Dares Become Reality

Dares Become Reality

"Did you go through with it?"

Eric smiled as he saw the message in his inbox on the fetish site he'd joined weeks ago. Following a few relationships that had gone nowhere since moving to Boston, he decided to have some fun and try to meet women on kink and fetish sites. Nobody in his real life knew that he liked to wear lingerie and feel girly, but he could explore online for fun.

"Yes, I bought 5 pairs of panties and some pantyhose," Eric replied to YourFemGoddess, a woman who had messaged him after he had uploaded some faceless photos and written on a kink site about how he liked exploring his feminine side. At least Eric thought YourFemGoddess was a she. He knew that people could make up whole personas online, but the chats over the past few weeks were too hot for him to question it anyway.

"I bet you're dying to try them on you naughty thing. Put on a pair and send me a picture. I know you want to ;)"

Eric did want to, but he also wanted to know more about YourFemGoddess. Maybe now he finally had a chance.

"OK, I'll send you a picture of me in panties. But will you tell me your actual first name and maybe send me a picture too? After all these weeks, I want to know who I'm talking to here."

This time, the response wasn't fast. Eric figured he had just pushed away the one person who he had confessed so many of his secret desires to and that he'd ruined something special. He was about to apologize when the little envelope in the corner turned red.

"If you send me a picture in one of your new sexy things, I'll send you a photo back wearing something of the same color and my first name, but you have to let me control you with assignments every day for the next week. Deal?"

This was better than Eric had ever dreamed. He quickly reached into his shopping back and put on a pair of white lacy tanga style panties and he snapped a picture with his phone, cropping out his face. When he looked at it, he saw just how hard he was in the sexy panties and he was enjoying himself so much that he took a couple pictures in other poses to show off before uploading them in the chat and sending them to YourFemGoddess.

This time there was an immediate response. His secret friend wrote back "Yum. How exciting! Wait a few minutes for me to send something appropriate."

Ten minutes later, Eric received the next response. It was a photo of a long leg in white stockings and the message simply said "Look for your first assignment tomorrow morning. - Julia."

Day 1

When Eric woke up for work, the first thing he did was grab his phone and look for a message from Julia. When he saw nothing, he was disappointed and started to get ready for his day. He showered, brushed his teeth, and got dressed, checking his phone one more time before grabbing his keys.

It wasn't until he got to his car that Eric heard the alert on his phone. He smiled when he saw the note.

"I kept you waiting on purpose to see how willing and eager you would be to obey. Go put on some panties to wear under your work clothes all day. Make sure to send me a picture during the day so I know you're doing as I asked. - Julia"

Eric's legs got weak as he read the text. He wasn't too surprised by the task. All night, he was thinking of what he'd be asked to do. Now he rushed back inside his townhouse and stripped down, changing into a pair of red bikini style panties before putting his pants back on to leave for the office.

All day at work, Eric shifted nervously in his seat and in meetings. His coworkers were mostly women and he had secretly wanted to dress like many of them. Today he was wondering if anyone would have any idea what he was wearing or if, like some women he'd seen, there may be some lines showing under his pants.

Instead, nobody seemed to acknowledge Eric much at all. He mostly kept to himself, so this was not uncommon. Lisa, one of the HR specialists, exchanged her typical friendly greetings. Monica, the finance director who recently turned 40, asked Eric about his weekend. Carrie, his teammate in the marketing department, talked so much about her own week and personal drama that Eric could barely get one word in at all during any conversation.

It was when his supervisor, Courtney, was discussing the upcoming projects with him that Eric's phone beeped again and he saw that he had a message from Julia. Courtney was divorced and in her mid 40s. She was fit and professional, always friendly but also taking her role as an Executive Vice President seriously. Her heels took her from an already taller than average 5'7" to closer to 6'0".

"Are you distracted by something?" Courtney asked as Eric looked down at his phone. The message read "I hope you're enjoying your first task. If you want another, send me a photo within the next half hour. Julia."

"Excuse me? No no, I'm good. Just um, waiting for an update on an appointment I have scheduled. I'm sorry." Eric was flustered but excited as he sat across the desk.

