The Door Left Unlocked Pt. 02

Chapter 3

Bryan goes public in a dress

On Friday they talked about the coming week. Both agreed that the weekend was not the best time for him to try appearing in public, because more people were out during the day. They decided to relax around the house instead. Becky called Wendy and told her they were going to try going out on Monday, but the weekend was scheduled for stay at home. Wendy asked if she could stop over and Becky and Bryan both agreed it would be fine.

Bryan was actually a little worried about her being there. He had been thinking of the fun they had had together on pool day and now his cock was beginning to respond. He talked to Becky and they came up with a schedule for clothing. Friday morning, they were both lounging in shorts and t-shirts. In the afternoon, a bright, sunny day, they would strip and stay naked the rest of the day.

Saturday was also supposed to be sunny and hot, but they agreed he would wear women's clothing, with the bra until noon, without until around 2. Then they would swim, naked again. Before dinner they would dress in each other's clothes, just to be different. Sunday the forecast was for cooler weather and rain. That would likely keep them indoors, so that was a 'do whatever you want to do' day. Monday he would put on his dress in the morning and they would drive to the mall in Rileysville, a slightly larger town about 35 miles away. They would shop for clothes and have lunch in the food court. Some time after 3 they would return home. He would have about 4 hours of exposure in a place where probably nobody knew him.

Now with a plan they agreed on, despite Bryan's nervousness, they had lunch and then, in accordance with their plan, they stripped completely. It was liberating and awkward at the same time. The idea of being naked and going about everyday things was exciting, but seeing their step-sibling naked was really off the charts strange. He found he kept looking at her pussy, expecting at some point to see loose lips extending, but they never did show. He'd been with a half dozen girls, and they had loose folds of skin that were very obvious. It wasn't that he liked Becky's pussy more or less, but it was different. Once he told her what he was going through and she blushed, crossing her legs. Maybe naked, he thought, but she still doesn't want him staring at her pussy. He could handle that.

He was hoping Wendy would arrive, but she called Becky and said she had to work a full day. Becky reminded her to try to get out on Monday and was told that was already sealed. She didn't realize how hard interns for politicians had to work, but her pol was a decent lady and when Wendy pointed out she wasn't actually getting paid, she smiled and signed the leave request. She said she wanted to be there, with Bryan, on his first day dressed in women's clothes in the large world.

That was it for Friday. There were burgers left over and Becky heated them while Bryan heated some beans. They had a couple of beers and questions began. After the dinner conversation continued, and by bedtime they each had a pretty good idea of what each others' lives had been like before they went to middle school. Becky was impressed by how dearly Bryan remembered his dad, despite what he had said about his father's relationship with him. Bryan was shocked by how badly her mother had treated the family and how hard Becky's father had worked to build up his business while trying to get his wife into rehab and keep her dry when she got out.

They went to their separate rooms and beds and slept there, still naked, feeling closer than ever. More importantly, as he heard what Becky had put up with as a child, he appreciated more how he and his mom coming into the house created a situation that so easily led to resentment. She saw that Bryan was actually a little insecure, having relied so much on his dad and then not having him. Bridges were built. Bridges that would be important in the next couple of weeks.

Saturday went according to plan. Wendy called in the morning to see if she could stop over and Becky playfully told her they were stripping at 2, so that would be the time to strip or leave. Wendy showed up at 11 and was surprised to see Bryan with the filled bra.

"Are you planning to get implants? Trying out the look?" she asked him.

His smile was half-hearted. "We agreed I would do this to see if it's the dress or the girlish look that I want. I guess Becky has a point that I've made up my mind why I'm doing this without really doing all my homework."

"Ok," she replied. "Sooooo, boobs?"

"You need something to play with?" he asked.

Her smile was sincere and wide. "You already have something to play with. That's all I need."

His blush was as sincere as her smile. Becky caught the end of that conversation and asked him if he wanted an early change to no bra. He glanced at Wendy and shook his head. She was looking at his "breasts" and he liked it. They sat around talking until time for lunch, then he kept the boobs in for lunch, only removing the forms and bra after lunch.

