MY BRA, NOW FOREVER

I knew I loved wearing panties 24/7 and a bra only at home, but I never knew my new girlfriend loved me wearing lingerie even more. She is so sweet and we have so much fun buying and talking about lingerie. We are the same size, little over weight but who cares. I love my B cup man boobs and so does she.

She encourages me to wear a bra in our apartment (and outside if I dare) and rewards me for that. I think all my neighbors know I wear a bra at home. Many times she encourages me to “show it off” under a see-through t-shirt. I am a little nervous about see-through tops around the apartment complex, but no one seems to care. In fact our neighbors, two guys, I think, wear bras too.

Oh well, here is my story on how Cathy lead me down the path into a new person.

“John lets go shopping tonight and buy you some pretty bras, what do you think? Your bras are just so plain and offer you no support or shape”, Cathy said.

Not sure I want more shape, don’t want people knowing I have boobies or that I am wearing a bra, I thought.

“I would love to go shopping but can we go to a different store other than Sears?”, I asked.

“John you know they have the best service and they have our plus size bras. Plus Sally is there, a very good friend and she needs the commission. Besides I have a treat for you there now that Sally starting working there and Sally can help us”.

All day I was wondering what Cathy meant “a treat” at Sears?

After dinner Cathy said it was time to go and have some fun girly shopping. As I tried to go upstairs to take off my bra, Cathy stopped me saying, leave your bra on, no one can see it, be a little adventures. I was nervous going to the mall in my bra, but she always knows best. Plus I really really like wearing bras and panties.

Off we went, I was excited and nervous. I looked down at my chest and I could not see my bra, I did have little “bumps” there to, which I liked.

Sally greeted us at Sears with a big smile. What was that all about? I don’t think she knows I wear bras, but something was up.

Cathy grabbed my hands and said, “Sweetie we are hear for you and your first professional bra fitting and Sally is going to help you. We want to give you a pretty new figure and show your femininity.”

I quickly pulled Cathy aside whispering to her, “Does Sally know I wear bras?”

“Yes, sweetie and she is excited to help you today.”

I looked back at Sally and her big big smile said it all. I was in for a professional bra fitting. I always dreamed about being measured for my own bras, but never had the nerve to try it. Will I have to take off my shirt for her to measure me?

The girls ushered me into the back dressing room and told me to take my ugly man shirt off. Sally saw my bra and I was embarrassed.

“John don’t be embarrassed, I have fitted many men with pretty bras. I do have to say though your bra you are wearing is not very pretty. It is very plain and has no shape, no support. You need my help, girl! You do have natural boobies I see, how sweet. I just love men with man boobs! We will improve your look with a pretty supportive bra today”.

I looked back at Cathy and she was smiling too. I guess I was in for a treat. After Sally measured me with her tape measure, she announced my bra size, which I already knew as 46B.

To my embarrassment Sally asked me if I am taking pills to help develop my figure. She was saying my breasts are well developed for a man and seriously needs better support. I was speechless with embarrassment, I told her my breasts are all mine, all natural. Because of my size, I think I started wearing bras years ago, told her.

Cathy popped in saying there is room for a better shaping bra like a t-shirt bra and some extra help.

What was the extra help?

With a big smile, Sally said she has just the help I need, be right back.

Sally returned with a gorgeous pink lacey padded bra. I was melting with excitement. The bra was so pretty and lacey. I just love the little flower between the cups, so dainty, I thought. In Sally’s other hand were inserts, I knew what they were and always dreamed of buy them to help fill out my cups.

Always dreamed of wearing a padded bra with inserts so my bustline would look pretty and feminine, like other girls. I look at all the girly sales catalogs, wondering what it would be like to wear a padded bra like those pretty models.

Cathy popped in saying perfect; this bra will give you such a sweet pretty figure now, you will love the support.

“Take your old bra off John and lets slip your new life on, dear. This bra will make you feel like a real princess”, Sally said.

What did she say, new life, what new life?... it’s just a bra.

Wow, slipping on this soft bra, hooking it in back made me feel so different. I just love the three hook bras.

Sally looked at me smiling saying, “You know with three hooks, you know you are wearing a “real” bra. How does the bra feel John?”

Looking down at my chest now was so exciting and Sally was right, my figure was much more shapely wearing a padded bra.

“John always remember to bend forward and adjust your breasts into your cups. Your bras will fit much better and your figure will be much prettier too!”, Sally said.

Sally adjusted the straps, pulled on the band and said, “even though this is a t-shirt bra with a little padding, you still are not filling out your cups. Let me try this other bra on you, it might fit you better”.

Wow, this other bra was really shaped, what I call a hard cup form bra, has three section cups making my breasts somewhat pointed and again soft pink and tons of lace. I loved the shape and projection. I never had such a large bustline. I wonder how it will look under my shirt?

Still Sally said I need the “extra help” in my cups.

“Here are little inserts so help you fill out your cups, dear”.

She slid in the inserts and like magic my cups were filling out and felt much more comfortable. My smile showed my excitement and the girls knew it.

