Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click hereEveryone in the story is 18+
And looking forward for an author to edit add you word and republish(you dont need my permission for that)
My mom, 36 years old, is a strong MILF.
Me, an 18-year-old skinny, girlish boy
Aunt, 34 years old, strong, white MILF
I am the only child for Mom. She is good and sexy.
We live in an apartment on the 40th floor. Next to ours is my mom's sister, or my aunt. She is also single, dresses hot, and she is a cybersecurity executive.
My mom was single from the day I was born.
She doesn't let me go out on my own. I dropped out of school and homeschooled.
She works till night, and my aunt provides me with food when she is away.
And one night I woke up late and went to the kitchen to drink, and I heard my mom moaning in her room. She was surely having sex, and I was upset and hot as well.
We had a no porn or sex in the apartment policy, and devices won't connect to porn because my aunt blocked them, so all I can do is imagine my mom and rub my dick.
I used to search for laundry for worn panties to sniff, and you know this has been going on for about 3 months. Every single time, she would fuck someone, but in the morning everything is normal.
One said she said she would be leaving her country for 15 days.
And she said to me to behave well and listen to Aunt
After she left, my aunt gave me lunch, and I ate at her place. She was so hot.
After eating, I came back to my apartment, locked the door, and went to the computer to look for porn because everything was blocked. Luckily, a website opened, and it asked me, Are you above 18? I pressed yes, and everything was interracial porn.
I don't know what kind of porn is out there on the internet, so this was the first time looking.
All the porn had titles.
MOM FUCKS BBC WHILE CUCK SON RECORDS
BBC FUCK MOM AND THEN FUCKS HER SISSY SON
SISSY PORN SISSY HYPNO
All sorts of feminisation and sissy cuck porn
I got addicted and started imagining those videos of me and my mom with a bull and jerked off.
It was 6pm and aumt messaged me she is going out amd she will be back at 10pm and she will bring me dinner so i thought i am home along for mext 4hours so went to the laundry to find moms panty but laundry was clean nothing to be found
So I walked past my mother's room; it was closed. I just tried to open it, and to my surprise, it opened.
I was once again in heaven.
Because I am alone in my apartment, Mom will only be in 15 days, and Aunt doesn't always come to check on me, so I can use the night to explore myself, but my mind told me to walk in and check for panties.
I started checking her drawers and found plenty of Victoria's Secret underwear so hot.
I quickly undressed and wore those and found lots of bras as well, but everything was big for me, and I found a pink one that matched me perfectly.
My brain was already hypnotised at the moment by sissy cuck porn.
And went through her other drawers and found variations of butt plugs from small to big.
I wanted to try, so I looked at the time; it was 6:30 pm. I had enough time, took a small butt plug, and on the table there was some lube. I applied some and pressed against my rear hole; slowly it was painful and pleasurable at the same time.
And I started looking into other drawers and found 2 dildos: one was pink, and later I came to know it was a vibrator, and a big black dildo with a suction cup, at least 10" inches. The moment I grabbed it, I was high as fuck looking at these.
sexy stuff Mom has grabbed the dildo, some larger butt plug, and the lube and walked to the hall wearing Mom's red panty and pink bra. placed the dildo on the table upright using its suction cup so I could sit on it, switched on the TV, connected to the same site with sissy cuck porn, and removed my plug from my ass and tried every plug till the large one.
The time was 7:30 pm; we had more than 2 hours left to wait for Aunt to return.
So I connected a headset to the TV so only I could hear the sound and started slowly sitting on the dildo. It was painful. I applied more lube and sat on it, letting the head pop into my hole as the video
And slowly using my body weight to sit on it completely and with 15 min the hole dildo was buried in me and my 3inch dick was already leaking cum without touching it
Changed the videos, and it was a monster dick shemale fucking a milf.
I started imagining the milf as my mom and started riding the dildo up and down till I came. I shot cum into the TV that was about 3 ft away from me, so much cum in my entire life, and I was like, Let's play later, and I was about to remove my headset first, and I froze completely for 2 long minutes.
To my left, my aunt was standing there, holding her phone, recording me. I didn't know how long
She slapped me and asked me how long this is going i didn't answer she them showed me the video. It was 7 minutes long, and it has me moaning in the video like a sissy, and she said if I didn't answer, she would send this to my om.
I was afraid of my so I answered her
She asked me, Do you like it? I said yes.
And the TV was still playing the video where a monster shemale MILF fucks a mom and her sissy son.
She pointed me to the TV and asked me what I were enjoying in the video, and I said I imagined it was me and Mom. She laughed and said thank you.
I was confused and asked why she showed me the video of me confessing to her.
I asked her how she came in. She said she has a key card that my mom gave her and said she was watching everything from the beginning through hidden cameras in the apartment and laughed so hard, looking at me and humiliating me all this while, me in my mom's panty and bra, sitting on the dildo.
