Know Thyself Ch. 08

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"You could always get married before. It's just the piece of paper you wouldn't get."

"I know that now. But when you're a kid and you're told marrying a girl is illegal, you think you can't do it. I always assumed I couldn't do it. So now I want to be open about it but I just don't know how."

I had no idea Wendy felt like this. She wants to get married? This can't be something specific to this life. The Wendy in Ashley's life has to feel the same way.

"You think I'm crazy, don't you?" She asks me.

"No, I really don't. It makes perfect sense to me. I spent my whole life trying to be as masculine as possible. The whole time I was so unhappy but I never knew why. It's only recently I finally accepted the fact that I'm a woman.

I feel her grab my hand and we look into each other's eyes for a moment.

"I feel like..." She begins but trails off. She shakes her head. "I don't know what it is. Not that I know you, but I feel like I know you...You know?"

I smile and nod. "I know exactly what you mean. I feel the same way."

We both slowly lean in and kiss each other. The taste of her kiss is the same beautiful taste I knew as Ashley. My free arm wraps lightly around her back and I hold her close. She smiles at me.

"That's the first time I've ever kissed a woman," she says.

"That's the first time someone has called me a woman," I say.

We both laugh and kiss again. From the corner of my eye I see a flash go off. The light breaks off our kiss and we both look in the direction it came. Standing a few feet away from us is the bar photographer. He smiles and nods and continues flashing pictures of the crowd.

I decide to to take a leap. "Do you want to get out of here?" I ask her.

She nods. "Yeah. Where do you live?"

"Bay Ridge."

"Whoa," she says with mock shock. "I'm a few blocks away. Want to come to my place?"

I nod. We both finish our drinks and head out. I try to pretend like I don't know where I'm going even though I know the route very well. This is where I was last night when I was still Ashley. We get to her place and she keeps her voice down as she enters the apartment.

"Sorry, I forgot to tell you I live with my parents," she says.

"That's okay. So do I."

We quietly tip toe to her bedroom and she closes the door behind me. She takes her heels off and I decide to do the same. Then we embrace in the middle of the room and kiss more passionately. Her body feels so much smaller in my arms than I remember. I'm a clear three inches taller than her, maybe more. I try to stay as gentile as possible because I know how she likes to be touched. I break the kiss and run my tongue along her neck, immediately finding her spot since I know where it is. She gasps and her hands clench around the back of my neck.

"Yes," she breathes out.

I can feel my cock start to grow but now the idea of my dress tenting isn't so bad. I lay her down on the bed and take her blouse off, revealing a purple bra underneath. I kiss her neckline as I undo the bra, revealing her perfect breasts. The breasts I know so well under different hands. I caress her body as I flick her nipples back and forth with my tongue. She squirms under my body.

"Oh Ashley," she whispers out. Hearing her use that name drives me crazy and I can't help but squeeze her breasts and suck tightly on her rock hard nipple.

I move lower, kissing her flat stomach and feeling her muscles spasm. Her brown skin is just as beautiful as it is in my other life. I remove her skirt and panties and reveal her dripping wet pussy. She even smells the same as she does before. The same smell that drives me wild. I bury my face between her legs and run my tongue up until I find her clit. Her hands find the back of my head and he grabs a fistful of my wig as my tongue massages the pleasure out of her. Her shaved pussy twitches with every flick of my tongue, as if I have her body on a string and my tongue is the puppet master.

She lifts my head up and gives me a long and hard kiss, which I know is so that she can taste the juices of her pussy on my tongue.

"I want to see you," she says.

I turn around so she can unzip the back of my dress. I turn back around and let it fall to the ground, revealing my bra and panties. I'm about to undo the bra when I suddenly become self conscious.

"What is it?" She asks.

"My bra. I...I don't want you to laugh but..." I take out one of the tissues and hold it up.

She reaches out and pulls me close and kisses me on my smooth stomach.

"I would never laugh at you," she says, looking up at me.

I undo my bra and guide it to the floor, making sure the tissues stay in the cups. I slowly slide my panties down and my rock hard cock pops out, straight as a board. She looks at it for a moment.

"I've never been with a man before," she says, but then catches herself. "I mean! I've never-"

I cut her off. "It's okay," I say with a smile. "I know what you mean. It's okay."

She reaches out and wraps her hand around my cock. She slowly leans down and opens her mouth just enough to let the tip in. I feel her tongue run in circles around my tip as her hand begins a slow jerking motion up down my shaft. She sticks her tongue out and runs it up and down the bottom side of my cock. I can tell she's nervous and she's never done this before. She stops and looks at it a moment and I don't say anything, letting her find her comfort. Then she opens her mouth and takes me in, swallowing my cock halfway. She puts her hands on my thighs and begins jerking my cock with her mouth, going back and forth.

I lose myself for a moment and put my hands on my chest, half expecting to feel my breasts, forgetting I don't have any. Still, I hold my hands there, massaging my nipples as her warm mouth wraps around my cock.

"Oh Wendy, yes," I breath out in pleasure.

She goes to my balls and starts licking the bottom of my sack. I see her beautiful eyes stare up at me, half her face covered by the length of my cock.

I reach down and guide her up, laying her down on the bed.

"I've never done this before," she says.

"I know. I'll go slow."

As I lay on top of her, I grab my cock and feel for her hole. It's soaked, ready for my cock to enter. I slowly slide the tip in and I feel her jolt.

"Are you okay?" I ask her.

She nods.

