Cd crossdresser sissy caught by mom and dad
Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care.
For the last few months I had fucked with my D*d a few times after walking in on him in the shower while crossdressing, he never told my mom for obvious reasons.
A few days ago I was laying on my couch like normal on my laptop watching porn just rubbing my tiny penis. It was pretty late at night, maybe 9:30pm, my parents both worked weird hours where they'd get home around 10:15pm Wearing a black shortsleeve tshirt dress, black lace pushup bra, a black lace thong, garter belt with some stalkings, and some 5 inch black point toe pumps with my buttplug in randomly vibrating.
I was laying there not paying attention to the window that I could see my driveway to see if my parents were coming home. Well about 10 minutes went by and I heard a key go into the back door, right by my living room where i was laying. There was no way I could get to the stairs and up to my room in heels and not be seen. So I was going to get caught for the first time. I prayed real quick it was my dad and not my mom. The door opened, I heard the first step and knew it was my mom. I was about to get caught. My mom shut the door and took about 10 steps into the house and was able to see me, laying there, all dressed up looking like a little crossdresser. She stood there for what seemed like eternity not saying a word, just looking at me. I didn't say anything either, just looked at her. Mid 50s, short hair, nice body, in her dress, 38C boobs, her louboutin heels. She eventually just asked if I was having fun. I responded saying I was and she asked me to stand up and walk over to her so I did. My tiny 4inch penis was rock hard. I had dreamed about getting caught by my mom. She saw I was hard and kinda laughed. She asked me to spin around, so I did. This awkwardness was killing me. Then my buttplug vibrated hard and I couldn't hold in the moan. My mom looked shocked and asked why I moaned, I was silent. It vibrated again by not hard and my mom heard it, turned me around, bent me over and lifted up my dress to see the buttplug. She laughed. Still holding onto me she walked me to her bedroom and told me to get on the bed.What my mom did next I had only dreamed of. She unzippled her dress, and pulled it off. She walked over to her nightstand and opened the second drawer. That's where she kept her sex toys. I knew I was about to have some fun. She said "I suspected you to crossdress but I never thought I'd catch you, or want to do what I'm about to with you. She grabbed her vibrator, a dildo and some lube then hopped on the bed with me.
My mother pulled her bra and panties off. I was in shock and super hard. My buttplug had been on and off vibrating in my asshole for what seemed like forever. The sight of my moms nice tits and shaved pussy had be almost drooling. I wanted to have tits and a pussy like that but also play with hers. "Let's see that little sissy clit under that cute dress" So I slowly pulled my dress us exposing my black lace panties with my hard dick inside. She looked excited saying "those are some cute panties you have there" and pulled them aside letting my little 4 inch dick come out. She stroked it a few times them pushed her hand up under my dress to feel my bra and asked me to take my dress off so I did. She told me she liked my bra and said I could put my dress back on so I did. My mom was rubbing her clit a little bit and asked if I wanted to touch it. I did and loved it. I had never seen another pussy in real life, only porn. My mom told me to turn around and show her my pussy. I rolled over, and turned around and she pulled my panties down so my buttplug was exposed. She pulled it out to see the gaping hole from the plug. "This is nice" she said. I said thank you and she slid two fingers inside my asshole. I jumped not expecting it "Calm down" she said pulling her fingers out. I felt something cold hit my butt, she then rubbed my asshole, it was lube. I felt her lifelike dildo go into my asshole. I loved it! Felt almost like my dad's penis just longer. His penis was only about 6 inches but way thicker than mine. In and out the dildo went. My mom asked if I liked it. I responded yes and she stopped. "Turn around." she said. I turned around and she was fingering herself. Still in her high heels. I always loved her heels, she wore them all the time. I wished they fit on my feet. I went to stroke my dick and she said no. I then heard the backdoor open again. "Your father is never going to believe this" she said. Little did she know. "In the bedroom" she yelled.
