My Aunt's assistance in Crossdressing

My Mother's sister came to our house to talk to my Mother, whom she (my Aunt) had caught looking through her lingerie. I was a young boy (around five or six). My Aunt saw Mother and me dressed in our lingerie. My Aunt told my Mother she understood my interest in her lingerie.

My Aunt was a beautiful woman with an impressive figure. Her breasts were huge and always had my attention if she bent over in front of me. My Aunt was very receptive to my crossdressing. She babysat me several times. She made sure that I was dressed in feminine lingerie. Also, she made sure that I saw her dressed in lingerie.

She always helped me dress and placed my clit delicately in place in my panty. Many times, she saw a tiny bulge in the panty. At this age, I was only wearing a panty.

As I got older and my lingerie selection increased, she led me into the joy of feminization. I love being feminized by her. I learned to apply makeup before putting on lingerie. A lady did not want makeup on her underwear. As my Aunt stood between my spread legs to apply my makeup, I knew my clit had become more erect. My Aunt did not mind seeing my erect clit. As she fastened my garter belt and attached my garters to my stockings, she gently touched my clit. Frequently, I walked around her house in a bra garter belt, stockings, and high heels. My makeup applied and a lovely wig. My clit was hard. Sometimes, she hung a panty from my clit. I was not permitted to touch myself, but I had to keep the panty in position.

As I matured, my Aunt permitted me to see her nude. I was amazed at the size and weight of her breasts. She let me help her put on her lingerie. I love helping her with her bra and adjusting her breasts in the bra cups. I thought my clit would burst as I rolled stockings up her legs and attached her garters to her stockings.

She introduced me to performing cunnilingus on a woman. I was an adult by now. I loved pleasing her. I loved to feel her react to my tongue on her clit and licking her pussy. I loved her body moving into position to complete her enjoyment and listening to her moan.

During her enjoyment, I was not permitted to touch myself, but I felt semen or precum leaking from my clit. I may or may not have had panties on. Either way, my Aunt noticed my leaking and mentioned my enjoyment of pleasing her was visible. My Aunt started playing with my pussy by inserting a finger or two. I thought it was beautiful. I knew this was how a woman felt when she was having vaginal intercourse. My Aunt did give me handjobs. When I ejaculated, she fed my cum to me. I loved swallowing cum. Sometimes, she rubs my hard clit on the outside of my panty or slips until I climax. I LOVED wearing the cum stained garment the rest of the day.

While in college, I lived with my Aunt. I cleaned the house, did laundry, prepared meals, and cleaned dishes while dressed in lingerie. My Aunt made sure that I wore a bra and panty to class. She introduced me to pegging. I felt like a complete woman. Although doggie style was excellent with my head down and ass up, I preferred to face my Aunt as she pegged me. I was always in a bra, garter belt, and stockings. I loved watching my Aunt's breasts as she thrust into me. Most times when I faced her, I had massive cum releases. I had the wear the cum all day.

My Aunt told me that a submissive sissy did not have hair on her body. I made sure I was well-shaven. I enjoyed the silkier feeling of lingerie caressing my body. I wanted my Aunt to inspect my body for hair. She had nude me lying on her bed as she pulled a slip or stocking across my body. We started with me face down, but my Aunt observed my enjoyment as I turned over. My Aunt wore various lingerie garments during an inspection. I loved her breasts in a full slip and no bra being drug across my body.

I wore half or full slips more often. My Aunt always patted my bottom as I walked by her. I loved her gentle attention. I did not care if I was only dressed or partially dressed in lingerie. If I was wearing a panty, my Aunt gave my clit a gentle caresses.

It was my task to hand wash my Aunt's lingerie.

As my Aunt increased my feminization and sissification, she increased my humiliation. She often had me wearing a bra, garter belt, stockings, heels, and full makeup. My Aunt started applying lipstick to the head of my clit. I felt more feminine and slutty. The lipstick on my lips had to match the lipstick color on my clit's head.

When I was seated, I had to keep my legs spread at all times for her enjoyment. She enjoyed dragging a slip across my erection. If I had any precum, she wiped it with her finger and stuck it in my mouth.

