“Hey sis, look what I’ve found.”
It is the beginning of the summer holidays, and I am sitting on the edge of my bed contemplating the realisation that in September I will be going to University and my ‘little’ brother, Robert, will be in his final year at school.
I look up to see Robert standing at the door to my bedroom. He repeats, “Look what I’ve found.” As he walks into my room, he drops half a dozen magazines on my bed and then sits next to them. I glance at the covers that have pictures of sexily dressed women on them, except one that portrays a girl in a fantasy ‘little girl’ dress. The magazine is titled Sissy News. Looking at the other titles, I realise that all the magazines are about crossdressing. Robert pushes one of them towards me.
“You might like this,” he says.
I pick it up and start looking at the pictures inside. All of the men, some very pretty, are dressing in female undies. Lots of stiff cocks thrusting sheer panties forward, French knickers being pushed upwards, stockings caressing pale thighs. The stiff cocks cause me to get very wet. I glance at Robert, by the way his shorts are bulging, he too is being turned on. Looking at the projection in his shorts, I suddenly realise that my ‘little’ brother is not so little after all.
“Where did you find these?” I ask.
“I managed to unlock the bottom drawer of the desk that dad used, in the utilities room.”
“Is this all there was?”
“No, there was other stuff there as well.”
“Like what?”
“Clothing.”
“Really, let’s go and have a look.”
With that, I drop the magazine I’m looking at and head for the door. I notice as I leave that Robert’s shorts are fully stretched, and, I suspect, he is glad he is following me, so I can’t see how stiff he is.
In addition to the desk in the utilities room, there is a washing machine and a tumble dryer. Opposite them is a small sofa, with the desk between. Opening the bottom drawer, I see a couple of boxes and a froth of female undies. Bra and panty sets, a sheer nightie, a baby doll nightie, and some satin pyjamas. Three garter belts and lots of stockings, some still not opened. A black satin maid’s outfit with a frilly petticoat: satin slips and a corset.
“Goodness,” I say, as we spread all these items on the sofa.
“So, this was what dad was into when we thought he was working in here.”
“Guess so,” says Robert, as he hands me one of the boxes with a page-boy wig in it and the other box with some basic makeup in it.
“I want to try on some stockings,” I say. Looking at all these items, I have realised that I have got to my present age without ever having worn any stockings. I pick up a pair of sheer white ones and the white garter belt. Sit on the edge of the sofa and take off my socks and then my short skirt, as it hinders my efforts to put on the garter belt. I slip the garter tabs under the waistline of my cotton briefs and out of the leg holes. Robert is sitting in the desk chair opposite me, and I notice that his shorts are beginning to bulge again. The fact that he can see my wet cotton knickers, which are hiding very little, clearly adds to his excitement. I teasingly take my time pulling on the stockings, stroking them smooth, and clipping them to the garter tabs. His shorts can barely contain his erection, much to my pleasure.
“I bet you would look sexy in this,” he says, as he holds up the sheer baby doll nightie.
“You want to see me in that?” I ask.
“Gosh, yes, sis.”
“I will, but only if you get dressed as well.”
“Me get dressed?”
“Yes. You want to see me in something sexy. I want to see you the same way.”
“What. In a nightie?”
“Stockings, bra, panties, and a slip.”
“No way.”
“I’m only playing if you are.”
I know what he wants. He wants to see me nude or almost so. He saw me naked a couple of months back when we bumped into each other as I was coming out of the bathroom, and I dropped the towel I had wrapped around me. He got an eye full when I picked it up. Scuttled back to his room, and imagining what he was doing caused me to get wet too. I can see he is considering my reply, and then he makes up his mind.
“Ok, but only if no one knows.”
“Strictly between us,” I confirm. Then lay out what I want him to wear. Sheer black stockings, a black satin bra and panty set, a sheer silk slip.
“There you are,” I say, and add, “We change here.”
“But, you’ll see…”
“Don’t be silly. I saw your stiff cock when you were in my bedroom looking at the mags.”
“Oh.”
“You want to see my fanny, ‘cos sheer panties won’t hide it, and I want to see your cock.”
“Oh, right.”
With this, I stand up and take off my T-shirt, exciting my stiff nipples as I do so. Pick up the baby doll top and slip it on. If Robert wasn’t excited before, he certainly is now. He stands and undoes his shorts that slide to the floor. His briefs exhibit a large wet patch and clearly are equal to my knickers for wetness. The tip of his cock protrudes above the waistband, and seeing it gets me even wetter. He pauses before pushing his briefs down his legs. I hand him the garter belt and stockings.
“Put these on first,” I say, “It will make the rest easier.”
He slides the stockings up his legs but struggles with clipping them to the garter tabs.
“Here, I’ll help you,” I say, and slide my hands up his leg before attaching the stocking top to the garter tab. Doing this makes his cock bob with excitement, and me wetter still. He lets me do the same for his other leg. Then I hand him the satin panties. Slipping out of my soaking knickers, I pull the sheer baby doll panties up my legs. Robert has managed the bra and is smoothing down the slip that covers all but hides nothing. The wig and some pale pink lipstick for both of us, and we are complete.
“Goodness, you make a pretty girl,” I say. Robert flushes slightly at my compliment.
“Let’s go and see how we both look.”
“How?”
“The big mirror in mum’s room,” I say.
I grasp Robert’s hand and lead him down the passage to Mum’s bedroom. Standing in front of the mirror, I am aware that Robert is surprised to see two sexily dressed girls staring back at him. He is definitely turned on by the sight of the girl with the page-boy hairstyle and visible undies, not hidden by the sheer silk slip. I can see his cock getting stiffer in the satin panties he is wearing.
“I can’t call you Robert when you look as sexy as that,” I say, “I know. You are my new girlfriend, Bobbie, and will be whenever you are dressed like this for me. Just for me.”
We edge backwards from the mirror and fall backwards onto the bed, side by side. Then we are kissing, and he is fondling me even as I stroke him through his slip and panties. Moments later, we both explode and are left wet and breathless.
A little while later, we know we have to go back to the utility room and tidy up.
I am wondering if I will ever see Bobbie in the future.
