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A True Sissy
🕑 Added 2023-03-03 16:29:55 +0000 UTCFull Story:
My name is Ashton. I am a 23 year old white male, living in downtown Atlanta in my studio apartment.
As far as real life goes, I am straight. But behind closed doors, I have been going deeper and deeper down a rabbit hole of crossdressing and big black cock porn.
Like most sissies, it started just by watching some of favorite pornstars go black. But before I knew it, I could care less about the girl, I was just drooling over the black men on my screen.
My searches used to be female driven — Riley Reid, Giselle Leon, and Piper Perri. But now they are Mandingo, Jack Napier, Shane Diesel. Basically, my search became whoever's big black cock was I craving that moment.
Living alone had it's perks. Once I crossed the threshold of trying on my first pair of panties, I was addicted. I ordered more and more clothes. All sexy. All slutty. I even ordered a small vibrator. I loved teasing my asshole with it while jerking off in my panties while scrolling through countless images of big black cock.
I loved the nights I would stay up so late watching porn that I would fall asleep in my lingerie. I always woke up so horny that I would immediately need to see Mandingo's big black cock and would cum in my panties almost instantly.
However, as most sissies, I went through cycles of shame that would lead to purging my clothes and trying to be normal. But sissy cravings always came back and I would order more lingerie.
My best orgasms were always in lingerie, there was no denying what turned me on.
Enough background!
It was mid-December, and I was going through another shame spiral about my big black cock loving sissy habits. I decided that I was going to do one final splurge. I would order a bunch of new sissy clothes and a big black dildo so I could have my own sexy New Years Eve. But that would be it, my sissy finale. After that, I would throw it all out and put these habits behind me for good.
I went onto Wicked Temptations and ordered about $200 of clothes. Mostly the usual lingerie, but this time I also ordered a short red dress with a petticoat to go under it as well as a pair of black stilettos.
I even ordered some mascara, eye liner, and lip stick.
And the best of all, I found a big black vibrator. Veiny. Thick.
I reached into my panties and came as soon as I touched my penis, I was so turned on.
Over the next few days, I must have checked the shipping tracker 100 times. Eventually the packages started arriving, and I showed incredible restraint by not opening until it was New Years Eve.
Finally, it was New Years Eve and I could barely contain my excitement. I shot out of bed and walked to the grocery store to get some food, champagne, and red wine.
The previous night, I toyed with the idea of shaving all my body hair. I stood in the razor aisle for a minute and said fuck it, before tossing a new razor and some female shaving cream into my basket.
My penis twitched in my pants thinking about what it will feel like to be completely smooth.
I pretty much ran home. Given how late I stayed up last night watching big black cock porn and thinking about today, I slept in pretty late and it was already about 1pm.
I made a quick lunch, and hopped in the shower to get ready.
My penis got immediately hard just thinking about what was to come. I wanted so badly to jerk off but decided just to enjoy the heightened sensation and go about my business shaving my body. Not that I am terribly hairy to begin with, but it still took a while. By the end, I felt so smooth. So sexy.
I got out of the shower and admired my work. My penis looked almost feminine without any hair. Like the sissies in porn. I wrapped my hand around my rock hard penis and give it a stroke. One stroke. That was all I would allow.
No cumming yet you little sissy white boy, I thought to myself.
I went into my room and pulled out the three packages from under my bed.
First, the make-up. I pulled my hair into a ponytail instead of my normal man-bun and put on the red lipstick, eye liner, and mascara. I didn't really know what I was doing, so it wasn't perfect, but it looked pretty good and made me feel sexy and feminine.
Next, the clothes. I tore open the package and sifted through everything that I ordered. I decided I wanted to just hang out and sip wine in a the dress, petticoat, and heels until it was time to change into a new set of lingerie for my first time with the big black dildo.
My penis twitched at the thought. I grabbed it again and gave it one stroke. Just one stroke little sissy! I thought to myself.
I had all sorts of lingerie in the package, but I decided I would wear a lacy black bra and panty set under the dress now. While saving a purple set with white garters for my big black dildo fucking later.
My hard white penis was dripping pre-cum as I stepped into my black lacy thong. I felt like such a slut for being this horny, but I couldn't help myself.
