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Step Daughter Figured It Out For Me

Categories Fiction, First Time, Reluctance, Transsexual

Author: 50and7

Published: 24 August 2018

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Genetics are a bitch, I remember from my youth that my grandmother had giant breasts. When you are a kid, and she is coming at you to give you a big hug and kiss, her breasts just are enormous and swallow you whole until she releases you.

Later, I see that my mother is also ginormous. She is not overly over weight, but her bras on the line just caught the wind and exploded in a giant sail. And then, my sister was also so big that she had to have a reduction just to be able to walk normal.

So, I shouldn’t be surprised that I also have huge breasts, but I am a male. My breasts were always big growing up, so big that a doctor checked my genetics, and checked for a disease called gynecomastia. Which I didn’t have, just had a big chest. In High School, they were so big it hurt when I got hit in the chest in football because of the shoulder pads pinching down. I won’t go into the teasing here, that is another story.

This story takes place much later in life. I married a woman who had a young daughter, just turning 10. She was a great kid, but her mom didn’t teach her manners too much. So, the first thing she said when she saw me with a white t-shirt on was “Mom, why does he have breasts like you? I thought boobs were just for girls?” I don’t know how she explained it, but it didn’t stop her from keeping up talking about it all through her teen years, and into her 20s.

She would come up to me and ask if I was comfortable. I would say sure, why, and she would ask if I was in pain from my breasts not in a bra. I would just turn back to what I was doing and ignore it. Or she would come up from behind me and grab one and say “Hmmmm, I think a C”. I would yell “Cut it out” and go about my business. Then once, she came into the house early home from school. I was walking from the kitchen to the bedroom without my shirt, and she just stared. I stopped, looked at what she was looking at, and then started walking briskly, covering my chest like a woman would.

But I wasn’t fast enough. She ran up and said “yep, big B or a C. Just admit it, and let’s get you measured”. I said no, and pushed past and got into the master bed room and shut the door.

Now let’s fast forward. My marriage was going downhill, and I found food to be the only thing that made me happy, so I started gaining weight. But, unlike most men, the first place I put on weight is my chest and legs… yeah, just like a woman. Well, I wore sweatshirts, and big bulky things to keep my daughter from really noticing them. I would avoid her except when I was sitting down, and when I would hear her coming I would evade as quick as I could.

Fast forward a little more, I move out. Soon, my step daughter asks if she can move in with me because she is experiencing the same thing from her mom. I would never refuse her in this and gave her a room, and I slept on the couch. It’s nice. She is a great roommate. Cleans, cooks, doesn’t bring weird people home. I am loving it.

One night, she said she has some booze and wants to know if I would share. Sure would! We sat on the back porch and drank quite a few. I was getting warm and took off my sweat shirt, and she saw my larger breasts for the first time for real. Being a couple of sheets to the wind, she said “Dad, really, let’s just see what size you are. It’s just you and me. Let’s do it.” I said “You are never going to let this go are you? Fine, if this will get you over this, let’s do it.”

She goes in and grabs that floppy measuring tape from her sewing kit. She makes me take off my shirt, and puts the tape around my body, just under my breasts. She then puts it under my arm pits, then measures around the fullest part, over the nipples. “Jesus Dad, you are a double D! I never thought you were that big, but I…” and she measured me again. She sat down, pulled out her phone (I thought she wanted to take a photo) and typed something into it. “You didn’t tell someone did you?” She said, “No, just wanted to make sure. A double D dad. That is awesome!” “Well if you think so.” I said. “I’m going to bed”. And walked off to her protests.

A couple of days went by and I didn’t think another thing of it, and she hadn’t mentioned my breasts since then. I thought we were all done! But, one night, I fell asleep in a lounge chair in the living room. I was awoken to her rustling through a bag and I asked what was up. She said “I got you something!” all sweet and cheery. She pulled out this beige bra with a red lace over it, and it was way bigger than what she would wear. I just stared, still kind of sleepy, and she said again “This is for you, Dad. Just try it on, you will see how much better you feel”. “Fuck, I thought we were over this.” I said. She said “Dad, we can wait until I get you drunk again to get what I want, or you can just do it now” as it dawned on me she had that booze so I would let her measure. Fuck. What a manipulative little minx.

I sat there, thought she has already seen my breasts naked, what is the difference. So, I said “Ok, sure”

She must have jumped three feet in the air and yipped! “Stand up, and take off that sweatshirt” So I did, and the t-shirt underneath. I was now just standing there in my shorts. She walked behind me and wrapped her arms under my arms around my chest. I felt really weird, but didn’t stop it. I was in it to finish it.

She told me to put my hands through the straps, which I did, and she then pulled the strap tight behind me. It was pinching and painful. She came in front of me and said, “Oh, bend over” so I did. She slid her hand in the side of the bra, around my breast, and pulled and my breast just dropped into the cup. Then she did the same thing with the other side, and the pinching and pain just went away! “Ok, stand up”. When I did, she had the strangest and oddly proud look on her face. “So much better than I had expected!” Let’s get over to a mirror!

