The Door Left Unlocked Pt. 03

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Bryan faces his test, and Becky finds somebody.
15.7k words
4.79
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Part 3 of the 3 part series

Updated 06/10/2023
Created 01/25/2021
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Sunday morning was cloudy and drizzly. Becky was up first and had breakfast started when Bryan walked into the kitchen. She looked out the window and commented that the day matched her mood quite nicely, but he was her ray of sunshine. She hugged him and even laughed a little when she felt him stiffening.

"You know, one thing about you and your tucking is that you don't stab me in the belly so much. I think in that sense I like you in a dress more than in shorts."

He stepped back. "Ok, I hear that, but girls don't wear dresses all the time, and tucking doesn't stop the process, it just holds things in place no matter how uncomfortable it gets."

She checked the eggs. "I don't know if I've said thank you enough for how nice you're being. I've been awake for about an hour and I was thinking, maybe Wendy and I are being unfair saying you need to pass some test. I'll call her later and tell her I decided to skip the strip club thing."

"I don't know if she's quite as ready to drop it. She seems oddly determined to, well, you know."

Becky turned off the heat and took the pan over to the plates. "To get a cock into your mouth? If I tell her it's off, she'll be ok with that. And you," she put the empty pan on the stove and handed Bryan his plate, "you had better start picking things up better. You're on the same track, but she's driving in a sports car and you have a sedan."

"Says the girl who is afraid of getting hurt."

Becky was going to say something, stopped herself, and took a bite of food. "Ok, that's what it's about. Your mother is great, so it's the social misfit thing?"

"That description works. It's not real inspiring, but it works," he said.

"She told me, well, shit, I asked, but she told me why she's so interested in you now. She didn't want me mad at her. It seems she's had her eye on you for years, and she's going to call you on it one day. I hope you have a good answer for her."

"Becky, I feel bad about it." He put down his fork and looked out toward the pool.

"What's the bad feeling?"

He shook his head. "Not a bad feeling. Hey, what you do to me, she does more. I can barely control myself when she's doing her flirting thing and if she flirts with another guy my gut gets all tied up. But it isn't fair. I want you to have somebody."

She smiled. "That's really sweet of you, and it's one of the things I hated for the last 5 years. How can you still be so sweet after what I always did to you? But life doesn't work on plans like that."

"Sure, ok, so now what? Mom and dad will be home Thursday evening, so we only have 3 full days after this."

"Well, step one, dear brother, is to call Wendy. I think it would be nice to get out for dinner today, same place we went to the other day, but with you as a guy." He waited for what he felt she wanted to add. "And you'd better be a good date for her."

It was arranged by noon and Wendy was over to spend the day with Becky and Bryan. She seemed a little quiet and at first didn't sit with Bryan. By the middle of the afternoon, he'd had all the suspense he could handle.

"Wendy, you aren't talking much. That's very unlike you," he said as he tried to smile. Becky gave him a look of 'what the hell are you doing?' "Are you having second thoughts about dinner? Or just being with me." Now Becky rolled her eyes and put her hands up.

Wendy looked down, and when she looked up she was not smiling. Bryan looked at her intently and nodded. "It had to be too good to be true. I'll see you guys for dinner, if you still want me along."

"Bryan, stop." Wendy was still not looking at him. "It's not like that. Oh, it is SO not like that. But, well, I know Becky said she'd take care of it but she had that date yesterday and I thought she might be distracted." She looked at Becky. "I'm sorry to hear that didn't go well." She noticed the surprise in Becky's eyes. "Anyway, I was asking around yesterday and found out there's a, you know, a party, about 25 miles away on Tuesday. I asked a few questions and, well, I signed us up."

Becky now asked, "You signed us up for a stripper party? And when were you going to tell us?"

Bryan sat again and all eyes were on Wendy. She explained, "Well, I mean, when we left it on Friday, things seemed pretty certain. Now Becky tells me it's all off, and, and I'm kind of, I'm sorry, I shouldn't have done it without checking. I'll have to cancel."

Becky wasn't satisfied. "You're upset that you need to cancel? Isn't it just a phone call?"

Bryan looked at her, his face a perfect poker face, giving away nothing. "No, Becky, she's upset because she still wants me to do it. How about we go to the club and just hang out, not get into the stripper thing."