I moaned as I felt the tight lacy panties slide up my smooth legs and engulf my hard penis. I was cursed with a small penis, but I also loved how neatly it fit into panties, even when hard.
I positioned my penis in my panties so it was pointing straight up, against my body. I giggled that even when fully erect, the head of my penis didn't even stick out of the waistband of my panties.
Next came the bra. I love bras for their feminine signal, but they don't have the same effect as panties on me.
I decided to step into the heels next. I admired how good my legs and ass looked when I was tilted up on my tippy toes in them. I took a few wobbly steps in them but then got the hang of it. I loved how my hips swayed as I tried to walk one foot perfectly in line in front of the other.
Petticoat time! I stepped into it and adjusted it on my hips. I felt silly looking at myself in the mirror, but I loved how short it was and it made me feel sexy.
The dress was next. This was my first time wearing clothes, not just lingerie. I slid it on before straitening it on the petticoat. Oh my god it felt so good.
I looked at myself in the mirror and swung my hips around, watching how the petticoat teased a view of my sissy ass.
I walked into the kitchen, opened a bottle of red wine and poured myself a glass. I took a sip.
This was so fun! I was so horny. I could feel how hard my penis still was in my panties as I sat down on my couch and crossed my legs like a woman.
I usually just watch porn on my laptop, but since it was a special occasion I decided to stream it through my 70" TV. I moaned as the opening scene of Riley Reid worshipping Mandingo's big black cock came onto my TV. My goal was to watch the entire 32 minute video without playing with my penis.
Throughout the whole video, I sipped my wine like a good sissy and refrained from touching my penis. Every now and then I would flex my thighs together harder to squeeze my hard penis, but that was it.
It took tremendous restraint. After the video concluded, I felt like I had earned the big black dildo. It was so much bigger than mt vibrator. I wasn't sure if I could take it, but I wanted to try.
I queued up an hour long Mandingo compilation video and went over to my bed to open the last box. I ripped it open and my eyes nearly popped out of my head.
It was huge! I knew it would be given how heavy the box was, but it was still shocking to see. I lifted it up, marveling at it's size, and took it to the sink to wash.
I bit my bottom lip as I rubbed my hands up and down it under the faucet and soaped it up to clean it. It felt so much bigger than my own little penis. I wanted to compare it.
I walked over my couch and laid down a towel, before kneeling down on it. I pressed play on the video before lifting up my dress and pulling out my little, but very hard penis. I held the big black dildo next to it.
It absolutely dwarfed my little white penis. I moved the dildo under my penis and rubbed myself against it.
I moaned.
This dildo was advertised as a realistic big black cock. How could someone realistically be this much bigger than me? No wonder I am a sissy. If black men were walking around with this in their pants, how could I compete? No wonder my sexual adventures with women had been such a failure. I was tiny! Size does matter.
I squeezed a generous amount of lube onto the dildo and positioned it under me, pressing it against my asshole.
I started lowering myself down onto it. My body wasn't ready for it. The black dildo was so much bigger than any previous intruder that I had played with my sissy ass with.
But I was determined. I bit my lip and ground my ass down, putting more and more weight on the dildo.
Eventually, POP, the head slid in. I moaned really loud and caught myself before I slid down any further.
It hurt a lot more than I was expecting. I tried to catch my breath. I watched Mandingo's big black cock as pain rippled through my ass.
Maybe I shouldn't do this. I didn't want to hurt myself.
I stayed in that position, letting my body adjust to the big black dildo, when I was snapped out of my big black cock addicted sissy trance by the fire alarm.
I figured it would stop, but it didn't. I heard people leaving the building, then the fire truck sirens.
Panicking. I lifted myself off the dildo, folded the towel over it. Took the heels, dress, petticoat and bra off, slid on a pair of sweatpants, sweatshirt, and grabbed a blanket to wrap myself in and ran outside.
I stood off to the side wrapped in my blanket as the fire department went into the building. There were maybe 30 of us outside.
I made eye contact with one of my neighbors who I recognized but never met. He was a big black guy, probably 6'5". And super fit. I had seen him in our gym before, and I could tell his work in the gym paid off because he was shirtless. He had a legit 8 pack, and muscles on top of his muscles.