Wendy noticed right away. "I admit, I think you're quite sexy in a dress with those forms in there. If you want to be more of a girl, I think you'd look really great."

Bryan looked at the girls looking at him, especially Becky. "Yeah, I know, it looks good, and it looks sexy. But the only guy I'm trying to look sexy for is me. Can we drop that line of talk now?"

Becky shrugged. "For now. I told you, you need to face it. You might not want it, might not like it, but right now everything you do is screaming that you want to be a girl with a cock, not a guy in a dress. Hey, Wendy, you didn't grow up around here did you?"

The conversation went off in another direction and Bryan was happy Becky cared enough to go there and Wendy seemed to care enough to follow the bread crumb that had been tossed her way. He still expected Becky to turn into what she had been for 5 years, but so far she seemed to be really trying to be a different person.

Becky's phone alarm went off at 2 and Bryan commented about how suddenly she was punctual when it came to taking off clothes. They joked about the history of his dedication to timing and her total lack of concern with time. Wendy said she fell somewhere in the middle. It was more dependent on what she had to do.

Aware there were two women with him, even though one was his sister, Bryan made a point of not running off with Wendy. He didn't fully trust her, but Becky had done so much, and overall been so nice and understanding, that he didn't want her feeling like the one left behind. Around 5 she went to look at food options and Wendy and Bryan jumped into the pool, swimming a few laps in their unofficial end to the swimming day.

As he held the edge of the pool in the deep end, Wendy swam half the length of the pool under water, popping up right in front of him. She hugged him, kissed him, used her tongue to seek entry and received permission, and she rubbed on him. With all the attention from a girl he liked, this time he did respond. He tried backing away a little, but then her hand was on his cock holding him close.

Wendy kissed his cheek, nibbled his earlobe, and whispered, "I take birth control. Maybe not now, but soon I would like the boy part to come out from under the dress and do something very manly."

Bryan knew there were some questions you were never supposed to ask, but he thought it and out the question popped before he stopped to think about it. "Wendy, how much experience have you had?" As soon as he heard it in his ears, he winced.

She pushed away a little, still holding his shoulders in the deep water. "I should be really mad at you for that question. The only thing saving you is that you seem to be pushing the direct route as you start showing people how you look in a dress." She mumbled something else he didn't understand. "I've had at least 150 guys fucking me since I was 16."

He shook his head a little and looked at her. "Seriously?"

She gave a grin. "No, you dingbat. I wanted to shake you up for asking. I've had experience, and if we go to bed you will be able to enjoy my experience. I've also been hurt by a bastard who I found out is just a conqueror, but has no interest after he's gotten the big three." His eye were questioning and she sighed. "Three? Shit. Mouth, pussy, ass. Bryan, I think I really like you, and it scares me a little."

He laughed a little. "I love that Becky is supportive, but right now I wish she was somewhere else."

A minute later, Becky came out and said she didn't feel like cooking. Bryan and Wendy agreed they didn't feel it either. Becky called for another couple of pizzas and they played a quick game of high card to determine who would put on clothes to greet the delivery person. Wendy won. Becky told her the pizza and tip were already paid and all she had to do was accept the pizzas and bring them in so they could sit on the patio and enjoy.

Finished with the business of arranging the meal. Becky and Bryan returned to the pool area as Wendy reached for her shorts. The step siblings chatted about how strange the world had become in a week. She talked about how great it was that Wendy seemed to like him, and she hoped there was at least a little spark there because she knew he didn't go out with girls much.

Yeah, he thought, that was a problem with attending the same college. She knew his social life was pretty flat. It wasn't that he tried a lot and failed. He just really wasn't trying. He didn't just want a girl, he wanted a good girl who might be the right girl. They were in much shorter supply than the girls who just wanted to go out and maybe go to bed.

"I'll tell you what's maybe the weirdest to me," he told his sister. "This thing with Wendy. I've known her almost as long as I've lived here and we were just sort of nice to each other. Now she sees me in a dress and wants to take me to bed. I really can't understand that at all."

"What did you think of her for those years?" Becky asked.

