Know Thyself Ch. 07

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Ashley must make a decision & an unexpected visitor shows up.
14.9k words
4.79
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Part 7 of the 9 part series

Updated 06/07/2023
Created 01/11/2016
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It's cold. Brisk, as my mom put it this morning. Fall is in the air and just like that, New York put on their coats. At least, it's cold to me. I never know how to dress anymore. I don't have an extra layer of fat like I did when I was Ben, so I've noticed I get colder much quicker now. The last couple of days have been all sweaters and jackets. Central Park is changing colors now that the trees have been informed it's fall. Everything's changing, except me of course.

It's been a couple of days since I got back from Boston. I haven't spoken to anyone since that awful weekend. Alana didn't show up to class, Matt hasn't reached out to me, and I've heard nothing from Wendy. The only person who has been trying to reach me is Charles. We texted a little on the train and even made plans to meet in public. He wouldn't stop texting me unless I made plans with him. We're meeting at a Starbucks on Friday afternoon. The one on Thirty-Eighth and Eighth has a second floor where you can sit down and talk with people, unlike all the other ones in the city that are cramped. It's public, it's non-committal, it's no big deal.

That's what I keep telling myself.

And it's true. I haven't committed to anything, just some coffee.

For the life of me I don't know why I even agreed to that.

He's been texting me since then, stupid one liners and things like that. I haven't responded to any of them mainly because I don't want to encourage it. I shouldn't have even texted him that first time. Call it a moment of vulnerability.

There wasn't much talk when I got home about the weekend. My parents asked me all the basic stuff. "How's Wendy?" "How's Boston?" "Any problems with the train?" I'm glad I didn't have to elaborate with them on anything. I wonder how open the old Ashley was with her parents about her personal life? It's one of those mysteries I'll never be able to figure out. I can't ask my mom and dad "hey, how personal was I with you my whole life?" It seems like she never shared that much with them just by the way we talk. Who knows? Lately everything's a mystery to me.

It's late Thursday night and I'm sitting in my room when I hear the door open behind me. Jack pops his head in.

"What's up Ash?" He's trying to sound casual but I can tell something's on his mind.

"Not much. What's up with you?"

He walks in and closes the door, then takes a seat at my desk and puts his feet up.

"Nuthin'. How was Boston?"

"Mom didn't give you the rundown?" I can't help but sound exasperated. I really am tired of talking about it.

"She told me as much as you told her. 'It was fine.'" He does a spot on impression of our mom and I can't help but laugh.

"It didn't go well at all," I tell him.

"What happened?"

As I lay on my bed, I look away for a moment to see how I can word this. I bet I can tell Jack the truth, but for some reason I don't want to.

"Me and Wendy got into a fight," I say.

He raises his eyebrows. "About what?"

I shake my head. "Just stuff."

He looks at me for a moment trying to figure me out. "This is the time when people start to change."

"It's not like that. It's just...I don't know." I let that hang in the air for a moment but cut in before he can continue his questioning. "Hey, how's the new job going?"

"Great!" His whole face brightens up. I realize this is the first time I've asked him about it. "The work is awesome. Who knew I'd be interested in legal stuff?" He laughs a little at that. "Plus Greg is the man."

It's weird to hear him bring up my old dad, Ben's dad. Not to mention he wasn't really "the man" when I knew him.

"Why is he the man?" I ask.

He shrugs. "I don't know, he just is. He doesn't get all worked up over the smallest thing. He's given me time to settle in, which is good because I have no idea what everyone's talking about half the time. He gave me a couple books to read."

"And are you reading them?"

He gives me the kind of lame look reserved only for siblings. "Yes I'm reading them. It's interesting."

"He never gave me a book to read," I say half under my breath and then catch myself. I look at Jack.

He's giving me a funny look. "Why would he?"

I shake my head. "I don't know, he just didn't."

He looks at me strange but decides to let it go. We sit there for a moment, me on my bed and him at my desk. He's rocking backwards on my chair.

"What happened to the Taylor Swift poster?" He nods to the empty spot on my wall across from my bed.

"I hate Taylor Swift," I say as I roll my eyes.

He smirks. "See, like I told you. This is the time when people start to change."

"Can I ask you something personal, Jack?"

He nods.

"Have you ever slept with someone who was married?"

