Perfect Holiday

Perfect Holiday

“C’mon baby, are you getting a little horny, didn’t you have enough fun earlier?” I couldn’t answer. “Try on the knickers on top of the slip!” – “Julie, I…” – “Shhhhh, c’mon, you’ll have even more fun when you wear ’em both.” What was she talking about? Fun? Did she know about my deepest and most ridiculous desires? That I started putting on mummies pants when I was ten or twelve and that I had put hers on every once in a while. That I even owned two black lacy panties and a camisole myself?

I put on the knickers and it felt wonderful. The silk that would have flown freely around her legs was snugly around mine. But even more wonderful was the feel of me wearing her panties right before her eyes.

“Now put on the khaki pants, darling and that white blouse. You can’t wear the other stuff anyways, it’s too tight.” I did as I was told. The khaki pants had a very low waistline and the top of the knickers was almost showing a little. It also created a very feminine look to my butt. The blouse…I started fumbling around with the buttons, but they work the other way around. Julie stepped up to me and helped me.

“Now let’s see, what my darling looks like in his girlfriends clothes.” She turned me around before the big mirror inside the cabinet. It was horrible. I looked like a man wearing his girlfriend’s clothes. And the sharp curve of the khaki-pant’s seamline showed a distinctive bulge where nothing’s supposed to be there. “Now if you can control your little weenie a little bit, we’ll be all set for dinner. No wait, something’s missing!” Julie dashed into the bathroom, rushed back out and before I could notice, she pumped two big loads of her daytime cologne on me. It wasn’t the heavy feminine evening scent that she was wearing right now, but it sure was a sweet sporty women’s note. “Julie!” I started to protest. “There you go! She completely ignored me. “Put on your silly sneakers and off to dinner.” My sneakers. At least one token of my manhood.

I couldn’t speak a word in the elevator. The dinner room was dimly lit for the special occasion with candles burning on the tables. What a relief! I was hoping for a quick low-profile way to our table. The blouse wasn’t too bad, when I was sitting down. But fate had other plans for me. We had to stand in line to be seated, register on the desk as new guests. Then the hotel manager handed us a welcome drink. Julie started a little chat-chat with him. I felt a thousand eyes piercing me. “Julie, let’s go to our table.” I mumbled to her. No reaction. After three or four minutes of standing around which seemed like two hours to me, a female host approached us and offered to escort us to our table. She looked me up and down and smiled her biggest smile.

Once we were seated I started to relax a little. But Julie wouldn’t give me a break. She took off one shoe under the table and started to rub her foot on my crotch. “Darling, this is so sweet of you! It’s so nice to spend this evening in such lovely company. Just look at you! Everyone adores you!” As I looked around I wasn’t sure what everyone was having a good time about, but I couldn’t rule out that they were mocking themselves at me.

The only thing that kept me alive at that point was that my luggage should really be arriving any time from now. My laundry would be back tomorrow morning and that would save my day. And I could also shop for some new clothes. Dinner started and it sure was great. We had some excellent wine and I started to relax under the influence of the booze. So finally, we skipped desert and I didn’t mind stepping out the hotel and going on a little walk in the park. Julie reached under my blouse and started to rub my nipples. “Honey, I now what you’re up to and I can’t wait to get back in our room.” – “Yes Julie, neither can I.”

As soon as we got into the room, I started to undress. The blouse, the pants, the knickers. Julie’s hand stopped me there. She sat me down on the bed. “Wait Honey, not too quickly. Let’s enjoy this a little longer. Strip to the cotton panties and wait here, I’ll be back.” She disappeared in the bathroom. I was sitting on the bed feeling silly and confused. What else did she have in mind? She returned with a matching bra, stockings and makeup. “Put that on!” I wanted to protest but she kissed me on my mouth before I could say anything. “Please Honey, you look so adorable.” She quickly painted my lips, lashed my eyebrows and laces. I got into the bra and the stockings. Again, she led me to the mirror. She fumbled some stockings out of her suitcase and stuffed the bra. “Perfect, Baby, now you have permission to suck my freshly shaved dripping cunt.” I sighed and started working my way down, kneeing in front of her. After a while we reached the point where she would have usually started to work on my penis. Not this time. She pulled down the pink panties, took my hand, led it to my penis and wrapped it around it. “Now jack yourself off, Darling. Do it!” I couldn’t believe it. She held her pussy inches away from my hard dick. I was constantly trying to touch her with the tip of my cock, but she always retreated. She was teasing the hell out of me. When I finally came, she soaked all my juice up with the pink slip. “Good girl,” she said after a while. And that got me so excited that I wanted to get into her right away. “Easy, easy, Darling, go clean yourself up and come back to bed. I put something for you to wear on the rod on the bathroomdoor.

I undressed and showered in complete darkness, I was just too embarrassed to look at me. I toweled me dry and reached for the door. I put on whatever hung there. A long tanktop-thing. I opened the door and Julie was stretched out on the bed watching TV. “Snuggle up sweetie. You look so cute I just love the thought that you’re mine.” I looked down on myself. I was wearing a nightgown! I quickly got under the comforter. I was ready to pass out. Julie kissed me good-night and turned off the lights. I was asleep in no time.

