Anything For a Date

by Jennifer White

  

The office was mostly a dreary place for Matt, for the first five years of his career that is. He came in on time every morning, worked hard, stayed later than most, then he went home to rest up for the next day. It was a job and nothing more to him, although he of course loved the good income he made. Since he was such a hard worker, he kept slowly and steadily rising through the corporate ranks.

The office was a dull gray place for him. But all that changed when they hired Jessica.

 

From the first time he laid eyes on her, she was the shining star of his life. He lived and died to spend even a few precious moments together with her. She was perfect, as far as he was concerned. Of course, there were many other guys in the office that were after her, but he seemed to be doing as well as most. He noticed that the ones that came on really strong were rejected outright. In fact, nobody had been able to get her to go out on a date yet. She wasn't married, so they kept trying. Matt decided to try for a more subtle approach.

Instead of asking her out, he mentioned that he was having a party at his house on Saturday, and asked if she'd like to drop by. There would be a bunch of people that she knew from work there, and since she was new in town, she might like a chance to see some people in a social setting instead of at work.

She didn't commit one way or the other, so he was hopeful, but nervous. As the days passed by, he looked for some small sign from her, but he didn't have a clue if she would come or not.

 

When the party started, his eyes were always on the door. He couldn't wait to see if she would show up or not. By 6:30, he felt certain that she wasn't coming, and he felt *so* disappointed. But then, there was a knock. *She* had arrived! Matt was elated, overjoyed at this good fortune. *She* was at his house!

"Come in" he said, holding the door open for her.

"Thanks Matt. I'd like you to meet my friend Jenny. I hope you don't mind that I brought her along too?"

"Not a problem. Let me get your coats" he said, welcoming them in.

Matt tried to talk to her all he could, and gave them a tour of the house. He didn't want to seem like he was coming on too strong, so he went to talk to other guests, but he gave Jessica as much attention as he thought he could get away with. He was saddened to see her go when the other guests started to drift away, and only then did he begin to drink. He had wanted to impress her, and didn't want alcohol to get in the way. He had needed his head straight. But now he could relax.

* * *

 

Over the next few weeks, Jessica seemed a little more open to conversations, and he spent more time with her. They had lunch together a few times, or he joined her group of new friends from work for a coffee break once. He decided to try for something more now.

When they finally had a moment alone, he got down to business.

"Jessica, I remember how you said you liked classical music. I happen to have two tickets to see the symphony on Saturday, but my friend Brad can't make it. Would you like to join me? I'd hate to have it go to waste, and so few people like classical music these days."

"Why that is very sweet of you Matt. Sure, I'll go. They're playing Beethoven's Ninth, and I was thinking of going myself."

"Great, its settled then. Do you want me to pick you up? Or would you rather meet at Orchestra Hall?"

"Parking is so bad downtown. Why don't you pick me up?" she said.

Matt smiled. It was going perfectly. Of course, Brad had never planned on coming along. It was just his excuse to be able to ask her out, but without asking for a date.

* * *

 

On Saturday, Matt drove to Jessica's condo and knocked on the door. He had considered bringing her flowers, but this wasn't a 'date' and he didn't want to rush things. So he just met her, and drove her downtown.

The concert was wonderful, and they both enjoyed it immensely. Instead of fighting the traffic, Matt suggested that they go to the coffee house down the street. Jessica accepted the offer, and soon they were sipping cappuccinos and talking some more.

Matt was just floating. Here he was with the girl of his dreams. The more he spent time with her, the more he was sure he loved her. His heart pounded. He wanted her so much! He had to make sure he did the right things to keep going in the right direction.

So when he took her home, he didn't ask to go in. He just saw her to the door, and said goodnight.

* * *

 

Matt called her on the phone a few evenings a week from then on. Sometimes, she would call him. He decided that the time was right now, he would make his move. He asked her on a Friday to come over for dinner, to try out the new grill he had just bought. He was going to make grilled swordfish and portabelo mushrooms. She accepted his offer, so he got everything ready.

When Jessica showed up at the door, Matt's house was clean an spotless. He had classical music playing on the stereo. Candles burning on the table. A bottle of white wine on ice, with two glasses at the ready. He poured the wine, and they talked as he grilled dinner.

After they ate, he had ice cream and fresh blueberries for dessert. Then they sat on the couch, finishing off the last of the wine.

