The story is part of a series. It will make more sense if part one (Caught by My Daughter) is read first.
It had been nearly a week since my daughter Sherri caught me crossdressing. To her credit, she acted like the whole incident never happened. Our day to day interactions and conversations never gave any hint of the accidental discovery or the events that followed. My daughter appeared to be her normal self; the respectful, studious, straight laced girl who would make her parents proud. My wife and I knew she was not a virgin, but we were both satisfied she had learned her lesson. In fact, she had not even dated a guy since she allowed her last boyfriend to take her virginity.
My wife was going to be gone for the weekend visiting her mother. Sherri enjoyed visiting her grandmother and usually went as well. This time, unbeknownst to me, she had other ideas. I got quite a shock when I got home. Sherri met me at the door wearing nylons, heels and a robe.
“What are you doing home? I thought you were going with your mother for the weekend. Why are you dressed like this?” I asked incredulously.
“I told her I didn’t want to go this time. I said I had things I needed to do, but didn’t tell her what.” She replied.
“What things?” I asked.
“Well for one, I want to give you a blow job like I promised I would before Momma almost caught us the other day. Will you dress up like you were again?”
“You mean like Crystal?” I asked.
“Crystal?”
“Yeah, that was the nickname your aunt Mary gave me when she caught me doing it. She was 18 and I was 16 and caught me masturbating like you did. Back then I used to dress up in your grandmother’s clothes. As far as I know Mom never found out, and Mary never said anything.”
“Wow!” Sherri exclaimed. “What did you wear?”
“Let’s go sit down,” I replied. “I will explain it all if you want. It is kind of a long story.”
I related to Sherri that I had started crossdressing very young, in one of Mom’s silky nightgowns, gartered stockings, and an open bottom body briefer, all of which were too big. I ejaculated for the first time just from the feeling and had been hooked ever since. How every time I would cum, and even to this day, I would feel embarrassed about dressing up that way. The first thought in my mind after cumming was always to get rid of the female clothing. Many, many times I had sworn off doing it anymore, but always went back to it like an addiction. I eventually found out how to ‘jack off’ and over time discovered I loved tight girdles, high heels and short skirts. Sometimes I would get hard just thinking about such attire, and it was almost automatic if I saw a lady wearing nylons and heels.
After Mary caught me, she would dress in short skirts, stockings, and high heels when we were home alone. She was always more dominant than I and used to kid me about being her big little brother since she was only 5 foot 4 inches tall and I was 5 foot 10. Just as she does now, she had legs to die for, and wore a 34A bra. She bought thigh high stockings for me and a pair of heels that would fit. Even after she went off to college, she would sometimes send me a package of stockings on my birthday, always preceded by a note a couple of days before that it was coming and that it was ‘for my eyes only’ so I could be on the lookout for the package before anyone else found out about it.
“Wow Daddy,” Sherri commented. “That’s quite a story. I guess I take after Aunt Mary more than I take after Momma since I think it’s hot too. Since she’s not home, will you please dress up like Crystal?”
I agreed to her request and dressed in a silky below the knee nightgown, thigh high stockings, and 4 inch heels.
“Nice!” Sherri exclaimed, seeing me emerge from the bedroom, sporting wood through the nightie. “You walk pretty well in heels. Let’s go back to your bedroom. You lie on your bed so I can suck you off. Just make sure you cum in my mouth.”
To say I was blown away would be an understatement, but I did as she requested. Sherri dropped her robe on the floor and stood before me completely nude. As I lay there admiring her shaved pussy, long legs, and her 34B’s, she deftly pulled my nightie up far enough to gain access to my pulsating member. Taking just the head in her mouth, she began licking, causing me to explode almost immediately.
“Wow Crystal! Do you always cum that quick?” Sherri asked after licking my erection dry.
“I’m sorry,” I muttered “I couldn’t help it. We shouldn’t be doing this. I’m your dad after all.”
“No! Right now you are Crystal,” Sherri retorted. “And now I have a girlfriend with a cock. I want to put it inside me.”
“No. I want you to think about something first.” I told her, thinking a plan I was forming might convince her otherwise. “”If you are going to do that, you are going to do things a little different. From now on, you are not to wear panties when you are home. When you are not home, you will always wear them. If I am home when you get here and your mother is not, you will take them off while I watch you and hand them to me. If you are home when I get here and she is not, you will show me that you are not wearing panties.