"She's cute. I mean, she's really cute, and she's got all the stuff a guy would like. But maybe because she was your friend, I never considered anything else." He was quiet for a moment. "Maybe I actually liked her more than I realized but it's only now real enough to register."

Becky stretched, then turned to look at Bryan. "It's my fault, I think. She liked you from the beginning, thought you were really nice. I told her, well, I wasn't very nice about you. Maybe she thought it was true, or maybe she didn't want to make me mad." She looked down. "Bryan, Wendy has been trying to get your attention for a couple of years. Your courage, and my support, nailed it and she decided to let it grow and see what happened."

They heard the doorbell. "Wow, I had no idea you were so mean to me that you would try to keep me from being happy about something, not even letting me know you were standing in the way."

Wendy came walking out carrying pizza boxes, wearing just her shorts. She was frowning.

Becky looked at Bryan, then asked, "What's with the expression? Is the pizza burned or something?"

The shorter woman put down the boxes and stood for a moment, looking at the door to the house. "I decided to be a little crazy and answer the door like this."

Bryan suddenly blurted out, "You flashed the pizza guy?"

Wendy looked at him and took a step back. "Well, that was my plan, but it was a girl. And she told me she didn't appreciate people answering the door naked. She took a pretty big piece of my hide and handed me five dollars saying she didn't want a tip from assholes. I couldn't get her to take the money back. I was just having fun and I ruined her night."

Becky jumped in as Bryan got up and walked over to Wendy, cock dangling loose. He hugged her, tightly, as Becky told her, "Call the store back, or I'll call them, we'll apologize without saying exactly what happened, and tell the boss to make sure she had the money in her tips."

"But I have her money because they would have already credited her account. I don't feel very hungry now." Wendy leaned against Bryan, arms at her side.

"Look, we'll find a way to make it up to her." Bryan turned her face up to his. "Besides, we still like you. No matter what I thought in the past."

She looked at Becky, who was looking at the patio. "You told him?" Becky nodded.

Before anything else happened, Bryan moved her face back toward his and kissed her. It was a long, deep, tongue-dueling kiss that ended with him holding Wendy tightly against him as he blushed a little. Wendy giggled and looked at Becky. Becky had her hand over her mouth, but her eyes were smiling.

One hand slowly moved away from Bryan's back, then returned to sharply spank his ass. In surprise he relaxed his hold and Wendy stepped away, turning to Becky and announcing, "I think he likes me."

Bryan struggled to cover his fully erect cock, which he had been trying to keep hidden by pressing it between their bodies. He backed up and sat down on a chair, his hands in his lap. "That was mean," he said.

She laughed a little. "No, sweet guy, that was naughty. I don't think your sister wants it, and you've seen her."

"Yeah, ok, I've seen you both naked, but not aroused, wet pussy, hard nipples. Come on, this is embarrassing."

"Ok, Wendy, that was quite a show, but it might have been more than I needed to see. Your penalty is that you must get me a beer and one slice of each of the pizzas." Becky was trying to rescue the situation, and Bryan thought she did a pretty good job. He had been half afraid she would just offer to show him.

Late in the evening, Wendy got dressed and left, but not before another kiss that left Bryan erect and panting. She took his hand and guided it down to the leg opening of her shorts. Sliding her grip down to a finger, she moved it under her panties and rubbed it on her lips, letting him feel the moistness. Then she moved away, found Becky to say goodbye, and left.

Becky noticed the softening shaft and looked away. "What do you think now, Bryan? Do you want her, her pussy, or do you want her to leave you alone?"

He turned a little bit. She may be his step-sister, but somehow it didn't seem right to flash his cock at her. "I need to think. I'm really confused. I want her, but I want it to be right. Am I making sense?"

She walked up to him, making him very uncomfortable. "You want to have sex with her, but only if she's THE one, or at least the one enough to keep up the pursuit. Let me see. Stop hiding it. I think we both need this." He turned back and she held his now soft cock in her palm. "There is no doubt in my mind that she would love having this inside her. And I think she would be impressed that you care enough not to try to just shove it in."

"Ermm, Becky, this is really weird." He looked at his cock in her hand, starting to grow again.

