I woke up with my s****r still a sl**p in my arms. At first I thought I had dreamt the whole thing. Mom and s*s had known about me wearing their stuff and had dressed me up and turned me into a girl. My b*****r, Zach, had fucked my ass. My dad had fucked me as well and my s****r showed me how to suck cock. And for the first time I had put my dick in a women’s vagina, as my s****r rode me to one of the best orgasms I have ever had.
But I let my s****r go and moved down to her pussy to give her a nice wake up. I grabbed her panties and pulled them down to her knees and I started kissing and nibbling on her clit. I soon began to dart my tongue inside and use my fingers to rub her button and stick some inside. She stirred awake and was moaning and saying, “don’t stop s*s, this is the best wakeup call a girl can get.”
She grabbed the back of my head and f***ed my mouth to remain on her pussy. It wasn’t too long after that she screamed out an orgasm. She gushed her juice and I ate up as much as I could and she pulled me back and we kissed.
Though Mom came through the door and told us to get ready as we had a big day planned. I remembered my s****r saying we were going shopping and more. I expressed some hesitation about going out dressed like a girl.
Mom said, “Don’t worry sweetie you already looked somewhat feminine and we will make you up into a pretty girl. The boys will be whistling at you and the other girls will either be jealous or they will think you look fantastic.”
“Yeah that’s right s*s” said my s****r. “You are going to be just as pretty as any girl out there.”
With that we got off the bed and went into the bathroom. We dropped our panties and pajamas right there on the floor and hopped in the shower. My s****r made sure I had no patches of hair remaining and we took turns cleaning each other. We got out and dried each other off.
We gave each other another enema and went back into the bedroom and she told me to choose my own underwear. I decided to wear a bikini swimsuit. It was neon pink and with ties for the top and the sides of the bottom. She picked out a pair green satin panties with black lace around the top and a matching bra.
We went to closet and she picked out a white skirt and black short sleeved top for me and a little black dress for herself. She laid them on the bead and grabbed some breast forms that she stuck into my top. We put on our outfits and she had me sit at the makeup table. Before my very eyes emerged a very pretty girl. I couldn’t believe it and she topped it off with pink lipstick.
She did her makeup and was telling me that if they weren’t in a hurry she would be more detailed in what she was doing so she could teach me how to do it on my own if need be. But that would have to wait.
We walked out of our room and walked into mom’s room. Dad was coming out of the bathroom and he came up and said, “You girls look great.”
With that he came up and kissed us both but he let his hands roam underneath my skirt as he fondled my butt thru the bikini bottoms.
To which my mom saw and came up and playfully slapped his hand away. “Sorry honey but we got a busy day today and we don’t have time for that now.”
“Ok, Honey” said my dad. “You girls have fun.”
He gave my butt a playful slap as we walked downstairs. Mom was wearing a pair of white Capri pants and a blue halter top. Her breasts were almost spilling out of her top. We went into the kitchen and we each had a bagel and some orange juice. We walked out to the garage and hopped into the Suburban.
We took off but instead of heading to the mall as I expected my mom told me we were going to pick some people up. This worried me a little bit but I knew that as long as I was with my f****y it would be just fine. We pulled up to a house that I had been to before many times in the past. It was my Aunt’s house.
We went up to knock and my aunt Becky came to the door and she kissed us all. When she got to me she looked me up and down and said, “Wow you look great Emily. I can’t believe how beautiful you turned out.”
She gave me a kiss and ushered us inside into the kitchen where I found my two cousins Samantha and Annie. They came up and greeted us all and when they came up to me they gave me a very happy and somewhat excited hug and said how pretty I looked.
Aunt Becky said I should show off what I was wearing underneath the skirt and top. I looked at mom and she gave me a look like don’t you dare disobey, but she said “We are all girls here honey, and we are all f****y.”
I unbuttoned my blouse and revealed my hot pink bikini top. I then wiggled out of my skirt and let it fall to the floor letting them see my bikini bottoms. I stood before them in my hot pink bikini and black high heel shoes.
Aunt Becky then called for somebody by the name of Tiffany to come in and in came a girl in a red teddie with black lace around the edges. Though when she fully entered the kitchen I couldn’t help but notice the bulge in the crotch area and when I gave her a closer look I could make out that is was actually my cousin Connor, a boy that was made to look like a girl just like me.
Aunt Becky, then said, “Tiffany why don’t you give Emily a kiss.”