It had been nearly a week since my daughter Sherri caught me crossdressing. To her credit, she acted like the whole incident never happened. Our day to day interactions and conversations never gave any hint of the accidental discovery or the events that followed. My daughter appeared to be her normal self; the respectful, studious, straight laced girl who would make her parents proud. My wife and I knew she was not a virgin, but we were both satisfied she had learned her lesson. In fact, she had not even dated a guy since she allowed her last boyfriend to take her virginity.
My wife was going to be gone for the weekend visiting her mother. Sherri enjoyed visiting her grandmother and usually went as well. This time, unbeknownst to me, she had other ideas. I got quite a shock when I got home. Sherri met me at the door wearing nylons, heels and a robe.
“What are you doing home? I thought you were going with your mother for the weekend. Why are you dressed like this?” I asked incredulously.
“I told her I didn’t want to go this time. I said I had things I needed to do, but didn’t tell her what.” She replied.
“What things?” I asked.
“Well for one, I want to give you a blow job like I promised I would before Momma almost caught us the other day. Will you dress up like you were again?”
“You mean like Crystal?” I asked.
“Crystal?”
“Yeah, that was the nickname your aunt Mary gave me when she caught me doing it. She was 18 and I was 16 and caught me masturbating like you did. Back then I used to dress up in your grandmother’s clothes. As far as I know Mom never found out, and Mary never said anything.”
“Wow!” Sherri exclaimed. “What did you wear?”
“Let’s go sit down,” I replied. “I will explain it all if you want. It is kind of a long story.”
I related to Sherri that I had started crossdressing very young, in one of Mom’s silky nightgowns, gartered stockings, and an open bottom body briefer, all of which were too big. I ejaculated for the first time just from the feeling and had been hooked ever since. How every time I would cum, and even to this day, I would feel embarrassed about dressing up that way. The first thought in my mind after cumming was always to get rid of the female clothing. Many, many times I had sworn off doing it anymore, but always went back to it like an addiction. I eventually found out how to ‘jack off’ and over time discovered I loved tight girdles, high heels and short skirts. Sometimes I would get hard just thinking about such attire, and it was almost automatic if I saw a lady wearing nylons and heels.
After Mary caught me, she would dress in short skirts, stockings, and high heels when we were home alone. She was always more dominant than I and used to kid me about being her big little brother since she was only 5 foot 4 inches tall and I was 5 foot 10. Just as she does now, she had legs to die for, and wore a 34A bra. She bought thigh high stockings for me and a pair of heels that would fit. Even after she went off to college, she would sometimes send me a package of stockings on my birthday, always preceded by a note a couple of days before that it was coming and that it was ‘for my eyes only’ so I could be on the lookout for the package before anyone else found out about it.
“Wow Daddy,” Sherri commented. “That’s quite a story. I guess I take after Aunt Mary more than I take after Momma since I think it’s hot too. Since she’s not home, will you please dress up like Crystal?”
I agreed to her request and dressed in a silky below the knee nightgown, thigh high stockings, and 4 inch heels.
“Nice!” Sherri exclaimed, seeing me emerge from the bedroom, sporting wood through the nightie. “You walk pretty well in heels. Let’s go back to your bedroom. You lie on your bed so I can suck you off. Just make sure you cum in my mouth.”
To say I was blown away would be an understatement, but I did as she requested. Sherri dropped her robe on the floor and stood before me completely nude. As I lay there admiring her shaved pussy, long legs, and her 34B’s, she deftly pulled my nightie up far enough to gain access to my pulsating member. Taking just the head in her mouth, she began licking, causing me to explode almost immediately.
“Wow Crystal! Do you always cum that quick?” Sherri asked after licking my erection dry.
“I’m sorry,” I muttered “I couldn’t help it. We shouldn’t be doing this. I’m your dad after all.”
“No! Right now you are Crystal,” Sherri retorted. “And now I have a girlfriend with a cock. I want to put it inside me.”
“No. I want you to think about something first.” I told her, thinking a plan I was forming might convince her otherwise. “”If you are going to do that, you are going to do things a little different. From now on, you are not to wear panties when you are home. When you are not home, you will always wear them. If I am home when you get here and your mother is not, you will take them off while I watch you and hand them to me. If you are home when I get here and she is not, you will show me that you are not wearing panties.
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If your mother ever finds out about it, you will tell her you don’t want to wear panties and never mention anything about our agreement. I don’t have to tell you that nobody must ever find out.”
“I will not put my cock inside you unless and until you agree to this, and I want to think about it until morning before you give me an answer. You will start taking the pill and never refuse to do as I ask, even if you are not in the mood. I am going to take a shower and be your dad for the rest of the night. We will discuss this in the morning.”
