“See the fine weave, Teddy?” Diana put her hand into the stocking and showed me her palm through the diaphanous mesh. “See how silky it is? This is six denier, one of the finest nylon weaves you can buy. It’s so light and airy, you might forget you’re wearing them. Go ahead, put them on. You’ll love how they feel.”
When I did, I realized she was right. Every stocking we tried was sexier than the last. We maximized the pleasure by sliding each other’s hands all around our legs, evaluating each pair of nylons for its silky feel and slipperiness.
By the time we’d each tried on a dozen pairs of her nylons, my dick was a throbbing, twitching thing. Again.
I had a rock-solid boner for the entire time I was with her. I had given up trying to hide it from her.
“Teddy, I have an idea. Seeing you like this, trusting me completely as you are, it makes me feel all warm inside. For a long, long time, I’ve had this fantasy about going out with a guy who would do anything for me. Seriously, I mean anything.”
“Like what?”
“Well, like trying on all my nylons with me, for starters. Call me crazy, but in my dreams I think about dating a guy who wears women’s clothes, loves gorgeous filmy nylons, goes with me to restaurants, cuddles up nice and close. You know what I mean, right?”
“If you’re thinking what I think you are, you’re going to have to be really specific Di.”
“I want to go on a date with you, Teddy. I want to dress you up like a gorgeous girl and pretend we’re lesbian lovers. Wouldn’t that be a blast? Do this for me, Teddy. You don’t have to kiss me or anything. Just pretend. Indulge my fantasy. I’ve never found any man that would do this for me. Please? Can you do this for me? Please?”
“How would we ever pull that off, Diana?”
“We can do it! Look, I’m invited to a summer Hallowe’en-themed party next week. I want you to come with me. We can spend the week getting you ready. I’ll go as a sexy vampire. You can be my date. You can be my demon Succubus lover.
“Let’s do a dry run. We’ll go on a date and I’ll practise my makeup skills on you. I’m sure I’ve got some dresses you’d fit into. You’re so slim; you hardly have any muscle. Your legs are nice and long. Your facial features are soft enough, and with my makeup skills, I can get you looking like a girl, no problem. In fact, I think I can make you really pretty. What do you say?”
I looked into Diana’s eyes and I saw real hope there. I was stunned that this gorgeous, leggy woman couldn’t get a date. At least not on her terms. I was so intrigued that she wanted her brother to be her date on an incredibly sexy night.
This was a turning point for me. At this exact moment I made a momentous decision. One that would forever change my life and set me on an unstoppable path. I just didn’t know where it would lead.
At that instant I resolved that I wanted to fuck my sister. And I was nearly convinced she felt the same way.
So how to broach the subject?
I couldn’t just ask her outright. If I was wrong, if she really was just having some innocent fun with me, I’d completely ruin what we were building together. We’d never be able to speak rationally with each other again. And the sexy dress-up afternoons would end.
So I decided I would go along with whatever fetish my sister wanted to indulge in. If she wanted to dress me like a girl, go on a date, and pretend to be my lesbian lover, well, I was all in on that and we’d see where it leads. Maybe, just maybe we’ll bridge that gulf between us.
I took her hand. “I say, Yes. I’ll do it.”
Diana squealed in delight. “Oh boy, oh boy, this is going to be great! I can’t wait. I’m so excited! For the party, I’m taking you shopping Teddy. I know just the place. It’s super-sexy little store that sells EVERYTHING. I’m rethinking my own costume too. The one I’ve got isn’t sexy enough. We’re going all in on this. Sexy, slutty. I’m going to layer you up in crotchless pantyhose and French stockings. I’m doing the same. And I need you to practice your high heel skills. We’ll buy five-inch heels for you. You’re going to wear them all week. Don’t worry, I’ll teach you how. All sexy Succubi have to wear sky-high stilettos and stockings, Teddy. Oh yeah, you’re going to need a new name. I can’t call you Teddy when we’re out together. That wouldn’t do. Tessy. That’s it. Tessy, the Slutty Succubus from Hell. That’s perfect! You’ll be the Slutty Succubus dating the cocksucking Vampire. Oops! Did I really say that?
“We’re going to dress up as the most depraved, horny sluts in all of hell. Don’t worry, I can see it on your face. I won’t leave you alone, not for a second. I’m a horny slut, I mean, that’s what I’ll pretend to be in costume, but just for my date. I won’t pretend to be horny for anyone else at the party. Just for my slutty Succubus whore. This is going to be amazing. Fuck I’m getting horny already. Maybe you should go to your room for a few minutes while I…no, I want to spend the day with you feeling all slutty and charged up. That’ll make the shopping loads more fun. Both of us will be totally on edge. Come on, let’s go.”
