield town's longtime boyfriend, and when he came calling her to get back together, she lied to him that she hadn't seen anyone else since him and ran back into his arms. With a snatch like hers, and that hair, I would have taken her back if she had honked every clown in the circus.
Still, something in me wanted to tell Dilanna off. Yes, I know she had never explicitly belittled me. Just the opposite, she had tried to reassure me as soon as she could see how sideways I was taking her personal historical factoid. And a more mature version of me, that rational voice inside, said to get over it already, Dilanna didn't do anything wrong, and this whole fixation of mine is madness. Besides, there's nothing to prove.
Regardless, I hate it. When in the shower jizzing to the thought of her sighing in disappointment at my dick, I hate it. When I fuck any given woman and envision how much crazier she'd scream if she were getting railed with a true battering ram in place of my ordinary dicky, and I cum, I also hate it. When I think the woman I end up married to will be a craftier operator than Dilanna and never tell me she's had bigger, but she most certainly has, and that she sometimes misses that extra stretch and penetration, the length and girth, privately remembers her biggest cock with fondness and a wet pussy, wishing she could have it again as she takes my basic offering, I hate it. And I love it.
