Your First Pegging

You breathe deeply as you stare into the bathroom mirror, trying to ease the tension in your chest. “In and out, it’s going to be fine”, you tell yourself. This is what you’ve wanted for so long, and it’s finally happening. You lean over the sink and splash some water on your face, rubbing your fingers through your hair as you stand. She’s waiting on you. With one last deep breath, you reach for the door handle.

As you walk out, you see she is sitting on the edge of the bed with her legs crossed while absentmindedly smoothing the comforter with her hand. When she hears you her eyes slowly move towards you. Cracking a smile she says, “Took you long enough.” And pats the space next to her on the bed. Like a puppy, you scamper over and sit next to her.

“How do you feel?”
“Nervous, but excited Miss.”
“That’s to be expected,” she says softly and she runs her fingers through your hair. “A boy’s first pegging can be intimidating, but I promise I make it fun.”

You love the touch of her hand in your hair, even more as she brings it down to caress your face. Slowly, she traces down your neck with the nail of her index finger down your chest. She grabs one of your nipples and pinches it, hard.

“Tell me what you are,” she says with her ever typical sultry voice.
“Your slut, Miss.”
“That’s right,” she reaches for the twitchy mound growing in your pants. “And what’s this?”
“Your cock, Miss. “
“Mhmmm, yes it is. Good slut.”

She stands up and unties her dress at the waist. The black fabric unfolds and reveals matching black lingerie underneath. It doesn’t matter how many times you’ve seen her naked, each time feels like the first. You feel a twitch in your cock as she tosses the dress aside, and picks up the harness. You drop to your knees in front of her when she hands it to you, for your know without a word what she wants you to do. You hold the harness as she steps into it, then slide it up her calves, then thighs, up to her hips. You can smell her pussy now, and your mouth instinctively waters. She tightens the straps as you lay your forehead on her lower stomach, breathing her in.

“Get undressed.”
“Yes Miss.”

You quickly take off your clothes. Standing in the middle of the room, you feel her eyes inspect you as she walks around you. It feels like your breathing is too loud, or the room is too quiet. You hear her pick something off the dresser. Then you feel it, the leather end of the crop dancing lightly over the back of your knees up to your ass as she traces your body with her favorite implement.

You know what comes next and instinctively lean forward to brace the bed. She begins. And she doesn’t go easy. The thwacks on your ass sting, and you grow even harder. She pauses and adjusts the crop in her hand. Using her full force, she makes impact with the body rather than the end of it as if it were a cane. The sight of your marked ass excites her. Your breathing becomes heavier, and you moan as you hear her begin to laugh. She wraps one arm around you and grabs your cock, and whispers in your ear.

“My good slut. Now lay in the bed.”

Another moan escapes your lips as she squeezes yourher cock before letting you get onto the bed. You are on all fours ready for her. She positions herself behind you, rubbing her hands over your ass. Then traces the marks she made with her nails. She then leans forward and kisses one particularly painful mark before biting it. She uses her tongue to clean up the blood she drew with her teeth.

She separates the cheeks of your ass and slowly inserts a finger. “Fuck,” you moan. She removes her finger and replaces it with her tongue. Slowly she licks your asshole as she starts to play with your balls. You start to lose yourself a little, the moans escape more and more as she consumes you.

“Lay on your back slut.”

You roll over quickly onto your back. Her brown eyes stare directly into yours, while her mouth has a soft smile. She reaches over your head for the restraints attached to the bed frame, then secures each wrist in a cuff. She spreads your legs, and places a pillow under your ass to angle it towards her. Slowly she slides her strap on in. Her eyes making contact with yours every inch she goes deeper.

It feels familiar from the anal plugs she had you use to train your ass, but not the same. She’s filling you, deep inside. It’s so much more and you’re floating as she begins to slowly thrust her hips. Her right hand slides up your chest and pinches your nipple. She smiles and laughs when you flinch. She tugs on it harder as she thrusts harder inside you.

Moans escape you completely uninhibited now as she fucks you. She begins to thrust faster, causing you to pull on the restraints instinctively. Everything is throbbing. You’ve never felt ecstasy like this before. All you can think about is cumming as you ride the edge. Seeing your enjoyment and hearing your moans causes her smile to grow and she fucks you harder. You’re getting close, you won’t be able to take much more.

“May I cum, Miss?” you manage to say in between moans.
“No slut.”

Her hips thrust faster for a moment of torture as you try to deny release. Your moans become louder the closer you are to cumming, and then she abruptly stops. Her laugh is borderline maniacal as you whimper. You wonder if she will even let you cum at all tonight. She’s denied you much longer before.

You feel her renter you again, but this time not so slowly. Her eyes flash as they look into yours and she laughs as you begin to moan again. Having already been on edge, you know you can’t last long. Her strokes take over your body as you begin to float again. You feel the build peaking again, but so much stronger this time.

“May I cum, Miss?” you manage to say in between moans.
“Yes slut.”

She uses her hand to help you release while still thrusting. She makes sure every last drop of cum is extracted before she gives you peace. And then, it’s done. You catch your breath as she cleans you up and uncuffs you, soaking in the high of your first pegging.