Son Turns into Sarah

Story Info
Transvestite son becomes his mum's daughter.
2k words
4.5
105.4k
61

Part 1 of the 3 part series

Updated 10/25/2022
Created 04/15/2012
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It had been a crazy few years. Only 5 years ago I had come out to my mum as being a transvestite. She had been very accepting, not asking many questions but as long as I was happy that was all that mattered. She didn't let on if she knew that between the ages of 12 to 18 I had sneaked her clothes to wear!

Well 6 weeks later I had started a relationship and moved out, my mum said nothing of my confession to my girlfriend and as far as I was concerned my crossdressing days were over. It was a great relationship at first, we had lots in common and spent a lot of time together. However soon the old desire to dress returned and try as I might I wasn't able to fight it. At first this wasn't an issue as I only dressed in secret when my girlfriend was out of the house but one day she came home early and my secret was out. She was accepting, but only with limits, she didn't want me to go out and about dressed or around her. At the time I was fine with this as I didn't want to lose my relationship, but gradually the desire to dress more and go round other t-girls houses for parties grew to be too much and we split up.

This is how, 5 years on I came to find myself sat on my mum's sofa with a cup of tea, explaining the whole situation to her. My mum listened without interrupting, then when I had finished, gave me a hug and said that if I had been unhappy then I had made the right choice and could live with her for as long as I needed. She went on to say that if crossdressing made me happy then I could do it as much as I liked at her home. She asked me if I had brought my clothes with me, I explained that I had them all.

"You look tired and stressed, why don't you have a bath and get changed while I cook dinner?" my mum asked.

"Sounds like a perfect plan" I replied, relieved that I had got everything off my chest.

I went upstairs into my old bedroom, dumped my bags on the bed and went and ran myself a bath. I had a long soak and felt all my worries wash away. I washed and did my legs getting them smooth before returning to my room. I opened up my suitcase and unpacked my things. Looking at my girly clothes and lingerie I realised that they were all quite provocative. I had never really been a fan of tights so mostly I wore hold ups or stockings with suspenders. I picked out my red satin bra with black lace trim and the matching thong with the attached suspenders and put them on. I then found my favourite pair of black seamed stockings and rolled them up my smooth legs, taking particular attention to getting the seam straight. Then I grabbed my favourite dress, a pink satin number with a plunging neck line and put it on. I glanced over at the mirror and realised that it only just covered my stocking tops. I grabbed my make up bag and applied my foundation, scarlet lipstick, dark eye shadow and mascara. I slipped on my dark red suede high heels and checked myself out in the mirror.

"Looking quite hot today" I whispered to myself.

"Are you ready yet? Dinner is ready" shouted my mum up to me.

It snapped me back into reality, was I really going to have dinner with my mum all dressed up? I suddenly felt very nervous.

"I'm not sure about this mum" I shouted back.

"Oh do get a move on darling, I'm not going to judge you, but it's up to you".

I decided that I needed to do this if I wanted to accept myself for who I was. I left my room and walked slowly down the stairs, trying to compose myself, my high heels clicking on the bare wooden floors.

I went into the kitchen and saw 2 bowls of pasta, a bottle of wine and 2 glasses on the table. My mum looked up at me.

"Wow, you look pretty good" she said, open mouthed.

We sat at the table, ate, drank and chatted. Mostly we talked about my crossdressing. My mum said she had known for a while that I had been wearing her underwear when I was a teenager but that she didn't mind as she figured there were worse things I could have been getting into as a teenager.

"Do you not have a wig?" my mum suddenly asked.

"No I could never afford one" I replied

"Well tomorrow I think you and I should go out and go shopping. I know a place in town we can go to, it's hidden away so it's nice and discrete".

"Great" I said, feeling glad that my mum was being so supportive.

We took the rest of the wine over to the sofa and switched on the tv. We soon polished off the wine and were on to the second bottle when an advert for make up came on the TV.

"You know, I think your make up looks good, but I'm pretty sure I can make you look better, would you mind if I tried" my mum asked.

"No go right ahead" I replied.

My mum went off and returned a few minutes later with her make up bag. She removed my eye shadow and mascara and re-applied it. She finished it off with some eye liner.

"Well what do you think?" she said as she handed me the mirror.

I couldn't believe how much better I looked.

"So what do you call yourself when you are dressed up, surely not Fred?" my mum asked.

"Sarah" I replied.

"Well Sarah, I think you look beautiful"

I blushed brighter than my pink dress, but I caught my mum's gaze and I could tell she meant it. I could also feel that her gaze was a little more than that. We locked eyes and leaned towards each other.

