Jane Finds Herself
Copyright© 2025 by ghostwritten
Chapter 41
Fiction Sex Story: Chapter 41 - While trapped on a family camping trip, Jane has an unusual run-in with a man at the washrooms. Fighting her fears and anxieties, Jane continues to meet with him each night and even befriends his daughter Riley... who looks remarkably like her.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/ft ft/ft Fa/ft Consensual Heterosexual Incest Spanking Anal Sex Analingus Cream Pie Double Penetration First Facial Fisting Masturbation Oral Sex Petting Sex Toys Squirting Voyeurism Small Breasts
“YOU DID WHAT!? I CAN’T BELIEVE IT, WHAT IS HAPPENING WITH YOU?” Riley yelled through the phone. I’d told her about Tucker taking me to the truck stop and blowing those random guys. Unsurprisingly, she wasn’t exactly thrilled about it.
“Please stop shouting,” I begged, having to lower the volume on my earbuds. It really hurt my ears.
Riley tried to calm down. “A glory hole? Really? Jane, I’m not joking. I’m really worried about you. You seem to be on this self-destructive path, and I really want to help you. I’ll do anything you need; I can be there in a few hours for a rescue or vacation.”
“It’s fine, I’m ok,” I promised. “It was a one-time thing; I tried it and now I can say it’s done. Please don’t worry about me.”
“How can I not? I don’t understand what’s going on with you suddenly. This isn’t you.”
“What if it is me?” Finally saying what I’ve been thinking out loud. “What if this is all I’m good for; just some cheap bang that’s good for a few thrills and that’s it. As much as we’re alike, in some ways, I’m not like you. You’re the better me, you always have been.”
Riley sounded exasperated, “No, neither one of us is better than the other, Jane. That’s just in your head; I think that Tucker guy is making you feel like garbage so he can manipulate you.”
“But I was with Brian last night, he was so loving and gentle, and yet...” I tried to find the words. “ ... I felt empty. I feel alive when being told what to do, fucked like dog in heat, or made to suck cocks. I just ... I feel like nothing without it.”
“Jane, I love you. You know that. Lots of people love you. You’re just upset and covering it with the rush of sex, I get it. You’re worth the world to me and I can’t wait to live with you and get up to all kinds of shenanigans in the city. If you weren’t worth it, do you think I’d do that? Do you think that I’d end...” she stopped suddenly.
I picked up on it immediately, “ ... end what?” I asked.
“Nothing, it’s not the time.”
My concern was building, my own problems melted away. Something was clearly wrong and she wasn’t telling me about it. I asked again, “Riley, what ended?”
“I don’t ... I’m more worried about you. I’m fine.”
“Riley, what happened?” I wasn’t about to drop this.
I heard a sigh, she knew I wouldn’t stop asking, just like I knew Riley wouldn’t stop pestering me about my life. We really were two peas from the same pod.
“James and I broke up.”
I wasn’t shocked, she told me they’d been having problems, but it was still sad to hear. “What happened?”
“It- well, he didn’t want me to move. He wanted me to stay in town, maybe even...” she trailed off.
“ ... even what?”
“Even get married.” She paused, taking a breath. “He didn’t ask, if you’re wondering, but he said he’d been thinking about it. My talking about moving to the city with you derailed that. He gave me a choice.”
I clarified, “He gave you an ultimatum.”
“Yeah. Him and a future together ... or you. I chose you, Jane.” I heard her sniffle through the phone, I wished I could reach through and hold her. “I don’t ever want to hear you say you aren’t worth anything, Jane. Because you’re worth a lot, you’re worth the world to me.”
“Riley, I’m so sorry.” I started misting up. I never wanted to make Riley sad.
“Besides my parents, I’d choose you over anyone or anything.”
I felt the same way about her. I didn’t understand it; it seemed clear that Riley didn’t either. Ever since we met, I’ve just felt this connection with her, this magnetic pull. We’d only known each other a few months, but it felt like I’ve known her my whole life.
“It’s his loss, we could have had a threesome,” I said trying to cheer her up. I only got a light chuckle.
“How upset are you?”