I thought I was going to cry with excitement.

All of a sudden both Sally and Cathy gave each other a high five saying how perfect my new figure looks.

I knew my bustline was bigger now with all this padding and I was worried my neighbors would see my two mountains on my chest. How could I cover these boobies up I thought?

I did admire my new look in the mirror though. Cathy hugged me saying, “I think we found my Sissy’s new pretty padded bra, giving her a new look.”

What did she call me? Sissy what is that name all about? I was so excited about my new bra, I didn’t ask her what she meant. Plus I sort of liked being called a Sissy. Wearing a soft pretty bra like this is what Sissy’s do I read somewhere.

“John, you know now with a pretty figure, like yours, you might have to wear women’s tops, you know with darts to help shape your clothing with your new larger bustline”, Sally said.

Fear struck my face as Cathy popped in saying, “John don’t worry about new tops. We are the same size and we can experiment at home with more feminine tops for a better fit. I think my Sissy would like playing dress up now with Sissy’s new figure”.

“Cathy, how can my bustline be bigger and I am still wearing my normal size bra, 46B”, I asked.

Sally popped in saying, “It’s all in the fit and the bra we selected for our new Sissy. Don’t you just love your new shape? Soon Cathy might get you a bigger bra like a C cup bra. I think my new Sissy would love that, right? ”

All of a sudden the thought struck me, maybe Sally put me in a C cup bra now. That is why my chest looks so much bigger. Wow, the problem is I think I like my bigger bustline.

Things were moving way to fast for me as Sally gave me some water and told me to sit down and enjoy the experience.

Cathy sat with me as she put her arm around me telling me she has another treat for me!

Sally brought out a matching long leg pink panty girdle with garters. I always wanted to wear a girdle and got so excited. I giggled saying, “Look here the same small pink flower between my bra cups is on the band of the girdle. How sweet is that, I love it! But, Sally, why is there padding on the hips and butt in the girdle? Is the padding there for what I think?”

Cathy popped in saying, “Yes John, we want you to have a girlish figure and you know you need extra shape on your hips and butt. This special girdle gives us girls the little extra help we need to look pretty, much like the little extra padding in your bra cups, all helps our shapes and makes us girls curvy”.

Both girls commented on how excited I looked and thought my new girdle would top off my lingerie with a very pretty shapely figure.

“Slip off your ugly pants and slip on your new girdle, John. I think you should wear your girdle every day now, so sweet”, Cathy said to me.

“Cathy this girdle is way too small, I can’t pull it on, too tight”!

“Silly Sissy, that girdle is just right, this size will help mold your new figure, like all us girls have to wear each day. Getting pretty is hard work, but we love it, right?” Sally said.

“Does Sissy like all her new foundations? I think Sissy would like to wear her pretty foundations all the time now, right John?” Cathy asked.

“Cathy I can’t think straight, what did you say, wear this bra and girdle all the time, everyday? How can I do that?

“John, all my previous boyfriends wear their lingerie 24/7 and no one cares. They are changed people, they are the soft Sissys they always wanted to be. Deep down, I think you want to be the most feminine Sissy you can be. We can help you dress and no one will know you are wearing a bra, girdle and nylons. You know you want to wear lingerie 24/7 and be as pretty as possible. Tell me the truth sweetie, let yourself go, express your true feminine feelings, I love you and your feminine side and will help you become the Sissy you have always wanted to be!”, Cathy said.

With huge burst of emotion and crying, I hugged Cathy saying, “Yes, yes, yes, I want to feel and be feminine in these new bras and girdles. Please help me be the Sissy you want me to be everyday, 24/7”.

I grabbed Cathy whispering in her ear, “I think I am leaking down there, I was so excited. I am afraid I might get my panties and my new girdle all wet. What should I do? Help!”

“John, this is so sweet, I think you need this, holding up a feminine pad, this is made just for us girls for just this feminine problem. You are quickly becoming one of us girls. I love you. Here let me show you how to wear your feminine napkins to protect your clothes and things”.

I could not believe I was wearing a feminine napkin, protecting my new girdle that the girls want me to wear all the time now. This is moving way to fast.

“Sally, his new pretty lingerie did the trick, our Sissy is all ours now and we will make him so cute and feminine. Lets get him into his nylons. John needs to learn how to garter up his new nylons everyday, just like us girls do.”

Slipping on my new girdle and nylons changed my whole being. I felt so relaxed, so soft. Sally brought out a new feminine top and as I slipped it on I could see my lacey bra under it. The pink top was a tight stretchy top showing off my new figure. As Cathy threw my old man shirt in the trash she said, “Out with the old and in with your new life John”!

“Cathy you can’t throw my shirt out, I need it to go home. I can’t wear this see-through girly top home”.

“John, get real, your old shirt will not fit you with your new figure. Look at your bustline, you are bigger up there now and your old shirt is way too small. Plus you look so pretty in your new padded bra, I would think you would love to show off your new figure in the feminine top”.

“I can’t go outside in that top, everyone will laugh at me. I am not ready for this change as much as I love it”.