"I'm not sure it's the wine talking but I just want to kiss those lovely red lips" my mum whispered.

I leaned forward and kissed her, I felt a shock of electricity run through me but my mum broke it off quickly.

"I'm sorry" I said.

"No I enjoyed it" said my mum, "it's just that, I feel a bit underdressed compared to you."

"How?" I laughed, motioning down to the fact that my dress had ridden up, exposing my stocking tops.

"Mmmm, well I think that is a good look for you Sarah" my mum said grinning.

With that she put her hand on my thigh and started to stroke it. It felt like I had been electrocuted again, I was tingling all over.

"I think you have great legs, very womanly, if I'm honest I've always found a woman's body very erotic".

My mum continued to stroke my stocking clad legs, by now I was in heaven, then I could feel my mum's hand reach up under my dress and stroke my panties.

"Nice, feels silky, can I see?" she whispered.

I hitched up my dress to expose my knickers and was surprised to see a large bulge in them.

"Wow looks like you are enjoying this Sarah"

"Oh I am mum" I replied.

"So are you wearing the matching bra to that thong?"she asked.

"I always match" I responded.

" Well then take off the dress and let me see" mum ordered.

I stood up and reached for the zip, undoing it and letting it fall to the ground and I stepped out of it.

"Well Sarah, you certainly have good taste in lingerie" my mum said, her eyes taking in the view of my stood before her.

"I think I get that from you mum" I replied, "I think it's time I saw yours."

"Well OK, I guess there is no harm in 2 girls hanging out in their lingerie together"

My mum took off her t-shirt and unbuttoned her jeans before slipping them over her ass and legs. I could see she was wearing a sky blue bra made from a fine mesh with a darker blue flower design sewn on it. They only just contained her 34FF tits. She was wearing a matching brief with the same design going down the front, as she gave me a twirl I noticed that could see her ass through the material.

"The only thing missing is a pair of heels mum" I said.

"I've noticed that you still call me mum Sarah, I guess that makes you my daughter. Well daughter lets go upstairs and pick a pair of heels out shall we?"

We went up into her room and picked out a nice pair of black strappy heels, she put them on and walked over to me, her hips wiggling provocatively. She stood close to me and put her arms around me.

"Well I'm enjoying having you home daughter" she said as she looked sideways into the full length mirror.

I looked over at it and saw us there in our lingerie, our legs in between each others and our panty covered genitals only inches apart.

With that she slid her hand down inbetween us and started to rub my cock through my panties. That electric shock feeling came back again. My cock was pushed downwards in my thong meant that it appeared as though she was rubbing it like a clit.

"MMMMM, that feels so good mum" I moaned.

"Does my daughter like it?" she whispered back.

I looked down and saw our bra's touching, her breasts squashed tightly against mine, almost exploding out of her bra. It was a sight that almost made me cum right there.

"Calm down daughter" she said and pushed me onto the bed.

We lay on our sides facing each other. My mum took my hand and placed it on her mound, only the delicate material of her knickers separating my hand and her pussy. I could feel how wet she was there. She started to grind against my hand as she continued to rub my cock through my panties. My mum then took her middle finger and placed it in her mouth, licking it up and down, she reached around and pulled my thong to one side and inserted her finger inside me, I moaned loudly.

"MMMM, does my daughter like being fingered?" she teased.

"Oh yes mum, I do, finger your daughter" I pleaded.

My mum finger fucked me faster and faster but I wanted to make sure she got some too. I changed position so that we got into a 69, with me on top. I could now reach my hand down my mum's knickers, I slid 2 fingers into her soaking pussy and rubbed her clit with the palm of my hand.

"ooohh, where did you learn that" she whimpered.

I wanted to reply but all I could think about was her finger in me and I wanted more.

"More mum, more fingers in me" I begged.

She obliged, inserting a second and then third finger in me. I could feel my ass getting stretched, but I loved it, moaning in ecstasy.

"Wow, my daughter is a bit of a slut, it's such a turn on"

My mum's breathing became heavier, I could tell she was close to cumming.

"Oooh make mummy cum daughter, make me cum" she ordered.

"I'm close to mum" I cried back.

"Cum on me daughter" she begged, "CUM ON ME NOW!"

She pulled my cock through the side of my thong just as wave after wave of hot cum spurted from it, covering her bra and tits.

"Good girl" she screamed as she arched her back and her orgasm took over.

I lay back on my side facing her watching as she scooped up all my cum with her fingers and we then sucked them clean.

