A New Mom

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A son learns his dad is a cross dresser.
1.9k words
4.45
23.8k
33

Part 1 of the 9 part series

Updated 03/23/2024
Created 02/19/2024
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My new Mom

This is a story of an eighteen year old starting a new life with his crossdressing dad.

My parents separated when I was three years old and I had to live with my mother, I saw my dad odd weekends and during school holidays as he moved to a town just outside London and we lived in the Midlands area.

Things were working out fine, but as i grew, I started wanting to see more of my dad and not really wanting to live with my mother who I was not getting on with very much.

My dad was great to spend time with and he was always nice to me and helped me with school and hobbies as my mother had no interest at all in anything I did.

Now I have left school and reached eighteen, my dad said I can move in with him, but we had a lot to discuss. I was due to arrive at his house on the Saturday afternoon, but I just could not wait any longer and caught the train and a bus on the Friday afternoon, travelling with just a rucksack and a small suitcase.

I walked up the pathway to my dad's front door around 2pm and rang the bell, I heard a female voice say, "one minute I'm coming".

The door opened and stood before me was a lady in her early forties dressed in a tight-fitting dress and long black hair, there seemed something familiar about her.

"Oh my, Tim you have arrived a day early, I'm not ready for you yet!" she exclaimed.

How did she know my name and why was 'she' not ready for me yet, I wondered.

"Is my dad home?" I asked sheepishly.

"I think you had better come in Tim so I can explain" she replied through rosy, red lipstick.

I followed her inside leaving my bags in the hallway and followed her swaying butt into the living room, as I walked into the room, I could see a reel-to-reel projector and a projector screen set up. All I could think was my dad had got himself a girlfriend.

"Sit down and I shall make us a cuppa" she said softly.

I sat down looking around and could see all the photos of me and my dad but none of my dad and a woman and he never mentioned he was seeing anyone which I thought strange because we talked about everything or so I thought.

She came back into the room a couple of minutes later with two cups of tea, placed one on the small table beside me and sat in my dad's armchair putting her cup on my dad's coaster.

"Is my dad, ok?" I asked sounding a little worried.

"I am fine son, but you have caught me right off guard, I did not want you to find out this way that I am a crossdresser and have been since I was a teenager."

What the fuck, this woman is my dad? Well not a woman then actually but he is dressed like one, and quite a good looking one at that.

"I don't understand, why have you never told me before?" I asked him, looking straight into his eyes.

He went on to explain that his crossdressing is why he and my mom split up, that he found he enjoyed dressing like a woman from an early age and he was also a bisexual, and my mother could not handle it. I listened to his story for a good two hours.

"Do you have any questions, Tim?"

I had many, oh so many, like what do I call him now, dad or mom? What name does his lady form go by, does he have sex with men dressed as a woman? Why have I never seen him dressed this way before or even noticed any women's clothing when I have visited.

He went on to explain that I could call him whatever I was comfortable with, people call him Kathleen when he dressed this way, yes, he has sex with men and women dressed as Kathleen. We spent another 2 hours firing questions and answers at each other. He apologised for not telling me years ago, but he did not want me to stop seeing him or loving him. I assured him that would never have happened.

We stood up and hugged each other and I could smell his perfume which was quite erotic, and my hands ran around his figure-hugging dress to hold him/her.

I was not sure what I was going to refer to my dad as, but I did want to make him happy.

"I shall make us another cuppa" I said stepping back.

"Would you like me to change?"

"No, this is your home, and this is your way of life, I am sure I will adjust, Kathleen" I smiled.

She smiled back and I could see a tear in her eye. "Thank you so much son or should I call you Tim now?"

"Son of course, as that is what I am to you, mom?" I turned and went into the kitchen and put the kettle on. I could hear my dad/mom crying, I went back into the living room and pulled her to her feet and hugged her kissing her cheek.

"Please don't cry, at least it is all out in the open now and we can live together as mom and son from now on" I said reassuring my dad that I had no problem with the situation at all.

She pulled me closer and kissed my cheek and said thank you son, you are the best son any parent could ever wish for, As she squeezed me closer I became aware that she had breasts, my mind was now wandering if they where real or fake. A question for another time.

I returned to the kitchen and made the drinks, aware that my cock was twitching and growing in my boxers. What the fuck is happening. I handed my new mom her drink aware that my erection was obvious and sat down quickly.

"You ok son?" she asked.

"Yes, I'm fine, feeling a little knackered to be honest" I replied.

"A little horny more like by the size of your bulging jeans" she chuckled.

We had always had a very open relationship talking about all subjects including sex, which is why I was so surprised my dad never told me he always wanted to live full time dressed as a woman, but he/she was not wrong I was feeling horny and no idea why, but my cock was raging and begging for attention.

