Hailey

We start of the day by going out shopping. We are dressed casually, just jeans and a t-shirt, nothing special. I talk you into trying on clothes with me at the stores we hit up. Because I know your shy, I go back in the rooms with you so I'm the only one to see you as a girl. I'm changing in the stall next to you so we can be surprised at how sexy we both look when we come out to show each other. We buy some normal girl clothes, skirts and tops and whatnot, before we move on to the sexier things. Knee and thigh high stockings, some with bows some with lace, solid and fishnet. We try on corset tops and garter belts, sexy panties and matching bras. Of course, I but mine to fit over my DD's and yours are for the smallest breasts, which I find sexy, far sexier than my own. You look so hot in all your clothes we buy almost everyhing we try on. Thank goodness I saved for this, because we buy shoes after.

On the way home I can hardly stop thinking about your little package all bunched up in those panties. I feel it getting hot between my legs.

Once home, you let me pamper you, brush your hair and paint your nails, then you do mine. Your's are pink, mine are purple. I do your make-up before my own, both smokey with highlights of our favorite colours. Now its time to dress up. We settle on one of our many patching pairs of out fits, something to match our make-up.

Undressing, I can see you're already becomeing aroused at the thought of what we are about to do. I'm aroused too, my nipples and clit are both erect.

I slip on my black stockings with the purple bows as you slip on your ones with pink bows. I dress in my purple silken thong with matching bra, then my purple and black lace gater to hold up my stockings. We are both almost ready.

I put on a sliver chain necklace with a deep purple charm in the shape of an "S", and surprise you with a matching pink "H", putting it on you and saying "Now this makes us s****rs." You smile and blush, which makes me happy. I hand you your pink and black heels as I slip on my own. One more thing we both need. Hair.

I put up my natural hair and slip on my long auburn wig before helping you put on your matching red one. "See, you're the cute one." I say looking at your reflection as you examin yourself in the mirror.

On the little table nearbuy is a small bowl which I fill with oil. We'll need that. I turn to you and smile. "I've always wanted this." I blushed, moving toward you for a kiss. We start by making out softly and lite, running hands over each others bodies, slowly getting more and more aroused as our kissing becomes deeper, more needing. My hands wander over your perfect body as my lips move to your ear and your neck, nipping and sucking. I push up your bra to lick at those perky nipples, making them harden under my tongue and between my teeth.

My hands, rubbing your stomach, move to your ass, spreading it apart and massaging your cheeks. I tease your cock through your panties gently with my teeth and hot breath, at the same time teasing your asshole with my perfectly manicured finger.

I slip your panties down and off, dipping my fingers into the small bowl of oil, spreading your cheeks in front of a mirror to watch as I run my fingers round your hole, your little whimpers getting louder and more frequent. They are really making me wet.

I look into your eyes as I take your erect clit into my mouth and gently suck you, feeling your skin harden in my warm mouth. You moan and your body begins to move, pressing ourther and further into my mouth. Unfortunatly I gag easy, but fortunatly, you are shaved smooth everywhere, so I have no problem taking your balls into my mouth and caressing them with my tongue as I slip a finger into your eager ass.

My finger slip in quite easily from all the times youv'e played wit yourself. I think of the first time I saw your videos online, how wet they made me, how much they made me want you. You're so sexy, and it makes me so glad to put that look on your face. That look of growing pleasured, of wanting me to give you more, and it makes me feel lucky. Lucky to know you.

I moan around your ball sac and slip my finger in deeper, pumping it and curling it against your walls. You gasp and your cock twiches when I bump your prostate. I smile, tonguing over your shaft as I work in another finger to bump it again, causing you to let a rather girlish moan.

I see you, chewing on your fingers and your brow furrowed in pleasure, your eyes closed. I can feel your heart beat.

I slip my fingers out from your little hole and stop the torture over your manhood, to which I smiled thinking of how you see it as more of a clit than a cock.

"I'm so wet for you. My pussys screaming for attention. Would you?" I asked looking into your eyes. "Would you eat out my smooth pussy and make me cumm for you?" I say to make you blush. Your face turns red and I smile when you nod.

I sit on your bed, spreading my legs and running a hand over my paties, which have become quite wet. Moving my panties to the side, I look up at you. "Eat me." I command, pleased to see you drop to your knees and crawl to me.

You come up to me, face to-, well, face to pussy. I feel you breath in my scent and sigh. "Mmm you smell good." I smile. "I taste even better. Now eat." I say again.

I gasp when your tonge flicks across my already erect clit. Your tongue moves over my inner lips, so swollen with lust. Your tongue, slipping between my lips and moving stiffly yet still gently up and down, so warm on my clit.

You surprise me when your tongue wiggles in, then suddenly moves down to lick around my asshole. "Ohh! If you do that I'll cum all over you." I moan. "Please cum on me." you say moan softly, sucking my lips and kissinging them before moving right back to my asshole to rim me. It feels so fucking good that when you lick it furiously and pop your little tongue into my pussy I yell and cum, messing up your face.

"Fuck me, Hailey! I didn't know you'd be so good at that. Are you sure you've never eaten pussy before?" I say a little winded. You shake your head no and I pull you up into a sloppy kiss, licking my juices from your swollen lips. I taste so good off of you.

We fall back and roll around, kissing and rubbing our bodies together. Your clit rubs against mine and we both moan. I feel you try to slip into me and I pull away, swatting your hand. "No, no, Hailey, that's not how this works." You look at me sadly and it almost breaks my heart. I smile and kiss you gently, petting your face to reassure you. "You will, but not now. I have to do you first remember?" I'm pleased to see you blush, but nod. Leaning in to whisper into your ear, I gently breath. "My cock is so hard for you." You moan at my words.