My dad walked into the bedroom and here's where things got interesting. He looked shocked when he saw my mother naked and I in the bed. "Look who I found all dressed up" my mother said my father hesitated not knowing if my mother knew him and I were fucking when she wasn't around. He then asked my mother what she was doing and she responded saying we were just having a little fun. My mother then asked my dad if he'd like to join in on the fun. My father, whos 55 and in great shape took his button down shirt off, walked over to the bed, kicked his shoes off and pulled his dress pants and underwear off. My mom crawled across me and gave him a kiss while stroking his cock. She then put my dads dick in her month and sucked on it for probably 30 seconds. She took it out of her mouth, leaned over to me and kissed me, on the lips. The kiss turned into making out and while doing so my dad started to rub his cock. He was getting hard. My mom pulled away. She grabbed the bottle of lube and handed it to my dad, he put some in his hand and rubbed his dick. He had become rock hard. She told me to turn and I was then faced with my ass up towards my dad looking towards my mom. My dad then put one hand on my ass and put his dick in me. I let out a loud moan and my mom had the brightest grin on her face. He started to thrust. My mom grabbed her vibrator and just watched. About 30 seconds later, not touching my dick I exploded cum everywhere. My dad kept thrusting. After about 10 minutes my dad pulled his dick out, my mom went over to him and he exploded in my moms mouth. She then came to me and kissed me. It was the best kiss i ever got. I then fell back and immediately fell asleep still in my heels, bra and dress.
The next morning I woke up. Naked. Neither of my parents were in the bed with me either. I got up and walked to the kitchen where my mom was at the table, in a teddy with stalkings and heels with her legs crossed sipping coffee with a robe on but it was open. It was probably 9:30 in the morning. On the table was a different black dress of mine, but then a pink lace bra with matching panties on the table, and some 6inch platform fake louboutins heels. my mom snickered and pointed at my dick, Which was right hard. I grinned, embarrassed. She then said "so I found your clothes in your dresser and hung them up in your closet since you'll be wearing them when you're at home, no more of your boy clothes. I also went out this morning and bought you more bras and panties since you'll be needing them" I said thank you and she told me to put the clothes on. I did and everything fit perfectly. She then walked to her purse and got out a pink chastity. I asked what that was for and she said "Since you're now your fathers and I sissy, when you're not with either of us you're going to wear this." and handed me the Chasity. "We have a busy day, I went to one store and got you some clothes but that isn't enough so we're going to go to the mall and buy you a wardrobe for when you're home also I called the doctor and told her you've been thinking about becoming a female and would like to start taking hormones to transition so we have an appointment to go to. Lets go fix that little boner of yours and get this chasity on you"
For the last few months I had fucked with my D*d a few times after walking in on him in the shower while crossdressing, he never told my mom for obvious reasons.
A few days ago I was laying on my couch like normal on my laptop watching porn just rubbing my tiny penis. It was pretty late at night, maybe 9:30pm, my parents both worked weird hours where they'd get home around 10:15pm Wearing a black shortsleeve tshirt dress, black lace pushup bra, a black lace thong, garter belt with some stalkings, and some 5 inch black point toe pumps with my buttplug in randomly vibrating.
I was laying there not paying attention to the window that I could see my driveway to see if my parents were coming home. Well about 10 minutes went by and I heard a key go into the back door, right by my living room where i was laying. There was no way I could get to the stairs and up to my room in heels and not be seen. So I was going to get caught for the first time. I prayed real quick it was my dad and not my mom. The door opened, I heard the first step and knew it was my mom. I was about to get caught. My mom shut the door and took about 10 steps into the house and was able to see me, laying there, all dressed up looking like a little crossdresser. She stood there for what seemed like eternity not saying a word, just looking at me. I didn't say anything either, just looked at her. Mid 50s, short hair, nice body, in her dress, 38C boobs, her louboutin heels. She eventually just asked if I was having fun. I responded saying I was and she asked me to stand up and walk over to her so I did. My tiny 4inch penis was rock hard. I had dreamed about getting caught by my mom. She saw I was hard and kinda laughed. She asked me to spin around, so I did. This awkwardness was killing me. Then my buttplug vibrated hard and I couldn't hold in the moan. My mom looked shocked and asked why I moaned, I was silent. It vibrated again by not hard and my mom heard it, turned me around, bent me over and lifted up my dress to see the buttplug. She laughed. Still holding onto me she walked me to her bedroom and told me to get on the bed.What my mom did next I had only dreamed of. She unzippled her dress, and pulled it off. She walked over to her nightstand and opened the second drawer. That's where she kept her sex toys. I knew I was about to have some fun. She said "I suspected you to crossdress but I never thought I'd catch you, or want to do what I'm about to with you. She grabbed her vibrator, a dildo and some lube then hopped on the bed with me.