She/he came up to me and kissed me and at first I was hesitant but I couldn’t help it as he or she was so darn cute and I started kissing her like I wanted too and I let my hands come to rest on his butt. He did the same and Aunt Becky told Tiffany to show me her bedroom.
She led me by the hand downstairs to what kind of looked like a dungeon. We walked by what looked like a pommel horse and a table with restraints on it and other devices that I could only speculate as to what they would be used for.
Though as we moved toward the back, the room brightened up into what looked like a little girl’s room. There were stuffed a****ls and a four post bed. There were unicorns and bears and pink striped walls with white furniture. It was a little girl’s room but Connor, or Tiffany was 18. He led me to the bed and said “this is where I sl**p and have fun sometimes.”
Aunt Becky then told us to get on the bed with on top of the other. Tiffany got on first but Becky told him lay along the short length of the bed and to have his butt hang just over the edge. I was told to get on top of him with my crotch in his face and for my head to be near his crotch. Tiffany took my cock out and started sucking it and my mom told me to return the favor which I did. I unbuttoned the bottom of his teddie and let his cock spring out and I sucked just as my s****r had taught me too.
We sucked each other’s cocks for a while until I saw Samantha approach Tiffany’s butt and my face and she was wearing a strap on dildo . I also felt the bead begin to shake a bit on the other end and I stopped sucking to look around and I saw Annie with a strap on too. I knew what was coming as I saw Samantha lube hers up and positioned it at Tiffany’s ass hole. I also felt a pressure as if something was about to enter me.
Only a second later I felt it push into my butt as I saw Sam push hers into Tiffany’s butt. I moaned in pleasure as I continued to suck on her cock. We were in a 69 sucking each other off while get fucked by my cousins, her s****rs. It didn’t take long for me to cum but Tiff took a little longer but I swallowed every drop. Sam and Annie removed their cocks from our holes and took them off. All four of us got cleaned up and fixed our makeup.
Aunt Becky said they were ready and we all hopped into our car and made our way to the mall. I and Tiff got the back seat where we were making out. My cousins and s****r were in the third seat and each was playing with each other’s pussies. We pulled into the mall and we quickly fixed up our makeup and headed in. Aunt Becky and my mom let us girls go off by ourselves and they gave us each a $150 dollar mall gift card and they went off by themselves.
Samantha suggested we go to Victoria’s Secret. We all went in and I felt a bit apprehensive till a sales rep came and asked, “miss is there anything I can help you find?”
I was stunned as she didn’t even register a look of discomfort at all. It was just a normal question she asked thousands of girls before and I was just another girl to be helped. I asked her where her teddies were and she showed me where I could find them. She also told me where the changing rooms were and then she smiled and said if I needed any help to just let her know.
I looked to see Sam come over and tell me that that sales rep was a good friend of hers and she was bisexual and knew about Tiffany’s secret as well. She told me to ask the Sales rep for help with the teddie that I had picked out. I hesitantly did and she took me into the changing rooms and told me to take off my clothes and to put the teddie on which I did. But when I stepped out of my panties and revealed my cock she gasped but she soon said, “Wow I didn’t know Sam had another sissy friend.”
I told her I was her cousin and with that she unbuttoned her top and dropped her skirt, while I put on the teddie. She moved the front of the material out of the way to reveal my cock and she mounted me. We fucked and I came inside her just before she let out her own orgasm.
She said she had to get back to work and “don’t worry I am on the pill.”
I took off the teddie and put my bikini, skirt and top back on. I picked out a couple pairs of panties with their matching bras and a babydoll, along with the teddie and went to pay for them. Sam’s friend was at the register and she gave me her employee discount which was nice of her. But on the receipt she put her phone number and name and said I should meet her boyfriend.
She gave me wink as I left to join my entourage outside. They had their own bags and asked if I had fun in there. I told them all about it and Tiffany said, “Yeah you definitely got to meet her boyfriend as his cock is the biggest I have seen.”
We all giggled at that and made our way to the food court where we got something to drink. We sat at a table and talked. We noticed a few boys looking our way. One of them had the courage to come over and ask us how we are doing. He introduced himself as Jeremy and asked if he and his friend could join us. My s****r spoke up and said sure come on over.
They came over and the other two introduced themselves as Brad and Riley. We told them our names and we talked about what school we went too and what music we liked and where we liked to hang out.. But they soon asked about what we had in the bag. My s****r piped up and said “Emily would be happy to show you. But you should know that she is actually a he.”
