Know Thyself Ch. 07

"So, still single?" He asks me.

I nod.

"That's always a good thing when you start college. Take a minute to meet new friends."

I nod again, not having anything to say back to that. We could sit here and small talk all day, so I decide it's time to cut to the chase.

"What do you want from me?" I ask him.

He blinks for a moment and leans back. So, Mr. Confidence got caught off-guard.

"You're the one who texted me," he replies with a sneer. "What do you want from me?"

What do I want from him?

"I've been curious about something."

"And what is that?" He asks with raised eyebrows.

"When we first met, you invited me back to your place for a drink."

He nods.

"Let's both be honest here. I know what you want."

We have a small staring contest for a moment. I'm not going to say anything until he does. I want to hear him admit it.

"Good. It'll make things easier to be upfront," he says.

"I've had a rough couple of weeks on the relationship front."

I wait to see if he'll say anything to this but he doesn't, so I continue on.

"It feels like no matter what I do, things will always end badly for me. Like I'm destined to be single and alone my whole life."

"Well, you're young. You have a lot of time."

"I know. My question for you is about your wife."

He shifts uncomfortably in his chair and I see his hand instinctively cover his wedding ring again.

"If you have someone at home who loves you, why would you want anything from me?" I ask, sounding bewildered by the idea. "I mean I get being horny. We all get horny. But why would you risk it? Just to have sex with someone one time?"

Again I decide to stay quiet until he says something. I can see him try to formulate an answer. He's no longer looking at me in the eye, but instead at the table.

"Not every marriage is happy," he says.

"Are you looking for a way to end it?" I keep an edge to my voice to let him know this isn't an offer but rather a warning.

He looks me in the eye again. "No. I'm looking for a way to sustain it."

I understand what he means but I don't want to accept it.

"You have no idea how lucky you are," I say. "I may look young but believe me, I've been around longer than you know. You're very lucky."

There's a long silence that falls between us. I'm not sure what else to say and I think he's feeling the same way. I haven't noticed until now that there's music playing through the shop's speakers. It breaks me out of this seclusion the two of us created around ourselves. He looks at me and again I feel drawn into him. I wonder if it's something he's doing on purpose or if it's just the way he is. There's a sadness in his eyes but he masks it well. How can someone who has so much come to this point? He has someone to go home to everyday. I would give anything for that. As Ben, I always felt this ticking clock counting down the days of my worth. The day I turned into Ashley was my thirtieth birthday. When you're in your twenties, the dating world feels like a game of musical chairs. You need to find your seat before the music stops. You don't want to be the last one standing without a seat. Though I was still circling the chairs, I could tell the music was going to cut out soon and there wouldn't be a chair for me. Here this guy found a way out of the game and yet he's still circling. It's this fact that repulses me and draws me in at the same time. I want to feel that feeling with him, pretend I'm his wife, see him look at me like he looks at her. Yet the fact that he's willing to do that makes me hate him as well.

"You're the one who's lucky," he says. "If I could go back to your age and do it all over again..." He shakes his head and trails off and I can tell he's reimagining his life. I wonder what it looks like.

"I doubt it would help. No one can change their nature," I say.

He huffs, a chuckle and he looks at me freshly. "You do seem older than you look."

"Do you have kids?" The question seems to just blurt out of my mouth.

"No. Why?"

I nod, averting his eyes. "Just wondering."

He looks to be sizing me up again. I'm not sure for what.

"What are you doing Monday night?" He asks.

"Why?"

"My wife will be gone. She's going to a fundraiser at an art gallery. I already told her I'm not going. The Knicks play that night and I don't go out when the Knicks play. Part of our marriage contract. What do you say?"

I know I shouldn't. I know I keep saying I shouldn't. I know it's pointless to keep pointing out I shouldn't if I'm not going to listen to myself. Going over to his place when his wife is out doesn't mean I'm committing to anything. I'm just going for a drink. We'll chat some more and that's it. It's just a drink.

"What's your address?" I ask.

Maybe I should remind myself again I shouldn't.

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

The worst part about being Ashley is not being able to buy alcohol. It's October and I can't buy any Octoberfest! I don't care what anyone says but I love Sam Adams Octoberfest. I think this just might be the first fall season in a long time that I won't be able to have any. What good is an October weekend when you have to spend it sober?

