When Amy was elected to the supreme court and made some decisions I did not agree with I thought I would go visit her in Virginia and have a few words. I did not realize just how strong and powerful she really is. She also has a radar for weak men and can dominate them before they even know what happened.
I was standing outside of her house when she approached me. She asked what I was doing there and I started to tell her. Her eyes bored into me and I lost all of my resolve. I started stammering and she told me to come inside. Her house is gigantic probably 8000 sq ft. She sat me on the couch and said “I know your type. Whiney babies that miss their mommies. Am I right?”
“Stay right there I’m going to do a test to see if I am right”. She walked out of the room leaving me on the couch. I started to feel like this was a big mistake but I was too frightened to do anything. She came back into the living room holding 2 adult sized diapers. One was pink and the other blue. “So, which is it going to be? A pink little girl sissy or a baby boy?” I instantly felt weak and powerless. “Well? Do want me to dress you like a sissy or a little boy?”
I was standing outside of her house when she approached me. She asked what I was doing there and I started to tell her. Her eyes bored into me and I lost all of my resolve. I started stammering and she told me to come inside. Her house is gigantic probably 8000 sq ft. She sat me on the couch and said “I know your type. Whiney babies that miss their mommies. Am I right?”
“Stay right there I’m going to do a test to see if I am right”. She walked out of the room leaving me on the couch. I started to feel like this was a big mistake but I was too frightened to do anything. She came back into the living room holding 2 adult sized diapers. One was pink and the other blue. “So, which is it going to be? A pink little girl sissy or a baby boy?” I instantly felt weak and powerless. “Well? Do want me to dress you like a sissy or a little boy?”
I had a tent in my trousers. I felt helpless and murmured “A sissy”. “What did you say?” I told her sissy. “Ha! I thought so. You sissies are so easy to predict. I need a little sissy right now so this is perfect. My breasts are full of milk and I keep them that way by pumping them 5 times a day. You can be my little sissy baby and nurse me instead when I am home. Would you like that little sissy?” She took no time at all to make me feel humiliated. She knew exactly how to control me. I told her yes I will be your little sissy. Somehow She turned everything around and I suddenly lost all control and loved it.
“Great! Let’s get you diapered and changed.” How did this happen so quickly? Apparently I must not have been her first sissy. She brought me to a nursery all in pink. Here is a cute little pink dress for you. Take your clothes off and I’ll put your diaper on. I stripped naked and stood in front over her trying to hide my growing erection. She laughed at me and told me to move my hands away. A big smile spread across her face as she looked down at my small erect penis. “My my what a little girl you are. It looks like someone is enjoying this.” I laid on the ground and she wrapped the diaper around me and taped it shut. She made sure there was room for me to reach inside of the diaper because she knows how much little sissies like to play with themselves.
We went back in the living room and she motioned for me to put my head in her lap and lay on the couch. She unbuttoned her blouse and removed one of her breasts from her bra. It was large and very full looking. She lowered her nipple to my mouth and I instinctively started to suckle her breast. Warm milk started flowing into my mouth immediately. I felt like this was always meant to be. She cooed at me as she looked down at me. “There, there sissy girl, enjoy mommy’s milk.” I nursed for 20 minutes before she moved me to her other breast. The feeling of her warm breast and being cradled in her lap was over powering and made me so weak.
Suddenly I felt like I had to pee and all of the suddenly without warning I started wetting my diaper. I couldn’t understand how it was happening but it felt so good. I was helpless nursing mommy and wetting my sissy diaper. Amy noticed the sound and asked me if I was wetting myself. I nodded yes as I suckled her full breast. “Good girl! That’s it let yourself go into that pink sissy diaper. That’s what it for.” I relaxed my bladder entirely and flooded my diaper. I could feel the warn liquid surrounding me. She reached down and placed her hand on my now warm and expanding diaper. “Oh that’s a lot of pee for a little girl.” She started rubbing and massaging the diaper around my crotch. I couldn’t control myself as I started thrusting my hips towards her hand.
“Is the little sissy excited” she laughed. I started making little squealing noises as I felt an orgasm coming on. “Well you certainly do not last long! Go ahead and make another mess in your diaper sissy girl.” I started spurting into my diaper uncontrollably as I still suckled her breast. I can’t believe I came so fast. I was completely humiliated but didn’t care. “Don’t worry sissy I’ll change you once all of your messes are done.”
