My Sister Helped Me Become a Girl - Cover

My Sister Helped Me Become a Girl

by Bob Watergate

Copyright© 2021 by Bob Watergate

Erotica Sex Story: My sister Debbie had caught me multiple times smelling and licking her dirty panties! Instead of being made she began to encourage me with even better smells and tastes! Debbie and I loved each other and she helped me with my feelings and most importantly my desire to become a girl!

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   Ma/ft   Fa/ft   Ma/Ma   Mult   Teenagers   Consensual   NonConsensual   BiSexual   Heterosexual   TransGender   Fiction   Incest   Brother   Sister   Black Male   Anal Sex   Cream Pie   First   Facial   Oral Sex   Sex Toys   Body Modification   Size   Small Breasts   .

Chapter 1

Even while we both lived at home with my older sister, age 16, had caught me multiple times dressed up in her panties and bras or come into our only bathroom catching me smelling or licking her dirty panties! Unlike other tales I have read about, my sister never threaten me or expected some sort of compensation!

She scolded me a few times but after a while she became less angry and at times it even appeared that she was either allowing me to continue or even encouraging me to continue! She must have guessed a 14 year old boy just couldn’t help himself!

This encouragement greatly improved when I started noticing her dirty panties left in our shared bathroom laundry basket became, well let’s just say that they were much or fragrant than before! I would not only find pee and poop smells but also larger spots and even streak’s! What I found most amazing was I began to find them quite wet but not from her pee, which I could still smell wildly, but from her cum! She had to have been masturbating in her panties and then wearing the panties to allow her cum to drain into this new prize just for me!

The next thing I noticed I found a pair of her panties and the matching bra in my underwear drawer! Wow I thought, I don’t even have to risk going into her room to put them on! So with this exciting event I began wearing my panties and bra under my regular clothes; not only at home but also during the day too when I would go to school or go shopping! This all was working great until that fateful day when I had an appendicitis attack and was taken to the hospital for treatment!

My mother worked at this hospital so she was notified and was right there when they brought me in. This act of love should have been met with equal love in return BUT she was standing there when the nurses began to undress me which showed off the cutest pair of sea blue panties and matching lace bra!

“What in the world do you have on Bob?” my mother screamed! “Did you take your sister’s underwear you little pervert? You just wait until your father hears about this young man or should I call you young girl?”

Hearing my mother ranting and seeing how devastated I was one of the nurses took her out into the hallway and was actually scolding her for her mistreatment of me! The other nurse leaned down next to my ear and whispered, “It’s ok dear, I’ll put your pretties away and no one else will see them. Trust me honey my boy is even younger than you and he likes my panties too!”

My condition was so urgent that I was taken directly into surgery. The next thing I knew I was in my room after staying in recovery for over an hour! When I opened my eyes I saw my sister setting next to my bed holding my hand!

“Bobby I’m so happy they got you taken care of before things went terribly wrong!” Debbie told me, “I know your feeling terrible right now but I have a little surprise for you love.” With that she took my hand and brought it down so I could feel the panties I had on! “When I got here a nurse took me aside and told me how mom acted stupid to you and then asked me if I knew about you wearing panties and bra! I told her that they were actually mine and I had given them to you to enjoy and to live out your little fantasy!” Debbie then told me that as soon as she had shared those facts the nurse hugged her and gave her a kiss on her lips telling her she had done the same thing for her little brother back in High School!

We continued to visit when my mother came back into the room and she seemed like a different person. She didn’t appear to be angry and didn’t even mention the panties or the bra that I had been wearing earlier! Later my father came to visit me and he too was all smiles and encouraging me to get better so I could get out of the hospital!

A couple of days later when I was being released the nurse was so nice to me. She told me it was time to remove my catheter so she pulled the covers down, slid my panties off and then removed the catheter from my penis.

“You have such a cute little clit!” I heard her tell me. Then she took my dirty panties and put them in my little bag and picked up not only a clean pair of panties but again the matching bra! “Your sister Debbie dropped these off for you early this morning and asked me to help you dress for you return home young lady!” This nurse helped me finish dressing and then she took me out in a wheel chair and told me she would accompany me to the front of the hospital. Once there I saw my sister waiting for me with a big smile on her face!

“You ready to leave Bobby?” She asked me? She pushed me out to the car and helped me get in. “Sweetheart just so you know we’re not going home! We’re heading to Becky’s house. Becky will drive us and I’ve talked to her mother and father and they have agreed that we would live with them until we both graduate school and possibly longer if we want too!”

Debbie also told me that she had spoken, in detail, with both Becky and her mother about my love of female lingerie. She even shared about my love for her dirty panties!

When we arrived at Becky’s her mother was waiting for us at the front door! She greeted us both with a big hug and a kiss! She then showed us the spare room we would be sharing for the time being. There was only one Queen Size bed but that didn’t seem to trouble Debbie one bit! We got unpacked and Debbie read me the Outpatient Instructions telling me that for the next week my dressing would have to be changed and cleaned twice a day.

The first couple of days Debbie it was there to assist me. But the third day she had classes into to the evening so it was Becky, who was now 19, who assisted me in the morning and her mother that evening!

“Booby I’m happy to help you out any time dear!” Becky told me. She told me to stand still and she slipped my shirt over my head and lowered my pants and my panties to the ground. “Debbie has shared everything with me and mom to make sure that you are a comfortable as possible.” With that that she slipped her panties from under her dress and handed them to me! “Enjoy sweetheart I know they are extra nasty with a special surprise for you dear! Tom and I fucked last night and his cum has soaked into them too!”

