Chapter One: Your First Visit
You'd been thinking about it for a long time: going to a gloryhole. Sucking your first ever real life cock anonymously. You'd been watching sissy hypno for years now, you wanted so badly to taste a dick, to taste someone else's cum. But you were afraid. Afraid of being recognized if you downloaded grindr or some other hook up app. You were a fairly respected and well known professor at the local college, after all. If people found out you were a secret sissy... you didn't even want to think about it! So you consigned yourself to a life of secretly wearing a clitty cage or a buttplug under your boy clothes and only dressing up and playing with dildos at home.
But then you learned about a local gloryhole and everything changed! Finally, there was a way for you to get what you craved, without the same risk of exposure! The only person who would have to know was the guy at the front who ran the store that the gloryhole was in the back of. You had to request access from him. But you were fairly sure he was an out of towner who commuted in.
And so, one day, after gooning to sissy hypno at home, you finally decide to say fuck it and take the plunge! Quickly, before you lose your nerve, you hop in your car and drive out to the store, parking in a different store's parking lot in case anyone recognized your car. You flip your hoodie up and put on a baseball cap to further hide your identity and slip into the store.
"Evening," the man says cooly. You swallow your pride and, taking a deep breath in, whisper to him that you're here for the gloryhole. He smiles. "First time?" You nod shyly. "Don't worry, you'll love it" he reassures you, placing a hand on the small of your back as he leads you through a door at the back of the store.
"There are two stalls," he explains. "One marked 'hole' the other marked 'John.' Pick whichever you like based on what you want to do." He stands there, watching you, waiting for you to pick. Blushing, you start towards the one marked 'hole.' He smiles again. "Thought so!" he says with a chuckle.
"Since you're just dropping in, I can't guarantee when, if, or how many men will pop by to use the other stall. But... if you enjoy yourself, you can always call me in advance and I can... set things up so you don't have to wait and you can have as many men visit as you'd like" He passes you a discreet business card with nothing but a phone number on it. You take it an put it in your pocket.
"I hope you enjoy yourself..." he says with a wink, before returning to the main store as you step in to the 'hole' stall and lock the door behind you.
Your heart races as you strip down to just your panties and cage. You keep them on, wanting to feel like a true sissy while you suck your first cock. There's nowhere to sit in this stall, so you kneel on the ground, noticing how surprisingly clean the owner keeps the stall, given all you imagine goes on in here.
As you wait for a cock to appear, your imagination runs wild with the thoughts of what you're about to do: suck some anonymous dick at a gloryhole! You think to yourself about how much you love the concept of a gloryhole, of mutual anonymity. He won't know who you are and you won't know him. Just the mutual joy of being anonymous. No strings attached. Everything is simple. He wants his cock sucked and his cum swallowed and you want to be the one to do that! Then you'll both be on your way, never to know who the other was.
You kneel there waiting for a while, longer than you'd like to have been waiting, eager for dick.
Then it happens. Without warning, a real life cock pokes through the hole into your stall.
You suck your breath in as you look at it. It's thick and meaty looking, but still an approachable size for your first time. The man is circumcised, like you, and his red-purple cock head is leaking a dollop of precum.
You lick your lips and slide over to it, grabbing it gently by the base -- or at least, the closest to the base you can get with the wall in the way. You gasp as you hold another man's penis for the first time. It's warm and both soft and hard all at the same time. Slowly, you lower your lips to the tip and give it a kiss, tasting the salty precum waiting for you.
And from that very first taste, you were hooked.
You run your tongue all over the length of the man's shaft, tasting every inch of him. It was so much better than a dildo! While this was your first time sucking a real cock, you had lots and lots of practice with your dildo at home, so you start to bob your head on it and do all the techniques you learned from all those sissy hypno trainers. He's differently sized than your dildo, but you make the adjustment easily. You want him to cum so badly, you can't wait to taste it.
Your mind starts to wander as you slobber on this anonymous man's cock: This cock could belong to anyone. Maybe even someone you know! Maybe your neighbour? Maybe your coworker? Maybe your boss? Your clitty tingles as you think about the naughtiness of sucking off someone you know without either of you realizing. Or is it hotter if they're a total stranger? Someone you'll never meet but someone who you will forever know what their cock tastes like... what their cum tastes like... It turns you on just thinking about it. You feel more salty precum leak into your mouth and you eagerly swallow it down.
You suck this stranger's cock, tasting and savouring every inch of it. You never thought you would ever be on your knees, worshipping a stranger's dick, but here you are, doing exactly that. And you couldn't be happier.
You let it fill your mouth, gagging as it reached the back of your throat. You stroke it lovingly while you suck it, making your mystery man moan in the other stall. But you don't even register his moan. You're in your own little world. It's just you and this anonymous cock. You moan as you close your eyes and suck it.
You want to make this stranger cum. You want that so badly. You work for it, servicing him like a good little cock sucking sissy slut. His moans are more consistent now and they fill your ears, sounding like the sweetest music. Suddenly, you realize you want him to remember this. You're certain that you'll never forget it and you want him to never forget it as well. You want to please and impress this stranger. You want to be a good sissy for him.
You love having cock in your mouth. To suck. To slurp. To stroke. All for that tasty cum. You can't believe you waited this long to come here. You knew, even from this first one, that you would absolutely be back.
You keep working his dick, worshipping every inch of it, loving every second you spend with it in your mouth. You can taste more and more precum. You reach your other hand out and, without stopping your stroking or sucking, you try to reach through the hole a bit and massage his balls, encouraging them to give you your reward.