Courtney shook her head at her absent-minded employee and then returned to the business at hand. The meeting was going longer than expected and he anxiously counted down the minutes, not wanting to mess up his first day of assignments. At the 25 minute mark of the discussion, Eric asked if he could excuse himself and he rushed to the men's bathroom, snapping a picture of himself in his panties and sending it along to YourFemGoddess.

He rushed back to Courtney's office and resumed their discussion. When Eric returned to his desk, he looked at his phone and there was the response.

"You naughty girl! You love wearing panties, don't you sweetie?"

Eric looked around to make sure he had privacy and responded "Yes Julia. It is very arousing."

"I'm afraid that panties are too easy to hide Erica. Tomorrow you wear sheer black pantyhose under your pants with nothing underneath. No underwear or socks. And i know you're turned on, but no cumming until I say it is OK. If you can last a few days, I promise you will love the reward. - Julia."

Day 2:

Once again, Eric could barely sleep. He had dated some adventurous women before, but he had been too shy to share this secret side of him with any woman until now. He woke up, showered, and slowly slid on a pair of sheer black pantyhose and then admired himself in the mirror before putting on his pants, shirt and shoes and heading out the door to work.

Just like the day before, Eric felt a rush the whole time he was at the office, but nobody seemed to know about his hidden side. Carrie kept rambling about her regular complaints and Courtney dropped off papers to review just like normal. He wondered if anyone could see a peek of the sheer nylon when he crossed his leg, but nothing seemed to indicate it.

This time Eric had a plan to make sure he wouldn't risk not sending a picture in time if asked. He went to the bathroom and took a few pictures of himself in the mirror in his pantyhose in different poses and saved them on his phone for the appropriate time.

At 3:00, the time appeared to be upon him as he received a message that said "Hey Erica hehe...I hope you are loving those pantyhose. Send me a pic in the next ten minutes so I can see and give you the next task and reward."

Eric responded within one minute, sending a picture from his bathroom photo set from earlier in the day. He sat back in his office chair, excited to see the response.

Moments later, Eric was despondent when he saw Julia's message.

"That was fast. Too fast. You took that earlier today, didn't you Erica? Are you trying to get past my assignments? I thought you were the one who really wanted this."

Eric looked down at his phone and typed fast, trying to not make a spelling mistake as he wrote back to his dream woman. "I do want this! I'm sorry. I thought that would be OK. As you can guess, I've been wearing my pantyhose all day. They feel amazing."

As he waited to hear back, Eric's heart was beating faster, worried that he'd ruined his fun.

"I don't know Eric. Maybe you took that picture this morning and changed back. I think you should undo your pants wherever you are now and take a picture with your watch on your wrist so I know it's you in your sexy hosiery. You have three minutes to please me."

Three minutes to continue this sexual fun or go back to browsing chat rooms with strangers. Eric looked around at his desk. Carrie was talking on her phone, Monica was down the hall, and others were across from his desk chatting. If he was going to do this, he'd better move quickly.

Eric quietly unzipped his pants and opened them up enough to show that he was hard in his pantyhose. He put his left hand over the sheer black top and then snapped a few pictures.

"What are you doing?" Carrie asked as she looked over from her phone. She couldn't see much over the divider and Eric fumbled as he pushed his legs further under the desk, his pants still undone.

"Nothing. Just dropped my phone. Sorry about that." Eric uploaded and hit send and then buttoned his pants back up as quickly as he could, trying to maintain composure.

"Whatever," Carrie said, rolling her eyes as she went back to personal business.

Within minutes, Eric's phone beeped again.

"Much better. You are a very obedient sissy slut, aren't you Erica?"

"Yes Julia I am." Eric had never talked with a woman like this before and it excited him more than any roller coaster ever had in his life.

"If you complete my next assignment, you will receive a reward that I know you will love. My voice. You would love that wouldn't you Erica?"

Eric winced at the reply. She had been calling him Erica without ever asking him and it felt like a loss of control, which he loved more than he cared to admit.

"Yes Julia. I'd love that more than anything."

She responded quickly with another message.

"Before you go home, you must go to two stores. First, since you're already wearing women's stockings, I want you to go to a shoe store and get yourself some heels. Make sure they fit. You do not need to wear them out of the store. Message me when you've done this.