"Jessica, I wanted to tell you something" he said.

"Sure Matt, what is it?"

"Well, this is hard for me to say..." he started, using his well rehearsed 'shy guy' routine. "..but since we've been spending more time together lately, I've really enjoyed it."

"Me too" she said.

"I've found myself thinking of you more and more. I really think I feel something for you inside. I guess what I'm trying to say is....I'd like to start dating you."

 

Jessica was silent for a moment. This wasn't good. Matt expected her to reply in kind. But instead, she laid a bombshell on him.

"Matt, this is a delicate subject for me. I consider you a good friend, so I will tell you something that nobody else at the office knows. Do you promise not to tell?"

"Of course, I'd never betray a confidence to a friend" he said.

"You see, ever since I was a little girl, I've never been interested in boys. I remember growing up that I was more of a 'tomboy' than a girly girl. Oh I'd wear a dress for special occasions and things, but I was more at home playing baseball and football with the boys."

"I was more of a boy than a girl in that way. I hung out with the boys, and did what they did. But when I got a little older, that changed. I remember one day we were playing football, and suddenly, nobody wanted to tackle me. I asked them whey not, and they said it was because they didn't want to hurt a girl. That was when they stopped looking at me the same way. Their hormones kicked in, and I was no longer a playmate, I was 'a girl'. I hated it."

"Then my body was changing too. I hated when my boobs started to grow. Now they're big, but back then I used to wrap a cloth around myself to try to hide them. I didn't want to turn into a woman! I tried to fight it, but it was no use. And when I had to dress up in frilly things, I hated it too. I hated being feminzed like that. I hated having to wear a bra. It was terrible, and I hated my body."

"I remember as a senior in high school. I was on the swim team. After class, we would change into our swimsuits in the locker room. I remember one day looking at Wendy, who was undressing across from me, and just staring at her. It excited me to see her naked! After we showered, as she put on her bra and her skirt, I was getting wet from watching her. I was sorry we never got together. I had a crush on her, and I was falling in love."

Matt was too stunned to say anything in reply.

"When I was in college, almost by accident I had an experience with another girl. We were in the laundry room together, and bumped into each other. As we brushed each other's bodies, something happened. She put her hand on my cheek. I put my arm around her. We kissed. It was heaven! I knew then why I had never fallen in love with a guy. I was a lesbian. I only wanted girls."

"Tammy and me were together for two years, and since I graduated, I've had a few girlfriends. You met Jenny at your party. She broke up with me, so that's why I've had more free time lately. I've spent it with you, and you are a wonderful friend, but you just wouldn't work out as a date. You're not a girl. I'm sorry if I hurt your feelings, but I want you to understand how *I* really feel inside."

 

Matt cleared his throat, and finally spoke. He wasn't going to give up! He couldn't. This was his dream girl, and nothing would stop him.

"Jessica, what a touching story. I would never have guessed that about you. I'm so glad you trust me enough to share something like that with me. But you see, I also want to share something with you. I am in love with you, with all my heart. I dream of you every night. Please, give me a chance. Maybe things will be different this time. Maybe you can find it in your heart to love a man."

Jessica shook her head.

"No Matt, it can't be. Look at it this way: how would *you* like going on a date with a guy?"

"I'd hate it!" he said. He wasn't a....

"Or what about kissing a guy? How would that make you feel?"

"Gross! I wouldn't do that!"

"How about having a guy stick his manhood into you? Or you sucking it?"

"Never!" he said, mad now. What the hell was she talking about?

"You see, that's how I feel too. Try to feel some empathy here. When you ask me to go on a date with you, imagine how you'd feel if Robert from the office asked you out."

"You really feel that way?" said Matt sadly. His dream was dying. His heart was breaking.

"Yes, I do. I'm sorry. You're a nice person, and if you were a girl, things might be different. But you're not, so it just won't ever work for me. I'm so sorry. I think that I had better go now."

She left as he just stared at her, crushed.

 

For the first time since he was a child, Matt cried. He cried himself to sleep that night too.

* * *

 

Jessica felt bad about the whole thing. She had tried her best not to lead him on, or give him ideas. Perhaps she had let him get too close. Maybe she shouldn't have accepted any of his invitations. She felt so bad about it. She could tell he was heartbroken, and she wished she could have broken it to him nicer. But it was the truth. It was his own fault for thinking something was possible when in fact it wasn't. She doubted that she'd ever allow another guy to get that close to her.