Walking over to the mirror, I can feel my breasts just jiggle and jiggle inside the bra. But, strangely, I could breathe easier, and felt my back pain ease a bit. Then I saw myself. I had a real pair of breasts! And to quote Seinfeld, they were amazing! Me! With better breasts than my daughter, or my wife!

She stood there, looking at the mirror, at me, at the mirror. And said “That just won’t do. Come on” She grabbed me by the hand and we walked into the bathroom. She rummaged around in the cupboard and came out with some Nair hair removal. Now we are crossing a line! No way. No Never.

“Dad, what, it will grow back? Who sees you naked now, well except me? You have gone this far, and if you don’t like it, it will grow back! Hair always does”. I had to admit, she had a point, and I kinda wanted to see just how much better my tits were than my X’s.

She went behind me, unhooked my bra, and whispered “never unhooked someone else’s bra before, crazy” under her breath, but I laughed out loud, but she was all business. She had me wash up my chest and shoulders, and she washed my back. She then spread this stuff all over my chest and stomach, shoulders, and then my back and arms. While I was sitting there getting chemical burned, she went into the other room and wrustled around in a bag and brought back another… thing. We then washed off the Nair, and hair, and I faced me, with a nice set of breasts, clean and softer than I would have ever expected.

She said “Perfect! Nice, they look beautiful Dad” which was an odd sentence to hear. Put this on first. It was something stretchy, that she explained that I needed to step through feet first through the neck part.

And I had to take off my shorts.

“Honey, come on, this is going too far”. “No, Dad, I have to see this through! I have been thinking about this since I was 13, and now that I have you this far, we need to finish it. Do it.” “Ok, get out of here.”, which she did and I put them on.

It was a super confining garment that made my thighs way smaller, my butt poke up and out, my waist cinched in, and then had straps that let my breasts open and dangling. God Damn did they look bigger and fuller in this thing. “OK, I have it on” I said, and she came in. “Adjust your penis between your legs dad. Having it pushing down the leg ruins the illusion” and I fucking realized this thing was mostly see through. I quickly pulled down the garment, and adjusted as she asked. It was a little uncomfortable, but in the end, I see what she was saying.

She gave me the bra and said “Put it on under the foundation”. “Um, I don’t know how” I said. She looked at me like she was frustrated, and said “Yes you do, I just showed you!” So, I thought about it, put the straps on, reached around and fumbled with the little hooks, but eventually got them, and then did the bend over and pull with my breasts in the bra.

Standing up, I looked at myself and I saw a woman in the mirror. No makup, short hair, but my body was a woman’s body. I have an hour glass, I have a nice ass, I have no bulge. And I have huge huge boobs!

“I’m so glad you like it dad!” and I realized I was getting hard seeing myself in the mirror. “I would be turned on my you too if I was you. You are curvier than Mom ever was, and with your tits on display, I think every man would love you!” “Oh my God, honey, don’t look at that” I said meekly, which she answered “Dad, I have seen a few, don’t worry. Now, look at yourself! Isn’t this exciting! YOU ARE HOT!” And I had to admit, I was.

I loved how it felt, how I looked and feeling superior to my wife. But, I started telling my daughter that I was good to go and take it off. She insisted that I keep it on for a while, get used to it. If I didn’t like it by the end of the night, she would take it back. So, ok, I kept it on pretending I didn’t want to.

I wore it under my sweatshirt and shorts for the rest of the night. I couldn’t help glancing at my profile in the mirror when I walked by it, caught a glimpse of it when I passed a mirror, and how kind of in my way they were when I was just doing normal stuff. I think I was hard for 6 hours.

Late that night, sitting on the porch, in my bra and girdle, drinking wine, I admitted to her that this was amazing feeling. I loved it. I felt to put together. My back didn’t hurt when making dinner, and I liked the binding feeling of the girdle. “Good dad” was her only comment and was silent. I found that odd, and asked if she was uncomfortable with me? And she insisted she loved it, insisted I keep it, but she just had some other things on her mind.

The next day, I awoke, and put on the normal old clothes. They felt funny being hairless, but I didn’t feel I should wear this outfit over the other stuff today. That I may not even wear them again, but it was great when I did. During the morning, I got a call from my daughter to come down to the mall, she needed my help. I smelled a fish, but I thought I was in for a penny, might as well go in for a pound. And I was right. She was at “Womans” store, and had a bunch of stuff in the back ready for me to try on. I looked at the sales lady, and she was non-committal on me going in and trying stuff on. So, my daugher grabbed my hand, and we went in the back with all of the other women trying stuff on.

First, I tried on several bras, one was so pushup that I thought I could rest my chin on my breasts. Of course, that was going home with us. Next, she put out the panties, and form fitting body garments that required me to take off my pants. I stopped, looked at her, and she whispered “I saw it yesterday. And I have seen them before”, and started grabbing for my shorts. I pulled them down, and stepped out of them. Thanks to trying on the bras, I was partially hard as I was still wearing that extreme pushup. “Nice Dad, well done” and pushed the panties into my hands. The softness of the panties were nice feeling against my cock, and I adjusted it the way I had before. “Mmmmmm, no” and she made me take those off, for another one. This was a thong. I put it on, tucked my cock, and she pulled the thong up in my butt crack and that made my cock almost disappear. “That’s what I was looking for, and we are going to have to Nair you butt crack dad, and get you a trim up front”.

