Sissy Stories

Tricked into Sissification

Written by sissy_whore4bbc on IG

It was a Saturday morning, when I got a text from my friend, Kelly, telling me to come over to her apartment to hang out with her, and her roommate, Lisa. Since I had nothing to do, and my roommate Brian wasn’t home, I said to myself ‘why not?’ I texted her back, and said I’d be there in a half-hour or so.

I put on a pair of shorts, and a tshirt, and headed to the subway to get to her apartment. After about 45 minutes, I pressed the buzzer, she let me know, and I headed to her apartment. I got there, and Kelly had her door open and greeted me with a big smile, “Hey Chris!” Kelly, was a very attractive girl. I’m 5’8″ and she was a little shorter than me, and was also thin with nice breasts. “What’s up Kelly?” I said, as I checked her out. She was wearing black shorts, and a green tank top, and had her brown hair up in a ponytail. “So what’s going on today?”

“Well….come in.”

I walked in and saw Lisa sitting on the couch, she smiled at me. Lisa was a little taller than me, but also very attractive. She was wearing a black mini skirt, and red tank top, and had her blonde hair down.

Kelly closed and locked the door behind me, and smiled. “We’re just bored today, and wanted to hang out. Neither one of us has plans until Jimmy comes over later to hang out with Lisa, and I might third-wheel them,” Kelly said with a laugh.

“Well, glad to be your cure of boredom,” I said. I went to go sit on the couch and noticed that there was a pile of clean laundry on it.

“Oh…sorry, just move that, and put it on my bed” Kelly said.

“Alright, no problem.” I picked up the pile and went to her room, and put it on her bed. As I was walking back, I noticed I dropped one of her bras. “Almost forgot this,” I laughed as I held up a lacey hot pink bra.

Kelly looked at me and laughed, “Just put it on my bed…unless you’re thinking of wearing it.”I looked at her and laughed, “Well, I don’t think it’s the right size for me.” Lisa looked at me, “We can make it the right size…go ahead, try it on, see what it’s like to wear one.”

Kelly smiled, “Do it!”

I looked at them, and saw they really wanted me to put it, “Ok…if that’s what you want.” I put my arms through it, and tried to attached the back, but couldn’t. “Let me help,” Kelly said, as she ran over to me and clasped the back, “Not bad, it fits, but you don’t have boobs to fill it out.”

“He should really have it under his shirt, to get the real effect of wearing one,” Lisa said while she laughed.

“YES!” Kelly shouted. “I don’t know about that…let me take it off, and maybe we can watch a movie or something,” I said. Lisa looked at me, “That’s not fun, let us dress you like a girl, that will be fun!.”

I hesitated, “Uhh, I don’t know…”

“Come on! Trust us! This will be fun! We won’t tell anyone!” Lisa said. Kelly smile at me, “If you let us do it, maybe I’ll give you a blowjob.”

I looked at her, and thought to myself that it has been a few months since I had a blowjob, and could really use one, especially from someone like Kelly. I nodded, “Ok, but as long as you promise to not tell anyone!” They both laughed, “Of course not,” Kelly said. She thought for a moment, “Now strip down naked.”

I did as she told, and she looked at me, “You’re doing to need to go into our bathroom and shave, everything! Girls aren’t hairy.”

“Umm, ok, if I need to,” I said, thinking to myself, ‘whatever it takes for a blowjob.’

I went into the bathroom, and filled up the bathtub with water, looked around, and find a few of their razors and shaving cream. I got into the tub and soaked for a while. I then lathered up my legs, and grabbed the razor. I hesitated for a second, but started to shave all the hair off. I made several strokes over the same spots to get it as smooth as possible. I then moved to my pubes, and butt. Then shaved my chest, and arms. My back took the longest, but after a while I was completely shaved, and smooth. I hardly recognize myself. I finished washing myself, got out, dried off, and walked into the living room.

“Wow, nice legs Chris!” Kelly said, while Lisa laughed a little.

Before I could say anything, Kelly handed me a hot pink lacey thong, “Put this on and cover yourself up.” I did as I was told, and she then handed me the bra from before, and helped me put it on. Kelly then stuffed the bra with some breast inserts, to make it look like I actually had boobs.

“What are you thinking, Lisa, a nice mini skirt?” Kelly said. “I think so, and that cute white crop top I have,” Lisa replied. Kelly nodded, and they both went to their rooms. Kelly came back with a very short and tight, black mini skirt. Lisa came back with a white crop top with spaghetti straps. They both handed them to me, I put the mini skirt on first, and then the crop top. The skirt barely covered my whole butt, and was very tight, while the shirt was looser, but didn’t even reach my belly button.