She gripped it and stroked it a few times. "If you weren't family, well, I've, had, uh, I, never mind." She dropped it and turned but he grabbed her shoulder.

His hands shook a little as he looked into her eyes and saw desire there. "Hey, sister, if we weren't family, and you'd had no reason to be a bitch for 5 years, maybe. But I don't want to mess up where we are with jumping into bed together. And you supported me. So what are you so afraid to tell me?"

She reached up and put her hands on his. "I may not be so different from my mother."

For a moment, Bryan let that settle into his mind. "I don't see a problem with the beer, so I assume, well, let's say, too many friends?" She nodded. He nodded back. "If you don't like it, why do it?"

Now she stepped back. "Well, I mean, I like it. Usually, at least. It's just, you know, the guys aren't that interested in me. We go out, we have a good time, we end up in bed. Then I call and half never pick up. Maybe a couple of dates and they've moved on."

"I'm guessing some of these guys were at college?"

"Most," she answered.

"Do they know we're family?" He was calm, spoke softly, but she still tensed with a flash of anger.

"Not if I could help it," she replied. "It does help that we have different last names. OH!" She suddenly realized she had gone Old Becky on him. "I'm sorry, Bryan. I don't mean it to sound like that."

He smiled. "Yes, you did, but you're trying to change. We both know I'm not the guy you're looking for. Let me think about it overnight and see if I can do anything tomorrow."

"Suddenly Mister Neverdate is a match maker? I'm curious to see what you come up with. Now, I've had a long day and I'm going to bed."

Bryan resisted the urge to smack her ass when she turned. His mind was in turmoil. She was his step-sister, who he was finally beginning to think of as a sister, and she was really good looking. Part of him, a prominent part when he was naked and excited, really wanted to roll on the sheets with her, and he knew, especially now, that she would do it. The more reasonable part knew he wanted to keep that under control. It wasn't easy living with a sister, he decided, and he went to grab another beer and sit near the pool.

Sunday was rainy and cool, and they spent the day indoors with shorts and t-shirt on. In the afternoon they spent some time outside, but most of the day was indoors. At one point he commented about how hard it was going to be dressing properly again when their parents returned from their cruise. She laughed and pulled off her shorts, telling him it was healthy for him to see her half dressed.

Monday was the big day. Wendy was over by half past 9 and watched as Bryan finished his makeup. She made a few suggestions, but told him he was doing an amazing job. Today was going to be totally as a boy in a dress, so there was no bra, no forms, and because the day would be long, stockings instead of pantyhose. His panties were black hip huggers that fit snuggly enough to keep him tucked without the constriction of pantyhose.

Becky drove them to Rileysville and parked far from the entrance to the mall. She said it was to give them a chance to relax and flow with things, though she added that until Bryan talked, he looked good enough that most people would probably think he was just a flat chested girl.

They walked in at the middle, turned right, walked to the anchor store at the end, turned back and went to the anchor store at that end. By then they had gauged the reactions and realized most people didn't even notice them. Satisfied with that, they turned into a women's clothing store and started looking at dresses.

The salesperson came over to ask if she could help, but for the first few minutes she was mostly just making sure it wasn't some kind of joke. It took both girls to convince her that he really wanted to try on a few dresses. After his third dress, which all agreed looked really good on him, they were all more relaxed and were joking.

They stopped in two more stores with much the same pattern, and had he two dresses by the time they were done. The next stop would be for panties, bra, and possibly a garter belt, and all agreed that lunch would be best before taking that step. They went to the food court and got some burgers and cola, then sat down to eat. By this time, Bryan was getting more attention, and not all was encouraging. He realized that some were just disgusted because of preconceptions, but others were smiling because they thought he was the girls' pet. He shared that realization and they agreed to try to ignore both groups as simply not willing to accept people who were different.

It was easier to decide than to do. They finished up and dumped their trash before heading for the lingerie shop. Bryan was surprised that the salesperson at this shop didn't make any judgements. She made a few suggestions, asked a few questions, and recommended a bra for forms and another for no forms. And of course, she said, he could always wear no bra, but since he seemed to enjoy the feel of the underwear, the bras would be a good investment.