Can I Try? Pt. 02

That kiss was the highlight of my life to that point. Randy, my sexy blonde best and secret crush had kissed me after I had given him a blow job. My mind was reeling and my heart was beating so hard I thought my chest would explode. I was ready right there and then to give him anything and everything he wanted.

A lifetime of shaming and indoctrination wasn't to be overcome that easily though. He threw himself back on the pull out couch pillows with a huge sigh. He was spending the night at my place, the room was still dark and flickers of light from the nearly forgotten soft core porn on TV bathed the walls in bluish light.

"Why can't you just be a girl!" he demanded in frustration.

"Would you like me better if I was?"

"I don't know," he began, "but I would definitely ask you out."

"I would be a girl for you." I said in all seriousness.

"Ha! That would be some trick!" he said.

"Yeah." I replied, my thoughts turning to the girl clothes I had ferreted away upstairs in my room. My eye was drawn to the stairs and I noticed the soft glow of light from the upstairs hallway. My Mom must have gotten up to use the bathroom or something. I didn't want anything interrupting these moments so I ignored it. The possibility of getting caught like this paled in comparison to the potential agony for me of this intimacy with Randy ending.

Here's the thing, I knew my Mom was fairly liberal regarding sex in general. I knew she was pro-gay rights and all that. I knew she was tolerant to being almost supportive of the fact that I liked to cross dress sometimes, but I didn't know how she would react to finding me fooling around with my best friend.

Randy had pulled his PJ's back up, but mine were still bunched around my ankles and my cock was hard again from what I had just done. We were both shirtless and my belly was covered in slowly drying cum from when Randy had fingered me earlier. I grabbed a towel I had laid out early and wiped my belly clean.

When I was done I looked up and noticed Randy watching me in the darkness with a quizzical expression.

"What?" I finally said as he just kept looking.

"You do look like a girl sometimes," he said hesitantly "I mean I'm really sorry, but sometimes it's hard to tell you're not."

I just looked down and blushed. God! Could this night get any better?

"That doesn't bother you does it," he said almost to himself as he brushed a strand of my long dark hair out of my eyes, "me saying that?

"No" I said softly but with confidence, looking him in the eye.

His hand was still on my cheek and I felt it start to tremble. He closed his eyes and his muscles tightened as he had some private internal struggle.

I reached over and touched his chest. "It's OK." I said softly.

When he opened his eyes again he had a determined look on his face that made my breath catch. His hand slid across my cheek and behind my head as he pulled me forcefully into a kiss. He pressed his lips against mine hard. My heart was pounding so I hard I thought I might die.

Then his tongue pushed at my full soft lips. They parted to receive him and our tongues entwined. We were making out! My mind was screaming "ohmygodohmygod" over and over. We were really making out.

My arms went around his neck and his hand moved across my flat belly and the worked its way up to my chest as we frantically kissed. I moaned loudly into his mouth when his fingers found the hard little bud of my left nipple. He started pinching and teasing it, which was driving me crazy. I felt him start to scoot his body closer to mine.

I felt his hard cock through his soft PJs press against my thigh as he hooked his leg over mine. He was thrusting gently against me as he toyed with my nipple and continued to kiss me. My hands were roaming and caressing his muscular back. I was in absolute heaven and I wanted more.

Randy did not disappoint there either, it wasn't long before he was changing his position again, working his way on top of me, unwilling to break our kiss while he moved. He worked his way over my leg to be on top of me, I spread my legs wider and he settled between them. He lowered his hips down and I moaned again when I felt his hard cock, still covered by his PJs, press against my own.

My hands slid down his back to Randy's amazing ass and pulled him even harder against me as I lifted my hips to grind his bigger cock down against my more slender one. Then we were grinding hard against each other, our bodies in this amazing hot motion.

I wanted to wrap my legs around him, but his feet were hooked over the top of my bunched up PJs. This tightened them like ropes around my ankles. I struggled a little; trying to free my smooth legs before finally giving in and just going with it. It was kind of tantalizing how in his power I felt. He was grinding so hard against me now; if I hadn't just cum a few minutes ago it would have been too much.

His grinding was amazing but I could begin to feel the start of a problem, it was starting to burn and chafe against my inner thighs and the delicate skin of on my hard little cock. I wanted to feel his skin on me so badly too. I hooked my fingers into his waist band and started to work them down his hips as he ground against me.

He broke our kiss and focused on grinding into me, his hot breathe and soft grunts in my ear making me desperate to feel his hot skin on mine. I got his PJ's mostly down but they wouldn't go any further. When Randy pulled off of me and sat back on his heels, the problem was readily apparent, the PJs had gotten stuck and the stiff pillar of his erection. He fixed the problem by freeing his gorgeous manly cock and working his bottoms down to his thighs.

Then he was on me again, but this was different. I was hoping to feel his cock pressed skin to skin on mine, what I felt instead was the hot skin of his flat belly. I felt the big throbbing head of his cock press just below my little balls as he pushed himself forward. "Oh god!" I thought, "He's going to fuck me."

