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Micky’s Awakening Part 1

"A pegging and cross-dressing fantasy story."

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I have been writing erotica as a way to explore the rabbit holes that my mind goes down. I’ve decided to share this one here to see what you think.

The combination of nervousness and excitement race through me as I decide what lingerie to wear. I decide on a sky blue lace babydoll dress chemise with a matching thong, my favorite. I pair it with a white choker collar, and then sit patiently, but nervously on the bed as you prepare in the other room. I’m nervous because it’s my first time dressing in lingerie with someone else.

You come in and my jaw drops as you look absolutely stunning in your black three-piece lace lingerie with stockings and heels. You smile when you see my reaction, but then turn your attention to me and my outfit.

“Ohh, look at you! Stand up so I can get a good look at you.”

I do as requested, but I get embarrassed and look at the floor, blushing. I hear you walk in front of me, and you gently place your hand under my chin and raise my head up.

“Don’t be embarrassed, Slut. There’s nothing to be ashamed of. If you feel good doing this then allow yourself to enjoy it. Understood?”

I nod my head. “Yes, Miss.”

We both turn my attention back to you and your outfit. You say that it’s time for me to properly worship you. You sit on the bed and I get on my knees before and begin to give your feet and legs a massage with both my hands and my mouth, gently rubbing and kissing each part. Slowly I work my way up and down each of your legs.

You give me a confident and affirmative smile as you watch me. In turn, as I kneel before you in between your legs, I feel a sense of comfort and peace as if I’m in a safe space, I’m where I’m supposed to be.

I notice you start messing with a bag you brought with you, when you pull a large dildo and harness from it. You giggle when you see my surprised response.

“What do you think of my girl cock, Slut?”

“It’s huge Miss,” I say nervously.

You let out another giggle, “I think you were meant to take it, Sissy. Here help me put it on.”

With that you stand up and I help you into the harness, my eyes fixated on the dildo as I do.

You then turn to face me, your dildo hitting the side of my face as you do. You let out a fake surprised reaction as if you didn’t know that would happen.

“Well, you, look at that! Your face and my girl cock have met. Now Slut, I know you sometimes imagine yourself as the woman in the porn you watch. Well, what’s the first thing they do before they get fucked?”

“They suck it, Miss.”

“Very good. Now it’s your turn. Your going to be my cockslut, so suck my girl cock, slut.”

I proceed to lick and kiss, and then suck the dildo, struggling to fit it into my mouth. Slowly I start to move my head up and down until I am full fledged giving you a blowjob.

I feel your hands on the back of my head and then feel your hips start to thrust, gently at first, but with increasing speed and intensity. My hands grip your legs for support as I concentrate on keeping my gag reflex down, as a mixture of saliva, tears, and different noises escape my body.

We repeat the process multiple times; each time it seems like I’m able to take the dildo further and further. Finally, I feel my nose pressing against the fabric of the harness, a signal to both of us that the dildo is fully in my mouth and throat. Your hands and hips hold it there like a vice surrounding my head. You take one hand and move it to my throat, rubbing it up and down. You comment with glee that you can feel your girl cock in my throat.

After what feels like an eternity but in reality has only been a few seconds, you withdraw the dildo entirely from my mouth. A long stream of saliva chases after it before falling on my chin and chest. As I gasp to catch my breath, you giggle and comment how cute and slutty my rosy-red cheeks look shining with saliva.

You help me to my feet and we kiss, before you instruct me to stand with my hands on my knees, bent over slightly. As you walk behind me you say it’s time to loosen me up. I feel a new sense of vulnerability as you lift the lingerie up, exposing my ass (and the thong) to you. I feel your hand begin to rub my ass cheeks as you comment on what a cute ass I have. I then feel it temporarily depart my ass before I am quickly met with a stinging sensation and the sound of your hand smacking my ass. You repeat the process, not brutally hard, but enough to turn them red and warm.

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I feel that warmth when you tell me to take my hands from my knees and spread my cheeks apart. I then hear the sound of the cap on the bottle of lube opening, and a new round of nervousness hits me. Sensing my nerves, you rub my back and tell me to relax, that you’re only using your fingers right now to loosen me up. I then feel your hand rubbing lube up and down my crack, before you press a finger in me, causing a soft moan to escape my lips.

Slowly your finger begins its solo exploration of my ass, moving in and out, and around. Then a second finger joins the first one, and I can feel myself relaxing more and more. Confident in your prep work, I feel your fingers retreat before giving me one more smack on the ass.

You instruct me to lie on the edge of the bed on my back, so that we can see each other’s facial expressions as you enter me for the first time. Holding my legs up, I feel the dildo pressing against my hole as you apply lube to it. The nervousness shows through my face.

Reassuringly you tell me to relax and to exhale. With that you begin to slow press the dildo forward as it enters me. My ass tries to resist the invader until finally I feel a popping sensation, as my sphincter submits and the dildo continues its slow plunge into me.

I’ve used toys on myself, but this is the first time that I’m not controlling the movement as it stretches me wider and wider until finally I feel your hips press against cheeks.

My body is tense as I have never felt fuller, my brain trying to comprehend the pain and discomfort messages. You bend over and kiss me, letting me get accustomed to the dildo in me. Releasing our kiss, you whisper, “Ready?” with an evil smirk on your face.

I nod, and with that you begin to slowly withdraw the dildo until just the tip remains and then slowly plunge it fully back into me. Again I wince in pain. You repeat the process, each time picking up speed and intensity, until you’re thrusting in and out of me at a high speed. You tell me to pull my knees up higher. The initial pain still remains, but there’s a new sensation of pleasure building in me, leaving me the only option of moaning like a girl getting her ass fucked hard with each thrust.

It’s a mix of emotions that are racing through my mind, ranging from humiliation at first to exhilaration and excitement as you pound into me.

Then you pull out of me, leaving me feeling empty and wanting more. You instruct me to roll over and get on all fours, which I quickly do. The moments that it takes you to climb onto the bed feel like forever, and I feel the most vulnerable I’ve ever felt as I wait for you to re-enter me.

I feel you get behind me and lift the lingerie, exposing my ass to you again, and again my feeling of vulnerability returns. But something else returns, the yearning for you to return the dildo to my hole and resume fucking me.

You then spank each cheek a few times, causing me to yelp. You then spread both cheeks.

“Aww, look at it gape. Reach behind you and pull your cheeks apart, sissy. Present your ass to me."

I then feel the dildo press against it.

“Whose ass is this though?” you ask.

“Yours, Miss.”

“And what do I get to do to it?”

“Whatever you want, Miss.”

With that you plunge the dildo back into me, quicker and more forcefully than before. There’s no warmup this time as you fuck me hard. I feel your hands gripping and pulling my ass for leverage. Then they begin to race between gripping my ass, spanking it, and scratching my back. Meanwhile you begin to call me every name you can think of. "You're such a slut. You're my bitch now!”

My only responses to the onslaught are the grunts, moans, and screams that escape my mouth as my mind races to comprehend the flood of sensations it’s feeling. Eventually the pain, although ever present, starts to be mixed with more and more pleasure. In time I feel myself getting closer and closer to an edge I haven’t experienced before. Suddenly a flood of emotions crashes over me and I cry out in my first anal orgasm.

You drive my body into the bed as you collapse on top of me in your own orgasm, our bodies trembling and panting together, overcome with the emotions coursing through us.

Slowly you remove the strap-on and roll me over as we embrace in a kiss. Breaking the kiss, I whisper the only thing that comes to mind: “I’m yours, Miss.”

Published 
Written by mickyboy213
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