Turning My Boss's Wife Gay - Day 01

Day 1

Normally when someone sets themselves a challenge, and keeps a diary of how they're working towards it, their challenge is something like running a marathon, or losing weight, or planning a big event.

Not me. My challenge is different. I've given myself 30 days to fuck my boss's wife.

I'm Cara. I'm 23, I'm bi, I have pale skin and dark hair and a petite 5'2 body. I have exactly one tattoo, but it's a pretty great one: a branch of roses inked in black on my pale shoulders and down my back. I have one piercing, a nose ring, and that's it.

That's enough for now. You'll be learning a LOT more about me over our 30 days. And don't worry -- if you're the kind of reader who skips ahead to the naked stuff, I get naked in like two pages' time. Promise.

So today my boss brought his wife, Alyson, into the office.

We're only a small team and my boss, Chris, likes to keep things informal, "like a family" as he says all the time. So, when a new person starts, his wife comes by to introduce herself.

The new person is me. I've only been at this company a couple of weeks. My job is...well, it's something to do with analyzing data and it's way too boring to describe in any more detail.

Alyson -- "Call me Aly!", she insists -- is the kind of woman I can best describe as obviously marriage material. She's a little taller than me, 5'4 perhaps. Curly light brown hair falling down into ringlets. Green eyes. A few cute little freckles. She's wearing a subtle floral print dress and a pair of sneakers.

And she's really attractive. Not in a cold, sharp, supermodel way, but in a warm, inviting way. She smiles a lot. You want to be her friend, because you know immediately she'd be a brilliant friend. You want to visit her house, because you know it's homely and comfortable and well-decorated. She'd look equally great in a ballgown or a pair of ripped jeans and a baggy t-shirt. Make-up or no make-up. Hair done or undone. You get the idea. Marriage material.

I'll be honest. The moment I saw her my heart flipped over. I knew. I just knew. I would find a way to be with her. I had to. All I cared about from that moment was finding a way to get this perfect woman into my bed and between my legs.

"And this is Cara," my boss said, introducing me. The rest of our team was standing round, waiting for their turn to chat with Alyson. Probably everyone in my office, male and female, had a crush on her.

I shook Aly's hand and smiled. "I love your dress," I said.

She beamed. "Thank you! It's great to meet you. You've already made such a big impression on Chris." She leaned in and did a stage whisper for everyone to hear. "I think you're his favorite." A few people laughed. Just wait, I thought.

Thankfully I didn't have to say any more because Chris produced a bottle of wine from somewhere and then everyone started chatting and I managed to keep a fairly low profile. Aly stayed for about an hour, laughing and joking as if these were all her best friends, and I watched her, my mind racing.

Would she ever cheat on her husband? Had she ever been with another woman? What if the answer to both those questions was yes but she'd never touch one of his employees? What if the moment she figured out I wanted her, she told Chris and I got fired?

But I was drunk on the idea, so overwhelmed by it that I had to avoid making eye contact in case the whole plan came spilling out of me.

On my journey home I made the rules for my challenge. They're VERY specific.

Rule Number 1: She has to want me. Like, really want me. Not just a kiss in the corner of a noisy bar that she can pretend was a drunken mistake. Not just her going along with what I want or "letting" me do stuff to her. So that leads us to...

Rule Number 2: I only win the challenge if Alyson goes down on me. She has to do it to me. And she has to want to.

Rule Number 3: Not in a threesome. We're not just performing for her husband's pleasure. When I'm with her it'll just be for me and her.

Rule Number 4: I am, however, allowed to fuck my boss if it helps me achieve my goal. I don't know how it'll help but I'm keeping my options open.

By the time I'm home and I've finished writing my four rules down -- what's the point of rules, after all, if you don't put them on paper? -- I'm in a daze of excitement and desire. I'm drunk on my meeting with Aly. Maybe I'm kinda thrilled by my own stupidity.

I'm also wet as fuck.

I lie back on my bed. Normally I'd just grab my clit now for some quick relief. But I force myself to slow down. I need to teach myself a little patience after all. Some self-control.

Slowly, slowly. I unhook my bra and peel it away from my breasts, teasing my nipples playfully between my fingers.

What if Aly sleeps with me and it really is her first time with a woman? Will she be nervous touching me? Will she touch me how she likes to be touched?

I remember my own first time with a girl and I laugh because I was most definitely NOT nervous. I was so hyped up and ready for it I pounced on her cunt like a starving animal...but that's another story for another day.

I gather my whole breast in my hand, clutching myself as the memory flickers through me and I refocus on Alyson. My hand slides gently down my stomach, just lightly brushing a path with the backs of my fingers. I take a detour over my inner thighs, lightly stroking them, teasing at the edges of my underwear.

I imagine Alyson's fingers taking the same path. Her hand is a little unsteady. She's got this far now and she isn't sure when to go further. She pushes my legs apart...my hips flex impatiently...she pulls down my panties just slightly, revealing my neatly trimmed front, the hair short and dark against my white skin. And then she finds the courage to slide my underwear completely off and I show her the full spread of my aroused little pussy. She plays with my lips for a second, gently brushing the tops of my inner lips. I moan. She goes a little slower, taking some of the wetness from my dripping vagina onto her fingertips and smearing it up towards my clit and...

Fuck. I can't wait. Imagining this, copying every fantasized action with my own hand, is too much, too intense, and all I can do is grasp my fingers over my clit and move them hard, forcefully, rhythmically, all the way over the edge into a shuddering orgasm.

I clean up and I've just about got enough energy left to finish typing this, and then I'll need to eat and sleep and dream...and plan.

That was Day 1. I'll see you again for Day 2.

Cara.