Sherri let out a disappointed sigh and retreated to her bedroom. We both changed into ‘proper’ clothes and the rest of the evening we hardly spoke. Whew! I convinced myself I had weirded her out enough that she would not agree to it.
The next morning Sherri was making coffee wearing a calf length, black satin nightgown when I appeared in the kitchen, wearing sweat pants with thigh high nylons underneath. Grinning and gathering the hem above her waist she announced: “See Daddy? I’m not wearing any panties! I want to be your slut and Crystal’s too.”
“I see that pussy is wet,” I commented. “Have you been playing with it?”
“Yes Daddy,” she giggled. “I want your cock inside it. Please?”
“It is mine now,” I informed her. “You are not to play with it, show it to any boys, or share it with anyone else unless I say so. In exchange for that, you may use my cock when your mother is not around. Agreed?”
“Yes Daddy,” she cooed. “And I won’t tell Momma or anyone else either. It will be our secret.”
She stepped toward me with her arms apart as if to give me a hug, then deftly pulled my sweat pants down, revealing my growing erection.
“You are getting a boner already!” Sherri giggled. “Can I have it?”
“Yes, but let’s go to my bedroom,” I replied stepping out of the sweats.
I laid on the bed and watched her take off her nightie. She quickly impaled herself on my pulsing rod and bent over to kiss me.
“Oh Daddy, that feels so good,” Sherri moaned, wiggling on top of me.
“Yes it does, you are going to make me cum,” I panted as my hands roamed her back.
I came quickly and Sherri lay still on top of me until my shrinking member slid out of her.
“If I make you hard again Daddy, will you make me cum?” She asked.
“No. Clean me up with your tongue, then go take a shower and clean yourself up. I will not eat your pussy after I have cum in it.”
As she licked me clean, Sherri commented about how good we tasted together. While she showered, I dressed in an open bottom girdle, gartered stockings, a longline bra, a slip, button down blouse, a skirt, a wig and 4 inch pumps. I was sitting on the sofa in the livingroom looking at a catalogue when she finished.
“Hi Crystal!” Sherri greeted me as I looked up. “I’m not wearing any panties,” she continued as she pulled back her satin robe to show me. “Are you?”
“No, Crystal usually does not wear panties,” I replied. “Take a look for yourself.”
“Nice!” She exclaimed as she pulled up the hem of my skirt. “I see you are hard again.”
“Yes I am. Did you clean all the cum out of your pussy?”
“Yeah, but it is getting wet again.”
“Then stand over me on the couch so I can taste it,” I replied.
Sherri grabbed the backrest on the sofa as I scooted down to feast on her. As I licked, she ground her snatch harder and harder into my face, moaning and gasping.
“Oh Daddy, please stop!” She begged. “I am going to fall down.”
“When I am dressed like this I am Crystal, not your daddy,” I corrected. “Lift up my skirt and sit on my lap facing me so I can make you cum.”
In a flash she had me inside her. As she pleasured herself with my throbbing cock, I massaged her 34B’s. She writhed around and rode me until I came inside her again, causing her to cum as well.
“Oh Crystal, that was great,” she cooed softly as she put her arms around my neck, pressing her lips to mine.
Just then the front door opened.
“What the fuck!” My wife shrieked.
I wanted to die. We were so busted.
“Momma, this is not Daddy’s fault." Sherri explained. “I caught him masturbating dressed up as a girl. You were not supposed to be home until tomorrow, so I made him have sex with me in exchange for not saying anything to you about it.”
“You fucking sick incestuous pervert,” my wife sobbed at me. “You have turned our daughter into a slut! I am fed up with your crossdressing, and now this!”
Still sobbing, my wife slammed the front door and sat on the porch. Sherri and I went to our rooms she quickly dressed and I changed back into male attire.
“Momma, I’m sorry…” Sherri began when my wife came back in the house.
“Sorry for what?” She interrupted. “Did your father put you up to this?”
“No Momma, I wanted to have sex with him when I saw his cock.”
“Get the fuck away from me you bitch!” My wife roared furiously. “I am out of here tomorrow and not coming back! If I find out he has made you pregnant, I will call the cops!”
The rest of the day my wife spent packing her stuff up. I could not even get within five feet of her without her starting to ball her eyes out again. We never spoke another word, and the next morning she was gone.
