The Making of a Sissy Part 1 [Cuckold’s Perspective]

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Continuing with stories about when Michelle’s friend Annie turned me into her submissive cuck. Go give that a read for context!

The next morning, I get a text from Annie. “Let’s go get lunch!” I agree and around lunch time she lets herself into my apartment. She walks in wearing a short little tennis skirt and tanktop with her hair in a ponytail. “I’ve gotta go by the mall, do you want to do that before or after we eat?”

“Whatever you want to do” I respond

“Let’s go after!” She says excitedly. So we head off for lunch at my favorite sandwich spot by our place. And when we sit down, she sits on the same side of the booth as me. She pulls her phone out and shows me a picture, “Here’s Shaun” she says. He’s a handsome black guy, short hair, nice beard, and he’s absolutely shredded. “Want to see his cock?” She whispers. I nod my head as she swipes one picture over. It’s a picture from above, his chiseled abs, defined V, and big black cock in hand. “It’s way bigger than yours.” She says with a laugh as she locks her phone and pops over to the other side of the booth.

The conversation goes normal for the rest of lunch, and when we finish she pops up and giddily says, “ok, time for the mall!” As we get there, she walks around stores for a while, never landing on something to buy. It felt just like everytime I go with Michelle. I was just her boyfriend begrudgingly following along at the mall. She never did buy anything and before I knew it we were walking into VS. She was walking through the store commenting on what she liked, but I was just on mall autopilot at this point. Mindlessly agreeing with whatever she said. She started grabbing panties she liked and we went to check out.

While waiting in line, she looks over at me on my phone. “Give me your card.” She says.

“Huh?” I put my phone down. “Why?” I ask

“Just give it to me.” She says sternly.

“Whatever” I say as I hand her my credit card. As the cashier starts to check her out, I notice a kind of funny look on her face but I ignore it and go back on my phone. The total was something like $90 which was annoying, but whatever, let’s go home.

As we walk out, she starts laughing. “Oh my god did you see her face??” She says

“Yeah what was that about?” I ask

“Oh my god, you have no idea do you?” She says as she’s still laughing. I look at her with a blank stare “these are for you dumbass!” She shakes the bright pink bag in my face.

Now that she says it… it all makes sense… I was too much on autopilot to even know what was going on, which she later admits was her plan all along and why she wanted to go after we eat. On the ride home, she starts pulling them all out and making me look at what I bought myself. “So…. Why?” I ask

“Cause Shaun said you’re gonna be his bitch, and bitches wear panties” she says as she laughs so hard she barely gets the words out. She composes herself, “and he wants to hangout again today. So you need to have panties on”

When we get back to the apartments, she walks right up to my door and unlocks it like it’s her own. She then walks right up to my room and lays out the panties on my bed. A wide variety of selections, colors, types, materials. She picks up a black lacey pair and throws them to me. “Try them on” she says with a giggle

I turn and walk towards the bathroom to change, “where do you think you’re going? Scared to change in front of me?” she teases as she sits on the edge of the bed, “go on, change”

So I pull my shorts and underwear down to my ankles, facing her. My t shirt hanging down to my small flaccid cock. “Awww, it’s so cute and small when it’s soft!!” She teases me as I go to slide the panties on. Now this wasn’t my first time in panties, but it was always a pair of Michelle’s. I was pleasantly surprised by how comfortable they were when they were in a size meant for me… I lift my shirt and give her a spin as I laugh.

“Oh wow, your butt actually looks so good!” She laughs as she leans forward and grabs a handful. “Now let’s go, we’re gonna go meet him and some friends at a bar near here!” I pull my shorts up and we head out the door, this was my first time ever wearing panties outside the bedroom… My heart racing as this was all moving so quick.

We get to the bar and head to the back patio, finding Shaun and four of his friends at a table. Introductions are made and when I shake his hand, I notice a slight grin. The kind of grin that says “hey bitch, I know you’re in panties right now”

There was a couple so Annie talked mostly to the other girl and I talked to the guys but everyone was cool, everything was normal. Shaun and his friends were all fun and it was just like if I was at the bar with friends of mine, drinks were flowing, people were laughing, it was great. After a few hours we close our tabs and head our seperate ways.

We get an uber home and the two of them were in the back with me in the front, they were whispering and giggling the whole ride home. We get out of the car and I open the door to the building, holding it open for them. I follow them up the stairs and follow them to Annie’s door. She opens it, we all walk inside and no more than 3 steps into her apartment, Shaun turns around and looks at me, “No more Mr. nice Guy.” He says as he looks at me with a straight face. He looks at Annie, she nods her head yes with a smile, he looks back at me. “How’d you like my cum last night you fucking loser?” He teases.

“It was great.” I said

He leans in and rips my shorts to the ground, exposing my panties. He laughs as he looks at Annie, “so he’s my bitch now huh?” She nods. He looks back at me, “I’ve always wanted to make a white boy my bitch… I want to hear you say it” he says.

