Jessie looked at the bra he was given to try out. He liked the color for sure. I mean who doesn't like light pink? He also liked the intricate detail on it...the tiny lace stitching, the flowers sewn into the center, the delicate straps.
He took off his top, then unloosed his bra, leaving his breasts dangling.
"Whoah! You have been eating your Wheaties, haven't you?" Ashley joked as she sat there open-jawed. On Jessie's chest hung two well formed breasts swaying gently as he moved. He must have grown a full cup size since she had seen them last!
Jessie quickly put the bra back on, feeling embarrassed.
As the two sat at the food court eating lunch, Ashley couldn't help but how much her friend had changed. He now sat there with his nylon covered legs crossed in a very feminine manner and spoke with an unmistakable high girlish tone. Wow, how could he not know what was happening to him?
"How does your bra feel Jess?" Ashley asked out of the blue.
"It feels good. My chest doesn't jiggle all around like it was before. I think that the bra may actually help my swelling go away by providing some stability and protection to my chest."
"Good to hear. You know something? There's a really great bra store in here that I want to go to, because I need some new ones. I think you should get fitted also and maybe I'll buy you one if you're lucky."
"Nah, it's Ok. I'm only wearing this cause of my swollen chest. I'm no sissy who goes shopping for bras. I will be waiting outside when you go bra shopping."
"Now now Jessie, the girls who work there are professionals and they can find the perfect fit for you. To be honest with you, it's pointless to wear a bra unless it fits you properly. Don't you want to be in the right fit? It can only be good for you sweetie," Ashley replied. This was just getting too easy, she thought.
"Yeah, I do want the right fit, but you don't think they will look at me weird? I mean how many boys get fitted for bras? It's going to be embarrassing."
"Nah, those girls are professionals. I bet they won't even give you an odd look. In fact, if they do anything that makes you feel embarrassed, then I will buy you lunch for a week. How does that sound?" Ashley knew the girls at the store would not say anything, because Jessie looked very much the girl.
"Free lunch for a week? Dang, I wouldn't mind getting embarrassed for that! You're on!"
"I'll be right back," Jason said as he got up from his chair and headed for the restrooms.
Ashley froze when she saw where he was headed. What could she do? Oh crap! What if he caught on when he was kicked out of the Men's room? She couldn't think fast enough and settled on waiting it out to see what the outcome was. Maybe there would be no-one in the Men's room.
Jessie entered the Men's room without second thought and headed over to the stalls. Dang, both stalls were full. He glanced over at the stand up urinals. "How the heck do guys use those?" he thought. The thought never crossed his mind that he could actually stand up if he wanted. He started to squirm a bit as he waited for a stall to free up. He felt like he was going to pee his pants and pondered the idea of pulling down his pants and somehow squatting to pee into the standing urinal, but realized how embarrassing it would be if someone walked in and saw him.
Finally he heard a flush from one of the stalls and seconds later a teenage boy came out.
"Whoah! What are you doing in here?" the boy questioned Jessie.
"What does it look like? I've got to go to the bathroom!" Jessie replied to the stupid question.
"Is yours closed or full? I mean, I could stand watch if you want me to. I'll keep anyone else out until you leave," the boy offered the pretty girl, figuring that she had to go so much that she deciding she had to use the Men's room.
"Whatever, I don't care. I've really got to pee though, so do what you want," Jessie replied as he closed the stall door, pulled down his shorts, pantyhose and panties and sat down on the toilet. As he finished he tore a pat of toilet paper off and wiped, then pulled everything back up.
As he exited the stall he noticed the boy was still there with an odd look on his face. He looked almost embarrassed and quite nervous. Jessie couldn't help but notice a bulge which had formed in the boy's pants. This dude had a hard on! What kind of freak gets a hard on in the Men's room? Jessie wasn't interested in finding out and quickly left the bathroom.
"Was everything Ok in there?" Ashley asked in a concerned tone.
"Sure, I just had to wait for a while, until a stall opened up. There was also this strange guy in there that seemed a bit obsessed with the Men's room, but to each his own I guess."
"Ok, well let's go bra shopping then!" Ashley replied as she grabbed his hand and led him to Victoria Secrets store.
"Hello girls, can I help you with anything?" a salesgirl asked.