* * *

 

It was Sunday, two days later, and Jessica still felt terrible about the disaster on Friday night. She wondered if she should call him to console him, but decided against it. She hated making him feel bad, but didn't want to make the first move. Especially not one that he might misinterpret as interest in him.

 

After doing housework, she we reading 'The Nanny Dairies' and drinking a bottle of wine, when a knock came at the door. She put in the bookmark, put down the book, and went to the double locked door. She wasn't expecting anyone, and hoped it wouldn't be Matt. She couldn't take that. She peeked through hole, and was relieved to see that it was some girl. She had her back to the door, looking nervously at her car. Jessica didn't recognize her, but she opened the dead bolt and the chain.

"Hello, can I help you?" she said.

"Hi Jessica, can I come in?" said the girl. Jessica looked at her face, and was suddenly shocked when she recognized her. It was Matt.

"Matt, what the hell are you doing?"

"Please, call me Mary" he said.

"All right 'Mary' " she said angrily, "what he hell are you doing?"

"I'm doing what it takes to be with you. If you'll only date me if I'm a girl, then that's what I'm going to have to do. I'll be a girl if that means I get to be with you."

"You're not a girl! You're a guy in a dress with a wig on."

"No! I'm a girl. Your girl."

"Matt or Mary or whoever you are, you don't want to do this. Not for me. Find someone else."

"There is nobody else. You are the one. I cried for a whole day, and couldn't eat or sleep. I realized that this is what I had to do. I've made up my mind. I'm a girl now, for you."

"But wearing women's clothes doesn't make you a girl. You don't have the right body. You don't have the right brain. You don't know how to be a girl. You don't want to be one."

"Yes I do" he said emphatically. "I need you. I need to be yours. So I need to be a woman."

"Please don't do this."

"My mind is made up."

Jessica didn't know what to do. This was totally unexpected. She invited 'Mary' to come in and sit on the couch.

"You're sitting wrong. You're sitting like a man. Watch me. You need to hold your skirt like this so you don't wrinkle it by sitting on it, then sit down like this, and keep your legs this way."

Mary tried it, and Jessica had 'her' practice it a few more times while she went to make some margaritas. She needed a strong drink. Or two.

 

As they sipped their drinks, Jessica's mind was whirling. She didn't want this. Matt couldn't be a woman. He didn't know what it really meant. He didn't understand what he was trying to get himself into. She finished off her first drink, and went to get a refill, although 'Mary' was still on 'her' first one.

As she poured the cool green liquid into the tall glass of ice, an idea came into her head. She smiled. She knew what to do. She would scare him off. Make him do things that would challenge his male pride, and force him to concede. Yes! Once he thought about doing some of the things she had in store for him, he would back down right away.

"Well Mary, drink up. Once you're done, we're going shopping. The mall's open late."

"Cool" said Mary.

Jessica shook her head. Did this guy really think that he'd be able to go out in public dressed up as a girl? And go buy things like bras and panties? Try on dresses? High heel shoes? She thought that after one hour, he'd be so scared that he'd just run. His inner male wouldn't like being treated like a woman either. He'd rebel, and run away for sure.

 

But as they left the mall, Jessica was shaking her head. Not only did Mary go through everything from getting fitted for a bra, to buying matching nighties with Jessica, to getting a manicure and pedicure, to buying frilly lacy things, but she actually seemed to enjoy it! Jessica made her get her ears pierced, and picked out a pair of dangly feminine ear rings. Not ones that a male could ever wear. But Mary smiled, and seemed to enjoy it! He didn't even seem upset when she told him that he'd have to wear them for weeks without taking them out, or else the new holes would heel and close up.

In fact, the speakers announced that the mall was closing before they were even done with all of the things Jessica had planned in her mind for him. But nothing seemed to sway him. Once they got back to Jessica's place, the moved all the shopping bags from her car to Mary's.

"I realize that at work you'll have to masquerade as a guy" said Jessica. "You can be Matt in the office, for now at least. But as a symbol that you're really a woman now, make sure you wear your red panties and bra you bought. I'll be wearing mine to, so we can be like sisters."

