Measuring up

I burst out laughing. “Haha good one.” I see she’s still not smiling and start to think she might not be joking. “What…. Well obviously, I’m fucking you. I mean… I’m the boy and you’re the girl? Right…?” I stammer out confused.

She tilts her head to the side, face still dead straight. “Well, what If I want to fuck you?” She says stone faced.

“But but you’re the girl… I mean isn’t that why you wanted to become…one?” I knew I had said the wrong thing as soon as I finished that sentence, as soon as I saw Kimmy’s brown eyes narrow in anger.

“Oo I see, so that’s what you think is it?” She folds her arms in front of her chest and glares at me. “The reason that I became a girl is because I wanted some big strong man to fuck me, is that right?”

I’m panicking now. Unsure what to say my face goes red and I start stammering. “What! No! I didn’t say that… I. I… just assumed?”

“Assumed what? That the woman should just bend over for the man?” she dryly retorts. “That’s sexist Kieran.”

My face has gone even redder, my mind seems to have stopped functioning under the steely glare of my best friend. My best friend who not less than a minute ago I had been passionately making out with. “I..I… I mean Kimmy, most girls don’t… have… well you… Know.”

Her glare becomes even harder as she completes my sentence “A what? A dick Kieran? A penis? So what because I still have my cock im not a girl? That’s transphobic Kieran!”

At this point my mind just stops working. I have no idea what to say and just try and push out an apology. “I…I… Didn’t mean it like that Kimmy! Im so sorry. You know I didn’t. I really am sorry.”

I stare back at her frosty glare. I see a slight crack in her frown as the corner of her mouth lifts upwards. Then before I know it, Kimmy starts laughing hard. “Ahaha! God you so easy, you should have seen the look on your face! I thought you were going to cry.”

Realisation dawns on me that Kimmy was just teasing me. My face impossibly goes a deeper shade of red. “You fucking asshole!” and grab one of the pillows from the headboard and chuck it at her. “You’re such a dickhead!”

Kimmy brings her hand to block the pillow while she continually laughs, and wipes the moisture from her eyes. “Aha I’m so sorry. I couldn’t help it you look so cute when you’re all flustered like that. Your face was so red, I thought you might have been part tomato.”

Shaking my head from side to side I start to smile as well, finding the funny side in how Kimmy had managed to tease me so effectively. “Ha, you’re still an asshole.”

Kimmy has stopped laughing and just smiles at me. “Sorry couldn’t help, I love winding you up.” She finishes with a wink.

“Ha well…” I stick my tongue back out in response. “So that means that Im going to fuck you right? You were just kidding?”

She keeps the smile on her face and shakes her head. “Nope, I wasn’t kidding about that part. We still have to decide who’s going to fuck who.”

Sighing out in exasperation. “How are we going to do that? Flip a coin?”

Kimmy scrunches up her face for a moment in contemplation and then shakes her head again. “No, it shouldn’t be up to chance. Out of the two of us, one of us must be more predisposed to fuck the other.”

The way that Kimmy was approaching this so analytically astounded me. “Pff, so what? You wanna have a dick measuring contest or something?” Jokingly

Her face scrunches up again in contemplation and after a moment she nods her head. “Yea lets do that.”

My eyes go wide in shock. “You what!?”

“Dick measuring contest. The loser gets fucked and the winner does the fucking, for the whole night. Or as you put it earlier, the loser becomes the ‘girl’ for the night.” She puts her hands making air quotation marks as she says the word girl.

I shake my head stunned. “You’re really not joking are you?” Half convinced that this still might be one of her classic Kimmy tease’s.

She shakes her head grinning. “Not even a little bit, who ever has the smallest cock has to do whatever the other person wants all night!” She turns round, presenting her red silk clad ass to me and then slaps it. “Think about it Kieran, you could be ploughing this sweet tight virgin ass all night long! You could make me do anything your sordid little mind can imagine. Don’t you want that?” Her voice becoming sultrier and sexier as she finishes.

Fuck I really did want that. But why would she suggest a dick measuring contest. I’m about 5 inches taller than her and aren’t Asian people meant to have smaller dicks on average. ‘Did she want this?’ ‘Was this her way into tricking me into dominating her?’ Staring at her beautiful ass, I can’t help but think how tight it would be around my hardening cock. I know I’m not blessed by any means, but I’m definitely above average in the dick department. Id measured and checked online, like any bored horney teenager would.

