Boyfriend Helps In College Assignment
By Terry Hansay
Story line — A boyfriend helps his girlfriend in a college project. She needs to get human reaction to a shock factor in life for her thesis. The boyfriend (already a closet crossdresser) helps by wearing a bra in public under a shapely feminine top and ends up loving it and wanting to wear all “the” clothes forever.

Chapter One

“Sally what are you doing for your college thesis paper”?, Mary asked. “I don’t know, I can’t figure out a thing to do for that shock factor assignment except one way out weird idea”, Sally said.

“Mary can I tell you a secret? Bill, my boyfriend is a crossdresser. He wears nightgowns to bed almost every night and wears panties all the time.”

“Well, I was thinking for your college thesis, I should have Bill dress up and I write about the public’s reaction to him wearing girls clothes. How the public reacts, how Bill feels, you know. I think this would be fun and we would get tons of human reaction to this situation”, Mary said.

“Wow, Sally do you think Bill would do it? It’s a great idea if he would do it”.

I am not sure how but I think I could get him into a bra at home, but in public where I need him, might be hard. He is shy and a real closet crossdresser. I am going to ask him tonight.

I will buy a pretty bra at Victoria Secrets today for him, plus some very cute panties. I am hoping his desire to crossdress and my help will push him into my plan. Plus his internal desire to wear lingerie will hook him with my help.”

“Sally does he know you know he wears panties? Oh, yes, I sometimes do our wash when I stay at his apartment on a weekend or so. With the wash are his panties, we have talked about how cute they are and how comfortable they are on him. He knows I accept his pantie wearing. I do like them on him, it makes him sweet”.

“Mary, I also will buy him a very sweet feminine white stretch lacey top that will show off his new bustline, in his bra. Plus I want to get him to wear a girdle with garters and nylons too. I want him to get the full affect of our soft lingerie, you know!”.

Wow, this is going to be so much fun, Mary giggled.

Sally leaned over the table to whisper in Mary’s ear, “Can you imagine when I take him into see Sue at VS to get measured. The reaction of people and Sue will be huge for my paper. I have not told Sue that Bill is a crossdresser.

Sally returned from shopping, bumping into Mary in the parking lot. “Here look what I have in this bag, his bra and panties. They are so cute, I know he will fall in love with them.”

“Wow, this bra is really padded, will he accept a big bustline? I love it; he will look so sweet in this bra. Hope he likes pink! I am getting so excited about dressing up Bill, can I come and help”, Mary said.

“I don’t think Bill can handle two women’s pushing him into wearing a bra 24/7”.

“Well, Sally you just have to call me each step of the way, I love the plan”.

Chapter Two

While driving to Bills apartment, tons of thoughts were ripping through my mind. How will I ask him and what if he says no? What if he gets so embarrassed he leaves me?

In I walked, he looked so right for this. He is a short, little guy, shy, I love him.

Bill, can we talk? Sure sweetie, what’s up? I have a problem in doing my college thesis on human reaction. Bill looked puzzled and said, “Wow, what is that all about”?

Well, I have to write about how humans responds to a situation in real life”.

“How can I help, Bills said.

“Well Bill I have and idea how you can help me. I want to write about how the public responds to you wearing a bra. What they think of a man wearing a bra”.

“What, me wear a bra, in public…are you nuts?”

“Bill, you love wearing panties plus it will only be for an hour or two. I just need to record the peoples reaction” Besides it will be fun!”

“Fun, fun for who? Boys don’t wear bras, at least in public!”

“Honey, I need this for my college thesis. You know how hard I have been looking for a topic. This would be perfect and I could write it quick. Besides I think you might like the experience. Won’t you just try wearing a bra, try it at home here, please honey?”

“Sally, you know I wear panties, are you playing with me. Is this really part of your thesis”?

“Bill, lets have some fun, loosen up, you might like this. Look what I bought you to wear”.

I watched Bills eyes open, and sparkle, he melted when he saw the VS bra and matching panties. I knew I had him hooked. He was mine when he sheepishly grabbed the bra with a big big smile.
“See Bill your new bra is very pretty and I know you like it. It’s ok, sweetie, its yours. Why don’t you try it on and wear around the house”.

Bill didn’t say another word and walked to his bedroom to change. I said he didn’t have to leave the room, I would help him adjust his the new bra, I told him. He was to embarrassed and went to his room to change.

He came out, the padding was perfect, and his bustline was perfect, very pronounced, very sweet looking. Even with his own t-shirt, it way tight, I could see his new shape and bra under it, he looked great. This was so much fun. I gave he a huge hug saying how nice he looked. “How does your bra fit Bill?”

I thought he was going to cry being so excited. “Sally are you sure you are ok with me wearing a bra around you. Are you ok with my crossdressing? Feels a little strange you doing this with me.

“Bill, I love you, I know you crossdress. I think you look great. Why don’t you leave your bra on now around the house, like a training bra, get use to your new feelings, sweetie”.

I knew he was happy. He even told me how good the bra fit and how it made him feel soft and feminine. I thought perfect, he is falling into my plan, and this will work.

We cooked dinner, watched a movie and he still had on his bra. He seemed happy about his new look.

While watching a movie he kept tucking, adjusting his bra straps. “Bill do you have a problem, do you need to adjust your straps?” “Sally, not sure this is my right size bra, seems tight.”