Shit, he was walking over.
"It's cold as shit, care if I get under that blanket with you? I was half asleep when the alarm went off. Scared me so much I almost forgot to put shorts on!" He laughed.
"Ummm....sure," I said opening the blanked so he could come in. But it didn't really work given how much shorter I was.
"Here, give me the blanket," he said, "I'm so much taller than you it will be easier for me to wrap it around my shoulders and wrap you up instead of the other way around."
I agreed, handing him the blanket. He wrapped it over his shoulders and then wrapped me up in front of him. I am only about 5'6", so he is nearly a foot taller than me.
The blanket wasn't huge so he pulled me in close. I could feel his hard abs against my shoulder blades. I think I even may have felt his cock against my lower back. I felt so small compared to him.
"It's cold as shit!" He said, hopping up and down a bit to get his blood moving.
The result was that his body was gently grinding against mine. I could definitely feel his big black cock.
My penis had gotten soft in my thong with all the commotion, but it was twitching back to life. I hoped he wouldn't notice.
"I'm DeJuan, you can call me D," he said, "thanks for letting me warm up with you."
"No problem! Nice to meet you D. I'm Ashton. I think I have seen you at our gym before," I replied, making small talk.
"Ah yea, that's right. The cute little blond on the stair master, working that ass out!" He laughed.
I just nervously laughed. I wasn't sure how to respond, but then I felt his hand under my shirt on my belly. He slowly spread his fingers so his pinky went into my sweatpants and pulled me back into his crotch.
He didn't say anything but I panicked knowing that he must have felt the lace from my panties.
He motioned his hips, just slightly grinding into me. I didn't know how to stop him. I felt trapped. My penis ached.
"Just a burnt frozen pizza," the fireman yelled coming out of the building, "try not to pass out while making pizza apartment 6C, feel free to go back in.
Someone yelled "sorry!" Probably whoever lives in 6C.
"Alright, well I'm going to head in," I said, trying to break the tension.
"Sounds good, thanks again," D said before handing me my blanket.
I quickly walked back to my apartment, what the fuck just happened. I didn't even put my dress back on. I was so horny that I hopped back onto the couch and slid right back onto my dildo, thinking of D's big black cock pressing against me.
Why didn't I tell him no? Why did I just let him manhandle me?
I moaned and slid down further, watching Mandingo on my TV and thinking about D.
Knock knock knock. Shit someone was at my door.
I turned the TV on mute.
Knock knock knock.
I stayed still, hoping they would go away.
"I know you are in there Ash, we just came inside like 3 min ago. I brought you a thank you gift for keeping me warm," D said at the door.
Shit!
"One second!" I yelled.
I hopped off the dildo, flipped the towel the dildo, turned my TV off and pulled on my sweatpants and sweatshirt again.
I walked over to the door. As soon as I started opening it, D pushed his way in, walking right passed me.
He went and sat on the couch, right next to the towel and dildo. He still hadn't put a shirt on.
"Like I said, just wanted to swing by and say thank you for keeping me warm. I brought a blunt we could share. This is some of my best stuff," he said as he started to light the blunt.
He took a small hit, then a big hit, and held out his arm to pass it to me.
"Thanks D," I said, trying to play it cool.
I accidentally took a big hit and coughed. We both laughed.
"As you can tell, I don't smoke very often," I said, before taking another more controlled hit.
The weed hit me fast.
"Whoa, this shit is strong," I said, walking over to the couch, sitting down just about arms reach away from D.
I handed D the blunt.
"Yea, I like to call this weed the white boy killer," he said, taking another hit.
"Why is that?" I asked.
"Let's just say, it makes everyone horny. Just in different ways. I bet that sissy ass of yours is starting to ache," he said.
I blushed. He was right. My mind was racing as I felt the thong stretch against my asshole. I thought about the big black dildo which had just been partially inside of me. My ass ached as I thought about the pain from trying to slide down it.
I bit my lip as I felt pre-cum leak into my panties, thankfully under my sweatpants.