I couldn’t believe my s****r had said that and I thought I could get beat up or at least a scene would erupt. They looked at me again with stunned faces and Jeremy spoke up and said, “Ok, she was the reason I came over here so what the hell, I’m down with that.”
The other two said they were cool with that and they told us they had a room they were in town for the football game and that they had a room in the hotel just across the street. We called our mom and Becky and told them where we were going and they just said have fun but to all go with me just in case.
We went over and I and my s****r went into the bathroom as everyone waited in the room. I was going to pick out something from my bag, but my s****r said she bought something for me and that I should wear this. It was a black lace halter top and matching bikini panties. I had a blond wig that was cut into a short but curly hair-do.
I then ventured out into the room where the guys were already naked and sporting erections. I smiled and was told that to give them a lap dance. I had seen this before and I just did what I remembered. I ground my ass into the crotch; I shook my butt in their faces and humped their legs. I laid on the floor and spread my legs before them, kissed their chests, and played with their hair.
Jeremy grabbed me and bent me over the couch. Sam spoke up and said that they had paid for the right each to get a blowjob and for each to get a crack at my ass. Jeremy pulled my panties down and roughly f***ed his cock in my ass. Brad got on the couch and stifled my moans by putting his cock to my mouth and I started sucking as he fucked my mouth as well. This was the first time I had been f***e fed a cock in my mouth.
I was getting assaulted at both ends but after about six minutes they had me mount Brads cock with my back to him while Riley put his cock in my mouth and he too pumped himself into my mouth at will. I was slobbering and gagging and Ann said, “that’s it you nasty slut you suck those cocks.”
I looked over at them and saw Sam and Annie in a 69 and my s****r sucking Tiffany’s cock while also fingering her own pussy.
Brad came in my ass and he ordered me off him and Jeremy ordered me to the bedroom. He had me lay on my back on the bed and told Riley to throw my legs over his shoulder and to fuck my ass. He got in position and entered me while Jeremy mounted my face and fed me his cock with the same pace he had assaulted my ass. It didn’t take long for Riley to deposit another load in my ass while Jeremy continued to assault my mouth.
He pulled his cock out my mouth and got off the bed and went to sit in a chair in the bedroom. He had me follow him and get on my knees in front of him and to suck his cock that way. He told me to suck fast and get sloppy and I did so and he told me he was going to cum on my face. He had me back up just a bit and he pointed his cock at my face and had me jerk it to fruition. The first spurt landed on my forehead and got a bit in my hair. The second landed right along my nose and a third landed on my cheek and smaller fourth one landed on my lips.
He had me clean his cock and Tiffany came over and licked my face clean and gave the boys a peek at his cock which he had left out after Kelly finished him off. Annie called Aunt Becky and mom and told them to pick them up at the front of the hotel. I took off the halter top and gathered up the panties from the living room floor and went into the bathroom with my s****r who fixed my makeup and I put on my original clothes.
We said goodbye to the boys and as we took the elevator down I could feel their cum leak into my bikini bottoms. I told the girls this and Sam produced a tampon saying that it would stop it from messing up my bottoms. She had me bend over and she slipped it in.
We made our way outside and I could feel the tampon move in my ass. We hopped in and Mom told us that “we are now heading for a consultation with a plastic surgeon who has agreed to give Emily boobies.”
So we were off to the doctor’s office or more specifically a plastic surgeon that my mom knew and had arranged for me to get some real tits. She told me this was just a meeting with the doc so that he could give me an examination and tell me all about the procedure.
But before we could get there my mom pulled into a gas station where she took me into the single use ladies bathroom. Mom brought a bag with her and once inside she told me to take my clothes off. She began taking garments out of the bag and folding them over her arm as I stripped everything off as instructed.
She produced some white satin panties with black trim around the edges and a matching bra which she told me to put on. I slid the panties up my legs and snapped the bra snaps together and turned it back around and put my arms through the straps.
She then handed me a pair of skin tight jeans which gave my butt a lift. They took a while to get on as they were really tight. Up next came a black and silver sequin tank top. Mom said “when you get your new boobies this tank will look even better but for now I am going to fit you with these breast inserts for now.”
We took a quick glance in the mirror to make sure our makeup was in order and mom gave me a spank on the bottom and ushered me out and into the suburban. Everyone liked the way I looked and wanted to see what I was wearing underneath.