"Not a problem" said Mary, smiling.

"And when you come over tomorrow after work, make sure you've used that Nair we bought. I don't want to see any of that ugly hair on your legs, chest, back, armpits, or anything. Got it?"

"Of course" said Mary.

Jessica gave her a light kiss and a pat on the butt, sending her off.

 

* * *

When Jessica saw Matt at the office, she smiled. He had the dangly ear rings in, as he was supposed to. He had used nail polish remover to make his nails look manly again. She would have to work on that, since it was obviously a weak point for him. She laughed to herself when some of the guys teased him that he had such 'girly' ear rings. But he just shrugged it off.

She waited until the time was right, and she met him alone in conference room 3. She shut the door behind them.

"Lets see it" she said.

Matt had worn a dark colored shirt that day, so the redness of the bra wouldn't show through. He had no breasts, so it laid flat against his skin, and you couldn't tell he was wearing one. She knew that she was going to limit him to white shirts from now on.

He unbuttoned the shirt to show off his newly hairless chest, and the red bra with the frilly lacy edges. She pulled the cup back, exposing his little tiny nipple. She licked it, and gave it a kiss. Electric shocks surged up and down Matt's spine.

"Once you have real breasts, wait till you see how that feels" she said, buttoning him back up.

Matt was walking funny, evidence that he had been highly aroused by the episode. Jessica didn't know if she liked that fact or not. She would have to use that against him too.

"Make sure you arrive on time tonight" she said before they walked back out. "I have something special planned for you."

Matt smiled. He couldn't wait.

 

* * *

When 'Mary' showed up at 6:30pm sharp, she was dressed up in her new outfit. She wore a short black skirt, dark pantyhose and heels. Her white blouse was semitransparent, clearly showing the bra underneath. The cups were still empty though, so 'her' proportions looked manly. But Jessica would work on that.

"Hello lover girl" she said as Mary strutted in, with her new walk she had been working on. "I have some gifts for you I picked up at lunch time".

Mary was eager to open the bag, pull out the tissue paper, and find what Jessica had bought her.

"Oh thank you, that's so sweet of you!" she said. Jessica shook her head. Mary seemed eager, but her nail polish was sloppy, and her makeup was poorly done. The would work on that tonight.

First, Mary found a box which contained two silicon breast forms.

"I found them at a store for women who've had breast cancer. Go put them in, and come back!"

Mary did so, and when she walked out of the room, hew new large breasts make her look so much more womanly. Jessica smiled. For the first time, Mary looked just the least little bit attractive. She remembered back to when her own breasts had started growing, and how she felt as her bra had filled out. She was a girl, and she hated it. Oh how his male ego must be suffering! Yet, he continued to smile.

"Now I'm like you" he said.

"Not quite. You can take those out any time. But once you have *real* boobs, then you'll be like me."

Mary reached in for the second gift. It was a jar of breast cream.

"I don't know how well it works, but follow the directions, and put it on every day. It claims that in a couple of months, you will add an inch and a cup size to your bust. Make sure you don't forget to do it!"

"I won't" said Mary, reaching in for the next item. It was a jar of vitamins. Isoflavones, which are naturally occurring estrogens found in certain plants.

"They're just like real female hormones. Take three of those a day. We need to start to flood your system with estrogen, if you're going to be a woman."

"Can I take some now?" asked Mary, to Jessica's amazement.

"Sure babe, knock yourself out."

Mary went and took the three pills, then returned to pull out the last item from the bag. It was a purse, with a long thin strap. She put it over her shoulder, and admired how it looked.

"Go ahead, look inside. I put in a few things that a woman can't go without" said Jessica.

Mary looked inside, and found a compact, mascara, and lipstick, so she could fix up her face when she was out and about. There was also an emery board to fix her nails, a little coin purse, and two tampons."

"For 'that time of the month', in case you start flowing when you're out and about" said Jessica.

"Thank you so much. I feel so bad! I didn't get you anything" said Mary.

"Don't worry. You can make it up to me later. Now lets get down to your assignments."

"Assignments?"

"Yes. If you're going to be a woman, you need to do some things every day for me."

Jessica handed a piece of paper to Mary, who read through it. Jessica hoped that Mary would throw down the paper, and run. But she didn't. The list read:

 

-Wear your bra and panties at all times.

