Stepping into It Pt. 02

How intoxicating, sharing Jared's creamy cum between us, moving my tongue deep in his mouth, having him move his tongue deep in mine, the salty, musky taste of him exchanged between us. He was sweetly, tenderly, caressing my ass through my panties, with my ever so hard cock pressed between us, rubbing up against him as I slowly rocked my hips into him, my hands now gripping his ass, pulling him toward me.

How I wanted this feeling to last forever. And yet, I knew that there was even more delicious passion in my future.

Then he whispered in my ear, "Ohh....thank you Ty, that was so good. I love the way you suck me, and I love the way you look in those panties, stockings and bra. You are so feminine and you can show your excitement so well."

He nibbled on my earlobe as he grasped my hard cock in his strong, hot hand.

"Yes, Jared, God.....that feels so fucking good....I'm so horny. Do you really like the way I look in lingerie? This is my very first time and I already love being dressed like this......and for you too!" I whispered back, loving that I could make someone so desirous of me.

Jared certainly did want me. I could feel the tip of his cock touching the top of my leg as he began to get hard again. And of course you know what I wanted as well. I wanted Jared to slide his hot cock into me, deep into my ass, fucking my virgin ass hole.

"I have an idea Ty. Leave your panties and bra here in the laundry. Leave on those stockings...." he whispered as his hands now caressed my thighs, sending a shiver through my already steamy body "and let's go up to my bedroom, I have something there that I think you'd like."

I had no doubt that I would like whatever Jared had in store for me. How could I not? Our time together had been so fucking hot. Though now the thought that flashed through my mind was 'what would my Mom think about this?' Then, as if reading my mind Jared said,

"Just to let you know, your Mom and I have an arrangement. She's OK....well we're both OK..... with certain amount of exploration. And I know that she'd be OK with what we're doing now."

Well, that was interesting, and certainly raised a few more questions that it answered, but this was not the time for a conversation about such things. I felt relieved and curious at the same time. Had they spoken about this possibility? My Mom was certainly aware that I tended toward the feminine side of the spectrum, did she want Jared to be the one yo take me? Who knew?

All I knew right then we that I was as hard as I've ever been in my life and my fucking hot stepfather was following me up the stairs, his eyes glued to my round ass, my balls dangling so enticingly between my legs. The stockings wrapped around my legs felt so good brushing against each other as I climbed the stairs.

"Like the view?" I asked teasingly as I swayed my hips.

"Ohh..my God....." was all Jared could say.

Making it to the bedroom, (that I had been in so many times before, but now felt so different) Jared beckoned me over to his chest of drawers. He opened the bottom drawer, revealing a treasure! A collection of panties, garters, corsets, chemise, camisoles, stockings......the works. Satin, lace......especially the lace...it was so attractive to me...I audibly gulped as I saw it there. To top it off there were a few dildos, butt plugs, and other items which I couldn't even identify the purpose of.

"If you don't mind Ty, would you put this on for me?" he asked, holding up a corset with an integrated garter.

The corset didn't have any cups but did have straps, and I had loved the feelings of the straps on my shoulders. It was a deep green with black lace trim, black garters, and purple ribbon to pull it tight. I immediately thought of how it would push up my tiny tits and leave them exposed to Jared. With that in mind I unconsciously stroked my right nipple with the nail of my right index finger as I gazed at the garment in front of me. My cock jerked with the stimulation.

"Ohhh....Jared....I don't know what to say....of course I would! I would wear whatever you'd like to see me in." I replied, feeling like an excited girl. One who now knows she can excite a man. Knows that she is the object of that desire, making him hard, so hard that he stood straight out and slightly upward, as Jared was right now

"And would you put this on?" he asked. Holding up a pair of sheer black panties with lace trim. These panties had a pouch in the front, but were open in the back!

"Ohhh.....my Jared.....these look like just what the doctor ordered.....I would love to put these on for you."

"Put the panties on first, and then the corset."

So, I did. I put the panties on and then pulled on the corset.

"Here, I'll tie this for you" he said, helping me with the corset, pulling the ribbon tight. And it did have the effect of enhancing my breast, making me so happy!

"And I'll help with these...." he said as he got on his knees to clip my stockings in place. As he did so I helped with a few of them, to get the hang of it from someone who had clearly done this before.

Of course, as he was on his knees in front of me he couldn't help but squeeze the very hard cock that was sticking out into his face. And he gave my slit a lick with the tip of his tongue, as he could see that there was some liquid oozing out of it. And as I turned to allow him access to the back clips, he cupped the bottoms of my cheeks in his strong hands and gave them a firm squeeze, pulling them apart as he did so.

That task accomplished, he rose to his feet behind me, his fully engorged cock now feeling so hot as he pressed into me and it throbbed between my cheeks. I instinctively thrust my hips back to get more pressure and began slowly rotating on his shaft. He pulled me toward him by the hips and then moved his hands up to feel my nipples.

"Your nipples are so hard Ty," he whispered in my ear as his finger tips began to squeeze them.

"Do you like that Ty? Do you want me to twist them?"

"Ohh......god.....that feels so good. Yes..Yes...twist them Jared. squeeze my tits and twist my nipples.....please..."

Jared increased the pressure and twisted my nipples and......I loved it! I loved

that combination of pleasure and pain that it evoked. It made me press my ass back harder against his pole, writhing against it, as he began to rock his hips sliding himself up and down my cleft, the slick film of sweat lubricating the movement. He moved one hand into my panties to grasp my cock and kept the other on my tit as he started slowly stroking me.