"I can't wait to go out with you tomorrow Sarah" she said

"Me too" I replied.

With that we got under the covers and fell asleep, that night I dreamt of my new life as my mum's daughter.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
16 Comments
AnonymousAnonymous8 months ago

Thought this story was FANTASTIC! Stories similar to this need to be made very accessible for a great number of youth. Relaxation for open discussion with parents and grandparents.

I have a grandson that, I have heard, has come out to a few, but not me. Hopefugly I will be as supportive as possible.

AnonymousAnonymous9 months ago

I used to cross dress for my many years ago what got me to wearing lady's lingerie was we were wacth the maury show with cross dressing these men were gorgeous I told my wife I'd like to fuck one she said no u going dress for me and let u suck my strapon and fuck u truth be known that was fantasy she look at me and said lay day take it like a slut she fuck real good I never cum so hard before then after that we kept doing that for awhile and to her I wanted a man cock in me and found one he agreed to it he was also bisexual and cross dresser to that's a best threesome ever .

AnonymousAnonymousabout 1 year ago

It was magic i wish i was Sarah I wish i had a mother like who would dress me as a woman

CelloplayerCelloplayerover 4 years ago
Gene to Jeannie pt2.

We had three weeks before school let out for the summer. I had to be Gene for school. Rest of the time I was Jeannie. The boys stopped playing with me. Ken my best friend from school still did. I was always Gene around.

Brenda and I enjoyed being together. Her parents didn't mind.

I was comfortable wearing girls slacks around her. Her parents didn't mind.

My mom was teaching me to cook, do laundry, iron and sew.

Three weeks after our shopping. My mom said I needed to shave my legs again if I wanted.I asked did she want me to do it.

She said I want to watch for the first couple of times. Then you do it when you think it needs to be done. We went to my room. She brought the shaving stuff in.

She handed me a razor and showed how to do it. I said Brenda doesn't have hair under her arms or between her legs.

I got a shocked look by my mom. How do you know that.

I said, "When Brenda and I play and she is in a dress or skirt and is wearing white or pink panties. I can tell. Girls don't have hair down there.

My mom showed me how to shave my underarms. She then had me take my slacks and panties off. She had me lie down. She touched me between my legs.

She said, " This is pubic area and pubic hair.

I said, " Shave all my pubic hair off. I want it like my legs. "

She said, "OK,"

Shortly she said , " Now you have what is called a feminized body. "

She laid down, she pulled her pants and panties off. She had a lot of hair there. She said girls get it there when about sixteen or so. She told me, "That dad used to shave her there. Now she didn't have anyone to do it.

I said," Would you like me to shave you. "

She said, "OK, I'll be right back."

She came back with a hand mirror, small scissors and two pieces of plastic wrap.

She told me to take the scissors and cut the hair. It had to cut shorter before it could be shaved. I was told to take the hair I cut and put it on the plastic wrap. As I cut the I put some on each wrap. She held the mirror and looked. She then said to put the shaving cream on and shaved her. Then her pubic area was bare like mine. She looked and said, "My daughter did a better job then my husband."

I asked, " What did dad do next. "

She said sometimes he would kiss all around and stick his tongue in the hole. Without saying anything. I put my head down there and began kissing and licking. The outside first where I shaved, then the inside. My mom made some sounds I have never heard before. She told to me to stop.

I asked her did I do something wrong. She said no you were wonderful. She pushed me down and began to do it to me. She put my thing in her mouth. She stopped.

She said, You can't tell anyone that we had sex together.That's what people call making love.

The summer flew by. School was starting in three weeks. I haven't had my cut since Christmas eight months ago. It was long and I really didn't want to have it cut.

We got a.book from the school. The rules for this year. Mom read she got about halfway and squealed. She said look. It said boys didn't have to have short. Just as long it was cleaned and neatly kept.

Mom gave me a book to write in. I wrote everything that happened except me and her having sex. Which we did two of three times a month.

AnonymousAnonymousover 8 years ago

what a sick sad turn of avents. born a man that is what you are

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Making Out With Mom He gets to know his mother REALLY well.in Incest/Taboo
Sitting on My Son's Lap A five hour car ride to college.in Incest/Taboo
Can I Watch, Mom? (Illustrated) Mom trades sexual favors with her son.in Illustrated
Linda's Discovery Mom discovers her son's secret.in Incest/Taboo
Under Mommy's Direction Ch. 01 A Mother decides to sissify her Son for a better life.in Incest/Taboo
More Stories