Riley let out another sniffle, “A little. I thought that I wouldn’t, you know? I told myself this was never supposed to be a forever relationship, but now that it’s over, I feel sad about it.”
“Do your parents know?”
“Dad does,” said Riley while lightly crying. “He could tell something was wrong. We sat down and talked about it.”
“That’s good, I hope he was able to cheer you up a bit.”
“Not in the way I’d hoped, but the talk was nice.” Riley’s reply didn’t fill me with hope that the issues with her parents had gone away either.
“So you two still aren’t...?”
“No, I asked but he said he was busy,” she said, adding, “It was 1:00am, what work could he possibly be doing?”
I didn’t want to pry, but I was curious. “Does he do that a lot now? Things with your parents haven’t settled?”
“I don’t get it. He’s on his computer most of the night ‘researching’ he tells me. I ask for a quick one and he says he’s too tired,” she complained. “There’s something going on and they don’t want me to know about it.”
The change in topic seemed to have changed her mood from sad to frustrated. I felt bad that she was dealing with all this on her own. Plus, through all of it, she was worried about me at the same time.
“Have you found out anything new?”
“Beyond my Dad spending his night on his computer now? Not really,” she explained. “I did come home to Mom yelling at someone on the phone, but I don’t know if that was related.”
“Does she do that a lot?” I wondered aloud.
“Not usually, unless it’s an obvious scammer; but even then, this was nasty. She kept calling the person a fucking bitch and that she’d ruin her life.”
“Wow!” I couldn’t believe it. “Do you think your Dad’s been messing around behind your Mom’s back? ... besides with you, of course.”
She let out some air, “I don’t even know anymore. I wouldn’t have thought so before ... but then you ... and me, I guess. Maybe anything is possible. I just wish they’d come out and tell me.”
The sound of her frustration cut through the phone, I could certainly relate. For me, at least I knew now what my Dad’s issue was; when I didn’t, I felt lost in the dark. I was constantly wondering what I did wrong for even the smallest things.
“Have you tried asking your Dad directly?” I suggested. “I know I was afraid to ask my parents stuff, and now my Mom and me are ... oh...”
“What?” Riley was immediately concerned.
“I realized I hadn’t mentioned something that’s happened since we talked last time.”
“What? What is it? You aren’t going to a gangbang or anything are you? If you say yes, I’m kidnapping you tonight for your own protection.”
I couldn’t help but laugh, “No no ... nothing like that. Remember how my Mom took care of me after Brad’s?”
“Yeeeah?” There was uncertainty in Riley’s voice.
“Well, as I said, we talked and I told her everything. Then she told me a bunch of stuff too. Surprisingly, she was ok about Brad, but she wanted the three of us to talk ... that happened the other night.”
“OK, how’d it go? Did she really give it to him?”
“Weeelll, I think they kinda came together on a few things. They sort of banged things out.” I had a hard time not laughing.
Riley was clearly confused, “What the hell are you talking about?”
“Alright, so Mom wasn’t too happy about finding me so bruised and, you know, wrecked from being kept up all night by two men. She wanted proof he knew what he was doing with me...”
“Oh My GOD, you had sex in front of your Mom?” Riley guessed wrong.
“Not quite, kind of the opposite. I sort of ... watched her ... fuck Brad.”
“You didn’t!” she was laughing, it seemed to brighten her mood. “That’s so weird! Tell me that wasn’t weird!”
“It was, at first, but it was also kind of interesting...” I admitted.
“What? How?”
“Don’t get judgy, it isn’t too different from what you do with Curtis. Besides, you know my Mom had a bit of a wild college phase. There are things to be learned from a woman with that much experience.”
Riley laughed harder, it was good to hear. “You’re such a freak!”
“Nah, I don’t think a freak would suck Brad’s dick clean after they finished.”
“HAHAHAHA!” she laughed, I think I heard her sniffling, but from laughing so hard. “That’s so gross. You didn’t actually ... like ... clean your mom too?”
“No, but I might next time. She wants to go again, and Brad wondered if I’d join in. I said I’d think about it.”
“And your Mom?”
“She wasn’t so sure, but I think she wants to.”