Becky looked back and forth. "Bryan, that isn't how it works. Clubs can't just have male strippers and let girls suck them. That's illegal. But they can rent rooms for private parties. Or is this at somebody's house?"

She was still looking down. "I know somebody who knows somebody who manages a club, actually part owns the club. There's a group of women who meet every 3 months and Tuesday is their day. It's, well, he said it can be pretty messy after the girls are mostly drunk." She looked up at Becky. "I'm sorry, that's, shit. I need to go." She stood up and turned to the door.

"Why?" Bryan asked.

"I need to go because I feel terrible, especially after what happened, the wine and all."

"No," Bryan continued, "we'll get back to that. Why are you so determined to see a cock in my mouth?"

Wendy was still facing the door. "I don't know for sure. I keep thinking it's to make sure, so I don't have to worry about you running off with some guy. Or maybe it's just so you know what it's like. Or maybe it's as simple as Becky says, so you can honestly choose because you tried it and made an informed choice."

"Or maybe to control me?" The phrase 'running off with some guy' was spinning in his head, but for now he pushed it aside. "And how did you know about yesterday?"

She let out a big breath. "Because the friend, the middle man with finding the club, apparently knows your friend, Bryan, and he called me this morning to tell about some big fuck up that kept him from, well, pumping her full of wine was a group plan, according to him. Nobody expected her to say no, and even less expected her brother to defend her." She turned to look at them. "I'm sorry, but there's a network of phone calls going out, and I found out from another source that Carmella is in the network. Last night, the dressing as a girl, it's all out there. And then I called and somebody found out and, it's a mess, and I made it possible."

Bryan looked at the ceiling for a while, then looked at Becky, then back to Wendy. "It's been a great couple of weeks, and we all seem to be taking turns trying to totally fuck it up. But all this stuff you're telling, and you're worried about me running off while you phone guys behind my back. What am I supposed to think?"

She put her head down again. "I'm sorry."

He walked across the room. "Yeah, I'm sure you ARE sorry. There's only one thing we can do with somebody who messed things up so much." He grabbed her and sat down, turning her and pulling her forward across his lap. She stumbled over him, exactly as he had hoped, and he looked at a surprised Becky. "I need both hands to hold her. Do you want to administer the punishment?"

Becky smiled and got up as Wendy squealed. "Hey, wait a minute. You guys can't do this."

"Wendy, my long time friend, I find you guilty of asking too many questions and knowing too much and sentence you to 30 spanks on your bare ass." Becky pulled down the restrained girl's shorts, grinning as she noticed no panties underneath. "Bryan, do you think you can keep an accurate count to 30?"

Bryan grunted as Wendy gave a sudden twist and he had to hold her tighter. "Sure, let's see, 10 comes after 20, right?"

"Close enough." The palm of her hand landed on Wendy's ass, causing a delightful jiggle in the area.

"Uhm, let's see, what number do we start with?" Bryan teased. "That's 1."

Becky moved from side to side, each cheek gradually turning a deeper shade of pink. The jiggling was so sexy to Bryan and he felt his cock harden, straining in his shorts and pressing up to where he knew Wendy could feel it. He made no attempt to hide it, making sure she was aware of his arousal. Finally, he was calling out, "28, and 29, and finally, 30." He watched Becky running her hand over the pink bottom, teasing down between the legs he held. He saw Becky's head snap up and looked, a mix of mischief and surprise in her eyes as she held up her hand to show the tip of a wet finger.

His hand ran up the back of Wendy's leg. "Punishment is complete, but you did admit your wrongs, and you were trying to be helpful, so the court will consider that as mitigation." He quickly moved his hand around her thigh and he slid a finger into her wet pussy.

"Oh shit, no, fuck, stop, hey guys, oHHh .. no, don't ...AAhhh ... Come on .. ohhshhh .. Becky, is that you? StoppAAAHHhnnn"

Bryan quickly realized he could slide in a second finger and Becky was grabbing the girl's ankles, spreading the legs apart and giving her brother better access. Wendy was already worked up and as Bryan added a third finger and kept up a quick pace she was soon panting, then crying out and shaking as she climaxed on his lap. Bryan began slowing his fingers and Becky released the legs as Wendy crested and began to recover again.

He was looking down and a thought hit him. "You want curious? Ok, here goes."

