Stacey's Brother

"I'm sorry," he whispered.

"F-For what? You didn't do anything..."

"I know," he said. "But, I hate my sister for doing this to you."

Then I felt him press his lips to my neck and kiss me gently, as his hands began sliding up and down over my chest, in a soothing manner. I felt...comfortable. Relaxed.

"This isn't so bad," I admitted, out of nowhere.

"You think so?"

He sounded surprised.

"Yeah, I mean...it's not something I ever expected to have happened. But it's not all that bad. You look really good as a girl, and it's almost like I could forget that you're a guy."

Alex smiled behind me, kissing my neck again. Considering how attracted to me he had always been, I was sure what I just said was probably like music to his ears. "Tell you what," he spoke softly. "If you wanna...give me a chance...I'll keep dressing up, and we can act like I'm not a boy at all."

I laughed at that, and so did he, but he carried on in a serious voice. "I mean it. The only condition is, I'm not going to go by my sister's name anymore."

"What should I call you then?"

"Just keep calling me Alex," he answered.

I didn't see the harm in that, I thought...Alex was often used as a girl's name, so it could work. And if he kept dressing as a girl, then it might be easier for me to get used to all of this.

"Now," Alex said, breaking my train of thought. "Do you wanna...play around a little more, maybe?"

I blinked, as his hands continued to explore my chest, fingers occasionally teasing my nipples. I could still feel his warm breath on my neck. What else could we do? Suck each other off again? That must have been what he meant, I assumed.

"What did you have in mind?"

"Oh, I don't know," Alex shrugged. "Maybe I'd like to put something a little bigger than my finger, in that cute little butt of yours?"

"Uh...w-what?"

"My dick would fit nicely, I think, don't you?"

"Whoa, wait a minute," I laughed nervously. I pulled myself from his arms now and pushed myself onto my feet, looking down at him and rubbing the back of my head.

"I-I don't know about that one, Alex...I'm not sure if I can do that."

"Why not," he asked, stroking his dick now.

"I let you fuck my ass, isn't it only fair that I get a chance too?"

"Hey, you decided to let me fuck your ass...I didn't ask you to let me do that, you offered."

"True. But think about it, Matt...I mean, you seemed like you enjoyed my finger, didn't you?"

I blushed but did not answer.

"I know you did," he smirked.

His hand was still sliding up and down his cock, which was now standing at full attention again...it was fucking throbbing this time. It looked even harder than it had a few minutes ago when I was sucking him off. Just thinking about fucking me in the ass, seemed to have such a big effect on Alex, he looked like he could barely contain himself.

"That was just a finger though," I answered finally.

"I mean, the actual thing is...kind of..."

"Intimidating?"

I simply nodded, and Alex laughed. "I can understand that...the first time I got fucked, I felt that way too...but the guy I was with took it nice and slow, he was gentle with me and made sure that I was comfortable and I enjoyed myself. I would certainly do the same for you, Matt."

I looked at his throbbing member again, biting my lip, as I mulled over the idea of actually giving this a try. I had already sucked his cock, so my curiosity was starting to rise a little.

"Tell you what," Alex said suddenly.

"Let's go to my room...maybe I can break you in a little, and make it easier for you to take the real thing."

"Break me in?"

Instead of explaining, Alex simply stood and took my hand, leading me up the stairs and into his bedroom. I had been in there a few times before, during my relationship with his sister.

Alex and I would often play video games together, or just sit and chat with each other, whenever Stacey was busy or if I was waiting for her to get home from work. This time was different though...I had never expected to find myself walking into his room, to do anything sexual with him.

As Alex closed the door behind us, he pointed towards his bed.

"Go lay down," he said softly. "Flat on your stomach."

Reluctantly, I started slowly across the bedroom floor and climbed onto the queen-sized mattress, laying flat on my stomach as he had instructed. I heard Alex digging through his closet for something and finally, he emerged with three items...a bottle of lube, a vibrator and what looked like a butt-plug. "Let's just loosen you up a little," Alex said.

He sat down on the bed next to me, and popped open the bottle, squirting some of the lube into the palm of his hand and then picking up the six-inch dildo. He rubbed the sex toy, getting it nice and slick with lube, before grabbing the bottle again and squirting some additional lubricant onto my ass.

I felt him rubbing it all over my ass, making my cheeks glisten and making sure to get my virgin hole nice and wet too.

Then I felt him press the tip of the sex toy to my entrance, pausing for a brief second, before pushing it into me...I gasped, gripping the sheets tightly, as the head popped past my sphincter. The dildo wasn't very big, nor was it very thick for that matter, so I found it relatively easy to take.

There was a bit of pressure back there, but it was tolerable.

