My Sister, My Teacher Ch. 05, again

Thank you for kind words. This one has been fun to write. Similar to my other stories, but different, too. I have an idea for another twist, if this story is well received. Thanks, again!

He came 3 times, that night. I was in heaven, being able to give my best friend what he needed for so long. (AND, fulfill my desires in the process) The worry over him freaking out on me, or having regrets later, was unfounded. He was coming, (and yes, CUMMING) at my house daily now, and his shyness was fading. He seemed to walk taller, and smile more. My sister and parents had to know, but said nothing. Well... my sister and Mom, gave me knowing smiles and winks, and, I swear, Dad was drinking me up, every time he saw me. I was now on estrogen shots and pills.

One day, starting into my third week as my feminine self, Janine pulled me into her room. "Little sister, I know you are loving your new sexuality, sapping the essence out of Matt, but, girl, you need to think about phase two." I gave her a blank look, then realized what she was saying. The thought had crossed my mind, I guess, but I figured it would happen eventually. She threw me a bag, and said, " You'll need to start cleaning (grinning as she said that) your pussy, Hon, and um, preparing it. Cocks fit in mouths much easier than that tight little hole men crave. And trust me, girl, I've seen enough looks to know, they are craving that sweet ass of yours. The strut of yours is attracting attention, and, if you don't already, you'll be wanting to give it to them. Hell, even Dad is tripping over himself, trying not to stare." She saw my surprise. "What? He's a man, full of hormones, girl. Mom sees it, too. She says he's wearing her out since you became Geri. She's happy for the attention, but isn't sure she can keep up. SO, back to the point, you need to be thinking about losing your cherry." She laughed out loud over that.

She then pulled out an enema bag, and, despite my embarrassment, explained how to use it. Next came a dildo. Not a big one, like in porn videos, but obviously bigger than anything I might think of putting inside me. And a tube of lube. I picked it up, questioningly, and she said, " trust me, you'll want this. Now, get yourself in the bathroom, and start experimenting." Like a good sister, I got up, and marched to the bathroom, undressed, and slowly, and awkwardly, learned how to use the enema bag. Though very weird, it wasn't at all what I imagined. The warm water felt sensual, and I knew I'd be using it a lot. I wrapped a towel around me and went to my room. I examined the dildo, and fingered some lube in my star, (again weird, but intriguing), and some on the head of the dildo. I laid on the bed, pillow under my hips, and positioned the dildo at my opening. I just pressed it against me, at first, rubbing it around, imagining that it was Matt. A thought came to me: A few times lately, as Matt lay on his back on the bed, and I lay, in kind of a 69 position, next to him, as I sucked his cock, his hand would wander down my back, on my ass, and caress my thighs, and ass. I loved him touching me like that, but never got the connection, before now. Maybe he WAS thinking of fucking me!

I closed my eyes, and picturing Matt on top of me, his cock at my boi pussy, pushed the dildo in me. WOW! Strange, yes, but in good way. I whispered Matt's name as I fed the dildo in more, and started moving it around. In my head, it was so easy to "feel" that it was Matt, making me a woman. I was twisting, and fucking myself with that rubber "Mattstick" and trying my best to stifle my moans. If this is anything like really being fucked, I'm in! My clit was leaking, I knew I was close to cumming, and fucked myself as hard and fast as I could. I shook hard, and cum shot up to my chin, as I writhed. Holy shit! I needed a shower, I was soaked in sweat. What a new revelation. As I showered, I imagined Matt behind me, filling me with his cock, and cum. I pondered for a moment, could cum be some kind of magic elixir? It certainly had me hooked.

When Matt came over, I almost immediately dragged him to my room. I unzipped him, pulled down his jeans, with his boxers, and pulled them off him. I pushed him back on my bed, and assumed my usual pose, in the 69 position. I made sure that my skirt was riding up on my ass, and the thong I was wearing was tiny, nothing more than strings on my cheeks. As I stroked and sucked him, I would twist my hips, and open my legs a little wider. I mostly teased his cock, not wanting him to cum too soon. Yes, he could cum several times, but tonight, I wanted all of them to be in my ass, not my mouth. My patience paid off, before long, his hand started drifting, off my neck, shoulders, down my back. When he reached my ass, for the first time ever, he eased my skirt up, and I felt his bare fingers caressing my round ass. I moaned on his cock, and wiggled my butt. I whispered, "That feels soooo nice. Do you want to... take my virginity?" (All the time holding my breath, hoping for a yes)

He looked a little surprised. "A-are you... sure you... WANT to... umm, DO it?"

I spun around, hugging him. " I want it to be you, Matt. And, yes, I want you to, very much. It can be another first for us." I gave him a long, slow tongue filled kiss, something we had only done a couple of times. His cock, beneath me, had never been harder than right now. I rolled off him, smiled and asked, how he wanted me. On my back, or on my hands and knees. I reached under me, and pulled my thong to the side. He'd never said anything about my "clit", but I wasn't about to expose it, and ruin the mood. He was already shaking.

His voice was quivering when he cleared his throat and said, "

Umm, m-maybe on your hands and knees this time..... IF you are sure. You look so damn sexy that way"

I kissed him, and got on my hands and knees. I wiggled my ass a little, hardly able to hide my desire. I was about to be fucked like a girl, for the first time. The dildo was amazing, but it was half the size of Matt's cock, AND, I couldn't wait to feel his cum inside me! I reached over to my nightstand, grabbed the tube of lube that was partially hidden. "We will... probably need this, ok?" He nodded, took it, and rubbed some on his cock. He couldn't have known that I already had put a little inside me, just to be safe, so that he would go in easier.

I held my breath as he cautiously moved closer, and put his cock on my star. "Your ass is... SO damn sexy, Geri. I... I've thought about this, but didn't think you'd want to go this far." with that, he took a deep breath, and pushed...

"Oh, God!" The second his head slid in me, I almost came. He froze, and asked if I was ok. "B-Better than ok. Ohhh, Matt, don't stop..." I could feel his cock throbbing in me. That must have given him confidence, because he buried that warm, smooth cock inside me!

iMy eyes rolled back in my head. YES! If I EVER had any doubts about becoming Geri? They were gone. Sex as a boy could NEVER have come close to this feeling. "Oh, Matt, FUCK me!!! You feel soooo amazing in me!"

My head was spinning, I think he was saying something similar, but my body was overriding my ears. All it wanted was more of this! I bucked back against him. As he thrust into me, I would back into him. My "clit" was dripping on my blanket, and I could care less. I struggled to keep from screaming his name out, but didn't want Dad bursting through the door to find Matt deep in me. Meanwhile, Matt was moaning louder, his hands on my waist, telling me he's cumming. Don't let anyone lie to you. You FEEL that hot blast fill you. The most glorious feeling humanly possible! I was non-stop cumming, and, thank God, Matt did not soften as he came, but kept on pistoning inside me. At THAT moment, I wouldn't have cared if Dad DID come through my door, I wasn't stopping Matt. My wet hair hung around my face, my tank top was glued to me by sweat, and I'm sure Matt was as hot as me, but we didn't stop until he came again, and collapsed on top of me, gasping for breath. He was still inside me, and slowly softening.

After a couple of minutes, He slid off to my side, and whispered in my ear, "I didn't know what to expect, but, FUCK! That was unreal. Geri, you are DEFINITELY a sexy woman. I don't think it could have felt like this with anyone else. W-when we... started all this... I had my doubts. You know, when you... first went down on me, but Damn! You are SO fine, and, bonus? You can't get pregnant!" (Huge laugh)

I hugged him and smiled. "Definitely takes "best friend status" to a new level, huh?"