Becky watched in surprise as he pushed his thumb into Wendy's wet pussy and stroked a few times, then slid his thumb up and slid it into her ass while three fingers once again slid into the pussy. He wasted no time before beginning his dual thrusting. Becky looked up as if to say, "Are you sure?"

"Oh FUCK yes, yes yes yes yes... Oh god that feels so good. Hold my legs, oh shit oh shit oh shit .."

Bryan pushed down firmly on the back of Wendy's head and moved his hand faster. Becky spread the girl's legs again, now looking surprised and amazed as she watched the thumb and fingers double fuck her friend. Wendy's cries were more intense than the first time when she came and Bryan kept up his movements, giving her a second orgasm within a minute. Then he pushed in, shook his hand a little, and stopped, holding 3 fingers and a thumb inside ass and pussy. Wendy shuddered a few times before going completely limp.

He looked at his sister, whose face was a huge question mark now. "She said she wouldn't say no if offered again. It was a guess. Actually, I've never done that before with anybody. It just came to me that, yeah, it would work if I did that."

Wendy's voice came weakly to them. "You'll pay for that one day."

He took his hands away from her and she slid off his lap. "Yeah, maybe. Let's see if Tuesday qualifies as a down payment. I'll play your game and see what I think."

She hugged his legs and put her chin on his knees, looking up at him. "Can we call it an experiment? It's way too important to be a game, and if that's how you see it, I won't be there."

Becky had kind of recovered from her surprise. "Bryan, only if you want to, but if we go, we go as all three of us."

They agreed, and then cleaned up. Wendy asked to shower and then used Becky's hair dryer to help get ready. By 5 they were talking normally again and were ready to go.

Tuesday was still in the future and today's plan was dinner, dressed as 2 girls and a guy. He thought Becky's shorts were a bit too short and her top was a bit too snug, but he kept quiet having made enough of a mess the day before. They went back to the same place they had eaten as 3 girls and this time there were no strange looks from either of the front end people. They were happy to have the same server, and he greeted them warmly.

"I see the seating arrangement has changed. Last time he was alone, this time it's you. Was there an argument over which dress to wear?" His broad smile let on that he was just joking, while letting them know he remembered them.

Becky looked up and smiled. "There was an argument, but not about dresses. I wanted him to wear his crotchless panties, but he insisted on a thong."

Bryan and Wendy looked at her, shocked, and what she had just said was beginning to sink in. Suddenly she was very apologetic, but the server stopped her and bent down. "I'm married, but it's flattering that you would want to try to excite me. I think you need to apologize to him much more than to me, though." He had never stopped smiling and went right on to take their drink orders before leaving the table.

She looked across the table. "Bryan, I'm so sorry. I don't know why I said that. I'm so embarrassed." She looked away, and looked back. "Please stop staring. It's unnerving."

"It's just, there was something for a moment. I could see it, but it's gone now. How about we talk about something nicer. Happier."

"I agree," added Wendy. "Let's talk about children and what pricks they can be, even when they grow up."

Now Bryan looked at her. "Where did THAT come from?"

She looked at him and tipped her head. "You know, that's a good question. Becky, then me. I think we're a little on edge about, you know, things."

He looked at Wendy, then at Becky. "I think you two need to calm down and focus on dinner before we just take turns embarrassing ourselves or each other. Oh, and Becky, you're on a two drink limit."

She wanted to protest, thought about it, then just said, "Yes sir, little brother." She quickly smiled and added, "I know, I'm just messing with you. Thank you."

Bryan turned back to Wendy. "I just realized, you know all about our disfunctional family, by one means or another, but I don't know about yours. Your FAMILY, I mean, it doesn't have to be disfunctional."

She smiled sweetly. "How nice of you to qualify it, but we have our issues. Dad works all the time, picking up extra shifts to pay for the vacation condo and his three quarter ton pickup that only ever moves a few boards. Mom screams at him for spending all his time messing around with cars or building things or whatever. She goes grocery shopping in shorts that leave her ass hanging out. Neither of them pay much attention to me. My older sister got married after the unexpected baby was born, but she didn't marry the father because he skipped town. My younger brother hangs out with dad in the garage and started drinking beer when he was 14."

He realized his mouth was open. "Seriously?" She pointed to Becky and he looked at her nodding.

Wendy continued, "I got this internship with a local politician because of a high school teacher who told me he saw potential and he wanted to keep me on a road where I might reach that potential."