My mother pulled her bra and panties off. I was in shock and super hard. My buttplug had been on and off vibrating in my asshole for what seemed like forever. The sight of my moms nice tits and shaved pussy had be almost drooling. I wanted to have tits and a pussy like that but also play with hers. "Let's see that little sissy clit under that cute dress" So I slowly pulled my dress us exposing my black lace panties with my hard dick inside. She looked excited saying "those are some cute panties you have there" and pulled them aside letting my little 4 inch dick come out. She stroked it a few times them pushed her hand up under my dress to feel my bra and asked me to take my dress off so I did. She told me she liked my bra and said I could put my dress back on so I did. My mom was rubbing her clit a little bit and asked if I wanted to touch it. I did and loved it. I had never seen another pussy in real life, only porn. My mom told me to turn around and show her my pussy. I rolled over, and turned around and she pulled my panties down so my buttplug was exposed. She pulled it out to see the gaping hole from the plug. "This is nice" she said. I said thank you and she slid two fingers inside my asshole. I jumped not expecting it "Calm down" she said pulling her fingers out. I felt something cold hit my butt, she then rubbed my asshole, it was lube. I felt her lifelike dildo go into my asshole. I loved it! Felt almost like my dad's penis just longer. His penis was only about 6 inches but way thicker than mine. In and out the dildo went. My mom asked if I liked it. I responded yes and she stopped. "Turn around." she said. I turned around and she was fingering herself. Still in her high heels. I always loved her heels, she wore them all the time. I wished they fit on my feet. I went to stroke my dick and she said no. I then heard the backdoor open again. "Your father is never going to believe this" she said. Little did she know. "In the bedroom" she yelled.
My dad walked into the bedroom and here's where things got interesting. He looked shocked when he saw my mother naked and I in the bed. "Look who I found all dressed up" my mother said my father hesitated not knowing if my mother knew him and I were fucking when she wasn't around. He then asked my mother what she was doing and she responded saying we were just having a little fun. My mother then asked my dad if he'd like to join in on the fun. My father, whos 55 and in great shape took his button down shirt off, walked over to the bed, kicked his shoes off and pulled his dress pants and underwear off. My mom crawled across me and gave him a kiss while stroking his cock. She then put my dads dick in her month and sucked on it for probably 30 seconds. She took it out of her mouth, leaned over to me and kissed me, on the lips. The kiss turned into making out and while doing so my dad started to rub his cock. He was getting hard. My mom pulled away. She grabbed the bottle of lube and handed it to my dad, he put some in his hand and rubbed his dick. He had become rock hard. She told me to turn and I was then faced with my ass up towards my dad looking towards my mom. My dad then put one hand on my ass and put his dick in me. I let out a loud moan and my mom had the brightest grin on her face. He started to thrust. My mom grabbed her vibrator and just watched. About 30 seconds later, not touching my dick I exploded cum everywhere. My dad kept thrusting. After about 10 minutes my dad pulled his dick out, my mom went over to him and he exploded in my moms mouth. She then came to me and kissed me. It was the best kiss i ever got. I then fell back and immediately fell asleep still in my heels, bra and dress.
The next morning I woke up. Naked. Neither of my parents were in the bed with me either. I got up and walked to the kitchen where my mom was at the table, in a teddy with stalkings and heels with her legs crossed sipping coffee with a robe on but it was open. It was probably 9:30 in the morning. On the table was a different black dress of mine, but then a pink lace bra with matching panties on the table, and some 6inch platform fake louboutins heels. my mom snickered and pointed at my dick, Which was right hard. I grinned, embarrassed. She then said "so I found your clothes in your dresser and hung them up in your closet since you'll be wearing them when you're at home, no more of your boy clothes. I also went out this morning and bought you more bras and panties since you'll be needing them" I said thank you and she told me to put the clothes on. I did and everything fit perfectly. She then walked to her purse and got out a pink chastity. I asked what that was for and she said "Since you're now your fathers and I sissy, when you're not with either of us you're going to wear this." and handed me the Chasity. "We have a busy day, I went to one store and got you some clothes but that isn't enough so we're going to go to the mall and buy you a wardrobe for when you're home also I called the doctor and told her you've been thinking about becoming a female and would like to start taking hormones to transition so we have an appointment to go to. Lets go fix that little boner of yours and get this chasity on you"
7年前
