Story of Michael and his breasts leading him to become Gwen! My first attempt at a story.

Becoming Gwen
By
Kathy t

Michael throughout his childhood was overweight in middle school he started to develop a bit different than other boys becoming a bit chesty. In high school and college, Michael began working out and even went on a diet hoping to lose weight. Michael was able to slim down dramatically but here at 23, the only problem is his chest remains except now it is more pronounced and seems to be getting bigger. He would feel his chest bounce when he walked very sensitive nipples always showing and even gave him back pain. Michael decided he needed to get this checked out so he scheduled an appointment with Dr. Walker.

Dr. Walker brought him in and she immediately noticed Michael’s assets. Michael explained his situation to her and was asked to take his top off for further examination. Dr. Walker looked shocked seeing how developed Michael’s chest was and said: “I’m not sure how to say this Michael but you have breasts.”
“Breasts!” Michael said “I’m a man I can’t have breasts” he shouted.
Dr. Walker sat him down and explained “Michael it seems you have a condition called gynecomastia. And in your case, it may be quite severe. I would like to do some blood work to test for estrogen”.
Michael was in disbelief.

After blood work was taken Dr.Walker asked Michael “Have you ever considered wearing a bra? At your size, I think it will be a benefit for you and help with controlling your bounce and pain you have been having.”
Michael all upset shook his head saying “Dr. I can’t wear a bra, those are for women, what would everyone think?”.
The doctor responded, “Bras aren’t for women, they are for people with breasts.” “Please think it over. I will give you a call when your blood work is done.” “Remember there is no shame in getting support.”
Michael responded, “Yes ma’am I will think it over.”

Michael returned to his apartment still in shock about today’s events. He knew something was off with his body but didn’t think that. He thought to himself “Well having breasts would explain why I haven’t been able to lose any weight up there”. He wondered “How many people have noticed this about his body and why hadn’t anyone said anything”. As he got ready for bed he took off his shirt and looked in the mirror. He caught himself feeling his breasts with his hands and looking at them he had some white liquid come out of his breasts on his hands but staring at his chest he didn’t notice, He came to realize maybe the Doctor is right. I do have breasts but to wear a bra that seems a bit excessive I don’t think I could convince myself to do that. Maybe my friend Sarah can help me.

The next morning he gave his friend Sarah a text. Sarah and Michael have known each other since high school and she is one of his closest friends. “Hi Sarah, I really need to talk to you could I come over today?”
Sarah quickly responded, “Of course sweetie you are always welcome over”.
Michael was very nervous about approaching her on this topic but he knew he needed to talk to someone about his doctor visit and no way would any of his guy friends understand.

Michael going up the stairs to Sarah's apartment he noticed his breasts bouncing more than he had ever before became very self-conscious of all this movement.
He arrived at her apartment and was welcomed in with a big hug. Michael still self-conscious felt both of their breasts touch.
Sarah, a very beautiful redhead, happily “What up Mike!?”.
Michael said nervously “I went to the doctor and found something out about my body”
Sarah askes “Did you find out why you can’t lose that last little bit of weight in your chest?”
Michael responded, “Yes this is embarrassing to say can you promise you won’t tell anyone else.”
“Of course I won’t honey! You can tell me anything,” she responded.
“Well it turns out I have gynecomastia,” he said.
“What does that mean Michael?” she asks.
Michael all red says “It means I have breasts like a woman”
Sarah surprisingly excited “Wow! That would explain it. I have noticed sometimes your chest moves some like mine when I’m braless.”
Michael quickly “Really? Why didn’t u ever say anything?”
Sarah responded “ Well I didn’t think it was a big deal. What do you plan on doing now? Are you going to wear a bra?”
Michael embarrassed “My doctor suggested I do what do you think?”
Sarah responded, “Well let me get a look at you, you can try on one of mine.”
Michael “I’m not sure I'm a bit afraid of taking my shirt off.”
Sarah with a warming smile “Don’t worry Honey I’m not going to judge”

Michael took off his top revealing his breasts
Sarah looked in aw and said “Michael don’t feel upset but you have a nice pair of breasts”
Michael “Thanks I guess?”
Sarah left the room and returned with a purple Maidenform bra of hers.
Sarah had a decent breast size herself as she wore a 36B.
Sarah said “Let me help you put it on”