I laughed, “Alright, I’m a girl, so how about that blowjob.”

Lisa and Kelly looked at my and laughed, “We still have to do your makeup, and nails, and hair. Plus, shoes. Now sit down on the couch.”

I figured if I already shaved myself, and was wearing what I was wearing, what’s a little makeup and nail polish?

Kelly and Lisa walked over with a bunch of makeup and went to work. Covering my face with foundation, then adding purple eyeshadow, followed my some eyeliner, mascara, and finishing with hot pink lip gloss.

Lisa then painted my fingernails, and toenails hot pink. I thought I was done, until Kelly walked about with a wig. She smiled and put it on. Lisa then gave me a pair of heels to put in.

They both took a step back and looked at me, and smiled.”Wow, he…I mean she looks hot!” Lisa said. “For sure, we did a great job…want to see?” Kelly asked. “I guess so…” I stood up, trying to balance in the heels, while Kelly led me to her room and her full length mirror.

I looked in it, and didn’t even recognize myself. I really looked like a girl, and a hot one too! I was speechless. I barely noticed that Kelly and Lisa were whispering something to each other.

“Sit on the bed,” Kelly said, “and lean back.” I did as I was told, getting ready for what I thought was the blowjob, I closed my eyes, and waited. “Your eyebrows are not girl-like,” Lisa said, and she started to pluck them.

“What the…” I said.

“Stop moving, and be quiet!” Lisa yelled, as she continued to pluck them. After about 30 minutes of plucking, Kelly and Lisa looked at me. Kelly smiled, and said “I have these temporary tattoos, let me use one to give you a tramp stamp! Rollover!”

I figured it was just temporary, so I did, almost everything else I have done so far would last much longer. I felt her apply it, while Lisa laughed. When she was done, Lisa said, “Ok, seriously, one for thing, and then Kelly can give you that blowjob.”

“Sure, anything!” I said with a smile, figured the worst was done with. Lisa smile, “Lay on your back, and close your eyes, and don’t squirm or anything.”

I wasn’t sure what Lisa and Kelly were doing, but they were giggling while touching around my stomach, I felt a small pinch, and then Lisa said, “Ok, open your eyes.”

I opened them, and looked down, and saw they just pierced my belly button. I was stunned and looked at them with my mouth open. They looked at me and laughed. “Now you’re pretty much a real slut,” Kelly said, “now stand up and walk around and show us your stuff!” I did, and walked around the apartment while they told me how to walk in heels. After about 15 minutes, I was getting pretty good at it.

“Ok, this was fun, girls, but can I take it off now?” I asked.

They both laughed, took their phones out and snapped some pictures, I posed for a few of them, just to play along. “You can take it off if you walk down the hallway and back a few times. No one will know your aren’t a girl, don’t worry about it!” I nodded, and went into the hallway, while Kelly and Lisa took more pictures and some videos. As I started to walk back Kelly tossed my wallet and phone at me. Her and Lisa went into the apartment, slammed the door, and then I heard it locked.

I knocked on it, and no answer. I knocked harder and still no answer. I started to pound on it, and heard Lisa yell “Go away, or we’re calling the police and saying you’re trying to break in to your place!” I stopped, and waited for 5 minutes, then Kelly texted me a picture of me dressed up which read “Go home, or we’re sending this to everyone we know!”

Realizing she wasn’t joking, I headed back home, hoping no one would notice. I got down to the sidewalk, and headed back to the subway. On the way, I noticed a few guys checking me out, but was still nervous I would see someone I would know.

When I reached the subway, I stood on the platform and waited nervously. All of a sudden a guy came up to me, and looked at me.

“Hey gorgeous, what’s your name?” He said.

I hesitated, then tried to raise my voice a little, “I’m…Ashley,” I said, saying the first name that came to mind.

“Well, Ashley, would you like to give me your number? I will treat you good.”

“No…thanks,” I said as the subway pulled up. I immediately got on the most crowded one, away from the creepy guy.

I sat down, then immediately stood back up. I forgot I was wearing a skirt, and felt the seat against my butt. I sat back down, and made sure the skirt stayed under me, instead of riding up. I also made sure my legs were tightly closed so no one would see up my skirt. I sat in silence and looked around for anyone I knew. I didn’t see anyone, and thought I might be able to make it back to my apartment, and change, and undo everything. While wishing the subway could go faster, I looked down at my belly button ring, and thought that it did look cute. I also thought that my pink nails looked good, and shaved legs wasn’t so bad. I was so lost in this train of thought that I almost missed my stop! As soon as I realized it was mine, I jumped up, and quickly got off the train, and headed to the street.