He handed the blunt back to me, I was trying hard not to stare at his body. He was so manly, so sexy.
I was mid hit when he picked up the remote.
"Were you watching the game?" He asked, flipping the TV on.
My stomach sunk as Mandingo's big black cock filled the TV screen, picking up where I had left off.
"Oh damn, isn't this interesting! You like big black cock?" He asked.
How the fuck was I going to get out of this?
"I...ummm...I...I just really like all types of porn," I said, trying to play it cool, taking another hit.
The play it cool strategy didn't work. He pushed the back arrow to get to my search bar and history popped up. It was full of black male porn stars only.
"Is that so?" He said winking at me.
I was caught as he laughed and scrolled through my rolodex if black cock related searches.
He stopped scrolling, "Sissy big black cock trainer," he laughed before clicking on it.
I turned bright red. I was mortified. I just stared down.
He pushed play and leaned back, taking another hit.
I looked at the screen as familiar images of big black cocks juxtaposed to little white penises in panties scrolled through on my huge tv.
"Damn, this is some crazy shit. You really got it bad, don't you Ash?" He said.
"It's just for fun. A fantasy. I'm not gay, I've never been with a guy," I said.
"Sure Ash," he said passing my the blunt.
I took another hit, trying to keep playing it cool.
"I like your make-up," he said.
Shit, I had completely forgotten I had it on. That whole time outside I had it on. No wonder he pegged me for a sissy.
I just sat there silently, watching the TV. I reached over to hand him back the blunt. He took the blunt with his right hand and grabbed my wrist, pulling me towards him with his left hand until I was sitting right next to him, facing him.
In the process, I knocked the towel off of the couch and the big black dildo rolled out onto the floor.
He looked at it, then looked at me. He took a hit of weed and pulled my head towards his and gave me a deep kiss. His tongue invaded my mouth like he was trying to lick my throat. I sucked him in as he blew smoke into my mouth.
I was so high. I could feel my hard penis in my panties as I knelt next to him. Kissing him.
"I know you are wearing panties, Ash, let me see them," he commanded, gently guiding me off the couch to stand in front of him.
I heard moans coming from the TV as i took off my sweatshirt and sweatpants. I stood there in front of him in just my black lacy thong. I felt cold. My penis was so hard in my panties though.
"Turn around, let me see that ass," he instructed, taking another hit.
I slowly turned around.
"Damn baby, that ass was made for my big black cock. I hope you practiced with that black dildo or else I'm going to tear you apart though," he said, grabbing his big black cock over his shorts.
I bit my lip as I saw the fabric of his shorts wrap around the outline of his big black cock. It looked enormous. I couldn't help but stare.
"See something you like?" He asked, wagging his black cock at me through his shorts.
"I...umm...I..." I stuttered.
"I know baby, I know it's all just a fantasy for you. We don't have to do anything that you don't want to," he said, stroking his big black cock, staring at me.
Before I realized it, he pulled out his phone and took a picture of me.
"Stop it! Delete that!" I said.
"Calm down baby, it's just for me. You look so damn sexy. Why don't you go change into something even sexier for me so that picture does stay just for me," he said slyly.
"Are you blackmailing me?" I asked, frustrated.
"It's whatever you make it sissy boy," he said, taking another hit, "now go change."
I went back to my closet and picked out the purple set I wanted to wear later anyways. Purple satin thong and bra set with embroidered white flowers. It also had matching garter with white stockings.
Not going to lie, the satin and the stockings felt amazing between the weed and my hairless body.
I stepped into my heels and walked back in between him and the TV.
"Is this better?" I asked, half pouting, half playing.
"Damn baby," he said, "you really went all out for your black daddy, didn't you?"
I blushed. I was high. I didn't really think of it like that. He would have been none the wiser if I just put on a different bra and panties. Why the hell did I go all out getting dolled up for him? I even put on heels!
He stood up and walked right up to me, giving me a kiss. He then grabbed the back of my neck and gently but forcibly pushed me onto my coffee table.
Next think I knew, I was on my hands and knees on the coffee table as he walked around me. I could feel the straps from my garter stretch across my thighs and ass.
He walked around me, rubbing my body. I knelt there as still as could be. When he got to my ass, he stood behind me and grabbed my hips.