"You have had a long day, why don't you go to bed, and we can start fresh tomorrow" Kathleen said chirpily.

"I think I will" with that I got up my cock still tenting my jeans and went to my room retrieving my bags from the hallway on my way.

I stripped off and flumped onto my bed, my room was always how I left it, but tidier. Thoughts racing through my head about what I had learnt about my dad, and how he looked dressed as a woman, which was quite convincing actually even down to the low feminine voice and he had a good body to carry off wearing the figure-hugging dress. Without realising I was stroking my cock through my boxers and a small pre cum wet patch had developed, I still had no idea why my cock was so hard, but it needed attention, I pushed my boxers down to my knees and my penis sprang to attention pointing straight up my flat stomach.

I took it in my hand and slowly began working up and down the shaft, while my other hand played with my nipple which always gets me going. I did not even need one of my porn mags I was so fucking horny. I jerked my cock several times then moved my hand to my balls, fondling them and pulling my ball sack before returning to wanking my cock, I was soon shooting cum onto my chest my hips bucking with each spurt, as I started to calm down, I scooped up my spunk and licked it from my fingers until I had cleaned up every bit I could find.

I pulled up my boxers and headed towards my door which I suddenly realised was open as we never shut our doors, 'shit I hope I wasn't making a noise' I thought to myself entering the dark hallway. As I turned towards the bathroom my dad's door was open as always and I could see a low light and assumed he was reading, how wrong was I! I stepped back quickly so he did not see me and peered through the gap in the door and could clearly see he was masturbating, his cock looked about the same size as mine around six inches long and medium girth I suppose. He was letting out small moans as his hand jerked up and down, I was mesmerised watching him, I knew I should have just gone to the bathroom or back to my room, but I was here now and wanted to see the outcome of his wanking.

I saw a hand reach to the bedside cabinet and pick up two objects, one looked like a cock and the other a tube of something, he squeezed the tube into his hand and rubbed the it all over his shaft, and then applied more from the tube to his hand that then reached down between his legs and he raised his butt up, then he covered the penis looking object and this too went down between his legs, I heard a soft groan as he seemed to be pushing on the object in his hand while his other hand was back stroking his cock. I watched on for another seven or eight minutes before I heard the familiar breathing sounds of an oncoming cum shot and sure enough his bulbous red head spewed out stream after stream of his jizz into the air, landing on his chest, his face and over his hand. That was a lot of cum I shoot nowhere near that amount. I then watched as he scooped up his cum and took it in his mouth, 'wonder if that is where I get it from' I wondered. Then I saw him reach to the bedside cabinet again, this time getting some wet wipes and started to clean himself and his toy. I thought I better leave the bathroom visit until later and get back to my room in case he notices me.

As I lay on my bed again going through everything from the day, I decided that if being a woman is what my dad wants then who am I to reject him, he has always been a great dad and role model so from now on I shall call him mom and always refer to him as her. I just want my dad to be happy.

Sorry for the length of this opening chapter but I wanted to set the story.

Chapter two will improve, if you the readers want to hear more that is?

All involved are of legal age, 18yrs old or more.

This is a fantasy story to entertain readers.

Please rate this story
The author would appreciate your feedback.
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14 Comments
BrendaNWBrendaNWabout 2 months ago

Certainly chapter 2 .. please 🤗

AnonymousAnonymousabout 2 months ago

yes i want to hear more lots more yes it happened to me it wans't my dad who was the crossdresser it was me i was wearing my mams sexy see through baby doll nighty suspenders nylons i was laid on my bed on my back my legs wide open my cock rock hard i was rubbing my cock slow enjoying it my bedroom door was wide open my dad was looking at me his eyes all over my body he was licking his lips to me i saying soft i know you like looking at me daddy you want me don't you, he just nodded his head, come in daddy take your clothes off be naked with me i'll be your wife you can call me mam if you want to.

yes your new story yes crossdressing son babydoll nighty suspenders nylons daddy loving his sexy son

Bisexual_4_all_pleasuresBisexual_4_all_pleasuresabout 2 months agoAuthor

To everyone who's upset I didn't put chapter 1, my sincere apologies that it ruined your reading experience. This is my first time writing stories, a bit of gentle guidance is all that was required, not the arsey comment of immediate rating of 1 from someone who is anonymous which rates them as a ZERO in my book. No one forced you to read my story.

AnonymousAnonymous2 months ago

Very special story and a perfectly paced start. Kathleen certainly made a special impression. It’s easy to imagine how forcefully he must have cum…lovely description of that too.

JT

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