A week later I was living in the nursery and nursing on Amy at least 3 times a day. I looked so forward to mommy coming home and letting me suckle on her warm full firm breasts. It was heaven and I would do anything for my mommy. I was allowed to play with myself when ever I wanted to. Usually while nursing I would slide my hand into my diapers and quickly ejaculate. I had become a premature ejaculator as well as a sissy.
Amy’s husband Jesse was away on business and would be home next week. I was scared of what was going to happen when he did. I loved my new mommy and didn’t want to leave. We were on the couch and Amy’s nipple was in my mouth as Amy said “You know Jesse has been out of town and well I have needs and would like you to help me with them” I couldn’t believe it and started trying to take off my diaper. “What are you doing silly?” she started laughing. “You couldn’t possibly please me with that little sissy stick of yours! You can’t satisfy a woman silly girl”. I was ashamed as I looked up at her. “It’s ok sweetie, I want to teach you how to lick my pussy” I instantly slid my hand in my diaper and started playing with myself. “Yes please mommy I want to learn that”. “Very well. Let’s get started”.
I finished nursing and she had me kneel in front of her in my crinkly diaper. She hiked up her business skirt and pulled down her white lace panties. Amy has a very hairy pussy. She spread her legs and motioned for me to move forward “Ok honey slowly part my hair and touch my lips with your tongue”.
She smelled earthy and musky. It was intoxicating as my tongue buried into her pubic hair and came in contact with her wet pussy lips. She tasted wonderful. “Now slowly lick up and down my slit going a little deeper with your tongue each time” I did as she instructed and was rewarded with her pussy getting moister. This went on for a while but apparently I was not doing such a good job “Oh little sissy you just can’t please a woman can you? That’s ok we can keep trying to teach you. However mommy needs some relief so I am going to get a little rough with you face sissy. Stick out your tongue” She grabbed the sides of my head and pulled my deep into her pussy, arching her hips upward. She started gyrating on my face using my nose to stimulate her pussy and my tongue to stimulate her asshole.
My face was getting drenched with her juices as she used me to reach orgasm. I just went limp and let her ride and guide my face however she wanted. “Oh sissy I’m going to come all over your face!” and she started gushing on my face. I could feel her pussy contracting and pushing her cum out as it dripped down my chin and chest. Eventually she was finished with me and pushed my face away as rivulets of her cum stuck to my face and then snapped. I felt totally used and helpless but also euphoric that I was so close to her pussy. I wanted to be her toy. “Thank you mommy!” I cried out. “You’re welcome sweetheart”.
As it got closer to Jesse coming home, Amy told me she wanted to have me dressed special for Jesse so that I could impress him. I was very nervous about meeting him. Amy found a beautiful frilly pink dress for me to wear. She taught me how to curtsey and pirouette so that I can impress Jesse. She told me just this time I was going to wear pink panties and not my diaper but warned me not to make a mess in my panties. Finally the day came and Jesse pulled into the garage. Amy told me to wait in the living room while she greeted Jesse.
“I have someone I want you to meet” I heard her say and in they walked into the living room. I curtseyed in my short little pink dress. They both burst out laughing at me and I turned red with embarrassment. “What the hell is that?” Jess exclaimed. “Its my new sissy. She keeps me company when you’re not home and nurses my breasts so I can keep my milk flowing”. I was so embarrassed and started to feel my little penis getting hard. I felt like I wanted to wet my panties. I lifted my skirt showing them my little stiff tent in my panties and said “Mommy I need to pee” and a little wet spot start to form. “Oh no! I took off her diaper because I wanted you to see her in her little pink panties. Hurry sissy lets get you back in your diaper.” Jesse just shook his head as Amy hurried me into the nursery.
My panties were pretty wet by the time she peeled them off of me. “Poor sissy I was afraid you might wet yourself without a diaper”. “I feel so ashamed mommy I’m sorry” I told her as she lay me on top of the diaper. My little penis was so stiff from the humiliation. She taped me up in the diaper and said “Go ahead and play with yourself sissy I know all this makes you want to make some messes. Jesse and I have some catching up to do so you stay here and I’ll see you in the morning”.