Second, you need to stop at an adult book store and buy yourself a butt plug. I know from previous posts you've made online that you've wanted to try one. Now is your chance. You'll be a good sissy and do this, won't you Erica?"

"Yes Julia. I will."

Julia did not respond. He didn't expect her to until later. Eric was already too committed to stop.

At 5:00, Eric left the office, driving to the mall near his house. He chose a DSW shoe store so that he could try shoes discreetly on his own. After looking around to see if anyone was watching him, Eric picked out a few pairs of heels and sat down, taking off his normal men's dress shoes to try on a pair of pumps.

"Can I help you?" A young woman asked as she looked down at Eric sliding on the shoe.

He looked up, shaking his head and said, "No thank you, I'm ok."

"Well, just letting you know that a more strappy shoe might fit your wide feet better, though it's usually more fashionable to not wear stockings with open toe shoes."

The employee grinned and winked as she walked away and left Eric alone. He let out a slow deep breath and continued searching, finding a pair of heels that fit. When he went to check out, she was there, smiling as she rang him for the purchase.

"Enjoy. I'm sure those will look great on you," she said with a smile.

"Thanks," Eric said under his breath as he walked out of the mall with his new shoes.

He was ready to drive home when he remembered the rest of his assignment. Eric searched on his phone for the nearest adult store and drove there within fifteen minutes. He parked and was about to go inside when he remembered to message Julia.

"I bought some heels, Julia. Now I'm ready to go to the next store."

Julia must have been waiting, because she responded within two minutes.

"Good girl. Now I said that you didn't need to wear the heels out of the store. But you do need to wear them INTO the adult store as you buy your butt plug. Probably get yourself some lube too hehe. If you do this, you can message me at 7:30 tonight on Skype to hear my voice and talk for the first time."

"I will do it." Eric responded quickly. He was more aroused than he'd ever been in his entire life as he slipped the strappy heels on over his nylon feet and walked in and searched.

Eric had never worn heels before, aside from trying on a girlfriend's pair years ago. He tried his best to walk without issue, but this time there was no denying that people saw. While the store was not very busy given that it was a Tuesday evening, one man was checking him out and smiling and the saleswoman grinned at Eric as he looked for what was asked of him.

After browsing for a couple minutes, Eric went to the register with some lube and a couple different butt plugs since he did not know which was best and he did not feel like asking questions. He put the items on the counter and felt a buzz on his phone.

"Now that I think about it, you should buy yourself a dildo too. A real sissy would want to have one. And you are a real sissy, aren't you Erica?"

"S...sorry, one minute," Eric said to the saleswoman as he picked up the items and went back to the aisle. He looked for a dildo that was not too intimidating and added it to his basket, walking back to check out.

The saleswoman smiled at him and made no comment, but Eric still felt a tremendous rush of nerves, embarrassment, and arousal that this person had to know what he was doing, especially as he was standing there in stockings and heels. After he completed his purchase, Eric took a photo of his feet outside of the store and sent it to Julia.

"Yes, I am a real sissy Julia. I will talk with you very soon."

Eric took his time getting home and then rushed to his computer. He put his newly bought items on the bed and logged onto Skype and messaged the name Julia had sent.

Right on queue, Julia responded and they connected. A video came up on Eric's screen of long naked legs on a bed.

"Hello Erica," giggled Julia from behind the screen.

"Hi Julia, it's so good to finally hear you," Eric responded, smiling at his screen.

"Did you buy all of the things I requested?"

"Yes, and I wore the heels inside like you told me to do. I got a lot of looks, but that was exciting."

Julia laughed from her end. "Wow, I am impressed that you are so obedient Erica! I've never done this kind of thing with a man, but this has already been way more fun than I ever imagined."

"I've never done anything like this either Julia, but it's been exciting. Can I ask where you are?"

"I'm from Michigan, Erica. Now stand up, let me see how those pantyhose look on you."

Eric was very eager to comply, standing up in front of his laptop computer to show his body covered in the sheer nylon. As he touched himself, he heard clapping from the other end.

"Oh my! Look how aroused you are Erica! Do you like when I call you Erica?"

