...Slowly

You hear lube being applied so something, and she says with a soft moan, “Okay hon, here we go”

And you feel the head getting pressed against your hole, she slowly circles it as you feel lube being smeared on your hole and then pressure as she presses it against your hole, she has one hand down below your skirt and you can’t see anything, she is on top of you, like how you would imagine being on top of a girl missionary style, she has your knees pinned against your chest while she uses one had to support herself and another working the dildo on your ass.

You look up on the borrowed canopy on the bed to see her leaning over you your dressed up like a girl, it’s almost like watching a guy fucking a girl instead of her working you.

“Okay, just relax and breath hon”

Then you feel it press against you’re hole and start to push e is pain involved, like when you try to push out a massive log,

You gasp, “oh god”

She stops and then pulls out and then proceeded to circle your hole with the warm hard of the dildo which eases the pain slightly.

“That’s it hon, just relax, let me know when it stops hurting”

You nod, the pain quickly subsides and you say “It’s okay now”

She smiles and slowly starts to push it in again, you feel it glide in some and it takes a bit more before you feel that pain again and gasp a grunt as it starts to hurt.

She stops and slowly pulls it out again “See hon, that was quite a bit further this time” and she slowly massages your hole with that head as the pain starts to dissipate.

She leans in and kisses you with that deep kiss your totally relaxed “I’m so happy I get to be your first, you promise you’ll Sex with me when we’re done here?”

You nod, you can’t think of anything that would stop you from having sex with her, you wanted her the second you saw her. “Yah I promise” Such a stupid question, why wouldn’t you want to have sex with her?

Then you feel it push inside of you again slowly, the warmth, the discomfort, you feel it slide, it makes you grunt slightly, but at least it isn’t the sharp pain, the slimy lube and the sensation of it gliding through your hole, she says with a soft moan “oh baby, it’s in now, you feel so damn good”

You think that’s odd, she knows how to turn you on, that’s for sure, you see the porn girls talk like this with toys, how good it feels, but you guess she is roll playing, like she is the one fucking you.

She stops and the pain and discomfort is still there, she doesn’t pull it out but you feel it subside a little bit.

She says softly, “that’s it, relax, your so tight, we’ll get going in a sec, I’ll let you relax a bit.”

It felt warm, the texture your amax]zed that you can actually feel it, warm, firm and yet the texture feels silky and soft, these toys are amazing you think “WOW, it feels kinda nice, but it still hurts.”

You wonder if it’s your ass gripping it because the throbbing sensation as she says in a satisfying tone “Oh hon, we’re going to have the best sex of your life, we’re going to fuck each other’s brains out”

She wasn’t shy about her words and you’re heart is racing even though you got a toy in your ass, she starts pushing in more and more, it starts to hurt some more and you gasp and grunt a little, as she says, “that’s it hon, just relax and breath”

Then you feel her skin and pelvis press up against your ass, and she says, “There all in now” you glance at the canopy mirror and then notice something next to her hip laying on the bed, you blink twice and look at it, it’s the dildo, the you say “What the hell?”

You glance down beside you to see it laying there, and then hold the skirt down flat to see what’s going on, she leans up so you can get a better look to see her pelvis pressed up against your ass cheeks, “What?”

She says in a satisfied tone, you are so fucking tight, and you feel the cock throb as she talks”

“Is that a, a, strap-on?”

She chuckles slightly and you feel the cock respond, the warm thick cock, “No baby, that’s all me, she pulls out slightly so you can see it is indeed a thick cock” your eyes widen “what the fuu..”

She smiles, “I’m a tranny hon, and your going to have the best sex in your life”

“A what?”

“Tranny, I’m a T-girl” as she pushes back into you.

Your so fucking confused, this hot chick has a dick? What’s inside of you right now? You don’t even know what to think, the pain starts escalating as you try to move your leg which seems to snap her out of that sexual haze she was in “Whoa, baby, slow down, you tightened up on me pretty hard, relax, you start grunting because it starts hurting more, “Shhhh, relax, just relax”

“What the hell? What’s a tranny, your a girl or what the fuck?”

She leans in to kiss you to calm you down your eyes are wide, you are so confused.

She says “baby, you promised, you said you would have sex with me”

“Well, yah, but, I..” you don’t know what to say, she buries her mouth on yours to calm you down, it took a little bit but her tongue working yours got you focused on her mouth instead of on whatever it was in your ass.

She finally pulls off of your mouth, “That’s it just relax, shhhh, relax, let me finish, and I promise all those things we talked about are going to happen.”