I put my hand in my diaper and started playing with myself. In no time at all I heard Amy moaning. They were having sex right on the couch. Soon she was screaming “Fuck me. Fuck me” as I could hear Jesse’s balls smacking into her pussy as he pounded her. “Oh yes you’re soo huge! Fill me up please! I want to feel your cum deep inside me!” They made no attempt to be quiet as I quickly filled my diaper with cum. Jesse was impressive. I could never ever satisfy a woman like that. Not even close.
Amy was on the couch nursing me the next morning when Jesse came down. He looked at me with her breast in my mouth and my full diapers from the night before. “Hi honey. Just nursing the sissy before I go to work”. Jesse leaned over and gave her a kiss as her hand rested on the crotch of my diapers. I started thrusting my hips and Jesse looked and shook his head and laughed. “She gets this way when I nurse her. Don’t worry she wont last long” and sure enough I grunted and splashed into my diaper as she absent mindedly rubbed my crotch. Amy giggled and kissed the top of my head. “There, there sissy everything is ok now”.
That evening while laying on the couch being nursed, Amy told me she wanted me to try to please her again before Jesse got home. “I am very wet thinking about Jesse taking me tonight. I need a little relief before he gets home.” Once again I slid to me knees as she removed her panties and parted her legs for me. I dove in like she taught me and start licking her pussy as best I could. She put her hand on my head and guided my mouth around her pussy as I kept licking. She gets very wet very quickly. She leaned her head back as I serviced her as best I could. She sighed saying “You’re such a sissy. You just can’t seem to please me but that’s ok keep going it just makes me long for Jesse even more”. I heard the garage door open and lifted up my head but she just pushed me back down to her pussy.
Jesse walked in and saw me on my knees trying to please his wife. I’m far from a threat in my pink dress and diaper so Jesse felt no jealously. He sat down next to Amy and started kissing her while I kept busy licking her wet pussy. “Oh Jesse, take me right now! Please!” she said as she pushed me out from between her legs. “My pleasure” Jesse replied. I just sat on the ground at their feet as Jesse pulled off his pants and underwear. I gasped at the size of his enormous cock and it wasn’t even fully hard. They ignored me as Amy started stroking him as she kissed him. His cock grew to 9” at least and was so thick around. Amy sighed and brought her mouth over its head and made eye contact with me. I put my hand in my diaper and started playing with myself as Amy smiled around his huge cock in her mouth. Next Amy stood up and straddled his rock hard erection and lowered her dripping pussy on to it. I had a front row seat as he went balls deep.
She threw her head back and screamed with passion “Yes oh yes. I love your cock inside me!” Jesse picked her up with his cock still inside and laid her on the couch and started fucking her in earnest. I felt such privilege to be allowed to witness them. Jesse was truly a master cocksman. I could never do what he did. I always cum too fast so I slowed down stroking my little cock. I was mesmerized. I could see his cock pounding in and out of her pussy, it was covered in her juices as it slid almost the entire way out and then all the way back until you heard his big balls slapping against her. It was amazing to see. He picked up his tempo and I realized soon he was going to empty his huge balls deep into her pussy. Amy sensed this too and started begging for his cum. “Fill my little pussy up! I want to feel your hot cum splashing inside of me!” With a final grunt Jesse thrust as deeply as it could go. I watched his big balls start pulsing as gallons of cum must be splashing into Amy’s warm womb. She spread her legs wider and thrust herself upwards to bring him deeper inside of her.
When Jesse finally pulled out her pussy was a mess. All her thick pussy hair was matted down with their juices. I could see his sperm drooling out of her now gapping pussy. Amy was in total bliss as she looked over at me. “Come here sissy and clean me up. Its time you tasted Jesse’s cum” With my hand still in my diaper I too spurt cum, not nearly as much as Jesse, but those words brought me over the edge. All I wanted was to clean her pussy. Amy was lying on the couch with her legs wide apart. I laid down on the couch on my stomach between her legs staring at her messy well fucked pussy. I dove in and started licking up everything I could. Amy put her hands behind her head and stared up at the ceiling with a starry eyed look. I was scooping out Jesse’s cum from inside her pussy with my tongue. Glob after glob. “How do you like the taste of Jesse sissy girl?” she asked me. “I love it! Thank you so much” came my muffled reply.