“I’m your bitch now” I say with a straight face.

They both laugh as he places his big hands on my shoulders and forcefully pushes me to my knees. “Go on then, show me what you can do.” He says.

I reach up and slowly start to rub his cock over his shorts, feeling him slowly get hard before peeling his shorts and underwear off exposing his half erect cock. He steps back and turns, “crawl over to the couch bitch” he commands. I start to crawl on my hands and knees, and as I do, in one swift motion he leans in and spanks me hard on the ass. I fall forward a bit before gaining composure, “what’s wrong? Did that hurt?” He teases. Annie laughs

“No.” I respond as I continue to crawl, but he leans in and unleashes a hard spank on my other cheek.

“No, sir.” He demands.

I get to the couch and he walks in front of me, his cock fully erect now. He sets it down right across my face. His balls at my chin, and his big meaty cock covering my entire face. His cock and balls are smooth and hairless other than a small well groomed patch of pubes above his shaft…

He laughs as I instinctively take his balls in my mouth and grab hold of his cock with my hands and start to stroke. Then I put the tip of his dick in my mouth, as I look at him. He runs his fingers through my hair before grabbing the back of my head and forcing his cock down my throat. I barely get halfway down before gagging hard, spit falling everywhere as I pull back. He pushes me back down, gagging again about halfway and pulling back. Once more he pushes me back down before I gag violently, spit falling everywhere again. He laughs as I catch my breath, grabbing my face and holding it to where we lock eyes before he slaps my face and pushes me away.

“Annie, show him how it’s done” he says as he motions for her to come over. Annie quickly strips naked and gets down on her knees and takes him deep in her throat. Somehow making his big cock almost entirely disappear. She holds it as she cups his balls and starts to move up and down.

“Lay down.” He says to me, “get her nice and wet for me.” I do as I’m told and lay on the floor, Annie climbs on my face and continues giving him head. I can feel the spit leaking down onto my body, and the sound of her moans with a mouth full of cock are driving me crazy. A few minutes go by before Annie stands up off of me. “Go back to your room” he says as he points to the door. “You don’t get to watch tonight”

I stand and grab my clothes. I go to put my shorts on and he interrupts, “I didn’t say to put those on.” Annie laughs. I walk to the door, wearing only the panties… “better be quick!” He calls out as I hear them both laugh again.

My hearts racing as I open the door and pop out into the hallway, quickly rushing to my door and unlocking it. I’m rock hard… too bad I didn’t get to watch tonight. I change back into my normal underwear and shorts, laying in bed, expecting to hear them fucking. But I hear nothing…

After a while, I hear them talking and giggling in her room for what seems like a long time. Then, fianlly, just as the night before, I listen to them fuck. I hear her moans, the smacks of her ass, more moans, knocking against the wall, and eventually it’s silent. I hear her door open and close. And just as the night before, shortly after it happens again and my door opens and closes again. Annie walks in, climbing into bed with me, completely naked just like the night before. She faces me, as she runs her fingers through my hair. “You’re sure you’re okay with this?” She asks with a genuine look of concern.

“I promise you, I love this shit…” I respond watching as she immediately smiles…

“Good. Because I’m so turned on by this….” She moans out. “And Shaun is too…” she presses her thumb against my lips, pulling down on my lower lip as her hand rests against my cheek. I open my mouth and wrap my lips around her thumb, swirling my tongue around it.

She moans, “I can’t stop thinking about you on your knees for him….”

“Oh yeah why’s that?” I ask as I start to kiss down her naked body.

“You just looked so pathetic with his huge cock hanging over you…” she whispers as she runs her fingers through my hair again. “Tell me how his cum tastes”

I bury my face in her cum filled pussy, licking and kissing like my life depends on it. “Fuck… it’s so good Annie.” She holds my head down, pushing it hard into her pussy as she moans.

“Look at me” she whispers, I look up to see her holding her phone. “Tell Shaun you want his cum straight from the source cuck” she moans out as I don’t stop eating her pussy….

“Mmm Shaun, I want your cum straight from that big cock” I whisper into the camera. She laughs, “I told you!!!” She says before throwing down her phone.

I continue to lick her cummy pussy until I get every last drop, now focusing on teasing her clit with my tongue as I start to finger her soaking wet pussy. A few more minutes and her legs start to shake, “mmm fuck, I’m cumming!!” She moans out as she holds the back of my head up against her pussy, pushing into me with her body as she forces me down. She squirms as I continue to lick after she came, she pushes me back a bit. I climb back up to lay next to her, she moves over a bit and lays on her side facing me, taking her hand and running her fingers through my hair again. “You eat such good pussy” she whispers, still running her fingers through my hair. “Which is good” she grins as she reaches down, squeezing my cock, “cause you’re a bit lacking…”

She giggles as she gives me a quick kiss on the cheek before popping out of bed, “see you tomorrow cuckie!” She turns and heads out the door. I jerk off, cumming almost instantly just as the night before and pass out.


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