“Bill, I think you just need time to get use to your new underwear. Your bra is new to your body, you need to adjust. In time you will not even know you have a bra on”, Sally said.

“Sally what do you mean, “in time” I won’t know I have a bra on? I thought this little thesis was a couple of hours”? Yes, but you need to get comfortable wearing your new lingerie, Sally said.

He asked me to stay overnight, then I knew he was all mine. While we undressed upstairs there he was in his Victoria Secret pink bra and panties. He had a puppy dog look on his face so I said, “Yes, Bill you can wear your bra to bed, but you should also put on your nightgown too”.

He got all shy saying, “you know I wear nightgowns too”?

“Bill remember I help with your wash sometimes. I am ok with your crossdrssing and in fact it turns me on. Bill got all excited, slipping on his silk long nightgown over his VS bra and panties.

Once in bed, we talked. “Bill, see was that so hard, wearing your bra today. Isn’t it a pretty bra and it fits you so nice, I love it on you. Now sweetie, will you help me with my thesis”? I knew I had him, he was putty in my hand.

“Ok, Sally I will try it, but not for couple more days. I have to get use to wearing this bra at home first”.

Wow, I had him. Next I will get him into his panty girdle and nylons. This will really turn some heads and make my thesis that much better, I thought.

Next day came quick. Bill shower and he slipped on his bra and panties right away, I said nothing.

“Bill I also bought you a nice top with darts in it to help your bustline. Can you try it on?, I asked.

I held it up and I saw fear across his face. “Sally I can’t wear that, it’s too see-through, to thin, too girly.

“Bill, how will I test the public’s responds if they can’t tell you are wear a pretty bra”?

“I guess you are right, but look I have two large mountains on my chest, won’t they see that!”

“No, silly, you have to wear this, it is so sweet and I think you will like it, try it on”.

Like magic, he slipped on the feminine top. Wow, did it cling to his new shape, his bra and yes it was thin. I think I could read the label on his bra, it was very thin.

“Oh, Bill, you look perfect. This top fits you so nice, this will do the job”.

“I don’t know Sally, I don’t know if I can go out in public like this. I am man, not a sissy.

“Bill, just wear it around the house today and lets see, will you do it for me sweetie?

“Ok, but you are pushing me, but I will do it just for you Sally. You owe me!”, Bill said.

I was having so much fun, I knew I had him, he was mine. The day went great. He wore his top all day at home and seemed to enjoy his expanded crossdressing. Several times I caught him staring in the mirror looking at his new shape, how sweet I thought.

I had told his next-door neighbor and my girlfriend Melissa of the plan and to come over at 4pm to check him out. Right on time the doorbell rang; fear struck his face as I opened the door.

He was so cute as he held his hands over his chest trying to cover himself up.

“Bill you look so cute, just love the top, it’s your color!”, Melissa said.

“Bill say something, Melissa paid you a complement, its ok, she is our friend, she knows I am writing a thesis on you dressing in public. It’s ok sweetie, don’t cry!”, Sally said.

With a sheepish look Bill said to Melissa, “Sorry Melissa, I am just a little nervous wearing a bra even if it’s to help Sally and her thesis”.

“Don’t worry Bill, you look fine, lets face it we are all wearing bras in this room now, our little sorority, nothing to get nervous about.”, Melissa said as she giggled.

Sally popped right in and changed the subject inviting Melissa over for a cook out. She accepted with pleasure.

For sure the conversation centered on Sally’s thesis. Melissa even commented that she thought she was wearing the same VS padded bra and how much she liked it. “Bill did you get your bra at Victoria Secret’s ?

Bill got all embarrassed say, “Sally bought this bra for me, I could not buy a bra.”

“Bill I think you might like going in VS and getting measure for a pretty bra. It is so much fun in that girly store.”, Melissa said.

I could tell Bill was getting nervous with all the feminine girly talk. We changed the conversation and cooled the emotions down.

As Melissa was leaving, she hugged Bill saying, “I am so proud of you Bill. You look so sweet and your demeanor is so much nicer with your bra on, you should wear bra all the time. See you both tomorrow”.

I looked at Sally asking what she means by seeing us tomorrow. “Bill, I need her to help me record all the people reactions to my thesis. She is coming with us tomorrow to the mall”, Sally said.

“Sally I am not sure I am ready to go out in public, tomorrow to the mall. Can’t we do this in a couple of more days? I am nervous and don’t think I can walk into the mall yet”, Bill said.

“Well, Bill you then need to promise me you will wear your bra each day here at home until we go to the Mall to do my thesis, plus I have something else you might like to wear”, Sally said.

“Now what a dress?”, Bill said. “No silly, I want you to wear a little girdle and nylons.”

“Why, why do I have to wear that too?”

“Bill you have to get the full affect and a girdle will really help your demeanor and put you in the right mood for my thesis.”

“Sally you really know how to pull my chain. How did you know I would like that anyhow, plus no one will see nylons and a girdle under my clothes, right”?

“Right Bill, but you will know you have those feminine lingerie items on and I think you like that! You will know and it will change your demeanor, your whole thought process. Thank you dear”!

Chapter Three

So Sally waited four days, and I was wearing the girdle, nylons and bra in the house and adjusting well. It almost felt natural each morning waking up and slipping on that pretty lingerie. I was liking this and Sally knew it. I even wore my bra, girdle and nylons outside in the neighborhood, but no one saw me wearing them under my clothes, since I covered up big time, but Melissa and Sally knew I was wear those pretty foundations.