I started to take the stockings off when Diana put her hand on my arm. “Oh no you don’t. Do you see me taking off my stockings? We’re going like this. You can put on a pair of pants but the heels stay. You’re going to need a lot of practice in those. We’ll just tell the store staff it’s part of getting ready for the party.”
What the hell. In for a penny, in for a pound. I was all in.
***
When we got to the store, I was not prepared for what awaited us. This was an outfitter for strippers. A den of perversion for sex-brained women.
I loved it.
The staff was comprised entirely of young women in their early twenties. They were all dressed in fetish wear. Fishnet stockings, push up bras, tanks with no bras, tiny pussy-brushing skater skirts, sky-high platform heels, brilliant high-gloss stockings with garters below hemlines, lots of brilliant-colored tattoos, some piercings, wild hair with feathers and jewelry. You get the idea.
When we got there, it was a slow time of day. We were the only customers.
Diana told them our plan and the whole staff seemed to burst with energy and enthusiasm. When Diana told them I was already wearing stockings, four of them pulled me behind a display, released my belt and literally stripped me on the spot.
“Oooh, look. His legs are fantastic!”
“Sexy. So slutty!.”
“I love your stockings!”
“Diana, you are a lucky girl! Where did you find a guy to do this for you?”
“What’s your name, honey?”
“Her name is Tessy.”
“Oooh! Tessy!”
“Her voice is so hot. Low and soft. It gives me goosebumps in all the right places!”
“Tessy, Tessy, Tessy, do you want to try on my stockings? Come on, let’s trade!”
“Me too. Let’s all trade!”
“I’ve got the perfect Succubus outfit for you Sweetheart.”
“You’re waist is nice and tiny. And your legs are sooo long. We can get you all girly easy!”
“But you’re going to need some real tits.”
“What’s his bra size? He looks like 34.”
“Not ‘his’ silly. ‘Hers’. What’s Tessy’s bra size?”
“This is the perfect place for the ballerina top.”
“No, no, no. Corset. She needs a corset!”
“Fishnets! Fishnets!”
“Silk stockings!”
“Fully fashioneds!”
“No, no, all of them. We’ve got to layer her.'”
“I’ll get the silicon implants.”
“Give her a D Cup!”
“Come on! She’s a Succubus. At least make them E’s!”
“34EE it is!”
“Get two,” Diana said. “He’ll need two bras. Make one a C though.”
“Wings. We need wings!”
“This wig is perfect!”
“Fuck I wish I had hair like that!”
“Come on girls. Let’s get him into the dressing room. OK Diana?”
“He’s all yours ladies. I want him so sexy that a slutty vampire wouldn’t be able to resist him. Meanwhile, I’ll need another wig for every day. You take him, I’ll find a nice long-hair wig and a bra.”
Eight hands grabbed hold of me and dragged me to a dressing room. Two of the girls, one dressed as an office slut, with a micro-mini skirt and fishnet stockings with garters, massive black hair hanging to her bare midriff, huge barely-covered tits, and six-inch stilettos, the other dressed as a Dallas cheerleader, held on to me while the other two went to fetch their costume ideas for me.
The “office slut” hugged my arm and whispered to me. “I’ve always dreamed of having a hetero slut boy who could fit into all my clothes. If this thing with Diana doesn’t work out, call me.”
When the girls returned, Diana crowded in with us. They stripped me right to my underwear. Of course my boner was unstoppable and they all ooo’d and aw’d at its girth and size.
“This slut needs panties!”
“Diana, honey. Unless you want him presenting as a tranny, we’ve got to get that monster under control!”
I couldn’t believe how these spectacular girls were talking so openly about my cock. It made me even harder. The tent in my underwear was huge.
“Red Alert! Red Alert!” laughed the Cheerleader.
“Something this big is gonna be hard to hide,” said a girl dressed as a sexy pilot, complete with bomber jacket. Only instead of flight pants, she wore skin-tight micro shorts with fishnet stockings and thigh-high stiletto leather boots.
“Tessy, you’re going to have to strap in for the party. OK honey?”
The girls brought everything they could think of into the dressing room. I didn’t have to do much, they dressed me themselves, eight hands working on me all at once. I got several little kisses thrown in on my face and neck, lots of gorgeous boobs pressed into me, and they patted and petted and smoothed everything out as I tried things on. As various articles of costume went on my body, the girls would all poke and prod and caress the fabric, and me.
Fuck it was exciting.
The sexiest part for me was when office slut girl put her hand on my chest. “Tessy, I just love your nylons. Can I try them on? You can try my fishnets. Come on, it’ll be fun.”
“I’d love to, Laura,” I said. “Believe it or not, I’ve never tried fishnets.”
“I’m going to have to speak to that girl of yours. Come on, let’s trade.”
Laura sat down, peeled off her fishnets and gave them to me to try on. I sat beside her and did the same. As we were putting on each other’s stockings, the other girls seemed to take a hint and left us alone. Laura must have given them some secret signal.
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