I unbuttoned the jeans and pulled them down and took the tank off as they commented on my panties and bra. Kelly said that I was even cuter and started rubbing the front of my panties which caused my penis to pop up and press against the panties. Aunt Becky seeing me in the rear view mirror spoke up, “OK girls don’t get Emily too excited as we don’t want her making a mess in her new panties as she has to be presentable for the doctor.”
I pulled the jeans back up and the tank back down. My cock began to slowly go down but my excitement mixed with some anxiety still occupied my head and heart. But even then I still felt safe with my f****y around me and knew that I would be ok. Also my mom had been going on about how she and the doctor had dated in college and telling us that he was a still a good friend which calmed my feelings of anxiety.
We pulled into the doctor’s office parking lot and we all piled out and headed in. I and my mom went up to the check-in counter while the rest of the clan took a seat in the waiting room. The receptionist recognized my mom and said, “Well this must be Emily.”
I began to wonder and get a little worried about who all knew about me and how much did they know. My mom responded, “Yes this is her and she has an appointment with Dr. Moss.”
“Well we are all ready for her just let me call the nurse to lead you to his office.”
It wasn’t too long after that a nurse came through one of the doors and ushered me and my mom into the back hallways. We went past a nurse’s station and past a couple doors and took a left down another hallway where after just a couple more doors we arrived at Dr. Moss’s door. The nurse knocked and said, “Dr. Moss, your patient Emily is here.”
“Come on in.”
The nurse opened the knob and told us to go in and Dr. Moss told us to take a seat as the nurse took a standing spot next to Dr. Moss facing us. Dr. Moss was sitting at his desk and asked, “How are you two ladies this afternoon.”
“Oh Robert we are just fine and how are you darling,” said my mom.
“Just fine and I must say Emily you look very beautiful, but we can make that figure you got look more like a women.”
I blushed as Dr. Moss looked me up and down. He began telling my mom and me about all the different sizes of boobs he could do and asked us which size we would prefer.
Mom spoke up and said that a C-cup would be nice. Not to big but big enough to be noticed. With that Dr. Moss showed me some examples of his work on giving girls C-sized boobies. He then had the nurse come and take my measurements.
After doing that she told me to undress as the doctor had to check my body out. I pulled the tank over my head and started peeling the jeans off. The Nurse told me I could leave my panties on but my bra had to go. Mom came up behind and unhooked it and I let it fall to the floor with my other clothes.
Dr. Moss had me come around to his side and stand before him. He pinched my nipples and felt up my chest. He then told me to sit on his desk facing him in the chair. He commented again on how pretty I looked and he started rubbing the front of my panties.
He pulled my dick out from my panties and he started licking it and kissing it and running his tongue along the underside. After a little bit of this he took my cock fully into his mouth and sucked it. I was surprised at this and was enjoying that this man decided to take care of me first. My mom and the nurse just watched. It wasn’t long before I started telling him that I was cumming.
He didn’t let up and took my load into his mouth but he didn’t swallow and came up to give me a kiss and we shared my cum. He put my softening cock back in my panties and helped me off his desk onto his lap. He then asked if I was surprised and I said I was. He went onto explain that he was bisexual and that he had performed a number of plastic surgeries on guys to add feminine features.
He then told the nurse to come forward and she stood right in front of us. Dr. Moss ordered her to hike up her skirt and that was when I noticed a bulge in her light blue panties. She pulled them aside to reveal a short but pretty penis.
I was surprised but also stated licking my lips and the doctor said that Sara, his nurse, had been a patient of his too. He went on to tell me that Sara would accompany me home and help me in my transition as the nurse slipped her cock back into her panties which made me pout a little. The doctor said that she and I should become good friends.
He then pushed me off his lap and told me to get dressed and I could only regret that I wouldn’t see the doctors cock but I felt that I wouldn’t have to wait too long to restore the favor. Mom thanked the doctor and we all headed out to the waiting room where we joined up with the rest of our group and we all hopped into the suburban. It was now one seat shot so Sara had to sit on my lap.
My cock sprang to life again as Sara’s butt rubbed against my crotch to which see said “someone’s getting excited and I am so flattered that I have aroused you so much.”
Everyone else smiled and continued talking about how cute Sara looked and how they looked forward to me having tits like hers. We drove like this for a while until we pulled into an adult store. My mom explained that we were here to get me job.