Saw Melissa me in the hall as she tapped my fanny saying, “Bill, nice wiggle back here. Guess that girdle is really helping! I love it sweetie”!

I smiled and kept walking thinking, yes I do swing more and I do like this girdle. I might wear this more often I thought. Plus wondering what it would be like to wear high heels. My mind was all over the place.

The big day came, a Saturday, busy day at the mall. Melissa came over for breakfast and the two girls got their plan down. All I had to do was walk around. They were going to watch the people and write their notes on their reaction of me, a man in a woman’s shapely feminine top and of course the padded bra.

Plus the girdle was giving me a swing, gave me a very decided feminine look and walk.

I was nervous but off we went to the mall.

Sally said I should walk alone and up front, they will be right behind. It started in the parking lot, I got stares and giggles from many teen girls all the way to the door. I was not having fun. I tried to turn around and leave but Sally and Melissa were right behind me pushing me into the mall.

Inside I had to sit down at the first bench, I was so weak and nervous. Sally and Melissa took up their positions 10-20 feet around me to observe the public and me.

People walking by just stared. I knew what they were thinking. What is a man sitting there in a bra, is he a sissy?

One lady came up to me and sat next to me but her hand on my back, on my bra strap saying, “dear are you ok, you look white faced, do you feel sick, should I call for help”? I looked up, her big smile calmed me down.

She said, “you look so sweet, don’t feel embarrassed wearing women’s clothes. My son is a crossdresser and he loves it and we have so much fun shopping here, it’s a blast, he is my daughter now and so much nicer now. Here he comes, we are shopping together today, here meet my son”.

I looked up and there was a 16-17 year old person dressed as a teen girl smiling back at me. He was dressed in a real pretty feminine dress, nylons, small heels, beauty hair and makeup for a teen, looked so sweet and demur.

“Elizabeth, meet Bill, we just met here in the mall. He is a crossdresser like you dear. Sweetie, sit with us and tell Bill how much you like shopping with your mommy”, Ann said.

This was getting weird, here was a Mom and what appears to be her daughter, but really her son wanting to talk with me about crossdressing. I looked at Sally, she waved me on smiling like this was great…. Keep talking with them.

“Bill, I hope my mom didn’t embarrass you, looks like you are just getting started with your crossdressing. My Mom is a good teacher, she helped me a lot, as you can see. Are you hear alone?”, Elizabeth said.

“No, my girlfriend, Sally is right over there. She is doing her college thesis on how humans react, how they react to me in a bra as a man”.

“Wow, that is different, but are you a crossdresser too?”, Ann asked.

“Yes, a closet crossdresser until today. I have never gone out in public. This is a real first for me and I am nervous”.

Just then Sally walked up and introduced herself to Ann. We all talk for a bit, like Sally was interviewing her for her thesis. I was feeling good sitting there with these people who “protected” me for the public. We all “connected” so well, I relaxed a lot and Sally saw this.

“Ann, if you and your son are shopping today, can we tag along”?, Sally asked.

“Sure we are going to Teen Boutique for a birthday present, please do come along”, Ann said.

Not sure I liked this, but I guess better to travel in a group than walking alone out here in my girly top and bra.

Sally introduced Melissa to Ann and son. Ann asked us to refer to her son as Elizabeth. In public he needs to get his confidence up as my daughter, she said.

Wow, this is really something. I could only dream of this adventure, a closet crossdress as I am.

Off we went all five of us to the Teen Boutique. Not sure I wanted to go into a feminine store like that, but I guess I had no choice.

Sally observered everyone looking at me as we were heading to the store. The store was at the far end of the mall, wouldn’t you know it. Elizabeth had to stop at every window and dream about buying every dress and outfit along the way. I even found myself dreaming to, what it would be like to wear those pretty dresses. Sally knew I was drooling over all these feminine apparel.

I thought it was so sweet as Ann and her “daughter” walked down the mall hand in hand. My mind was off me and the people looking at me as I watched how much fun Elizabeth was having window shopping with his Mom. I could like this, I thought.

Walked into the Teen boutique, wow, this was really a girly store. I knew of it, but never had the nerve to walk in, as much as I have always wanted to. I think I like this.

Elizabeth went right to the jewelry counter, as they said they are getting a birthday present for their nieces. They have a birthday party today at noon.

I am thinking Elizabeth is going to a birthday party dressed like this? Wow!

Sally pulled me into the nightgown section saying, “Bill, how would you like us buying matching nightgowns, wouldn’t that be sweet”?

I didn’t know what to say, other than yes. Sally pulling several off the rack asked me my opinion, in front of all these other women and teen girls shopping the store. I was embarrassed, what would they think?

“Bill don’t be embarrassed, pick a pretty nightgown and make sure you remember your experience in here, I need it for my thesis.” Sally said.

How could I ever forget this experience? I didn’t know if I was excited, happy or embarrassed in this girly store.

Sally held up a nightgown to me. I looked around to see if anyone was watching us and sure enough several teenage girls were watching us, I quickly told Sally this nightgown was perfect lets get it.

Sally picked two match nightgowns off the rack, clearly sent a signal, I was buying feminine lingerie. This was weird, but I am loving it.

Then out of know where, Sally announced, in public, I needed inserts for my bra. Now I was getting embarrassed.