"I'm going to lose my virginity, right here, right now." I thought to myself. It was like a dream coming true. I pulled him against me harder. We both struggled with position, driving towards a goal. Then I stiffened. Out of my peripheral vision I saw movement near the top of the stairs.

In that instant I let go and just didn't care. I wanted this to happen, "Let my Mom friggen watch if she wants to." I thought. Hell, I'd watched her fucking her last boyfriend in pretty much the same position while I jerked off at the top of the stairs. I hoped she wouldn't come screaming down the stairs and interrupt us though.

"Is this OK?" Randy asked lifting his body off of me as he misinterpreted my pause with concern in his eyes. I never knew he could be so sweet!

I just nodded as I looked up at his gorgeously lithe muscled torso over me. I reached for the bottle of lotion and put a good bunch on my hand. I stroked his gorgeous cock for a second as I gazed up at him and then pulled him gently toward me, guiding his cock to my ass.

This time with my hand guiding him he was right on target. I felt an involuntary moment of panic as the thick head of his cock started to press against my ass. He was bigger than anything I had tried before, which consisted of mostly my fingers. I overcame it though and lifted my hips to meet him.

"Here, let me just..."

"Should I..." he started.

"Here, just push, OK now." I said pulling his hips toward me.

"Oh God!" he practically shouted it.

"I think I... ohhhhhh!"

The feeling was so intense as he started penetrating me it cut me off mid-sentence. It was amazing but really intense to the point of pain. He let out a grunt as my fingernails, which I kept just a little long, dug furrows that would probably bleed across his back. One more thrust and I saw stars sparkle at the edges of my vision and I was filled with the most amazing full feeling I had ever experienced.

He was completely in me now, buried to the hilt as they say, his hips pressed hard against my inner thighs. We were so close together now, he was deep inside me and also his face was just an inch above mine. We looked each other deep in the eyes as we both breathed heavily adapting to this new experience. We stayed that way for a long time.

Then I started to rock my hips back and forth just a little. I was relishing the feeling of him sliding back and forth in my ass. I was loving this so much that I didn't even register the little bit of pain involved, it was this entire lovely and perfect thing. He started matching my hip movements with small thrusts of his own.

"oh fuck this feels good." He said.

"Mmm oh yes, fuck me." I responded

The pattern was escalating, becoming deeper and longer thrusts. Before long we were definitely fucking. My back kept arching when he would thrust particularly deep and hard and I would moan loudly with no restraint. The flickers of motion continued at the top of the stairs so I was no longer worried about waking my Mom, I was pretty sure she was watching and I didn't care one bit.

The creaks of the sofa bed started to get more pronounced and loud. Pretty soon he was fucking me so hard the whole bed started to shake with the power of his thrusting. He was grunting now each time he penetrated me and his hips made a slapping noise against my inner thighs. I was moaning and meeting his thrusts by rolling my hips. My body seemed to be made for this.

The end table started to hit the wall and add to the sounds in the room. It was like a beautiful symphony of thumps, creaks, slaps, grunts and moans all mingled together with the heat in the room. I was thrusting my hips hard because every time he was all the way in me his stomach muscles rippled and pressed to my aching little cock and it felt amazing. I pulled him closer.

His breath was hot on my ear now as his ass rose and fell, impaling me on his beautiful cock.

"Oh Fuck!" I called out. He kept fucking me.

"Yes Randy, yes oh please yes!"

Over his shoulder I could see my Mom clearly now. Her hands were in her shorts and I could see the front moving as she rubbed herself. Her eyes were closed in pure ecstasy. "Wow," I thought, "she looks amazing." That was weird; I had never been attracted to my own Mom before.

Then her eyes opened and locked on mine. Her mouth dropped open in a silent "Oh" of surprise, but she didn't stop rubbing herself. She must have been right on the edge because the minute our eyes locked her body started shaking violently and she covered her mouth with her other hand. She was cumming.

That was it, next thing I knew my little cock was shooting hot cum between Randy and I, so much our bodies quickly became slick with hot sticky cum. Randy wasn't far behind. A few more deep thrusts then he buried himself inside me and I felt his cock pulsing in my ass as he filled me with his seed.

"Oh god that was amazing!" he said out of breath as he collapsed on top of me. Our bodies were slick with sweat and cum, the whole room smelled of our sex. If my Mom came down now there would be no mistaking what we had just done. I have never been happier in my life. I looked once again over Randy's shoulder to the top of the stairs, the light was out and my Mom was gone. Did I imagine it?

After a minute or two of lying together he finally pulled out of me, leaving me feeling empty. I cuddled up to him, my head on his chest as he played with my hair.

"I think I will want to do this again." he said.

I smiled "Any time you want." I sighed contentedly into his chest. We fell asleep like that, TV on and forgotten.