Jessie wondered who she was talking to at first, but saw that she was talking to them. Then he noticed that there was another woman shopping behind them. The salesgirl must have thought that other woman was with them and that's why she said "girls".
"Oh she's not with us. It's just us two," Jessie responded.
"Okay..." the salesgirl replied in a quizzical manner. "What can I help you two with today then?"
"Well my friend and I would like to get fitted for bras. I am in desperate need of new ones and Jessie here would like to see what you have."
"Okay. Well you are a 34c and let's measure you now, Jessie."
The salesgirl had Jessie lift his arms as she placed the tape measure under, across and over his chest. He admired her beauty and how feminine she carried herself.
"I love your hair," Jessie said.
"Oh thank you. I just had it styled this way. I'm showing that you are a 34b cup. What size do you have on now?"
"I don't know. I just started wearing a bra yesterday," Jessie replied.
"Wow, that's not good. You should get in the habit of wearing a bra every day. If not, you will have back problems and you won't have the support you need."
"I know. I need to wear one until the swelling goes down so Ashley said you would have a bra that would be the best for me."
The salesgirl was a little perplexed by his statement, but let it go.
"Well you try this one on Jessie and your friend should try on this one. Let me show you to our dressing room."
The two entered the dressing room area and Jessie headed into one of the dressing stalls. As he closed the door, Ashley quickly entered and closed the door.
"What are you doing in here? You can't be in here!" Jessie stated, feeling embarrassed that his new friend had barged in.
"Why not? I'm gonna try my bra on too. You're a guy so why get all stressed out about taking your shirt off in front of me? I'll show you mine if you show me yours," Ashley said in a flirty tone.
She then took off her shirt and undid her bra. Jessie stared in disbelief as he saw his bare chested friend. "Wow! She was very well
endowed," he thought.
"Those are beautiful," Jessie said as he admired her boobs. He did find it a little weird that he wasn't really turned on though. There was no denying that she was beautiful, but he was witnessing a beautiful woman more than getting a hard on.
She slipped on her bra and modeled it for him.
"What do ya think? It feels really great!" Ashley said.
"It looks beautiful on you. I really like it," Jessie replied.
"Ok your turn now. Take it off baby."
Jessie looked at the bra he was given to try out. He liked the color for sure. I mean who doesn't like light pink? He also liked the intricate detail on it...the tiny lace stitching, the flowers sewn into the center, the delicate straps.
He took off his top, then unloosed his bra, leaving his breasts dangling.
"Whoah! You have been eating your Wheaties, haven't you?" Ashley joked as she sat there open-jawed. On Jessie's chest hung two well formed breasts swaying gently as he moved. He must have grown a full cup size since she had seen them last!
Jessie quickly put the bra back on, feeling embarrassed.
"Don't forget to get those babies centered in the cups," Ashley reminded him. "How does it feel?"
"Really great actually. Nothing against my mom, but I think she bought me some cheap bras, haha."
"Well you really look fantastic in it Jessie! Shall we buy you a couple?"
"Yeah, I think I'd like that. You were right about the salesgirls here too. They are very professional. You're going to buy me some bras?"
"Sure thing. I'm in a giving mood today...call me miss generous!"
The two got dressed again and headed out.
"How did the bras fit?"
"Perfect. I am going to get three and my friend here and going to get two."
"Wonderful! Keep in mind that we also have a buy 1 pair get 1 pair free sale on all of our panties. Let me know when you are ready then."
"So, does your generosity extend to panty sales also, Miss Generosity?" Jessie joked.
"Huh? You want to look at panties?" Ashley asked, not knowing that to think. She knew he was wearing panties, but also knew that he had no idea that he actually was.
"Duh, yeah. I mean I like the ones I'm wearing, but there are so many different kinds here. Oh, I'm sorry...you were being very nice by offering to buy me some bras and then I expect to go panty shopping on top of that...no wonder you're upset. I'm sorry. We can stick with the bras only," Jessie said as he realized how selfish he had just become. "I'm such a typical guy sometimes," he thought.
Ashley figured out that Jessie's mind must have just switched over to where he no longer found anything wrong with wearing panties. He knew he was in panties and saw nothing odd about it...Wow!
"No sweetie, it just surprised me that you were interested in the panties is all. Let me explain the different types..."