He tilts his head back and puffs his cheeks. "No, not a married woman. I've slept with a girl who had a boyfriend, but never married."

"Would you?"

He tilts his head from side to side like he's weighing the options. "Probably. I'm not the one who's married. It's her choice."

"What about someone who was a lot older than you?"

"Like how much?"

"A lot."

"You sleeping with an old married guy, Ash?"

"No!" I sound a little too defensive and he looks at me even more suspiciously. "Really, I'm not."

"But you want to."

"I don't know...Not really...No."

"Then don't. If you don't want to sleep with someone, don't sleep with them."

I nod, not looking at him.

"Hey," he calls out to me and I look up at him. "For real. Don't let someone pressure you into sleeping with them."

"No one's pressuring me."

He puts the chair back on four legs and leans forward. "Does this have anything to do with Boston?"

I shake my head. "No, just life."

"I used to say stuff like that before rehab."

Rehab? God, there's still so much I don't know about my new life.

I look at him puzzled and he picks up on it. "You remember me back then. You're not like, hanging out with some old dude who's making you do stuff, are you?"

"No! Jack, for real, no."

"Okay, well..." He gets quiet for a moment. "Just be honest with me here. Is everything okay?"

I don't want to lie to him. Everything is definitely not okay, but there's no way to tell him. Well, there is one thing I can tell him.

"I was seeing this guy. A guy my age. But then, I started seeing this girl."

I pause and look at him to see what his reaction is. He leans back in his chair.

"I told the guy what I was doing and he got mad and broke up with me. I told the girl I had a boyfriend when I started seeing her and she got mad and broke up with me. I thought being honest was the right thing to do but I lost both of them."

"So fuck 'em."

His bluntness takes me off guard. I blink at him. "What?"

"You did the right thing, you were honest. If they're going to judge you for being honest, they didn't like you to begin with. So fuck 'em."

A big smile crosses my face. This is the first time I thought of it like that. I nod.

"Yeah," I say. "Fuck 'em."

We both smile at each other.

"So," he begins. "That's why you never give me any of your friends' phone numbers. You're keeping them for yourself."

I throw a pillow at him.

"So you're into girls now?" He asks.

I nod. "Yeah, I think so."

"Cool."

I'm very tense and I think he's trying to find something to say, but of course he looks like the same care-free Jack. I had no idea I was going to "come out" today but here I am.

I wish Wendy was here to see it.

I try to look relaxed but I keep looking up at him. After the second time I catch his eye and look away he smiles as he leans back on two chair legs.

"It's not a big deal you know," he says.

"Yeah I know," I answer, eyes still looking down.

"For real. My little sis is into girls." He shrugs. "So what? A lot of people are. You're the same old Ash."

"Not really," I blurt out. He has no idea how much that's not true.

"You are to me. I kicked the needle for you. You think anything is going to change because you're a lesbian? Fuck Ash, you know better than that."

I look up at him and I'm about to cry. I've always wanted an older brother and here I've lucked out and taken over the body of someone who has the best older brother someone could ask for.

He kicked the needle for me? I wish I knew the full story of what that means. I feel like I'm betraying him by not knowing.

"You're not going to cry, are you?" He asks with a smirk.

"Fuck you, no I'm not!" I say as I wipe a tear from my eye.

He chuckles.

I throw another pillow at him and he catches it this time. "Don't laugh at me!"

"You're such a crybaby," he says.

"You're a crybaby!"

"Nice comeback," he mocks.

I get off the bed and walk to him. I lean down and wrap my arms around his shoulders and kiss the top of his head.

"I love you, Jack."

He squeezes my arm. "I love you too, sis."

I let go and sit back down on the bed.

"Have you told mom and dad yet?" He asks.

I shake my head. "I didn't even know I was going to tell you."

"We both know you can't keep anything from me for very long."

"I guess not," I say. I'll take his word for it.

"You should tell them. Especially mom. She'll be hurt if she thinks you can't trust her.