Riley laughed again, “Our families are so fuckin’ weird.”
“They are, but we love them anyway.”
We talked for a while longer, both our moods seemed improved just from talking things out. Even if I knew she’d get mad at me, I would tell Riley anything and everything. We seemed to be able to pull each other up and make each other laugh. Moving in together couldn’t come quickly enough.
I just finished a brisk run Monday morning, when I returned home to an empty apartment. Mom and Dad had left for work again which left me free to do whatever I wanted. I didn’t work again till Wednesday, my official training period having ended, so there wasn’t much going on with that front. It was weird, I’d been so busy with life lately, that now I actually had a few days of nothing ahead; I didn’t know what to do with myself.
The hot shower felt nice, soothing my tired and sore muscles. I dried off and walked naked to my room. When Riley and I move in together, I wonder how much money we could save on laundry if we just walked around naked all day. It was a weird and funny thought, something that made me chuckle to myself. That silly thought did remind me of something though, I needed to call Brad about a financial plan to help make my living goals a reality.
We were supposed to chat about it a little while ago. I’d planned to get a few details one night when I went over. It just happened that was the night Tucker was there with his video equipment. I sort of got distracted by the lights, cameras, and double penetration. I figured I should do this more professionally and book an appointment at his office.
I dug around my desk trying to find it. It took a bit, I’d hidden it in a drawer, but I found Brad’s business card. He’d given it to me a while ago, the day before I met Tucker for the first time. It felt like years ago now but it was only over a month. How young and naïve I was then. What would Jane of the past say if she saw me now? The girl who sucks off strangers in a bathroom or enjoys having guys in her ass and pussy at the same time. Would she be disgusted with how she turns out, or proud that she’s expanded her horizons? I honestly didn’t know.
I flipped over the card, on the back were the instructions for that first night.
Tomorrow night
11:00pm sharp
Wear uniform
Get some sleep, you’ll need it
I didn’t know what kind of rabbit hole that one night would send me down. I still couldn’t decide if meeting Tucker was the worst or best thing that has happened to me. Because of him, I’ve done things I never would have even dared to consider. I feel freer and more comfortable with my sexuality. I’m not scared worrying about what people think of me ... with a few exceptions like my Dad finding out about Brad. That’s just safer for all concerned.
At the same time though, I can’t help but feel him digging his fingernails into me. The slow corruption that he’s done to me slowly pulls me down into the depths of a dark spiral. I don’t feel worthy of love anymore, I feel cheap like a poorly made dish rag ready to break apart at the seams. Only I don’t clean up dirt, I’m just a cum rag used to satisfy his disgusting intentions. No one else has made me feel as cheap and whorish as David Tucker. No one’s thrown money in my face to pay for my ‘services’. If I’d let him, he’d have paid me for the truck stop visit. It was this moral decay that worried me most.
While I didn’t care what people thought of the things I do, I also didn’t want to lose people either. I believe Riley to be a true friend who I can always tell the truth to. Yet even she is worried about the corrupting effects Tucker’s having on me. My other friends, Val and Becca, know most of my indiscretions but I can feel their harsher judgement. They don’t even know about the glory hole thing or my Mom. They couldn’t handle that last part. I progressed from a shy prude to an amusing whore in a very short time with them. I love both of them, but I wondered if we were growing too far apart. I guess I’d find out when Val sets a date for that threesome with her boyfriend.
I flipped the business card back over, my tangential thoughts having concluded. I grabbed my phone and dialed the number listed and waited.
A female voice answered, “Apple Bank, Brad Sheen’s Office, this is Lynn. How may I direct your call?”
I was thrown off at first, expecting to hear Brad on the other end. “I-uh, hi. I’m looking to make an appointment with Bra- I mean, Mr. Sheen.”
“Are you a current client with Apple Bank?” she asked, her voice a little nasally.
“Uh yes, I believe I have some investments made already with Mr. Sheen.”
“Name and account number?”
“Jane Landry. I don’t know my account number, it was set up for me.” Brad had set up my investment account on his own. It was separate from my normal bank account that my parents made for me when I was little.
“Ugh,” she grumbled into the phone. “I can make you an appointment, but you’ll need your account number during your meeting. Understand?”