I slide it in a little more and slide it back out. We kiss again, and as our tongues dance together I slide my cock back inside of her. I slowly thrust in and out, making sure not to hurt her. With each thrust into her, my pace quickens.

"Oh God, you feel so good," she says to me. "I want you so bad Ashley."

"I want you too Wendy."

Not able to hold back anymore, I start to thrust in and out of her at a steady rhythm. Our bodies smack off each other and I see her bouncing back and forth underneath me. I can feel the juices falling out of her, the warm and moist feeling surrounding my cock. I know exactly how she feels, the euphoria of the warm liquid being mined out of your pussy. I've been on both sides (granted from her end I only experienced a dildo) but still, the thought of it drives me wild and I start to go faster. Her eyes widen and I pin her hands above her head as my hips pump our bodies together. She bounces off me like a rag doll and I can see the pleasure in her eyes. We're both breathing heavier and heavier with each thrust of our bodies and I start to feel my cock fill with my own juices.

"Wendy," I call out, this time in full voice.

"I'm going to cum," she cries out just before her whole body spams and tightens. The rhythm of my fucking is broken only momentarily and once her muscles loosen, I continue the hard thrusting of my cock inside of her. It's only a few more seconds before I pull out and instinctively bring my cock to her mouth and thrust myself inside of her. My warm cum immediately blasts out of my cock and her eyes widen as she takes the full amount of my load in her mouth. I grab a handful of her hair until my cock is fully drained. With the last drop flying out, my muscles tighten for a moment and then subside. I pull my cock out of her mouth and she lays there with a mouth full of cum. I lay on top of her, my cock, still hard, returning to her pussy. I lean in and kiss her and her mouth opens and our tongues meet again, this time sharing my orgasm. We pass my cum back and forth between us and we kiss more passionately than we have all night. The kiss subsides and I let the rest of my cum fall back into her mouth and she swallows it. There's a drop on my upper lip that seemed to escape, so she lowers my head and licks it up with her tongue.

"That's mine," she teases.

"Yes ma'am."

I take my cock out of her and we lay on our sides, holding each other in our arms.

"That was amazing," she whispers.

"I know. You're so beautiful, Wendy."

"So are you Ashley. I feel like I know you but I just met you."

"Same here. And I never want to leave."

"Then don't," she says, a content smile on her face.

We hold each other and close our eyes as sleep overtakes us. The last thing I feel is her warm breath on my lips as she falls asleep, our faces an inch apart. I thought I'd lost her because I returned to this life but the night ends the same way the one before it did. But unlike last night, I get to drift off to sleep with the comfort of her embrace holding me tight.

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

The morning light shines in and I rub the sleep out of my eyes. I feel groggy. No, more than groggy, I feel hung over. How is that possible? I didn't have that much to drink last night. I rip the covers off and swing my legs over the side of the bed.

Where's Wendy?

I glance over my shoulder and see I'm the only one in the bed. I stand up and stretch hard and wide. And that's when I feel something is different. I bring my hands to my chest.

I have breasts.

I look down at my body and see the same familiar petite frame. I put my hand in my panties and confirm it, I no longer have a penis but a vagina. Not needing anymore confirmation, I still walk over to the mirror and look at myself.

I'm Ashley again.

I'm also in my bedroom. Not in Bay Ridge but Ashley's bedroom in Inwood. I've changed back. I guess the glimpse to my old life was only for a day. I go to my phone on my bedside table and check the date. Only a day has passed.

That's when I notice something else on my bedside table.

A silver half-dollar coin.

I pick it up and look at it and immediately I know what it means. The Fountain Man left this for me. Just in case the message wasn't clear, I notice a note on the table under the coin. The message is short and to the point.

Now you must choose.

###

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17 Comments
blackknight314blackknight314about 7 years ago
Oh boy...

Good job! I didn't see that coming. Wow. So, if he stays as Ashley, she will be happy, Wendy will be happy, Ashley's parents will be happy, Jack will be happy and better off, Ben's parents will be happy, it is a win,win, win, win, win situation.

One question, Wendy wasn't a virgin?

Love the story! Last Chapter, 9, next.

AnonymousAnonymousalmost 8 years ago
No beer for Ben dressed as Ashley?

You had mentioned that when Ben was Ashley, he missed not being able to drink Sam Adams Octoberfest Beer. But when he is Ben again, you have him drink Jack Daniels Whiskey and soda when he is dressed up as a woman. Woman do drink beer. I am surprised that since he is going to go back to being Ashley and will have a problem drinking since only being 18, that he would want to have some Octoberfest while he can. She will have a long wait before she can get some. It is a very good beer that Sam Adams makes. Should get Ashley's brother to buy some for her when she needs some and hide it from their parents.

BethesdaBethesdaalmost 8 years agoAuthor
Re: Category

JPZ: Sorry about the category mixup! I didn't even think of that. I actually submitted Chapter 8 as Sci-Fi/Fantasy but Literotica changed it to Trans. It makes sense, considering the subject matter I guess. Sorry about the mixup!

jpz007ahrenjpz007ahrenalmost 8 years ago
Catagory

Wowzer. The delay between chapters was a lot longer for those that kept checking in just Sci/Fi. This chapter made a lot of sense.

BethesdaBethesdaalmost 8 years agoAuthor
Chapter 9 Submitted

I'm so sorry for the long delay in getting the final chapter out. It was hard to leave this story behind and I had to finally stop myself from being so precious with it. I've just submitted chapter 9, so once Literotica approves it, it'll be posted. Thank you everyone for bearing with me while I complete the story. I hope you enjoy the last chapter!

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