-Only wear white shirts so your bra shows through.

-Wear nail polish at all times.

-Use your breast cream every day

-Take your vitamins every day

-Wear dresses and skirts at all times, except for work (for now).

-Wear your breast forms when you are not at work (for now).

 

The last item was one that Jessica like the most. It said that every day, Matt had to throw out or donate to the poor one 'male' thing he owned. Every day, Mary had to buy one 'female' thing.

"So you could donate a pair of work boots to the poor, and go buy yourself some pumps. Or throw out your DVD of a war movie, and replace it with a chick flick. Sell off your sports books, and buy romance novels. Things like that. Keep it up until someone walking in to your place would say 'this is a girl's house'."

"Sounds good to me" said Mary.

Only then did Jessica realize that perhaps Matt was really serious. But she pressed on with the other things she had prepared for Mary. First, she had Mary remove the poorly applied nail polish, and showed her how to do it properly. She did a couple of nails, then had Mary do the rest. After it dried, they removed it, and Mary did it again. She was getting better and better at it. Jessica had picked out a light pink shade, which was only a little darker and more even than the natural color you see in a person's nails. That way, 'Matt' wouldn't stand out too much wearing it in public. She had Mary put on two coats, and a sealer.

Next, Jessica handed Mary a white bra.

"This is the latest in brassiere technology. It is meant to shape and enhance your bust line. It adds half an inch and a cup size to any breasts. It has gel pacs built in. It lets a girl with small breasts look more attractive to men. This is what you are going to wear to work."

Mary took the bra, and admired it. She started to adjust the straps to fit her larger shoulders.

"Now Mary, when you're wearing this, you will have a definite bulge under your shirt. You won't be able to miss it. You're going to wear this every day, until your own boobies get big enough that they show on their own."

"Can I put it on now?"

"Sure kid. Go for it"

Mary put the bra on, and came back out. The only way that someone would not notice this bra would be if Matt wore a sweater, or a suit with a jacket. But Jessica was going to forbid that. Everyone would be able to see that Matt was wearing a bra. This would scare him off for sure.

"You can see it through the shirt. You can see it bulge out" said Mary.

"Yes you can."

"Cool!"

Jessica was besides herself. What else could she do to scare him off? It was clear that he wasn't going to be scared off by frilly feminine things. She had one last ace up her sleeve. She would wait until the next day to play it though.

* * *

 

At work, Matt received many stares. There had been talk about the ear rings, in the whispered office conversations. But now, it looked like he was wearing a bra! And his chest definitely was bigger. It looked like he was growing breasts! The place was abuzz with rumors of every kind. Some even said it looked like had nail polish on. The men avoided him like the plague. But the women were suddenly giving him a lot of attention. But he didn't even care about them. There was only one woman as far as he was concerned.

Matt was oblivious to it all, floating on air. He was in love.

 

In the early afternoon, Jessica came over, and told him to follow her. They went into the copier room, and she shut the door. She rummaged through her purse, and produced a brown paper bag.

"Here love, this is for you" she said.

"Wait. I have something for you" said Matt, handing to her a small present. Jessica unwrapped it, and found a book of poetry.

"Thank you, that was very sweet of you" she said.

"I bought it for you when I got rid of some of my sports books yesterday, and replaced them with art books."

"Wait until you see what I got for you!" said Jessica.

Matt opened up the paper bag, and pulled out two discs, with numbers 1-31 on them. The top rotated, and there was a small opening in it.

"What are these?" he said.

"Birth control pills. I went to my doctor at lunch time, and got a prescription for good ones. The dispenser is designed so you don't for get a day. Do you know what happens to a woman's body when she gets pregnant?"

"A baby grows in her" said Matt.

"Well that, plus a lot of other things. All sorts of hormones start flowing inside you. You gain weight. Your breasts swell up, so they're ready to deliver milk to your baby. It effects your emotions, your brain, your skin, your body...it prepares you for being a mother. Some hormones will trigger the nesting instincts within you. Some will trigger the nurturing side of you."

"And you want me to take these?"

"Yes. Every day. But you can skip the brown ones."

"Why?"

"They're inert. They are just so you keep in the habit of taking one every day."

"Why would you do that?" asked Matt.

"Your period. Your monthly cycle."

"Oh. I get it" he said, but she wondered if he really did.