After what seemed like a month, I went away with a dozen or so items, for way too much money, and this included a form fitting dress, hose, and shoes. And my daughter beaming from ear to ear! “We are going to have so much fun tonight!”

That night, she had me put on the girdle and mega pushup, with the thong underneath to hide my ever present hard on. I put on the thigh highs, and shoes, and she made me walk around for a while to get used to them, which took some time. After a couple of hours, I sat down, and she was walking around the living room, sort of pacing, when there was a knock at the door. Oh shit! I need to get out of here! But it was too late. She went to the door, and in came three of her girlfriends. They all stopped and looked at me, standing there, shocked, and all of them smiled. “Fuck, Melissa, too bad you are not related to him. You could have had great tits!” one of them said, and they all agreed. Melissa came over to me, grabbed my hand, and said “You know the girls, right?” I said “Yeah, but not like this” and they all laughed. “Well, Dad, they will know you more later!”

I wanted to run away. Hide. Anything to stop feeling ashamed. Then one of the girls, grabbed my hand, and said “Don’t worry. I love it. We love it. And we can’t wait to help you go all the way.” Which calmed me down and I began to flow in the evening.

The next two hours was a marathon, I put on the dress (never taking off the shoes), and they all worked on softening me up. Makeup, hair, nails, and general walking guidelines. And they all agreed that I shouldn’t talk much when I am dressed. I then talked about the elephant in the room and said “Where are we going?”

On our way to Napa Valley, with my daughter driving, I was trying to adjust the seat belt around my breasts. It was just weird, it didn’t work anywhere. One of the girls in the back said “Get used it!” and they all laughed. Life was going to be strange going forward.

We went to a dark wine bar where there were men my age, and women of all ages, so we all fit in. I walked to the back, practically stumbling on my way, and I could feel the eyes on me as I came out of the near catastrophe. Some lingered. I sat down in a booth, and the girls came in and surrounded me. A waiter came up and asked what we would like. I let Melissa do all of the talking for me, but noticed that the waiter looked from girl to girl, to me, looking at my tits more than anything else here while he was jotting down what we wanted. I felt my daughter’s friends elbow hitting me in the ribs when he was staring extra-long. I have to admit, I felt good that I got the attention and the girls didn’t!

We drank, we talked, we got tipsy. It was a great night! I felt great, and loved this feeling of being with new friends. And, I found that the girls don’t really talk any differently than boys! Near the time to go home, the girls got up to go to the restroom. I would never be able to figure out how to get out of this easy, plus the thoughts of going into the girl’s restroom was just too much for me right now. But, I should have thought more about it.

Sliding into the booth was a relatively good looking man, who was drunk, but smelled like a good cologne. He got really close, and said “I noted you sitting here by yourself. Where are the younger girls?” “The restroom” I said quietly, and in as womanly voice as I could. “Well, I will keep you company until they get back”, to which I didn’t say anything except take another drink of my wine. I could feel the heat pouring off of him, and could feel the muscles through his shirt. I also noticed that he kept looking at my full exposed cleavage, loitering there for long periods of time, while he discussed the wine he was drinking. Then it happened, his hand went to my leg and up my thigh. I just took a drink and didn’t say anything for fear I would sound like a man! He rubbed it back and forth, every rub getting closer and closer to my thong. And with the soft silky dress against the hose, being rubbed urgently, I started to get hard. He couldn’t touch that!

So, I reached down, and put my hand on his hand. He grabbed my hand and put it right in his crotch! And what I felt was incredible. He was big, it was curled down his left pants leg, and I was holding right onto it! What could I do? I had to start rubbing it so he wouldn’t touch my hard on. He said he loved that, and started nuzzling his face against my neck. Slowly kissing my neck, nibbling on my ear lobe, and I could feel his cock getting harder. It was impossible to stop; if I stopped now, he would concentrate on my leg, and… I, amazingly, wanted to see how big this thing got!

The girls decided to show up right then. “Ok, ok, Ill go, but here is my card” he said out loud so all the girls could hear, then he whispered in my ear “Next time you will have to show me how you have those amazing breasts, and let me reach your cock, huh?” I looked at him, shocked, and he whispered again, “The way you walk, it is a sure give away. Call me” and he got up and left.

The girls all giggled as I stood up and straightened my dress. Melissa said “How was he? Did you touch your first dick tonight?” I said “He knew!” She replied “Of course, you were so graceful coming in, and we still haven’t fully trained your body. That’s why we chose this bar. They would all be ok with a man in a dress.”

I have a lot to learn.

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Step Daughter Figured It Out For Me

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Comments (1)
Greendragon — 25 August 2018 12:41
This story nee a chapter 2
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