A clerk heard her and came over to help. “He needs B cup inserts, do you sell them here, miss?”, Sally said. “Sure of course, step right over here we have many for you both to pick from”, the clerk said.

Elizabeth saw us at this special counter and came right up saying he got his inserts here and pointed to the boobs his Mom bought him. “They are so comfortable and feel so so real. My bounce is real and they give me my feminine shape to die for. Bill look, would you like to see them?”, Elizabeth said.

Before I could question this purchase, Sally said we would take the B cup full coverage breast inserts.

Why is she buying me these? Will she have me wearing a bra more? I got sort of excited with the idea. I was melting in her hand, and she knew it.

The clerk looked at Sally asking if he would like to wear the insert now. Elizabeth popped in saying, “Bill, yes, yes, they will give you such a feminine bounce and look, you will love them. You must wear them now, always, from now on”.

Sally smiled and said, “well I guess you have to wear them now, lets go in the dressing room and have some fun, Bill”.

Wow, they did add to my figure. My bustline seem to get bigger and yes, they did bounce so much. I commented to Sally as we walked out as she said, “Bill, you will get use to your new figure, we girls love the bounce”.

At the check out counter Sally looked at me saying, “Bill these insert will also fit well in the cups of your nightgown to, so pretty on you”!

Here I was in a teen boutique standing in front of a 26 year old clerk paying for my boobs and matching gowns as my bra is showing through this feminine top I was wearing. I guess my embarrassment should be gone, all these girls in the store know I am a man wanting to crossdress. How great is this!!

Fear struck me as the clerk said to Sally, “Would Bill like glue to give him a more secure feeling for his new breasts? Sally giggled and said of course her would, we will take two tubes.

Elizabeth came right over to be with a big smile and whispered in my ear, “Bill you will love the glue, it helps so much. My Mommy tells me and I agree with makes my breasts almost real. She even helps me with makeup around them so that they look really real, apart of my feminine body”.

I was so nervous and confused. Why did she buy two tubes of this glue? These breasts are expensive for one or two day event, I thought.

We were all done buying our feminine “items” and Ann suggested we trade phone number and get-together soon. I looked at Sally and didn’t know what to say. Sally said sure, would love to. Elizabeth seemed so happy she found a crosssdressing friend in me. But I didn’t know what to make of it, I just went along.

Ann said they had to get going to the birthday party, will call.

I told Sally I had to sit down, I was weak. Of course we sat in the boutique store right next to all the teen bra display, training bras as Sally calls them.

Melissa and Sally were concerned I was weak and wanted to know if we should go home. “No, I think I am ok, but all this is too much, need to take a break, I said.

Sally looked around at all the pretty teen bras. “Bill too bad you didn’t start with a teen training bra like these pretty little bras here as she handed me a pink padded teen bra of the rack.”

I melted and thought, yes, I did wear a little bra like this many years ago, but I was not going to tell Sally.

I keep looking down at my chest, feeling the weight of my new chest. “Bill stop looking at yourself, people are watching you”, Sally said.

I thought, of course they are watching me, here I was with a huge bustline, see through top, bounce breasts and I look like a man. But for some reason I was coming to terms with this new look, not sure why but I was less nervous about people starring at me.

Off we went, me carrying my pink flowered Teen Boutique bag with our matching nightgowns saying to everyone I shopped at the girly store.

At lunch our waitress said she loved my top. She whispered saying, her boyfriend is a crossdressser to and it turns her on. She wants to get him out of the closet and she thinks she is close since he wears a bra and girdle every day now.

Wow, there are a lot of women out here who like men who crossdress it seems. I never knew how accepting women could be of crossdressing.

Melissa made a purchase also at the boutique, I asked her what she bought there. Both Sally and her had a hug smile as Melissa said she bought the SAME nightgown we bought and was hoping she could join us for a slumber party.

What all three of us in the same pink lacey nightgown having a girly sleep over. This might be a little weird.

Lucky Sally said, “Melissa maybe some day when Bill becomes more relaxed with his crossdressing”.

Melissa did not answer her, not sure what that all was about.

Lunch was done, Sally suggested we drive into the Village and get some reactions there for her thesis. Fear came over me thinking that I might run into my friends in the Village. I told Sally of my fears. She said, “Bill, I need this interaction for my thesis. You will do fine, don’t worry about your friends. They probably already know you are a corssdresser, lets go sweetie”.

How do my friends know I might be a crossdresser???

Melissa and Sally pulled me to the car not before one girl said to her mother, “look mommy he is wear a bra, why? Isn’t he a man?

“Bill keep walking don’t look back, that was great for my paper. That little girl is so sweet, keep moving Bill”.

“Bill tell me how you felt about that little girls comment about your bra.”

“Sally I am not sure, I don’t think I was concerned, it didn’t affect me like early this morning when we left the house”, I said.

Sally gave me a big hug telling me how much fun she is having and thanked me for helping her with her paper. “Bill, my my my, what are those mountains as you call them on your chest? She snapped my bra strap as she hugged me! “Those insert are really giving your figure a real boost.”

Chapter Three

We went into the Village and stopped at a coffee shop. Sure enough there was Fred a guy I work with. Sally watched with intense care to Fred said, “Hi Bill, hope all is well” and whispered in Bill’s ear and left.

He left quickly and Sally asked me what Fred whispered to me. “Sally I am so embarrassed, he told me I look like a sissy in my bra but it looks really good on me, and to call him tonight”.

