my night with Ashley

decided to give myself a writing assignment. A lot of what is in this is true, but like any good fiction writer... you get the imagination with bits of "research" and real life experience. Hope you enjoy

story for the night

It was a Saturday night. I'd always been attracted to trans women but I'd never taken the plunge. Spending this night like any other I'm online on an amateur site watching the ladies have their fun and I decided... tonight's the night I go for it. The main factor in my decision not to up until this point wasn't me being shy, or closeted, or a chaser. Nope. I grew up poor and in Mid City Los Angeles. Appreciated every dollar I made and stayed away from anything that might get me addicted. I knew that once I dipped in this pool once it might become an expensive habit. I knew that going in. So I thought

And I see a girl in my town... ThickDickAshley. I've looked at her pics and vids countless times, but tonight I decide to BE the fantasy instead of watch it again. I give her a ring... she answers. I introduce myself and my intent. She's down and asks if I'd ever been with a trans woman before. My ass is virgin. I haven't even put a finger in it I tell her. She gives a seductive laugh and tells me bring that sweet hole to her so she can pop my cherry right. I ask her what's a good donation for an hour of her time. She answers and asks me to come right now. Just the sound of her voice asking me to come keep her company sends my penis into a rock hard state that brings Richard Pryor's line about cutting diamonds to mind. Its about 2 in the morning and I figure sure why not. I get directions and I'm out the door after freshening up.

I don't know the slightest of how things like this go... and I'm treating it like a first date. On the way I call and ask her does she want me to bring her anything from the street. She says just my tight ass... and maybe a Pepsi. I stop at Rite Aid and stock up on the essentials... lube, condoms, a box of Red Bulls and a 2 liter for her.

I get to her spot. I call... she answers and tells me just come knock. I do. She answers he door in fishnet stockings and a short dress with an obvious bulge from no undergarments.. and is also smoking a sweet smelling Dutch full of some exotic smelling Kush. At this point all I could do is smile thinking to myself what have I gotten myself into?

I give her a kiss on the cheek and her Pepsi. She smiles and giggles... "I would have been fine with a can. Yeah you're making the right impression :wink:"

after some introductions we proceed to her room which is lit with a Cranberry Orange Yankee candle on the dresser and a couple of votives on her nightstand... which also had a box of gars, some black and mild's and at least half an OZ of the same stuff she'd come to the door with.

I ask her if its ok if I smoke with her and she laughed... "normally I'd have all this stuff put away and all but I had a feeling about you when you called. Tonight could be fun." She proceeded to roll a few blunts. I admired her work. Just the way she handled it, licked it and rolled it made me imagine what her tongue must feel like on me. I kept my composure though. No stiffy. As she lit up she took off the dress and I got to behold wonderful natural C cups and a beautiful uncut chocolate bar sticking out of the crotchless fishnets. From the pics and video I'd seen online it was hard for me to imagine that she could even get that small...

"for tonight because you're a virgin... I'm gonna treat you."

She tells me take everything off and lay comfortably. As we pass the blunt she lights a black and mild and tells me "this one is for up... this one is for down. Just keep smoking ok?" As I nod she lays me back and starts to kiss my neck and works her way down. When she gets to my waist she stops and says "me first"

so this is how I suck my first one eh? I give her balls a few kisses as I stroke her a bit to get her going. The one thing I notice is that she doesn't jump straight to a hard on like I would. I like that. It makes me feel as I have to work for it. SO I begin. I start with her whole semi erect in my mouth. I work my tongue around her head and I can feel her growing in my throat. I take a breath in my nose and ask the randomest question that comes out a bit muffled

"do you have some honey?"

she laughs and says "out of all the things you could ask for right now.... honey?"

I explain... "An old pimp taught me this. If you got somebody with gag reflex get some honey and tell them to drip it down the back of their throat down the tongue. It will open up the throat and no gag."

she stops laughing and gives a look of astonishment... and goes to the kitchen. A few moments later she's back with honey in hand. I try the method and get back to where were after another hit of the blunt. By this time she's almost fully erect and I can feel every inch of it attempting to tickle my tonsils. I keep going for a few minutes and she enjoys... grabbing my head and making me go all the way down.