The second Alex began pushing the toy deeper into my hole though, I felt myself starting to shake a little. I could feel my hole stretching as it tried to accommodate inch after inch of the toy until finally, Alex was pumping it in and out of me, fucking me slowly with the rubber cock. "How does that feel?" He asked, curiously.

"N-Not...too bad," I replied.

I was still gripping and pulling at the sheets slightly, but not in pain, just pleasure and anticipation. Alex spent a good couple of minutes playing with my ass and the rubber toy, stimulating my prostate with it until my cock was dripping with pre-cum all over his mattress.

I didn't even notice when he pulled the toy out of me and replaced it with the vibrator until he flipped the switch and it began vibrating.

"Holy shit," I gasped, startled by the strange sensations.

"Hehe, relax sweetie...this is going to feel good," Alex assured me, as he began sliding the vibrator in and out of me now.

It was on its lowest setting, but already, I could feel it working its magic on that sweet spot deep inside of me.

Confident that I was enjoying it enough at this point, Alex flipped the switch to the second set, and the vibrator began to tremble a bit more intensely. I could hear the low hum coming from it, as Alex pushed it deeper into my asshole and I gave a low grunt, slumping forward on the bed and burying my face in one of the soft pillows.

He started moving the vibrator in and out of my ass now, fucking me with it and flipping the switch a third time, to its highest setting.

As it pressed firmly against my prostate, my eyes went wide and I tried to moan, but the sound got stuck in my throat and I wound up holding a deep breath of air until my cheeks began to flush red. Finally, I let it out and gasped for air, moaning much louder now, as Alex slowly withdrew the vibrator and switched it off, setting it down on the mattress beside us.

"I think you're ready now," he said, smacking me on the ass and shifting behind me. "Are you, Matt? Are you ready for my big cock?"

"F-Fuck...yes," I groaned, my prostate still singing with pleasure from the vibrator.

Alex moved behind me, spreading my ass cheeks wide and shoving his cock straight into me, bottoming out almost immediately. He showed no hesitation, just going right for it and taking what he wanted.

I was loosened up just enough, that he didn't have any trouble and I did not experience any sort of pain or discomfort from it.

"Holy fucking...shit!" I cried out, as he sunk balls deep into my ass.

That felt WAY more intense than anything he had stuck up there, up until this point. It was better than his fingers, better than the vibrator...it was way better than the dildo, even. It was the real thing, and god damn, if I wasn't already falling in love with dick...I certainly was now.

"Fuck me," I groaned, as Alex pulled about halfway back and then proceeded to throw his hips forward again.

He pulled back more, rolled forward again, and repeated the same formula over and over again, all the while making me gasp and beg for more. It didn't take very long before he had me moaning like a total bitch, pounding my ass with everything that he had, sweat pouring down his back as his balls smacked against my perineum.

Alex gave a warning, that he was almost ready to cum...he could feel it in his nuts, as they tensed up and his cock began to pulse, before erupting like a volcano inside of my ass.

Grunting and moaning and panting heavily, Alex dug his nails into my hips, leaving marks from his fingernails as he buried his cock as deep inside of me as he could manage. I felt the warmth of his cum flowing into me, filling me until he had completely emptied every drop of cum from his balls.

And then he collapsed on top of me, pushing me firmly against the mattress, his cock still throbbing inside my ass, as he started kissing my neck, and sucking at it, trying to leave a hickey as his mark. "I've been wanting to do that...for a very...very long time now," Alex laughed, still trying to catch his breath.

"Was it worth the wait?"

He slowly withdrew his cock from my ass, laying down beside me and I turned over onto my back, his arm sliding underneath of me and pulling me closer to him. "Oh yeah," he said, kissing me on the lips.

"It was fucking worth it, baby."

It was worth it to me too, to give it the chance that I had.

Who knew I would enjoy everything we had just done so much, right? After that night, me and Stacey made up...sort of...I was fine with the fact that we were no longer together now, and that she had moved on, and I was moving on to.

I tried hooking up with a couple of different girls after my night with Alex, just to confirm what I had already been thinking...that sex with women, was nothing compared to what I had experienced with him. I had never been with a girl in the past, or after my first gay experience, that had ever made me feel as good as Alex had.

And that included his sister; no way in hell, could Stacey compare to her brother and his skills in the bedroom.

So I took the offer that Alex had made earlier that night...we continued to meet up, long after that one occasion, and have sex regularly. Alex dressed as a woman every single time that we did, and the more he did it, the better he seemed to get at it.

We weren't dating at first, just fooling around, but after a couple of years, we decided to start a real relationship.

It's been ten years since we first had sex together, and eight years that we've been dating...I'm glad that Stacey dumped my ass because if she hadn't, I never would have met the real love of my life.

Stacey's sister.

Alex.