My Aunt made sure that I helped her bathe. I enjoyed the opportunity to caress her huge breasts. I allowed her to dry off after the bath. I rubbed lotion on her to keep her skin soft.

My Aunt told my Mother how much I enjoyed being feminized and sissification. Mother did not believe it until she came to my Aunt's house. My Mother had to admit I enjoyed being feminized. My Mother no longer disapproved of my hard clit. My Mother never sexually touched my clit other than tying ribbons to my clit. My Mother did not seem to mind my Aunt rubbing her hand along the outline of my clit in a panty or slip. Mother would sit and watch my Aunt rub my clit until I ejaculated.

My Mother told my Aunt how I enjoyed wearing a pink ribbon and bow around my neck and my clit tied with pink ribbons. My Aunt ensured I always wore a pink ribbon around my neck. She tied each testicle with a pink ribbon and my clit. My Aunt experimented with using various color ribbons, such as red or black or black, with red piping tied around my testicles and clit. My Aunt made me feel so feminine, girly, and slutty.
Publicerad av SissyLong
7 månader sedan
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SissyLong
till kara_sissy : My Mistress took me to a small sex expo.  I was dolled up and bound to the cross.  I was blindfolded.  My skirt lifted, and my panties pulled down.  My tiny clit was exposed.  Admirers were encouraged to rub my clit with a silky slip or party.  It was very humiliating and stimulating.
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kara_sissy
till SissyLong : I find the humiliation to be  immensely satisfying. Even as simple as gym class in high school was a torment and yet satisfying. 
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SissyLong
till kara_sissy : My Aunt, my mistress, and the sales associates were always helpful.  The sales associates were always willing to feminize and sissify me.  I believe they enjoyed tormenting me,  I enjoyed their tormenting and performing cunnilingis on them.  
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kara_sissy
till SissyLong : All of us need mentors to look up to.
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SissyLong
till kara_sissy : She caught me a lot..
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kara_sissy
till SissyLong : Wish I had a special aunt
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SissyLong
till kara_sissy : Yes.  My Aunt was special and encouraged me to dress.
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kara_sissy
So lucy hun
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Loved dressing in my mothers lingerie when I was you loved her slips and girdles and full white knickers loved watching get dressed I was always hard and had to masturbate so many times
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SissyLong
till Pat2610 : I hope both she and you enjoy it. 
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Pat2610
That how  exams Helen see my posts and  ideos
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i4get2000
till SissyLong : I am very happy to learn of your support!
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Julian069
A dream to have a anty like you! Wunderbar! You make me dreaming! Kisses! 
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SissyLong
till Plonk123 : Yes, I was. 
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SissyLong
till i4get2000 : My Aunt increased my desire to dress.  She was more sexual than my mother. I loved her big breasts and cleavage. 
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i4get2000
You were so lucky, I so often would dream and fantasize about being at my aunt's house! I would love being with my aunt and my other aunt next door! Then there was the 3rd house that had a schoolteacher that like the two aunts were all in their 40's! The schoolteacher was a tall very full-figured woman with very large breasts! My two aunts were all BBW's and I lusted about all three of them! 
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Plonk123
You were a very lucky boy . 🥰💦👍
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SissyLong
till Pantyhoseluver9 : It sounds very enjoyable. I do love cleaning up a woman after she has had sex with another man.  I do enjoy swallowing semen and women's juices.
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Pantyhoseluver9
Wow my aunt knew of fascination for pantyhose. She wore them often around me. She caught wearing her hose one day form then on she made me wear them. She also taught me the proper way to orally please a woman. As I got older we had sex quite often. She once brought a man home when I was staying with her. I watched them have sex as I  master-bated. Once he filled her full of his juices she made clean suck her cunt clean of his juices. He was turned on by that and the fact that I had on hose. He came over and laid is cock on cheek and my aunt made me suck it. It was a thrilling experience. He fuck her then pull it out and stick in my mouth till he came in my mouth. My loved it would invite other men over for to have sex with. 
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SissyLong
till justok2005 : Both women support me.  My Aunt encouraged me.
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SissyLong
till justok2005 : She was great.  She taught me a lot.
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Nice Aunt to hang out with Mother with.
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