I wonder if I'll still be Ashley on her twenty-first birthday?

That's three years away. There's no way I'm going to go without Octoberfest this whole time.

Did I mention I really like Octoberfest?

I have the whole weekend to myself. There are no tests or projects due in any of my classes next week, so there's nothing to study. I don't have any plans with anyone since I don't have any friends at the moment. What is a girl to do?

Maybe this is a good time to explore things I've been neglecting for a while?

Okay, so if I'm being honest, I've been really horny all day. The moment I woke up I rubbed my clit until I spasmed and soaked my sheets. Unfortunately this didn't seem to subside my desire. I hope I'm not getting my period again. When I did research the last time I read somewhere that some girls get really horny right before their period starts. I wonder if that's true. I don't remember getting overly horny the last time, but then I didn't know what was happening to me. It's been about three weeks since then, so it's time to start thinking about it happening again. Whatever the reason for my horniness, it doesn't change the fact that I am in fact very horny. Then I remember the plan I had earlier in the week.

Buy a dildo.

I should feel what it's like to have a cock inside me. I'm not going to go out and sleep with some random guy, and I'm not going to sleep with Charles. Our meeting for Monday night is just to chat, no sex. Maybe it's time I go buy a dildo and explore my new body further than I have. Not to mention I'm starting to think I'm only into girls now since boys haven't been doing it for me lately. Even this morning when I masturbated I only thought of girls. But I can't help this craving to have something hard inside me.

I check my bank account to see if I have enough money. That's when I realize I have no idea how much this will even cost. I've been inside porn shops before as Ben, but I only ever bought a DVD and once I bought a fake pussy. There's not much reason to go to porn shops now-a-days. Unless you're buying toys, what's the point? I didn't even keep the fake pussy for that long. I was in college and I had to keep it in my dorm. I was so nervous that someone would find it that I threw it out after a week.

I know there are porn shops in midtown. There used to be a lot more but most of them closed because of Giuliani. However, I do remember passing one or two whenever I've been in midtown. Before I know it, I'm on the train heading down to Forty-Second Street. This has always been my problem as Ben. Given time to myself, I'll always get up to something I shouldn't.

What's wrong with doing this? No one is going to get hurt because I bought a dildo.

That's true. This is just another form of me masturbating. No one gets hurt when you play with yourself. I'm a girl looking to enjoy her body.

When I get out at Forty-Second Street I'm greeted by the barrage of tourists. I forgot how much I hate midtown. It's funny how people come to visit this city and they go to the one place that no native New Yorker goes to. I weave my way through the hoards of people and head south on Eighth Avenue. I know I've seen a shop somewhere between here and Penn Station. I can't remember the last time I've been in midtown. As much as I want to hate it, it does feel like New York. Tons of people, giant electronic billboards, people trying to sell you tickets for shows on the street. I think every New Yorker has a love-hate relationship with midtown.

I soon forget to keep an eye out for an adult shop and just as I remember I realize I'm walking by one. The blacked out windows give it away, though so does the merchandise you can see from the door. I walk in and you would think the record just stopped. Everyone within sight looks at me. Some straight on and others out of the corner of their eye. As if it's not embarrassing enough to be in an adult store, everyone has to be looking at me? I duck my head and start walking to the back of the store. I don't even look to see if I'm going in the right direction, I just want to get out of the front of the shop.

I head down an aisle of DVDs that seem tame at first but get more hardcore as I make my way down. There's a man browsing near the end of the aisle and as I pass by, I can feel his gaze. That's when I realize it.

I'm the only girl in this place.

At least, the only one I've seen so far. Not to mention I'm definitely the youngest. Now standing at the back of the shop I look around to see where I should go. Maybe I should go up to someone who works here and say something like "excuse me good sir, may you direct me to your dildos?" I chuckle to myself and the man I passed by hears me. He glances over and smiles.

No thank you, I'm just here for the rubber kind.

Are they made of rubber? I think about it as I make my way to the far wall where I see a bunch of toys hanging up. When I get there, I'm greeted by a wall of penises. I've never actually seen a dildo in real life before, only in porn. It's kind of amazing actually. They come in different sizes and skin tones. Some vibrate, some have special features, it's actually overwhelming. I realize I'm gazing up at this giant wall of penises with my mouth hanging open.