The next morning I woke up to Julie talking on the phone. She was ordering breakfast through room-service. I started to recall what had happened yesterday and hoped that this was the beginning of a day back to normal. Breakfast in bed! “Morning, Honey,” I said and kissed Julie. She kissed me and I dozed off again. I finally woke up startled a few minutes later. Someone was knocking on the door and yelling “Hello, room-service!” I could hear the shower running. Guess I’ll have to get it. I jumped out of bed, opended the door. A cute young woman was waiting with a roll-in tray stacked with breakfast. She looked at me, smiled, curtsied and ran off. I hesitated a moment only to realize that I was still wearing a woman’s nightgown. I rolled the tray in quickly, when Julie stepped out of the bathroom. “Hi Darling, I see you got that door.” – “Julie, I was still wearing these!” I blushed. “It’s all right, don’t worry darling, we’ll get something more appropriate for you soon. Now let’s have breakfast!”

After breakfast Julie suggested going to the pool. I didn’t even have to say anything. “Now don’t give me that look, darling. What’s the difference between wearing trunks and this?” She handed me swimsuit. “All my bikini pants are thongs, but you can roll the top down like this, look honey.” I put on the swimsuit and rolled the top down. She rolled it back up. “Much nicer this way, but hey – you decide, okay? And you can put on this one when this one’s wet.” She handed me a rather fluffy pink one-piece. “Just kidding, okay.” I rolled the swimsuit back down and we went off to the pool. On the pool I was handed a portable phone with the airline on the other end. No trace of my luggage. They’d keep me posted, but I should better look into buying something new sooner or later. I checked with the porter for my laundry and was told that it would be taken to my room. We took a little dip in the pool and Julie swam up to me. “Roll that piece up or do you want to end up naked?” So I swam around a while – wearing my girlfriends swimsuit. I was just a little too tall for it. “We have to go shopping this afternoon. You can’t go on ruining my stuff, can you?” Back in our room, I opened my laundry wrapped in paper. Only that it wasn’t mine. O my god, is this ever gonna end? “Honey, don’t worry, you can wear what you wore last night one last time, we go out shopping and when we get back you’re all dressed up like never before!” I didn’t bother the khaki pants and the blouse anymore, as long as it would buy me some clothes.

When Julia was apllying her make-up to get ready she was kidding me “Wanna try some lipstick, too?” I blushed. “Of course not!” – “Well why not, honey? Looks good on me, don’t you? C’mon, gimme a kiss.” She kissed me real hard on my lips and there I was with lipstick all over it. “And don’t you dare to wipe it off!”

We headed down to the shopping district in a cab, me trying to hide from the cabbie. Our first stop was a drug store – nowhere to buy stuff for me. Julie got three cans of something I couldn’t figure out what it was, some lipstick and tampons. She also got some fancy fake jewellery like ear-clips, slutty stuff that wasn’t her style. But I wasn’t gonna argue about that, I was only waiting for her to leave the shop so that we could finally buy me some stuff. Next stop was – a lingerie store. Okay, okay, I had to relax, I love it when Julie wears lingerie anyways. She had me sit on a couch in the front of the store and started buzzing through the store with the salesperson. The two of them had quite a good time, giggling and bursting with laughter at times. Julia came from the cashier with three stuffed bags.

Back on the street Julia smiled her biggest smile at me: “Just one more stop, honey, and we’re all set. Only this time, I’ll really need your help.” We entered a large department store and Julia headed straight to a fiftysomething salesperson in the women’s apparel department. “We’re here to see Ms Clark.” – “Oh, that’s me. And this must be the customer.” She gave me a friendly nod. “Please follow along.” I was taken into the changing section, to a somewhat remote cabin. “Julia, what’s this supposed to be?” – “Oh shut up now darling. Take off my clothes!” I did as I was told. Julia snapped them immediately. “Here, put on this bra and panties. They’re your size!” – “But, Julia!” – “No more need to ruin my panties and put ugly stains in them, darling. From now on, you’ll were your own panties. And nothing but panties, believe me. And before you start arguing: We’re in a foreign country, you’re standing in a female changing room of a department store, wearing nothing but my lingerie. If you don’t do as I tell you, you’ll be in jail in five minutes. And they would love to meet a sissy like you, believe me!” I couldn’t breathe. For a second, my world stopped turning. “Hello? Are you still with me?” – “Ah sure, darling…”

So I put on the bra and panties and yes, they were my size, except that I couldn’t even fill the A-cup brasserie and the panties turned out to be an extra-tiny g-sting. “Hurry up, or do you want the salesperson to see your ridiculously small weenie?”

I yanked my two inches into the thong and along came the salesperson. “Hi, I’m Ms Clark and you are…?” – “Christine,”, Julia quickly answered. Name’s Christine.” – “Okay Christine, now let’s see what we have here. I have prepared an assortment of different things for different occasions: Leisure, activities, evening, formal. I’ve decided to go for a rather plain young style, if you want it to be more classically feminine, just let me know.”

To be continued…

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lola

It has only been a week but what a week this site is awesome and the Staff is so wonderful to deal with i am an older sissy and sadly my wife could never know. that’s sad because our life… Read more “lola”

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