Eric touched his legs more and answered. "It is exciting that you talk to me like that, but I think I'd prefer a name that's not close to my name. Like Vanessa or Mandy."

Julia giggled in delight. "Oh those are good names. I'll call you Mandy then. Did you get excited buying all of those naughty things at the store Mandy?"

"Yes, very much. It was such a rush. I'd never bought anything like that. It's like a whole different person than I was even a week ago."

"Because now you're my sissy girlfriend Mandy. I bet when you bought that dildo and those plugs, you thought about how it might make you feel like enjoying cock for real, didn't it?"

Eric winced. He had talked about these fantasies before online, but now he was admitting them out loud. "Yes Julia. That sounds amazing and turns me on so much."

There was more clapping and giggling and then a pause. "Hmmmm, you've been so daring and shown me so much. I want to give you special rewards. You've certainly earned it Mandy. Now that I've brought out your sissy side and let you talk to me, what prize would you like me to give you to show my appreciation?"

Eric responded almost immediately. "Oh Julia. Since you've seen me on this video chat, I would love to see your whole body and face. Please Goddess!"

The leg moved off of the screen before she spoke. "Oh that is a big ask. I thought you might ask, but it's only day 2! If you go above and beyond in the next 24 hours, then I will too, I promise."

"Yes, yes, of course I will Goddess!" Eric, or Mandy as she was now, was too engrossed in the fantasy to even hesitate.

"I knew you'd say yes Mandy. First, for tonight, I'll show you my body here on screen if you first take that dildo you bought and suck on it like it was the real thing."

After a slight moan at even the suggestion, Eric bent over and took the dildo that he had just purchased. He wrapped his lips around the head and slowly started to pump his lips over the silicone toy on screen.

"Oh yes, there you go! A true sissy craves big cock. And you are a true sissy slut, aren't you Mandy?"

"Yes I am," Eric responded with a mouth full of toy.

"Then say it, say it for me. Say that you crave cock."

"I crave cock Goddess. I need it in every way possible and I love how you encourage me."

This time, instead of speaking, Julia stepped in front of the screen to show her body from the neck down. She was wearing a blue lace trim chemise and touched herself sensually over the silky fabric. "It pleases me to hear you say that Mandy. I've never had a man in my life who really appreciated me like you do. So, if you do my next assignment, not only will I show you my face tomorrow, but I will give you my phone number. Deal?"

Eric licked the toy near his face and smiled huge. "Yes, of course, it is a deal Goddess. How can I say no?"

Julia laughed and stood tall. "You've worn panties and pantyhose to work the last two days and sent me pictures. That made me very happy. Tomorrow, you will wear panties again, this time a thong since I know you bought one. And you will wear one of the butt plugs you bought tonight. Got it Mandy?"

"Yes, I will. I promise."

"I know you will, Mandy. Now get some rest. I look forward to seeing you tomorrow. And you seeing me."

With that, Julia blew a kiss and bent forward to turn off her camera. Eric was excited to briefly see her face, but it was mostly covered by her long black hair. He'd never met someone like her and couldn't wait to fully embrace his sissy side for her.

Day 3

Eric slept very well and woke up before his alarm. He was excited for the day ahead of him and to finally see the woman who had consumed his dreams. After showering and shaving, including extra shaving to make him smooth down below, Eric used some lube to insert the steel butt plug that he had purchased the night before, sliding into place inside his tight ass. He admired how the colorful gem looked sticking out from his cheeks as he posed in front of a mirror and then he slipped on pair of sheer red thong panties over before putting on his regular work clothes.

The ride to the office felt different than any other day, even more than the past two when he wore lingerie under his pants. Eric kept thinking about the cool metal toy in his asshole and he felt a mixed sense of arousal and pride for going through with such a naughty dare.

Just like the other days of the week, nobody at the office noticed anything different about Eric. Monica said hello when he arrived and went back to her spreadsheets. Courtney smiled and then met with clients. Carrie continued to distract herself and roll her eyes at Eric when he tried to make small talk.

Meanwhile, Eric was in a constant state of arousal. Today was going to be the day he would finally see Julia. An actual meeting seemed way off in the future, but getting to see the woman who was controlling his thoughts made him excited and he could barely focus on work.