My Brother is a Crossdresser and I Caught Him

My name is Bethany Green, but I’ve always preferred Beth. I have a twin brother, George, and we both turned 16 last week. Through the early years of our lives we weren’t that close but in this past week we have both grown to want to be around each other.

One day after school I came home thinking that I was the only one in and did what I would normally do. I dumped my bag in the kitchen and ran upstairs to grab my mum’s dildo. It’s a large, seven inches, with a suction cup on the base, which is great.

So I grabbed it, stripped down and got into the shower. I stuck it to the side and with my pussy now aching for it, I pushed myself back onto it. Instantly my back arched up uncontrollably and I was so horny it took me little more than five minutes to cum twice.

Having washed myself down I got out of the shower and because no one was in I dried myself off and decided to walk around naked. Little did I realize but my brother was also home at this point, and as I went to sit down and watch some TV my brother looked up and saw me fully naked. “Oh my God.” And with that I ran back upstairs to put some clothes on. After doing this I went back downstairs and tried to talk to my brother about what had just happened…

“Look, bro, could you just forget that just happened?”

“Sure, sis, aha, just came as a bit of a shock to me.”

“Yeah, sorry I didn’t even realize you were home and, yanno, aha….”

“Yeah, sis, seriously it’s fine. I’ve already forgotten about it.”

“Cheers, bro, you’re the best.”

With that I gave him and quick hug and a thank you and ran back upstairs. Despite how cool he was being about the whole thing I was still horribly embarrassed…

The next day when I came home from school I took the precaution to check whether anyone was home and in response I heard a cry from my brother shouting, “Don’t come in here, don’t come in here.” My brother and I were now fairly comfortable with each other and so normally I would just assume that he was masturbating but the surprise for me came when I realized that the shout was coming from my room. Deciding to go against his cries I ran upstairs as quickly as I could and opened my door…

What I saw was my brother fumbling to get one of my skin tight dresses off of him. With it half off, the tights, bra and panties of mine were also revealed. After realizing that he was surprisingly tall I looked down to see him wearing a pair of my six inch heels.

I stood there in shock and so did he; neither of us moved at the sight of him. The worst part was that since I got there he had developed a giant erection. Having not seen my brother naked before I had no idea how big his dick was but those tiny panties couldn’t contain the eleven inch monster that he had been hiding away.

“Look, Beth, I can explain. I love you, not just as a brother but sexually. The idea of wearing your clothes just turns me on even more. Do you feel that same?”

“Well, no. You’re my brother, that’s weird, and illegal, but your dick is huge.”

“I know, I’m quite proud of it, sis. Please, just try it, just let me kiss you?”

With that, even before I could answer my brother was advancing towards me. Too stunned from what I had heard to move I just let him and soon he was placing his soft tender lips upon mine. I kissed him back, but the moment he pushed his tongue past my lips I pulled back, trying to tell him that it was wrong. My brain knew it was wrong but for some reason I pulled him back and started wrestling his tongue with mine. It was the best kiss I had ever had.

With that I decided that if we could kiss we could do anything, and said to him, “If you’re going to dress in my clothes and be a sissy then I’m going to dominate you.”

I grabbed his dress-covered ass and slapped it. I continued to kiss him passionately and slap his ass. I’d just realized that under the bra he was wearing he had breast forms in, only making me think that he must have been doing this for a while now and really wanted it.

After around ten minutes of passionate kissing and me slapping his ass and feeling his breasts, I stopped and decided if we were going to do this, we were going to do it properly. I told him to go into his room and wait. About five minutes later I brought him my favourite lingerie set; it was a red lacy set, with a slight padding in the bra and a garter. On top of that I gave him a skin tight black dress. I left him with some six inch black heels and a bag of makeup and told him to be ready in half an hour. I was going to have some fun with this…

When half an hour came I walked into his room similarly dressed up, pushed him onto the bed and told him he’d better be ready to be dominated. I straddled him and kissed him passionately on his soft tender lips and all around his neck. Whilst doing this I began caressing his breast forms and slowly grinding over his crotch. With that I jumped of the bed and told him that he was to do a strip tease for me.

The idea and picture of him slowly pulling of those clothes was already getting my pussy soaking wet. I told him to bend over and without any warning I began to lick his naked asshole. I got it so wet and slippery that I brought one of my hands up and slipped two fingers in and started finger banging his arse.

It was so hot and he was crying out with pleasure. I slowly began to strip, trying to keep my tongue and hence my mouth firmly planted on his soft tight ass. He turned around when I stopped and his jaw dropped as I was stood naked to reveal what I had been hiding, a giant nine inch black strap-on. It would be its first use and he was ready for it.

I grabbed a bottle of baby oil and squirted it all over him and the strap-on making sure everything was properly lubed up. The first entry was difficult as it took him a while to loosen his asshole even with all the lube. But once it was even I began with long and powerful, yet slow, strokes in and out of him.

He was beginning to move with the dildo, pushing back on it as it went it. After about ten minutes of this it became apparent that neither of us was getting any real pleasure so I took off the strap-on and ordered him back to the bed for me to sit down hard on his face.

The way he licked my pussy was heavenly, the idea of my brother licking my pussy was a feeling I had never felt before and it was incredible. He went back and forth from flicking his tongue over my clitty to jamming it as deep as he could into my aching pussy.

After at least four of the most intense orgasms I had had in my life I began to realise that I hadn’t done anything to please his dick yet. So I got up off his face and turned myself around into a 69 position with him. It was only about three minutes before he came rope after rope of smooth warm creamy cum all over my face. You could tell he was horny because those three minute were the longest of my life.

It didn’t take long for him to get hard again after that and as soon as he was I leapt back on top of him and rammed my still soaking wet aching pussy down onto his rock hard and perfectly sized eleven inch dick. Every single thrust was hitting my g-spot and making me scream out with pleasure…

“What the hell are you two doing,” said my mum.

To be continued soon…