She tells me lay on my back and puts a pillow under my butt. Up until now I haven't actually seen what I'm working with in all its glory. I catch my breath, smoke some more and take a look as she reaches for a condom. This thing has gotta be 8" easy. She lubes me up... Magnums up and sticks a finger in me. She works it around for a few minutes asking me am I ok. I tell her I am and she starts to the task of opening me up. She sticks the head in and I gasp. "You ok?" I am... she keeps going. Further.... further and shes in. I mean IN. I let out a moan that I didn't knew I had in me. She smiles and lights the black and mild. I light another blunt and lay back and try to get a grip on what is happening right now. Is this what heaven feels like? Well minus the discomfort in my ass... maybe.

She starts to find a rhythm and proceeds to stroke me. At this point I'm firing on all cylinders and I don't even know what to pay attention to... the blunt and black we're passing back and forth, her fucking me, her stroking me, or the way she's talking to me all seductively yet dominant. "This is the tightest ass I've ever had. This is my ass from now on."

Then it happened. It started as just a sensation that felt like a push from behind my scrotum. The more she worked the bigger this sensation got. Then she asks me "you ready to show me just how good you feel?" Before I could say yes she starts to work me like my ass is the loosest pussy ever. I'm hurting but in a good way. I spread my legs into a split and she takes her arms and pushes hard behind my knees and we are basically linked coccyx to ass. The feeling I had before is now to the point where it feels like I have this ball of fire working its way thru my loins and to my penis. She strokes me a big as she's going like there's no tomorrow and I lose it. She stops stroking me long enough for me to bust the biggest shot I'd ever had in my life. It went all over my chest, face, hair and above me on the bed.

"Ooh you really weren't lying about the V thing... good" She strokes a few more deep thrusts and pulls out and aims for my still throbbing penis ... which is still rock hard. Off with the magnum and after a few strokes and teasing me "you really want this nut don't you? Imma give it to you because you deserve it" ... and boom. I didn't know what to expect from her cumshot as I'd seen it online only once, and that vid was a few years old so I didn't know what things such as hormones and such had done in that dept. Needless to say I had nothing to worry about. Out comes this warm pearly cream stream that seems like its trying to chase my previous shot. I must have counted 8 gushes as they landed on my dick, stomach and chest.

"you have the BEST ASS I've ever had and I don't cum that quick. Told you you were special"

I asked now what. She says "we smoke some more and relax"

so we lay. I put my head on her chest and hand on her slowly shrinking stick. I just bask in it all and we nap for a few.

Then I wake up to a hand fondling my balls and a tongue licking the head of my dick. She starts to suck me and its the best I've ever had. She says "smoke some more... I told you keep smoking". So I do. I get that feeling behind my scrotum again but its not as pronounced and after a few minutes I cum.. again... like a fountain.

"my turn"

Another magnum and me back in that position and she's in again... but this time she's making love to me. The strokes are more rhythmic and she holds the back of my neck as she pulls herself in. This time I hear "ohh not so fast again and this time she cums in the condom in my ass"

by this time I'm on cloud 9000. "you got one more for me?" she asks as she strokes my STILL HARD WOOD. "Keep smoking"

I do and as I'm getting close she sticks two fingers in my ass and does some type of motion like come here. Next thing I know I nut again... as much volume as the first 2 if not me.

By this time I know that I've had just about all I can take and I ask for a break. She says she's done and curls up on the bed. "you can shower if you want but I'm gonna go to sleep. Your ass took everything I got"

I dress slowly... basking in the afterglow. I kiss her on the forehead tell her that I'll be back soon and go sit in my car for about 20 minutes re-creating in my mind what just happened.

I told myself this was just a one time thing. I don't wanna get hooked. I don't wanna get hooked. I don't wanna...

I was back a week later, every week for 3 months. Unfortunately for me it wasn't funds or moving or losing a number that ended our affair. It was a random shooting. I didn't find out about it for a while as I'd told myself give it a break for a while to get some sense of myself back. I could feel dependency coming. Turns out I didn't have a choice of breaking it

RIP Ashley