Get control of yourself, Ashley! People are watching!

I collect myself and try to play it cool, glancing around me. No one is in this aisle. What's wrong guys? None of you want a dildo?

As I look closer I start to see the prices.

Holy shit! Fake penises are expensive!

I don't think I'm going to get anything with special features. Just your garden variety dildo will do for me. I finally find one that's a straight up dildo (no pun intended) and has a reasonable price of thirty dollars. I still can't believe it costs that much but it looks like it's the cheapest one I'll find. It actually has veins on it! We can't cure cancer but we do have fake penises with veins on them. It's sad really, but I'm too horny to think about it.

I walk my purchase up to the counter. Why does the counter have to be so close to the front door? What if someone I know walks in?

Then you'll both be in the same place and neither of you can judge the other.

The Indian man behind the counter eyes me as I walk up. I place the dildo on the counter and take my debit card out. For a moment he doesn't move, he just looks at me. I raise my eyebrows to ask what the problem is.

"How old are you young girl?"

Young girl? Who does this guy think he is?!

"Eighteen. How old are you?"

I probably shouldn't have added that last part but oh well, it's been done.

"Can I see some ID?"

I wonder if there's a real problem with underage girls buying dildos? Probably not, but then again, if they sold sex toys to minors it would probably he a big deal. Probably criminal. I oblige and hand the man my ID. He inspects it and nods, handing it back to me. After he rings it up, I hand him my card and he places my purchase in a black plastic bag.

It looks like the same kind of bag you get from a sketchy liquor store.

I take my card and make my way out of the store. Once I'm back on the street, I look around to make sure no one I know has seen me. This city is much smaller than most people think, though I'm probably still being paranoid. I walk fast back to the subway, though I'm not sure if this is because I want to get away from the porn shop or if I want to get home and try my new purchase.

I like that now I can say "my purchase" instead of "giant rubber penis".

There doesn't seem to be anyone paying attention to me on the subway, even though I have this very obvious black plastic bag. Nothing good comes in a black plastic bag. That's when I realize the mistake I've made.

My dad looks at my statement!

Fuck! I swiped my debit card in there! Why didn't I take out cash and use that? I wonder what the charge will show up as? I can't look now since I'm underground on the train. I can't believe I was so stupid. How am I going to explain this? Maybe it shows up as a nondescript charge. I certainly hope so. How can I say "sorry dad, I spent thirty dollars on a dildo because I was horny and had nothing to do all weekend."

Maybe he doesn't look that closely at it?

Wishful thinking. When I get off the train and get above ground, I franticly pull out my phone and open my bank's app.

Eighth Avenue Boutique.

Oh thank God! That can be anything. I'll have to come up with a cover story at some point but for now I'm in the clear. I enter my building and make my way up to my floor. When I walk through the door, my dad is sitting on the couch.

"There she is!" He says enthusiastically. Did I miss something?

"Hi," I say, trying to sound casual. "What's up?"

He shrugs. "Nothing." He nods to the TV. "Rutgers."

College football is on. I wonder if my dad went to Rutgers?

"What'd you get?" He asks, nodding to my bag.

Shit.

I stumble for a moment. "Um..."

He gives me a sideways look.

"Girl stuff," I say. I don't really know where that came from but I guess that's what I'm going with.

My dad has a look of comprehension and signals that he's done asking questions. I quickly get out of there and go to my room and lock the door.

It's times like this I miss living on my own.

I take the dildo out of the bag and lay it on the bed. It's wrapped in a plastic casing like my old action figures used to be. They're not kidding when they call it a toy. It's also hard to get into. I try to tear the plastic casing apart with no avail and of course that doesn't work. I need some scissors. I'm pretty sure there are some in the desk drawer. Sure enough there are and after a moment I've got the thing out of the plastic.

I hold it up in front of me like some treasure I just found. If I was looking at myself right now I'd be laughing my ass off at how ridiculous I look. I don't know why this is such a big deal to me but it is. Not only have I never used a dildo before, but I've never felt what it's like to have one inside me. I'm kind of nervous, which is even more ridiculous because I'm the one doing it to me.