“Come on Bill, he really said that”? Yes he did, I am blown away. He wants me to call him. Do you think he is into cressdressing?

Melissa said, “Bill see there is no reason to get nervous, your friends are your friends. Maybe you found another crossdressing friend”?

Sally got so excited hearing this. She dragged me down the street looking for other people to work per thesis. Here I was walking down my village Main Street, my chest out there and I think bouncing around and my hips swing. For some reason, I was getting beginning like this and the girls saw my pleasure.

From around the corner my next-door neighbor came walking up. As she saw me, a big big smile came over her face. “Bill, so you ARE a crossdresser. I found your panties in the dryer one-day after you left the washroom. So it is true. I love your new look, keep it up dear”.

This is way to easy I though. “See Bill, this was not hard, you are doing just fine, I am so proud of you Bill.”, Sally said.

We walked to the Purse House store. Melissa grabbed us and said, lets get Bill a purse. I don’t need a purse I said, no way.

“Bill this will help my thesis, lets see how the public reacted to you having a girly purse. Remember, men do carry man purses overseas”, Sally said.

In we went, another shopping event to test me. Melissa picked up several and had me pick one. Sally watched for my reaction. Some lady popped in saying, “Oh dear that purse fits your outfit perfectly, it’s so you dear”.

I thought my outfit? What outfit, do I have an outfit on? I got all shy and smiled as Melissa pooped in saying, “Yes, this is the one Bill, it’s so you Bill, perfect and I want to buy it for you.”.

That same lady approached Melissa and whispered in her ear, as Melissa said, “yes, they are real breasts, aren’t they sweet”.

I pulled Melissa aside and asked what that was all about, what is sweet?

“Bill, that lady wanted to know if your boobs were real”. “Melissa, you told her they were, why?”

“Bill don’t worry, she is a buzzy body and look at her starring at you now, she has nothing better to do. So what, be proud of your figure!”

I had enough and said I needed to go home. The girls got the message and we left the Village. But not before we saw Fred again across the street. He looked at me and yelled “Bill call me tonight”! I waived with a smile thinking what does he want?

I asked, “what is that all about?” Sally said, “Well maybe he wants to crossdress with you. Would that make a college thesis, how two cross-dressed meet!”?

Back at my apartment, I tried to go upstairs to change, but Sally said no, time to fix dinner. My job was fixing dinner, never done that before, but never wore a bra in public before either, I thought. Sally wrote her notes on the computer. I would love to read what she is writing.

“Bill, that lady and her son in the mall, how sweet she came to your aid when she thought you were crying on the bench in the mall. I hope we can hook up with them again so I could add a twist to my paper. Her son was so cute; he passed as a teen girl so well. He was so sweet and seems to really like you.”, Sally said.

“Bill, have you ever dressed all the way? Tried to pass as a girl? Baby you can tell me, its ok, I love you either way and after today, I really love your feminine side so much, you are so sweet when you have feminine emotions running through your head”, Sally asked.

“Sally only once and never did it again. As you can tell I like soft clothes, but today was very different, emotionally and I really need to change the subject and get to bed now, I am beat”.

I made a metal note, he did try dressing before. I think my plan might work, Sally thought.

Next morning came fast. I really seem to sleep well in these soft lacey nightgowns. Plus getting use to these glued on boobs sticking out while sleeping was hard. Sally told me I would adjust.

Sally was already downstairs fixing breakfast as I walked into my kitchen.

All of sudden, Sally got all nervous with me. “Bill what are you NOT wearing? Where is your bra sweetie? Those aren’t your clothes now, you need to get dressed!”

“Sally what do you mean these are my clothes”!

“Bill did you forget we still have to go to Victoria Secrets today to finish my paper with Sue. You told me you would go there, Sue would help us. You have to stay in the girly “mode”, you need to wear your pretty clothes, I told you that. Now you go back upstairs and put on your pretty lingerie, your lavender padded bra and matching panties and get rid of those ugly sweats. I put out on the chair a loungewear outfit that will match your pretty underwear. Now go sweetie, please. You need to keep your promise and remain dressed for the part.”!

She was right, I forgot, I said we would stop by VS to see our friend Sue. I went back upstairs to slip on my padded bra. It felt so nice, as I kept looking at myself in the full-length mirror.

“See silly, you love those soft clothes Bill, and you know it sweetie!! Now lets have breakfast and go shopping for my sweetie”.

After my shower, Sally had my outfit on the bed, wow, another see-through top especially with the bra she had out, the same lavender padded bra. I was nervous as I held the top up and Sally popped into the bedroom saying, “Isn’t that top so pretty, so lovely, you will look great in it, so soft and shapely, for you.”

She seemed so excited helping me hook my bra and adjusting the cups with the inserts. “Bill you wear your bras so well, it’s like you have had your breast supported wearing a bra all your life. I am amazed how well you fill out your cups, so nice. This top will look so sweet on you and will cause so much attention for my thesis”.

I was feeling good and melting as I saw myself in the mirror. The top was nice. Scoop neck with a small lacy collar, short puffy shelves and very fitted around my what seemed to be huge bustline.

“Sally, do I have to wear a padded bra with the inserts too? I seem very big up here.” As I held my bustline!