She sounded rather unpleasant. I didn’t like being treated like a child; I was tempted to tell her to check with Brad, since he set it up in the first place. That I ride his dick on the regular and he’s banged my Mom too. I was certain that would knock the snottiness out of her, but it might upset Brad, so I bit my tongue.
“I understand,” I grumbled back.
“Fine. I can slot you in three weeks from next Friday, how’s 2:00pm or 2:30pm sound?”
“Are there no other openings sooner?” I was a bit frustrated, it might be better to visit him at night rather than deal with this nonsense. Of course I got back a snooty response too.
“Ms. Landry, Brad Sheen is very busy and his time is extremely valuable. Short of you getting here in the next hour; those are his next available times for ... baby investors.”
I was ready to scream at her but picked up on one key sentence. “What if I get there in an hour? Is he free?”
“Yes. He had a corporate client reschedule. He’s free until 12:00, then he has a lunch meeting.”
I looked at the time, it was just after 10:00. While I’d never been to or seen his office before, I knew roughly where it was. I could make it, I’d just have to be fast about it.
“Alright, I’ll be there shortly.” I said abruptly into the phone.
“I’ll keep it free but I won’t schedule you either. I doubt I’ll see you.”
With that, she hung up. I was angry but didn’t have the time to scream about it. I needed to get dressed and make my way to his office fast. I slipped on a lacy white bra and matching panties first. Checking my closet, I grabbed a white blouse and a blue knee-length pencil skirt. I looked professional enough, adding some matching blue heels and then tied my hair back. Grabbing my purse and keys, I raced out the door to catch the 71 downtown.
Brad’s bank was in the heart of the financial district, a tall seventy-plus story building rising into the sky. I got lucky with transit and found myself standing beneath this massive structure. While I’d been down to that end of the city before, I’ve never actually been inside one of these massive glass and steel towers.
The lobby atrium was bustling with people shuffling about. Most were talking on phones, briefcases in hand, as they headed in various directions. They all seemed to walk perfectly straight despite all the chaos, like it was a perfectly choreographed cacophony. I tried walking through but kept getting bumped around like I was out of sync with inaudible music.
After a struggle, I made my way to the elevator banks. I had to recheck Brad’s card for the floor, 61st and then find the corresponding elevator. They seemed to only go to set floors, with Brad’s serving floors 50 to 70. I crushed in with a group of 10 people. I hadn’t felt that tightly squeezed since Tucker and Brad took me together, and this was far less fun. Although I do think someone touched my ass.
I stepped off the elevator on the 61st floor, wondering if I’d just increased by body count. I was met with a large reception desk and an ashen-haired lady wearing a headset. Was this the rude woman from the phone? She smiled as I approached, reducing my suspicion.
“Hello, what can I do for you?” she asked politely, her voice was rather sultry.
“Yes, hello. My name’s Jane Landry, I’m supposed to have an appointment with Mr. Sheen.” I replied as professionally as I could.
“Give me a second.” I heard her keyboard clacking incredibly fast, before she turned back to me. “I’m sorry, I don’t have an appointment for you it seems.”
I struggled to control myself, “Yes. I spoke with someone a short time ago, she said he had a cancellation. A ... corporate client I believe.”
The woman rolled her eyes. I was about to get upset when she smiled at me. “Sorry, that wasn’t aimed at you. Lynn, Mr. Sheen’s assistant, has a habit of not filing changes to his schedule. I’ll call her desk to verify.”
I waited, amused by the fact that his assistant wasn’t liked by others too. It did make me curious why Brad kept her around. She must be good for something and I knew Brad, so my thoughts went someplace dirty. I could only hear one side of the conversation.
“Hello Lynn, this Pam at reception. Does Brad have a client scheduled? ... Well she’s here now ... Jane Landry. Yes, please make a note of it ... Thank you.”
She looked at me again. “Lynn will be coming to escort you in. Please just fill in this sign-in sheet. I apologize for the confusion.” She handed me a clipboard with a pen then gave me a little wink.