Jesse had to go on another business trip. As I was being nursed Amy said “I want to surprise Jesse when he gets home. It’s time to give yourself to Jesse”. I looked up at mommy with fear in my eyes, “But mommy I’m scared. He’s so big”. “I know sissy. We’ll work you up to it and I’ll be with you the whole time.” She comforted. She came back from the nursery with 3 dildos. Each one bigger than the other. These will help you to be able to accommodate Jesse. I whimpered with fear and hugged mommy “I’m afraid mommy”. “It’s ok sweetie and besides “ as she reached down to my hard little sissy cock poking inside my diaper “It would appear that you might actually like the idea” “Oh mommy I love you”.
The first night I took off my diaper and laid across mommy’s lap. She pinned my little cock in between her bare legs. Now we will start with the smallest one. She took a finger full of Vaseline and stuck it in my asshole. Slowly she pumped her finger in and out of my asshole as I squirmed and squealed like a little girl. “There now sweatheart doesn’t that feel good?” At first it was invasive but after a little while it started to feel good. Real good. Next she picked up the 5” black dildo and started to rub it against my rosebud. “Ok sweetie I will do this slowly”. The dildo slipped in and I groaned. “Here we go!” she giggled and started gently thrusting the small dildo in and out of my ass. It was painful at first but like with her finger ts started to feel wonderful. Soon I was thrusting back with my bare ass across her lap. She cooed at me telling me how proud she is of me. Then after a while I felt a climax building up. “Oh mommy I’m going to squirt!”. “Good girl! That’s what sissy’s do when they are getting fucked in their ass” That was too much and I spurted in between her legs. “Oh my there she goes” mommy laughed as I spent myself. “Why don’t you clean mommy’s legs with your tongue and then we’ll get you back in your diapers. Then tomorrow night we’ll try the next size.
By the last night I was taking a 9” dildo in my little sissy girl ass. I was getting quite used to it and I would cum from just that. Mommy even fucked me standing up in front of her so she could watch my little cock shoots its goo. She clapped her hands as she left the 9” cock buried in my ass, watching my twitching little cock bob up and down as I squirted sperm. “That’s it little sissy girl! Jesse is going to have fun with you” I was ready for Jesse or at least I hoped I was. I just wanted to make mommy happy. Giving Jesse my virgin sissy ass was the least I could do. “Thank you mommy I want to make Jesse happy and be his sissy bitch!”. “That’s such a good sissy” she said with a big smile.
Once again mommy dressed me in a short little pink fairy girl dress and had me wear pink panties instead of diapers for Jesse’s arrival home. I was so nervous. Mommy didn’t let me play with myself for 3 days just so Jesse could see me squirt. “Now sweetie you can’t have any accidents in your panties this time. I’m trusting you to not be in diapers for the evening.” “Yes mommy I will be a good little sissy girl” Jesse arrived home that evening and I was waiting for him in the living room. “Oh Jesse! our little sissy has something special for you” Amy teased. My little cock was so hard in my pink panties. Jesse walked in and I curtsied. “Sissy wants to give you her virgin ass tonight. We’ve been training her all week. Isn’t that right sissy?” “Yes mommy. I want daddy to take me tonight anyway he wants” I said in my sweetest girly voice.
“Well now this is a surprise.” Jesse said. “Are you sure she is up for it” he asked Amy. “Oh yes dear we have been prepping her every night.” “Ok then take off those panties and come over here” Jesse commanded. I removed my pink panties and my tiny penis shot straight out. I’ve never been harder. They both laughed out loud at how hard and how small I was. Jesse got his pants off and told me to kneel before him. I did as I was told. He presented me with his semihard member and I greedily held it in my hands as it started to grow. “Put in your mouth and suck on it” he said. I could barley fit the head in my mouth as I felt it grow in my hands. I started to get nervous because it was definitely bigger then the 9” dildo I had been practicing with and thicker. I worked on his cock until it was rock hard. I don’t think Jesse every plays with himself so this was more than a week of pent up sperm waiting to come out. His balls here like softballs in my hands.
“Ok sissy are you ready?” Jesse asked. I got really nervous and looked over at mommy “Please be with me mommy. Come hug me!” “Of course sweet heart” she said as she grabbed the lubricant, and told me to bend over. She put a big dollup of Vaseline up my asshole and rubbed it all around. She sat on the couch and told me to put my head in her lap and bend over. She started stroking my hair and whispering in my ear that everything will be alright. I felt Jesse’s hands on my hips and braced myself for what was about to come. Jesse and Amy looked at each other and smiled as he positioned himself at the entrance to my asshole. “What would you like to tell Jesse sissy girl?” Amy asked me. “Oh please take me. Take my virgin ass. I belong to you. I want to be your sissy bitch!” I cried out as Jesse pushed his massive pulsing cock into my little virgin ass.