“Silly Bill, you look great, just right for your new look. Plus remember, we want to get the public’s reaction to you wearing a pretty bra, you know for my thesis. Please Bill I know what is best and you said you would help me do my paper”.

I heard her say “new look”, but it did not bother me. I was getting use to this look and I think liking it. Wow, what is happening to my brain?

Off we went, not before Sally remained me to go back in the apartment to get my purse, plus Melissa showed up to come with us too. I put up a stink about caring a purse. “Bill get your purse, you need it to finish your new look, plus your purse will match your pretty top you are wearing today. You know us girls have to be coordinated!”.

Did she say “us girls”? I did what my “girls” said, but my mind was going in to many directions.

Walking to the car, Melissa whispered to me saying, “Bill, love your lavender bra, don’t you? Such pretty lacey on the cups and back straps.”

I looked at her smiling thinking she can actual see the color of my bra and that there is lace all over it. Wow, this is really too much.

In the car Sally pulled out of her purse more pills telling me to take them saying it will help me relax. I have taken them the past 3-4 days and she is right, I do like them. Makes me calm, so relaxed.

As we were walking again through the mall, people were looking and smiling as we walked by. For some reason I was getting use to the comments and they did not affect me as much. Every other window Melissa would say, “Bill, isn’t that dress or top pretty, wouldn’t I like that dress or even those sexy high heels”.

I found myself dreaming about that… how would I look in that dress or outfit. I found myself asking the question more and more. I wanted to try on high heels in the worse way. What is happening to me?

Sally saw me looking intensely in each window. She smiled and said in many windows, “Bill would you like that dress or those heels?”

I just blushed and smiled and said, “I don’t think they will fit me”. Sally laughed and said, “yes I am sure we could find your size” sweetie.

Both Melissa and Sally looked happy as they pulled me into VS. There was Sue our friend waiting for us, like she knew the minute we were coming in.

I got nervous in this feminine store, plus lots of teen girls and women now looking at me.

“Hi Bill, my my my don’t you look cute in your lavender top, so striking on you Bill”, Sue said.

Sally popped in saying, “See Bill I told you, you would look good in that top, fits you perfectly”.

Sue whispered in my ear, “Bill you are so sweet helping Sally with her thesis, you are such a good guy! Now lets have some fun, raise your arms so I can measure you for a real bra. We do want everyone here to see us, you know for Sally’s paper….”!

Like magic or second nature, I raise my arms and Sue got the tape measure around me so fast. I looked around and yes, the teen girls were giggling at me. I just smiled back, as Sue announced I was a 34 B and she had just the pretty bra for me. For some reason, maybe those pills, I was ok with all this now. I even had thoughts going through my head at how pretty all the lingerie was in here. I love the Pretty in Pink slogan the store has. Wow, what is going though my head.

Sue pulled me into the dressing room and we tried on many bras. She was with me, it was strange but Sally said it was ok.

“Sue I want Bill to wear one of your bras home today, so make sure he finds a pretty one and he leaves it on”, Sally said.

Sue looked at me and said, “Bill you heard Sally, I think I have just the bra for you sweetie, to wear home.”

I could believe the bra she had me in and said this is the bra to wear. It was padded, but now very shapely, almost pointed cups.

Bill I have you in our best selling pushing bra, the boys love it, plus I thought a C cup would look better on your shape.

As I started to question the large cup size as she put her finger to my mouth and said, “Quite Bill, this is the bra for you honey. See how nice it is on, we girls just love the pretty shape of our bustline and it drives the men crazy”.

I was shocked how well I filled out the bra. It was padded in a strange way, so shaped, a hard cup somewhat pointed cups. My inserts just filled the cups like they were perfect for this C cup bra.

She put my top on and wow, this bra was way different. I was very shapely and out there. She handed me two other bras and my old bra I wore into the shop and said lets get you the matching panties for your new bras now.”

As we walked out of the dressing room, it seemed everyone in the store was waiting to see me. Both Sally and Melissa were out there with the hands over the face with such excitement at my new look. Plus everyone was smiling as I walked out. Sally hugged me with such approval saying how nice I look. “Sue did a great job finding the right bra, just love it Bill”, Sally said.

We got the matching panties and another lounge outfit, all in pink, of course.

We checked out as Sue hugged me saying how good I looked and told me to stop in any time, I will need more bras she said.

Why will I need more bras, I thought?

Sally had me carry the big pink VS bags as we walk out though the mall. If my big bra, big bustline, see thought top didn’t announce my girly look, the VS pink bag did.

This C cup bra was way different and really projected my bustline. Sally saw my concern as I kept looking down at my chest. “Bill you look fine, I love your new bra”!, Sally said.

I asked to go home, but Sally said no, she need more time in public to get more reactions. “lets go window shopping Bill, you seem to like that sweetie”, Sally said.

Off we went. Sally taking notes of the people starring at me. I was getting use to people looking and pointing at me. Even Melissa said, “Bill I think you are liking this girly shopping experiences”.

At lunch I whispered to the girls saying, “This bra is very tight and not sure of my larger cup size”.

Sally asked, “what do you mean larger chest? Did Sue measure you and give you a bigger cup size?’

I knew Sally was playing with me, she knows I am wearing a C cup bra now. I just smiled and said, “Sally come on you knew she put me a bigger cup bra”.

Both girls giggled and admitted they knew saying they told Sue to put me in a C cup bra to see my reaction and to have some fun.