Bryan had to ask. "And did he ask for anything in return for his help getting you a good position?"

Wendy looked down. "Yeah, the first good position was missionary. The second was face down, in that one really bad experience with anal. But after that he left me alone." She looked into his eyes and saw his mouth open. Her finger went to his lips. "Please, don't ask. It's more than you want to know. And, uh, more, than you want to know."

They were sipping their drinks, waiting for their food when Becky noticed a guy had come in and was talking to the hostess trying to seat him. He was pointing their direction and he looked familiar. The hostess stayed at the table and he walked over.

"Hi, sorry to interrupt, but I'm Cory and I saw you the other day, but I think you," he pointed toward Bryan, "were dressed a little differently. It looks like you have a fascinating relationship and I'm wondering if I can join you for dinner. I know it's unusual, but, I think, no, I'd really like to get to know you better."

Bryan looked around, seeing only confusion but no outright rejection. "Sure, but you need to sit on that side."

He waved at the hostess and she went back to her station. "I'm sorry, I don't quite understand the relationships here. Last time I saw you the women were seated together, but now it's ... different?"

"Hi, yes, I'm Becky. I'm his sister. Well, step-sister, but we're trying to get past that step thing."

"And I'm Wendy. I'm Bryan's financée, but he hasn't gotten up the nerve to ask so it isn't official yet."

Bryan looked at her, shocked, while she smiled back sweetly. Cory grinned. "Now there's a woman who seems to know what she wants. And that's kind of what I was hoping to find out."

Becky looked at him. "I'm sorry, you were hoping to find out?"

The server came with their food and took the order from the newest person at the table, interrupting their questions. "Are you on the same check or separate?" he asked.

Becky quickly said, "Same," while at the same time Cory said, "Separate." The server stood looking at them. Bryan settled it by saying, "The same check, thank you."

Cory smiled again as the server moved away. "I assure you, I can afford my own meal."

Bryan leaned forward. "Of course you can. You're paying the bill."

Becky raised her eyebrows, but Cory just smiled. "You're an interesting person, hiding fact and fiction in mysterious ways. I knew I'd be intrigued."

Bryan leaned forward again and spoke softly. "I saw the line of your bra strap as you sat down." He sat back as Cory's grin vanished. "I'm certainly not going to make judgements, but it is kind of interesting, isn't it? And how do you remember us so well?"

"I work PR for a larger company in the area. It's part of my job to remember people, and, you're right, I had a special reason to remember you. As I said very honestly, you have an interesting relationship."

Wendy sat back and whispered, "More interesting than you know." She and Becky exchanged glances.

Becky broke out of the shock first. "Wait a second. You saw us and hoped we'd come back because you want to find out how we go out in public with a guy in a dress? We just, I mean, we, us girls, decided he looked so good in a dress he needed to show it in public. He went along, it went fairly well, and that's it."

Bryan looked at Cory. "Are you wearing a thong or panties?"

Cory was grinning again. "You, Bryan, are very direct. It's panties. I find a thong isn't the best choice for going out for anything except a short trip. Such as to the grocery store."

"My sister thinks guys in thongs are hot." He was pushing it, and Becky's eyes showed a little anger.

Cory turned to look at Becky. "Do you really? That's really surprising. There was one girl who found, uh, ok, who I told, and she called me names that I'm not going to repeat right now."

Becky touched his arm. "I'm going to guess a lot of the words started with F."

Bryan added, "We've had a little experience with that sort of thing."

Cory looked at Becky and Wendy. "But you two are ok with this? I mean, with him dressing as a woman?"

Wendy smiled. "I like his description better, a man in a dress. It seems more natural that way, you know, just a choice of clothing." She paused a moment, then turned to Bryan. "Why are you being so aggressive with him?"

Now Bryan smiled. "To see how he handles it. To see how he answers. To see how much thought he's actually put into it. In the last couple of weeks, I've been where I never expected to be. I think that gives me the right to challenge somebody to see if they understand who they are and what they want."

Cory looked uncomfortable for the first time. "I would like to answer your questions as much as possible, but not here, please. These booths are hardly soundproof and I've already shared more details than I planned for the big wide world to know. Perhaps we can go to a park or somewhere a little less crowded?"

Bryan looked at Becky, eyebrows raised, and she shrugged. "Ok, Cory, let's settle the bill, then we can talk meeting place in the parking lot."