I cried out in a little girl voice. It felt like I was being torn in two. He was so huge. I looked into mommy’s face as tears come to my eyes. She caressed my face and kissed me. “Our little sissy. Just give in an accept your sissy fate”. I did and soon I was so full of his cock that it no longer hurt. He was thrusting into me as my legs started to quiver and I felt so weak. He held me up and kept thrusting himself into me. I was squealing and pleading like a little girl. I shook so much as an orgasm washed over me. My tiny cock sent streams of girly cum flying. It was splashing on Amy’s bare legs as she watched. She bent my head down so I could lick up the cum while Jesse relentlessly pounded me. He finally filled my no longer virgin ass full of his cum. I could feel it inside of me. I wanted to be their sissy girl forever.
“Great! Let’s get you diapered and changed.” How did this happen so quickly? Apparently I must not have been her first sissy. She brought me to a nursery all in pink. Here is a cute little pink dress for you. Take your clothes off and I’ll put your diaper on. I stripped naked and stood in front over her trying to hide my growing erection. She laughed at me and told me to move my hands away. A big smile spread across her face as she looked down at my small erect penis. “My my what a little girl you are. It looks like someone is enjoying this.” I laid on the ground and she wrapped the diaper around me and taped it shut. She made sure there was room for me to reach inside of the diaper because she knows how much little sissies like to play with themselves.
We went back in the living room and she motioned for me to put my head in her lap and lay on the couch. She unbuttoned her blouse and removed one of her breasts from her bra. It was large and very full looking. She lowered her nipple to my mouth and I instinctively started to suckle her breast. Warm milk started flowing into my mouth immediately. I felt like this was always meant to be. She cooed at me as she looked down at me. “There, there sissy girl, enjoy mommy’s milk.” I nursed for 20 minutes before she moved me to her other breast. The feeling of her warm breast and being cradled in her lap was over powering and made me so weak.
Suddenly I felt like I had to pee and all of the suddenly without warning I started wetting my diaper. I couldn’t understand how it was happening but it felt so good. I was helpless nursing mommy and wetting my sissy diaper. Amy noticed the sound and asked me if I was wetting myself. I nodded yes as I suckled her full breast. “Good girl! That’s it let yourself go into that pink sissy diaper. That’s what it for.” I relaxed my bladder entirely and flooded my diaper. I could feel the warn liquid surrounding me. She reached down and placed her hand on my now warm and expanding diaper. “Oh that’s a lot of pee for a little girl.” She started rubbing and massaging the diaper around my crotch. I couldn’t control myself as I started thrusting my hips towards her hand.
“Is the little sissy excited” she laughed. I started making little squealing noises as I felt an orgasm coming on. “Well you certainly do not last long! Go ahead and make another mess in your diaper sissy girl.” I started spurting into my diaper uncontrollably as I still suckled her breast. I can’t believe I came so fast. I was completely humiliated but didn’t care. “Don’t worry sissy I’ll change you once all of your messes are done.”
A week later I was living in the nursery and nursing on Amy at least 3 times a day. I looked so forward to mommy coming home and letting me suckle on her warm full firm breasts. It was heaven and I would do anything for my mommy. I was allowed to play with myself when ever I wanted to. Usually while nursing I would slide my hand into my diapers and quickly ejaculate. I had become a premature ejaculator as well as a sissy.
Amy’s husband Jesse was away on business and would be home next week. I was scared of what was going to happen when he did. I loved my new mommy and didn’t want to leave. We were on the couch and Amy’s nipple was in my mouth as Amy said “You know Jesse has been out of town and well I have needs and would like you to help me with them” I couldn’t believe it and started trying to take off my diaper. “What are you doing silly?” she started laughing. “You couldn’t possibly please me with that little sissy stick of yours! You can’t satisfy a woman silly girl”. I was ashamed as I looked up at her. “It’s ok sweetie, I want to teach you how to lick my pussy” I instantly slid my hand in my diaper and started playing with myself. “Yes please mommy I want to learn that”. “Very well. Let’s get started”.