Ha, Ha Ha, I said, I feel different with a bigger bustline and this push up bras feels funny.

“Oh, Bill you will get use to it, dear, its fun, fun to get all these stares as we walk, isn’t it dear?, Sally asked.

After lunch Sally said we needed to stop into JC Penny’s for one more “thing”. Now what?

We went right to the lingerie department as she pulled a large girdle of the rack. “What is that for? I already have one on!”

She dragged me into dressing room as the sales clerk looked puzzled.

She had me put on this tight girdle with garters.

“Well, Bill what do you think? Have you ever worn this kind before dear? she asked.

I was shy and admitted I had. “Good because I think you should wear this kind of girdle a lot more, you know for my paper”, Sally said.

“Sally how is this a different girdle than the one at home you had me in all week”? “Bill, you will see, they are different”, Sally said.

I asked how this will help with her paper, she smiled and said, please Bill just help me here, do as I say”.

I use to wear a girdle all the time many years ago. I love it under my man clothes. So, it was nice to wear one again, especially with my girlfriend’s approval. I smiled and said ok, lets get it. Sally smiled so big and said we need to get you some pretty nylons now too.

As I tried to tug the girdle off, Sally stopped me saying, “Bill leave it on, you look so good in it”.

As we walked out of the dressing room Sally gave Melissa two thumbs up, like it was signal he bought it. Melissa already had “my” nylons in hand, several pair as she said, “Bill you are going to love these, they are so soft and will shape your legs so nice”.

By the time I was so out of it, they could have put me in a dress.

Leaving the mall I had a really really different walk, with the new girdle on. Both Sally and Melissa commented on my walk. They giggled asking how I liked all my new underwear?

Back at home Sally start asking thousands of questions for her paper she said. Like how did I reaction to the women and their giggles at me while wear a see though top, walking with a purse and just girly shopping.

I told Sally was happy to help her with her paper. It was a real experience and showed me a different side of your women’s life.

Just then the phone rang, it was Ann. The mother of the crossdressing son, Elizabeth. I thought this “fun” might be over until Sally accepted a “shopping” trip with Ann and her son tomorrow.

I looked at Sally saying no, I can’t do more shopping. “Bill, please just one more day. You like Ann and her son. Plus this interaction would add to my paper so much, please!’

How could I say now to Sally, plus those pills are really relaxing me.

After dinner, Sally commented on how nice I looked in my new VS bra. She commented that I should not be tugging on my bra straps so much, I need to get over that, ladies don’t do that, she said.

I told her this bigger bra was different and I was not getting use to the new feeling as I looked down at my bigger bustline.

Next morning Sally had another new top for me to wear and laid out the new VS 34C push up bra. Today I got dressed in the bra and top without a second thought. Plus I got excited slipping on my girdle and nylon’s. I thought to myself, this is strange, I am liking this a lot. Like old times for me, wearing a girdle and nylons.

At breakfast Sally told me how nice I looked and how much fun we will have today again.

She saw my pleasure in my face, I was getting way to use to my new girlish look.

“Bill, could I ask you today to wear a touch of makeup, just a little, sweetie?!”

I am not sure why, but I said ok and Sally grabbed my and pulling me upstairs to her makeup table. I thought to myself, why am I so excited about her putting makeup on me?

I watch as she applied eyeliner, color to my skin and lip gloss. Clearly one would know I have makeup on, but I was ok with it.

She gave me a big kiss and hug and said, “Bill you look great, I am so proud of you, you are so sweet, lets go have more fun”!

Off we went back to the mall to meet Ann and her son Elizabeth. Yes, Melissa came to, she was always with us it seems now.

Walking into the mall Melissa snapped my bra straps saying, “Bill you look so cute with makeup on, I just love your new look”!!

I said, “my new look?”

Melissa quickly said, you know your pretty top and nylons.

I had pants on how did she know I had nylon’s on?? I thought she was talking about my new makeup.

In the mall there was Ann and her son. Wow, he was all decked out in a very feminine flowing dressing and such a pretty hair do and full makeup. You would never know he was a boy. Even his training bra showed saying to one and all, here I am a pretty looking teen girl and loving it!

Like a bunch of girls, we all gave hugs. I was liking this girly thing, loved the hug. Plus Ann whispered in my ear, Bill, you look so sweet, love the makeup today”.

I thanked her as Sally was watching our interaction. We all giggled saying, “Lets go shopping”. Off we all went. I saw how Elizabeth walked, swinging her little teen purse and her shape was so feminine. He was really getting into his new feminine life.

I even caught myself asking me if I could ever look as good as him?

Ann announces she and her son needed to go to VS. Oh, boy here we go again, in that girly store.

Sure enough there was Sue in the store, all smiles seeing me. “Bill love the makeup dear, brings out your features, your eyes, so sweet! Love your new shape Bill, do you need another bra?” she said.

Seems like everyone in the store heard her talking to me. Made me shy but this time not nervous. Was I liking this?... all this girly stuff?

I watch Elizabeth, she or he was so excited about all the pretty lingerie his mom was buying him. Wow, he really is a girl, I thought.

Sue pulled me aside and asked me, “Bill I see you are wearing the push up bra I sold you. I guess you really like the new shape I gave you? I just love your look Bill! Would you like to buy another bra and panty like that you are wearing? Don’t be shy Bill, I will help you.”