Sarah pressed the bra against Michael’s chest and told him to hold cups on while she hooked him in the back. Sarah then adjusted the straps and asked “How does it feel?”
Michael noticed a real difference and was a bit surprised “It is a bit tight but it feels pretty good.”
“Great sweetie you look cute in it! I think you fill it out a bit too much it seems like you're spilling out the top some.”
Michael confused “what does that mean?”
“Well, it means if I have to wear a bra then you should too. We will have to get you properly fitted.”
Michael in disbelief “I have bigger breasts than you. Oh man, what is wrong with me.” Michael begins crying. Sarah comforts him “oh honey its ok don’t need to be ashamed I’m pretty small size. You will be ok. My friend Jessica works at a boutique. I'm sure she would love to help you.”
Michael “I can’t go for a bra fitting what if people see me?”
Sarah “Don’t worry I’ll go with you and shoppers will just think we are shopping for me. We will have loads of fun!”
Michael agrees. Michael tries to take off the bra before going home but Sarah says “Leave it on honey you got to get used to one.” “Stay the night we will go see Jessica in the morning”

The next morning he was ready to head out with Sarah and said “Don’t forget the bra silly got to have some support” Michael freaking out “Won’t someone see.” Sarah responds “Michael people are going to notice your breasts either way at least this way you are supported. If you feel worried, throw on one of my sweat jackets.” Michael puts on one of her college jackets and they head out the door.

They arrived at the boutique. There was lingerie on racks all over. It was very overwhelming for Michael. Seeing the women shopping made him feel very nervous assuming they all were watching him.
Jessica, a tall busty blond woman, walks up to Michael and Sarah “Hi Sarah! You must be Michael I’m Jessica I’m going to take great care of you. I hope you're excited to get some bra and panties.”
Michael “panties?” J
essica “Trust me girl once you go panties there is no going back just ask my boyfriend”
Michael confused about being called a girl for the first time.
Sarah happily says “Ok Jessica let's get to the fitting room, Michael is currently wearing one of my 36B Purple bras I think it's a bit too small for him.” They head back into the fitting room.

In the room, Jessica said “Ok Michael let me see what I’m working with''
Sarah nodded as Michael took off the sweatshirt and his shirt. Leaving Sarah’s purple bra showing.
“Very cute bra,” Jessica said.
“Thanks,” Sarah said.
Jessica checking Michael out “Does look like it's too small for you Michael let me help you take it off.”
Jessica unhooked Michael and his breasts sprang free as the bra fell on the ground.
Jessica “Let's get you measured girl. You are too big to be going braless”
Michael turned red again still confused by the use of girl.

Jessica took out her measuring tape and wrapped it around Michael just below his breasts and then across the fullest part of his breasts.
Jessica said, “38C let me get you some pretty bras''.
Michael to Sarah “is that a big size?”
Sarah ``It is not that big but it's not small either. Jessica is 34DDD that is big.”
Michael ``yes she does seem much bigger than two of us.”
Jessica returns with 3 beautiful bras “Ok girls let's have some fun.”
Sarah all giggly “Michael this going to be so much fun”.
Michael responds “You two seem quite excited”.
Jessica happily“It is not every day you help your friend with their first bra fitting”

The first bra is a Playtex Pink push up bra
Michael asks “why do I want a pushup or pink bra?”
Sarah “Well just in case you get bigger you know what might look like”
Jessica helping him put it on “Pink because it is so pretty.”
The two girls both immediately said, “You look beautiful in that bra and it looks like a perfect fit!!”
Michael, you could tell liked the fit too.
Michael said “I can’t believe I’m saying this but this feels good, I feel some real support and uplifted”
Girls happily “Of course you do that what we feel. Welcome to the club!.”
“Thanks. Could I try on some less girly bras?” he responded
Jessica excited “Sure but they aren’t as pretty”.