I finished nursing and she had me kneel in front of her in my crinkly diaper. She hiked up her business skirt and pulled down her white lace panties. Amy has a very hairy pussy. She spread her legs and motioned for me to move forward “Ok honey slowly part my hair and touch my lips with your tongue”.
She smelled earthy and musky. It was intoxicating as my tongue buried into her pubic hair and came in contact with her wet pussy lips. She tasted wonderful. “Now slowly lick up and down my slit going a little deeper with your tongue each time” I did as she instructed and was rewarded with her pussy getting moister. This went on for a while but apparently I was not doing such a good job “Oh little sissy you just can’t please a woman can you? That’s ok we can keep trying to teach you. However mommy needs some relief so I am going to get a little rough with you face sissy. Stick out your tongue” She grabbed the sides of my head and pulled my deep into her pussy, arching her hips upward. She started gyrating on my face using my nose to stimulate her pussy and my tongue to stimulate her asshole.
My face was getting drenched with her juices as she used me to reach orgasm. I just went limp and let her ride and guide my face however she wanted. “Oh sissy I’m going to come all over your face!” and she started gushing on my face. I could feel her pussy contracting and pushing her cum out as it dripped down my chin and chest. Eventually she was finished with me and pushed my face away as rivulets of her cum stuck to my face and then snapped. I felt totally used and helpless but also euphoric that I was so close to her pussy. I wanted to be her toy. “Thank you mommy!” I cried out. “You’re welcome sweetheart”.
As it got closer to Jesse coming home, Amy told me she wanted to have me dressed special for Jesse so that I could impress him. I was very nervous about meeting him. Amy found a beautiful frilly pink dress for me to wear. She taught me how to curtsey and pirouette so that I can impress Jesse. She told me just this time I was going to wear pink panties and not my diaper but warned me not to make a mess in my panties. Finally the day came and Jesse pulled into the garage. Amy told me to wait in the living room while she greeted Jesse.
“I have someone I want you to meet” I heard her say and in they walked into the living room. I curtseyed in my short little pink dress. They both burst out laughing at me and I turned red with embarrassment. “What the hell is that?” Jess exclaimed. “Its my new sissy. She keeps me company when you’re not home and nurses my breasts so I can keep my milk flowing”. I was so embarrassed and started to feel my little penis getting hard. I felt like I wanted to wet my panties. I lifted my skirt showing them my little stiff tent in my panties and said “Mommy I need to pee” and a little wet spot start to form. “Oh no! I took off her diaper because I wanted you to see her in her little pink panties. Hurry sissy lets get you back in your diaper.” Jesse just shook his head as Amy hurried me into the nursery.
My panties were pretty wet by the time she peeled them off of me. “Poor sissy I was afraid you might wet yourself without a diaper”. “I feel so ashamed mommy I’m sorry” I told her as she lay me on top of the diaper. My little penis was so stiff from the humiliation. She taped me up in the diaper and said “Go ahead and play with yourself sissy I know all this makes you want to make some messes. Jesse and I have some catching up to do so you stay here and I’ll see you in the morning”.
I put my hand in my diaper and started playing with myself. In no time at all I heard Amy moaning. They were having sex right on the couch. Soon she was screaming “Fuck me. Fuck me” as I could hear Jesse’s balls smacking into her pussy as he pounded her. “Oh yes you’re soo huge! Fill me up please! I want to feel your cum deep inside me!” They made no attempt to be quiet as I quickly filled my diaper with cum. Jesse was impressive. I could never ever satisfy a woman like that. Not even close.
Amy was on the couch nursing me the next morning when Jesse came down. He looked at me with her breast in my mouth and my full diapers from the night before. “Hi honey. Just nursing the sissy before I go to work”. Jesse leaned over and gave her a kiss as her hand rested on the crotch of my diapers. I started thrusting my hips and Jesse looked and shook his head and laughed. “She gets this way when I nurse her. Don’t worry she wont last long” and sure enough I grunted and splashed into my diaper as she absent mindedly rubbed my crotch. Amy giggled and kissed the top of my head. “There, there sissy everything is ok now”.