Getting up, I slip out of my cum filed panties and reach into my bag for another surprise. A purple strap on, a bit larger than your own toys and much larger than you thought you'd take from me. I slip it on and smile as you begin to rub yourself watching me.

"I want you to suck me first." I say standing by the bed. You turn eagerly and sit up, sucking on my cock immeduatly as if it were real, like you really wanted to please me and make me cum for you. How I wish I could. The rubbert material under the balls of the toy rub my pussy and make me moan, which only makes you blow me faster. "Yeah, Haily, suck my cock for me, make your s****r nice and hard for you." I moan.

I see you rubbing your swollen clit, already leaking pre-cum from all the for play. I pull out of your mouth despite your protests. How I want to fuck you in the position you're in, but I know you get off better being treated like a slut. "On all fours." I say in a commanding tone. When you don't move fast enough, I push you onto your stomach and say louder, "I said on all fours!"

You let out a cry which is so erotic I swear my cock twitches. Rubbing the oil over it, I get behind you quickly. I can't wait to pund my big cock in your virgn hole.

It puckers so cutely when I spread your cheeks and oil it smoothly. I spready your hole as wide as I can, and still, as much as it would let me, my cock is still too big for your hole.

"This may hurt slightly." I say gently. "I am takining your virginity after all." I smirk, rubbing the head over the hot hole that so desperatly wants me. I push the head in, almost about to feelo how tight your ring is around it, how much it squeezed it. I wait and push in a little at a time till the whole thing is in and I'm burried to the hilt.

You're clawing at the sheets at this point, the material bunched up in your fists. I grab your hips gently and pull back before pushing in agin slowly, over and over, but only a few times before I get rough. I know you like it rough so I pull back almost all the way and shove in quite f***efully. The strap on is rubbing my pussy so much I feel I may cum again.

"You're so fucking tight!" I yell, you almost crying in responce. "I didn't get that, what did you say?" You don't answer, but instead only whine. I slap my hand on your ass, not lightly but not hard either. "Say it." I command. "Ah, you're so big!" You cry out. I moan and continue to rock my hips, enjoying havng you under my control like this. "You like big sistrs cock inside of you?" I ask. I'm a talker and love to be talked to. When you only answer "Yes" softly, I spank you again, you moan. "Say it, tell me what I want to hear!" I yell and you moan as my hand comes into contact with your reddening skin again. "Ah, I love big s****rs cock inside of me! Please!" You cry "Please, I can't take it anymore," you actually cry "It feels so good, I wanna cum, please let me cum, big s****r!" The way you cry is so heartbreakingly erotic I want to cry myself. I reach around for your clit and jerk it in time with my thrusts, pumping it until we both cum, our screaming orgasms echoing through the house.

After your orgasm subsides and the blissful afterglaw kicks in, I pull out of you and lay down next to you, collapsing. You collapse as well, us both breathing harshly still. I look at you and you look at me, and we share one last kiss before you drap your letg over me and hold me close to you. I wrap my arms around you as well and cuddle you, listening to you breath until you fall asl**p in my arms. I fall asl**p as well, smiling at how mucky I am to have met you.

End.
100% (56/0)
 
Categories: AnalFetishFirst Time
Posted by ShyxGirl90
3 years ago    Views: 2,163
Comments (33)
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9 months ago
So wet from this... x
11 months ago
Great story!
1 year ago
it drive me so hard honey, loved
1 year ago
I miss Hailey soooo much! She was my favorite gurl ever!
Yummies,
Trishy
2 years ago
Sexy story! Now make it into a movie!
funsearch1
retired
2 years ago
this is hot! i would love to have a day like this once
2 years ago
such a good story!
2 years ago
fabulous story:)
2 years ago
Fantastic story !!!
candi0058
retired
3 years ago
O M G i came three times and i'm still hard will have to take care of that now thanks Candi
penissucker
retired
3 years ago
Please write a book!!!
3 years ago
Really HOT story...got me hard and wet
3 years ago
Wow!
watchnstr...
retired
3 years ago
Great story. Excellent erotic fun!
3 years ago
Niiiiice!
jacquin001
retired
3 years ago
I couldn't stop playing woith myself i had to jack off until i came all over ny levis thanks
3 years ago
This is the 4th story that i've read that has made me orgasm while reading it :p and thats not an easy thing! err well i think?
3 years ago
Very well done! I'm so hard right now I can't stand it! I love it!
3 years ago
Very erotic story, I love it!! xxx
3 years ago
Just read this all the way through. Fantastical.
RustyShac...
retired
3 years ago
Damn that is fucking great!
3 years ago
I loved it, I would need to read it a few more times to really get the feel of it, but what I skimmed I liked. I love cum filled panties, and I don't care who or how they got that way.
bunniecd
retired
3 years ago
Wow, I love everything to do with this!
3 years ago
my dream date
xx
3 years ago
i love that story Hailey it was tching and so hot anyone would be lucky to have yu
3 years ago
great story ...very hot. Who cant imagine having that experience with Hailey.
3 years ago
wow what a great story
Hailey_gurl
retired
3 years ago
I absolutely loved it, this is like my dream scenario... so ridiculously hawt =)
< 3
3 years ago
So well written, and the flat-chested trans girl must have been hot as hell. Reading it one might think of lesbian love, know what I mean, so gentle and erotic on one hand but then with the strap on things get a little rough. Mission Acomplished, this story will make everybody horny.
bertje
retired
3 years ago
WOW Stef!! sooo erotic.....