The feeling of the corset binding me, the sensation of my stockings moving against his legs, the pleasure and pain of his fingers.......a taste of heaven right here in my mother's bedroom.

"It's time Ty. I want to fuck that sweet ass of yours. I want to cum deep inside your virgin ass. Would you lie that Ty? Do you want to feel my cock inside you?", this was music to my ears!

"Of course Jared. You must know how much I want you to take me. How much I want to feel your hot shaft inside me, inside my pussy."

Jared moved back away from me now. He reached over to the dresser and grabbed a tube of lube and then reached down into the drawer of delights and brought forth a slender dildo. A simple white plastic one with a slight bulb on the end. Honestly, since I'd been watching gay and crossdressing porn I had tried out a few items on myself already. I'd been having a brief affair with the handle of the toilet plunger. So, this was not entirely new territory for me.

"I think that you should start with something a little easier Ty, something to pave the way. Would that be OK?" he asked, fondling the dildo as he spoke.

"Yes, of course, I........I imagine that you know best." I stammered.

"Good, now bend over with your arms on the bed." he directed.

Of course I did as I was told, my willing ass now up and ready for what was about to cum. As Jared first used a finger to probe my willing opening, the feeling of him sliding into my puckered pussy was nothing but delightful! There was no pain as he moved his finger in and out, greasing my hole.

"Uhmmmmm.....that's nice Jared....so nice...."

"Good Ty...this next might hurt a bit

So he then pressed the bulbous head of the dildo against my asshole and slowly pressed as he reached around with his other hand and gently stroked my cock. To my delight the dildo readily popped into my open and wanting chamber.

"Ohh, yes Jared, I love it...." I moaned, as he began to work the dildo in time with his stroking my burning shaft.

After just a few minutes of this he pulled out the dildo.

I knew what I wanted right then. I knew I wanted to see him. To look into his eyes as he took my virgin ass. So I stood up, turned and lay down on the bed.

"I want to see you when you fuck me Jared. I want to see the man who gets to fuck me for the first time."

"I love that Ty. I want to see you as well. God......you look so sexy Ty!"

Jared put a pillow under my ass to prop me up. I spread my legs to invite him in as he approached me, my feet flat on the bed. He began by coming up to kiss me deeply, his tongue dipping into my waiting mouth, our hard cocks pressing into each other as he moved his hands down to cup my ass cheeks. My legs instinctively rose skyward as we pressed into each other.

Then I knew it was time. My hand found his hot cock and brought it to the lips of my boy pussy. I slid it around the opening, making little circles around the sensitive rim, his precum adding to the slick sensations. He pulled himself up above me so that we could look into each others eyes.

"Are you sure you want this Ty?"

"Ohh....god yessss. I want this. I want you to fuck me with your hard cock Jared. I want you to be the one to take my virgin pussy. Please fuck me!"

And with that Jared slowly moved his hips forward as I guided his slick shaft into my ass. I was so open and ready that, as his head popped in, it wasn't nearly as painful as I thought it might be.

"Ohhhh....fuck yes Jared.....Ohhh.....slide it in further!"

Jared and I looked each other deep in each others eyes as he slid himself deeper and deeper into my fuck hole.

"Yes...yes....yes...", was all I could say as he penetrated me.

My legs were now wrapped around Jared's waist as he began to lift my ass and move in and out of my tight pussy. He was so strong and I loved it! He increased his pace and depth as he began to fuck me hard, the sweat pouring off of us both as I rose to meet his deep thrusts.

"You have such a sweet, tight pussy Ty. I love fucking you....Ohhh...yessss"

Jared lowered himself onto me so that my boy clit was being pumped by his thrusting. His hands were on either side of me. My fingers dug into his back as he entered my mouth with his tongue. The sensation of having both his tongue and cock inside me was so good!!

I knew I was about to cum, I could feel it building deep in my balls. Jared knew it too.

"That's it Ty, cum for me. Cum hard!!", he said as he pumped me with that long rock hard shaft.

"Oh.....God.....I'm cumming Jared....OHHH....FUCK.....YESSSSS!!!!!!, I yelled out as I shot my cream between our writhing bellies.

With that, Jared rose up and raised my ass with his powerful hands. Half my body was in the air, with my legs over his shoulders as he penetrated me to the core, his gaze filled with both lust and love as he went as deep as he could inside me.

"Yes.....Jared, fill me up, fill me with your hot cum, I want it so bad......fuck me....fuck me.....fuck my ass......"

"Yes Ty......this is for you.....I'm cumming!!!!!"

I could feel his cock spasm deep in side me, and the heat of his cum fill me as he continued pounding me, releasing as much of his cream as he could.

As he began to slow his thrusts he gazed upon me with such tenderness that it brought tears to my eyes. The emotions came on now as I wept with him inside me.

"Oh Jared, that was the most beautiful thing that's ever happened to me. I love being a girl for you!"

Jared reached down and dipped his finger into the cum that was on my belly. He licked his finger and smiled warmly.

"I love that you're also part boy Ty."

He lowered himself onto me and kissed me deeply, the taste of my cum now shared by us. He pulled out and lay next to me as we continued kissing.

When I awoke Jared was out of bed and had showered. How long had I been asleep? He nudged me and said, "Wake up sleepyhead, your Mom will be home soon."

Wow, yes, my Mom. What to say to my Mom?........I knew right away. I had to be straight with my Mom. I had to tell her everything; how much I had been fantasizing about sex with men, especially crossdressing men; how good it felt to wear lingerie that day; how much I wanted Jared to take my virginity; everything. This was now part of my life, there was no going back.