That evening while laying on the couch being nursed, Amy told me she wanted me to try to please her again before Jesse got home. “I am very wet thinking about Jesse taking me tonight. I need a little relief before he gets home.” Once again I slid to me knees as she removed her panties and parted her legs for me. I dove in like she taught me and start licking her pussy as best I could. She put her hand on my head and guided my mouth around her pussy as I kept licking. She gets very wet very quickly. She leaned her head back as I serviced her as best I could. She sighed saying “You’re such a sissy. You just can’t seem to please me but that’s ok keep going it just makes me long for Jesse even more”. I heard the garage door open and lifted up my head but she just pushed me back down to her pussy.
Jesse walked in and saw me on my knees trying to please his wife. I’m far from a threat in my pink dress and diaper so Jesse felt no jealously. He sat down next to Amy and started kissing her while I kept busy licking her wet pussy. “Oh Jesse, take me right now! Please!” she said as she pushed me out from between her legs. “My pleasure” Jesse replied. I just sat on the ground at their feet as Jesse pulled off his pants and underwear. I gasped at the size of his enormous cock and it wasn’t even fully hard. They ignored me as Amy started stroking him as she kissed him. His cock grew to 9” at least and was so thick around. Amy sighed and brought her mouth over its head and made eye contact with me. I put my hand in my diaper and started playing with myself as Amy smiled around his huge cock in her mouth. Next Amy stood up and straddled his rock hard erection and lowered her dripping pussy on to it. I had a front row seat as he went balls deep.
She threw her head back and screamed with passion “Yes oh yes. I love your cock inside me!” Jesse picked her up with his cock still inside and laid her on the couch and started fucking her in earnest. I felt such privilege to be allowed to witness them. Jesse was truly a master cocksman. I could never do what he did. I always cum too fast so I slowed down stroking my little cock. I was mesmerized. I could see his cock pounding in and out of her pussy, it was covered in her juices as it slid almost the entire way out and then all the way back until you heard his big balls slapping against her. It was amazing to see. He picked up his tempo and I realized soon he was going to empty his huge balls deep into her pussy. Amy sensed this too and started begging for his cum. “Fill my little pussy up! I want to feel your hot cum splashing inside of me!” With a final grunt Jesse thrust as deeply as it could go. I watched his big balls start pulsing as gallons of cum must be splashing into Amy’s warm womb. She spread her legs wider and thrust herself upwards to bring him deeper inside of her.
When Jesse finally pulled out her pussy was a mess. All her thick pussy hair was matted down with their juices. I could see his sperm drooling out of her now gapping pussy. Amy was in total bliss as she looked over at me. “Come here sissy and clean me up. Its time you tasted Jesse’s cum” With my hand still in my diaper I too spurt cum, not nearly as much as Jesse, but those words brought me over the edge. All I wanted was to clean her pussy. Amy was lying on the couch with her legs wide apart. I laid down on the couch on my stomach between her legs staring at her messy well fucked pussy. I dove in and started licking up everything I could. Amy put her hands behind her head and stared up at the ceiling with a starry eyed look. I was scooping out Jesse’s cum from inside her pussy with my tongue. Glob after glob. “How do you like the taste of Jesse sissy girl?” she asked me. “I love it! Thank you so much” came my muffled reply.
Jesse had to go on another business trip. As I was being nursed Amy said “I want to surprise Jesse when he gets home. It’s time to give yourself to Jesse”. I looked up at mommy with fear in my eyes, “But mommy I’m scared. He’s so big”. “I know sissy. We’ll work you up to it and I’ll be with you the whole time.” She comforted. She came back from the nursery with 3 dildos. Each one bigger than the other. These will help you to be able to accommodate Jesse. I whimpered with fear and hugged mommy “I’m afraid mommy”. “It’s ok sweetie and besides “ as she reached down to my hard little sissy cock poking inside my diaper “It would appear that you might actually like the idea” “Oh mommy I love you”.
The first night I took off my diaper and laid across mommy’s lap. She pinned my little cock in between her bare legs. Now we will start with the smallest one. She took a finger full of Vaseline and stuck it in my asshole. Slowly she pumped her finger in and out of my asshole as I squirmed and squealed like a little girl. “There now sweatheart doesn’t that feel good?” At first it was invasive but after a little while it started to feel good. Real good. Next she picked up the 5” black dildo and started to rub it against my rosebud. “Ok sweetie I will do this slowly”. The dildo slipped in and I groaned. “Here we go!” she giggled and started gently thrusting the small dildo in and out of my ass. It was painful at first but like with her finger ts started to feel wonderful. Soon I was thrusting back with my bare ass across her lap. She cooed at me telling me how proud she is of me. Then after a while I felt a climax building up. “Oh mommy I’m going to squirt!”. “Good girl! That’s what sissy’s do when they are getting fucked in their ass” That was too much and I spurted in between her legs. “Oh my there she goes” mommy laughed as I spent myself. “Why don’t you clean mommy’s legs with your tongue and then we’ll get you back in your diapers. Then tomorrow night we’ll try the next size.