"Do you know what all these female hormones are going to do to your male body?" she asked.

He shook his head.

"Well, as I said, they're going to start to alter you. Your breasts are going to start to grow. Real breasts, on your body. If you keep it up long enough, you're going to be stacked. Between your vitamins, your breast cream, and these, you are going to have real breasts. How does that make you feel?"

"Excited!" said Matt.

"And it will effect your manhood. It takes a certain hormonal balance for a man's body to function sexually. As you keep taking these, it will throw off that balance, and you will become impotent. You won't be able to become sexually aroused anymore. That ugly thing between your legs will just lie there, limp, at all times. You won't be a real man anymore."

"I don't want to be a man anymore" he said.

"Well, you're not going to be. Get used to it."

"Cool" he said.

* * *

 

For the next week, things carried on as they were. Matt was in love, and totally consumed with his passions for Jessica. She didn't give him anything more than the occasional kiss, but that was enough to keep him going. He didn't even care that he was being turned into Mary. He didn't care that he was about to grow real breasts. He didn't care that he dressed up and acted like a woman all of the time, except when he was at work. He didn't care there that all his coworkers knew that he was wearing bras and makeup and nail polish. None of that mattered. Only his love for Jessica.

Jessica tried a number of other things to scare Matt off. But nothing seemed to work. After a month, she knew that it was time to finalize things one way or the other. She invited Mary over that night. Now that Mary's place looked like a woman's home, they split their time between the two abodes. But tonight, it was Jessica's turn to host.

 

"Mary, we need to talk" she said.

"Sure Jes, what's up?"

"Its about this Matt thing. I don't think I can take seeing you at work anymore, pretending to be a man. I feel like you're cheating on me, being someone else. It has to stop. If we're going to stay together, you can't do that anymore."

"You mean, I can stop pretending? I can be me all the time?"

"Yes. I want you to go in to work tomorrow as Mary. Tell your boss that you're Mary now, and get the paperwork going to officially change your name at work. Then we'll go to the DMV and get your drivers license updated too. Its time for you to quit your charade, and be a woman all the time."

For the first time, Mary seemed less than fully enthusiastic.

"And here is a card for Dr. Wagoner. Make an appointment to see her. She can start you on full female hormone therapy, in addition to what you're already taking. She'll want you to get a bunch of psychological exams and stuff, then you can start your schedule"

"My schedule?"

"For your operations. After they surgically create a new vagina for you, you might want to get hip implants, breast implants, surgery on your face, adams apple, and other stuff. Do you know how they do a gender reassignment surgery these days?"

"No" said Mary, sheepishly.

"They don't just cut off your penis. They actually split it open, turn it inside out, and use it to create your new vagina. So you will feel somewhat of aroused sensation when you are penetrated. Isn't that exciting? I bet you can't wait!"

Mary just stared back.

"And then there is one more thing. This is embarrassing, but I need you to help me."

"Anything" said Mary, eager to please Jessica.

"My aunt Kathy is getting remarried, and I'm standing for her as a bridesmaid."

"That's wonderful!" said Mary.

"Yes, but there's a problem. She doesn't know that I'm a lesbian, and if she did, she'd throw me out of the wedding. She's very conservative, and like most of my family, she doesn't know."

"So you want me to go as Matt?"

"No. There is no Matt anymore. We will each get a guy to go with us as our dates. Just for the day. Then we can go back to being a couple. But I have to pretend, for her sake."

 

Now it was coming down hard on Matt. He would have to show up to the office dressed as a woman, and tell his boss that he was 'Mary' now. They he had to go on female hormones, and sign up for a sex change operation. And he had to go on a date with a guy.

Jessica smiled. She should have insisted on this earlier. He would be scared off now, and her problem would be solved.

"I'm not sure" said Mary, which made Jessica feel triumphant.

"About what hon?"

"I've never gone to a wedding as a girl. I don't know what to wear."

* * *

 

The second wedding that Mary ever attended was the one where she was one of the brides. She and Jessica were wed in the courthouse, with only their closest family and friends present. They held hands as the boarded the plane to Hawaii for their honeymoon in Maui. They sipped mai tais with little foo foo umbrellas, and smiled at each other. They were two women in love, and were flying into the sunset, on a romantic trip as they started their new lives together....

  

  

  

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