"Yea, I'm going to have fun with this tonight," he said before smacking my ass and continuing to walk around me, inspecting me.
He sat back on the couch.
"Why don't you come sit on my lap baby," he said.
I got off the table and went to sit on his lap for a bit.
"No, face me. Maybe I'll let you delete the picture I took," he said.
I climbed onto him, straddling him as I knelt on the couch.
I could feel my little penis rub against his big black cock. He knew I was thinking about it.
"You like that baby," he said, grinding his hips up and grabbing my ass pulling me into him so my penis rubbed up and down his big black cock. Only my purple satin panties and his basketball shorts separating us.
He started grinding faster, I dry-humped back against him.
"Oh fuck," I moaned. I was close to cumming in my panties.
"No cumming yet sissy," he said, abruptly stopping the dry hump.
"Why don't you take a look. Let's compare sizes and then you can delete the picture," he continued.
I nodded in agreement as I reached down into his shorts with both hands.
I'm not sure why I used both hands, it's not like my penis was big enough to hold with 2 hands, but I just assumed I would need two.
I moaned as I lifted my hips up to make room for my hands and slid them down. He felt enormous as I lifted my hips up and down to run my hands back and forth over the length of his big black cock.
I kept going for a minute, jerking him off with both hands in his shorts.
"I didn't say anything about a handjob, but damn that feels good Ashley," he said.
I moaned as he called me Ashley. Given my name, Ashton, it was the easy choice for a sissy name, but it had always been what I called myself when I fooled around. It was so hot coming out of his mouth.
But I also realized he was right, he just said look at his big black cock to compare to my little white penis, he said nothing about jerking him off.
Embarrassed, I let go of his big black cock and tugged down on his shorts. He lifted his ass to help, but eventually, his shorts hit the floor and I looked down.
He had a cocky smile on his face, "what do you think sissy?"
I was mesmerized. It felt big. It felt enormous. But it was different to see. I grabbed hold of it and examined every inch. It had to have been 12 inches long and as big around as a 16oz water bottle. I didn't say a word as I rubbed my fingers along its veins.
My little penis didn't have visible veins.
I pulled it up against me and mashed my hard little white panty covered penis against it.
He laughed.
"Do your thing, just no cumming yet," he said, leaning back and putting his hands behind his head.
I wanted to keep humping his big black cock, but I didn't want to cum like he said, so I stopped and slid down to the floor so I was eye level with it.
I looked up at him with puppy dog eyes.
"Can I please suck your big black cock, Daddy?" I pleaded, slowly stroking him.
"You sure can Ashley," he said.
I pulled his big black cock towards me and took him into my mouth.
"Mmm, that's a good sissy," he said as my tongue twirled around the underside of his head. His cock was too big to be able to move my tongue all the way around, so I had to focus section by section.
His big black cock was nothing like my little penis.
Black vs white. Thick vs skinny. Long vs short. Manly vs feminine. Strong vs dainty. Everything was different.
I have no idea how long I worshipped his big black cock. I was doing my best Riley Reid impression. It came so natural. I just thought to myself — what would feel good if I had a big black cock — and did that.
I couldn't help but feel a tinge of pride when he said, "damn, you sissy boys really do give the best head."
It made me want to work on his big black cock even harder. As I worked to pleasure him, my hard little penis strained for release in my panties.
"You know this is just the start," he said as he placed one hand on my head to hold my me on his big black cock, "I'm going to fuck your little sissy ass tonight and every last ounce of manhood that you have left will leave exit your body with your first big black cock induced orgasm. Once that happens, you will be my sissy bitch. You will obey me, you will take care of me financially, and take care of me sexually. I will move in with you. You will cook, clean, do my laundry. And you will always do it with a smile while dressed in the sluttiest outfits imaginable. How does that sound Ashley?"
I shook my head in agreement before taking my mouth off of his big black cock.
"Yes, Daddy," I said in between catching my breaths.
"Good girl, now come see what you've been missing your whole life," he said, pulling me up off the ground.
He stared deep into my eyes as I climbed on top of him. He just sat there with one hand on my ass and the other holding the blunt up to his mouth.