So Becky cleaned and then redressed my surgical wound and then she started tickling my penis head! “Does this make your little clit feel good honey?” Becky whispered? “I know when I diddle my clit it drives me wild!” She played with me until I pushed out a little bit of cum which seemed to make her quite happy! Then she told me, “Good job Bobby; you did real good sweetie!” She then took a finger getting the cum on it and put it to my mouth. “I know you enjoy the taste of cum don’t you sweetheart!”

The afternoon went ok but when I was using the toilet Becky’s mother walked in. I had locked the door by the way! She told me it was time to change my dressing! So I finished peeing and stood up as she told me to just carry my pants and my panties and she would help me with them later! She took me to her bedroom and told me to lie down on her bed. She came back with the items to cleanse and bandaged my surgical wound and actually had completed the task just like a professional! Then she lay down next to me on her side and started talking to me.

“Bobby I just wanted to tell you how pretty you look in your panties and bra! She, like her daughter, shared that they had been told all about my love of panties and bras and she went on to even encourage me to not only to continue but to expand into hose and dresses too! Just when I thought this couldn’t get any better she stood up and took her jeans off and then her panties. She had them in her hand and I knew she would give them to me to smell and lick when she tossed them onto the bed and climbed up placing her pussy over my mouth!

“Bobby dirty panties are one but nothing can be better than the actually source of the smells and taste you seem to enjoy so much!” Mrs. Thompson said! She road my face for several minutes before I heard her begin to moan and she started pushing out her tasty cum into my mouth! “That’s it little girl drink your mommy’s cum and lick her hairy pussy you little slut!” It took her several minutes to calm down before she climbed off my face and again lay next to me again! “Bobby please forgive me sweetie,” She begged, “I just got carried away because I was so horny!”

I didn’t say anything but she finally rolled over and kissed my lips and then helped me step back into my panties and pants. “Young lady I see that you have some cum on your clit!” And with that, mother like daughter, she got it on her fingers and placed it in my mouth for me to enjoy!


Chapter 2

The next morning Debbie had plenty of time after both Becky and her mother had left for the day to just set and talk. Debbie asked me how I was doing and I shared how both Becky and her mother had helped me but also had become sexual with me!”

“Bobby sweetheart,” Debbie spoke, “Yes I told both of these ladies about your desire to wear my panties and bras and both of them embraced it. But you have to believe me that none of us spoke about what any of us might do with respect to trying to help or encourage you! I mean you are only 15 years old dear!”

“To tell you the truth honey,” Debbie continued, “I’m just sort of making this up as I go. I don’t have a little brothers getting off on their older sister’s dirty panties or even wanting to wear their underwear book. You don’t happen to have a book of your own do you dear?”

“No Debbie I don’t. I’ve never even spoken to anyone about my desires. I just can’t help wanting to smell or taste your dirty panties!” I began to cry! “Debbie I’m sorry I know I shouldn’t do this but it seems to be so natural for me to want to smell like you and dress like you! Can you continue to help me sis?”

“Bobby don’t cry,” Debbie said, “I do want to help and I’ve sort of figured out how important my pussy smell is! A few friends have told me about their family members getting off on their dirty panties too! Their brothers and sisters, even fathers, mothers, aunts and uncles! Even one Grandfather! So I understand that you like how my pussy smells and even tastes! So let’s just start there, can we?

First how did you like getting to smell and taste Mrs. Thompson’s pussy yesterday? Was that too much or did it finally get it done for you? I know Becky played with you clit. Well let’s talk about terms dear! Both woman, even I call your little thing your clit! Your tiny penis would be your clit; just like I have a clit. Does that make sense sweetie?”

“Debbie I don’t even understand what a clit is so how does that help me?” I asked her sadly!

“My God Bobby I didn’t know so let’s fix that right now!” Debbie told me! She stripped out of her clothes and laid down on our bed! “Honey you get between my legs so you can understand all the parts of a woman! Ok the big lips on the outside are called Labia major and the smaller lips. Go ahead and touch them. Just inside of them, that is called the Labia minora! Most everyone just calls them pussy lips!” She told me. I was lost at this moment because not only could I see her pussy right in front of me but I could smell Debbie like never before so I just pushed in and started licking her pussy!

“Ok honey yes let’s just get this out of the way!” Debbie whispered as she pulled me in ever harder! “Bobbie please enjoy yourself and once you are satisfied we can continue our class!” I licked and sucked on her for a few minutes and I could heard her begin to moan. Then I felt her thighs close against the sides of my head. Then it happened! “O God, ah oh, oh Bobby yes, oh shit yes!” Debbie cried until her cum flowed into my mouth! “Shit Bobby I didn’t think that was going to happen. You can do that anytime you desire love, oh yes sweet love!”

After a few minutes Debbie returned back to her normal self.

“Ok if you’re ready now you see that bump sticking out at the top. Oh go easy when you touch it honey!” Debbie continued trying to instruct me. “Well that is my clit and that is what makes or helps a girl experience an orgasm!”

“So do you pee out of it like I do; you know out of my penis Debbie?” I asked.

“No sweetheart my pee comes out of a hole that just below it. Take your fingers and pull my pussy lips apart! That’s it,” Debbie continued, “see that hole right below my clit? Well that is my Urethral opening and it is just like the slit in the end of your tiny penis! And while you have me pulled open you see the opening at the bottom? That goes way back and is really wet right now? That is my Vagina. That is what people are really talking about when they say pussy. A pussy is where a man puts his cock to fuck a girl and where he shoots his cum, you know his sperm to get a girl pregnant but let’s go into that later ok!”

 
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