My feet started to hurt from the heels, but I made it to my apartment building, entered the access code to get in, and took the elevator up to my apartment. I got to the door and realized that Kelly never gave me my apartment keys. I stood at my door stunned, and hoping Brian, my roommate, would be home.

I knocked, and thought how I would explain all of this to him. He answered the door, and looked at me, “Uhh…can I help you.”

I took a deep breath, “’s me, Chris.”

“What the hell dude? What are you wearing?”

“Long story,” I said as I walked into my apartment.

He looked at me, and started laughing, and fell over from laughing so hard. “Oh man, you have to tell this story!” He laughed again, “Is your belly button pierced?!”

“Yeah, let me change real quick…” I walked to my room, and realized my bedroom door was also locked. Brian looked at me and laughed.

“I’d give you some of my clothes, but I want to hear this story first!” He said.

I looked at him, and told him everything Kelly and Lisa did. When I finished, he looked at me and laughed. He then walked around me, checking my out. “Love that rose bush tramp stamp, that’s the sign of a real slut!”

He took out his phone, and took some pictures. “I think this could be fun, and I think you’re kinda enjoying this right now.”

“Well….” I said while laughing.

Brian looked at me and smile, he took a step towards me, and squeezed my butt. He brushed the wig hair out of my face, and gave me a slight kiss on my neck.

“What are you doing…?” I asked. “Well, there’s a little slut in my apartment….” He smiled, “what’s your name?”  

“Ashley,” I immediately said, while he kissed my neck again.

“See, you’re liking this.” I was enjoying, and didn’t realize my hand moving toward his crotch. Brian looked down, “It’s ok.” I started to slightly rub his cock over his jeans.

“That’s right, rub it my little slut. I know you want it.” Brian started to rub my ass, and kiss my neck some more, and I kept rubbing his cock. “How about you take it out?” I looked at him. I have never seen another guys cock before in person, much less done anything with a guy.

“It’s alright,” he said, “I know you want it.” I looked down, and undid he belt and fly. “It’s easier to do that if you’re on your knees,” he said with a smile. I looked at him, and slowly got on my knees, so my face was level with his crotch. I finished undoing his pants, and pulled down his pants and boxers. Out popped a large semi-hard cock. I stared at it. “Touch it,” he said.

I looked up, and slowly grabbed it stroked it slowly. I was doing something I never thought I would do, which was touching someone else’s cock. I started to go a little faster, and it grew a little in my hand. I started to look at it closer. It was a big cock, probably would be around 8 inches fully hard. And Brian had it completely shaved. It was thick too.

“How about you kiss it?” He said, as he smiled down on me. I gave him a small smile, hesitated, and licked the head. “That’s right…” Brian said. I licked it again, looked up and saw he was really enjoying it, which made me enjoy it a little bit. “How about you stick it in your mouth, Ashley?” I looked up at him. “I’ve never done this before…”

“Just try it, Ashley.”

I opened my mouth, and slowly wrapped my pink-glossy lips around his cock, and slowly went down on it, so the head of his cock was in my mouth. I went down a little more on his cock, and looked up to hear him moan.

“Oh, fuck Ashley…”

I went down some more, and back up and then down again. I came off his cock, and looked up at him, “I thought I would be getting a blowjob today, not giving one!”

He looked down and laughed, “well, plans change, you’re good at this…”

Encouraged, I went down even further on his cock, and started to massage his balls with my hands.

“Mmmm….keep it up, Ashley. You’re my slut today.”

I go down further on his cock, and up and down. His moans turning me on. My tongue swirling on the underside of his cock. I come off his cock, and look up. I slowly stroke his cock as I start to suck his balls.

“Fuck I love that…fuck yeah…” he says.

I look up at him and smile. I look at his cock, and see a pink lip gloss stain about halfway down. I then see a lob of precum leak out.

“Taste it” he says.

I stick my tongue out, and lick it all up, and find the taste isn’t half bad. I see him smile in satisfaction, as I swallow it. I go back to sucking his cock.

Up and down, and start getting faster. I then try to take it all the way down my throat. I get almost all the way down, but gag. “Try again…” he says with a smile. I go down slowly, trying to keep my throat open, and eventually get it all the way in. “That’s a good little slut” he says, while he holds my head down on it for a few seconds.