I start to undress and lay naked on the bed. I'm already a little wet from the anticipation. I rub the tip lightly on the outside of my pussy, still nervous to do anything further. The rubber surface is kind of rough and I realize I probably need to lubricate it with something before I do anything more. Well, there's always my mouth. It won't be the first cock I've sucked (if you consider this a "cock"). Although, this one is much bigger than Matt. This one is much bigger than mine (when I had one), so no offense to Matt.

I open my mouth and slide the tip in. It tastes kind of weird, like rubber or plastic. I can't really tell what it's made out of. I glide my tongue around the dildo to lube it up. The eight inches can't go all the way in, but I'm suddenly interested to see how far I can actually take it. I push it a little more and my gag reflex kicks in, so I quickly take it out. I only made it about halfway. I slide it back in and try to go a little deeper this time. It doesn't look that thick but even the head fills the opening of my mouth. I push it in and out a couple times and the familiar motion starts to get me a little more wet. I finally push it down further and get about halfway just as my gag reflex kicks in again. I try to ignore it and keep going. I get slightly farther before I have to take it out.

Wow, how do some girls do that? Or is that something that only happens in porn?

I never had a girl deep throat me before but I also didn't have tons of sex to begin with. The gag reflex certainly doesn't turn me on, but the motion of sucking a cock does. The dildo is pretty wet now, so I lay back and spread my legs. I use one hand to rub my clit and the other brings the dildo to my wet opening. I slowly slide the tip in and immediately I feel a jolt through my body. I slide the tip in and out, softly getting myself ready to take it's eight inches inside of me. The combination of rubbing my clit and playing with the head of the dildo gives me a warm feeling all over. It's the same level of pleasure as when someone is eating me out except there's something different. Something I can't explain. I start to get lost in the pleasure and that loss of control is when I instinctively push the dildo further inside me.

"Aaahhhhh." I let out a moan as I do it, the surprise adding to the pleasure.

Now the dildo is pulsing in and out of me, not fast but steady. I can hear my juices squirm with each pulse of the dildo. So this is what it feels like to have a cock inside of you? It's amazing, like nothing I've ever felt before. Well, it is nothing I've ever felt before. Maybe I'm biased because I'm in the body of a girl right now, but this feels better than any sexual experience I ever had as a man.

I take the dildo out and cup my pussy with the hand that was massaging my clit. I thrust my pussy up, lifting myself off the bed. My muscles keep clenching and the motion is almost like stretching, to let the feeling of pleasure continue to circulate through my entire body. I slide the dildo back in and this time I quicken the pace. The base of my hand smacks against my skin as the dildo fucks me harder. I start to lose control of my body and I move without thinking. My head arches back and I push my breasts up, as if there's a balloon of ecstasy inflating inside me. I finally push the dildo deep, taking the whole eight inches in and I hold it there for a second. Where I used to have a penis, there's now one inside of me. I can feel it deep. Or maybe that's just my imagination? I can't tell. My body can't take the wait anymore so my hand continues to fuck me. I can't stay quiet. I've been trying to suppress the need to cry out, to release the tension of pleasure by moaning to the ceiling. I take a pillow and put it over my head, holding it tight as I yell my passion into it.

My hand is now drenched and I can tell the explosion is coming. I take the pillow off my head so I can see what the dildo looks like inside me. That's when I see the vein, plump and pulsing. I know it's not really pulsing but in my current state it's hard to tell what's real and what isn't. I know I'm masturbating but it feels like someone else is doing this to me. Finally, I bring the pillow back over my face as my pussy explodes. The dildo comes out one last time and it's followed by a flood of warm juices. I yell out into the pillow, unable to stop myself. The hand that used to have the dildo cups my pussy as my legs clamp up tightly. I roll over on my side and spasm a couple times as the explosion subsides. I can feel how damp my sheets are as I lay on the wet spot. I'm finally able to take the pillow away from my face and I take deep breaths in and out, though I can hear how uneven they are. This body cums so much stronger than I ever used to as Ben. I also realize something I never knew when I was a man. The minute I came, I didn't want anything inside of me. Without thinking I took the dildo out and tossed it aside.