I nod. I know he's right. I should tell them but I don't know how. It does feel good to have told someone though. I know I shouldn't feel so uncomfortable. I've been a man for thirty years, so telling people I'm attracted to girls shouldn't feel awkward. It's just that I've really come to see myself as a woman now. I am a woman, physically and mentally. I look in the mirror and I see a girl staring back at me. I feel the things a woman feels, I see the world as a woman and the world responds to me in kind. So how can I not see myself as one? Telling Jack I'm attracted to women feels as if I was Ben telling someone I'm attracted to men. I don't fully understand it but that's how it is. So it's a big thing to admit and it feels good to have told someone.

Jack stands up and stretches. "Alright sis, I'm off to bed. Long day of lawyering tomorrow."

"Please! You're not a lawyer," I tease.

"I know. I just play one at work." He turns to go but stops at the door. He gives me a kind-of serious look. As serious as Jack can give. "Tell mom."

I nod and he leaves. It's a weird feeling but I never even thought of telling her. As much as I've gotten used to my new life, it's still hard to think of the two adults who live here as my parents. Some relationships are hard to break. As much I try to refer to Greg as "Greg", I still find myself thinking of him as dad.

*************

When I wake up in the morning, something feels different. Like a weight has been lifted off me. As odd as it sounds, I feel more free. It's a weird thought to have because ever since I became Ashley I felt as though I wasn't bound to anything anymore. Ever since I made the realization that I'm a lesbian, it feels as though I've been holding something back.

I dreamt of Wendy last night. I saw us together, happy, and in love. As my eyes open I don't want the dream to stop. I keep them closed and try to trick myself into thinking I'm still asleep, so my subconscious can continue this beautiful life it has shown me.

Maybe my subconscious needs some motivation?

With the image of Wendy in my head, I start to run my fingers up and down my body. The sharpness of my fingernails running softly over my skin gives me a shiver and I lick my lips. My hand gets to the curve of my breast and I follow it's rise up to my nipple just as I imagine Wendy whispering to me.

"I love you," I see her say.

With two fingers I pinch my nipple as my legs spread apart. My other hand goes for my pussy and I imagine Wendy's arms wrapped around me, caressing me.

"Wendy," I whisper back aloud.

My stomach starts to tighten and contract from the waves of pleasure pulsing through my body. I can feel the wetness start to dampen my panties as my hand continues to rub my clit. I squirm in bed, helpless against this uncontrolled lust for my friend. I slide my panties off and suddenly I can smell the passion exuding from my pussy.

I swear, masturbating as a woman feels so much better than it ever did as a man.

Now the hand caressing my nipple goes for my pussy as well. I stick two fingers lightly inside me as my other hand quickens it's back and forth pace over my clit. I want her so bad and I would give anything to have her right now. I imagine what her pussy looks like behind my tightly closed eyes and suddenly I want to taste it. I need to taste it. I take the two fingers that were inside me and I put them in my mouth, tasting the wet pleasure that exuded from me.

Oh Wendy, you taste delicious, just like I thought you would.

"I love you," I see her say again in my mind and suddenly I feel that familiar eruption start to build. The sweet fingers that were just in my mouth go to my nipples and I flick them back forth with passion since my other hand is working too fast on my clit for anything else to be down there.

"Ohhh!" I can't help but let out a moan as my orgasm builds even stronger. I just want to open myself up and give myself over to her. Offer her my body in exchange for her warm love. Nothing has felt so good before.

And then the warm liquid starts to go and my hand stops it's furious motion against my clit and holds my pussy tightly. The orgasm is the strongest one I've felt so far. My other hand cups and tightens around my breast as if it might escape my body from the sharp spasms I begin to have. My legs tighten around the hand holding my pussy and I roll onto my side as I continue to jerk back and forth in ecstasy. I'm panting, almost out of breath and I let out audible sounds of pleasure that I can't hold back.

I open my legs to give my hand some air. It's soaked! Soaked with juices brought on by the thought of Wendy. I lick my fingers again, pretending they were just inside of her. I sit up and inspect the damage. There's a giant wet spot in the middle of my sheets. I'll have to cover it with the blanket and hope my mom isn't doing laundry the minute I leave.

That's the first time I've masturbated and not thought about a man. I still don't know what it's like to have a cock inside me. Maybe I should explore my body a little further. I am eighteen, I can buy a dildo. Why not?

You are meeting a man today.