Kimmy starts massaging her ass over the dress and bites her bottom lip as she groans looking at me. “Don’t you want that Kieran? Don’t you want to fuck me?”. ‘Holy shit! She does want that! She wants me to fuck her, she is just messing with me!’

“So err… how would we do this?” I breathe out.

She instantly sits up. “Where are your keys?” She says with a grin.

“There in my suit jacket in the corner why do you nee-.” I instantly stop as I realise what she wants. Not the keys, but what’s attached to the key ring. A very small tape measure that’s attached as a keyring. I keep it with me for playing tabletop games.

Quick as a flash she’s across the room and into my jacket pocket. She rifles around for a bit before triumphantly raising my keys in the air. She fiddles with the keyring before separating it from the set and then bounds over.

“Okay you first. Clothes off mr!” she says before jumping on to the double bed again.

“What why do I have to go first?” I say a little nervously.

“Ha well, it was your idea and you’ve already got your shirt off!” she giggles with a wicked grin.

“Fine…” My face starts going red again as I start removing my socks, then my suit trousers. Now I’m kneeling in nothing but my boxer shorts in front of my best friend who is clapping excitedly. I nervously raise myself onto my knees and grab the side’s of the shorts with each hand and shakily go to lower them.

“Stop” Kimm quickly barks halting my boxers descension. “Let me do this part”. She crawls forward without waiting for my reply and shoos my hands away before replacing them with her own. She then looks up with a grin before she starts to lower them.

I gulp nervously as the first person ever apart from myself is about to see my cock. I watch her widen in surprise as my semi erect cock and balls become freed. “O wow your bigger than I expected.” I breathe a sigh of relief, that combined with the hand she has just placed on my junk quickly has me fully hard.

Kimmy has now started stroking my fully engorged cock properly. Powerful up and down motions that have been honed over her probably smaller cock. It felt like heaven, my mind was going at hundred miles an hour with anticipation as I thought about how hard I was going to be railing her from behind.

Her mouth is open in fascination as she strokes it. God how I wanted those lips round my dick. To feel that wet embrace around my shaft. To grab her head and **** it up and down its length. I start to feel more confident as these thoughts cycle through my brain. “Hey Kimmy, suck my cock…” I state trying to sound dominant.

Looking up she smiles while she continuously rubs my length. “Maybe” with a sly wink. She takes the measuring tap with her free hand and starts to pull out a length, which she puts up to my fully hard cock. “hmm… okay lets see. Oo nice so your dick is 6.1 inches. Wow it is bigger than I thought.” Her words cause me to feel more confidence. “And thickness, Oo it’s all pretty symmetrical, you have a really pretty cock Kieran.” The word pretty annoys me for some reason, but I brush it off as I look down to see she’s wrapping the measure around my length to see its thickness. “Okay and its about 4.4 thick. There we go.” She lets go of my cock and the tape measure automatically winds itself back up.

I’m grinning at Kimmy pretty pleased with the measurements and her reaction. My cock is rock hard, and I can almost feel the soft inside of her ass as I imagine how amazing it’s going to be.

Kimmy quickly stands up and gets off the bed. I watch in joy as she finishes unbuttoning the rest of her buttons on her dress and shimmies out of it, for it to fall on the floor. Now standing there in nothing but a silk red bra and red and white polka dot cotton panties is my best friend. My mouth drops open as a I take in her appearance. Pale and slim, with her black silken hair framing her heart shape face, she really was a vision. I watch her smiling as she reaches behind her back to unclasp her bra, which quickly falls to the floor to join the dress in a pile.

‘Definatly c-cups’ My brain says as I take in her gorgeous mounds. Pale like the rest her, they hang like two teardrops, topped with two ridge pink nipples. I didn’t think my cock could get harder but looking at what a vision my best friend is, it does. I can’t help but think of how this stunning creature had been under those layers of baggy clothes all those years.

Confidently striding back to the bed she quickly comes in front of me, mirroring the kneeling position I’m in. Her beautiful breasts are less than half a metre in front of me. It takes a lot out of me to resist the urge to not just lean forwards and grab them.

Her hands go down and she points to her red, white polka dotted underwear. I look down and see that they a cute cotton pair with a little white bow right at the front. I look back at her and she nods before gesturing again. “Your turn to unveil.” She smiles.

I look down again and see that there is a slight bulge, nothing to prominent, but defiantly evidence of something dwelling inside. ‘Yea she’s definitely smaller’ I reassure myself confidently. I take a breath, raise my hands to either side and lower them.