I wrote my name, the time, and the person I was visiting. There was a spot for ‘Company Name’, I thought about writing something semi-clever like Jaley Inc., Jane and Riley Incorporated, but talked myself out of it. I handed back the clipboard and the lady checked and thanked me.
A minute later, a tall chestnut-haired woman walked in, a scowl on her face. I immediately knew this was Brad’s assistant.
“So, you actually made it.” She said snarkily, her arms folded over her moderate chest.
“I did.” I fired right back at her.
“Very well, follow me.” The tall woman pointed into the office and started walking, her two-inch heels clicked loudly as she walked.
I made sure to thank the receptionist before leaving, then swiftly followed the assistant. She walked fast in heels, which was the only good thing I could say about her. She reminded me of a darker-haired Jeanette but with the social skills of a moldy cheese sandwich.
She brought me to a pair of large wooden double-doors. The windows were dark, so I couldn’t see in. She sat a desk in front, papers strewn everywhere and a couple of empty coffee cups teetering over the abyss.
“Do you have your... Account. Information?” she spoke slowly, hitting the last two words individually. Did she think I was a moron? I know that’s how I felt about her.
I didn’t feel like taking her shit. “He knows it,” I said sharply.
“Huh! Doubtful,” she said smugly. “Mr. Sheen’s one of the top financiers in the State. His portfolio has some of the biggest funds in the country. He only deals with you people as a courtesy, like charity. Unless you’re one of his other interests ... I’ll happily call security to take out the garbage.”
I just smiled at her. “You’d make a great salesperson.” I said sarcastically, before adding. “Why don’t we see who’s right and who’s wrong? Is he available now?”
She picked up her phone, once she pulled it out from under a stack of coffee stained papers and pressed a button. I couldn’t help but try to listen in.
“Hi Brad, there’s some blonde girl here to see you ... I don’t remember her name, Janet something ... Anyway, she doesn’t have her account information... so what? ... ugh, fine.”
She hung up the phone. “He’ll see you now. Follow me.”
She walked to one of the doors and pushed open the door. She stepped in first, blocking my entrance. I wanted to shove her out of the way.
“Brad, this is ... Janet somethingotother.”
I shoved my way past her and saw Brad behind a large solid-looking wooden desk. He stood up immediately when he saw me. His face was a mixture of surprise and delight.
“Jane! What a pleasant surprise, what are you doing here?” he asked.
“I thought we could go over my Financials and investments, like we talked about.” I said while giving a nasty side-eye to Lynn.
“Mr. Sheen,” Lynn said, not accepting defeat. “Shall I contact waste disposal about your trash problem?”
Brad glared at her, “You can go now, Lynn.”
As she walked by to leave, I couldn’t help but needle in my victory. “Close the door on your way out, won’t you toots?”
I heard her grumbling, and nearly slammed the door on her way out. I was proud of me for standing up for myself, I know it was something I wouldn’t have done a few months ago. I guess there was some good that came from my recent changes.
“Wow, what an office!” With the evil assistant defeated, I was able to look around Brad’s fancy corner office. Natural light poured in from the south-facing windows which brightened up the wood trim. In front of his desk were two plush leather chairs. He invited me to sit.
“Sorry about Lynn,” Brad said. “She’s kind of a terrible assistant, but she’s a great guard dog.”
I didn’t understand, “Are you two...?”
He shook his head. “No, God no!” He laughed. “When you’re me, people always want five minutes, it’s always ‘just five minutes’. It’s never five minutes. Lynn’s good at keeping those people at bay.” He paused, “Plus, it’s not the 50s anymore. We can’t get away with that stuff.”
I looked at him, knowing his bullshit. “She scares you, doesn’t she?”
“Terrifies me, is more like it,” he laughed. “If she wasn’t too old for him, I’d set her up with Tucker.” We both had a good laugh.
“So, what does bring you by, Jane?” he asked leaning over his desk. I caught him checking out my legs, so I uncrossed and recrossed them just for fun.
“Honestly, I’m here to see you in a professional manner,” I was trying to sound smart. “We were supposed to talk about my finances and savings, but we always get sidetracked.”
He leaned back in his chair, “Hmm, that’s true. We were supposed to do that, I forgot.”
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