By the last night I was taking a 9” dildo in my little sissy girl ass. I was getting quite used to it and I would cum from just that. Mommy even fucked me standing up in front of her so she could watch my little cock shoots its goo. She clapped her hands as she left the 9” cock buried in my ass, watching my twitching little cock bob up and down as I squirted sperm. “That’s it little sissy girl! Jesse is going to have fun with you” I was ready for Jesse or at least I hoped I was. I just wanted to make mommy happy. Giving Jesse my virgin sissy ass was the least I could do. “Thank you mommy I want to make Jesse happy and be his sissy bitch!”. “That’s such a good sissy” she said with a big smile.
Once again mommy dressed me in a short little pink fairy girl dress and had me wear pink panties instead of diapers for Jesse’s arrival home. I was so nervous. Mommy didn’t let me play with myself for 3 days just so Jesse could see me squirt. “Now sweetie you can’t have any accidents in your panties this time. I’m trusting you to not be in diapers for the evening.” “Yes mommy I will be a good little sissy girl” Jesse arrived home that evening and I was waiting for him in the living room. “Oh Jesse! our little sissy has something special for you” Amy teased. My little cock was so hard in my pink panties. Jesse walked in and I curtsied. “Sissy wants to give you her virgin ass tonight. We’ve been training her all week. Isn’t that right sissy?” “Yes mommy. I want daddy to take me tonight anyway he wants” I said in my sweetest girly voice.
“Well now this is a surprise.” Jesse said. “Are you sure she is up for it” he asked Amy. “Oh yes dear we have been prepping her every night.” “Ok then take off those panties and come over here” Jesse commanded. I removed my pink panties and my tiny penis shot straight out. I’ve never been harder. They both laughed out loud at how hard and how small I was. Jesse got his pants off and told me to kneel before him. I did as I was told. He presented me with his semihard member and I greedily held it in my hands as it started to grow. “Put in your mouth and suck on it” he said. I could barley fit the head in my mouth as I felt it grow in my hands. I started to get nervous because it was definitely bigger then the 9” dildo I had been practicing with and thicker. I worked on his cock until it was rock hard. I don’t think Jesse every plays with himself so this was more than a week of pent up sperm waiting to come out. His balls here like softballs in my hands.
“Ok sissy are you ready?” Jesse asked. I got really nervous and looked over at mommy “Please be with me mommy. Come hug me!” “Of course sweet heart” she said as she grabbed the lubricant, and told me to bend over. She put a big dollup of Vaseline up my asshole and rubbed it all around. She sat on the couch and told me to put my head in her lap and bend over. She started stroking my hair and whispering in my ear that everything will be alright. I felt Jesse’s hands on my hips and braced myself for what was about to come. Jesse and Amy looked at each other and smiled as he positioned himself at the entrance to my asshole. “What would you like to tell Jesse sissy girl?” Amy asked me. “Oh please take me. Take my virgin ass. I belong to you. I want to be your sissy bitch!” I cried out as Jesse pushed his massive pulsing cock into my little virgin ass.
I cried out in a little girl voice. It felt like I was being torn in two. He was so huge. I looked into mommy’s face as tears come to my eyes. She caressed my face and kissed me. “Our little sissy. Just give in an accept your sissy fate”. I did and soon I was so full of his cock that it no longer hurt. He was thrusting into me as my legs started to quiver and I felt so weak. He held me up and kept thrusting himself into me. I was squealing and pleading like a little girl. I shook so much as an orgasm washed over me. My tiny cock sent streams of girly cum flying. It was splashing on Amy’s bare legs as she watched. She bent my head down so I could lick up the cum while Jesse relentlessly pounded me. He finally filled my no longer virgin ass full of his cum. I could feel it inside of me. I wanted to be their sissy girl forever.