The thought of Charles gives me a shiver and suddenly the liquid I exploded onto my inner thighs feels cold. I'm meeting him today in between my Psychology and Poly Sci class. The reason we're meeting in the middle of the day is so that he doesn't have to explain to his wife why he's going out at night. The idea that this is wrong shouldn't give me a rush but it does. I hate that it does but it does.

It's just coffee. If I want to leave, I have a legitimate excuse that I have class.

It's just coffee, right?

*************

Poly Sci wasn't particularly interesting today. Okay, I'll just come out and say it. It was boring! I normally enjoy the class but today's lecture just didn't catch my attention. To be fair, I wasn't listening that closely anyway. My mind was on the meeting with Charles. As I collect my things, I'm still in my bubble and don't hear the boy next to me asking me something.

"What do you say?" He asks, finishing off whatever it was he just said. We've been "class friends" so far this semester but haven't done anything outside of Poly Sci. His name is Derick and he's kind of a hipster.

No one is "kind of" a hipster. He's a full fledged Brooklynite.

"Sorry, what?" I ask him, sounding a little flustered.

"Just wanted to know if you wanted to get lunch?" He asks me, his nervousness apparent. He's wearing one of those shoulder bags that holds a laptop. The grey strap crossing diagonally down his chest is being rung by both of his nervous hands. He probably doesn't even realize he's doing it.

"I'm sorry, but I have a meeting with someone. Maybe next time?" I try to sound as apologetic as I can without giving too many details. It is a "meeting", I'm not lying.

He nods in defeat, his eyes darting to the ground. "Yeah, sure. Next time."

He lingers for a moment as I finish getting my stuff together. I should be more inviting, I normally am, but my mind is elsewhere.

"Well, have a good weekend," he says as he turns to go.

"You too," I call out to him as we walks away.

All the students file out of the classroom and I make my way onto the street. The Starbucks I'm meeting Charles at is on the west side, so once again I have to travel across the island. I get on the Six train and get off at Thirty-third street. There weren't that many people on the train, which I found relieving. After the incident on the street last week I've been a little nervous walking by myself. I know I shouldn't, it was a one-time fluke. I just ran into the wrong people at the wrong time, but I can't help this feeling of uneasiness. Who else should I not run into at the wrong time?

The crosstown bus approaches the stop to take me across the island. This one is packed, as I figured. The crosstown busses always are. I don't find a seat on this one and am forced to stand the whole way. Eventually I get to Eighth Avenue and get off the bus. The Starbucks is only a block or so away, so it's a short walk before I get there. I walk in and look around. The first floor is just the ordering counter with some ledges along the window for people to stand at. The seating is upstairs and you can't see anyone from down here. Maybe a couple people sitting on the single chairs by the bannister, but he wouldn't be sitting there.

Should I just go upstairs and see if he's there or should I get a coffee?

I don't want him to pay for anything, this way he won't feel like I owe him something. Plus, if I have a coffee in hand it'll feel more casual. The line is actually pretty short. Normally I'd order something fancy but I don't want to spend that much money and I want to be able to throw it out and leave quickly if I have to. I just order a tall pike. (That's a "small" for all you non-Starbucks people out there). After I mix it with some milk and sugar, I make my way upstairs. I see him immediately. He's sitting to the right in a corner where there aren't a lot of people. The minute he sees me he smiles and waves. He doesn't look as much like a suburban dad this time. He's wearing a button-down and a tie with black slacks. Much more formal than what I saw him in at the fountain way back when. When I get to the table he stands up.

"Nice to see you again," he says.

I give him a half smile and sit down. After I sit, he does as well.

He points to my cup. "You didn't have to do that. I would've gotten you a drink."

"It's okay. It's just a coffee." I try to sound casual.

"So how have you been?" He takes a sip from his cup, his eyes on me the whole time. I forgot how inviting his eyes are.

"Not bad. I started school. It's going well."

"Congratulations," he says as he tips his cup to me.

"How are things with you?" I ask.

"Fine. Depends on the day."

"Why is that?"

"When you're a day trader, your mood changes with the market." He gives me a half smirk.

I forgot he was a day trader.

"Aren't you missing out on a lot of money by meeting in the middle of the day?" My attempt at teasing.

"Well, some things take priority."

I look down at his hand and see his wedding ring. At least he didn't take it off. He knows I know he's married, no sense in being a total cliche. He sees me looking at it and covers it with his other hand.

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