She told me to get up slowly and then forced me to sit on it.
She told me to wait in the same position till she returns.
And after 5 min she came with something in her hand, left it on the table, and started humiliating me again, saying, With that thing, you can only pee; you will never ever be able to satisfy a woman.
You sissy!!
I was sad and confused. I was a virgin; I had never had sex or seen a woman naked in real life.
She then took some in her hand and said to me to open my mouth wide and placed it on my mouth. It was a gag device that kept my mouth open wide.
She looked at me with a devilish grin and stepped back a little and pulled her skirt down.
Revealing her sexy legs, she was wearing a red panty as well, but it had a bulge in it.
She them asked me are you ready for what you are born for and removed her panty feeling, revealing white veiny big cock at least 13inch in lenght and 3.5 inch in wide twice the size of the dildo
I couldn't scream; that thing could kill me.
She came forward slaped my face with her dick i was hard as rock again she spites into my mouth grabed me my hair amd inserted her dick in to my mouth
3 inches in, and it touched my throat. She said to me to lose my throat, or she will send the video and tie my hand and leave me in the men's gym.
I had nothing to do; she thrust her dick so hard with a pop, her 13-inch monster disappeared in my mouth.
My oxygen was blocked. I couldn't breathe; she took her all the way out and put it in and started fucking continuously for a good 15 minutes, and then she came in me. I didn't even get a chance to taste it because she cummed straight into my stomach.
I already came twice while she deep-throated' me, and she grabbed me by the neck and carried me up like a doll with her single hand. She was so strong.
Pushing the table away, she carried me to my room and positioned her dick in my hole without a warning. All in, and she started fucking my well-lubed ass nonstop for a good 1 hour. She cummed the 3rd time in me, but she didn't withdraw her dick from me. her dick was still hard and buried in me
Carried me with her to the hall took one of the plug in her hand removed her dick and put the plug in me and said me to not to remove unless she gives me permission
And she took me to the bathroom, washed me, and told me to wait here.
She came back in 15 minutes, and I locked my dick in a cage, took the key, put it in her pocket, wore me a nice sexy purple panty, and a pink nighty.
After that she handed me 3 big pink tablets saying painkillers, and told me to drink, so I drank it. She put me in my bed and said good night to me and left. I fell asleep 💤 happily knowing there's more to come.
woke up fresh and realised that last night wasn't a dream checked my phone, and there was a missed call from Mom. I called her back, and she said she would be back in 8 days. I was sad because I thought our fun was about to end.
Got out of bed, went to the washroom, and I was staring in the mirror with a pink nightgown raised and saw my tiny dick locked and went to pee, and I felt I had a butt plug up my ass, and my aunt said not to remove it, so I was already full of cum in my bowel, so I thought to wash it and slowly remove it, expecting cum to drip. To my surprise, there was no cum in me. I plugged it back in and went out.
My aunt came in and saw me and said, You are finally awake, and told me to come eat breakfast. It was usual; she was silently eating, and I didn't try to bring up what happened yesterday. After eating, she gave me 2 pink and 1 red pill, saying, Vitamin. I drank it without doubt.
And at 12 noon my aunt said she would be going out and told me to behave well. Before leaving, she lowered my panty, removed the buttplug, and showed the dildo that I was riding yesterday and wore my panty back and left.
I wander around the apartment with a dildo, wondering around
Each floor has 3 apartments. 1 is mine and Mom's; the 2nd is my aunt's, and the 3rd lived with a hot woman with her girlfriend, I guess.
I have seen them both going out together like a couple. The apartment's structure is like aU" shape, but no curves, just a flat "U.". From my balcony, I can see my aunts and the other
I was wondering what they were doing and went to my balcony to find out. The other person's balcony had a drying line to dry clothes, and I saw some sexy lingerie, and I started to goon.
And in a few minutes I started hearing moans through the balcony. Her name is Aiysha.
I thought they brought some men, and after about an hour, Aiysha walked to her balcony with a cigarette in her lip, wearing only a towel. I quickly hid.
And boom, I sneezed, and she called me. I just raised my head and said hi.
We had a conversation, and she asked me why I was hiding and to get up. I had no choice; I got up. She saw I was wearing a sexy female nighty and asked, What is this?
I just said my aunt washed all my clothes, and I have nothing to wear, so she gave me this.
She laughed.
And asked me why I was screaming last night. I said I didn't; she was like, No, you sounded like you were enjoying something. I blushed and asked her about my aunt and left.
After a few minutes, Aunt Cane came in, sat on the couch, and raised her skirt.
And asked me to get on my knees and start sucking. I sucked her for a good 20 minutes, and she came in me.