The next bra Jessica brought him was a navy blue t-shirt bra Jessica explained it helps prevent nipple show in a t-shirt then lifted her top showing her beautiful and full breasts “I’m wearing one now”
Sarah immediately did the same “NO WAY! Me too!”
Michael was shocked by all of sudden how comfortable the girls were around him.
The two rushed him into trying on the bra. Now all 3 stood there topless in navy blue bras.
“Let us take a pic,” Sarah said, taking a selfie of the 3.
After a couple more tries, Michael was able to hook the bra himself making me feel proud and a bit embarrassed that he no longer needed their help.
The girls' joke “You're a real pro now!”
The girls picked their favorites out on Michael and then Jessica said “Let's get your matching panties and check out”
Michael was hesitant towards that but Sarah said “C’mon it's no big deal honey I’ll pay for them”
Michael agreed to her. The girls told Michael to leave his new black bra on and put on black panties on the way out. Michael agreed but still felt more comfortable with the sweat jacket on.
Going back to Sarah's he felt more confident in his bra-wearing but began to wonder “will my shirts still fit me.” He didn’t much like how his shirt fit him now with the black bra underneath.

The next day back at Sarah’s he got a call from Dr. Walker.
The Doc tells him “Your blood work came in and would like for you to come in next week.”
Michael “Ok I will be there”.
Michael reveals to Sarah how he feels about his clothes. “Sarah do you think I look stupid with this shirt and bra underneath”
Sarah “I’m glad you said something I thought you did but I didn’t want to say anything until you were ready.” “Ready for what?” he asked
“Ready for that fact you will probably need a new wardrobe of tops to support your new figure” she responded.
If you would like I think some of my camisoles and blouses will fit you”.
Michael hestiantatly “ Well I guess I knew this might happen I’ll give them a try”.

Sarah returns with a handful of clothes and hands him a yellow blouse and capris to try on. Michael puts them on looking in the mirror. He hardly recognized himself from the neck down, looked more like a woman than a guy but he did like the way his breasts looked no more back pain.
Sarah responds excitedly “ You look amazing, glad we are close to the same size!” Let’s have a fashion show and a sleepover girlfriend!” “I’ll invite Jessica and her boyfriend!”.
Michael was surprised “Ok I’m down to stay over but I don’t know about Jessica's boyfriend.”
Sarah responds with a grin “Trust me he will understand your looks I think you two will get along.”
Michael was puzzled by what that meant but didn’t say anything.

That night door rang. Sarah opened the door Jessica and what Michael first thought was another girl. Jessica said “Hi Michael this is my boyfriend Jean"
Michael quickly realized what he thought was a girl in a red dress was instead Jessica’s boyfriend Jean!
“Hi,” Jean says as the two shake hands.
Michael was amazed at the bust Jean had. Sarah noticed Michael looking at Jean’s breasts
“Don’t worry Michael his aren't t real he wears DD breast forms” He looks pretty good as a girl doesn’t he.” Michael responds “Yes he had me confused for a sec.”
Jessica overhearing them responds “Well if you like I’m sure we can make you look pretty like him.”
Michael overwhelmed “I need to use the restroom”.

Michael in the restroom couldn't believe what is happening as he looks in the mirror seeing his figure with his new bra and one of Sarah's blouses on. He thought
“What is happening all I wanted was advice on potentially wearing a bra” He begins to cry.
Sarah knocks and comes in. “Honey its ok no need to be upset I just want to help you with your body and your condition.”
Michael upset “Well I don’t want to look like Jean and be turned into a woman.”
Sarah “ Oh honey that's not what we are trying to make you do we thought you’d like to know there are men out here that wear bras and women's tops too. I know you're not a girl but if you want to be, I'll support you no matter what”.
Michael holding back tears “I guess it is nice to know I’m not the only guy”
Sarah “You have breasts bigger than mine you need to realize even though you are a guy a woman’s shirt is going to fit you much better than a men's shirt will now.”
Michael “You are right I just wasn’t ready to hear that or admit to myself. I appreciate your support.”
Sarah “Let's go back out there and enjoy the evening.”
The two got back out with Jessica and Jean. They went on to have a great time giving Jean the update on Michael’s bra fitting adventure as well as Michael trying on some more of Sarah's clothes. A fun evening and after a couple of drinks, the girls got Michael into one of Sarah’s dresses. All amazed by how well it fit.