“John you run around our apartment complex many times showing off your bra under thin t-shirts. No one there laughs at you nor says a word. You will get use to wearing such pretty clothes now. You know you want to!”

“Cathy what do you mean, “wearing pretty clothes NOW?”

“John look at yourself, look at what you are wearing! Look how excited you are to wear these pretty items. I bet you would love to wear them all the time and I bet you would love to wear them with clothes that fit your new figure!”

“Cathy wait, next you will want me to wear a dress”?

“John you said it not me. And yes, I think with your new figure, look at you, you would look smashing in a pretty dress; you have a perfect figure and perfect feminine presences. Deep down I think you want me to help you become more feminine and guide you into our women’s world.”

“Oh sweetie, don’t cry, you know you want this. See you even crying like a Sissy. With my help you can become the Sissy you have always wanted to be!”

“Here put this pretty top back on and your pants, if they will fit around your hips, and lets go home and talk this all through”, Cathy said.

I could hardly pull on my pants over this padded girdle. I really had to pull them on, was hard to button them closed.

“Cathy, I can’t fit into the pants with all this padding, help”!

“Silly girl, you look perfect, shows off your new figure. That is the way us girls wear our pants, very tight showing off our pretty figure, get use to it John. We will have to buy you some women’s slacks so that they fit better.”

Cathy reached into her huge purse pulling out my high heels from home. They are my favorite heels but only for home fun. She told me to put them on and that we had to get going.

“Cathy, I can’t wear my heels outside, they are only for the apartment.”

“John, get real, first you love those heels, and second your figure demands high heels, trust me you will look stunting.”

I slipped them on, and wow, they really put my walk in a different swing. My hips moved and I really had a bounce to my new breasts. I loved the way my feet slipped into the heels with my nylon’s on. Never had that feminine feeling before.

All these new feminine feelings, padded bustline, my breasts bouncing, padded hips, nylons; wow I think I love all these new girly things.

For some reason, Cathy has a spell over me, I always do what she wants. As I walked out of the dressing room, I looked in the full-length mirrors. I loved what I saw. Yes, I could see a little of my bra straps and for sure a shapely bustline, but I thought, so what, I like it!” I walked into the store and yes other women saw me, but they had no reaction. Good thing I knew how to walk in high heels.

We paid Sally as she gave me a big hug saying, “John hold your head up high, you will make a wonderful Sissy, be a proud Sissy and enjoy. Cathy knows best! See you next week and we can have some more fun shopping. You will learn Sissys love shopping”!

“Thank you Sally, I hope I can handle all this!”

There was another clerk in the lingerie department, as we walked out she grabbed my hand slowing me down and with her big smile said, “You look wonderful, love those heels, you are so brave, I hope my boyfriend can be just like you”!

Walking out to the car was a very different feeling. My chest was bouncing and it felt wonderful. Something I have only dreamed about. I said to Cathy, “my boobies are bouncing, can you notice that, should I cover up?”

“Silly boy, you look fine. That is the look Sissy’s want, you will get use to your new bounce and your new walk. Before long you will not even be aware of your new feminine bounce”.

I was picking at my bra straps, seems to be too tight, I thought. This new bra felt so different than my old bras.

“John stop adjusting your bra straps in public, it is not very lady like. If you don’t want to bring attention to your bustline, don’t picking at your bra straps silly Sissy”!

“I know Cathy, but this new bra feels funny, too tight”.

“John you were professionally fit for your bra, this is your right size and fit, get use to it, sweetie!”

“Ok, but Cathy I am also thinking how will I do my running with my breasts bouncing all over?”

“John, our next shopping trip we will get you a supportive sports bra and you WILL get use to your bounce. Trust me, now you will NEVER be without a bounce to your step, so sweet!”

What does she mean, never be without a bounce now, I thought?

We got home and into our apartment without running into our neighbors. I was concerned that I thought my inserts in my bra were getting warm and felt different. I asked Cathy why.

“John, Sally gave you a new Sissy insert. Your new inserts expand, get bigger with your body heat and expanded in your cups to fill your cups out and give you an expanded shape. Sounds like it is working, so sweet. Don’t you just love it?”

“Cathy all this is happening way to fast. I am not sure I can handle being your full-time Sissy. I mean I love wearing a bra, but a girdle with nylons and insert in my bra cups might be too much for me. Next you will have me in dresses and makeup.”

“John, I think you will learn to love my help. I think you know you are a Sissy and want to become the most feminine Sissy you can be. I can help you if you let me. You are truly sweet and you just need to let yourself go and listen to me. Can you do that, let me pleasure you in your deepest desires?”

As tears ran down my face, I felt so confused and happy. I knew I wanted to place myself in her loving hands, as I said, “Cathy, I am all yours, take me away to my new feminine lifestyle”!

We both hugged as Cathy playfully snapped my bra strap giggling away, saying, “John, you are all mine now, you have come to the other side, enjoy sweetie, we will have so so much fun feminizing you now”!

THE END and the beginning of my new life, I wish!