She got up, flipped me, removed my panty, took the dildo out, and started fucking me.
All I could do was moan in pleasure, and I noticed the balcony door was open, and Aiysha could hear me. I told my aunt she didn't care. Aunt was fully dressed while her dick was out, and I was naked with a cage. She cummed deep in me, and as usual, she carried me and walked forward to the balcony while her 13-inch monster was in me.
And sitting on the sofa in the balcony, she started to withdraw her dick and inserted it back and started fucking me harder. I couldn't control my moan. Aiysha heard and came to the balcony to see what was happening, and she saw me being used, and she laughed again and asked my aunt, Can I join? My aunt said, With pleasure, and she came into my apartment, still with a towel, came close to me, and started making jokes and humiliating
Removed her towel She was a goddess, but she too had a dick. It was at least 11 inches but thicker than my aunt's.
Kissed me on my lips while I couldn't kiss her because of the moans; she then stroked her dick and pushed it into my mouth and started fucking.
I was being split-roasted by two angel-looking shemales.
She was still smoking, and she gave it to me to smoke. I looked at Aunt
She said, Go on, I smoke, and I was high as fuck. It was weird.
All I wanted was dick now.
Aiysha already cummed 3 times in me, and my aunt 3 times; my stomach looked bloated with cum, and my aunt handed me to Aiysha and went to wash her dick and started smoking while Aiysha fucked me and cummed in me again and plugged the buttplug after they fucked me. My stomach and intestines were filled with cum.
Said to me to go wash myself; I showered and came out. Aunt handed me a panty to wear and the 3 pink pills. Aiysha saw this and smiled. I drank them and went to sleep.
And the next day when I woke up, my stomach was empty. I was looking a little beautiful, and I didn't care.
Same routine for the next 3 days; Mom was about to come home in 3 days.
Aiysha and Aunt said, Let's go out.
Aunt dressed me in a nice panty, a legging, and a pink top. Makeup was not needed; I was already looking like a female. While going down the elevator, she gave me some to smoke, and I smoked a little more. I couldn't walk properly because I was high. All I can remember is I got into a car, and when I woke up, I was in a hospital. I thought I must have passed out, so they brought me
I felt a weight against my chest; when I looked, I saw 34DD boobs on my chest. I was scared to death. The nurse came in, and with my aunt, I tried to speak, but my voice was different, more girlish. My aunt looked at me and said, You wanted this, so be it.
And wore me a bra and a panty.
Then a legging and a top, we went straight home, and she said, My mom will be back tomorrow evening.
I then realised I was in the hospital for 2 days.
When I walked into my apartment and looked in the mirror, all I saw was a sexy-looking girl with 34DD boobs, a thick ass, and nice, sexy lips with short hair. My aunt came in, gave me 6 different pills, and said I should go to sleep.
I said it's 8:30 in the morning, and I felt dizzy and fell asleep.
Later that night I woke up at 9 by my aunt rubbing my eye and saying I must be ready. I interrupted her and said I was hungry. She said she had proteins first; go take a shower. I took a shower and went to my room, opened my wardrobe, and all my male dresses were gone; everywhere were female dresses. Then my aunt came in and gave me a dark purple lingerie to wear with a stocking and called me out.
I forgot to mention my dick was only 1.5 inches; after the treatment, my ball sack was the size of a grapefruit, so small, no more cage.
I went out and found my aunt waiting, ready.
She started kissing me.
I undid my bra, sucked my nipples, and she undressed and let me suck her nipples, and she made me go down and suck her cock. She came a lot, and before she said she was holding it for 2 days without emptying her balls.
And raped my throat, then turned me around, moved the panty with her fingers, spit right in my arsehole, and inserted her dick slowly, letting me enjoy the feeling that was different.
Fucked me so hard for at least 3 hours straight, my stomach looked like I was 3 months pregnant, and plugged the butt plug back, washed me, gave a kiss, and went to sleep.
When I woke up, it was already 3 pm. I quickly got up, washed my face, dressed, and waited. Aunt entered again. She said to me to remove my top, and she started fucking my boobs while Aiysha joined in. Both fucked me for at least 2 hours. In between fucks, I smoked a little weed. Aiysha pulled a large table, and I was lying on it while Aiysha fucked my ass while Aunt fucked my throat. They came again. Aiysha plugged back in again. my buttplug to stop cum from leaking. They said the more cum I hold in my stomach, the more feminine I become.
I was lying on the table ass up, covered in cum, mouth dripping cum, and suddenly the door opened, and it was my MOM...
To be continued
It felt like it was written by AI, but I enjoyed what little I could understand
I’m guessing English is a second language? A proofreader would help you immensely although it still reads like a “fever dream”. Interesting but strange. BTW, a grapefruit sized ballsack is HUGE!