After Jessica and Jean left, Michael and Sarah headed to bed together.
In bed, Sarah said “there is another part of breast life I haven’t told you yet”
Sarah then began to fondle Michael’s breasts, and then something unexpected happened!
Michael lactated out of his breasts onto his and Sarah's clothes.
“Oh my!” Sarah said,
“What just happened!” Michael asked.
“I think you are lactating sweetie!” Sarah responded both in disbelief.
“Good thing I’m going to the doctor soon,” Michael said.
Sarah “Well looks like you will need to wear my clothes to go to the doctor.”
“I’m sure she will be happy to see me in a bra,” Michael said.

Over the next couple of days, Michael began getting used to wearing bras and women's clothes. Sarah and Him had gone shopping multiple times and Michael had now a wardrobe of blouses, camisoles, sweaters, and more. During this time his breasts grew to a 38D which made Sarah envy his breasts. One night Sarah, Jessica, and Jean convinced Michael to give him a makeover.
Though he was once resistant to this idea now he seemed to be excited by the idea. The girls helped curl his hair and shave his legs.
Jessica said, “wow you have some amazing legs!”
Jean helped Michael in a dress he had brought for him to try on along with a new strapless bra.
Never would’ve Michael thought a week ago he would be getting help into a sexy green dress by a male crossdresser.
In the end, Sarah painted his nails and surprised him with a pair of heels. Michael could not recognize himself in the mirror and neither could the girls.
“You look like a completely different person”.
There stood a beautiful young woman not a man with breasts. They all thought the same thing Michael needed a more feminine name to go along with his feminine body. A Gwen Stefani song played in the background and Jean came up with the best idea and said “I now present you Gwen” Girls agreed on the name Michael now Gwen said,” Gwen sounds like a cute name.” They enjoyed the night together. Gwen said, “I could get used to this.”

Michael arrived at the doctor’s office wearing a matching Nude bra and panties with a brown camisole and a pair of Sarah's jeans.
Dr. Walker “Well it seems you have taken my advice on a bra and then some you look very nice in that camisole.”
Michael smiled “Thanks been an interesting couple of days”.
Dr. Walker “looks like. How is wearing a bra?”
Michael happily “I like it a lot feel helps a lot more than I thought".
The doctor asked him to take his top and bra off so she can reexamine his breasts.
Walker said “They seem to have gotten a bit bigger and fuller; your blood work came back and results were worrisome it seems you have estrogen levels of 30 old woman. This would explain your breasts, have you noticed anything else?”
Michael responded well I’ve had some... lactation some after my breasts were stimulated.”
“Oh!” Walker responded shocked and curious.
Walker then asked for Michael to squeeze his nipples and quickly some milky discharge came out.
“Very interesting. Seems we will need to get you a breast pump to help you control this.”
Michael asked, “So is there any way we can fix this?”

After a brief moment, Dr. Walker broke the news “I can prescribe you testosterone pills and estrogen blockers but it will be expensive and seems your insurance won’t cover it. Of course, it is possible if your breasts are increasing then your downstairs, maybe decreasing. Has it?”
Michael, not too disappointed by the news responded “yes it has"
The Doctor checks it out.
Michael asked excited “does this mean I’m turning into a woman?”
Dr. Walker responded “No but you are developing much more feminine features and it seems you may be past the point of return. Not sure if the meds would work now you seem to look much more like a woman then a man she said. If I had seen you on the streets I would’ve assumed you were a woman.”
Michael exticed to hear that “Well to tell you the truth Doc I think I could like being a woman.”
Doctor Walker responded “Really? Seemed last time you were much against it.”
Michael responded, “ Well I learned a lot about myself and realized I like feeling pretty and seem to have gotten used to dressing as a woman and I think I prefer it.”
Doctor Walker “Well that is great I say do what makes you happiest we can try to prescribe meds or we can leave it alone”.
Michael confidently says “I think I will leave it alone do you mind if you start calling me Gwen”
Dr. Walker responds “Sure thing Gwen and I agree you look very pretty as a woman.”
Gwen responds with a big smile “Thank you”.
Gwen leaves the doctor ready to live her new life!

The End.