I smile up, and wrap my lips tightly around his cock, and as fast as I can, go up and down on it. His moans increasing. With every moan I speed up a little, and make my lips even tighter. My tongue playing with the underside of his cock, and head. “OhhhHH!!!” he yells out.

All of a sudden, I feel his cock throb and pulsate, and a weird taste fills my mouth. His warm cum filling my mouth. More keeps coming too.

“Ohh yessss Ashley” he says. I wait until he stops cumming, and look up at him, I take my mouth off his cock. “Show me it” he says. I open my mouth and show him all his cum. The taste starting to bother me. “You know what to do….slut.”

I close my mouth, and swallow it all down, and feel it slowly go down my throat.

“That was a great blowjob…you’re meant to suck cock. Can’t believe that was your first time with a dick in your mouth.” I look up and him, “I was actually hoping to….” I stop what I was about to say.

“Hoping to do what?”

I hesitate again, “I don’t know why, must be these clothes and sucking your cock, or something, but I….kinda want to get fucked….I know you just came…but…”

Brian laughs. “You are a little slut….suck my cock some more. Get it hard again.”

I smile, and start to lick his semi-erect cock. And go back to sucking it, as it grows and grows in my mouth. I go up and down on him some more. “That’s good, lets go to my room” he says.

I stand up and he grabs my hand, and leads me to his room. He wraps his arms around my, and takes off my shirt, being careful not to disturb the wig. He gets on his knees, and removes my skirt, and the thong — leaving me standing in his room in only the bra and heels.

“Get on the bed…..on your back like a good slut” I smile, and do as I’m told. I lay on my back, and open my legs and expose my ass. He gets between my legs. And strokes his cock a little. “Do you…have a condom?” I ask. “Sluts like you don’t use them.” I smile. Every time he calls me a slut I seem to like it.

He gets closer to me, and almost on top of me. I start to breath deep. He puts the head of his cock on my asshole, and rubs it up and down. He then slowly starts to push on it. When he starts to, I push out a little, and when I do, he smile.

“Sluts like you know what to do…it’s like it’s instinct.”

He pushes a little harder, and I feel the head pop into my ass. It’s a weird feeling. It hurts a little, but it doesn’t feel bad. He pushes in a little more. A moan escapes from me. He slowly pushes more, my ass getting a little wider.

“You’re now my official slut, Ashley.”

He pushes more in, then slowly pulls out, and back in. He does this a few times. I then realize I’m getting fucked. I moan as he starts to speed up just a little. He goes a little harder, I then reach to stroke my cock. He slaps my hand away.

“Not today slut…” he says. He starts fucking faster, and harder. He goes for a few minutes fucking my ass, while I moan out. He then pulls out. I look at him.

“Time to ride it, slut.” He rolls over on his back. I move over, and straddle him. I position my ass over his cock, grab it, and guide it into my ass, and slowly lower myself all the way down. I go all the way down, and slowly all the way up.

“Your ass is so tight…” he says, as I continue to ride his cock. Slowly starting to go faster and faster. My semi hard cock bouncing up and down, as he smiles upon me. Encouraged by the smile, I go faster, he reaches up and spanks my ass. I go faster, and he spanks me again. He spanks me harder, and each time I let out a little yelp.

“Damn….you’re almost a pro at this” Brian says. Brian then pushes me off, “let me fuck you from behind….just like a real slut.” I smile, and get into position. Brian gets behind me, and pushes his cock in my ass. “That’s right, slut, take my cock from behind.” He pushes it all the way in.

“Oh baby….keep fucking me…” I turn around and see him smiling, as he records him fucking my ass on his cell phone. He laughs, “Yeah, this is going to Kelly…”

I smile, “ohhh baby, I like this.” He then starts to fuck me harder, “you’re taking this like a real slut! I love it!”

He goes harder and faster. He grabs the strap of my bra and goes even harder and faster. The entire bed shaking, and me yelping out in excitement.

“Ohh Brian, your cock feels so good in me!” I yelled out, loving the life of being a slut.

“Get ready for me to fill you with my cum! I’m gonna nut soon!” I smile, as he continue to pounds away at my ass. “Ohhh, I’m close Ashley!… it comes!” He thrusts a few times into me, hard, and moans. I feel his cock pulsate inside me. I moan a little.

Brian laughs, “now you’re officially a dirty little slut.” He pulls out of me, and I feel his warm cum leak out of my ass. “Look at me.”

I turn back and he snaps a photo of my face, with the cum leaking out. “Now, get those slutty clothes back on, and clean yourself up. You’re my slut now, I’ll have to think about what to else to do with you.”

written by sissy_whore4bbc on IG

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