“I will not put my cock inside you unless and until you agree to this, and I want to think about it until morning before you give me an answer. You will start taking the pill and never refuse to do as I ask, even if you are not in the mood. I am going to take a shower and be your dad for the rest of the night. We will discuss this in the morning.”
Sherri let out a disappointed sigh and retreated to her bedroom. We both changed into ‘proper’ clothes and the rest of the evening we hardly spoke. Whew! I convinced myself I had weirded her out enough that she would not agree to it.
The next morning Sherri was making coffee wearing a calf length, black satin nightgown when I appeared in the kitchen, wearing sweat pants with thigh high nylons underneath. Grinning and gathering the hem above her waist she announced: “See Daddy? I’m not wearing any panties! I want to be your slut and Crystal’s too.”
“I see that pussy is wet,” I commented. “Have you been playing with it?”
“Yes Daddy,” she giggled. “I want your cock inside it. Please?”
“It is mine now,” I informed her. “You are not to play with it, show it to any boys, or share it with anyone else unless I say so. In exchange for that, you may use my cock when your mother is not around. Agreed?”
“Yes Daddy,” she cooed. “And I won’t tell Momma or anyone else either. It will be our secret.”
She stepped toward me with her arms apart as if to give me a hug, then deftly pulled my sweat pants down, revealing my growing erection.
“You are getting a boner already!” Sherri giggled. “Can I have it?”
“Yes, but let’s go to my bedroom,” I replied stepping out of the sweats.
I laid on the bed and watched her take off her nightie. She quickly impaled herself on my pulsing rod and bent over to kiss me.
“Oh Daddy, that feels so good,” Sherri moaned, wiggling on top of me.
“Yes it does, you are going to make me cum,” I panted as my hands roamed her back.
I came quickly and Sherri lay still on top of me until my shrinking member slid out of her.
“If I make you hard again Daddy, will you make me cum?” She asked.
“No. Clean me up with your tongue, then go take a shower and clean yourself up. I will not eat your pussy after I have cum in it.”
As she licked me clean, Sherri commented about how good we tasted together. While she showered, I dressed in an open bottom girdle, gartered stockings, a longline bra, a slip, button down blouse, a skirt, a wig and 4 inch pumps. I was sitting on the sofa in the livingroom looking at a catalogue when she finished.
“Hi Crystal!” Sherri greeted me as I looked up. “I’m not wearing any panties,” she continued as she pulled back her satin robe to show me. “Are you?”
“No, Crystal usually does not wear panties,” I replied. “Take a look for yourself.”
“Nice!” She exclaimed as she pulled up the hem of my skirt. “I see you are hard again.”
“Yes I am. Did you clean all the cum out of your pussy?”
“Yeah, but it is getting wet again.”
“Then stand over me on the couch so I can taste it,” I replied.
Sherri grabbed the backrest on the sofa as I scooted down to feast on her. As I licked, she ground her snatch harder and harder into my face, moaning and gasping.
“Oh Daddy, please stop!” She begged. “I am going to fall down.”
“When I am dressed like this I am Crystal, not your daddy,” I corrected. “Lift up my skirt and sit on my lap facing me so I can make you cum.”
In a flash she had me inside her. As she pleasured herself with my throbbing cock, I massaged her 34B’s. She writhed around and rode me until I came inside her again, causing her to cum as well.
“Oh Crystal, that was great,” she cooed softly as she put her arms around my neck, pressing her lips to mine.
Just then the front door opened.
“What the fuck!” My wife shrieked.
I wanted to die. We were so busted.
“Momma, this is not Daddy’s fault." Sherri explained. “I caught him masturbating dressed up as a girl. You were not supposed to be home until tomorrow, so I made him have sex with me in exchange for not saying anything to you about it.”
“You fucking sick incestuous pervert,” my wife sobbed at me. “You have turned our daughter into a slut! I am fed up with your crossdressing, and now this!”
Still sobbing, my wife slammed the front door and sat on the porch. Sherri and I went to our rooms she quickly dressed and I changed back into male attire.
“Momma, I’m sorry…” Sherri began when my wife came back in the house.
“Sorry for what?” She interrupted. “Did your father put you up to this?”
“No Momma, I wanted to have sex with him when I saw his cock.”
“Get the fuck away from me you bitch!” My wife roared furiously. “I am out of here tomorrow and not coming back! If I find out he has made you pregnant, I will call the cops!”
The rest of the day my wife spent packing her stuff up. I could not even get within five feet of her without her starting to ball her eyes out again. We never spoke another word, and the next morning she was gone.