He wasn't going to fuck me yet. He wanted to break me. To humiliate me. I had watched enough sissy porn that I knew exactly what he was doing. He was giving me the reigns to end my old life and start anew.
I was going to have to climb up onto his big black cock on my own accord. I was going to have to reach down and position his big black cock against my ass. I was going to have to lower myself down onto his big black cock. I was going to have to ride his big black to orgasm.
I knew all this, but I couldn't stop.
I steadied myself on his shoulder with one hand and reached down to grab his big black cock with the other. Using one hand, my hand didn't even come close to wrapping all the way around it. Maybe halfway.
I positioned it against my virgin sissy ass and held my breath as I slowly lowered myself down.
"Oh my god, your big black cock is fucking huge," I moaned and grimaced as I tried to wiggle my way down.
I couldn't just lower myself down. He was too big, too thick. My body stalled out. I quickly learned that I had to ride my way down.
I would lift myself up an inch before sliding back down 2 inches. Then up 2 inches before lowering myself down 4 inches. Up and down I went as I tried to get more and more of his big black cock inside of me.
Every inch, every centimeter more I took of him brought me to new heights of pleasure.
He sat there with a cocky smile on his face as I held onto his shoulder for dear life as I fucked myself up and down his big black cock, aggressively trying to get every last millimeter of him inside of me. I was so horny.
After about 10 minutes of this, I sunk down one last time and my ass cheeks hit his thighs.
I lost my breath.
"Oh shit, I can't believe I did it," I said.
"Good girl," he said, grabbing the back of my head and kissing me deep.
I looked down and the front of my purple panties were now a deeper shade of purple. I had been leaking pre-cum through most of this ordeal and every time I went further down, his big black cock would squeeze some sissy cum out of me.
"Are you ready for the best orgasm of your life?" He said as he waited for my body to adjust.
"Mmhmm," I said as I closed my eyes and bit my lip.
I started to ride him. Up and down. Much like earlier but with purpose beyond just getting him inside me. I wanted to cum. More importantly, I wanted him to cum.
I started to ride him up and down, slowly at first. But I quickly gained more confidence and found my groove. Up and down I rode.
I quickly found that the best part of a big dick is that I could leave 6 inches of him inside of me while riding up and down another 6 inches. When i a girl had ride my small penis before, I kept falling out of her because there was barely enough penis to ride.
I loved it. I closed my eyes and moaned as I found my groove. He held my hips with his strong hand to give me a gently guide. He knew what I needed.
I felt my orgasm building, and he picked up on it. Heavier breathing. Losing control. Moaning.
I started to work harder towards the orgasm. I knew if I reached down to touch my little penis that it would erupt within seconds, but I knew better. All my sissy porn habits had taught me that a sissy is not to touch her penis. It is purely ornamental.
"Oh my god, I think your big black cock is going to make me cum," I moaned as I buried my head into his neck.
Up and down I rode, chasing my first sissygasm. I needed to cum so bad. Nothing else mattered. I felt in that moment that nothing else mattered and I existed for this one singular purpose, to ride Daddy's big...black...cock.
Up I went, almost to the tip of his cock. I had just his bulbous head left in me. I went to sink myself down a few inches but Daddy grabbed my hips and in one firm push, slammed me all the way down onto his big black cock.
I screamed in pleasure as the full length of his big black cock shot into my sissy ass.
My little penis erupted as he bottomed out inside of me. My whole body shook. My penis twitched as rope after rope shot into my panties, my legs shook, my toes curled, and I dug my nails into his back.
It was truly my first body crunching, mind numbing orgasm.
It was amazing. I knew at that moment that I was addicted and sex would never be the same. Sex with a woman would no longer be possible. From that point on, I knew I needed big black cock to ever feel pleasure again.
"I'll do whatever you want. Whatever you need Daddy," I whispered while trying to catch my breath. "I am your sissy, just please. Please. Please, never stop fucking me."
To be continued if there is interest!!
Comments
Derek Brown
I dio lke these stories but even more if the sub is made to be a domestic maid or possibly auctioned off at a slave sale
sean mcguigan
defiantly an interest