I smiled and said, “I would like to buy this same bra, but in pink”. Sue got all excited as did Sally and grabbed a bra and pantie set off the rack saying to me, “Bill this will look so cute on you!

As we all left the store, Elizabeth looked at me saying, “Wasn’t that a fun store, I just love all the pretty lingerie they have. I could shop in there all day”.

Wow, this boy is really hooked. I thought my crossdressing days were full but this kid is really living the feminine life.

We all walked through mall, again Elizabeth and I carrying our big VS pink bags, signs saying we were shopping at the all girly store. But for some reason, I was happy, as I was walking, not afraid of showing my pretty “bags” or figure.

Melissa whispered to me, “Bill I love your new wiggle”. I thought to myself yeh, me to. I am liking all this all too much as I “wiggled” my body even more.

Both Sally and Melissa were so happy and we were all having so much fun. Ann and her son had so much fun to shopping to. Her son was such a sissy, a real girl for all appearances.

I was secretly envious of him passing so well as a teen girl. How nice must it be to pass as a teen girl? He and his Mom were having so much fun.

It was strange when we all strolled into a dress store. Sally knew I was excited. Elizabeth was gushing with excitement, as he wanted every dress in the store. His mother had to slow him down.

“Bill, wouldn’t this dress look good on me, even on you to Bill. We could be twins wearing this pretty dress”, Elizabeth said to me.

I think that was Sally cue, she pulled me aside saying, “Bill would you like to try on a dress, sweetie. I think you would like to, wouldn’t you dear? Don’t be afraid to let your feminine feelings show, it’s ok dear, I love you”. As she gave me a big kiss and hug, reassuring me it’s ok to express my feminine feelings inside me.

I melted and said yes. Not sure where that yes came from, but Sally was so excited. Before I knew it she had a dress for me to try on, like she knew I wanted to wear a dress in the worst way.

I got a little giggly as we walked into the huge feminine dressing room. Elizabeth tried to come with me as his Mom pulled him back. Sally came in to help me. Here I was slipping on a very beautiful dress, I looked up seeing my nylon’s, girdle and pushup bra in the mirror as the dress slid down over my shapely body. I think I was in heaven and my face showed it.

“Wow what do you think Bill? You love divine, so sweet”, Sally asked.

I hesitated with excitement, Sally popped right in saying the dress was perfect, just my color and it fit so well. Saying I might need a different girdle to shape my waist better, plus a strapless bra, but she loved it.

What do you think Bill, do you just love it? Say something….

I started crying with pleasure. Sally hugged me kissing me saying, I guess my girl loves her new dress!

I hear heard say “my girl”, My dress” but I didn’t care. I was melting and loving this new experience. I was so happy and Sally knew it.

“Bill you have to have this dress, its perfect on you sweetie. Lets show the girls your new dress, they will be so proud of you”.

I am not sure why, but I walk out of the dressing room and spun around modeling “my” new dress to Melissa, Ann and her son. I was in another world, on such a high I could not believe it.

They all giggled with excitement and saying that dress is you and I have to buy it!

Back in the dressing room I kept staring in the big mirror. I just loved this shapely dress and didn’t want to take it off.

“Bill I think you want to wear your pretty dress home, don’t you love?”, Sally said.

I said, yes, oh yes. Sally can I wear it now, I just love it. Do you think it’s too short?

“Silly boy you look great, the dress is you but, you have to get heels and a strapless bra for this dress. Maybe a strapless corset to shape you in other ways. We need to do more shopping for your new outfit, slow down Bill, time will come to wear your pretty dress out in public for all to see.”, Sally said.

As I kept staring at myself in the mirror, Sally whispered in my ear so sweetly, “Bill, honey do you think you would like to take the big big jump and get a pretty wig and really dress for the new life you are dreaming”?

I knew what she was saying, becoming a woman for all to see, 100% passable like Elizabeth. I was melting, so confused, wanting to experience that but not sure I could pull it off.

I looked at Sally saying, “I would really like to try with your help honey”!

Sally hugged me saying, “lets make you beautiful Bill, you will love your new life”!

I think that was my turning point. I just loved the dress, love my new friends, love shopping, my life was so exciting; I was on top of the world. Both Melissa and Sally were excited for me to. I really like having these girlfriends, so much fun!

We bought the dress plus a couple more with such excitement. We all went back to our apartment to celebrate, we were having such a girl’s party until I called my messaging center.

My boss called to say my job was terminated because our building burned last night. I had no job. Plus I just had my car reposed.

I told Sally with tears in my eyes, “What am I going to do, I have nothing!”.

Sally looked at Melissa and said maybe now is the time …. “Bill would you like to move in with Melissa and me but there is only one requirement. I live in a women’s only apartment complex, as you know, you would have to dress as a woman all the time and become very womanly to be accept in my apartment complex. Plus Melissa is moving in with me too.”.

Sounds like a huge sorority house. How could this crossdresser say no?

With a big big smile, I looked down at myself in my new pretty dress, a shapely figure, a bustline many girls would kill for, thinking I could handle this, live with them as a woman. Plus live in a complex with all women, wow! I knew Sally would support me, after all she wants me to wear a wig now.

I hugged both Melissa and Sally saying yes, I would love to live with them, but I have no job, no money.

Both girls looked at me saying, “don’t worry dear, we have a full-time job for you sweetie and I think you will love it. Plus you can wear your pretty dresses, makeup and high heels every minute of the day with us”.

The end.